# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Han Vinh Huynh' 'Ramasamy Jothibasu' _publ_contact_author_name 'Han Vinh Huynh' _publ_contact_author_email CHMHHV@NUS.EDU.SG _publ_section_title ; Versatile coordination chemistry of indazole-derived carbenes ; # Attachment '3b.cif' data_8603 _database_code_depnum_ccdc_archive 'CCDC 757866' #TrackingRef '3b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H29 I2 N2 P Pd' _chemical_formula_weight 796.71 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' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.4399(10) _cell_length_b 15.6813(14) _cell_length_c 16.1726(14) _cell_angle_alpha 90.00 _cell_angle_beta 99.776(2) _cell_angle_gamma 90.00 _cell_volume 2859.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3404 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 24.27 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.851 _exptl_crystal_density_method ? _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 2.885 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5443 _exptl_absorpt_correction_T_max 0.8459 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19912 _diffrn_reflns_av_R_equivalents 0.0511 _diffrn_reflns_av_sigmaI/netI 0.0585 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6546 _reflns_number_gt 5444 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+8.8297P] 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 6546 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1216 _refine_ls_wR_factor_gt 0.1156 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.15320(4) 0.18404(3) 0.67758(3) 0.01740(11) Uani 1 1 d . . . I1 I 0.16953(4) 0.09252(3) 0.81530(3) 0.03485(13) Uani 1 1 d . . . I2 I 0.33567(4) 0.10486(3) 0.63054(3) 0.03652(13) Uani 1 1 d . . . P1 P 0.12123(12) 0.26394(9) 0.55800(9) 0.0176(3) Uani 1 1 d . . . N1 N 0.0297(4) 0.3122(3) 0.7648(3) 0.0241(11) Uani 1 1 d . . . N2 N -0.0798(4) 0.3406(3) 0.7805(3) 0.0296(12) Uani 1 1 d . . . C1 C 0.0184(5) 0.2428(4) 0.7171(3) 0.0203(11) Uani 1 1 d . . . C2 C -0.1049(5) 0.2247(4) 0.6993(4) 0.0253(13) Uani 1 1 d . . . C3 C -0.1723(6) 0.1631(5) 0.6500(5) 0.0375(16) Uani 1 1 d . . . H3 H -0.1354 0.1200 0.6233 0.045 Uiso 1 1 calc R . . C4 C -0.2932(7) 0.1670(5) 0.6413(6) 0.051(2) Uani 1 1 d . . . H4 H -0.3398 0.1262 0.6082 0.061 Uiso 1 1 calc R . . C5 C -0.3482(6) 0.2311(6) 0.6811(6) 0.052(2) Uani 1 1 d . . . H5 H -0.4315 0.2319 0.6742 0.062 Uiso 1 1 calc R . . C6 C -0.2860(6) 0.2919(5) 0.7291(5) 0.0414(18) Uani 1 1 d . . . H6 H -0.3246 0.3348 0.7548 0.050 Uiso 1 1 calc R . . C7 C -0.1623(5) 0.2884(4) 0.7392(4) 0.0292(14) Uani 1 1 d . . . C8 C 0.1400(6) 0.3536(4) 0.8053(4) 0.0315(14) Uani 1 1 d . . . H8A H 0.1336 0.4152 0.7950 0.038 Uiso 1 1 calc R . . H8B H 0.2060 0.3323 0.7796 0.038 Uiso 1 1 calc R . . C9 C 0.1674(7) 0.3380(5) 0.8989(4) 0.0433(18) Uani 1 1 d . . . H9A H 0.1086 0.3665 0.9259 0.065 Uiso 1 1 calc R . . H9B H 0.2455 0.3604 0.9211 0.065 Uiso 1 1 calc R . . H9C H 0.1657 0.2773 0.9098 0.065 Uiso 1 1 calc R . . C10 C -0.1017(6) 0.4247(4) 0.8158(5) 0.0370(16) Uani 1 1 d . . . H10A H -0.1634 0.4542 0.7767 0.044 Uiso 1 1 calc R . . H10B H -0.0290 0.4588 0.8209 0.044 Uiso 1 1 calc R . . C11 C -0.1393(9) 0.4195(5) 0.8995(6) 0.062(3) Uani 1 1 d . . . H11A H -0.2133 0.3883 0.8944 0.093 Uiso 1 1 calc R . . H11B H -0.1502 0.4766 0.9200 0.093 Uiso 1 1 calc R . . H11C H -0.0787 0.3903 0.9386 0.093 Uiso 1 1 calc R . . C1A C 0.0233(5) 0.3552(4) 0.5641(3) 0.0211(12) Uani 1 1 d . . . C2A C 0.0693(6) 0.4308(4) 0.6014(4) 0.0282(13) Uani 1 1 d . . . H2A H 0.1519 0.4377 0.6156 0.034 Uiso 1 1 calc R . . C3A C -0.0051(7) 0.4959(4) 0.6179(5) 0.0428(18) Uani 1 1 d . . . H3A H 0.0265 0.5459 0.6450 0.051 Uiso 1 1 calc R . . C4A C -0.1248(7) 0.4869(5) 0.5945(5) 0.047(2) Uani 1 1 d . . . H4A H -0.1754 0.5314 0.6049 0.057 Uiso 1 1 calc R . . C5A C -0.1727(6) 0.4133(5) 0.5558(4) 0.0416(19) Uani 1 1 d . . . H5A H -0.2552 0.4082 0.5393 0.050 Uiso 1 1 calc R . . C6A C -0.0991(5) 0.3477(4) 0.5415(4) 0.0287(13) Uani 1 1 d . . . H6A H -0.1318 0.2972 0.5162 0.034 Uiso 1 1 calc R . . C1B C 0.0497(5) 0.2054(4) 0.4661(4) 0.0201(11) Uani 1 1 d . . . C2B C -0.0028(5) 0.2485(4) 0.3940(4) 0.0268(13) Uani 1 1 d . . . H2B H -0.0046 0.3084 0.3935 0.032 Uiso 1 1 calc R . . C3B C -0.0523(5) 0.2036(4) 0.3230(4) 0.0288(14) Uani 1 1 d . . . H3B H -0.0877 0.2329 0.2744 0.035 Uiso 1 1 calc R . . C4B C -0.0496(6) 0.1152(4) 0.3237(4) 0.0320(15) Uani 1 1 d . . . H4B H -0.0833 0.0846 0.2755 0.038 Uiso 1 1 calc R . . C5B C 0.0015(6) 0.0724(4) 0.3938(4) 0.0337(15) Uani 1 1 d . . . H5B H 0.0028 0.0125 0.3937 0.040 Uiso 1 1 calc R . . C6B C 0.0515(5) 0.1163(4) 0.4650(4) 0.0267(13) Uani 1 1 d . . . H6B H 0.0869 0.0862 0.5130 0.032 Uiso 1 1 calc R . . C1C C 0.2556(5) 0.3100(4) 0.5289(4) 0.0207(11) Uani 1 1 d . . . C2C C 0.2799(5) 0.3070(4) 0.4469(4) 0.0260(13) Uani 1 1 d . . . H2C H 0.2268 0.2798 0.4043 0.031 Uiso 1 1 calc R . . C3C C 0.3822(6) 0.3443(4) 0.4287(4) 0.0319(15) Uani 1 1 d . . . H3C H 0.3987 0.3417 0.3738 0.038 Uiso 1 1 calc R . . C4C C 0.4598(6) 0.3850(4) 0.4904(4) 0.0345(15) Uani 1 1 d . . . H4C H 0.5279 0.4116 0.4771 0.041 Uiso 1 1 calc R . . C5C C 0.4380(6) 0.3868(4) 0.5720(5) 0.0353(16) Uani 1 1 d . . . H5C H 0.4921 0.4136 0.6143 0.042 Uiso 1 1 calc R . . C6C C 0.3361(5) 0.3490(4) 0.5911(4) 0.0280(13) Uani 1 1 d . . . H6C H 0.3217 0.3500 0.6466 0.034 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 0.0164(2) 0.0197(2) 0.0158(2) 0.00244(16) 0.00212(16) 0.00330(16) I1 0.0475(3) 0.0344(2) 0.0243(2) 0.01198(17) 0.01077(19) 0.0131(2) I2 0.0332(2) 0.0397(3) 0.0383(3) 0.00457(19) 0.0107(2) 0.01201(19) P1 0.0173(7) 0.0195(7) 0.0157(7) 0.0030(5) 0.0017(5) 0.0009(6) N1 0.026(3) 0.026(3) 0.021(2) 0.000(2) 0.009(2) 0.007(2) N2 0.025(3) 0.032(3) 0.035(3) 0.000(2) 0.013(2) 0.008(2) C1 0.021(3) 0.024(3) 0.017(3) 0.004(2) 0.008(2) 0.004(2) C2 0.021(3) 0.035(3) 0.021(3) 0.007(2) 0.006(2) 0.005(3) C3 0.032(3) 0.039(4) 0.042(4) -0.002(3) 0.004(3) -0.004(3) C4 0.035(4) 0.048(5) 0.068(6) -0.004(4) 0.005(4) -0.009(4) C5 0.024(3) 0.061(6) 0.072(6) 0.003(5) 0.013(4) 0.000(4) C6 0.027(3) 0.048(5) 0.053(5) 0.004(4) 0.015(3) 0.008(3) C7 0.025(3) 0.034(4) 0.030(3) 0.005(3) 0.010(3) 0.002(3) C8 0.029(3) 0.035(4) 0.031(3) -0.007(3) 0.004(3) -0.002(3) C9 0.045(4) 0.050(5) 0.032(4) -0.010(3) -0.002(3) 0.004(4) C10 0.037(4) 0.027(4) 0.050(4) -0.002(3) 0.017(3) 0.005(3) C11 0.093(7) 0.045(5) 0.057(6) -0.012(4) 0.041(5) 0.006(5) C1A 0.025(3) 0.022(3) 0.017(3) 0.006(2) 0.005(2) 0.008(2) C2A 0.037(3) 0.022(3) 0.025(3) 0.004(2) 0.005(3) 0.002(3) C3A 0.065(5) 0.022(3) 0.043(4) 0.009(3) 0.014(4) 0.008(3) C4A 0.063(5) 0.046(5) 0.037(4) 0.015(3) 0.019(4) 0.033(4) C5A 0.032(4) 0.063(5) 0.031(4) 0.014(4) 0.008(3) 0.025(4) C6A 0.025(3) 0.034(4) 0.027(3) 0.004(3) 0.005(3) 0.004(3) C1B 0.014(2) 0.025(3) 0.021(3) -0.001(2) 0.002(2) -0.004(2) C2B 0.027(3) 0.024(3) 0.028(3) 0.001(2) 0.004(3) -0.003(3) C3B 0.024(3) 0.042(4) 0.018(3) 0.001(3) -0.004(2) -0.003(3) C4B 0.033(3) 0.036(4) 0.026(3) -0.008(3) 0.000(3) -0.012(3) C5B 0.041(4) 0.024(3) 0.035(4) -0.003(3) 0.004(3) 0.003(3) C6B 0.028(3) 0.025(3) 0.027(3) 0.004(2) 0.002(3) -0.002(3) C1C 0.019(3) 0.019(3) 0.024(3) 0.005(2) 0.004(2) 0.003(2) C2C 0.027(3) 0.027(3) 0.024(3) -0.004(2) 0.005(3) -0.003(3) C3C 0.033(3) 0.036(4) 0.031(3) 0.002(3) 0.021(3) -0.001(3) C4C 0.023(3) 0.043(4) 0.039(4) 0.001(3) 0.010(3) -0.008(3) C5C 0.020(3) 0.044(4) 0.040(4) -0.004(3) 0.000(3) -0.004(3) C6C 0.024(3) 0.036(4) 0.024(3) 0.003(3) 0.002(2) -0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd1 C1 1.993(5) . ? Pd1 P1 2.2812(14) . ? Pd1 I1 2.6294(6) . ? Pd1 I2 2.6490(6) . ? P1 C1B 1.819(6) . ? P1 C1C 1.830(6) . ? P1 C1A 1.831(6) . ? N1 C1 1.329(7) . ? N1 N2 1.393(7) . ? N1 C8 1.470(8) . ? N2 C7 1.338(8) . ? N2 C10 1.475(8) . ? C1 C2 1.420(8) . ? C2 C3 1.397(9) . ? C2 C7 1.411(9) . ? C3 C4 1.367(10) . ? C4 C5 1.400(11) . ? C5 C6 1.353(11) . ? C6 C7 1.398(9) . ? C8 C9 1.514(9) . ? C10 C11 1.492(11) . ? C1A C6A 1.391(8) . ? C1A C2A 1.392(8) . ? C2A C3A 1.384(9) . ? C3A C4A 1.365(11) . ? C4A C5A 1.380(11) . ? C5A C6A 1.374(9) . ? C1B C2B 1.393(8) . ? C1B C6B 1.396(8) . ? C2B C3B 1.384(8) . ? C3B C4B 1.386(9) . ? C4B C5B 1.361(9) . ? C5B C6B 1.379(9) . ? C1C C6C 1.386(8) . ? C1C C2C 1.402(8) . ? C2C C3C 1.383(8) . ? C3C C4C 1.375(9) . ? C4C C5C 1.383(10) . ? C5C C6C 1.389(9) . ? 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 P1 89.82(16) . . ? C1 Pd1 I1 85.87(16) . . ? P1 Pd1 I1 174.89(4) . . ? C1 Pd1 I2 178.00(16) . . ? P1 Pd1 I2 91.99(4) . . ? I1 Pd1 I2 92.368(19) . . ? C1B P1 C1C 105.7(3) . . ? C1B P1 C1A 104.1(3) . . ? C1C P1 C1A 104.7(3) . . ? C1B P1 Pd1 113.60(19) . . ? C1C P1 Pd1 114.43(18) . . ? C1A P1 Pd1 113.29(18) . . ? C1 N1 N2 111.4(5) . . ? C1 N1 C8 127.8(5) . . ? N2 N1 C8 120.6(5) . . ? C7 N2 N1 107.1(5) . . ? C7 N2 C10 126.0(5) . . ? N1 N2 C10 124.9(5) . . ? N1 C1 C2 106.1(5) . . ? N1 C1 Pd1 124.1(4) . . ? C2 C1 Pd1 129.7(4) . . ? C3 C2 C7 119.7(6) . . ? C3 C2 C1 133.4(6) . . ? C7 C2 C1 106.8(6) . . ? C4 C3 C2 118.6(7) . . ? C3 C4 C5 120.7(8) . . ? C6 C5 C4 122.4(7) . . ? C5 C6 C7 117.6(7) . . ? N2 C7 C6 130.4(6) . . ? N2 C7 C2 108.6(5) . . ? C6 C7 C2 120.9(6) . . ? N1 C8 C9 113.0(6) . . ? N2 C10 C11 113.3(6) . . ? C6A C1A C2A 118.4(5) . . ? C6A C1A P1 121.2(5) . . ? C2A C1A P1 119.9(5) . . ? C3A C2A C1A 120.8(6) . . ? C4A C3A C2A 119.4(7) . . ? C3A C4A C5A 121.0(7) . . ? C6A C5A C4A 119.7(7) . . ? C5A C6A C1A 120.7(7) . . ? C2B C1B C6B 118.7(5) . . ? C2B C1B P1 120.6(4) . . ? C6B C1B P1 120.6(4) . . ? C3B C2B C1B 120.3(6) . . ? C2B C3B C4B 119.8(6) . . ? C5B C4B C3B 120.4(6) . . ? C4B C5B C6B 120.5(6) . . ? C5B C6B C1B 120.3(6) . . ? C6C C1C C2C 119.1(5) . . ? C6C C1C P1 118.2(4) . . ? C2C C1C P1 122.7(4) . . ? C3C C2C C1C 119.9(6) . . ? C4C C3C C2C 120.5(6) . . ? C3C C4C C5C 120.2(6) . . ? C4C C5C C6C 119.8(6) . . ? C1C C6C C5C 120.4(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.391 _refine_diff_density_min -1.437 _refine_diff_density_rms 0.166 # Attachment '4a.cif' data_8631 _database_code_depnum_ccdc_archive 'CCDC 757867' #TrackingRef '4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H25 F6 N2 O4 P Pd' _chemical_formula_weight 740.90 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' P P 0.1023 0.0942 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4768(5) _cell_length_b 11.0752(6) _cell_length_c 15.6695(9) _cell_angle_alpha 107.8900(10) _cell_angle_beta 100.5030(10) _cell_angle_gamma 96.7700(10) _cell_volume 1512.08(14) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5987 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 27.50 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method ? _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.743 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6809 _exptl_absorpt_correction_T_max 0.8656 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18022 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6920 _reflns_number_gt 6613 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+1.0562P] 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 6920 _refine_ls_number_parameters 418 _refine_ls_number_restraints 42 _refine_ls_R_factor_all 0.0302 _refine_ls_R_factor_gt 0.0287 _refine_ls_wR_factor_ref 0.0744 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.134 _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 0.196606(16) 0.464857(14) 0.181680(10) 0.02061(6) Uani 1 1 d . . . P1 P 0.11448(6) 0.49343(5) 0.31068(4) 0.02279(11) Uani 1 1 d . . . O1 O 0.25768(18) 0.43800(16) 0.05612(11) 0.0305(3) Uani 1 1 d . . . O2 O 0.3793(2) 0.27935(19) 0.06631(13) 0.0398(4) Uani 1 1 d . . . O3 O 0.36961(17) 0.62074(15) 0.25057(11) 0.0295(3) Uani 1 1 d . . . O4 O 0.2768(2) 0.75194(17) 0.17967(12) 0.0376(4) Uani 1 1 d . . . N1 N -0.0818(2) 0.28971(18) 0.07451(12) 0.0264(4) Uani 1 1 d . . . N2 N -0.1593(2) 0.16638(19) 0.05022(13) 0.0310(4) Uani 1 1 d . . . F1 F 0.4649(10) 0.4031(14) -0.0750(8) 0.0561(8) Uani 0.160(6) 1 d PD A 1 F2 F 0.3647(19) 0.2109(7) -0.1010(12) 0.1179(15) Uani 0.160(6) 1 d PDU A 1 F3 F 0.2360(11) 0.3432(15) -0.1290(9) 0.0644(8) Uani 0.160(6) 1 d PD A 1 F1A F 0.4011(3) 0.4434(2) -0.08166(15) 0.0561(8) Uani 0.840(6) 1 d PD A 2 F2A F 0.4325(5) 0.2514(4) -0.0973(2) 0.1179(15) Uani 0.840(6) 1 d PDU A 2 F3A F 0.2200(2) 0.2927(3) -0.13080(16) 0.0644(8) Uani 0.840(6) 1 d PD A 2 F4 F 0.62356(18) 0.79064(19) 0.30600(14) 0.0591(5) Uani 1 1 d . . . F5 F 0.4742(2) 0.88216(19) 0.37928(12) 0.0635(5) Uani 1 1 d . . . F6 F 0.5184(2) 0.92876(17) 0.26240(14) 0.0620(5) Uani 1 1 d . . . C1 C 0.0522(2) 0.3042(2) 0.12582(14) 0.0234(4) Uani 1 1 d . . . C2 C -0.0708(2) 0.0990(2) 0.08764(15) 0.0286(4) Uani 1 1 d . . . C3 C -0.0980(3) -0.0297(2) 0.08533(18) 0.0385(6) Uani 1 1 d . . . H18 H -0.1881 -0.0850 0.0541 0.046 Uiso 1 1 calc R . . C4 C 0.0143(3) -0.0699(2) 0.1312(2) 0.0425(6) Uani 1 1 d . . . H4 H 0.0000 -0.1554 0.1310 0.051 Uiso 1 1 calc R . . C5 C 0.1500(3) 0.0112(3) 0.17867(19) 0.0394(6) Uani 1 1 d . . . H5 H 0.2233 -0.0208 0.2096 0.047 Uiso 1 1 calc R . . C6 C 0.1763(3) 0.1361(2) 0.18015(16) 0.0305(5) Uani 1 1 d . . . H6 H 0.2674 0.1901 0.2110 0.037 Uiso 1 1 calc R . . C7 C 0.0639(2) 0.1817(2) 0.13445(14) 0.0248(4) Uani 1 1 d . . . C8 C -0.1477(3) 0.3862(3) 0.04359(17) 0.0385(6) Uani 1 1 d . . . H24A H -0.0810 0.4686 0.0700 0.058 Uiso 1 1 calc R . . H24B H -0.2383 0.3946 0.0634 0.058 Uiso 1 1 calc R . . H24C H -0.1675 0.3594 -0.0231 0.058 Uiso 1 1 calc R . . C9 C -0.3118(3) 0.1273(3) -0.00019(18) 0.0419(6) Uani 1 1 d . . . H29A H -0.3431 0.0356 -0.0132 0.063 Uiso 1 1 calc R . . H29B H -0.3219 0.1451 -0.0577 0.063 Uiso 1 1 calc R . . H29C H -0.3717 0.1752 0.0367 0.063 Uiso 1 1 calc R . . C10 C 0.3291(2) 0.3504(2) 0.02870(15) 0.0273(4) Uani 1 1 d . A . C11 C 0.3480(2) 0.3331(2) -0.07023(17) 0.0380(5) Uani 1 1 d D . . C12 C 0.3671(2) 0.7246(2) 0.23315(15) 0.0274(4) Uani 1 1 d . . . C13 C 0.4977(3) 0.8322(3) 0.29491(18) 0.0386(6) Uani 1 1 d . . . C1A C -0.0761(2) 0.4213(2) 0.29346(15) 0.0288(5) Uani 1 1 d . . . C2A C -0.1866(3) 0.4891(3) 0.27532(17) 0.0366(5) Uani 1 1 d . . . H2A H -0.1621 0.5764 0.2811 0.044 Uiso 1 1 calc R . . C3A C -0.3320(3) 0.4290(3) 0.2489(2) 0.0480(7) Uani 1 1 d . . . H3A H -0.4055 0.4756 0.2369 0.058 Uiso 1 1 calc R . . C4A C -0.3688(3) 0.3015(4) 0.24024(19) 0.0516(8) Uani 1 1 d . . . H4A H -0.4674 0.2604 0.2210 0.062 Uiso 1 1 calc R . . C5A C -0.2611(3) 0.2332(3) 0.25980(18) 0.0445(6) Uani 1 1 d . . . H5A H -0.2871 0.1465 0.2552 0.053 Uiso 1 1 calc R . . C6A C -0.1146(3) 0.2924(3) 0.28620(16) 0.0351(5) Uani 1 1 d . . . H6A H -0.0418 0.2456 0.2991 0.042 Uiso 1 1 calc R . . C1B C 0.2199(2) 0.4239(2) 0.38583(14) 0.0265(4) Uani 1 1 d . . . C2B C 0.1673(3) 0.3876(3) 0.45348(17) 0.0370(5) Uani 1 1 d . . . H2B H 0.0755 0.4032 0.4640 0.044 Uiso 1 1 calc R . . C3B C 0.2504(4) 0.3284(3) 0.50539(19) 0.0488(7) Uani 1 1 d . . . H3B H 0.2142 0.3028 0.5504 0.059 Uiso 1 1 calc R . . C4B C 0.3859(4) 0.3072(3) 0.4910(2) 0.0556(8) Uani 1 1 d . . . H4B H 0.4420 0.2671 0.5262 0.067 Uiso 1 1 calc R . . C5B C 0.4395(3) 0.3444(3) 0.4253(2) 0.0502(7) Uani 1 1 d . . . H5B H 0.5320 0.3297 0.4158 0.060 Uiso 1 1 calc R . . C6B C 0.3576(3) 0.4035(3) 0.37315(16) 0.0347(5) Uani 1 1 d . . . H6B H 0.3953 0.4299 0.3289 0.042 Uiso 1 1 calc R . . C1C C 0.1297(2) 0.6635(2) 0.37515(15) 0.0282(4) Uani 1 1 d . . . C2C C 0.1810(3) 0.7132(3) 0.47027(17) 0.0367(5) Uani 1 1 d . . . H2C H 0.2080 0.6582 0.5032 0.044 Uiso 1 1 calc R . . C3C C 0.1923(4) 0.8443(3) 0.5168(2) 0.0508(7) Uani 1 1 d . . . H3C H 0.2280 0.8779 0.5811 0.061 Uiso 1 1 calc R . . C4C C 0.1515(4) 0.9248(3) 0.4691(2) 0.0545(8) Uani 1 1 d . . . H4C H 0.1594 1.0133 0.5009 0.065 Uiso 1 1 calc R . . C5C C 0.0992(4) 0.8764(3) 0.3749(2) 0.0514(7) Uani 1 1 d . . . H5C H 0.0702 0.9316 0.3427 0.062 Uiso 1 1 calc R . . C6C C 0.0894(3) 0.7465(3) 0.32774(18) 0.0392(6) Uani 1 1 d . . . H6C H 0.0555 0.7141 0.2633 0.047 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 0.02276(9) 0.02060(9) 0.02058(9) 0.00925(6) 0.00558(6) 0.00489(6) P1 0.0226(2) 0.0266(3) 0.0210(2) 0.0096(2) 0.00545(19) 0.0063(2) O1 0.0381(9) 0.0324(9) 0.0291(8) 0.0153(7) 0.0154(7) 0.0120(7) O2 0.0428(10) 0.0455(11) 0.0402(10) 0.0218(8) 0.0123(8) 0.0184(8) O3 0.0283(8) 0.0276(8) 0.0325(8) 0.0132(7) 0.0035(6) 0.0025(6) O4 0.0458(10) 0.0326(9) 0.0334(9) 0.0141(7) 0.0007(7) 0.0093(8) N1 0.0299(9) 0.0255(9) 0.0236(8) 0.0096(7) 0.0030(7) 0.0051(7) N2 0.0283(9) 0.0290(10) 0.0303(10) 0.0086(8) -0.0007(8) 0.0003(8) F1 0.0567(17) 0.0686(16) 0.0425(10) 0.0254(10) 0.0144(11) -0.0134(12) F2 0.181(4) 0.177(3) 0.0762(16) 0.076(2) 0.094(2) 0.150(3) F3 0.0660(13) 0.078(2) 0.0307(9) 0.0160(13) -0.0008(9) -0.0328(12) F1A 0.0567(17) 0.0686(16) 0.0425(10) 0.0254(10) 0.0144(11) -0.0134(12) F2A 0.181(4) 0.177(3) 0.0762(16) 0.076(2) 0.094(2) 0.150(3) F3A 0.0660(13) 0.078(2) 0.0307(9) 0.0160(13) -0.0008(9) -0.0328(12) F4 0.0350(9) 0.0599(11) 0.0714(12) 0.0210(10) -0.0047(8) -0.0044(8) F5 0.0764(13) 0.0563(11) 0.0350(9) -0.0053(8) 0.0076(8) -0.0102(10) F6 0.0764(13) 0.0357(9) 0.0678(12) 0.0253(9) 0.0037(10) -0.0140(9) C1 0.0257(10) 0.0251(10) 0.0210(9) 0.0091(8) 0.0060(8) 0.0058(8) C2 0.0307(11) 0.0267(11) 0.0269(10) 0.0083(9) 0.0057(8) 0.0025(9) C3 0.0435(14) 0.0263(12) 0.0416(13) 0.0099(10) 0.0087(11) -0.0033(10) C4 0.0570(16) 0.0240(12) 0.0501(15) 0.0167(11) 0.0146(13) 0.0054(11) C5 0.0469(14) 0.0347(13) 0.0438(14) 0.0207(11) 0.0100(11) 0.0157(11) C6 0.0312(11) 0.0294(12) 0.0321(11) 0.0127(9) 0.0052(9) 0.0077(9) C7 0.0279(10) 0.0228(10) 0.0237(10) 0.0079(8) 0.0063(8) 0.0033(8) C8 0.0445(14) 0.0383(14) 0.0331(12) 0.0164(11) -0.0017(10) 0.0140(11) C9 0.0297(12) 0.0488(16) 0.0376(13) 0.0098(12) -0.0029(10) 0.0004(11) C10 0.0242(10) 0.0312(11) 0.0247(10) 0.0089(9) 0.0052(8) 0.0007(9) C11 0.0421(13) 0.0435(14) 0.0319(12) 0.0127(11) 0.0151(10) 0.0113(11) C12 0.0314(11) 0.0250(11) 0.0242(10) 0.0072(8) 0.0064(8) 0.0022(9) C13 0.0444(14) 0.0323(13) 0.0341(12) 0.0112(10) 0.0036(10) -0.0034(11) C1A 0.0246(10) 0.0416(13) 0.0226(10) 0.0122(9) 0.0086(8) 0.0063(9) C2A 0.0299(12) 0.0515(15) 0.0330(12) 0.0179(11) 0.0092(9) 0.0119(11) C3A 0.0288(12) 0.081(2) 0.0436(15) 0.0299(15) 0.0108(11) 0.0173(13) C4A 0.0255(12) 0.089(2) 0.0367(14) 0.0224(15) 0.0055(10) -0.0046(13) C5A 0.0393(14) 0.0540(17) 0.0364(13) 0.0151(12) 0.0100(11) -0.0079(12) C6A 0.0317(12) 0.0439(14) 0.0306(11) 0.0143(10) 0.0097(9) 0.0010(10) C1B 0.0297(11) 0.0282(11) 0.0220(10) 0.0096(8) 0.0034(8) 0.0075(9) C2B 0.0435(14) 0.0433(14) 0.0303(12) 0.0177(11) 0.0114(10) 0.0126(11) C3B 0.0687(19) 0.0546(17) 0.0330(13) 0.0269(13) 0.0111(13) 0.0168(15) C4B 0.070(2) 0.063(2) 0.0404(15) 0.0278(15) 0.0002(14) 0.0296(17) C5B 0.0424(15) 0.069(2) 0.0435(15) 0.0235(14) 0.0025(12) 0.0269(14) C6B 0.0314(12) 0.0457(14) 0.0293(11) 0.0158(10) 0.0042(9) 0.0117(10) C1C 0.0277(10) 0.0296(11) 0.0286(11) 0.0088(9) 0.0095(8) 0.0080(9) C2C 0.0399(13) 0.0362(13) 0.0299(12) 0.0074(10) 0.0050(10) 0.0062(10) C3C 0.0647(19) 0.0414(16) 0.0355(14) 0.0008(12) 0.0084(13) 0.0066(14) C4C 0.072(2) 0.0325(14) 0.0568(18) 0.0049(13) 0.0252(16) 0.0137(14) C5C 0.072(2) 0.0393(15) 0.0554(17) 0.0222(13) 0.0261(15) 0.0252(15) C6C 0.0508(15) 0.0378(14) 0.0355(13) 0.0154(11) 0.0152(11) 0.0164(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 Pd1 C1 1.959(2) . ? Pd1 O3 2.0919(16) . ? Pd1 O1 2.0953(15) . ? Pd1 P1 2.2429(5) . ? P1 C1B 1.813(2) . ? P1 C1C 1.818(2) . ? P1 C1A 1.822(2) . ? O1 C10 1.260(3) . ? O2 C10 1.210(3) . ? O3 C12 1.263(3) . ? O4 C12 1.217(3) . ? N1 C1 1.336(3) . ? N1 N2 1.376(3) . ? N1 C8 1.460(3) . ? N2 C2 1.357(3) . ? N2 C9 1.458(3) . ? F1 C11 1.303(4) . ? F2 C11 1.330(4) . ? F3 C11 1.312(4) . ? F1A C11 1.342(3) . ? F2A C11 1.303(3) . ? F3A C11 1.328(3) . ? F4 C13 1.330(3) . ? F5 C13 1.338(3) . ? F6 C13 1.328(3) . ? C1 C7 1.418(3) . ? C2 C7 1.406(3) . ? C2 C3 1.406(3) . ? C3 C4 1.370(4) . ? C4 C5 1.408(4) . ? C5 C6 1.370(3) . ? C6 C7 1.405(3) . ? C10 C11 1.549(3) . ? C12 C13 1.548(3) . ? C1A C6A 1.396(4) . ? C1A C2A 1.396(3) . ? C2A C3A 1.386(4) . ? C3A C4A 1.373(5) . ? C4A C5A 1.385(5) . ? C5A C6A 1.392(3) . ? C1B C6B 1.389(3) . ? C1B C2B 1.393(3) . ? C2B C3B 1.389(4) . ? C3B C4B 1.379(5) . ? C4B C5B 1.374(5) . ? C5B C6B 1.384(3) . ? C1C C2C 1.389(3) . ? C1C C6C 1.393(3) . ? C2C C3C 1.392(4) . ? C3C C4C 1.375(5) . ? C4C C5C 1.377(4) . ? C5C C6C 1.384(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Pd1 O3 171.49(7) . . ? C1 Pd1 O1 90.29(7) . . ? O3 Pd1 O1 91.73(6) . . ? C1 Pd1 P1 87.52(6) . . ? O3 Pd1 P1 90.96(5) . . ? O1 Pd1 P1 175.78(5) . . ? C1B P1 C1C 107.35(10) . . ? C1B P1 C1A 106.08(11) . . ? C1C P1 C1A 105.38(11) . . ? C1B P1 Pd1 110.35(7) . . ? C1C P1 Pd1 111.83(7) . . ? C1A P1 Pd1 115.36(7) . . ? C10 O1 Pd1 118.95(14) . . ? C12 O3 Pd1 119.07(14) . . ? C1 N1 N2 111.96(18) . . ? C1 N1 C8 127.8(2) . . ? N2 N1 C8 120.23(19) . . ? C2 N2 N1 107.00(18) . . ? C2 N2 C9 129.7(2) . . ? N1 N2 C9 123.1(2) . . ? N1 C1 C7 105.73(18) . . ? N1 C1 Pd1 126.27(16) . . ? C7 C1 Pd1 127.94(16) . . ? N2 C2 C7 108.1(2) . . ? N2 C2 C3 130.0(2) . . ? C7 C2 C3 121.9(2) . . ? C4 C3 C2 116.2(2) . . ? C3 C4 C5 123.0(2) . . ? C6 C5 C4 120.6(2) . . ? C5 C6 C7 118.4(2) . . ? C6 C7 C2 120.0(2) . . ? C6 C7 C1 132.8(2) . . ? C2 C7 C1 107.16(19) . . ? O2 C10 O1 130.2(2) . . ? O2 C10 C11 117.9(2) . . ? O1 C10 C11 111.87(19) . . ? F1 C11 F2A 75.0(7) . . ? F1 C11 F3 108.5(4) . . ? F2A C11 F3 120.7(9) . . ? F1 C11 F3A 127.7(6) . . ? F2A C11 F3A 107.8(2) . . ? F3 C11 F3A 24.2(6) . . ? F1 C11 F2 106.5(4) . . ? F2A C11 F2 31.8(7) . . ? F3 C11 F2 106.0(4) . . ? F3A C11 F2 85.3(7) . . ? F1 C11 F1A 35.3(6) . . ? F2A C11 F1A 107.1(2) . . ? F3 C11 F1A 79.7(6) . . ? F3A C11 F1A 103.2(2) . . ? F2 C11 F1A 135.6(7) . . ? F1 C11 C10 115.1(6) . . ? F2A C11 C10 113.2(2) . . ? F3 C11 C10 116.9(7) . . ? F3A C11 C10 111.1(2) . . ? F2 C11 C10 102.8(8) . . ? F1A C11 C10 113.8(2) . . ? O4 C12 O3 130.1(2) . . ? O4 C12 C13 117.7(2) . . ? O3 C12 C13 112.1(2) . . ? F6 C13 F4 106.8(2) . . ? F6 C13 F5 107.2(2) . . ? F4 C13 F5 106.4(2) . . ? F6 C13 C12 112.6(2) . . ? F4 C13 C12 113.5(2) . . ? F5 C13 C12 109.9(2) . . ? C6A C1A C2A 118.8(2) . . ? C6A C1A P1 120.48(18) . . ? C2A C1A P1 120.15(19) . . ? C3A C2A C1A 120.8(3) . . ? C4A C3A C2A 120.0(3) . . ? C3A C4A C5A 120.2(3) . . ? C4A C5A C6A 120.4(3) . . ? C5A C6A C1A 119.8(3) . . ? C6B C1B C2B 119.1(2) . . ? C6B C1B P1 117.94(17) . . ? C2B C1B P1 122.89(18) . . ? C3B C2B C1B 120.0(2) . . ? C4B C3B C2B 120.0(3) . . ? C5B C4B C3B 120.3(3) . . ? C4B C5B C6B 120.1(3) . . ? C5B C6B C1B 120.3(2) . . ? C2C C1C C6C 119.1(2) . . ? C2C C1C P1 121.85(19) . . ? C6C C1C P1 119.04(18) . . ? C1C C2C C3C 120.0(3) . . ? C4C C3C C2C 120.2(3) . . ? C3C C4C C5C 120.3(3) . . ? C4C C5C C6C 120.0(3) . . ? C5C C6C C1C 120.4(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.792 _refine_diff_density_min -0.723 _refine_diff_density_rms 0.077 # Attachment '5.cif' data_9070 _database_code_depnum_ccdc_archive 'CCDC 757868' #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H28 Br4 N4 Pd2' _chemical_formula_weight 880.92 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' Br Br -0.2901 2.4595 '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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5153(16) _cell_length_b 11.2069(18) _cell_length_c 12.916(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.929(4) _cell_angle_gamma 90.00 _cell_volume 1369.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 1992 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 27.33 _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.136 _exptl_crystal_density_method ? _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 7.164 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2224 _exptl_absorpt_correction_T_max 0.3936 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9280 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3145 _reflns_number_gt 1981 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1135P)^2^+0.9176P] 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 3145 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1019 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1968 _refine_ls_wR_factor_gt 0.1771 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 1.05217(7) 0.97610(6) 0.37345(5) 0.0514(3) Uani 1 1 d . . . Br1 Br 1.17520(11) 1.00616(8) 0.55496(7) 0.0628(3) Uani 1 1 d . . . Br2 Br 1.27218(11) 0.95014(13) 0.30150(8) 0.0860(4) Uani 1 1 d . . . N1 N 0.8772(7) 0.8743(6) 0.1950(5) 0.0580(18) Uani 1 1 d . . . N2 N 0.8167(7) 0.8976(6) 0.0949(5) 0.0589(18) Uani 1 1 d . . . C1 C 0.9544(8) 0.9655(6) 0.2345(6) 0.0496(19) Uani 1 1 d . . . C2 C 0.9374(8) 1.0582(7) 0.1584(6) 0.0451(17) Uani 1 1 d . . . C3 C 0.9893(8) 1.1740(7) 0.1537(6) 0.0521(19) Uani 1 1 d . . . H3 H 1.0516 1.2045 0.2086 0.063 Uiso 1 1 calc R . . C4 C 0.9486(9) 1.2427(8) 0.0684(7) 0.065(2) Uani 1 1 d . . . H4 H 0.9814 1.3216 0.0648 0.078 Uiso 1 1 calc R . . C5 C 0.8581(9) 1.1954(8) -0.0134(7) 0.061(2) Uani 1 1 d . . . H5 H 0.8311 1.2445 -0.0710 0.073 Uiso 1 1 calc R . . C6 C 0.8071(8) 1.0824(9) -0.0139(6) 0.059(2) Uani 1 1 d . . . H6 H 0.7468 1.0527 -0.0702 0.071 Uiso 1 1 calc R . . C7 C 0.8490(8) 1.0116(7) 0.0739(6) 0.0431(17) Uani 1 1 d . . . C8 C 0.7165(9) 0.8177(7) 0.0362(7) 0.061(2) Uani 1 1 d . . . H8A H 0.7468 0.7352 0.0500 0.074 Uiso 1 1 calc R . . H8B H 0.7197 0.8327 -0.0383 0.074 Uiso 1 1 calc R . . C9 C 0.5682(10) 0.8306(10) 0.0609(9) 0.088(3) Uani 1 1 d . . . H9A H 0.5621 0.8081 0.1328 0.132 Uiso 1 1 calc R . . H9B H 0.5073 0.7793 0.0155 0.132 Uiso 1 1 calc R . . H9C H 0.5385 0.9129 0.0506 0.132 Uiso 1 1 calc R . . C10 C 0.8535(10) 0.7551(8) 0.2489(8) 0.068(2) Uani 1 1 d . . . H10A H 0.8497 0.7685 0.3236 0.081 Uiso 1 1 calc R . . H10B H 0.7630 0.7208 0.2203 0.081 Uiso 1 1 calc R . . C11 C 0.9661(11) 0.6730(9) 0.2337(9) 0.088(3) Uani 1 1 d . . . H11A H 0.9651 0.6552 0.1602 0.132 Uiso 1 1 calc R . . H11B H 0.9529 0.5999 0.2717 0.132 Uiso 1 1 calc R . . H11C H 1.0560 0.7087 0.2590 0.132 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 0.0665(5) 0.0341(4) 0.0481(4) 0.0023(2) -0.0204(3) -0.0025(3) Br1 0.0708(6) 0.0539(5) 0.0579(6) -0.0026(4) -0.0214(4) -0.0043(4) Br2 0.0707(7) 0.1158(10) 0.0675(7) 0.0022(6) -0.0123(5) 0.0116(6) N1 0.080(5) 0.034(3) 0.053(4) 0.006(3) -0.024(3) 0.001(3) N2 0.067(4) 0.049(4) 0.054(4) -0.005(3) -0.025(3) -0.005(3) C1 0.061(5) 0.033(4) 0.052(5) -0.002(3) -0.008(4) 0.005(3) C2 0.045(4) 0.040(4) 0.048(4) 0.003(3) -0.008(3) 0.012(3) C3 0.053(5) 0.048(5) 0.056(5) 0.000(4) 0.011(4) 0.007(4) C4 0.068(6) 0.037(4) 0.090(7) 0.018(4) 0.004(5) 0.001(4) C5 0.059(5) 0.061(6) 0.060(6) 0.021(4) -0.001(4) 0.009(4) C6 0.049(5) 0.079(7) 0.047(5) 0.008(4) -0.005(4) 0.007(4) C7 0.040(4) 0.045(4) 0.044(4) 0.000(3) 0.001(3) 0.007(3) C8 0.072(6) 0.044(5) 0.063(5) -0.007(4) -0.023(4) -0.001(4) C9 0.067(6) 0.065(7) 0.126(9) 0.011(6) -0.017(6) 0.002(5) C10 0.078(6) 0.055(5) 0.068(6) -0.005(4) -0.005(5) -0.019(5) C11 0.084(7) 0.060(6) 0.116(9) 0.017(6) -0.008(6) 0.005(5) _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 1.938(8) . ? Pd1 Br2 2.3943(13) . ? Pd1 Br1 2.4471(13) 3_776 ? Pd1 Br1 2.5323(11) . ? Br1 Pd1 2.4471(13) 3_776 ? N1 C1 1.329(9) . ? N1 N2 1.385(8) . ? N1 C10 1.535(11) . ? N2 C7 1.349(10) . ? N2 C8 1.461(9) . ? C1 C2 1.428(10) . ? C2 C3 1.391(11) . ? C2 C7 1.407(10) . ? C3 C4 1.368(11) . ? C4 C5 1.396(12) . ? C5 C6 1.356(13) . ? C6 C7 1.407(11) . ? C8 C9 1.486(13) . ? C10 C11 1.441(13) . ? 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 Br2 89.3(2) . . ? C1 Pd1 Br1 89.8(2) . 3_776 ? Br2 Pd1 Br1 177.57(5) . 3_776 ? C1 Pd1 Br1 175.8(2) . . ? Br2 Pd1 Br1 92.08(4) . . ? Br1 Pd1 Br1 88.94(4) 3_776 . ? Pd1 Br1 Pd1 91.06(4) 3_776 . ? C1 N1 N2 111.9(6) . . ? C1 N1 C10 126.7(7) . . ? N2 N1 C10 121.4(6) . . ? C7 N2 N1 106.5(6) . . ? C7 N2 C8 128.8(7) . . ? N1 N2 C8 123.7(7) . . ? N1 C1 C2 106.1(7) . . ? N1 C1 Pd1 126.6(6) . . ? C2 C1 Pd1 127.0(6) . . ? C3 C2 C7 119.9(7) . . ? C3 C2 C1 133.8(8) . . ? C7 C2 C1 106.2(7) . . ? C4 C3 C2 119.2(8) . . ? C3 C4 C5 119.8(8) . . ? C6 C5 C4 123.4(8) . . ? C5 C6 C7 116.8(8) . . ? N2 C7 C6 130.1(8) . . ? N2 C7 C2 109.0(7) . . ? C6 C7 C2 120.8(8) . . ? N2 C8 C9 114.3(8) . . ? C11 C10 N1 110.3(8) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.959 _refine_diff_density_min -0.993 _refine_diff_density_rms 0.246 # Attachment '6.cif' data_9256 _database_code_depnum_ccdc_archive 'CCDC 757869' #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 Au Cl N2' _chemical_formula_weight 406.66 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.5290(6) _cell_length_b 8.5217(6) _cell_length_c 17.3001(11) _cell_angle_alpha 90.00 _cell_angle_beta 103.8820(10) _cell_angle_gamma 90.00 _cell_volume 1220.67(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5662 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.48 _exptl_crystal_description BLOCK _exptl_crystal_colour 'PALE YELLOW' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 2.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 12.240 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.1204 _exptl_absorpt_correction_T_max 0.3213 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8394 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2788 _reflns_number_gt 2651 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0220P)^2^+0.9483P] 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 2788 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0206 _refine_ls_R_factor_gt 0.0191 _refine_ls_wR_factor_ref 0.0467 _refine_ls_wR_factor_gt 0.0461 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.275840(13) 0.466169(13) 0.822607(6) 0.01479(5) Uani 1 1 d . . . Cl1 Cl 0.10499(10) 0.53130(9) 0.90161(5) 0.02021(16) Uani 1 1 d . . . N1 N 0.5821(3) 0.4131(3) 0.77462(15) 0.0161(5) Uani 1 1 d . . . N2 N 0.6512(3) 0.3650(3) 0.71405(15) 0.0166(5) Uani 1 1 d . . . C1 C 0.4201(4) 0.4120(4) 0.75258(18) 0.0166(6) Uani 1 1 d . . . C2 C 0.3820(4) 0.3674(3) 0.67068(18) 0.0157(6) Uani 1 1 d . . . C3 C 0.2347(4) 0.3459(4) 0.61435(19) 0.0185(6) Uani 1 1 d . . . H3 H 0.1347 0.3623 0.6281 0.022 Uiso 1 1 calc R . . C4 C 0.2395(4) 0.3003(4) 0.53849(18) 0.0205(7) Uani 1 1 d . . . H4 H 0.1414 0.2834 0.4997 0.025 Uiso 1 1 calc R . . C5 C 0.3879(4) 0.2783(4) 0.51777(19) 0.0217(7) Uani 1 1 d . . . H5 H 0.3867 0.2483 0.4647 0.026 Uiso 1 1 calc R . . C6 C 0.5336(4) 0.2983(4) 0.57092(18) 0.0196(6) Uani 1 1 d . . . H6 H 0.6329 0.2834 0.5561 0.023 Uiso 1 1 calc R . . C7 C 0.5285(4) 0.3423(4) 0.64865(18) 0.0166(6) Uani 1 1 d . . . C8 C 0.6828(4) 0.4312(4) 0.85595(19) 0.0183(6) Uani 1 1 d . . . H8A H 0.6215 0.4898 0.8885 0.022 Uiso 1 1 calc R . . H8B H 0.7802 0.4931 0.8543 0.022 Uiso 1 1 calc R . . C9 C 0.7335(4) 0.2740(4) 0.89442(19) 0.0229(7) Uani 1 1 d . . . H9A H 0.6373 0.2126 0.8961 0.034 Uiso 1 1 calc R . . H9B H 0.7987 0.2903 0.9487 0.034 Uiso 1 1 calc R . . H9C H 0.7974 0.2173 0.8633 0.034 Uiso 1 1 calc R . . C10 C 0.8215(4) 0.3910(4) 0.71549(18) 0.0167(6) Uani 1 1 d . . . H10A H 0.8545 0.3158 0.6787 0.020 Uiso 1 1 calc R . . H10B H 0.8876 0.3696 0.7698 0.020 Uiso 1 1 calc R . . C11 C 0.8556(5) 0.5566(4) 0.6918(2) 0.0250(7) Uani 1 1 d . . . H11A H 0.7885 0.5795 0.6385 0.037 Uiso 1 1 calc R . . H11B H 0.9699 0.5659 0.6913 0.037 Uiso 1 1 calc R . . H11C H 0.8304 0.6313 0.7301 0.037 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 Au1 0.01410(7) 0.01619(8) 0.01439(8) -0.00143(4) 0.00401(5) -0.00044(4) Cl1 0.0175(4) 0.0276(4) 0.0173(4) -0.0023(3) 0.0076(3) -0.0004(3) N1 0.0170(12) 0.0181(13) 0.0141(12) -0.0035(10) 0.0053(10) 0.0007(10) N2 0.0177(12) 0.0196(13) 0.0133(12) -0.0042(10) 0.0053(10) 0.0012(10) C1 0.0165(14) 0.0161(15) 0.0161(14) -0.0006(12) 0.0017(11) 0.0007(12) C2 0.0185(14) 0.0120(14) 0.0168(14) -0.0002(11) 0.0048(12) -0.0004(11) C3 0.0157(14) 0.0187(15) 0.0209(15) -0.0002(12) 0.0041(12) 0.0014(11) C4 0.0210(15) 0.0206(16) 0.0163(15) 0.0013(12) -0.0025(12) 0.0018(12) C5 0.0280(17) 0.0243(17) 0.0129(14) -0.0012(12) 0.0049(12) 0.0007(13) C6 0.0226(15) 0.0209(16) 0.0162(15) -0.0007(12) 0.0068(12) 0.0014(12) C7 0.0174(14) 0.0148(14) 0.0167(14) -0.0001(11) 0.0022(12) -0.0008(11) C8 0.0141(14) 0.0244(16) 0.0155(15) -0.0071(12) 0.0018(12) -0.0017(12) C9 0.0257(17) 0.0279(18) 0.0135(15) 0.0003(13) 0.0020(12) -0.0007(14) C10 0.0166(14) 0.0177(15) 0.0159(14) 0.0000(12) 0.0041(11) 0.0017(12) C11 0.0274(18) 0.0227(17) 0.0249(18) 0.0061(13) 0.0064(15) -0.0003(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 Au1 C1 1.977(3) . ? Au1 Cl1 2.2925(8) . ? N1 C1 1.343(4) . ? N1 N2 1.382(3) . ? N1 C8 1.470(4) . ? N2 C7 1.358(4) . ? N2 C10 1.464(4) . ? C1 C2 1.427(4) . ? C2 C3 1.405(4) . ? C2 C7 1.407(4) . ? C3 C4 1.379(4) . ? C4 C5 1.408(5) . ? C5 C6 1.368(5) . ? C6 C7 1.407(4) . ? C8 C9 1.512(5) . ? C10 C11 1.517(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 C1 Au1 Cl1 178.82(9) . . ? C1 N1 N2 112.3(2) . . ? C1 N1 C8 126.7(3) . . ? N2 N1 C8 120.0(2) . . ? C7 N2 N1 106.9(2) . . ? C7 N2 C10 126.8(2) . . ? N1 N2 C10 123.0(2) . . ? N1 C1 C2 104.9(3) . . ? N1 C1 Au1 125.0(2) . . ? C2 C1 Au1 130.1(2) . . ? C3 C2 C7 119.8(3) . . ? C3 C2 C1 132.5(3) . . ? C7 C2 C1 107.7(3) . . ? C4 C3 C2 118.1(3) . . ? C3 C4 C5 120.9(3) . . ? C6 C5 C4 122.6(3) . . ? C5 C6 C7 116.4(3) . . ? N2 C7 C6 129.8(3) . . ? N2 C7 C2 108.0(3) . . ? C6 C7 C2 122.2(3) . . ? N1 C8 C9 111.6(3) . . ? N2 C10 C11 113.0(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.301 _refine_diff_density_min -0.791 _refine_diff_density_rms 0.128 # Attachment '7.cif' data_9183 _database_code_depnum_ccdc_archive 'CCDC 757870' #TrackingRef '7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H22 Cl N2 Rh' _chemical_formula_weight 392.73 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Rh Rh -1.1178 0.9187 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0142(4) _cell_length_b 9.5187(6) _cell_length_c 12.8813(8) _cell_angle_alpha 75.2460(10) _cell_angle_beta 82.9050(10) _cell_angle_gamma 74.5310(10) _cell_volume 800.12(8) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3115 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 27.41 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 1.229 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7094 _exptl_absorpt_correction_T_max 0.9299 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5717 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3643 _reflns_number_gt 3411 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+0.4041P] 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 3643 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0358 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0842 _refine_ls_wR_factor_gt 0.0829 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 Rh1 Rh 0.58818(3) 0.27765(2) 0.205335(16) 0.02450(9) Uani 1 1 d . . . Cl1 Cl 0.25115(10) 0.39530(8) 0.25439(6) 0.03192(16) Uani 1 1 d . . . N1 N 0.7051(3) 0.4650(3) 0.32911(19) 0.0263(5) Uani 1 1 d . . . N2 N 0.7442(4) 0.4757(3) 0.42935(19) 0.0300(5) Uani 1 1 d . . . C1 C 0.6754(4) 0.3314(3) 0.3296(2) 0.0261(6) Uani 1 1 d . . . C2 C 0.7021(4) 0.2487(3) 0.4388(2) 0.0262(6) Uani 1 1 d . . . C3 C 0.6933(5) 0.1010(3) 0.4907(3) 0.0330(6) Uani 1 1 d . . . H3 H 0.6688 0.0366 0.4522 0.040 Uiso 1 1 calc R . . C4 C 0.7212(5) 0.0532(4) 0.5990(3) 0.0381(7) Uani 1 1 d . . . H4 H 0.7201 -0.0460 0.6345 0.046 Uiso 1 1 calc R . . C5 C 0.7515(4) 0.1512(4) 0.6573(2) 0.0352(7) Uani 1 1 d . . . H5 H 0.7667 0.1159 0.7317 0.042 Uiso 1 1 calc R . . C6 C 0.7597(4) 0.2966(4) 0.6098(2) 0.0320(6) Uani 1 1 d . . . H6 H 0.7780 0.3614 0.6498 0.038 Uiso 1 1 calc R . . C7 C 0.7392(4) 0.3429(3) 0.4982(2) 0.0268(6) Uani 1 1 d . . . C8 C 0.7135(5) 0.5873(3) 0.2357(2) 0.0357(7) Uani 1 1 d . . . H8A H 0.6771 0.5634 0.1732 0.054 Uiso 1 1 calc R . . H8B H 0.8470 0.6016 0.2233 0.054 Uiso 1 1 calc R . . H8C H 0.6220 0.6785 0.2484 0.054 Uiso 1 1 calc R . . C9 C 0.7670(5) 0.6131(3) 0.4497(3) 0.0330(6) Uani 1 1 d . . . H9A H 0.7852 0.5982 0.5255 0.050 Uiso 1 1 calc R . . H9B H 0.6494 0.6927 0.4297 0.050 Uiso 1 1 calc R . . H9C H 0.8817 0.6403 0.4076 0.050 Uiso 1 1 calc R . . C10 C 0.4802(4) 0.1504(3) 0.1153(2) 0.0307(6) Uani 1 1 d . . . H10 H 0.3367 0.1555 0.1279 0.037 Uiso 1 1 calc R . . C11 C 0.5252(5) 0.2724(3) 0.0423(2) 0.0327(6) Uani 1 1 d . . . H11 H 0.4079 0.3502 0.0125 0.039 Uiso 1 1 calc R . . C12 C 0.7101(5) 0.2647(4) -0.0332(3) 0.0400(7) Uani 1 1 d . . . H12A H 0.6779 0.3371 -0.1017 0.048 Uiso 1 1 calc R . . H12B H 0.7540 0.1644 -0.0478 0.048 Uiso 1 1 calc R . . C13 C 0.8798(5) 0.2982(4) 0.0138(3) 0.0397(7) Uani 1 1 d . . . H13A H 1.0063 0.2470 -0.0167 0.048 Uiso 1 1 calc R . . H13B H 0.8703 0.4062 -0.0084 0.048 Uiso 1 1 calc R . . C14 C 0.8794(4) 0.2504(4) 0.1347(3) 0.0346(7) Uani 1 1 d . . . H14 H 0.9651 0.2940 0.1664 0.042 Uiso 1 1 calc R . . C15 C 0.8511(4) 0.1123(3) 0.1979(3) 0.0329(6) Uani 1 1 d . . . H15 H 0.9216 0.0766 0.2653 0.039 Uiso 1 1 calc R . . C16 C 0.8285(5) -0.0132(3) 0.1504(3) 0.0374(7) Uani 1 1 d . . . H16A H 0.8886 -0.1099 0.1970 0.045 Uiso 1 1 calc R . . H16B H 0.9004 -0.0067 0.0798 0.045 Uiso 1 1 calc R . . C17 C 0.6111(5) -0.0062(4) 0.1379(3) 0.0381(7) Uani 1 1 d . . . H17A H 0.6051 -0.0527 0.0790 0.046 Uiso 1 1 calc R . . H17B H 0.5593 -0.0651 0.2040 0.046 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 Rh1 0.02681(13) 0.02395(13) 0.02353(13) -0.00693(8) -0.00352(8) -0.00529(8) Cl1 0.0293(3) 0.0349(4) 0.0337(4) -0.0149(3) -0.0035(3) -0.0040(3) N1 0.0289(12) 0.0250(11) 0.0260(12) -0.0059(9) -0.0034(9) -0.0076(9) N2 0.0394(14) 0.0272(12) 0.0271(12) -0.0082(10) -0.0046(10) -0.0116(10) C1 0.0246(13) 0.0255(13) 0.0287(14) -0.0071(11) -0.0036(10) -0.0052(10) C2 0.0237(13) 0.0287(14) 0.0267(14) -0.0071(11) -0.0017(10) -0.0068(11) C3 0.0349(16) 0.0302(15) 0.0345(16) -0.0053(12) -0.0017(12) -0.0109(12) C4 0.0413(18) 0.0319(15) 0.0357(17) 0.0014(13) -0.0027(13) -0.0085(13) C5 0.0307(15) 0.0452(18) 0.0258(15) -0.0010(13) -0.0040(11) -0.0086(13) C6 0.0288(14) 0.0418(17) 0.0277(15) -0.0100(12) -0.0018(11) -0.0108(12) C7 0.0229(13) 0.0310(14) 0.0288(14) -0.0097(11) -0.0002(10) -0.0084(11) C8 0.0483(19) 0.0273(14) 0.0303(16) -0.0030(12) -0.0022(13) -0.0108(13) C9 0.0327(15) 0.0323(15) 0.0404(17) -0.0142(13) -0.0024(12) -0.0131(12) C10 0.0321(15) 0.0347(15) 0.0307(15) -0.0150(12) -0.0036(11) -0.0093(12) C11 0.0375(16) 0.0357(16) 0.0262(15) -0.0103(12) -0.0099(12) -0.0047(13) C12 0.054(2) 0.0404(17) 0.0259(15) -0.0060(13) -0.0003(14) -0.0142(15) C13 0.0426(18) 0.0366(17) 0.0387(18) -0.0104(14) 0.0086(14) -0.0112(14) C14 0.0295(15) 0.0402(17) 0.0376(17) -0.0159(14) 0.0026(12) -0.0098(13) C15 0.0295(15) 0.0321(15) 0.0363(16) -0.0122(13) -0.0061(12) -0.0006(12) C16 0.0418(18) 0.0286(15) 0.0405(18) -0.0113(13) -0.0045(13) -0.0022(13) C17 0.0444(18) 0.0297(15) 0.0434(18) -0.0132(13) -0.0021(14) -0.0103(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 Rh1 C1 2.006(3) . ? Rh1 C15 2.091(3) . ? Rh1 C14 2.108(3) . ? Rh1 C10 2.193(3) . ? Rh1 C11 2.215(3) . ? Rh1 Cl1 2.4127(7) . ? N1 C1 1.341(4) . ? N1 N2 1.386(3) . ? N1 C8 1.453(4) . ? N2 C7 1.353(4) . ? N2 C9 1.450(4) . ? C1 C2 1.433(4) . ? C2 C7 1.408(4) . ? C2 C3 1.409(4) . ? C3 C4 1.374(4) . ? C4 C5 1.407(5) . ? C5 C6 1.377(4) . ? C6 C7 1.405(4) . ? C10 C11 1.378(4) . ? C10 C17 1.504(4) . ? C11 C12 1.519(4) . ? C12 C13 1.538(5) . ? C13 C14 1.508(5) . ? C14 C15 1.409(4) . ? C15 C16 1.524(4) . ? C16 C17 1.535(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 C1 Rh1 C15 91.79(11) . . ? C1 Rh1 C14 89.88(12) . . ? C15 Rh1 C14 39.21(12) . . ? C1 Rh1 C10 159.61(12) . . ? C15 Rh1 C10 82.70(11) . . ? C14 Rh1 C10 97.90(12) . . ? C1 Rh1 C11 163.83(12) . . ? C15 Rh1 C11 90.06(12) . . ? C14 Rh1 C11 81.45(12) . . ? C10 Rh1 C11 36.42(11) . . ? C1 Rh1 Cl1 88.61(8) . . ? C15 Rh1 Cl1 160.24(9) . . ? C14 Rh1 Cl1 160.54(9) . . ? C10 Rh1 Cl1 90.09(8) . . ? C11 Rh1 Cl1 95.02(8) . . ? C1 N1 N2 113.1(2) . . ? C1 N1 C8 126.6(2) . . ? N2 N1 C8 120.2(2) . . ? C7 N2 N1 106.9(2) . . ? C7 N2 C9 130.1(3) . . ? N1 N2 C9 122.7(2) . . ? N1 C1 C2 103.8(2) . . ? N1 C1 Rh1 125.5(2) . . ? C2 C1 Rh1 130.5(2) . . ? C7 C2 C3 119.7(3) . . ? C7 C2 C1 108.5(2) . . ? C3 C2 C1 131.8(3) . . ? C4 C3 C2 118.5(3) . . ? C3 C4 C5 120.7(3) . . ? C6 C5 C4 122.6(3) . . ? C5 C6 C7 116.4(3) . . ? N2 C7 C6 130.3(3) . . ? N2 C7 C2 107.6(2) . . ? C6 C7 C2 122.0(3) . . ? C11 C10 C17 125.7(3) . . ? C11 C10 Rh1 72.64(17) . . ? C17 C10 Rh1 107.1(2) . . ? C10 C11 C12 124.2(3) . . ? C10 C11 Rh1 70.94(17) . . ? C12 C11 Rh1 111.5(2) . . ? C11 C12 C13 112.2(3) . . ? C14 C13 C12 113.8(3) . . ? C15 C14 C13 125.6(3) . . ? C15 C14 Rh1 69.73(17) . . ? C13 C14 Rh1 111.3(2) . . ? C14 C15 C16 123.3(3) . . ? C14 C15 Rh1 71.06(17) . . ? C16 C15 Rh1 113.3(2) . . ? C15 C16 C17 112.6(3) . . ? C10 C17 C16 113.7(3) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.025 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.097