# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'LeGrande Slaughter' _publ_contact_author_address ; Department of Chemistry Oklahoma State University Stillwater Oklahoma 74078 UNITED STATES OF AMERICA ; _publ_contact_author_email LMS@CHEM.OKSTATE.EDU _publ_section_title ; One-step assembly of a chiral palladium bis(acyclic diaminocarbene) complex and its unexpected oxidation to a bis(amidine) complex ; loop_ _publ_author_name 'LeGrande Slaughter' 'Yoshitha A. Wanniarachchi' # Attachment 'slaughter_structures.cif' data_slaughter_cmplx_3 _database_code_depnum_ccdc_archive 'CCDC 625246' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'Pd cyclohexanedicarbene dichloride' _chemical_melting_point ? _chemical_formula_moiety 'C24 H26 Cl2 F6 N4 Pd, 2(C H4 O)' _chemical_formula_sum 'C26 H34 Cl2 F6 N4 O2 Pd' _chemical_formula_weight 725.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0588(4) _cell_length_b 14.0376(8) _cell_length_c 14.1642(8) _cell_angle_alpha 84.861(4) _cell_angle_beta 85.869(4) _cell_angle_gamma 74.662(4) _cell_volume 1537.11(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3102 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 25.44 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.844 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6538 _exptl_absorpt_correction_T_max 0.9874 _exptl_absorpt_process_details 'Bruker Nonius TWINABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.75 _diffrn_standards_number 0 _diffrn_standards_interval_count N/A _diffrn_standards_interval_time N/A _diffrn_standards_decay_% N/A _diffrn_reflns_number 9760 _diffrn_reflns_av_R_equivalents 0.057 _diffrn_reflns_av_sigmaI/netI 0.0958 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 23.25 _reflns_number_total 4285 _reflns_number_gt 5079 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL (XS)' _computing_structure_refinement 'Bruker SHELXTL (XL)' _computing_molecular_graphics 'Bruker SHELXTL (XP)' _computing_publication_material 'Bruker SHELXTL (XCIF)' _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. Crystal was modeled as a two-component non-merohedral twin with each component having identical cell parameters. Final refinement used reflections from both components in HKLF5 format. Twin law: 1.00 0.00 0.00 0.92 -1.00 0.00 0.25 0.00 -1.00 Refined proportions of twin components: 0.55, 0.45 ; _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^)+(0.0520P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6662 _refine_ls_number_parameters 375 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1141 _refine_ls_wR_factor_gt 0.1073 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 Pd1 Pd 0.86053(6) 0.49136(4) 0.27443(4) 0.01787(15) Uani 1 1 d . . . C1 C 1.0591(7) 0.4620(5) 0.3561(4) 0.0180(15) Uani 1 1 d . . . C2 C 1.0294(8) 0.4036(5) 0.1901(4) 0.0219(16) Uani 1 1 d . . . Cl1 Cl 0.68480(18) 0.60240(12) 0.38264(11) 0.0227(4) Uani 1 1 d . . . Cl2 Cl 0.65410(19) 0.54680(12) 0.15513(11) 0.0234(4) Uani 1 1 d . . . N1 N 1.0885(6) 0.3969(4) 0.4327(3) 0.0187(12) Uani 1 1 d . . . H1 H 1.1772 0.3977 0.4652 0.022 Uiso 1 1 calc R . . C3 C 1.3493(7) 0.4839(5) 0.3693(4) 0.0229(15) Uani 1 1 d . . . H3A H 1.3970 0.4120 0.3714 0.034 Uiso 1 1 calc R . . H3B H 1.3389 0.5060 0.4337 0.034 Uiso 1 1 calc R . . H3C H 1.4260 0.5163 0.3294 0.034 Uiso 1 1 calc R . . C4 C 1.2837(8) 0.3715(5) 0.0797(4) 0.0268(16) Uani 1 1 d . . . H4A H 1.2231 0.3608 0.0256 0.040 Uiso 1 1 calc R . . H4B H 1.3372 0.3075 0.1127 0.040 Uiso 1 1 calc R . . H4C H 1.3730 0.4050 0.0569 0.040 Uiso 1 1 calc R . . C5 C 1.1452(9) 0.5806(5) 0.2440(4) 0.0330(18) Uani 1 1 d . . . H5 H 1.0169 0.6057 0.2441 0.040 Uiso 1 1 calc R . . C6 C 1.1954(9) 0.5297(5) 0.1534(4) 0.0321(17) Uani 1 1 d . . . H6 H 1.3240 0.5146 0.1493 0.039 Uiso 1 1 calc R . . C7 C 1.1413(8) 0.6020(5) 0.0672(4) 0.0276(17) Uani 1 1 d . . . H7A H 1.1947 0.5696 0.0092 0.033 Uiso 1 1 calc R . . H7B H 1.0147 0.6167 0.0635 0.033 Uiso 1 1 calc R . . C8 C 1.1905(9) 0.6979(5) 0.0689(5) 0.0395(19) Uani 1 1 d . . . H8A H 1.1268 0.7459 0.0201 0.047 Uiso 1 1 calc R . . H8B H 1.3149 0.6862 0.0510 0.047 Uiso 1 1 calc R . . C9 C 1.1561(9) 0.7440(5) 0.1627(4) 0.0340(18) Uani 1 1 d . . . H9A H 1.0314 0.7764 0.1706 0.041 Uiso 1 1 calc R . . H9B H 1.2186 0.7960 0.1616 0.041 Uiso 1 1 calc R . . C10 C 1.2089(8) 0.6713(5) 0.2474(4) 0.0275(17) Uani 1 1 d . . . H10A H 1.3361 0.6516 0.2490 0.033 Uiso 1 1 calc R . . H10B H 1.1620 0.7038 0.3064 0.033 Uiso 1 1 calc R . . N2 N 1.0218(6) 0.3113(4) 0.1751(4) 0.0227(13) Uani 1 1 d . . . H2 H 1.0988 0.2787 0.1343 0.027 Uiso 1 1 calc R . . N3 N 1.1783(6) 0.5102(4) 0.3293(3) 0.0191(12) Uani 1 1 d . . . N4 N 1.1604(6) 0.4333(4) 0.1454(3) 0.0222(13) Uani 1 1 d . . . C11 C 0.9955(7) 0.3275(5) 0.4680(4) 0.0193(15) Uani 1 1 d . . . C12 C 1.0886(8) 0.2434(5) 0.5192(4) 0.0243(16) Uani 1 1 d . . . H12 H 1.2074 0.2353 0.5281 0.029 Uiso 1 1 calc R . . C13 C 1.0089(8) 0.1711(5) 0.5573(4) 0.0264(16) Uani 1 1 d . . . H13 H 1.0733 0.1130 0.5909 0.032 Uiso 1 1 calc R . . C14 C 0.8332(8) 0.1844(5) 0.5459(4) 0.0224(15) Uani 1 1 d . . . C15 C 0.7416(8) 0.2673(5) 0.4961(4) 0.0277(17) Uani 1 1 d . . . H15 H 0.6226 0.2756 0.4879 0.033 Uiso 1 1 calc R . . C16 C 0.8218(7) 0.3401(5) 0.4573(4) 0.0205(15) Uani 1 1 d . . . H16 H 0.7568 0.3980 0.4237 0.025 Uiso 1 1 calc R . . C17 C 0.7501(9) 0.1070(5) 0.5906(5) 0.0318(17) Uani 1 1 d . . . C21 C 0.8992(8) 0.2613(5) 0.2200(4) 0.0227(16) Uani 1 1 d . . . C22 C 0.9634(8) 0.1684(5) 0.2643(5) 0.0310(18) Uani 1 1 d . . . H22 H 1.0840 0.1421 0.2698 0.037 Uiso 1 1 calc R . . C23 C 0.8499(8) 0.1140(5) 0.3007(5) 0.0348(19) Uani 1 1 d . . . H23 H 0.8931 0.0498 0.3310 0.042 Uiso 1 1 calc R . . C24 C 0.6757(8) 0.1518(5) 0.2936(4) 0.0263(17) Uani 1 1 d . . . C25 C 0.6117(8) 0.2455(5) 0.2513(5) 0.0305(17) Uani 1 1 d . . . H25 H 0.4908 0.2729 0.2488 0.037 Uiso 1 1 calc R . . F1 F 0.5792(5) 0.1336(3) 0.5859(3) 0.0462(12) Uani 1 1 d . . . F2 F 0.7828(5) 0.0846(3) 0.6826(3) 0.0443(11) Uani 1 1 d . . . F3 F 0.8062(5) 0.0206(3) 0.5500(3) 0.0512(12) Uani 1 1 d . . . F4 F 0.4589(6) 0.0770(3) 0.2625(3) 0.0621(14) Uani 1 1 d . . . F5 F 0.4311(6) 0.1426(4) 0.3922(4) 0.0760(16) Uani 1 1 d . . . C26 C 0.7245(8) 0.3001(5) 0.2124(4) 0.0287(17) Uani 1 1 d . . . H26 H 0.6813 0.3635 0.1807 0.034 Uiso 1 1 calc R . . C27 C 0.5494(9) 0.0937(5) 0.3314(5) 0.0345(18) Uani 1 1 d . . . F6 F 0.6219(5) 0.0076(3) 0.3734(4) 0.0721(16) Uani 1 1 d . . . O1 O 0.3195(7) 0.2326(4) 0.8791(4) 0.0581(16) Uani 1 1 d . . . H100 H 0.3325 0.2896 0.8649 0.087 Uiso 1 1 calc R . . C28 C 0.3761(10) 0.1740(6) 0.8014(5) 0.054(2) Uani 1 1 d . . . H28A H 0.3300 0.2116 0.7431 0.081 Uiso 1 1 calc R . . H28B H 0.3354 0.1138 0.8115 0.081 Uiso 1 1 calc R . . H28C H 0.5023 0.1558 0.7955 0.081 Uiso 1 1 calc R . . O2 O 0.2184(7) 0.1627(4) 0.0536(4) 0.0537(15) Uani 1 1 d . . . H200 H 0.2493 0.1836 -0.0004 0.081 Uiso 1 1 calc R . . C29 C 0.2154(14) 0.0636(7) 0.0517(7) 0.093(4) Uani 1 1 d . . . H29A H 0.3275 0.0249 0.0272 0.140 Uiso 1 1 calc R . . H29B H 0.1254 0.0594 0.0105 0.140 Uiso 1 1 calc R . . H29C H 0.1912 0.0371 0.1161 0.140 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 0.0094(3) 0.0287(3) 0.0172(3) -0.0010(2) -0.0007(2) -0.0081(2) C1 0.007(3) 0.028(4) 0.017(4) -0.001(3) 0.008(3) -0.004(3) C2 0.016(4) 0.034(5) 0.015(4) 0.001(3) -0.002(3) -0.006(3) Cl1 0.0163(9) 0.0321(10) 0.0200(9) -0.0048(8) -0.0006(7) -0.0059(7) Cl2 0.0164(9) 0.0374(10) 0.0175(9) -0.0007(8) -0.0035(7) -0.0086(7) N1 0.012(3) 0.031(3) 0.016(3) 0.000(3) -0.003(2) -0.009(2) C3 0.009(3) 0.040(4) 0.022(4) -0.003(3) 0.004(3) -0.009(3) C4 0.019(4) 0.039(4) 0.022(4) -0.005(3) 0.006(3) -0.008(3) C5 0.041(5) 0.040(5) 0.027(4) 0.005(4) -0.010(4) -0.027(4) C6 0.040(5) 0.035(4) 0.026(4) -0.004(3) 0.004(4) -0.017(4) C7 0.029(4) 0.029(4) 0.023(4) 0.007(3) -0.011(3) -0.007(3) C8 0.045(5) 0.047(5) 0.030(4) 0.008(4) -0.003(4) -0.022(4) C9 0.037(4) 0.036(5) 0.032(4) -0.002(4) 0.005(4) -0.017(3) C10 0.032(4) 0.032(4) 0.020(4) 0.000(3) -0.006(3) -0.009(3) N2 0.015(3) 0.032(4) 0.022(3) -0.003(3) 0.001(2) -0.008(2) N3 0.013(3) 0.030(3) 0.017(3) 0.001(2) -0.004(2) -0.012(2) N4 0.017(3) 0.032(4) 0.020(3) -0.004(3) 0.005(2) -0.012(3) C11 0.016(4) 0.027(4) 0.017(4) -0.003(3) 0.003(3) -0.011(3) C12 0.021(4) 0.030(4) 0.025(4) -0.002(3) 0.001(3) -0.013(3) C13 0.024(4) 0.026(4) 0.025(4) -0.002(3) 0.000(3) 0.002(3) C14 0.023(4) 0.026(4) 0.019(4) -0.008(3) 0.008(3) -0.009(3) C15 0.021(4) 0.035(5) 0.029(4) -0.007(4) 0.001(3) -0.010(3) C16 0.015(4) 0.027(4) 0.022(4) -0.008(3) 0.004(3) -0.009(3) C17 0.030(5) 0.032(5) 0.035(5) -0.003(4) 0.005(4) -0.012(4) C21 0.020(4) 0.034(4) 0.017(4) 0.000(3) -0.005(3) -0.011(3) C22 0.019(4) 0.030(4) 0.046(5) -0.007(4) 0.002(3) -0.008(3) C23 0.021(4) 0.029(4) 0.053(5) 0.010(4) -0.002(4) -0.008(3) C24 0.025(4) 0.036(5) 0.023(4) 0.001(3) -0.002(3) -0.020(3) C25 0.015(4) 0.041(5) 0.037(4) -0.003(4) -0.003(3) -0.009(3) F1 0.026(3) 0.043(3) 0.072(3) 0.010(2) 0.005(2) -0.0197(19) F2 0.049(3) 0.054(3) 0.034(3) 0.012(2) 0.003(2) -0.027(2) F3 0.059(3) 0.031(3) 0.068(3) -0.018(2) 0.025(2) -0.023(2) F4 0.051(3) 0.089(4) 0.066(3) -0.002(3) -0.010(3) -0.053(3) F5 0.065(3) 0.079(4) 0.096(4) -0.034(3) 0.054(3) -0.047(3) C26 0.024(4) 0.039(5) 0.026(4) 0.008(3) -0.010(3) -0.012(3) C27 0.022(4) 0.037(5) 0.049(5) -0.002(4) -0.001(4) -0.018(4) F6 0.039(3) 0.060(3) 0.119(4) 0.047(3) -0.021(3) -0.029(2) O1 0.085(4) 0.046(4) 0.047(4) -0.016(3) 0.031(3) -0.030(3) C28 0.056(6) 0.049(6) 0.050(5) -0.009(5) 0.010(4) -0.001(4) O2 0.076(4) 0.040(4) 0.046(3) -0.009(3) 0.022(3) -0.021(3) C29 0.150(10) 0.046(6) 0.084(8) -0.022(6) 0.047(7) -0.035(6) _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 C1 1.975(6) . ? Pd1 C2 1.985(6) . ? Pd1 Cl2 2.3901(16) . ? Pd1 Cl1 2.3942(16) . ? C1 N3 1.331(7) . ? C1 N1 1.346(7) . ? C2 N4 1.333(7) . ? C2 N2 1.350(8) . ? N1 C11 1.416(7) . ? N1 H1 0.8800 . ? C3 N3 1.471(7) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 N4 1.471(7) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N3 1.483(7) . ? C5 C10 1.499(8) . ? C5 C6 1.502(9) . ? C5 H5 1.0000 . ? C6 N4 1.469(8) . ? C6 C7 1.526(8) . ? C6 H6 1.0000 . ? C7 C8 1.505(9) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.505(9) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.512(8) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? N2 C21 1.438(7) . ? N2 H2 0.8800 . ? C11 C16 1.382(8) . ? C11 C12 1.393(8) . ? C12 C13 1.389(8) . ? C12 H12 0.9500 . ? C13 C14 1.397(9) . ? C13 H13 0.9500 . ? C14 C15 1.367(9) . ? C14 C17 1.494(9) . ? C15 C16 1.401(8) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 F1 1.333(7) . ? C17 F2 1.340(7) . ? C17 F3 1.343(7) . ? C21 C26 1.377(8) . ? C21 C22 1.381(9) . ? C22 C23 1.385(8) . ? C22 H22 0.9500 . ? C23 C24 1.371(9) . ? C23 H23 0.9500 . ? C24 C25 1.379(9) . ? C24 C27 1.506(8) . ? C25 C26 1.391(8) . ? C25 H25 0.9500 . ? F4 C27 1.332(7) . ? F5 C27 1.328(8) . ? C26 H26 0.9500 . ? C27 F6 1.306(8) . ? O1 C28 1.410(8) . ? O1 H100 0.8400 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? O2 C29 1.401(9) . ? O2 H200 0.8400 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Pd1 C2 82.3(2) . . ? C1 Pd1 Cl2 167.99(17) . . ? C2 Pd1 Cl2 93.62(18) . . ? C1 Pd1 Cl1 91.90(17) . . ? C2 Pd1 Cl1 173.35(19) . . ? Cl2 Pd1 Cl1 91.39(6) . . ? N3 C1 N1 117.5(5) . . ? N3 C1 Pd1 115.2(4) . . ? N1 C1 Pd1 127.3(4) . . ? N4 C2 N2 116.0(6) . . ? N4 C2 Pd1 120.9(5) . . ? N2 C2 Pd1 123.2(4) . . ? C1 N1 C11 128.5(5) . . ? C1 N1 H1 115.7 . . ? C11 N1 H1 115.7 . . ? N3 C3 H3A 109.5 . . ? N3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N4 C4 H4A 109.5 . . ? N4 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N4 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 C10 114.6(5) . . ? N3 C5 C6 112.3(5) . . ? C10 C5 C6 114.1(5) . . ? N3 C5 H5 104.8 . . ? C10 C5 H5 104.8 . . ? C6 C5 H5 104.8 . . ? N4 C6 C5 119.7(5) . . ? N4 C6 C7 112.7(5) . . ? C5 C6 C7 111.0(5) . . ? N4 C6 H6 103.8 . . ? C5 C6 H6 103.8 . . ? C7 C6 H6 103.8 . . ? C8 C7 C6 114.0(5) . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7B 108.7 . . ? C6 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C7 C8 C9 115.1(6) . . ? C7 C8 H8A 108.5 . . ? C9 C8 H8A 108.5 . . ? C7 C8 H8B 108.5 . . ? C9 C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? C8 C9 C10 114.1(6) . . ? C8 C9 H9A 108.7 . . ? C10 C9 H9A 108.7 . . ? C8 C9 H9B 108.7 . . ? C10 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C5 C10 C9 111.7(5) . . ? C5 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C5 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C2 N2 C21 125.9(5) . . ? C2 N2 H2 117.1 . . ? C21 N2 H2 117.1 . . ? C1 N3 C3 122.8(5) . . ? C1 N3 C5 116.9(5) . . ? C3 N3 C5 119.4(5) . . ? C2 N4 C6 125.0(5) . . ? C2 N4 C4 122.1(5) . . ? C6 N4 C4 112.9(5) . . ? C16 C11 C12 119.6(6) . . ? C16 C11 N1 124.4(6) . . ? C12 C11 N1 116.0(5) . . ? C13 C12 C11 120.4(6) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 119.5(6) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.1(6) . . ? C15 C14 C17 121.8(6) . . ? C13 C14 C17 118.2(6) . . ? C14 C15 C16 120.6(6) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C11 C16 C15 119.8(6) . . ? C11 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? F1 C17 F2 106.7(5) . . ? F1 C17 F3 106.4(6) . . ? F2 C17 F3 104.9(6) . . ? F1 C17 C14 112.8(6) . . ? F2 C17 C14 112.8(6) . . ? F3 C17 C14 112.6(5) . . ? C26 C21 C22 120.7(6) . . ? C26 C21 N2 121.7(6) . . ? C22 C21 N2 117.4(5) . . ? C21 C22 C23 119.2(6) . . ? C21 C22 H22 120.4 . . ? C23 C22 H22 120.4 . . ? C24 C23 C22 120.7(6) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C25 120.0(6) . . ? C23 C24 C27 121.8(6) . . ? C25 C24 C27 118.2(6) . . ? C24 C25 C26 119.9(6) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C21 C26 C25 119.5(6) . . ? C21 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? F6 C27 F5 107.6(6) . . ? F6 C27 F4 106.9(6) . . ? F5 C27 F4 104.3(6) . . ? F6 C27 C24 113.6(6) . . ? F5 C27 C24 112.4(6) . . ? F4 C27 C24 111.5(6) . . ? C28 O1 H100 109.5 . . ? O1 C28 H28A 109.5 . . ? O1 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O1 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C29 O2 H200 109.5 . . ? O2 C29 H29A 109.5 . . ? O2 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O2 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 Pd1 C1 N3 76.4(5) . . . . ? Cl2 Pd1 C1 N3 5.5(12) . . . . ? Cl1 Pd1 C1 N3 -100.3(4) . . . . ? C2 Pd1 C1 N1 -101.2(6) . . . . ? Cl2 Pd1 C1 N1 -172.0(5) . . . . ? Cl1 Pd1 C1 N1 82.1(5) . . . . ? C1 Pd1 C2 N4 -70.5(5) . . . . ? Cl2 Pd1 C2 N4 98.1(5) . . . . ? C1 Pd1 C2 N2 108.5(5) . . . . ? Cl2 Pd1 C2 N2 -82.9(5) . . . . ? N3 C1 N1 C11 -170.8(6) . . . . ? Pd1 C1 N1 C11 6.7(9) . . . . ? N3 C5 C6 N4 39.6(8) . . . . ? C10 C5 C6 N4 172.3(6) . . . . ? N3 C5 C6 C7 173.6(5) . . . . ? C10 C5 C6 C7 -53.7(8) . . . . ? N4 C6 C7 C8 -174.5(6) . . . . ? C5 C6 C7 C8 48.2(8) . . . . ? C6 C7 C8 C9 -44.4(9) . . . . ? C7 C8 C9 C10 44.2(8) . . . . ? N3 C5 C10 C9 -174.6(5) . . . . ? C6 C5 C10 C9 53.9(8) . . . . ? C8 C9 C10 C5 -47.9(8) . . . . ? N4 C2 N2 C21 175.9(5) . . . . ? Pd1 C2 N2 C21 -3.1(8) . . . . ? N1 C1 N3 C3 10.3(8) . . . . ? Pd1 C1 N3 C3 -167.5(4) . . . . ? N1 C1 N3 C5 179.2(5) . . . . ? Pd1 C1 N3 C5 1.3(7) . . . . ? C10 C5 N3 C1 145.0(6) . . . . ? C6 C5 N3 C1 -82.6(7) . . . . ? C10 C5 N3 C3 -45.7(8) . . . . ? C6 C5 N3 C3 86.7(6) . . . . ? N2 C2 N4 C6 -178.5(5) . . . . ? Pd1 C2 N4 C6 0.6(8) . . . . ? N2 C2 N4 C4 3.3(8) . . . . ? Pd1 C2 N4 C4 -177.6(4) . . . . ? C5 C6 N4 C2 30.4(9) . . . . ? C7 C6 N4 C2 -102.9(7) . . . . ? C5 C6 N4 C4 -151.3(6) . . . . ? C7 C6 N4 C4 75.4(7) . . . . ? C1 N1 C11 C16 -29.3(10) . . . . ? C1 N1 C11 C12 152.9(6) . . . . ? C16 C11 C12 C13 1.7(10) . . . . ? N1 C11 C12 C13 179.6(5) . . . . ? C11 C12 C13 C14 -1.5(9) . . . . ? C12 C13 C14 C15 1.1(9) . . . . ? C12 C13 C14 C17 -177.9(6) . . . . ? C13 C14 C15 C16 -0.8(9) . . . . ? C17 C14 C15 C16 178.1(6) . . . . ? C12 C11 C16 C15 -1.4(10) . . . . ? N1 C11 C16 C15 -179.1(5) . . . . ? C14 C15 C16 C11 1.0(10) . . . . ? C15 C14 C17 F1 -7.3(9) . . . . ? C13 C14 C17 F1 171.6(5) . . . . ? C15 C14 C17 F2 -128.3(6) . . . . ? C13 C14 C17 F2 50.7(8) . . . . ? C15 C14 C17 F3 113.2(7) . . . . ? C13 C14 C17 F3 -67.8(8) . . . . ? C2 N2 C21 C26 58.4(9) . . . . ? C2 N2 C21 C22 -127.1(7) . . . . ? C26 C21 C22 C23 0.4(10) . . . . ? N2 C21 C22 C23 -174.1(6) . . . . ? C21 C22 C23 C24 -0.4(11) . . . . ? C22 C23 C24 C25 -1.1(11) . . . . ? C22 C23 C24 C27 179.1(6) . . . . ? C23 C24 C25 C26 2.7(10) . . . . ? C27 C24 C25 C26 -177.6(6) . . . . ? C22 C21 C26 C25 1.2(10) . . . . ? N2 C21 C26 C25 175.4(6) . . . . ? C24 C25 C26 C21 -2.7(10) . . . . ? C23 C24 C27 F6 2.3(10) . . . . ? C25 C24 C27 F6 -177.4(6) . . . . ? C23 C24 C27 F5 124.8(7) . . . . ? C25 C24 C27 F5 -54.9(9) . . . . ? C23 C24 C27 F4 -118.5(8) . . . . ? C25 C24 C27 F4 61.8(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Cl1 0.88 2.50 3.298(5) 152.0 2_766 N2 H2 O2 0.88 2.06 2.885(7) 156.5 1_655 O1 H100 Cl2 0.84 2.32 3.152(5) 172.1 2_666 O2 H200 O1 0.84 1.89 2.726(7) 179.0 1_554 _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.717 _refine_diff_density_min -0.694 _refine_diff_density_rms 0.107 _exptl_crystal_recrystallization_method 'slow evap of MeOH soln' #===end data_slaughter_cmplx_4 _database_code_depnum_ccdc_archive 'CCDC 625247' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'Bis(amidine)PdCl2 cyclohexane backbone' _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 Cl2 F6 N4 Pd' _chemical_formula_sum 'C24 H24 Cl2 F6 N4 Pd' _chemical_formula_weight 659.77 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' F F 0.0171 0.0103 '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 'P n m a' _symmetry_int_tables_number 62 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 12.8242(6) _cell_length_b 24.6468(13) _cell_length_c 8.0601(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2547.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9059 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 31.36 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 1.004 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7733 _exptl_absorpt_correction_T_max 0.9609 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.75 _diffrn_standards_number 0 _diffrn_standards_interval_count N/A _diffrn_standards_interval_time N/A _diffrn_standards_decay_% N/A _diffrn_reflns_number 16960 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3226 _reflns_number_gt 2737 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL (XS)' _computing_structure_refinement 'Bruker SHELXTL (XL)' _computing_molecular_graphics 'Bruker SHELXTL (XP)' _computing_publication_material 'Bruker SHELXTL (XCIF)' _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. Pd(1) lies on a crystallographic mirror plane, and therefore the structural model assumes a 50:50 mixture of the two enantiomers of the complex occupying the same crystallographic position. Pd(1), Cl(1), N(1), C(1) and the p-(CF3)Ph group are in identical locations for the two enantiomers, while the other atoms have 50% occupancy for each enantiomer. Enantiomer 1 contains N2 C3 C4 C5 C6 C7A C8A C9A N3A C3A and associated hydrogens. Enantiomer 2 contains N3 C3 C7 C8 C9 C4A C5A C6A N2A C2A and associated hydrogens. ; _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^)+(0.0291P)^2^+4.2496P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3226 _refine_ls_number_parameters 210 _refine_ls_number_restraints 84 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0825 _refine_ls_wR_factor_gt 0.0782 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.009 _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 Pd1 Pd 0.488870(19) 0.2500 0.17916(3) 0.01738(9) Uani 1 2 d S . . Cl1 Cl 0.41806(6) 0.31452(3) 0.00964(9) 0.03768(19) Uani 1 1 d . . . N1 N 0.55401(16) 0.30288(9) 0.3432(3) 0.0193(4) Uani 1 1 d . . . C1 C 0.58490(17) 0.28048(10) 0.4831(3) 0.0161(5) Uani 1 1 d U . . C2 C 0.5494(6) 0.3598(4) 0.6603(14) 0.0228(17) Uani 0.50 1 d PDU A 1 H2A H 0.5981 0.3883 0.6258 0.034 Uiso 0.50 1 calc PR A 1 H2B H 0.5346 0.3636 0.7790 0.034 Uiso 0.50 1 calc PR A 1 H2C H 0.4844 0.3633 0.5972 0.034 Uiso 0.50 1 calc PR A 1 N2 N 0.5959(6) 0.3063(4) 0.6283(13) 0.0140(11) Uani 0.50 1 d PDU A 1 C4 C 0.6442(4) 0.27907(19) 0.7738(6) 0.0178(10) Uani 0.50 1 d PDU . . H4 H 0.5873 0.2695 0.8534 0.021 Uiso 0.50 1 calc PR A 1 C5 C 0.7214(11) 0.3153(5) 0.8636(18) 0.022(2) Uani 0.50 1 d PDU A . H5A H 0.6848 0.3478 0.9065 0.026 Uiso 0.50 1 calc PR B 3 H5B H 0.7757 0.3276 0.7849 0.026 Uiso 0.50 1 calc PR B 3 C6 C 0.7722(4) 0.2852(2) 1.0066(7) 0.0261(12) Uani 0.50 1 d PDU . . H6A H 0.8270 0.3084 1.0559 0.031 Uiso 0.50 1 calc PR A 5 H6B H 0.7191 0.2781 1.0932 0.031 Uiso 0.50 1 calc PR A 5 C3 C 0.5909(6) 0.3601(4) 0.6663(13) 0.0247(17) Uani 0.50 1 d PDU A 2 H3A H 0.6439 0.3861 0.6293 0.037 Uiso 0.50 1 calc PR A 2 H3B H 0.5837 0.3622 0.7872 0.037 Uiso 0.50 1 calc PR A 2 H3C H 0.5239 0.3689 0.6142 0.037 Uiso 0.50 1 calc PR A 2 N3 N 0.6223(6) 0.3052(4) 0.6190(13) 0.0140(11) Uani 0.50 1 d PDU A 2 C7 C 0.6964(4) 0.27312(19) 0.7189(6) 0.0172(10) Uani 0.50 1 d PDU . . H7 H 0.7557 0.2629 0.6446 0.021 Uiso 0.50 1 calc PR A 2 C8 C 0.7419(11) 0.3044(5) 0.8646(18) 0.021(2) Uani 0.50 1 d PDU A . H8A H 0.6856 0.3151 0.9419 0.026 Uiso 0.50 1 calc PR C 4 H8B H 0.7769 0.3377 0.8243 0.026 Uiso 0.50 1 calc PR C 4 C9 C 0.8202(5) 0.2681(2) 0.9536(7) 0.0286(14) Uani 0.50 1 d PDU . . H9A H 0.8799 0.2609 0.8789 0.034 Uiso 0.50 1 calc PR A 6 H9B H 0.8471 0.2873 1.0526 0.034 Uiso 0.50 1 calc PR A 6 C11 C 0.5776(2) 0.35871(11) 0.3106(3) 0.0227(5) Uani 1 1 d . . . C12 C 0.6812(2) 0.37432(12) 0.3068(4) 0.0298(6) Uani 1 1 d . A . H12 H 0.7346 0.3482 0.3230 0.036 Uiso 1 1 calc R . . C13 C 0.7066(2) 0.42816(13) 0.2794(4) 0.0387(8) Uani 1 1 d . . . H13 H 0.7777 0.4390 0.2779 0.046 Uiso 1 1 calc R A . C14 C 0.6291(3) 0.46601(12) 0.2541(4) 0.0343(7) Uani 1 1 d . A . C15 C 0.5259(3) 0.45043(12) 0.2557(4) 0.0368(7) Uani 1 1 d . . . H15 H 0.4726 0.4766 0.2379 0.044 Uiso 1 1 calc R A . C16 C 0.4997(2) 0.39652(12) 0.2833(4) 0.0325(7) Uani 1 1 d . A . H16 H 0.4286 0.3856 0.2834 0.039 Uiso 1 1 calc R . . C17 C 0.6566(3) 0.52484(14) 0.2326(5) 0.0502(9) Uani 1 1 d . . . F1 F 0.7540(2) 0.53250(10) 0.1903(5) 0.1109(13) Uani 1 1 d . A . F3 F 0.5972(3) 0.54970(10) 0.1242(4) 0.1110(13) Uani 1 1 d . A . F2 F 0.6439(2) 0.55326(9) 0.3710(4) 0.0814(8) Uani 1 1 d . A . 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 0.01261(13) 0.02615(16) 0.01337(13) 0.000 -0.00048(10) 0.000 Cl1 0.0399(4) 0.0440(5) 0.0291(4) 0.0144(3) -0.0160(3) -0.0026(3) N1 0.0189(10) 0.0192(11) 0.0197(10) 0.0029(8) -0.0040(8) -0.0029(8) C1 0.0119(10) 0.0171(12) 0.0194(11) 0.0011(9) 0.0015(9) -0.0003(9) C2 0.025(4) 0.014(3) 0.029(4) -0.005(2) 0.002(4) 0.006(3) N2 0.010(3) 0.0148(11) 0.0168(13) 0.0004(9) 0.002(2) 0.000(2) C4 0.017(2) 0.017(3) 0.019(2) -0.0005(19) 0.001(2) 0.001(2) C5 0.013(5) 0.032(5) 0.020(4) -0.008(4) 0.002(3) 0.000(4) C6 0.020(3) 0.038(3) 0.021(3) -0.010(2) -0.004(2) -0.004(2) C3 0.035(4) 0.018(3) 0.020(3) 0.000(2) -0.005(4) 0.006(4) N3 0.010(3) 0.0148(11) 0.0168(13) 0.0004(9) 0.002(2) 0.000(2) C7 0.013(2) 0.024(2) 0.015(2) 0.0018(18) -0.0014(19) -0.0007(19) C8 0.016(5) 0.027(5) 0.021(4) -0.007(3) -0.001(3) -0.005(4) C9 0.021(2) 0.044(4) 0.021(3) 0.003(2) -0.005(2) -0.002(2) C11 0.0269(13) 0.0226(13) 0.0188(12) 0.0048(10) -0.0040(11) -0.0034(10) C12 0.0257(13) 0.0242(15) 0.0397(16) 0.0056(12) 0.0064(12) -0.0017(11) C13 0.0304(15) 0.0278(16) 0.058(2) 0.0083(15) 0.0151(15) -0.0058(13) C14 0.0437(18) 0.0245(15) 0.0346(15) 0.0092(13) 0.0091(14) -0.0053(13) C15 0.0394(17) 0.0254(16) 0.0455(18) 0.0133(14) -0.0084(15) 0.0023(13) C16 0.0288(15) 0.0249(15) 0.0438(17) 0.0081(12) -0.0113(13) -0.0001(12) C17 0.059(2) 0.0278(18) 0.064(2) 0.0142(18) 0.015(2) -0.0046(16) F1 0.090(2) 0.0333(13) 0.210(4) 0.0202(17) 0.076(2) -0.0137(13) F3 0.166(3) 0.0427(15) 0.125(3) 0.0509(16) -0.050(2) -0.0239(18) F2 0.120(2) 0.0294(12) 0.094(2) -0.0039(12) 0.0231(18) -0.0154(13) _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 2.036(2) 7_565 ? Pd1 N1 2.036(2) . ? Pd1 Cl1 2.2848(7) . ? Pd1 Cl1 2.2848(7) 7_565 ? N1 C1 1.316(3) . ? N1 C11 1.433(3) . ? C1 N2 1.340(11) . ? C1 N3 1.343(11) . ? C1 C1 1.502(5) 7_565 ? C2 N2 1.470(9) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? N2 C4 1.487(9) . ? C4 C7 1.516(6) 7_565 ? C4 C5 1.517(11) . ? C4 H4 1.0000 . ? C5 C6 1.518(11) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C9 1.513(6) 7_565 ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C3 N3 1.462(10) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? N3 C7 1.476(8) . ? C7 C4 1.516(6) 7_565 ? C7 C8 1.521(10) . ? C7 H7 1.0000 . ? C8 C9 1.523(9) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C6 1.513(6) 7_565 ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C11 C12 1.383(4) . ? C11 C16 1.384(4) . ? C12 C13 1.384(4) . ? C12 H12 0.9500 . ? C13 C14 1.378(4) . ? C13 H13 0.9500 . ? C14 C15 1.379(4) . ? C14 C17 1.502(4) . ? C15 C16 1.388(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 F1 1.309(4) . ? C17 F3 1.310(5) . ? C17 F2 1.328(5) . ? 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 N1 79.60(12) 7_565 . ? N1 Pd1 Cl1 175.58(6) 7_565 . ? N1 Pd1 Cl1 96.08(6) . . ? N1 Pd1 Cl1 96.09(6) 7_565 7_565 ? N1 Pd1 Cl1 175.58(6) . 7_565 ? Cl1 Pd1 Cl1 88.21(4) . 7_565 ? C1 N1 C11 119.7(2) . . ? C1 N1 Pd1 114.29(17) . . ? C11 N1 Pd1 125.60(16) . . ? N1 C1 N2 125.5(4) . . ? N1 C1 N3 128.0(5) . . ? N1 C1 C1 114.80(14) . 7_565 ? N2 C1 C1 118.4(4) . 7_565 ? N3 C1 C1 117.0(4) . 7_565 ? C1 N2 C2 122.5(7) . . ? C1 N2 C4 121.2(7) . . ? C2 N2 C4 115.9(8) . . ? N2 C4 C7 109.7(5) . 7_565 ? N2 C4 C5 112.5(7) . . ? C7 C4 C5 110.5(6) 7_565 . ? N2 C4 H4 108.0 . . ? C7 C4 H4 108.0 7_565 . ? C5 C4 H4 108.0 . . ? C4 C5 C6 110.8(9) . . ? C4 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? C9 C6 C5 112.7(6) 7_565 . ? C9 C6 H6A 109.1 7_565 . ? C5 C6 H6A 109.1 . . ? C9 C6 H6B 109.1 7_565 . ? C5 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? N3 C3 H3A 109.5 . . ? N3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 N3 C3 122.3(7) . . ? C1 N3 C7 115.5(7) . . ? C3 N3 C7 122.1(8) . . ? N3 C7 C4 109.3(5) . 7_565 ? N3 C7 C8 113.4(7) . . ? C4 C7 C8 112.0(7) 7_565 . ? N3 C7 H7 107.3 . . ? C4 C7 H7 107.3 7_565 . ? C8 C7 H7 107.3 . . ? C7 C8 C9 108.6(7) . . ? C7 C8 H8A 110.0 . . ? C9 C8 H8A 110.0 . . ? C7 C8 H8B 110.0 . . ? C9 C8 H8B 110.0 . . ? H8A C8 H8B 108.3 . . ? C6 C9 C8 111.9(7) 7_565 . ? C6 C9 H9A 109.2 7_565 . ? C8 C9 H9A 109.2 . . ? C6 C9 H9B 109.2 7_565 . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C12 C11 C16 120.2(3) . . ? C12 C11 N1 118.3(2) . . ? C16 C11 N1 121.5(2) . . ? C11 C12 C13 119.8(3) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C14 C13 C12 120.1(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 120.2(3) . . ? C13 C14 C17 120.1(3) . . ? C15 C14 C17 119.7(3) . . ? C14 C15 C16 120.0(3) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C11 C16 C15 119.7(3) . . ? C11 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? F1 C17 F3 108.3(3) . . ? F1 C17 F2 105.1(4) . . ? F3 C17 F2 104.0(3) . . ? F1 C17 C14 113.2(3) . . ? F3 C17 C14 113.1(3) . . ? F2 C17 C14 112.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Pd1 N1 C1 -12.9(2) 7_565 . . . ? Cl1 Pd1 N1 C1 166.18(16) . . . . ? N1 Pd1 N1 C11 160.12(17) 7_565 . . . ? Cl1 Pd1 N1 C11 -20.8(2) . . . . ? C11 N1 C1 N2 31.0(5) . . . . ? Pd1 N1 C1 N2 -155.6(5) . . . . ? C11 N1 C1 N3 12.6(5) . . . . ? Pd1 N1 C1 N3 -174.0(4) . . . . ? C11 N1 C1 C1 -162.57(17) . . . 7_565 ? Pd1 N1 C1 C1 10.86(17) . . . 7_565 ? N1 C1 N2 C2 16.2(10) . . . . ? N3 C1 N2 C2 121(4) . . . . ? C1 C1 N2 C2 -149.8(6) 7_565 . . . ? N1 C1 N2 C4 -172.0(5) . . . . ? N3 C1 N2 C4 -67(3) . . . . ? C1 C1 N2 C4 21.9(8) 7_565 . . . ? C1 N2 C4 C7 12.4(9) . . . 7_565 ? C2 N2 C4 C7 -175.3(6) . . . 7_565 ? C1 N2 C4 C5 135.9(9) . . . . ? C2 N2 C4 C5 -51.9(10) . . . . ? N2 C4 C5 C6 -177.6(8) . . . . ? C7 C4 C5 C6 -54.6(12) 7_565 . . . ? C4 C5 C6 C9 53.2(12) . . . 7_565 ? N1 C1 N3 C3 29.9(10) . . . . ? N2 C1 N3 C3 -56(3) . . . . ? C1 C1 N3 C3 -155.0(7) 7_565 . . . ? N1 C1 N3 C7 -150.8(5) . . . . ? N2 C1 N3 C7 123(3) . . . . ? C1 C1 N3 C7 24.3(8) 7_565 . . . ? C1 N3 C7 C4 -58.3(8) . . . 7_565 ? C3 N3 C7 C4 121.0(8) . . . 7_565 ? C1 N3 C7 C8 176.1(9) . . . . ? C3 N3 C7 C8 -4.7(13) . . . . ? N3 C7 C8 C9 -177.6(8) . . . . ? C4 C7 C8 C9 58.2(12) 7_565 . . . ? C7 C8 C9 C6 -55.5(12) . . . 7_565 ? C1 N1 C11 C12 59.4(3) . . . . ? Pd1 N1 C11 C12 -113.2(2) . . . . ? C1 N1 C11 C16 -120.6(3) . . . . ? Pd1 N1 C11 C16 66.8(3) . . . . ? C16 C11 C12 C13 1.5(4) . . . . ? N1 C11 C12 C13 -178.6(3) . . . . ? C11 C12 C13 C14 -0.7(5) . . . . ? C12 C13 C14 C15 -0.2(5) . . . . ? C12 C13 C14 C17 177.0(3) . . . . ? C13 C14 C15 C16 0.2(5) . . . . ? C17 C14 C15 C16 -177.0(3) . . . . ? C12 C11 C16 C15 -1.4(5) . . . . ? N1 C11 C16 C15 178.6(3) . . . . ? C14 C15 C16 C11 0.6(5) . . . . ? C13 C14 C17 F1 19.6(5) . . . . ? C15 C14 C17 F1 -163.2(4) . . . . ? C13 C14 C17 F3 143.2(4) . . . . ? C15 C14 C17 F3 -39.6(5) . . . . ? C13 C14 C17 F2 -99.3(4) . . . . ? C15 C14 C17 F2 77.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.743 _refine_diff_density_min -0.585 _refine_diff_density_rms 0.088 _exptl_crystal_recrystallization_method 'slow evap of DMSO soln' #===end data_slaughter_cmpd_5 _database_code_depnum_ccdc_archive 'CCDC 625248' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common '1,2-diaminocyclohexane p-CF3 phenyl bis(amidine)' _chemical_melting_point 452-455 _chemical_formula_moiety 'C24 H24 F6 N4' _chemical_formula_sum 'C24 H24 F6 N4' _chemical_formula_weight 482.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.1121(3) _cell_length_b 11.9950(5) _cell_length_c 26.9486(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.481(3) _cell_angle_gamma 90.00 _cell_volume 2298.89(17) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3826 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 21.86 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9802 _exptl_absorpt_correction_T_max 0.9860 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.75 _diffrn_standards_number 0 _diffrn_standards_interval_count N/A _diffrn_standards_interval_time N/A _diffrn_standards_decay_% N/A _diffrn_reflns_number 11851 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 21.96 _reflns_number_total 2813 _reflns_number_gt 2036 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL (XS)' _computing_structure_refinement 'Bruker SHELXTL (XL)' _computing_molecular_graphics 'Bruker SHELXTL (XP)' _computing_publication_material 'Bruker SHELXTL (XCIF)' _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. Crystal was modeled as a two-component pseudo-merohedral twin. Twin law: 1.00 0.00 0.00 0.00 -1.00 0.00 0.00 0.00 -1.00 Refined proportions of twin components: 0.82, 0.18 ; _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^)+(0.0671P)^2^+0.7288P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0039(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2813 _refine_ls_number_parameters 367 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1363 _refine_ls_wR_factor_gt 0.1175 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.003 _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 0.3173(5) 1.0051(3) 0.25662(14) 0.0533(10) Uani 1 1 d . . . C2 C 0.1684(5) 0.9152(3) 0.25461(14) 0.0528(10) Uani 1 1 d . . . N1 N 0.3507(5) 1.0747(2) 0.22136(12) 0.0585(9) Uani 1 1 d . . . N2 N 0.1437(5) 0.8474(2) 0.21806(12) 0.0573(9) Uani 1 1 d . . . N3 N 0.4228(5) 1.0046(3) 0.29890(12) 0.0631(9) Uani 1 1 d . . . N4 N 0.0552(5) 0.9137(3) 0.29445(12) 0.0631(9) Uani 1 1 d . . . C3 C 0.5800(6) 1.0824(4) 0.30145(17) 0.0799(13) Uani 1 1 d . . . H3A H 0.6478 1.0803 0.2708 0.120 Uiso 1 1 calc R . . H3B H 0.6625 1.0616 0.3283 0.120 Uiso 1 1 calc R . . H3C H 0.5334 1.1564 0.3069 0.120 Uiso 1 1 calc R . . C4 C -0.1009(6) 0.8342(3) 0.29330(17) 0.0783(13) Uani 1 1 d . . . H4A H -0.1637 0.8381 0.2617 0.118 Uiso 1 1 calc R . . H4B H -0.1882 0.8521 0.3191 0.118 Uiso 1 1 calc R . . H4C H -0.0533 0.7601 0.2984 0.118 Uiso 1 1 calc R . . C5 C 0.3373(7) 0.9540(3) 0.34382(14) 0.0663(12) Uani 1 1 d . . . H5 H 0.3665 0.8742 0.3436 0.080 Uiso 1 1 calc R . . C6 C 0.1258(6) 0.9664(3) 0.34044(15) 0.0669(12) Uani 1 1 d . . . H6 H 0.0970 1.0462 0.3386 0.080 Uiso 1 1 calc R . . C7 C 0.4162(8) 1.0031(4) 0.39173(17) 0.0961(17) Uani 1 1 d . . . H7A H 0.5496 0.9868 0.3940 0.115 Uiso 1 1 calc R . . H7B H 0.4012 1.0834 0.3911 0.115 Uiso 1 1 calc R . . C8 C 0.0305(8) 0.9199(4) 0.38642(16) 0.0894(15) Uani 1 1 d . . . H8A H 0.0482 0.8398 0.3876 0.107 Uiso 1 1 calc R . . H8B H -0.1034 0.9346 0.3844 0.107 Uiso 1 1 calc R . . C9 C 0.3179(11) 0.9560(5) 0.43703(19) 0.122(2) Uani 1 1 d . . . H9A H 0.3455 0.8771 0.4399 0.146 Uiso 1 1 calc R . . H9B H 0.3656 0.9928 0.4666 0.146 Uiso 1 1 calc R . . C10 C 0.1108(11) 0.9721(5) 0.43360(19) 0.119(2) Uani 1 1 d . . . H10A H 0.0825 1.0513 0.4339 0.142 Uiso 1 1 calc R . . H10B H 0.0517 0.9386 0.4623 0.142 Uiso 1 1 calc R . . C11 C 0.2243(6) 1.0896(3) 0.18179(14) 0.0526(10) Uani 1 1 d . . . C12 C 0.0332(6) 1.1058(3) 0.18816(16) 0.0639(11) Uani 1 1 d . . . H12 H -0.0162 1.1035 0.2200 0.077 Uiso 1 1 calc R . . C13 C -0.0855(6) 1.1254(3) 0.14840(16) 0.0683(12) Uani 1 1 d . . . H14 H -0.2138 1.1338 0.1537 0.082 Uiso 1 1 calc R . . C14 C -0.0157(6) 1.1327(3) 0.10089(15) 0.0613(11) Uani 1 1 d . A . C15 C 0.1747(7) 1.1188(3) 0.09415(15) 0.0676(12) Uani 1 1 d . . . H15 H 0.2239 1.1236 0.0623 0.081 Uiso 1 1 calc R . . C16 C 0.2934(6) 1.0981(3) 0.13376(15) 0.0631(11) Uani 1 1 d . . . H16 H 0.4216 1.0896 0.1283 0.076 Uiso 1 1 calc R . . C17 C -0.1469(9) 1.1564(5) 0.0587(2) 0.0877(15) Uani 1 1 d D . . F1 F -0.0912(13) 1.1148(16) 0.0169(3) 0.133(6) Uani 0.64(2) 1 d PD A 1 F2 F -0.3121(10) 1.1184(11) 0.0639(3) 0.107(4) Uani 0.64(2) 1 d PD A 1 F3 F -0.169(2) 1.2636(7) 0.0509(8) 0.166(9) Uani 0.64(2) 1 d PD A 1 F1A F -0.276(5) 1.229(3) 0.0690(7) 0.21(2) Uani 0.36(2) 1 d PD A 2 F2A F -0.058(2) 1.206(3) 0.0220(6) 0.139(9) Uani 0.36(2) 1 d PD A 2 F3A F -0.227(7) 1.0733(13) 0.0381(14) 0.29(2) Uani 0.36(2) 1 d PD A 2 C21 C 0.2745(6) 0.8354(3) 0.18000(14) 0.0518(10) Uani 1 1 d . . . C22 C 0.4649(6) 0.8206(3) 0.18897(15) 0.0587(11) Uani 1 1 d . . . H22 H 0.5101 0.8218 0.2215 0.070 Uiso 1 1 calc R . . C23 C 0.5870(6) 0.8044(3) 0.15105(15) 0.0674(12) Uani 1 1 d . . . H23 H 0.7147 0.7963 0.1578 0.081 Uiso 1 1 calc R . . C24 C 0.5232(6) 0.7997(3) 0.10267(14) 0.0604(11) Uani 1 1 d . B . C25 C 0.3334(7) 0.8112(3) 0.09315(15) 0.0673(12) Uani 1 1 d . . . H25 H 0.2885 0.8071 0.0607 0.081 Uiso 1 1 calc R . . C26 C 0.2103(6) 0.8286(3) 0.13143(15) 0.0635(11) Uani 1 1 d . . . H26 H 0.0825 0.8360 0.1246 0.076 Uiso 1 1 calc R . . C27 C 0.6586(8) 0.7816(5) 0.06165(19) 0.0845(14) Uani 1 1 d D . . F4 F 0.8009(11) 0.8506(9) 0.0642(4) 0.105(4) Uani 0.60(2) 1 d PD B 3 F5 F 0.736(2) 0.6823(7) 0.0644(6) 0.160(7) Uani 0.60(2) 1 d PD B 3 F6 F 0.5927(17) 0.7912(18) 0.0176(4) 0.134(7) Uani 0.60(2) 1 d PD B 3 F4A F 0.568(3) 0.744(2) 0.0221(7) 0.135(9) Uani 0.40(2) 1 d PD B 4 F5A F 0.725(7) 0.8745(14) 0.0436(12) 0.270(17) Uani 0.40(2) 1 d PD B 4 F6A F 0.791(4) 0.712(3) 0.0697(6) 0.206(15) Uani 0.40(2) 1 d PD B 4 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 0.054(3) 0.050(2) 0.055(3) -0.007(2) -0.002(2) 0.0046(19) C2 0.051(2) 0.049(2) 0.058(3) 0.006(2) 0.002(2) -0.0012(19) N1 0.063(2) 0.0478(18) 0.064(2) 0.0022(17) -0.0043(19) -0.0063(16) N2 0.061(2) 0.0503(19) 0.060(2) -0.0008(17) 0.0013(18) -0.0093(16) N3 0.065(2) 0.058(2) 0.066(2) -0.0017(17) -0.0114(19) -0.0036(18) N4 0.064(2) 0.063(2) 0.062(2) -0.0002(17) 0.0109(19) -0.0039(18) C3 0.068(3) 0.073(3) 0.098(3) 0.000(2) -0.024(3) -0.004(2) C4 0.069(3) 0.072(3) 0.095(3) 0.005(2) 0.023(3) -0.006(2) C5 0.083(3) 0.058(2) 0.058(3) 0.001(2) -0.004(2) 0.016(2) C6 0.082(4) 0.053(2) 0.066(3) 0.005(2) 0.009(2) 0.019(2) C7 0.125(5) 0.095(3) 0.068(3) -0.008(3) -0.023(3) 0.019(3) C8 0.110(4) 0.089(3) 0.070(3) 0.014(3) 0.024(3) 0.030(3) C9 0.176(7) 0.131(5) 0.057(3) -0.004(3) -0.016(4) 0.025(5) C10 0.170(7) 0.122(5) 0.064(4) 0.004(3) 0.020(4) 0.047(4) C11 0.056(3) 0.040(2) 0.061(3) 0.0012(18) 0.005(2) -0.0056(19) C12 0.065(3) 0.064(3) 0.063(3) 0.002(2) 0.011(2) 0.008(2) C13 0.060(3) 0.073(3) 0.072(3) 0.001(2) 0.003(3) 0.013(2) C14 0.062(3) 0.064(3) 0.058(3) 0.005(2) 0.002(2) 0.005(2) C15 0.076(3) 0.069(3) 0.057(3) 0.011(2) 0.011(2) -0.002(2) C16 0.058(3) 0.066(3) 0.066(3) 0.010(2) 0.010(2) -0.002(2) C17 0.092(5) 0.100(5) 0.072(4) 0.015(3) 0.002(3) 0.007(4) F1 0.103(7) 0.234(17) 0.063(4) 0.005(6) 0.002(4) 0.038(8) F2 0.064(5) 0.173(11) 0.082(5) 0.010(5) -0.016(3) -0.022(5) F3 0.166(14) 0.097(6) 0.23(2) 0.057(9) -0.086(12) 0.005(7) F1A 0.18(3) 0.32(5) 0.116(11) -0.03(2) -0.043(14) 0.18(3) F2A 0.140(13) 0.18(2) 0.097(10) 0.055(12) -0.033(9) -0.007(14) F3A 0.51(6) 0.095(10) 0.27(4) -0.012(17) -0.27(4) -0.05(2) C21 0.055(3) 0.044(2) 0.057(3) -0.0019(18) 0.003(2) -0.0070(18) C22 0.060(3) 0.064(3) 0.051(2) -0.0049(19) -0.008(2) 0.004(2) C23 0.063(3) 0.078(3) 0.061(3) -0.006(2) -0.005(3) 0.009(2) C24 0.064(3) 0.061(3) 0.056(3) -0.0046(19) 0.003(2) -0.001(2) C25 0.075(3) 0.075(3) 0.052(3) -0.002(2) -0.008(3) -0.006(2) C26 0.055(3) 0.073(3) 0.062(3) -0.004(2) -0.009(2) -0.007(2) C27 0.087(4) 0.100(4) 0.067(4) -0.004(3) 0.007(3) -0.003(4) F4 0.073(5) 0.155(9) 0.088(5) 0.002(4) 0.025(4) -0.036(4) F5 0.202(13) 0.094(6) 0.185(13) 0.011(5) 0.104(10) 0.063(6) F6 0.080(5) 0.27(2) 0.052(5) 0.005(7) -0.002(4) -0.001(8) F4A 0.176(17) 0.145(12) 0.084(11) -0.045(9) 0.036(9) -0.016(10) F5A 0.48(4) 0.123(11) 0.21(2) -0.046(12) 0.23(3) -0.095(19) F6A 0.124(12) 0.41(4) 0.082(9) 0.037(14) 0.021(7) 0.141(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 N1 1.288(4) . ? C1 N3 1.359(4) . ? C1 C2 1.512(5) . ? C2 N2 1.289(4) . ? C2 N4 1.347(5) . ? N1 C11 1.400(5) . ? N2 C21 1.398(5) . ? N3 C3 1.457(5) . ? N3 C5 1.489(5) . ? N4 C4 1.464(5) . ? N4 C6 1.476(5) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.513(6) . ? C5 C7 1.522(6) . ? C5 H5 0.9800 . ? C6 C8 1.523(6) . ? C6 H6 0.9800 . ? C7 C9 1.520(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C10 1.524(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.488(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.386(5) . ? C11 C16 1.392(5) . ? C12 C13 1.378(5) . ? C12 H12 0.9300 . ? C13 C14 1.380(5) . ? C13 H14 0.9300 . ? C14 C15 1.378(6) . ? C14 C17 1.491(6) . ? C15 C16 1.378(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 F2 1.269(8) . ? C17 F3A 1.273(11) . ? C17 F1A 1.294(12) . ? C17 F1 1.297(9) . ? C17 F3 1.312(9) . ? C17 F2A 1.320(11) . ? C21 C22 1.385(5) . ? C21 C26 1.385(5) . ? C22 C23 1.361(5) . ? C22 H22 0.9300 . ? C23 C24 1.378(5) . ? C23 H23 0.9300 . ? C24 C25 1.379(6) . ? C24 C27 1.488(6) . ? C25 C26 1.375(6) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 F6A 1.274(12) . ? C27 F6 1.279(9) . ? C27 F5A 1.305(12) . ? C27 F4 1.308(9) . ? C27 F5 1.313(9) . ? C27 F4A 1.320(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N3 121.2(4) . . ? N1 C1 C2 124.7(3) . . ? N3 C1 C2 114.1(3) . . ? N2 C2 N4 121.4(4) . . ? N2 C2 C1 124.7(4) . . ? N4 C2 C1 113.8(3) . . ? C1 N1 C11 121.6(3) . . ? C2 N2 C21 122.6(3) . . ? C1 N3 C3 117.1(3) . . ? C1 N3 C5 117.2(3) . . ? C3 N3 C5 122.8(3) . . ? C2 N4 C4 116.8(3) . . ? C2 N4 C6 117.5(3) . . ? C4 N4 C6 123.3(3) . . ? N3 C3 H3A 109.5 . . ? N3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N4 C4 H4A 109.5 . . ? N4 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N4 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 C6 108.9(3) . . ? N3 C5 C7 112.4(4) . . ? C6 C5 C7 111.9(4) . . ? N3 C5 H5 107.8 . . ? C6 C5 H5 107.8 . . ? C7 C5 H5 107.8 . . ? N4 C6 C5 109.8(3) . . ? N4 C6 C8 112.1(4) . . ? C5 C6 C8 111.3(4) . . ? N4 C6 H6 107.8 . . ? C5 C6 H6 107.8 . . ? C8 C6 H6 107.8 . . ? C9 C7 C5 111.6(5) . . ? C9 C7 H7A 109.3 . . ? C5 C7 H7A 109.3 . . ? C9 C7 H7B 109.3 . . ? C5 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C6 C8 C10 111.2(5) . . ? C6 C8 H8A 109.4 . . ? C10 C8 H8A 109.4 . . ? C6 C8 H8B 109.4 . . ? C10 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C10 C9 C7 111.3(5) . . ? C10 C9 H9A 109.4 . . ? C7 C9 H9A 109.4 . . ? C10 C9 H9B 109.4 . . ? C7 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C9 C10 C8 111.2(5) . . ? C9 C10 H10A 109.4 . . ? C8 C10 H10A 109.4 . . ? C9 C10 H10B 109.4 . . ? C8 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C16 117.3(4) . . ? C12 C11 N1 123.2(4) . . ? C16 C11 N1 119.2(4) . . ? C13 C12 C11 121.5(4) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C14 120.6(4) . . ? C12 C13 H14 119.7 . . ? C14 C13 H14 119.7 . . ? C15 C14 C13 118.4(4) . . ? C15 C14 C17 122.1(4) . . ? C13 C14 C17 119.5(4) . . ? C14 C15 C16 121.1(4) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C15 C16 C11 121.0(4) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? F2 C17 F3A 50(2) . . ? F2 C17 F1A 63.9(19) . . ? F3A C17 F1A 107.8(15) . . ? F2 C17 F1 104.2(7) . . ? F3A C17 F1 57.2(19) . . ? F1A C17 F1 131.7(10) . . ? F2 C17 F3 105.2(8) . . ? F3A C17 F3 130.2(11) . . ? F1A C17 F3 45.1(15) . . ? F1 C17 F3 105.8(8) . . ? F2 C17 F2A 134.0(8) . . ? F3A C17 F2A 103.9(15) . . ? F1A C17 F2A 101.8(13) . . ? F1 C17 F2A 50.9(10) . . ? F3 C17 F2A 59.8(9) . . ? F2 C17 C14 114.9(5) . . ? F3A C17 C14 117.2(10) . . ? F1A C17 C14 113.9(10) . . ? F1 C17 C14 113.3(6) . . ? F3 C17 C14 112.4(7) . . ? F2A C17 C14 110.8(8) . . ? C22 C21 C26 118.1(4) . . ? C22 C21 N2 122.7(4) . . ? C26 C21 N2 118.9(4) . . ? C23 C22 C21 121.1(4) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C22 C23 C24 120.6(4) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C23 C24 C25 119.1(4) . . ? C23 C24 C27 119.9(4) . . ? C25 C24 C27 121.0(4) . . ? C26 C25 C24 120.3(4) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C25 C26 C21 120.7(4) . . ? C25 C26 H26 119.6 . . ? C21 C26 H26 119.6 . . ? F6A C27 F6 118.7(12) . . ? F6A C27 F5A 110.7(16) . . ? F6 C27 F5A 73.0(17) . . ? F6A C27 F4 80.6(16) . . ? F6 C27 F4 105.6(9) . . ? F6 C27 F5 106.5(10) . . ? F5A C27 F5 130.1(18) . . ? F4 C27 F5 104.4(9) . . ? F6A C27 F4A 105.4(13) . . ? F5A C27 F4A 99.5(15) . . ? F4 C27 F4A 129.0(13) . . ? F5 C27 F4A 86.3(12) . . ? F6A C27 C24 116.8(10) . . ? F6 C27 C24 116.3(7) . . ? F5A C27 C24 113.0(10) . . ? F4 C27 C24 112.0(6) . . ? F5 C27 C24 111.3(7) . . ? F4A C27 C24 109.7(12) . . ? 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 N1 C1 C2 N2 47.9(5) . . . . ? N3 C1 C2 N2 -129.4(4) . . . . ? N1 C1 C2 N4 -129.8(4) . . . . ? N3 C1 C2 N4 52.9(4) . . . . ? N3 C1 N1 C11 -168.5(3) . . . . ? C2 C1 N1 C11 14.4(5) . . . . ? N4 C2 N2 C21 -170.0(3) . . . . ? C1 C2 N2 C21 12.4(5) . . . . ? N1 C1 N3 C3 -2.9(5) . . . . ? C2 C1 N3 C3 174.5(3) . . . . ? N1 C1 N3 C5 158.2(3) . . . . ? C2 C1 N3 C5 -24.4(4) . . . . ? N2 C2 N4 C4 -2.2(5) . . . . ? C1 C2 N4 C4 175.6(3) . . . . ? N2 C2 N4 C6 160.9(3) . . . . ? C1 C2 N4 C6 -21.3(4) . . . . ? C1 N3 C5 C6 -28.4(4) . . . . ? C3 N3 C5 C6 131.5(4) . . . . ? C1 N3 C5 C7 -153.0(4) . . . . ? C3 N3 C5 C7 6.9(5) . . . . ? C2 N4 C6 C5 -31.9(4) . . . . ? C4 N4 C6 C5 129.9(4) . . . . ? C2 N4 C6 C8 -156.3(3) . . . . ? C4 N4 C6 C8 5.6(5) . . . . ? N3 C5 C6 N4 57.4(4) . . . . ? C7 C5 C6 N4 -177.7(3) . . . . ? N3 C5 C6 C8 -177.8(3) . . . . ? C7 C5 C6 C8 -52.9(5) . . . . ? N3 C5 C7 C9 176.2(4) . . . . ? C6 C5 C7 C9 53.2(5) . . . . ? N4 C6 C8 C10 177.8(4) . . . . ? C5 C6 C8 C10 54.3(5) . . . . ? C5 C7 C9 C10 -55.2(6) . . . . ? C7 C9 C10 C8 56.7(7) . . . . ? C6 C8 C10 C9 -56.5(6) . . . . ? C1 N1 C11 C12 48.3(5) . . . . ? C1 N1 C11 C16 -137.3(4) . . . . ? C16 C11 C12 C13 2.5(6) . . . . ? N1 C11 C12 C13 176.9(3) . . . . ? C11 C12 C13 C14 -2.0(6) . . . . ? C12 C13 C14 C15 0.7(6) . . . . ? C12 C13 C14 C17 -178.7(4) . . . . ? C13 C14 C15 C16 0.0(6) . . . . ? C17 C14 C15 C16 179.4(4) . . . . ? C14 C15 C16 C11 0.5(6) . . . . ? C12 C11 C16 C15 -1.7(5) . . . . ? N1 C11 C16 C15 -176.4(3) . . . . ? C15 C14 C17 F2 149.0(8) . . . . ? C13 C14 C17 F2 -31.7(10) . . . . ? C15 C14 C17 F3A 93(3) . . . . ? C13 C14 C17 F3A -88(3) . . . . ? C15 C14 C17 F1A -140(3) . . . . ? C13 C14 C17 F1A 39(3) . . . . ? C15 C14 C17 F1 29.3(12) . . . . ? C13 C14 C17 F1 -151.4(10) . . . . ? C15 C14 C17 F3 -90.6(14) . . . . ? C13 C14 C17 F3 88.7(14) . . . . ? C15 C14 C17 F2A -25.8(19) . . . . ? C13 C14 C17 F2A 153.5(18) . . . . ? C2 N2 C21 C22 48.4(5) . . . . ? C2 N2 C21 C26 -137.2(4) . . . . ? C26 C21 C22 C23 2.6(6) . . . . ? N2 C21 C22 C23 177.1(3) . . . . ? C21 C22 C23 C24 -1.5(6) . . . . ? C22 C23 C24 C25 -0.3(6) . . . . ? C22 C23 C24 C27 -179.9(4) . . . . ? C23 C24 C25 C26 0.9(6) . . . . ? C27 C24 C25 C26 -179.5(4) . . . . ? C24 C25 C26 C21 0.2(6) . . . . ? C22 C21 C26 C25 -2.0(6) . . . . ? N2 C21 C26 C25 -176.7(3) . . . . ? C23 C24 C27 F6A 40(2) . . . . ? C25 C24 C27 F6A -139.8(19) . . . . ? C23 C24 C27 F6 -172.1(12) . . . . ? C25 C24 C27 F6 8.4(13) . . . . ? C23 C24 C27 F5A -90(3) . . . . ? C25 C24 C27 F5A 90(3) . . . . ? C23 C24 C27 F4 -50.6(8) . . . . ? C25 C24 C27 F4 129.9(7) . . . . ? C23 C24 C27 F5 65.7(10) . . . . ? C25 C24 C27 F5 -113.8(10) . . . . ? C23 C24 C27 F4A 159.5(14) . . . . ? C25 C24 C27 F4A -20.0(15) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 21.96 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.131 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.035 _exptl_crystal_recrystallization_method 'slow evap of cyclohexane solution'