# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_year ? _journal_page_first ? loop_ _publ_author_name 'Francois Leca' 'Mathieu Sauthier' 'B.le Guennic' 'Christophe Lescop' 'Loic Toupet' 'Jean-Francois Halet' ; R.Reau ; _publ_contact_author_name 'Régis Réau' _publ_contact_author_address ; UMR 6509 CNRS-Université de Rennes 1, Institut de Chimie, Campus de Beaulieu, 35042 Rennes Cedex, France ; _publ_contact_author_email regis.reau@univ-rennes1.fr _publ_section_title ; Stereospecific isomerisation of P-heterocycles triggered by coordination: Synthesis of the first P,N-chelates featuring a 2- phospholene moiety. ; _publ_section_references ; A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi, A.G.G. Moliterni, G. Polidori, R. Spagna. Sir97: a new tool for crystal structure determination and refinement. Jr of Applied Crystallography (1999) vol 32, pp 115-119. L. J. Farrugia, J. Appl. Cryst (1997), 30, 565 Sheldrick, G.M. (1997).SHELX97. Program for the Refinement of Crystal Structures, Univ. of Göttingen, Germany. Spek, A.L. (1998) PLATON. A multipurpose crystallographic tool, Utrecht University, Utrecht, The Netherlands. ; data_compound_1c' _database_code_CSD 208509 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H26 Cl2 N P Pd S' _chemical_formula_weight 556.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 10.3320(2) _cell_length_b 17.1370(5) _cell_length_c 13.1100(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.6950(10) _cell_angle_gamma 90.00 _cell_volume 2223.40(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 1.252 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method none _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 5046 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5046 _reflns_number_gt 3887 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.0415P)^2^+6.2387P] 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 SHELXL _refine_ls_extinction_coef 0.0012(3) _refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5046 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0662 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1840(4) 0.1115(3) 0.7001(4) 0.0235(9) Uani 1 1 d . . . C2 C 0.1004(5) 0.1244(3) 0.6011(4) 0.0246(9) Uani 1 1 d . . . C3 C 0.1405(5) 0.1650(3) 0.5131(4) 0.0291(10) Uani 1 1 d . . . H3A H 0.2273 0.1451 0.5102 0.035 Uiso 1 1 calc R . . H3B H 0.1505 0.2204 0.5284 0.035 Uiso 1 1 calc R . . C4 C 0.0363(5) 0.1529(3) 0.4050(4) 0.0355(12) Uani 1 1 d . . . H4A H 0.0559 0.1876 0.3529 0.043 Uiso 1 1 calc R . . H4B H 0.0413 0.0996 0.3814 0.043 Uiso 1 1 calc R . . C5 C -0.1044(5) 0.1691(3) 0.4132(4) 0.0357(12) Uani 1 1 d . . . H5A H -0.1683 0.1694 0.3426 0.043 Uiso 1 1 calc R . . H5B H -0.1066 0.2200 0.4450 0.043 Uiso 1 1 calc R . . C6 C -0.1439(5) 0.1064(3) 0.4814(4) 0.0306(11) Uani 1 1 d . . . H6A H -0.2268 0.1220 0.4964 0.037 Uiso 1 1 calc R . . H6B H -0.1617 0.0580 0.4413 0.037 Uiso 1 1 calc R . . C7 C -0.0370(4) 0.0919(3) 0.5850(3) 0.0241(9) Uani 1 1 d . . . C8 C -0.0547(4) 0.0493(3) 0.6683(3) 0.0207(9) Uani 1 1 d . . . C9 C -0.1744(4) 0.0121(3) 0.6819(4) 0.0231(9) Uani 1 1 d . . . C10 C -0.1804(4) -0.0311(3) 0.7688(4) 0.0241(9) Uani 1 1 d . . . H10 H -0.1069 -0.0384 0.8286 0.029 Uiso 1 1 calc R . . C11 C -0.3105(4) -0.0634(3) 0.7580(4) 0.0273(10) Uani 1 1 d . . . H11 H -0.3311 -0.0943 0.8095 0.033 Uiso 1 1 calc R . . C12 C -0.4008(5) -0.0441(3) 0.6644(4) 0.0332(11) Uani 1 1 d . . . H12 H -0.4906 -0.0600 0.6444 0.040 Uiso 1 1 calc R . . C13 C 0.3310(4) 0.1155(3) 0.7422(4) 0.0252(9) Uani 1 1 d . . . C14 C 0.4124(5) 0.1728(3) 0.7178(4) 0.0307(11) Uani 1 1 d . . . H14 H 0.3747 0.2120 0.6693 0.037 Uiso 1 1 calc R . . C15 C 0.5506(5) 0.1709(3) 0.7665(4) 0.0305(11) Uani 1 1 d . . . H15 H 0.6066 0.2078 0.7489 0.037 Uiso 1 1 calc R . . C16 C 0.6046(5) 0.1143(3) 0.8410(4) 0.0308(11) Uani 1 1 d . . . H16 H 0.6964 0.1139 0.8771 0.037 Uiso 1 1 calc R . . C17 C 0.5188(4) 0.0574(3) 0.8613(4) 0.0261(9) Uani 1 1 d . . . H17 H 0.5554 0.0185 0.9105 0.031 Uiso 1 1 calc R . . C20 C 0.0544(4) 0.1225(2) 0.8747(3) 0.0199(8) Uani 1 1 d . . . H20 H 0.0097 0.0913 0.9175 0.024 Uiso 1 1 calc R . . C21 C -0.0448(4) 0.1864(3) 0.8174(4) 0.0234(9) Uani 1 1 d . . . H21A H -0.0058 0.2151 0.7696 0.028 Uiso 1 1 calc R . . H21B H -0.1280 0.1625 0.7752 0.028 Uiso 1 1 calc R . . C22 C -0.0757(4) 0.2428(3) 0.8980(4) 0.0242(9) Uani 1 1 d . . . H22A H -0.1337 0.2844 0.8603 0.029 Uiso 1 1 calc R . . H22B H -0.1233 0.2152 0.9408 0.029 Uiso 1 1 calc R . . C23 C 0.0543(4) 0.2777(3) 0.9702(4) 0.0275(10) Uani 1 1 d . . . H23A H 0.0325 0.3118 1.0219 0.033 Uiso 1 1 calc R . . H23B H 0.0979 0.3088 0.9278 0.033 Uiso 1 1 calc R . . C24 C 0.1513(4) 0.2143(3) 1.0284(4) 0.0270(10) Uani 1 1 d . . . H24A H 0.1110 0.1862 1.0759 0.032 Uiso 1 1 calc R . . H24B H 0.2342 0.2383 1.0712 0.032 Uiso 1 1 calc R . . C25 C 0.1841(4) 0.1569(3) 0.9497(4) 0.0252(9) Uani 1 1 d . . . H25A H 0.2401 0.1150 0.9887 0.030 Uiso 1 1 calc R . . H25B H 0.2345 0.1836 0.9081 0.030 Uiso 1 1 calc R . . N1 N 0.3867(3) 0.0566(2) 0.8130(3) 0.0230(8) Uani 1 1 d . . . P1 P 0.09932(10) 0.05669(7) 0.77832(9) 0.0198(2) Uani 1 1 d . . . S1 S -0.33163(12) 0.01239(8) 0.58711(10) 0.0321(3) Uani 1 1 d . . . Cl1 Cl 0.12181(9) -0.12014(6) 0.88368(8) 0.0226(2) Uani 1 1 d . . . Cl2 Cl 0.43955(10) -0.12465(7) 0.88256(10) 0.0283(3) Uani 1 1 d . . . Pd1 Pd 0.26254(3) -0.031491(19) 0.83986(3) 0.02033(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 C1 0.022(2) 0.025(2) 0.027(2) 0.0036(18) 0.0125(18) 0.0034(17) C2 0.031(2) 0.021(2) 0.026(2) 0.0025(18) 0.014(2) 0.0058(18) C3 0.038(3) 0.025(3) 0.030(2) 0.0041(19) 0.020(2) 0.006(2) C4 0.049(3) 0.035(3) 0.028(3) 0.006(2) 0.019(2) 0.013(2) C5 0.046(3) 0.035(3) 0.026(2) 0.005(2) 0.009(2) 0.020(2) C6 0.030(2) 0.036(3) 0.024(2) 0.005(2) 0.006(2) 0.014(2) C7 0.027(2) 0.024(2) 0.021(2) -0.0016(18) 0.0066(18) 0.0067(18) C8 0.0200(19) 0.022(2) 0.020(2) 0.0002(16) 0.0054(17) 0.0033(16) C9 0.020(2) 0.022(2) 0.027(2) -0.0024(17) 0.0047(18) 0.0031(16) C10 0.0186(19) 0.028(2) 0.025(2) -0.0019(19) 0.0051(17) 0.0009(17) C11 0.023(2) 0.026(2) 0.031(2) -0.0008(19) 0.0058(19) -0.0024(18) C12 0.020(2) 0.035(3) 0.040(3) -0.007(2) 0.001(2) -0.0059(19) C13 0.026(2) 0.024(2) 0.030(2) 0.0014(19) 0.0149(19) 0.0009(18) C14 0.035(2) 0.027(3) 0.037(3) 0.002(2) 0.021(2) 0.001(2) C15 0.029(2) 0.029(3) 0.041(3) -0.005(2) 0.023(2) -0.0090(19) C16 0.020(2) 0.032(3) 0.042(3) -0.007(2) 0.012(2) -0.0059(18) C17 0.019(2) 0.027(2) 0.032(2) -0.0035(19) 0.0068(19) -0.0001(17) C20 0.0175(19) 0.024(2) 0.020(2) 0.0016(17) 0.0073(17) -0.0027(16) C21 0.0180(19) 0.026(2) 0.026(2) 0.0002(18) 0.0066(17) -0.0029(17) C22 0.022(2) 0.022(2) 0.029(2) 0.0024(18) 0.0080(18) 0.0008(17) C23 0.027(2) 0.026(2) 0.030(2) -0.0043(19) 0.009(2) -0.0049(19) C24 0.027(2) 0.029(3) 0.026(2) -0.0023(19) 0.0081(19) -0.0061(19) C25 0.019(2) 0.031(3) 0.024(2) 0.0000(19) 0.0038(18) -0.0027(17) N1 0.0203(17) 0.0230(19) 0.0268(19) 0.0010(15) 0.0087(15) -0.0003(14) P1 0.0173(5) 0.0217(6) 0.0208(5) 0.0022(4) 0.0061(4) 0.0000(4) S1 0.0247(5) 0.0358(7) 0.0289(6) -0.0002(5) -0.0032(5) -0.0009(5) Cl1 0.0164(4) 0.0251(5) 0.0268(5) 0.0087(4) 0.0070(4) -0.0024(4) Cl2 0.0176(5) 0.0295(6) 0.0400(6) 0.0106(5) 0.0119(5) 0.0048(4) Pd1 0.01672(17) 0.02263(19) 0.02242(18) 0.00280(13) 0.00688(12) -0.00012(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.354(6) . ? C1 C13 1.461(6) . ? C1 P1 1.794(4) . ? C2 C7 1.483(6) . ? C2 C3 1.504(6) . ? C3 C4 1.527(7) . ? C4 C5 1.513(7) . ? C5 C6 1.528(7) . ? C6 C7 1.505(6) . ? C7 C8 1.369(6) . ? C8 C9 1.448(6) . ? C8 P1 1.819(4) . ? C9 C10 1.374(6) . ? C9 S1 1.739(4) . ? C10 C11 1.423(6) . ? C11 C12 1.352(7) . ? C12 S1 1.700(5) . ? C13 N1 1.381(6) . ? C13 C14 1.389(6) . ? C14 C15 1.387(7) . ? C15 C16 1.377(7) . ? C16 C17 1.393(6) . ? C17 N1 1.329(5) . ? C20 C25 1.534(6) . ? C20 C21 1.540(6) . ? C20 P1 1.849(4) . ? C21 C22 1.531(6) . ? C22 C23 1.525(6) . ? C23 C24 1.525(7) . ? C24 C25 1.533(6) . ? N1 Pd1 2.076(4) . ? P1 Pd1 2.2353(11) . ? Cl1 Pd1 2.2874(10) . ? Cl2 Pd1 2.3704(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C13 131.5(4) . . ? C2 C1 P1 110.6(3) . . ? C13 C1 P1 115.7(3) . . ? C1 C2 C7 113.4(4) . . ? C1 C2 C3 124.8(4) . . ? C7 C2 C3 121.9(4) . . ? C2 C3 C4 111.9(4) . . ? C5 C4 C3 110.2(4) . . ? C4 C5 C6 109.6(4) . . ? C7 C6 C5 113.2(4) . . ? C8 C7 C2 115.4(4) . . ? C8 C7 C6 125.2(4) . . ? C2 C7 C6 119.4(4) . . ? C7 C8 C9 130.4(4) . . ? C7 C8 P1 108.0(3) . . ? C9 C8 P1 121.1(3) . . ? C10 C9 C8 125.7(4) . . ? C10 C9 S1 109.8(3) . . ? C8 C9 S1 124.5(3) . . ? C9 C10 C11 113.1(4) . . ? C12 C11 C10 112.4(4) . . ? C11 C12 S1 112.4(4) . . ? N1 C13 C14 120.6(4) . . ? N1 C13 C1 114.0(4) . . ? C14 C13 C1 125.4(4) . . ? C15 C14 C13 119.3(5) . . ? C16 C15 C14 119.8(4) . . ? C15 C16 C17 118.5(4) . . ? N1 C17 C16 122.7(5) . . ? C25 C20 C21 112.1(4) . . ? C25 C20 P1 109.1(3) . . ? C21 C20 P1 111.3(3) . . ? C22 C21 C20 110.7(4) . . ? C23 C22 C21 110.8(4) . . ? C22 C23 C24 111.5(4) . . ? C23 C24 C25 111.1(4) . . ? C24 C25 C20 110.9(3) . . ? C17 N1 C13 119.0(4) . . ? C17 N1 Pd1 121.8(3) . . ? C13 N1 Pd1 119.2(3) . . ? C1 P1 C8 92.4(2) . . ? C1 P1 C20 109.3(2) . . ? C8 P1 C20 104.44(19) . . ? C1 P1 Pd1 96.84(14) . . ? C8 P1 Pd1 129.56(15) . . ? C20 P1 Pd1 118.50(14) . . ? C12 S1 C9 92.2(2) . . ? N1 Pd1 P1 83.46(10) . . ? N1 Pd1 Cl1 173.77(11) . . ? P1 Pd1 Cl1 94.10(4) . . ? N1 Pd1 Cl2 93.29(10) . . ? P1 Pd1 Cl2 172.50(4) . . ? Cl1 Pd1 Cl2 89.79(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 C13 C1 C2 C7 163.0(5) . . . . ? P1 C1 C2 C7 1.3(5) . . . . ? C13 C1 C2 C3 -15.0(8) . . . . ? P1 C1 C2 C3 -176.8(4) . . . . ? C1 C2 C3 C4 166.0(4) . . . . ? C7 C2 C3 C4 -11.9(6) . . . . ? C2 C3 C4 C5 48.3(6) . . . . ? C3 C4 C5 C6 -68.3(6) . . . . ? C4 C5 C6 C7 48.9(6) . . . . ? C1 C2 C7 C8 -4.9(6) . . . . ? C3 C2 C7 C8 173.2(4) . . . . ? C1 C2 C7 C6 175.9(4) . . . . ? C3 C2 C7 C6 -6.0(6) . . . . ? C5 C6 C7 C8 168.1(4) . . . . ? C5 C6 C7 C2 -12.8(6) . . . . ? C2 C7 C8 C9 177.5(4) . . . . ? C6 C7 C8 C9 -3.4(8) . . . . ? C2 C7 C8 P1 5.8(5) . . . . ? C6 C7 C8 P1 -175.0(4) . . . . ? C7 C8 C9 C10 178.6(5) . . . . ? P1 C8 C9 C10 -10.7(6) . . . . ? C7 C8 C9 S1 1.2(7) . . . . ? P1 C8 C9 S1 171.9(2) . . . . ? C8 C9 C10 C11 -177.5(4) . . . . ? S1 C9 C10 C11 0.2(5) . . . . ? C9 C10 C11 C12 -0.4(6) . . . . ? C10 C11 C12 S1 0.4(6) . . . . ? C2 C1 C13 N1 -139.7(5) . . . . ? P1 C1 C13 N1 21.3(5) . . . . ? C2 C1 C13 C14 41.5(8) . . . . ? P1 C1 C13 C14 -157.5(4) . . . . ? N1 C13 C14 C15 -0.9(7) . . . . ? C1 C13 C14 C15 177.8(4) . . . . ? C13 C14 C15 C16 -2.4(7) . . . . ? C14 C15 C16 C17 3.4(7) . . . . ? C15 C16 C17 N1 -1.3(7) . . . . ? C25 C20 C21 C22 -54.7(4) . . . . ? P1 C20 C21 C22 -177.2(3) . . . . ? C20 C21 C22 C23 55.7(5) . . . . ? C21 C22 C23 C24 -57.2(5) . . . . ? C22 C23 C24 C25 56.7(5) . . . . ? C23 C24 C25 C20 -54.7(5) . . . . ? C21 C20 C25 C24 54.2(5) . . . . ? P1 C20 C25 C24 177.9(3) . . . . ? C16 C17 N1 C13 -1.9(7) . . . . ? C16 C17 N1 Pd1 177.3(3) . . . . ? C14 C13 N1 C17 3.0(7) . . . . ? C1 C13 N1 C17 -175.9(4) . . . . ? C14 C13 N1 Pd1 -176.2(3) . . . . ? C1 C13 N1 Pd1 4.9(5) . . . . ? C2 C1 P1 C8 1.6(4) . . . . ? C13 C1 P1 C8 -163.3(4) . . . . ? C2 C1 P1 C20 -104.6(3) . . . . ? C13 C1 P1 C20 90.5(4) . . . . ? C2 C1 P1 Pd1 132.0(3) . . . . ? C13 C1 P1 Pd1 -32.9(3) . . . . ? C7 C8 P1 C1 -4.2(3) . . . . ? C9 C8 P1 C1 -176.8(4) . . . . ? C7 C8 P1 C20 106.4(3) . . . . ? C9 C8 P1 C20 -66.2(4) . . . . ? C7 C8 P1 Pd1 -105.2(3) . . . . ? C9 C8 P1 Pd1 82.2(4) . . . . ? C25 C20 P1 C1 -61.7(3) . . . . ? C21 C20 P1 C1 62.5(3) . . . . ? C25 C20 P1 C8 -159.5(3) . . . . ? C21 C20 P1 C8 -35.4(3) . . . . ? C25 C20 P1 Pd1 47.8(3) . . . . ? C21 C20 P1 Pd1 172.0(2) . . . . ? C11 C12 S1 C9 -0.3(4) . . . . ? C10 C9 S1 C12 0.0(4) . . . . ? C8 C9 S1 C12 177.7(4) . . . . ? C17 N1 Pd1 P1 159.3(3) . . . . ? C13 N1 Pd1 P1 -21.5(3) . . . . ? C17 N1 Pd1 Cl1 92.0(10) . . . . ? C13 N1 Pd1 Cl1 -88.8(10) . . . . ? C17 N1 Pd1 Cl2 -27.5(3) . . . . ? C13 N1 Pd1 Cl2 151.7(3) . . . . ? C1 P1 Pd1 N1 25.37(19) . . . . ? C8 P1 Pd1 N1 124.2(2) . . . . ? C20 P1 Pd1 N1 -91.01(18) . . . . ? C1 P1 Pd1 Cl1 -160.39(15) . . . . ? C8 P1 Pd1 Cl1 -61.51(18) . . . . ? C20 P1 Pd1 Cl1 83.24(15) . . . . ? C1 P1 Pd1 Cl2 -39.2(4) . . . . ? C8 P1 Pd1 Cl2 59.6(4) . . . . ? C20 P1 Pd1 Cl2 -155.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.916 _refine_diff_density_min -1.185 _refine_diff_density_rms 0.128 #====END ############################################################################## data_compound_2a _database_code_CSD 208510 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C51 H48 Cl10 N4 P2 Pd2' _chemical_formula_weight 1346.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' Pd Pd -0.9988 1.0072 '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 14.985(5) _cell_length_b 9.785(5) _cell_length_c 37.375(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.388(5) _cell_angle_gamma 90.00 _cell_volume 5422(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2696 _exptl_absorpt_coefficient_mu 1.255 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method none _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 6991 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -48 _diffrn_reflns_limit_l_max 48 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5167 _reflns_number_gt 4216 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.0294P)^2^+18.4878P] 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 5167 _refine_ls_number_parameters 324 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.0977 _refine_ls_wR_factor_gt 0.0909 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.652 _refine_ls_shift/su_mean 0.020 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3084(3) 0.1893(4) 0.61771(10) 0.0377(9) Uani 1 1 d . . . C2 C 0.2561(3) 0.0795(4) 0.59509(10) 0.0351(8) Uani 1 1 d . . . C3 C 0.2633(3) -0.0550(4) 0.60228(12) 0.0464(10) Uani 1 1 d . . . C4 C 0.2089(4) -0.1598(4) 0.58013(13) 0.0608(13) Uani 1 1 d . . . H4A H 0.1884 -0.2280 0.5959 0.073 Uiso 1 1 calc R . . H4B H 0.2462 -0.2052 0.5646 0.073 Uiso 1 1 calc R . . C5 C 0.1290(3) -0.0964(4) 0.55739(13) 0.0594(12) Uani 1 1 d . . . H5A H 0.0849 -0.0706 0.5728 0.071 Uiso 1 1 calc R . . H5B H 0.1011 -0.1634 0.5401 0.071 Uiso 1 1 calc R . . C6 C 0.1546(3) 0.0302(4) 0.53687(11) 0.0450(10) Uani 1 1 d . . . H6A H 0.1953 0.0039 0.5201 0.054 Uiso 1 1 calc R . . H6B H 0.1009 0.0693 0.5230 0.054 Uiso 1 1 calc R . . C7 C 0.1994(3) 0.1344(3) 0.56294(9) 0.0347(8) Uani 1 1 d . . . C8 C 0.1940(2) 0.2733(3) 0.56041(9) 0.0331(8) Uani 1 1 d . . . C9 C 0.1524(3) 0.3558(4) 0.52928(10) 0.0348(8) Uani 1 1 d . . . C10 C 0.1474(3) 0.4973(4) 0.53073(10) 0.0425(9) Uani 1 1 d . . . H10 H 0.1648 0.5431 0.5524 0.051 Uiso 1 1 calc R . . C11 C 0.1166(3) 0.5693(4) 0.49975(11) 0.0491(10) Uani 1 1 d . . . H11 H 0.1152 0.6643 0.5002 0.059 Uiso 1 1 calc R . . C12 C 0.0881(3) 0.5001(5) 0.46832(11) 0.0496(11) Uani 1 1 d . . . H12 H 0.0671 0.5463 0.4470 0.060 Uiso 1 1 calc R . . C13 C 0.0915(3) 0.3608(4) 0.46937(11) 0.0492(10) Uani 1 1 d . . . H13 H 0.0698 0.3137 0.4483 0.059 Uiso 1 1 calc R . . C14 C 0.3172(3) 0.1693(4) 0.65758(10) 0.0347(8) Uani 1 1 d . . . C15 C 0.3831(3) 0.0861(4) 0.67580(11) 0.0430(9) Uani 1 1 d . . . H15 H 0.4273 0.0488 0.6637 0.052 Uiso 1 1 calc R . . C16 C 0.3835(3) 0.0585(5) 0.71181(11) 0.0511(11) Uani 1 1 d . . . H16 H 0.4269 0.0010 0.7242 0.061 Uiso 1 1 calc R . . C17 C 0.3187(3) 0.1173(5) 0.72920(11) 0.0556(12) Uani 1 1 d . . . H17 H 0.3166 0.0983 0.7534 0.067 Uiso 1 1 calc R . . C18 C 0.2569(3) 0.2046(5) 0.71047(11) 0.0506(11) Uani 1 1 d . . . H18 H 0.2147 0.2471 0.7227 0.061 Uiso 1 1 calc R . . C19 C 0.3241(2) 0.4796(3) 0.59774(10) 0.0351(8) Uani 1 1 d . . . C20 C 0.3632(3) 0.4910(4) 0.56641(11) 0.0453(10) Uani 1 1 d . . . H20 H 0.3467 0.4309 0.5473 0.054 Uiso 1 1 calc R . . C21 C 0.4267(3) 0.5916(5) 0.56349(15) 0.0604(13) Uani 1 1 d . . . H21 H 0.4514 0.6010 0.5422 0.072 Uiso 1 1 calc R . . C22 C 0.4530(3) 0.6772(5) 0.59204(18) 0.0704(16) Uani 1 1 d . . . H22 H 0.4966 0.7433 0.5902 0.084 Uiso 1 1 calc R . . C23 C 0.4157(4) 0.6669(4) 0.62338(16) 0.0662(15) Uani 1 1 d . . . H23 H 0.4346 0.7249 0.6427 0.079 Uiso 1 1 calc R . . C24 C 0.3495(3) 0.5692(4) 0.62616(12) 0.0483(10) Uani 1 1 d . . . H24 H 0.3225 0.5641 0.6470 0.058 Uiso 1 1 calc R . . C30 C 0.1056(4) 0.7787(6) 0.68319(16) 0.0833(17) Uani 1 1 d . . . H30A H 0.0864 0.6899 0.6734 0.100 Uiso 1 1 calc R . . H30B H 0.0858 0.7872 0.7067 0.100 Uiso 1 1 calc R . . N1 N 0.2554(2) 0.2306(3) 0.67518(8) 0.0358(7) Uani 1 1 d . . . N2 N 0.1237(2) 0.2879(3) 0.49825(9) 0.0457(8) Uani 1 1 d . . . P1 P 0.24544(7) 0.34491(9) 0.60331(2) 0.0314(2) Uani 1 1 d . . . Cl1 Cl 0.07740(8) 0.38532(11) 0.69571(3) 0.0511(3) Uani 1 1 d . . . Cl2 Cl 0.07186(7) 0.52246(10) 0.61397(3) 0.0487(3) Uani 1 1 d . . . Cl3 Cl 0.22246(13) 0.7867(2) 0.68875(5) 0.1132(6) Uani 1 1 d . . . Cl4 Cl 0.0542(2) 0.9031(3) 0.65512(7) 0.1753(13) Uani 1 1 d . . . Pd1 Pd 0.164109(19) 0.36856(3) 0.647793(7) 0.03254(10) Uani 1 1 d . . . C40 C 0.5000 0.6020(15) 0.7500 0.190(12) Uani 1 2 d S . . Cl40 Cl 0.40839(18) 0.5013(3) 0.73209(7) 0.1577(10) Uani 1 1 d . . . H1 H 0.373(3) 0.197(4) 0.6103(10) 0.041(11) Uiso 1 1 d . . . H2 H 0.298(3) -0.081(4) 0.6219(12) 0.053(13) Uiso 1 1 d . . . H40 H 0.478(4) 0.624(5) 0.7631(15) 0.060(18) 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 C1 0.046(3) 0.0339(18) 0.034(2) 0.0007(15) 0.0078(17) 0.0081(16) C2 0.039(2) 0.0366(18) 0.031(2) -0.0005(14) 0.0097(15) 0.0047(16) C3 0.054(3) 0.040(2) 0.044(3) 0.0002(18) 0.002(2) 0.0074(18) C4 0.087(4) 0.029(2) 0.066(3) -0.0024(19) 0.007(3) 0.000(2) C5 0.072(4) 0.039(2) 0.067(3) -0.008(2) 0.008(2) -0.010(2) C6 0.045(3) 0.040(2) 0.048(2) -0.0098(17) -0.0003(18) -0.0028(17) C7 0.038(2) 0.0363(18) 0.031(2) -0.0054(14) 0.0089(15) -0.0006(15) C8 0.035(2) 0.0365(18) 0.0282(19) -0.0030(14) 0.0063(15) -0.0025(15) C9 0.034(2) 0.0404(19) 0.029(2) -0.0026(14) 0.0025(15) -0.0015(15) C10 0.050(3) 0.042(2) 0.034(2) -0.0023(16) -0.0005(17) 0.0032(17) C11 0.053(3) 0.045(2) 0.048(3) 0.0066(18) 0.002(2) 0.0080(19) C12 0.047(3) 0.068(3) 0.032(2) 0.0070(19) 0.0002(18) 0.008(2) C13 0.052(3) 0.063(3) 0.030(2) -0.0042(18) -0.0022(18) 0.002(2) C14 0.034(2) 0.0378(18) 0.033(2) -0.0005(14) 0.0044(15) 0.0039(15) C15 0.032(2) 0.053(2) 0.044(2) 0.0027(18) 0.0055(17) 0.0132(17) C16 0.046(3) 0.063(3) 0.042(3) 0.0079(19) -0.0013(19) 0.018(2) C17 0.065(3) 0.073(3) 0.027(2) 0.0076(19) 0.0015(19) 0.022(2) C18 0.055(3) 0.067(3) 0.030(2) 0.0026(18) 0.0059(18) 0.020(2) C19 0.031(2) 0.0320(18) 0.040(2) 0.0019(15) -0.0024(16) 0.0018(14) C20 0.045(3) 0.045(2) 0.046(2) 0.0031(17) 0.0051(18) -0.0016(18) C21 0.043(3) 0.059(3) 0.080(4) 0.019(2) 0.012(2) -0.005(2) C22 0.046(3) 0.050(3) 0.109(5) 0.020(3) -0.010(3) -0.011(2) C23 0.063(4) 0.040(2) 0.087(4) -0.009(2) -0.018(3) -0.006(2) C24 0.048(3) 0.043(2) 0.050(3) -0.0035(18) -0.0039(19) 0.0014(18) C30 0.092(5) 0.082(4) 0.075(4) -0.002(3) 0.012(3) 0.010(3) N1 0.0331(19) 0.0424(17) 0.0308(17) 0.0001(13) 0.0009(12) 0.0097(13) N2 0.054(2) 0.0484(19) 0.0322(19) -0.0032(14) -0.0024(15) 0.0001(15) P1 0.0353(6) 0.0309(4) 0.0275(5) -0.0015(3) 0.0028(4) 0.0017(4) Cl1 0.0478(7) 0.0665(7) 0.0415(6) 0.0040(5) 0.0143(4) 0.0205(5) Cl2 0.0531(7) 0.0491(5) 0.0417(6) 0.0041(4) -0.0003(4) 0.0170(5) Cl3 0.1016(15) 0.1479(17) 0.0917(13) 0.0250(11) 0.0199(10) -0.0238(12) Cl4 0.209(3) 0.192(2) 0.1333(19) 0.0725(18) 0.0534(18) 0.124(2) Pd1 0.03256(19) 0.03569(15) 0.02830(16) -0.00273(11) 0.00086(11) 0.00485(11) C40 0.30(3) 0.077(9) 0.23(2) 0.000 0.19(2) 0.000 Cl40 0.144(2) 0.207(3) 0.1203(19) 0.0109(18) 0.0143(15) -0.0332(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 C1 C14 1.490(5) . ? C1 C2 1.513(5) . ? C1 P1 1.830(4) . ? C2 C3 1.344(5) . ? C2 C7 1.469(5) . ? C3 C4 1.485(6) . ? C4 C5 1.499(6) . ? C5 C6 1.535(6) . ? C6 C7 1.500(5) . ? C7 C8 1.364(5) . ? C8 C9 1.477(5) . ? C8 P1 1.815(4) . ? C9 N2 1.352(4) . ? C9 C10 1.388(5) . ? C10 C11 1.376(5) . ? C11 C12 1.370(6) . ? C12 C13 1.364(6) . ? C13 N2 1.324(5) . ? C14 N1 1.351(5) . ? C14 C15 1.381(5) . ? C15 C16 1.372(6) . ? C16 C17 1.371(6) . ? C17 C18 1.375(5) . ? C18 N1 1.340(5) . ? C19 C24 1.387(5) . ? C19 C20 1.388(5) . ? C19 P1 1.800(4) . ? C20 C21 1.384(6) . ? C21 C22 1.368(7) . ? C22 C23 1.373(8) . ? C23 C24 1.392(7) . ? C30 Cl4 1.714(6) . ? C30 Cl3 1.735(6) . ? N1 Pd1 2.082(3) . ? P1 Pd1 2.2124(10) . ? Cl1 Pd1 2.3666(11) . ? Cl2 Pd1 2.2950(11) . ? C40 Cl40 1.742(9) . ? C40 Cl40 1.742(9) 2_656 ? 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 C14 C1 C2 115.4(3) . . ? C14 C1 P1 111.7(3) . . ? C2 C1 P1 102.9(3) . . ? C3 C2 C7 122.8(4) . . ? C3 C2 C1 124.3(4) . . ? C7 C2 C1 112.8(3) . . ? C2 C3 C4 122.9(4) . . ? C3 C4 C5 111.0(3) . . ? C4 C5 C6 112.3(4) . . ? C7 C6 C5 110.2(3) . . ? C8 C7 C2 116.3(3) . . ? C8 C7 C6 128.0(3) . . ? C2 C7 C6 115.7(3) . . ? C7 C8 C9 127.8(3) . . ? C7 C8 P1 108.1(3) . . ? C9 C8 P1 124.1(3) . . ? N2 C9 C10 120.8(3) . . ? N2 C9 C8 116.9(3) . . ? C10 C9 C8 122.2(3) . . ? C11 C10 C9 119.4(4) . . ? C12 C11 C10 119.5(4) . . ? C13 C12 C11 117.6(4) . . ? N2 C13 C12 124.7(4) . . ? N1 C14 C15 120.9(3) . . ? N1 C14 C1 117.5(3) . . ? C15 C14 C1 121.5(3) . . ? C16 C15 C14 120.0(4) . . ? C17 C16 C15 118.7(4) . . ? C16 C17 C18 119.4(4) . . ? N1 C18 C17 122.1(4) . . ? C24 C19 C20 119.5(4) . . ? C24 C19 P1 119.1(3) . . ? C20 C19 P1 121.4(3) . . ? C21 C20 C19 120.2(4) . . ? C22 C21 C20 119.8(5) . . ? C21 C22 C23 120.9(5) . . ? C22 C23 C24 119.8(5) . . ? C19 C24 C23 119.7(4) . . ? Cl4 C30 Cl3 113.4(4) . . ? C18 N1 C14 118.8(3) . . ? C18 N1 Pd1 121.4(3) . . ? C14 N1 Pd1 119.7(2) . . ? C13 N2 C9 117.8(3) . . ? C19 P1 C8 112.43(17) . . ? C19 P1 C1 108.95(19) . . ? C8 P1 C1 94.18(17) . . ? C19 P1 Pd1 116.88(13) . . ? C8 P1 Pd1 119.63(13) . . ? C1 P1 Pd1 100.54(13) . . ? N1 Pd1 P1 84.66(9) . . ? N1 Pd1 Cl2 175.02(9) . . ? P1 Pd1 Cl2 90.48(4) . . ? N1 Pd1 Cl1 93.85(9) . . ? P1 Pd1 Cl1 177.96(4) . . ? Cl2 Pd1 Cl1 91.04(4) . . ? Cl40 C40 Cl40 111.1(8) . 2_656 ? _diffrn_measured_fraction_theta_max 0.829 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.829 _refine_diff_density_max 0.562 _refine_diff_density_min -0.759 _refine_diff_density_rms 0.074 #====END ############################################################################## data_compound_2a' _database_code_CSD 208511 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H29 Cl4 N2 P Pd' _chemical_formula_weight 636.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.7170(2) _cell_length_b 16.2360(3) _cell_length_c 18.9070(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2675.89(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.580 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 1.170 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method none _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 3452 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3452 _reflns_number_gt 3351 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.0462P)^2^+3.7698P] 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 SHELXL _refine_ls_extinction_coef 0.0125(9) _refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.47(4) _refine_ls_number_reflns 3452 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0350 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0872 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _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 C1 C 0.3090(5) 0.0085(3) 0.2505(2) 0.0210(8) Uani 1 1 d . . . H1 H 0.3553 -0.0385 0.2749 0.025 Uiso 1 1 calc R . . C2 C 0.1438(5) -0.0130(3) 0.2310(3) 0.0234(9) Uani 1 1 d . . . C3 C 0.1035(7) -0.0730(4) 0.1859(3) 0.0390(13) Uani 1 1 d . . . H3 H 0.1802 -0.1003 0.1611 0.047 Uiso 1 1 calc R . . C4 C -0.0604(6) -0.0977(4) 0.1739(4) 0.0438(15) Uani 1 1 d . . . H4A H -0.0663 -0.1571 0.1689 0.053 Uiso 1 1 calc R . . H4B H -0.0971 -0.0731 0.1304 0.053 Uiso 1 1 calc R . . C5 C -0.1623(6) -0.0706(3) 0.2349(3) 0.0358(11) Uani 1 1 d . . . H5A H -0.1389 -0.1032 0.2766 0.043 Uiso 1 1 calc R . . H5B H -0.2690 -0.0799 0.2227 0.043 Uiso 1 1 calc R . . C6 C -0.1376(5) 0.0206(3) 0.2514(3) 0.0294(10) Uani 1 1 d . . . H6A H -0.1700 0.0536 0.2113 0.035 Uiso 1 1 calc R . . H6B H -0.1997 0.0362 0.2918 0.035 Uiso 1 1 calc R . . C7 C 0.0294(5) 0.0376(3) 0.2672(2) 0.0221(8) Uani 1 1 d . . . C8 C 0.0843(5) 0.0949(3) 0.3129(2) 0.0199(8) Uani 1 1 d . . . C9 C -0.0042(5) 0.1521(3) 0.3573(2) 0.0221(9) Uani 1 1 d . . . C10 C -0.1377(5) 0.1911(3) 0.3329(2) 0.0253(9) Uani 1 1 d . . . H10 H -0.1698 0.1844 0.2863 0.030 Uiso 1 1 calc R . . C11 C -0.2211(6) 0.2399(3) 0.3795(3) 0.0288(10) Uani 1 1 d . . . H11 H -0.3113 0.2654 0.3650 0.035 Uiso 1 1 calc R . . C12 C -0.1676(6) 0.2499(3) 0.4477(3) 0.0306(11) Uani 1 1 d . . . H12 H -0.2215 0.2818 0.4802 0.037 Uiso 1 1 calc R . . C13 C -0.0325(6) 0.2116(3) 0.4665(3) 0.0321(11) Uani 1 1 d . . . H13 H 0.0048 0.2206 0.5120 0.039 Uiso 1 1 calc R . . C14 C 0.4082(5) 0.0316(3) 0.1886(2) 0.0214(8) Uani 1 1 d . . . C15 C 0.4611(6) -0.0276(3) 0.1423(3) 0.0279(10) Uani 1 1 d . . . H15 H 0.4413 -0.0830 0.1511 0.033 Uiso 1 1 calc R . . C16 C 0.5437(6) -0.0050(3) 0.0826(3) 0.0304(10) Uani 1 1 d . . . H16 H 0.5799 -0.0447 0.0513 0.036 Uiso 1 1 calc R . . C17 C 0.5712(6) 0.0783(3) 0.0706(3) 0.0310(11) Uani 1 1 d . . . H17 H 0.6210 0.0955 0.0297 0.037 Uiso 1 1 calc R . . C18 C 0.5232(6) 0.1351(3) 0.1206(2) 0.0273(10) Uani 1 1 d . . . H18 H 0.5454 0.1905 0.1135 0.033 Uiso 1 1 calc R . . C19 C 0.3700(5) 0.0636(3) 0.3977(2) 0.0218(9) Uani 1 1 d . . . H19 H 0.3600 0.1106 0.4299 0.026 Uiso 1 1 calc R . . C20 C 0.2860(6) -0.0098(3) 0.4318(3) 0.0276(10) Uani 1 1 d . . . H20A H 0.1782 0.0034 0.4376 0.033 Uiso 1 1 calc R . . H20B H 0.2939 -0.0576 0.4013 0.033 Uiso 1 1 calc R . . C21 C 0.3574(6) -0.0290(4) 0.5040(3) 0.0348(11) Uani 1 1 d . . . H21A H 0.3065 -0.0763 0.5246 0.042 Uiso 1 1 calc R . . H21B H 0.3427 0.0176 0.5354 0.042 Uiso 1 1 calc R . . C22 C 0.5300(7) -0.0470(4) 0.4963(3) 0.0415(13) Uani 1 1 d . . . H22A H 0.5739 -0.0570 0.5427 0.050 Uiso 1 1 calc R . . H22B H 0.5441 -0.0962 0.4681 0.050 Uiso 1 1 calc R . . C23 C 0.6122(6) 0.0245(4) 0.4616(3) 0.0383(12) Uani 1 1 d . . . H23A H 0.7196 0.0106 0.4554 0.046 Uiso 1 1 calc R . . H23B H 0.6065 0.0724 0.4922 0.046 Uiso 1 1 calc R . . C24 C 0.5414(6) 0.0455(3) 0.3895(3) 0.0281(10) Uani 1 1 d . . . H24A H 0.5927 0.0932 0.3696 0.034 Uiso 1 1 calc R . . H24B H 0.5556 -0.0004 0.3573 0.034 Uiso 1 1 calc R . . C25 C 0.4161(10) 0.2148(6) -0.1223(4) 0.070(2) Uani 1 1 d . . . H25A H 0.4537 0.1586 -0.1241 0.085 Uiso 1 1 calc R . . H25B H 0.3338 0.2196 -0.1566 0.085 Uiso 1 1 calc R . . N1 N 0.4458(4) 0.1129(2) 0.1790(2) 0.0222(8) Uani 1 1 d . . . N2 N 0.0485(5) 0.1626(3) 0.4238(2) 0.0259(8) Uani 1 1 d . . . P1 P 0.29099(12) 0.09449(7) 0.31289(6) 0.0179(2) Uani 1 1 d . . . Cl1 Cl 0.54867(16) 0.30741(7) 0.20613(6) 0.0346(3) Uani 1 1 d . . . Cl2 Cl 0.36372(12) 0.27325(6) 0.35949(5) 0.0222(2) Uani 1 1 d . . . Cl3 Cl 0.3416(3) 0.23327(11) -0.03818(10) 0.0607(5) Uani 1 1 d . . . Cl4 Cl 0.5629(4) 0.28044(18) -0.14661(14) 0.0958(9) Uani 1 1 d . . . Pd1 Pd 0.40878(4) 0.196796(19) 0.260119(16) 0.01844(11) 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 C1 0.0179(18) 0.0206(18) 0.025(2) -0.0007(17) 0.0014(17) 0.0002(15) C2 0.0189(19) 0.023(2) 0.028(2) -0.0039(18) 0.0045(18) -0.0019(16) C3 0.028(2) 0.041(3) 0.048(3) -0.023(2) 0.010(3) -0.007(2) C4 0.027(3) 0.046(3) 0.059(4) -0.027(3) 0.004(3) -0.009(2) C5 0.022(2) 0.037(3) 0.049(3) -0.010(2) 0.002(2) -0.008(2) C6 0.0193(19) 0.035(2) 0.034(3) -0.009(2) 0.0001(19) -0.0023(18) C7 0.0185(18) 0.024(2) 0.024(2) 0.0002(17) 0.0010(17) 0.0040(17) C8 0.0185(18) 0.0225(19) 0.0187(17) 0.0022(15) -0.0004(17) 0.0016(17) C9 0.019(2) 0.024(2) 0.023(2) -0.0044(17) 0.0030(16) 0.0004(17) C10 0.025(2) 0.022(2) 0.029(2) -0.0040(19) -0.0018(17) 0.0009(19) C11 0.019(2) 0.027(2) 0.040(3) -0.007(2) -0.001(2) 0.0045(19) C12 0.020(2) 0.035(3) 0.037(3) -0.014(2) 0.006(2) 0.000(2) C13 0.024(2) 0.048(3) 0.024(2) -0.011(2) 0.0045(18) -0.001(2) C14 0.0185(18) 0.0232(19) 0.0226(18) -0.0024(16) 0.0013(18) -0.0017(18) C15 0.022(2) 0.026(2) 0.035(2) -0.008(2) 0.007(2) -0.0036(19) C16 0.027(2) 0.032(2) 0.033(2) -0.010(2) 0.008(2) 0.001(2) C17 0.032(3) 0.033(3) 0.028(2) -0.0041(19) 0.010(2) -0.001(2) C18 0.032(2) 0.030(2) 0.020(2) -0.0028(18) 0.0054(19) -0.005(2) C19 0.022(2) 0.022(2) 0.0215(19) -0.0011(16) 0.0003(17) 0.0021(17) C20 0.023(2) 0.029(2) 0.031(2) 0.0073(19) -0.0008(19) -0.0032(19) C21 0.037(3) 0.036(3) 0.031(2) 0.011(2) -0.001(2) -0.002(2) C22 0.036(3) 0.047(3) 0.041(3) 0.019(3) -0.009(3) 0.005(3) C23 0.025(2) 0.050(3) 0.040(3) 0.012(2) -0.010(2) -0.002(2) C24 0.019(2) 0.033(2) 0.032(2) 0.008(2) -0.0021(19) 0.0012(19) C25 0.051(4) 0.096(6) 0.065(4) -0.014(4) 0.000(4) -0.008(5) N1 0.0217(18) 0.0208(17) 0.0242(17) -0.0030(14) 0.0013(15) -0.0012(14) N2 0.0203(18) 0.034(2) 0.0235(18) -0.0059(16) -0.0001(15) 0.0013(16) P1 0.0164(5) 0.0181(5) 0.0192(5) -0.0004(4) 0.0003(4) -0.0002(4) Cl1 0.0483(7) 0.0216(5) 0.0340(5) -0.0022(5) 0.0137(5) -0.0097(5) Cl2 0.0245(5) 0.0206(5) 0.0216(4) -0.0033(4) -0.0001(4) 0.0020(4) Cl3 0.0756(12) 0.0508(9) 0.0557(9) 0.0055(8) -0.0036(9) -0.0036(9) Cl4 0.107(2) 0.0965(17) 0.0836(15) -0.0008(13) 0.0172(15) -0.0450(17) Pd1 0.01921(16) 0.01673(16) 0.01937(16) -0.00042(11) 0.00013(11) -0.00029(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C14 1.502(6) . ? C1 C2 1.527(6) . ? C1 P1 1.835(4) . ? C2 C3 1.340(7) . ? C2 C7 1.462(6) . ? C3 C4 1.501(7) . ? C4 C5 1.521(8) . ? C5 C6 1.529(7) . ? C6 C7 1.512(6) . ? C7 C8 1.357(6) . ? C8 C9 1.470(6) . ? C8 P1 1.802(5) . ? C9 N2 1.351(6) . ? C9 C10 1.402(6) . ? C10 C11 1.391(7) . ? C11 C12 1.380(7) . ? C12 C13 1.379(7) . ? C13 N2 1.335(6) . ? C14 N1 1.372(6) . ? C14 C15 1.380(6) . ? C15 C16 1.388(7) . ? C16 C17 1.393(7) . ? C17 C18 1.385(7) . ? C18 N1 1.343(6) . ? C19 C24 1.530(6) . ? C19 C20 1.540(6) . ? C19 P1 1.815(5) . ? C20 C21 1.532(7) . ? C21 C22 1.539(8) . ? C22 C23 1.514(8) . ? C23 C24 1.536(7) . ? C25 Cl4 1.727(9) . ? C25 Cl3 1.744(8) . ? N1 Pd1 2.076(4) . ? P1 Pd1 2.1929(11) . ? Cl1 Pd1 2.3987(12) . ? Cl2 Pd1 2.2858(11) . ? 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 C14 C1 C2 114.3(4) . . ? C14 C1 P1 111.1(3) . . ? C2 C1 P1 104.4(3) . . ? C3 C2 C7 121.8(4) . . ? C3 C2 C1 124.5(4) . . ? C7 C2 C1 113.7(4) . . ? C2 C3 C4 122.7(5) . . ? C3 C4 C5 111.3(5) . . ? C4 C5 C6 110.6(5) . . ? C7 C6 C5 110.6(4) . . ? C8 C7 C2 116.3(4) . . ? C8 C7 C6 126.1(4) . . ? C2 C7 C6 117.5(4) . . ? C7 C8 C9 127.7(4) . . ? C7 C8 P1 110.5(3) . . ? C9 C8 P1 121.8(3) . . ? N2 C9 C10 122.1(4) . . ? N2 C9 C8 115.7(4) . . ? C10 C9 C8 122.2(4) . . ? C11 C10 C9 118.8(4) . . ? C12 C11 C10 118.9(5) . . ? C13 C12 C11 118.5(5) . . ? N2 C13 C12 124.3(5) . . ? N1 C14 C15 120.4(4) . . ? N1 C14 C1 118.7(4) . . ? C15 C14 C1 120.8(4) . . ? C14 C15 C16 120.4(5) . . ? C15 C16 C17 118.6(4) . . ? C18 C17 C16 118.9(5) . . ? N1 C18 C17 122.3(5) . . ? C24 C19 C20 111.0(4) . . ? C24 C19 P1 109.5(3) . . ? C20 C19 P1 113.8(3) . . ? C21 C20 C19 109.7(4) . . ? C20 C21 C22 110.6(5) . . ? C23 C22 C21 111.0(5) . . ? C22 C23 C24 111.4(5) . . ? C19 C24 C23 110.2(4) . . ? Cl4 C25 Cl3 114.4(5) . . ? C18 N1 C14 119.1(4) . . ? C18 N1 Pd1 120.6(3) . . ? C14 N1 Pd1 119.8(3) . . ? C13 N2 C9 117.3(4) . . ? C8 P1 C19 112.4(2) . . ? C8 P1 C1 95.1(2) . . ? C19 P1 C1 109.0(2) . . ? C8 P1 Pd1 117.72(15) . . ? C19 P1 Pd1 115.67(15) . . ? C1 P1 Pd1 104.10(14) . . ? N1 Pd1 P1 84.95(11) . . ? N1 Pd1 Cl2 171.91(11) . . ? P1 Pd1 Cl2 87.53(4) . . ? N1 Pd1 Cl1 95.61(11) . . ? P1 Pd1 Cl1 177.10(5) . . ? Cl2 Pd1 Cl1 91.75(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 C14 C1 C2 C3 58.2(7) . . . . ? P1 C1 C2 C3 179.8(5) . . . . ? C14 C1 C2 C7 -122.8(4) . . . . ? P1 C1 C2 C7 -1.2(5) . . . . ? C7 C2 C3 C4 -5.4(9) . . . . ? C1 C2 C3 C4 173.5(6) . . . . ? C2 C3 C4 C5 -20.3(9) . . . . ? C3 C4 C5 C6 50.7(7) . . . . ? C4 C5 C6 C7 -56.4(6) . . . . ? C3 C2 C7 C8 178.4(5) . . . . ? C1 C2 C7 C8 -0.7(6) . . . . ? C3 C2 C7 C6 -0.8(7) . . . . ? C1 C2 C7 C6 -179.8(4) . . . . ? C5 C6 C7 C8 -147.3(5) . . . . ? C5 C6 C7 C2 31.7(6) . . . . ? C2 C7 C8 C9 -178.3(4) . . . . ? C6 C7 C8 C9 0.7(8) . . . . ? C2 C7 C8 P1 2.3(5) . . . . ? C6 C7 C8 P1 -178.7(4) . . . . ? C7 C8 C9 N2 138.6(5) . . . . ? P1 C8 C9 N2 -42.1(5) . . . . ? C7 C8 C9 C10 -39.4(7) . . . . ? P1 C8 C9 C10 139.9(4) . . . . ? N2 C9 C10 C11 -2.2(7) . . . . ? C8 C9 C10 C11 175.6(4) . . . . ? C9 C10 C11 C12 1.6(7) . . . . ? C10 C11 C12 C13 0.7(8) . . . . ? C11 C12 C13 N2 -2.5(8) . . . . ? C2 C1 C14 N1 105.6(5) . . . . ? P1 C1 C14 N1 -12.2(5) . . . . ? C2 C1 C14 C15 -74.6(6) . . . . ? P1 C1 C14 C15 167.6(4) . . . . ? N1 C14 C15 C16 -4.7(8) . . . . ? C1 C14 C15 C16 175.5(4) . . . . ? C14 C15 C16 C17 -0.2(8) . . . . ? C15 C16 C17 C18 3.8(8) . . . . ? C16 C17 C18 N1 -2.6(8) . . . . ? C24 C19 C20 C21 58.0(5) . . . . ? P1 C19 C20 C21 -178.0(3) . . . . ? C19 C20 C21 C22 -57.3(6) . . . . ? C20 C21 C22 C23 57.0(7) . . . . ? C21 C22 C23 C24 -56.3(7) . . . . ? C20 C19 C24 C23 -57.1(5) . . . . ? P1 C19 C24 C23 176.5(4) . . . . ? C22 C23 C24 C19 56.3(6) . . . . ? C17 C18 N1 C14 -2.2(7) . . . . ? C17 C18 N1 Pd1 169.6(4) . . . . ? C15 C14 N1 C18 5.9(7) . . . . ? C1 C14 N1 C18 -174.3(4) . . . . ? C15 C14 N1 Pd1 -166.0(4) . . . . ? C1 C14 N1 Pd1 13.8(6) . . . . ? C12 C13 N2 C9 1.9(8) . . . . ? C10 C9 N2 C13 0.5(7) . . . . ? C8 C9 N2 C13 -177.5(4) . . . . ? C7 C8 P1 C19 -115.5(3) . . . . ? C9 C8 P1 C19 65.1(4) . . . . ? C7 C8 P1 C1 -2.6(4) . . . . ? C9 C8 P1 C1 178.0(4) . . . . ? C7 C8 P1 Pd1 106.3(3) . . . . ? C9 C8 P1 Pd1 -73.1(4) . . . . ? C24 C19 P1 C8 167.1(3) . . . . ? C20 C19 P1 C8 42.3(4) . . . . ? C24 C19 P1 C1 63.1(4) . . . . ? C20 C19 P1 C1 -61.7(4) . . . . ? C24 C19 P1 Pd1 -53.8(4) . . . . ? C20 C19 P1 Pd1 -178.6(3) . . . . ? C14 C1 P1 C8 125.7(3) . . . . ? C2 C1 P1 C8 2.0(3) . . . . ? C14 C1 P1 C19 -118.5(3) . . . . ? C2 C1 P1 C19 117.8(3) . . . . ? C14 C1 P1 Pd1 5.5(3) . . . . ? C2 C1 P1 Pd1 -118.2(3) . . . . ? C18 N1 Pd1 P1 -179.4(4) . . . . ? C14 N1 Pd1 P1 -7.7(3) . . . . ? C18 N1 Pd1 Cl2 -157.5(6) . . . . ? C14 N1 Pd1 Cl2 14.2(11) . . . . ? C18 N1 Pd1 Cl1 -2.3(4) . . . . ? C14 N1 Pd1 Cl1 169.5(3) . . . . ? C8 P1 Pd1 N1 -103.0(2) . . . . ? C19 P1 Pd1 N1 120.10(19) . . . . ? C1 P1 Pd1 N1 0.56(18) . . . . ? C8 P1 Pd1 Cl2 79.97(17) . . . . ? C19 P1 Pd1 Cl2 -56.89(17) . . . . ? C1 P1 Pd1 Cl2 -176.43(15) . . . . ? C8 P1 Pd1 Cl1 155.7(8) . . . . ? C19 P1 Pd1 Cl1 18.8(9) . . . . ? C1 P1 Pd1 Cl1 -100.7(9) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.697 _refine_diff_density_min -0.862 _refine_diff_density_rms 0.095 #====END ############################################################################## data_compound_2b _database_code_CSD 208512 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H44 Cl4 N2 P2 Pd2' _chemical_formula_weight 1089.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'I 2/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 21.587(5) _cell_length_b 8.979(5) _cell_length_c 26.183(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.844(5) _cell_angle_gamma 90.00 _cell_volume 4906(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2192 _exptl_absorpt_coefficient_mu 1.051 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method none _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 4831 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0864 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.41 _reflns_number_total 4831 _reflns_number_gt 3352 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The low quality of crystal of 2b led to rather high R values and, consequently, to a large residual electron density peak. However, this residual electron density peak is not located close to the molecule of 2b. In spite of the rather high R factor, this X-ray structure shows unambiguously the cis-configuration of the 2-phospholene moiety, that is the crucial point for our study. 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^)+(0.2000P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0034(9) _refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4831 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1919 _refine_ls_R_factor_gt 0.1582 _refine_ls_wR_factor_ref 0.4475 _refine_ls_wR_factor_gt 0.4315 _refine_ls_goodness_of_fit_ref 1.697 _refine_ls_restrained_S_all 1.697 _refine_ls_shift/su_max 0.052 _refine_ls_shift/su_mean 0.010 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 Pd1 Pd 0.90134(5) -0.01054(10) 0.11318(4) 0.0374(5) Uani 1 1 d . . . Cl1 Cl 0.9621(2) -0.1712(4) 0.07179(19) 0.0602(12) Uani 1 1 d . . . Cl2 Cl 0.85110(19) -0.2116(4) 0.14180(16) 0.0495(10) Uani 1 1 d . . . P1 P 0.84159(18) 0.1384(4) 0.14604(15) 0.0389(9) Uani 1 1 d . . . N8 N 0.9432(6) 0.1853(12) 0.0937(4) 0.037(3) Uani 1 1 d . . . C1 C 0.8752(8) 0.3235(14) 0.1405(5) 0.044(3) Uani 1 1 d . . . H1 H 0.8398 0.3913 0.1251 0.052 Uiso 1 1 calc R . . C2 C 0.9056(7) 0.3739(14) 0.1973(5) 0.038(3) Uani 1 1 d . . . C3 C 0.9416(10) 0.4924(14) 0.2126(8) 0.053(5) Uani 1 1 d . . . H3 H 0.9548 0.5485 0.1874 0.063 Uiso 1 1 calc R . . C4 C 0.9619(10) 0.539(2) 0.2691(8) 0.071(5) Uani 1 1 d . . . H4A H 0.9601 0.6469 0.2710 0.085 Uiso 1 1 calc R . . H4B H 1.0061 0.5092 0.2838 0.085 Uiso 1 1 calc R . . C5 C 0.9218(9) 0.4747(15) 0.3018(7) 0.051(4) Uani 1 1 d . . . H5A H 0.8800 0.5218 0.2926 0.061 Uiso 1 1 calc R . . H5B H 0.9415 0.4948 0.3388 0.061 Uiso 1 1 calc R . . C6 C 0.9140(8) 0.3094(16) 0.2935(6) 0.056(4) Uani 1 1 d . . . H6A H 0.9550 0.2612 0.3078 0.067 Uiso 1 1 calc R . . H6B H 0.8843 0.2724 0.3128 0.067 Uiso 1 1 calc R . . C7 C 0.8900(7) 0.2690(15) 0.2370(6) 0.045(3) Uani 1 1 d . . . C8 C 0.8543(7) 0.1504(15) 0.2164(6) 0.045(3) Uani 1 1 d . . . C9 C 0.8333(8) 0.0356(16) 0.2509(6) 0.043(3) Uani 1 1 d . . . C10 C 0.8774(9) -0.0484(19) 0.2846(7) 0.054(4) Uani 1 1 d . . . H10 H 0.9204 -0.0382 0.2853 0.065 Uiso 1 1 calc R . . C11 C 0.8593(10) -0.151(2) 0.3188(7) 0.072(5) Uani 1 1 d . . . H11 H 0.8898 -0.2109 0.3411 0.086 Uiso 1 1 calc R . . C12 C 0.7945(10) -0.1612(19) 0.3185(7) 0.068(5) Uani 1 1 d . . . H12 H 0.7822 -0.2238 0.3424 0.081 Uiso 1 1 calc R . . C13 C 0.7481(10) -0.0785(19) 0.2827(7) 0.063(5) Uani 1 1 d . . . H13 H 0.7049 -0.0876 0.2818 0.075 Uiso 1 1 calc R . . C14 C 0.7684(10) 0.0192(17) 0.2481(8) 0.056(4) Uani 1 1 d . . . H14 H 0.7383 0.0730 0.2232 0.067 Uiso 1 1 calc R . . C15 C 0.9208(7) 0.3227(14) 0.1050(5) 0.038(3) Uani 1 1 d . . . C16 C 0.9460(10) 0.4435(19) 0.0894(7) 0.063(5) Uani 1 1 d . . . H16 H 0.9304 0.5362 0.0960 0.076 Uiso 1 1 calc R . . C17 C 0.9947(10) 0.4372(19) 0.0638(7) 0.062(5) Uani 1 1 d . . . H17 H 1.0128 0.5239 0.0546 0.074 Uiso 1 1 calc R . . C18 C 1.0138(8) 0.3110(18) 0.0532(6) 0.058(4) Uani 1 1 d . . . H18 H 1.0459 0.3047 0.0355 0.069 Uiso 1 1 calc R . . C19 C 0.9872(8) 0.1793(16) 0.0679(6) 0.045(3) Uani 1 1 d . . . H19 H 1.0013 0.0873 0.0590 0.054 Uiso 1 1 calc R . . C20 C 0.7582(7) 0.1385(16) 0.1122(6) 0.049(4) Uani 1 1 d . . . C21 C 0.7171(8) 0.250(2) 0.1236(7) 0.071(6) Uani 1 1 d . . . H21 H 0.7337 0.3212 0.1492 0.085 Uiso 1 1 calc R . . C22 C 0.6530(10) 0.254(3) 0.0974(8) 0.095(9) Uani 1 1 d . . . H22 H 0.6260 0.3242 0.1065 0.114 Uiso 1 1 calc R . . C23 C 0.6292(10) 0.151(3) 0.0565(8) 0.085(7) Uani 1 1 d . . . H23 H 0.5865 0.1538 0.0371 0.102 Uiso 1 1 calc R . . C24 C 0.6695(14) 0.048(4) 0.0462(12) 0.125(11) Uani 1 1 d . . . H24 H 0.6527 -0.0192 0.0192 0.151 Uiso 1 1 calc R . . C25 C 0.7343(11) 0.033(3) 0.0720(10) 0.081(6) Uani 1 1 d . . . H25 H 0.7599 -0.0407 0.0634 0.097 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 Pd1 0.0413(8) 0.0308(7) 0.0409(8) -0.0015(4) 0.0120(6) -0.0004(4) Cl1 0.077(3) 0.0355(18) 0.080(3) -0.0074(18) 0.041(2) 0.0009(18) Cl2 0.058(2) 0.0285(17) 0.072(3) 0.0051(14) 0.034(2) -0.0057(14) P1 0.040(2) 0.0367(18) 0.040(2) -0.0016(14) 0.0097(17) -0.0020(14) N8 0.039(6) 0.042(6) 0.026(6) -0.002(4) 0.000(5) -0.004(5) C1 0.065(10) 0.021(6) 0.043(8) -0.004(5) 0.012(7) -0.001(6) C2 0.041(8) 0.033(6) 0.038(7) 0.006(5) 0.008(6) 0.003(5) C3 0.067(12) 0.039(8) 0.053(10) -0.008(6) 0.018(9) -0.013(7) C4 0.059(12) 0.089(12) 0.071(13) -0.015(11) 0.026(10) -0.036(10) C5 0.059(11) 0.047(8) 0.047(9) -0.011(7) 0.011(8) -0.007(7) C6 0.066(11) 0.045(8) 0.054(9) -0.010(7) 0.009(8) -0.012(7) C7 0.044(8) 0.046(8) 0.046(8) -0.001(6) 0.012(7) 0.000(6) C8 0.046(9) 0.050(8) 0.038(8) 0.005(6) 0.007(7) 0.009(6) C9 0.048(9) 0.041(7) 0.044(8) -0.003(6) 0.016(7) -0.006(6) C10 0.050(10) 0.060(9) 0.052(10) 0.011(8) 0.012(8) 0.003(8) C11 0.074(13) 0.079(12) 0.056(11) 0.019(9) 0.004(10) -0.007(10) C12 0.096(15) 0.058(10) 0.052(10) 0.003(8) 0.022(11) -0.034(10) C13 0.075(13) 0.060(10) 0.059(11) 0.002(8) 0.028(10) -0.020(9) C14 0.063(12) 0.058(9) 0.050(10) -0.004(7) 0.021(10) -0.004(8) C15 0.043(8) 0.031(6) 0.040(7) -0.001(5) 0.010(6) -0.007(6) C16 0.093(14) 0.051(9) 0.055(10) 0.005(8) 0.036(10) -0.007(9) C17 0.094(14) 0.051(9) 0.049(9) -0.004(7) 0.034(10) -0.022(9) C18 0.068(11) 0.053(9) 0.057(10) 0.003(7) 0.027(9) -0.013(8) C19 0.055(9) 0.033(7) 0.051(9) 0.009(6) 0.021(8) 0.006(6) C20 0.047(9) 0.060(9) 0.041(8) 0.010(7) 0.013(7) -0.006(7) C21 0.048(10) 0.104(14) 0.057(11) -0.025(10) 0.006(9) 0.031(9) C22 0.075(14) 0.16(2) 0.066(13) 0.060(15) 0.043(12) 0.061(15) C23 0.050(12) 0.14(2) 0.054(13) 0.013(13) -0.001(11) -0.022(13) C24 0.071(19) 0.19(3) 0.09(2) 0.01(2) -0.020(17) -0.04(2) C25 0.048(11) 0.123(17) 0.069(14) -0.003(12) 0.010(11) -0.023(11) _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 Pd1 N8 2.099(11) . ? Pd1 P1 2.182(4) . ? Pd1 Cl2 2.327(4) . ? Pd1 Cl1 2.388(4) . ? P1 C20 1.791(16) . ? P1 C8 1.795(15) . ? P1 C1 1.835(14) . ? N8 C19 1.301(19) . ? N8 C15 1.384(18) . ? C1 C15 1.52(2) . ? C1 C2 1.533(19) . ? C2 C3 1.317(19) . ? C2 C7 1.502(19) . ? C3 C4 1.49(3) . ? C4 C5 1.48(2) . ? C5 C6 1.503(19) . ? C6 C7 1.48(2) . ? C7 C8 1.344(19) . ? C8 C9 1.51(2) . ? C9 C10 1.35(2) . ? C9 C14 1.39(2) . ? C10 C11 1.41(2) . ? C11 C12 1.40(3) . ? C12 C13 1.40(3) . ? C13 C14 1.41(2) . ? C15 C16 1.32(2) . ? C16 C17 1.39(3) . ? C17 C18 1.26(2) . ? C18 C19 1.41(2) . ? C20 C25 1.41(3) . ? C20 C21 1.42(2) . ? C21 C22 1.38(3) . ? C22 C23 1.41(3) . ? C23 C24 1.34(4) . ? C24 C25 1.40(3) . ? 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 N8 Pd1 P1 85.2(3) . . ? N8 Pd1 Cl2 173.5(3) . . ? P1 Pd1 Cl2 88.69(14) . . ? N8 Pd1 Cl1 94.3(3) . . ? P1 Pd1 Cl1 176.33(15) . . ? Cl2 Pd1 Cl1 91.90(14) . . ? C20 P1 C8 112.2(7) . . ? C20 P1 C1 109.1(7) . . ? C8 P1 C1 93.8(7) . . ? C20 P1 Pd1 115.2(5) . . ? C8 P1 Pd1 119.4(5) . . ? C1 P1 Pd1 103.8(5) . . ? C19 N8 C15 119.4(12) . . ? C19 N8 Pd1 120.6(9) . . ? C15 N8 Pd1 119.9(10) . . ? C15 C1 C2 114.4(12) . . ? C15 C1 P1 112.1(9) . . ? C2 C1 P1 105.7(9) . . ? C3 C2 C7 121.1(14) . . ? C3 C2 C1 127.2(14) . . ? C7 C2 C1 111.7(11) . . ? C2 C3 C4 121.9(17) . . ? C3 C4 C5 113.3(15) . . ? C4 C5 C6 111.3(16) . . ? C7 C6 C5 112.5(14) . . ? C8 C7 C6 127.7(14) . . ? C8 C7 C2 115.3(13) . . ? C6 C7 C2 117.0(12) . . ? C7 C8 C9 121.9(13) . . ? C7 C8 P1 112.3(12) . . ? C9 C8 P1 125.5(11) . . ? C10 C9 C14 120.4(16) . . ? C10 C9 C8 120.1(15) . . ? C14 C9 C8 119.5(14) . . ? C9 C10 C11 121.3(18) . . ? C12 C11 C10 118.5(17) . . ? C11 C12 C13 120.9(16) . . ? C12 C13 C14 118.3(18) . . ? C9 C14 C13 120.5(18) . . ? C16 C15 N8 118.0(15) . . ? C16 C15 C1 124.6(13) . . ? N8 C15 C1 116.9(11) . . ? C15 C16 C17 122.6(17) . . ? C18 C17 C16 118.3(16) . . ? C17 C18 C19 121.1(17) . . ? N8 C19 C18 120.6(14) . . ? C25 C20 C21 120.0(17) . . ? C25 C20 P1 119.9(15) . . ? C21 C20 P1 120.0(12) . . ? C22 C21 C20 121.2(18) . . ? C21 C22 C23 119(2) . . ? C24 C23 C22 118(2) . . ? C23 C24 C25 126(3) . . ? C24 C25 C20 115(2) . . ? 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 N8 Pd1 P1 C20 113.2(6) . . . . ? Cl2 Pd1 P1 C20 -69.1(5) . . . . ? Cl1 Pd1 P1 C20 30(2) . . . . ? N8 Pd1 P1 C8 -108.6(6) . . . . ? Cl2 Pd1 P1 C8 69.1(6) . . . . ? Cl1 Pd1 P1 C8 168(2) . . . . ? N8 Pd1 P1 C1 -6.1(5) . . . . ? Cl2 Pd1 P1 C1 171.6(5) . . . . ? Cl1 Pd1 P1 C1 -89(2) . . . . ? P1 Pd1 N8 C19 -177.1(11) . . . . ? Cl2 Pd1 N8 C19 162(2) . . . . ? Cl1 Pd1 N8 C19 -0.8(10) . . . . ? P1 Pd1 N8 C15 -1.9(9) . . . . ? Cl2 Pd1 N8 C15 -23(3) . . . . ? Cl1 Pd1 N8 C15 174.5(9) . . . . ? C20 P1 C1 C15 -110.1(11) . . . . ? C8 P1 C1 C15 134.8(11) . . . . ? Pd1 P1 C1 C15 13.2(11) . . . . ? C20 P1 C1 C2 124.7(10) . . . . ? C8 P1 C1 C2 9.6(11) . . . . ? Pd1 P1 C1 C2 -112.0(9) . . . . ? C15 C1 C2 C3 48(2) . . . . ? P1 C1 C2 C3 171.8(15) . . . . ? C15 C1 C2 C7 -131.7(12) . . . . ? P1 C1 C2 C7 -8.0(14) . . . . ? C7 C2 C3 C4 -8(3) . . . . ? C1 C2 C3 C4 172.5(17) . . . . ? C2 C3 C4 C5 -19(3) . . . . ? C3 C4 C5 C6 49(2) . . . . ? C4 C5 C6 C7 -53(2) . . . . ? C5 C6 C7 C8 -150.8(17) . . . . ? C5 C6 C7 C2 28(2) . . . . ? C3 C2 C7 C8 -178.3(16) . . . . ? C1 C2 C7 C8 1.5(18) . . . . ? C3 C2 C7 C6 3(2) . . . . ? C1 C2 C7 C6 -177.1(13) . . . . ? C6 C7 C8 C9 0(3) . . . . ? C2 C7 C8 C9 -178.8(13) . . . . ? C6 C7 C8 P1 -175.4(14) . . . . ? C2 C7 C8 P1 6.2(17) . . . . ? C20 P1 C8 C7 -122.0(12) . . . . ? C1 P1 C8 C7 -9.5(12) . . . . ? Pd1 P1 C8 C7 98.6(11) . . . . ? C20 P1 C8 C9 63.2(14) . . . . ? C1 P1 C8 C9 175.7(13) . . . . ? Pd1 P1 C8 C9 -76.2(14) . . . . ? C7 C8 C9 C10 -64(2) . . . . ? P1 C8 C9 C10 110.2(16) . . . . ? C7 C8 C9 C14 114.9(18) . . . . ? P1 C8 C9 C14 -70.8(18) . . . . ? C14 C9 C10 C11 -2(3) . . . . ? C8 C9 C10 C11 177.1(16) . . . . ? C9 C10 C11 C12 -2(3) . . . . ? C10 C11 C12 C13 4(3) . . . . ? C11 C12 C13 C14 -2(3) . . . . ? C10 C9 C14 C13 4(3) . . . . ? C8 C9 C14 C13 -175.0(14) . . . . ? C12 C13 C14 C9 -2(3) . . . . ? C19 N8 C15 C16 -1(2) . . . . ? Pd1 N8 C15 C16 -176.2(12) . . . . ? C19 N8 C15 C1 -173.2(12) . . . . ? Pd1 N8 C15 C1 11.5(15) . . . . ? C2 C1 C15 C16 -67.7(19) . . . . ? P1 C1 C15 C16 172.0(13) . . . . ? C2 C1 C15 N8 104.0(12) . . . . ? P1 C1 C15 N8 -16.3(16) . . . . ? N8 C15 C16 C17 -2(2) . . . . ? C1 C15 C16 C17 169.9(15) . . . . ? C15 C16 C17 C18 3(3) . . . . ? C16 C17 C18 C19 -1(3) . . . . ? C15 N8 C19 C18 2(2) . . . . ? Pd1 N8 C19 C18 177.8(11) . . . . ? C17 C18 C19 N8 -1(2) . . . . ? C8 P1 C20 C25 -133.1(15) . . . . ? C1 P1 C20 C25 124.3(15) . . . . ? Pd1 P1 C20 C25 8.1(16) . . . . ? C8 P1 C20 C21 50.7(15) . . . . ? C1 P1 C20 C21 -51.9(16) . . . . ? Pd1 P1 C20 C21 -168.2(12) . . . . ? C25 C20 C21 C22 3(3) . . . . ? P1 C20 C21 C22 178.8(15) . . . . ? C20 C21 C22 C23 -4(3) . . . . ? C21 C22 C23 C24 3(3) . . . . ? C22 C23 C24 C25 -1(4) . . . . ? C23 C24 C25 C20 -1(4) . . . . ? C21 C20 C25 C24 0(3) . . . . ? P1 C20 C25 C24 -176.6(19) . . . . ? _diffrn_measured_fraction_theta_max 0.864 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.864 _refine_diff_density_max 5.063 _refine_diff_density_min -1.242 _refine_diff_density_rms 0.368 #====END ############################################################################## data_compound_2c' _database_code_CSD 208513 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23.50 H26 Cl3 N P Pd S' _chemical_formula_weight 598.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 10.866(5) _cell_length_b 15.475(5) _cell_length_c 16.973(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.722(5) _cell_angle_gamma 90.00 _cell_volume 2733.3(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 1.118 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method none _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 12092 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6251 _reflns_number_gt 4972 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.1149P)^2^+3.1669P] 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 SHELXL _refine_ls_extinction_coef 0.0070(13) _refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6251 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0709 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.1869 _refine_ls_wR_factor_gt 0.1687 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 2.106 _refine_ls_shift/su_mean 0.120 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 Pd1 Pd 0.75507(3) 0.03964(2) 0.28992(2) 0.04885(17) Uani 1 1 d . . . Cl1 Cl 0.61412(16) -0.03435(9) 0.34260(12) 0.0811(5) Uani 1 1 d . . . Cl2 Cl 0.7444(2) -0.06794(12) 0.18811(14) 0.1094(7) Uani 1 1 d . . . P1 P 0.75702(9) 0.14143(6) 0.37976(6) 0.0410(2) Uani 1 1 d . . . S1 S 0.65237(14) 0.07311(11) 0.55784(11) 0.0789(4) Uani 1 1 d . . . N1 N 0.8799(3) 0.1198(2) 0.2518(2) 0.0489(8) Uani 1 1 d . . . C1 C 0.8737(4) 0.2203(3) 0.3625(3) 0.0467(9) Uani 1 1 d . . . C2 C 0.9880(4) 0.2122(3) 0.4400(3) 0.0549(10) Uani 1 1 d . . . C3 C 1.1055(6) 0.2460(5) 0.4497(4) 0.084(2) Uani 1 1 d . . . C4 C 1.2114(7) 0.2396(7) 0.5258(4) 0.122(4) Uani 1 1 d . . . H4A H 1.2609 0.2927 0.5340 0.147 Uiso 1 1 calc R . . H4B H 1.2679 0.1926 0.5211 0.147 Uiso 1 1 calc R . . C5 C 1.1601(6) 0.2235(6) 0.6012(4) 0.102(3) Uani 1 1 d . . . H5A H 1.2315 0.2094 0.6488 0.122 Uiso 1 1 calc R . . H5B H 1.1201 0.2758 0.6135 0.122 Uiso 1 1 calc R . . C6 C 1.0634(5) 0.1505(5) 0.5849(3) 0.0728(15) Uani 1 1 d . . . H6A H 1.1077 0.0963 0.5838 0.087 Uiso 1 1 calc R . . H6B H 1.0245 0.1477 0.6296 0.087 Uiso 1 1 calc R . . C7 C 0.9594(4) 0.1610(3) 0.5052(3) 0.0511(9) Uani 1 1 d . . . C8 C 0.8431(4) 0.1223(3) 0.4863(3) 0.0448(8) Uani 1 1 d . . . C9 C 0.8009(4) 0.0647(3) 0.5407(3) 0.0474(9) Uani 1 1 d . . . C10 C 0.8720(5) -0.0018(4) 0.5893(4) 0.0709(15) Uani 1 1 d . . . H10 H 0.9560 -0.0162 0.5915 0.085 Uiso 1 1 calc R . . C11 C 0.7967(6) -0.0452(4) 0.6358(4) 0.0792(17) Uani 1 1 d . . . H11 H 0.8265 -0.0924 0.6699 0.095 Uiso 1 1 calc R . . C12 C 0.6811(6) -0.0108(4) 0.6249(4) 0.0792(16) Uani 1 1 d . . . H12 H 0.6223 -0.0306 0.6512 0.095 Uiso 1 1 calc R . . C13 C 0.9099(4) 0.1985(3) 0.2857(2) 0.0457(9) Uani 1 1 d . . . C14 C 0.9756(5) 0.2591(3) 0.2524(3) 0.0598(11) Uani 1 1 d . . . H14 H 0.9892 0.3147 0.2739 0.072 Uiso 1 1 calc R . . C15 C 1.0201(5) 0.2357(5) 0.1874(3) 0.0726(15) Uani 1 1 d . . . H15 H 1.0652 0.2750 0.1648 0.087 Uiso 1 1 calc R . . C16 C 0.9969(6) 0.1535(5) 0.1565(3) 0.0800(17) Uani 1 1 d . . . H16 H 1.0296 0.1356 0.1142 0.096 Uiso 1 1 calc R . . C17 C 0.9250(5) 0.0976(4) 0.1885(3) 0.0646(12) Uani 1 1 d . . . H17 H 0.9070 0.0428 0.1657 0.078 Uiso 1 1 calc R . . C20 C 0.6000(4) 0.1909(3) 0.3699(3) 0.0504(9) Uani 1 1 d . . . C21 C 0.5369(5) 0.2150(4) 0.2793(3) 0.0655(13) Uani 1 1 d . . . H21A H 0.5310 0.1641 0.2451 0.079 Uiso 1 1 calc R . . H21B H 0.5896 0.2574 0.2619 0.079 Uiso 1 1 calc R . . C22 C 0.4029(6) 0.2520(5) 0.2684(4) 0.091(2) Uani 1 1 d . . . H22A H 0.3669 0.2703 0.2118 0.109 Uiso 1 1 calc R . . H22B H 0.3479 0.2071 0.2796 0.109 Uiso 1 1 calc R . . C23 C 0.4049(7) 0.3271(5) 0.3243(5) 0.103(2) Uani 1 1 d . . . H23A H 0.4495 0.3750 0.3078 0.124 Uiso 1 1 calc R . . H23B H 0.3174 0.3453 0.3186 0.124 Uiso 1 1 calc R . . C24 C 0.4711(7) 0.3051(5) 0.4147(5) 0.098(2) Uani 1 1 d . . . H24A H 0.4200 0.2629 0.4336 0.117 Uiso 1 1 calc R . . H24B H 0.4765 0.3568 0.4479 0.117 Uiso 1 1 calc R . . C25 C 0.6067(5) 0.2688(3) 0.4264(3) 0.0609(12) Uani 1 1 d . . . H25A H 0.6612 0.3131 0.4135 0.073 Uiso 1 1 calc R . . H25B H 0.6438 0.2515 0.4832 0.073 Uiso 1 1 calc R . . Cl70 Cl 1.1020(10) 0.6203(4) 0.4337(5) 0.244(6) Uani 0.50 1 d P . . Cl72 Cl 1.2868(14) 0.4883(8) 0.4560(9) 0.286(7) Uani 0.50 1 d P . . C70 C 1.080(2) 0.5125(10) 0.4021(14) 0.127(7) Uani 0.50 1 d P . . H70A H 1.0514 0.5055 0.3429 0.153 Uiso 0.50 1 calc PR . . H70B H 1.0264 0.4801 0.4282 0.153 Uiso 0.50 1 calc PR . . H1 H 0.850(5) 0.284(4) 0.363(3) 0.061(14) Uiso 1 1 d . . . H3 H 1.108(7) 0.286(5) 0.409(4) 0.10(2) 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 Pd1 0.0494(2) 0.0424(2) 0.0554(3) -0.00725(12) 0.01614(16) 0.00046(12) Cl1 0.0815(9) 0.0615(8) 0.1154(12) -0.0209(7) 0.0525(9) -0.0227(6) Cl2 0.1601(19) 0.0734(10) 0.1212(14) -0.0511(10) 0.0827(14) -0.0356(11) P1 0.0360(5) 0.0401(5) 0.0467(5) -0.0016(4) 0.0113(4) 0.0021(4) S1 0.0581(7) 0.0816(10) 0.1067(11) 0.0255(8) 0.0392(8) 0.0112(7) N1 0.0469(18) 0.056(2) 0.0430(17) 0.0047(14) 0.0125(14) 0.0084(15) C1 0.045(2) 0.041(2) 0.055(2) 0.0003(16) 0.0169(17) -0.0016(16) C2 0.056(2) 0.062(3) 0.049(2) -0.0150(19) 0.0185(19) -0.019(2) C3 0.068(3) 0.131(6) 0.056(3) -0.010(3) 0.020(2) -0.045(4) C4 0.076(4) 0.225(11) 0.059(3) -0.017(5) 0.011(3) -0.075(5) C5 0.079(4) 0.168(8) 0.053(3) -0.022(4) 0.011(3) -0.060(5) C6 0.055(3) 0.112(5) 0.047(2) -0.011(3) 0.008(2) -0.021(3) C7 0.046(2) 0.059(3) 0.049(2) -0.0097(18) 0.0144(17) -0.0078(18) C8 0.0387(18) 0.044(2) 0.050(2) -0.0021(16) 0.0104(16) 0.0027(15) C9 0.0409(19) 0.054(2) 0.048(2) -0.0006(17) 0.0141(16) -0.0003(17) C10 0.061(3) 0.074(3) 0.086(4) 0.033(3) 0.035(3) 0.017(3) C11 0.065(3) 0.094(4) 0.081(4) 0.038(3) 0.025(3) 0.006(3) C12 0.066(3) 0.083(4) 0.098(4) 0.019(3) 0.040(3) -0.002(3) C13 0.0383(18) 0.053(2) 0.044(2) 0.0092(16) 0.0088(15) 0.0066(16) C14 0.053(2) 0.066(3) 0.058(3) 0.016(2) 0.012(2) -0.003(2) C15 0.061(3) 0.105(5) 0.053(3) 0.025(3) 0.017(2) -0.003(3) C16 0.072(3) 0.121(5) 0.054(3) 0.006(3) 0.029(3) 0.003(3) C17 0.070(3) 0.074(3) 0.052(2) -0.001(2) 0.021(2) 0.008(2) C20 0.0395(19) 0.058(3) 0.054(2) 0.0016(18) 0.0143(17) 0.0097(17) C21 0.054(3) 0.080(3) 0.055(3) 0.005(2) 0.004(2) 0.017(2) C22 0.053(3) 0.117(5) 0.091(4) 0.020(4) 0.004(3) 0.027(3) C23 0.087(4) 0.102(5) 0.122(6) 0.023(5) 0.032(4) 0.057(4) C24 0.105(5) 0.103(5) 0.103(5) 0.012(4) 0.058(4) 0.054(4) C25 0.067(3) 0.056(3) 0.065(3) -0.002(2) 0.029(2) 0.014(2) Cl70 0.338(11) 0.121(4) 0.161(6) -0.042(4) -0.106(6) 0.093(6) Cl72 0.367(16) 0.218(9) 0.368(16) 0.055(11) 0.254(14) 0.174(11) C70 0.19(2) 0.064(8) 0.138(15) 0.019(10) 0.069(16) 0.024(11) _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 Pd1 N1 2.074(4) . ? Pd1 P1 2.1883(11) . ? Pd1 Cl1 2.2902(16) . ? Pd1 Cl2 2.3782(16) . ? P1 C8 1.804(4) . ? P1 C20 1.833(4) . ? P1 C1 1.843(4) . ? S1 C12 1.695(7) . ? S1 C9 1.725(4) . ? N1 C17 1.346(6) . ? N1 C13 1.346(6) . ? C1 C13 1.505(6) . ? C1 C2 1.532(6) . ? C2 C3 1.345(7) . ? C2 C7 1.466(6) . ? C3 C4 1.465(9) . ? C4 C5 1.556(9) . ? C5 C6 1.513(8) . ? C6 C7 1.501(7) . ? C7 C8 1.351(6) . ? C8 C9 1.450(6) . ? C9 C10 1.404(7) . ? C10 C11 1.455(8) . ? C11 C12 1.327(9) . ? C13 C14 1.393(6) . ? C14 C15 1.374(8) . ? C15 C16 1.371(10) . ? C16 C17 1.378(9) . ? C20 C21 1.538(6) . ? C20 C25 1.529(7) . ? C21 C22 1.525(7) . ? C22 C23 1.496(11) . ? C23 C24 1.534(10) . ? C24 C25 1.536(7) . ? Cl70 C70 1.746(19) . ? Cl72 C70 2.20(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Pd1 P1 84.89(11) . . ? N1 Pd1 Cl1 172.60(11) . . ? P1 Pd1 Cl1 87.78(5) . . ? N1 Pd1 Cl2 95.25(11) . . ? P1 Pd1 Cl2 177.35(7) . . ? Cl1 Pd1 Cl2 92.02(6) . . ? C8 P1 C20 111.14(19) . . ? C8 P1 C1 94.93(19) . . ? C20 P1 C1 111.9(2) . . ? C8 P1 Pd1 118.57(14) . . ? C20 P1 Pd1 114.50(15) . . ? C1 P1 Pd1 103.60(14) . . ? C12 S1 C9 93.1(3) . . ? C17 N1 C13 118.2(4) . . ? C17 N1 Pd1 121.1(4) . . ? C13 N1 Pd1 120.5(3) . . ? C13 C1 C2 112.1(3) . . ? C13 C1 P1 110.6(3) . . ? C2 C1 P1 103.6(3) . . ? C3 C2 C7 121.1(5) . . ? C3 C2 C1 125.5(5) . . ? C7 C2 C1 113.4(3) . . ? C2 C3 C4 124.0(6) . . ? C3 C4 C5 111.1(5) . . ? C6 C5 C4 111.3(5) . . ? C7 C6 C5 112.8(5) . . ? C8 C7 C2 116.6(4) . . ? C8 C7 C6 125.2(4) . . ? C2 C7 C6 118.1(4) . . ? C7 C8 C9 124.5(4) . . ? C7 C8 P1 110.2(3) . . ? C9 C8 P1 124.9(3) . . ? C10 C9 C8 127.1(4) . . ? C10 C9 S1 109.9(3) . . ? C8 C9 S1 122.9(3) . . ? C9 C10 C11 110.9(5) . . ? C12 C11 C10 113.4(5) . . ? C11 C12 S1 112.7(4) . . ? N1 C13 C14 121.7(4) . . ? N1 C13 C1 118.8(4) . . ? C14 C13 C1 119.5(4) . . ? C15 C14 C13 119.2(5) . . ? C14 C15 C16 118.8(5) . . ? C15 C16 C17 119.6(5) . . ? N1 C17 C16 122.1(6) . . ? C21 C20 C25 111.3(4) . . ? C21 C20 P1 109.2(3) . . ? C25 C20 P1 113.4(3) . . ? C20 C21 C22 110.3(5) . . ? C23 C22 C21 112.1(5) . . ? C24 C23 C22 112.3(6) . . ? C23 C24 C25 111.5(5) . . ? C20 C25 C24 109.7(5) . . ? Cl70 C70 Cl72 90.2(11) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.254 _refine_diff_density_min -0.837 _refine_diff_density_rms 0.132 #====END