# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_Compound_8a _database_code_depnum_ccdc_archive 'CCDC 915849' #TrackingRef '16211_web_deposit_cif_file_0_ThomasStrassner_1355568752.8a.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_formula_moiety 'C14 H14 Br2 N4 Pd' _chemical_formula_sum 'C14 H14 Br2 N4 Pd' _chemical_formula_weight 504.49 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' Br Br -0.2901 2.4595 ' 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' Pd Pd -0.9988 1.0072 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,1/2+y,1/2+z 4 1/2+x,1/2-y,z _cell_length_a 12.4150(9) _cell_length_b 9.508(2) _cell_length_c 14.0530(17) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1658.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 198 _cell_measurement_reflns_used 161 _cell_measurement_theta_min 4.180 _cell_measurement_theta_max 25.372 _exptl_crystal_description fragment _exptl_crystal_colour yellow _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 2.020 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 5.934 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 2002' _exptl_absorpt_correction_T_min 0.383 _exptl_absorpt_correction_T_max 0.383 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 198 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method \f _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_wavelength_id x-ray # number of measured reflections (redundant set) _diffrn_reflns_number 11505 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.82 _diffrn_reflns_theta_max 25.39 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3005 # number of observed reflections (> n sig(I)) _reflns_number_gt 2748 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius BV, 1999)' _computing_cell_refinement 'Dirax/lsq (Duisenberg, 1992)' _computing_data_reduction 'EvalCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SIR92(Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2011)' _computing_publication_material 'PLATON (Spek, 2011), enCIFer (Allen, 2004)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs 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^)+(0.0000P)^2^] 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_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.025(7) _chemical_absolute_configuration unk _refine_ls_number_reflns 3005 _refine_ls_number_parameters 192 _refine_ls_number_restraints 1 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0270 _refine_ls_R_factor_gt 0.0205 _refine_ls_wR_factor_ref 0.0375 _refine_ls_wR_factor_gt 0.0360 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.331 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.078 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd Uani 0.84999(2) 1.00853(2) 0.68725(3) 1.000 0.0145(1) d . . . Br1 Br Uani 0.98490(2) 0.81390(3) 0.68860(4) 1.000 0.0248(1) d . . . Br2 Br Uani 0.88055(3) 1.06732(4) 0.51682(3) 1.000 0.0265(1) d . . . N1 N Uani 0.7810(2) 0.8794(3) 0.8717(2) 1.000 0.0175(9) d . . . N2 N Uani 0.8485(2) 1.0852(3) 0.8920(2) 1.000 0.0173(9) d . . . N3 N Uani 0.7597(2) 1.2779(3) 0.7534(2) 1.000 0.0170(9) d . . . N4 N Uani 0.6489(2) 1.1783(3) 0.65746(19) 1.000 0.0196(9) d . . . C1 C Uani 0.8238(3) 0.9877(3) 0.8244(3) 1.000 0.0167(11) d . . . C2 C Uani 0.7803(3) 0.9049(4) 0.9688(2) 1.000 0.0200(11) d . . . C3 C Uani 0.8243(3) 1.0330(4) 0.9826(2) 1.000 0.0194(11) d . . . C4 C Uani 0.8973(3) 1.2179(3) 0.8735(2) 1.000 0.0150(10) d . . . C5 C Uani 0.9875(3) 1.2573(4) 0.9255(3) 1.000 0.0212(11) d . . . C6 C Uani 1.0352(3) 1.3860(4) 0.9102(3) 1.000 0.0261(11) d . . . C7 C Uani 0.9942(3) 1.4766(4) 0.8426(3) 1.000 0.0276(11) d . . . C8 C Uani 0.9045(3) 1.4379(4) 0.7902(3) 1.000 0.0209(11) d . . . C9 C Uani 0.8550(3) 1.3095(4) 0.8059(2) 1.000 0.0174(10) d . . . C10 C Uani 0.7454(2) 1.1617(3) 0.6985(3) 1.000 0.0176(10) d . . . C11 C Uani 0.6024(2) 1.3050(4) 0.6840(4) 1.000 0.0248(10) d . . . C12 C Uani 0.6710(3) 1.3686(4) 0.7446(3) 1.000 0.0247(12) d . . . C13 C Uani 0.7406(3) 0.7514(4) 0.8269(3) 1.000 0.0243(12) d . . . C14 C Uani 0.5986(3) 1.0784(4) 0.5917(3) 1.000 0.0293(14) d . . . H2 H Uiso 0.75380 0.84360 1.01670 1.000 0.0240 c R . . H3 H Uiso 0.83630 1.07850 1.04180 1.000 0.0230 c R . . H5 H Uiso 1.01650 1.19510 0.97190 1.000 0.0250 c R . . H6 H Uiso 1.09670 1.41250 0.94630 1.000 0.0310 c R . . H7 H Uiso 1.02740 1.56520 0.83200 1.000 0.0330 c R . . H8 H Uiso 0.87670 1.49990 0.74320 1.000 0.0250 c R . . H11 H Uiso 0.53480 1.34030 0.66330 1.000 0.0300 c R . . H12 H Uiso 0.66130 1.45690 0.77510 1.000 0.0290 c R . . H13A H Uiso 0.77520 0.66930 0.85590 1.000 0.0370 c R . . H13B H Uiso 0.75700 0.75360 0.75870 1.000 0.0370 c R . . H13C H Uiso 0.66250 0.74530 0.83590 1.000 0.0370 c R . . H14A H Uiso 0.65450 1.03160 0.55400 1.000 0.0440 c R . . H14B H Uiso 0.54940 1.12880 0.54910 1.000 0.0440 c R . . H14C H Uiso 0.55810 1.00790 0.62790 1.000 0.0440 c R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pd1 0.0173(1) 0.0133(1) 0.0129(1) 0.0012(1) -0.0002(2) 0.0019(1) Br1 0.0293(2) 0.0211(2) 0.0241(2) 0.0050(2) 0.0023(2) 0.0101(1) Br2 0.0315(2) 0.0321(2) 0.0158(2) 0.0052(2) 0.0019(2) 0.0118(2) N1 0.0198(15) 0.0152(15) 0.0174(16) 0.0031(12) -0.0024(13) -0.0036(12) N2 0.0181(15) 0.0169(17) 0.0169(17) 0.0025(13) -0.0024(12) -0.0011(13) N3 0.0181(15) 0.0162(14) 0.0168(16) 0.0025(12) -0.0023(12) 0.0028(13) N4 0.0170(14) 0.0260(17) 0.0158(18) 0.0010(11) -0.0013(11) -0.0021(13) C1 0.0154(17) 0.0116(18) 0.023(2) 0.0018(15) -0.0009(15) 0.0000(15) C2 0.027(2) 0.022(2) 0.0111(18) 0.0071(14) 0.0027(15) -0.0027(17) C3 0.027(2) 0.022(2) 0.0091(18) 0.0053(14) -0.0004(14) -0.0019(16) C4 0.0177(17) 0.0140(18) 0.0133(18) -0.0028(13) 0.0001(14) 0.0000(14) C5 0.0237(18) 0.020(2) 0.020(2) -0.0004(16) -0.0040(15) 0.0019(16) C6 0.0242(19) 0.027(2) 0.027(2) -0.0074(18) -0.0025(17) -0.0046(17) C7 0.032(2) 0.0177(19) 0.033(2) -0.0001(16) 0.0044(19) -0.0098(17) C8 0.028(2) 0.0146(17) 0.020(2) 0.0035(14) 0.0036(16) 0.0025(17) C9 0.0194(18) 0.0168(18) 0.0159(18) -0.0021(14) 0.0022(15) 0.0033(15) C10 0.0178(15) 0.0170(15) 0.018(2) 0.0034(17) 0.0054(18) 0.0018(13) C11 0.0188(14) 0.0274(17) 0.0281(19) 0.004(2) 0.006(2) 0.0105(14) C12 0.024(2) 0.021(2) 0.029(2) 0.0000(16) 0.0060(17) 0.0078(17) C13 0.031(2) 0.019(2) 0.023(2) -0.0024(15) 0.0027(17) -0.0071(18) C14 0.025(2) 0.034(3) 0.029(2) -0.0053(18) -0.0073(17) -0.0039(18) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd1 Br1 2.4960(6) . . yes Pd1 Br2 2.4885(8) . . yes Pd1 C1 1.965(4) . . yes Pd1 C10 1.958(3) . . yes N1 C1 1.336(4) . . yes N1 C2 1.386(4) . . yes N1 C13 1.459(5) . . yes N2 C1 1.362(5) . . yes N2 C3 1.399(4) . . yes N2 C4 1.424(4) . . yes N3 C9 1.426(4) . . yes N3 C10 1.359(4) . . yes N3 C12 1.404(5) . . yes N4 C10 1.339(4) . . yes N4 C11 1.387(5) . . yes N4 C14 1.465(5) . . yes C2 C3 1.349(5) . . no C4 C5 1.389(5) . . no C4 C9 1.392(5) . . no C5 C6 1.376(5) . . no C6 C7 1.380(6) . . no C7 C8 1.385(5) . . no C8 C9 1.385(5) . . no C11 C12 1.348(6) . . no C2 H2 0.9500 . . no C3 H3 0.9500 . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no C7 H7 0.9500 . . no C8 H8 0.9500 . . no C11 H11 0.9500 . . no C12 H12 0.9500 . . no C13 H13A 0.9800 . . no C13 H13B 0.9800 . . no C13 H13C 0.9800 . . no C14 H14A 0.9800 . . no C14 H14B 0.9800 . . no C14 H14C 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Br1 Pd1 Br2 94.10(2) . . . yes Br1 Pd1 C1 91.65(10) . . . yes Br1 Pd1 C10 174.91(13) . . . yes Br2 Pd1 C1 172.78(8) . . . yes Br2 Pd1 C10 90.67(12) . . . yes C1 Pd1 C10 83.45(15) . . . yes C1 N1 C2 111.0(3) . . . yes C1 N1 C13 124.4(3) . . . yes C2 N1 C13 124.7(3) . . . yes C1 N2 C3 110.2(3) . . . yes C1 N2 C4 124.9(3) . . . yes C3 N2 C4 124.9(3) . . . yes C9 N3 C10 125.0(3) . . . yes C9 N3 C12 124.5(3) . . . yes C10 N3 C12 110.3(3) . . . yes C10 N4 C11 111.0(3) . . . yes C10 N4 C14 125.2(3) . . . yes C11 N4 C14 123.7(3) . . . yes Pd1 C1 N1 129.2(3) . . . yes Pd1 C1 N2 125.3(2) . . . yes N1 C1 N2 105.5(3) . . . yes N1 C2 C3 107.3(3) . . . yes N2 C3 C2 106.1(3) . . . yes N2 C4 C5 119.1(3) . . . yes N2 C4 C9 121.3(3) . . . yes C5 C4 C9 119.7(3) . . . no C4 C5 C6 120.3(4) . . . no C5 C6 C7 120.3(4) . . . no C6 C7 C8 119.8(4) . . . no C7 C8 C9 120.4(4) . . . no N3 C9 C4 122.3(3) . . . yes N3 C9 C8 118.1(3) . . . yes C4 C9 C8 119.6(3) . . . no Pd1 C10 N3 124.3(2) . . . yes Pd1 C10 N4 130.3(3) . . . yes N3 C10 N4 105.4(2) . . . yes N4 C11 C12 107.3(3) . . . yes N3 C12 C11 106.0(3) . . . yes N1 C2 H2 126.00 . . . no C3 C2 H2 126.00 . . . no N2 C3 H3 127.00 . . . no C2 C3 H3 127.00 . . . no C4 C5 H5 120.00 . . . no C6 C5 H5 120.00 . . . no C5 C6 H6 120.00 . . . no C7 C6 H6 120.00 . . . no C6 C7 H7 120.00 . . . no C8 C7 H7 120.00 . . . no C7 C8 H8 120.00 . . . no C9 C8 H8 120.00 . . . no N4 C11 H11 126.00 . . . no C12 C11 H11 126.00 . . . no N3 C12 H12 127.00 . . . no C11 C12 H12 127.00 . . . no N1 C13 H13A 110.00 . . . no N1 C13 H13B 109.00 . . . no N1 C13 H13C 110.00 . . . no H13A C13 H13B 109.00 . . . no H13A C13 H13C 109.00 . . . no H13B C13 H13C 109.00 . . . no N4 C14 H14A 109.00 . . . no N4 C14 H14B 110.00 . . . no N4 C14 H14C 110.00 . . . no H14A C14 H14B 109.00 . . . no H14A C14 H14C 109.00 . . . no H14B C14 H14C 109.00 . . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br1 Pd1 C1 N1 -65.1(3) . . . . no Br1 Pd1 C1 N2 114.0(3) . . . . no C10 Pd1 C1 N1 116.3(3) . . . . no C10 Pd1 C1 N2 -64.6(3) . . . . no Br2 Pd1 C10 N3 -114.1(3) . . . . no Br2 Pd1 C10 N4 65.8(3) . . . . no C1 Pd1 C10 N3 61.7(3) . . . . no C1 Pd1 C10 N4 -118.4(3) . . . . no C2 N1 C1 Pd1 177.8(3) . . . . no C2 N1 C1 N2 -1.4(4) . . . . no C13 N1 C1 Pd1 -2.1(5) . . . . no C13 N1 C1 N2 178.7(3) . . . . no C1 N1 C2 C3 -0.2(4) . . . . no C13 N1 C2 C3 179.8(3) . . . . no C3 N2 C1 Pd1 -176.8(3) . . . . no C3 N2 C1 N1 2.4(4) . . . . no C4 N2 C1 Pd1 0.0(5) . . . . no C4 N2 C1 N1 179.3(3) . . . . no C1 N2 C3 C2 -2.6(4) . . . . no C4 N2 C3 C2 -179.4(3) . . . . no C1 N2 C4 C5 -129.3(4) . . . . no C1 N2 C4 C9 52.0(5) . . . . no C3 N2 C4 C5 47.1(5) . . . . no C3 N2 C4 C9 -131.6(3) . . . . no C10 N3 C9 C4 -56.9(5) . . . . no C10 N3 C9 C8 125.0(4) . . . . no C12 N3 C9 C4 128.9(4) . . . . no C12 N3 C9 C8 -49.2(5) . . . . no C9 N3 C10 Pd1 4.1(5) . . . . no C9 N3 C10 N4 -175.9(3) . . . . no C12 N3 C10 Pd1 179.0(3) . . . . no C12 N3 C10 N4 -1.0(4) . . . . no C9 N3 C12 C11 175.3(3) . . . . no C10 N3 C12 C11 0.4(4) . . . . no C11 N4 C10 Pd1 -178.7(3) . . . . no C11 N4 C10 N3 1.2(4) . . . . no C14 N4 C10 Pd1 0.2(5) . . . . no C14 N4 C10 N3 -179.9(3) . . . . no C10 N4 C11 C12 -1.0(5) . . . . no C14 N4 C11 C12 -179.9(3) . . . . no N1 C2 C3 N2 1.6(4) . . . . no N2 C4 C5 C6 -178.9(3) . . . . no C9 C4 C5 C6 -0.2(6) . . . . no N2 C4 C9 N3 1.6(5) . . . . no N2 C4 C9 C8 179.7(3) . . . . no C5 C4 C9 N3 -177.0(3) . . . . no C5 C4 C9 C8 1.1(5) . . . . no C4 C5 C6 C7 -0.4(6) . . . . no C5 C6 C7 C8 0.2(6) . . . . no C6 C7 C8 C9 0.7(6) . . . . no C7 C8 C9 N3 176.9(3) . . . . no C7 C8 C9 C4 -1.3(6) . . . . no N4 C11 C12 N3 0.3(5) . . . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C5 H5 Br2 0.9500 2.8700 3.723(4) 149.00 2_775 yes C14 H14A Br2 0.9800 2.8700 3.657(4) 137.00 . yes data_Compound_8b _database_code_depnum_ccdc_archive 'CCDC 915850' #TrackingRef '16212_web_deposit_cif_file_1_ThomasStrassner_1355568752.8b.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_formula_moiety 'C22 H18 Br2 N4 Pd, 2(C2 H3 N)' _chemical_formula_sum 'C26 H24 Br2 N6 Pd' _chemical_formula_weight 686.71 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' Br Br -0.2901 2.4595 ' 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' Pd Pd -0.9988 1.0072 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 9.7310(12) _cell_length_b 10.752(2) _cell_length_c 13.9470(7) _cell_angle_alpha 96.085(9) _cell_angle_beta 103.753(6) _cell_angle_gamma 98.478(15) _cell_volume 1386.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 198 _cell_measurement_reflns_used 980 _cell_measurement_theta_min 4.099 _cell_measurement_theta_max 24.829 _cell_special_details ; ; _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.330 _exptl_crystal_size_mid 0.190 _exptl_crystal_size_min 0.190 _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 3.576 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 2002' _exptl_absorpt_correction_T_min 0.386 _exptl_absorpt_correction_T_max 0.556 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 198 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method \f _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_wavelength_id x-ray # number of measured reflections (redundant set) _diffrn_reflns_number 5686 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 26.40 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 5686 # number of observed reflections (> n sig(I)) _reflns_number_gt 4437 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius BV, 1999)' _computing_cell_refinement 'Dirax/lsq (Duisenberg, 1992)' _computing_data_reduction 'EvalCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SIR92(Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2011)' _computing_publication_material 'PLATON (Spek, 2011), enCIFer (Allen, 2004)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs 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^)+(0.0203P)^2^+1.4433P] 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_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 5686 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0576 _refine_ls_wR_factor_gt 0.0536 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.496 _refine_diff_density_min -0.540 _refine_diff_density_rms 0.090 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd Uani 0.17324(2) 0.33595(2) 0.23173(2) 1.000 0.0215(1) d . . . Br1 Br Uani 0.09370(3) 0.53122(3) 0.17810(2) 1.000 0.0320(1) d . . . Br2 Br Uani -0.00639(3) 0.29625(3) 0.33103(2) 1.000 0.0357(1) d . . . N1 N Uani 0.2985(2) 0.3312(2) 0.05597(16) 1.000 0.0216(7) d . . . N2 N Uani 0.4621(2) 0.3749(2) 0.19633(16) 1.000 0.0215(7) d . . . N3 N Uani 0.3968(3) 0.1951(2) 0.32233(17) 1.000 0.0249(8) d . . . N4 N Uani 0.2012(3) 0.0641(2) 0.24196(18) 1.000 0.0292(8) d . . . C1 C Uani 0.3176(3) 0.3516(3) 0.1550(2) 1.000 0.0208(9) d . . . C2 C Uani 0.4306(3) 0.3405(3) 0.0318(2) 1.000 0.0220(9) d . . . C3 C Uani 0.5365(3) 0.3696(3) 0.1213(2) 1.000 0.0217(9) d . . . C4 C Uani 0.5273(3) 0.3993(3) 0.3010(2) 1.000 0.0220(9) d . . . C5 C Uani 0.6237(3) 0.5110(3) 0.3418(2) 1.000 0.0306(10) d . . . C6 C Uani 0.6911(3) 0.5334(3) 0.4430(2) 1.000 0.0359(11) d . . . C7 C Uani 0.6613(3) 0.4449(3) 0.5035(2) 1.000 0.0355(10) d . . . C8 C Uani 0.5645(3) 0.3343(3) 0.4637(2) 1.000 0.0310(10) d . . . C9 C Uani 0.4965(3) 0.3106(3) 0.3626(2) 1.000 0.0244(9) d . . . C10 C Uani 0.2588(3) 0.1879(3) 0.2689(2) 1.000 0.0241(9) d . . . C11 C Uani 0.3012(4) -0.0108(3) 0.2776(2) 1.000 0.0316(10) d . . . C12 C Uani 0.4270(4) 0.0725(3) 0.3301(2) 1.000 0.0296(10) d . . . C13 C Uani 0.4645(3) 0.3257(3) -0.0592(2) 1.000 0.0292(10) d . . . C14 C Uani 0.6082(3) 0.3411(3) -0.0564(2) 1.000 0.0330(11) d . . . C15 C Uani 0.7149(3) 0.3699(3) 0.0344(2) 1.000 0.0332(11) d . . . C16 C Uani 0.6808(3) 0.3841(3) 0.1246(2) 1.000 0.0275(10) d . . . C17 C Uani 0.2919(4) -0.1410(3) 0.2672(2) 1.000 0.0428(13) d . . . C18 C Uani 0.4135(5) -0.1845(3) 0.3110(3) 1.000 0.0506(14) d . . . C19 C Uani 0.5396(5) -0.1031(4) 0.3633(3) 1.000 0.0519(16) d . . . C20 C Uani 0.5499(4) 0.0282(3) 0.3743(2) 1.000 0.0405(11) d . . . C21 C Uani 0.1587(3) 0.3006(3) -0.0171(2) 1.000 0.0316(10) d . . . C22 C Uani 0.0573(4) 0.0139(3) 0.1783(3) 1.000 0.0423(11) d . . . N5 N Uani -0.1578(4) 0.7744(3) 0.2812(2) 1.000 0.0537(12) d . . . C23 C Uani 0.0314(4) 0.6776(4) 0.4003(3) 1.000 0.0579(16) d . . . C24 C Uani -0.0754(4) 0.7320(4) 0.3329(3) 1.000 0.0433(12) d . . . N6 N Uani 0.2819(4) 0.0123(4) 0.0201(3) 1.000 0.0769(17) d . . . C25 C Uani 0.3429(5) -0.0363(4) -0.1488(3) 1.000 0.0666(17) d . . . C26 C Uani 0.3085(4) -0.0099(4) -0.0533(3) 1.000 0.0538(16) d . . . H5 H Uiso 0.64380 0.57230 0.30040 1.000 0.0370 c R . . H6 H Uiso 0.75780 0.60980 0.47090 1.000 0.0430 c R . . H7 H Uiso 0.70780 0.46040 0.57290 1.000 0.0430 c R . . H8 H Uiso 0.54410 0.27390 0.50570 1.000 0.0370 c R . . H13 H Uiso 0.39210 0.30580 -0.12050 1.000 0.0350 c R . . H14 H Uiso 0.63600 0.33210 -0.11720 1.000 0.0400 c R . . H15 H Uiso 0.81320 0.37980 0.03340 1.000 0.0400 c R . . H16 H Uiso 0.75290 0.40300 0.18600 1.000 0.0330 c R . . H17 H Uiso 0.20600 -0.19730 0.23160 1.000 0.0510 c R . . H18 H Uiso 0.41150 -0.27360 0.30550 1.000 0.0610 c R . . H19 H Uiso 0.62110 -0.13810 0.39230 1.000 0.0620 c R . . H20 H Uiso 0.63610 0.08410 0.41010 1.000 0.0480 c R . . H21A H Uiso 0.14970 0.21750 -0.05670 1.000 0.0470 c R . . H21B H Uiso 0.15060 0.36570 -0.06120 1.000 0.0470 c R . . H21C H Uiso 0.08210 0.29800 0.01770 1.000 0.0470 c R . . H22A H Uiso 0.00440 0.08380 0.16590 1.000 0.0630 c R . . H22B H Uiso 0.00630 -0.04660 0.21140 1.000 0.0630 c R . . H22C H Uiso 0.06450 -0.02950 0.11470 1.000 0.0630 c R . . H23A H Uiso 0.01460 0.58520 0.38070 1.000 0.0870 c R . . H23B H Uiso 0.02330 0.69670 0.46880 1.000 0.0870 c R . . H23C H Uiso 0.12800 0.71430 0.39660 1.000 0.0870 c R . . H25A H Uiso 0.28240 -0.11580 -0.18620 1.000 0.1000 c R . . H25B H Uiso 0.44440 -0.04440 -0.13710 1.000 0.1000 c R . . H25C H Uiso 0.32520 0.03350 -0.18720 1.000 0.1000 c R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pd1 0.0192(1) 0.0231(1) 0.0195(1) 0.0022(1) 0.0027(1) -0.0004(1) Br1 0.0312(2) 0.0293(2) 0.0364(2) 0.0077(1) 0.0078(1) 0.0075(1) Br2 0.0321(2) 0.0458(2) 0.0289(2) 0.0048(2) 0.0123(1) -0.0009(2) N1 0.0189(12) 0.0228(13) 0.0186(13) 0.0014(10) -0.0007(10) -0.0001(10) N2 0.0198(12) 0.0245(14) 0.0172(12) 0.0037(10) 0.0006(10) 0.0009(10) N3 0.0312(14) 0.0195(14) 0.0222(13) 0.0057(10) 0.0038(11) 0.0025(11) N4 0.0352(15) 0.0224(14) 0.0284(14) 0.0016(11) 0.0105(12) -0.0023(12) C1 0.0223(15) 0.0166(15) 0.0198(15) 0.0014(11) 0.0004(12) 0.0012(12) C2 0.0236(15) 0.0183(15) 0.0232(15) 0.0064(12) 0.0040(12) 0.0016(12) C3 0.0247(16) 0.0172(15) 0.0229(15) 0.0045(12) 0.0063(12) 0.0012(12) C4 0.0170(14) 0.0255(16) 0.0202(15) 0.0018(12) -0.0005(11) 0.0036(12) C5 0.0268(17) 0.0309(18) 0.0290(17) 0.0030(14) 0.0032(13) -0.0034(14) C6 0.0270(17) 0.039(2) 0.0307(18) -0.0078(15) -0.0020(14) -0.0045(15) C7 0.0341(18) 0.047(2) 0.0198(16) -0.0018(15) -0.0027(14) 0.0101(16) C8 0.0345(18) 0.0361(19) 0.0225(16) 0.0078(14) 0.0032(14) 0.0106(15) C9 0.0226(15) 0.0270(17) 0.0219(15) 0.0022(13) 0.0018(12) 0.0063(13) C10 0.0278(16) 0.0232(17) 0.0206(15) 0.0022(12) 0.0075(13) 0.0012(13) C11 0.052(2) 0.0217(17) 0.0243(16) 0.0049(13) 0.0173(15) 0.0034(15) C12 0.046(2) 0.0261(18) 0.0214(16) 0.0072(13) 0.0133(14) 0.0112(15) C13 0.0353(18) 0.0263(17) 0.0228(16) -0.0002(13) 0.0059(13) 0.0012(14) C14 0.040(2) 0.0328(19) 0.0294(18) 0.0014(14) 0.0176(15) 0.0050(15) C15 0.0272(17) 0.0300(18) 0.044(2) 0.0043(15) 0.0139(15) 0.0035(14) C16 0.0232(16) 0.0270(17) 0.0295(17) 0.0039(13) 0.0028(13) 0.0022(13) C17 0.074(3) 0.0259(19) 0.0323(19) 0.0066(15) 0.0221(18) 0.0055(18) C18 0.098(3) 0.027(2) 0.034(2) 0.0074(16) 0.025(2) 0.019(2) C19 0.083(3) 0.047(3) 0.038(2) 0.0194(18) 0.019(2) 0.036(2) C20 0.054(2) 0.040(2) 0.0309(18) 0.0112(16) 0.0085(16) 0.0194(18) C21 0.0257(16) 0.038(2) 0.0240(16) 0.0006(14) -0.0031(13) 0.0017(14) C22 0.0353(19) 0.037(2) 0.044(2) -0.0017(16) 0.0045(16) -0.0124(16) N5 0.049(2) 0.058(2) 0.049(2) 0.0116(17) 0.0044(16) 0.0047(17) C23 0.059(3) 0.088(3) 0.035(2) 0.013(2) 0.0167(19) 0.029(2) C24 0.043(2) 0.054(2) 0.035(2) 0.0055(18) 0.0189(18) 0.0020(19) N6 0.087(3) 0.084(3) 0.073(3) 0.020(2) 0.036(2) 0.026(2) C25 0.062(3) 0.071(3) 0.064(3) 0.000(2) 0.019(2) 0.006(2) C26 0.050(2) 0.046(3) 0.066(3) 0.015(2) 0.011(2) 0.0117(19) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd1 Br1 2.4705(6) . . yes Pd1 Br2 2.4924(6) . . yes Pd1 C1 1.957(3) . . yes Pd1 C10 1.964(3) . . yes N1 C1 1.339(3) . . yes N1 C2 1.397(4) . . yes N1 C21 1.461(4) . . yes N2 C1 1.361(4) . . yes N2 C3 1.408(4) . . yes N2 C4 1.425(3) . . yes N3 C9 1.427(4) . . yes N3 C10 1.359(4) . . yes N3 C12 1.402(4) . . yes N4 C10 1.342(4) . . yes N4 C11 1.389(4) . . yes N4 C22 1.458(5) . . yes N5 C24 1.128(5) . . yes N6 C26 1.124(6) . . yes C2 C13 1.384(4) . . no C2 C3 1.389(4) . . no C3 C16 1.379(4) . . no C4 C9 1.396(4) . . no C4 C5 1.384(4) . . no C5 C6 1.386(4) . . no C6 C7 1.381(4) . . no C7 C8 1.375(4) . . no C8 C9 1.386(4) . . no C11 C12 1.396(5) . . no C11 C17 1.379(5) . . no C12 C20 1.385(5) . . no C13 C14 1.374(4) . . no C14 C15 1.405(4) . . no C15 C16 1.374(4) . . no C17 C18 1.368(6) . . no C18 C19 1.388(6) . . no C19 C20 1.390(5) . . no C5 H5 0.9500 . . no C6 H6 0.9500 . . no C7 H7 0.9500 . . no C8 H8 0.9500 . . no C13 H13 0.9500 . . no C14 H14 0.9500 . . no C15 H15 0.9500 . . no C16 H16 0.9500 . . no C17 H17 0.9500 . . no C18 H18 0.9500 . . no C19 H19 0.9500 . . no C20 H20 0.9500 . . no C21 H21C 0.9800 . . no C21 H21A 0.9800 . . no C21 H21B 0.9800 . . no C22 H22C 0.9800 . . no C22 H22A 0.9800 . . no C22 H22B 0.9800 . . no C23 C24 1.462(6) . . no C23 H23B 0.9800 . . no C23 H23C 0.9800 . . no C23 H23A 0.9800 . . no C25 C26 1.458(6) . . no C25 H25A 0.9800 . . no C25 H25B 0.9800 . . no C25 H25C 0.9800 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Br1 Pd1 Br2 94.52(2) . . . yes Br1 Pd1 C1 90.53(9) . . . yes Br1 Pd1 C10 172.66(9) . . . yes Br2 Pd1 C1 174.83(10) . . . yes Br2 Pd1 C10 92.54(9) . . . yes C1 Pd1 C10 82.45(13) . . . yes C1 N1 C2 110.8(2) . . . yes C1 N1 C21 124.8(2) . . . yes C2 N1 C21 124.4(2) . . . yes C1 N2 C3 110.4(2) . . . yes C1 N2 C4 124.3(2) . . . yes C3 N2 C4 125.4(2) . . . yes C9 N3 C10 124.8(2) . . . yes C9 N3 C12 125.3(3) . . . yes C10 N3 C12 109.9(3) . . . yes C10 N4 C11 110.6(3) . . . yes C10 N4 C22 125.2(3) . . . yes C11 N4 C22 124.1(2) . . . yes Pd1 C1 N1 128.9(2) . . . yes Pd1 C1 N2 124.20(19) . . . yes N1 C1 N2 106.7(2) . . . yes N1 C2 C3 106.8(2) . . . yes N1 C2 C13 131.6(3) . . . yes C3 C2 C13 121.7(3) . . . no N2 C3 C2 105.4(2) . . . yes N2 C3 C16 132.6(2) . . . yes C2 C3 C16 122.0(3) . . . no N2 C4 C5 119.8(3) . . . yes N2 C4 C9 120.6(3) . . . yes C5 C4 C9 119.6(3) . . . no C4 C5 C6 120.1(3) . . . no C5 C6 C7 120.1(3) . . . no C6 C7 C8 120.2(3) . . . no C7 C8 C9 120.3(3) . . . no N3 C9 C4 120.7(2) . . . yes N3 C9 C8 119.6(3) . . . yes C4 C9 C8 119.7(3) . . . no Pd1 C10 N3 124.1(2) . . . yes Pd1 C10 N4 128.6(2) . . . yes N3 C10 N4 107.2(3) . . . yes N4 C11 C12 106.6(3) . . . yes N4 C11 C17 131.3(3) . . . yes C12 C11 C17 122.2(3) . . . no N3 C12 C11 105.8(3) . . . yes N3 C12 C20 132.7(3) . . . yes C11 C12 C20 121.4(3) . . . no C2 C13 C14 116.6(3) . . . no C13 C14 C15 121.5(3) . . . no C14 C15 C16 121.7(3) . . . no C3 C16 C15 116.5(3) . . . no C11 C17 C18 116.2(3) . . . no C17 C18 C19 122.4(3) . . . no C18 C19 C20 121.8(4) . . . no C12 C20 C19 116.0(3) . . . no C4 C5 H5 120.00 . . . no C6 C5 H5 120.00 . . . no C5 C6 H6 120.00 . . . no C7 C6 H6 120.00 . . . no C6 C7 H7 120.00 . . . no C8 C7 H7 120.00 . . . no C7 C8 H8 120.00 . . . no C9 C8 H8 120.00 . . . no C2 C13 H13 122.00 . . . no C14 C13 H13 122.00 . . . no C13 C14 H14 119.00 . . . no C15 C14 H14 119.00 . . . no C14 C15 H15 119.00 . . . no C16 C15 H15 119.00 . . . no C3 C16 H16 122.00 . . . no C15 C16 H16 122.00 . . . no C11 C17 H17 122.00 . . . no C18 C17 H17 122.00 . . . no C17 C18 H18 119.00 . . . no C19 C18 H18 119.00 . . . no C18 C19 H19 119.00 . . . no C20 C19 H19 119.00 . . . no C12 C20 H20 122.00 . . . no C19 C20 H20 122.00 . . . no N1 C21 H21A 109.00 . . . no N1 C21 H21B 109.00 . . . no N1 C21 H21C 109.00 . . . no H21A C21 H21B 110.00 . . . no H21A C21 H21C 109.00 . . . no H21B C21 H21C 110.00 . . . no N4 C22 H22A 110.00 . . . no N4 C22 H22B 109.00 . . . no N4 C22 H22C 109.00 . . . no H22A C22 H22B 109.00 . . . no H22A C22 H22C 109.00 . . . no H22B C22 H22C 109.00 . . . no N5 C24 C23 179.7(4) . . . yes C24 C23 H23A 109.00 . . . no C24 C23 H23B 109.00 . . . no C24 C23 H23C 110.00 . . . no H23A C23 H23B 109.00 . . . no H23A C23 H23C 109.00 . . . no H23B C23 H23C 109.00 . . . no N6 C26 C25 179.0(5) . . . yes C26 C25 H25A 109.00 . . . no C26 C25 H25B 109.00 . . . no C26 C25 H25C 109.00 . . . no H25A C25 H25B 109.00 . . . no H25A C25 H25C 110.00 . . . no H25B C25 H25C 109.00 . . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br1 Pd1 C1 N1 -72.6(3) . . . . no Br1 Pd1 C1 N2 114.1(3) . . . . no C10 Pd1 C1 N1 109.6(3) . . . . no C10 Pd1 C1 N2 -63.8(3) . . . . no Br2 Pd1 C10 N3 -117.0(2) . . . . no Br2 Pd1 C10 N4 68.7(3) . . . . no C1 Pd1 C10 N3 64.3(2) . . . . no C1 Pd1 C10 N4 -110.0(3) . . . . no C2 N1 C1 Pd1 -174.0(2) . . . . no C21 N1 C1 Pd1 4.8(4) . . . . no C2 N1 C1 N2 0.3(3) . . . . no C21 N1 C1 N2 179.0(2) . . . . no C21 N1 C2 C13 0.4(5) . . . . no C1 N1 C2 C3 -0.7(3) . . . . no C21 N1 C2 C3 -179.4(3) . . . . no C1 N1 C2 C13 179.2(3) . . . . no C4 N2 C1 Pd1 -4.4(4) . . . . no C3 N2 C1 N1 0.3(3) . . . . no C4 N2 C1 N1 -178.9(2) . . . . no C3 N2 C1 Pd1 174.8(2) . . . . no C3 N2 C4 C9 -120.8(3) . . . . no C1 N2 C3 C16 -178.8(3) . . . . no C4 N2 C3 C16 0.4(5) . . . . no C1 N2 C3 C2 -0.6(3) . . . . no C4 N2 C3 C2 178.5(3) . . . . no C1 N2 C4 C5 -122.7(3) . . . . no C3 N2 C4 C5 58.2(4) . . . . no C1 N2 C4 C9 58.3(4) . . . . no C12 N3 C10 N4 -0.5(3) . . . . no C9 N3 C10 N4 178.3(3) . . . . no C10 N3 C12 C11 0.8(3) . . . . no C12 N3 C10 Pd1 -175.9(2) . . . . no C9 N3 C12 C20 -0.2(5) . . . . no C12 N3 C9 C8 -56.4(4) . . . . no C9 N3 C12 C11 -178.0(3) . . . . no C9 N3 C10 Pd1 3.0(4) . . . . no C10 N3 C9 C8 125.0(3) . . . . no C10 N3 C9 C4 -55.7(4) . . . . no C10 N3 C12 C20 178.7(3) . . . . no C12 N3 C9 C4 123.0(3) . . . . no C10 N4 C11 C12 0.5(3) . . . . no C22 N4 C11 C17 -2.6(5) . . . . no C10 N4 C11 C17 -178.7(3) . . . . no C22 N4 C10 N3 -176.0(3) . . . . no C22 N4 C10 Pd1 -0.9(5) . . . . no C11 N4 C10 Pd1 175.1(2) . . . . no C11 N4 C10 N3 0.0(3) . . . . no C22 N4 C11 C12 176.5(3) . . . . no N1 C2 C3 C16 179.2(3) . . . . no C13 C2 C3 N2 -179.1(3) . . . . no N1 C2 C3 N2 0.8(3) . . . . no C13 C2 C3 C16 -0.7(5) . . . . no N1 C2 C13 C14 -179.7(3) . . . . no C3 C2 C13 C14 0.1(5) . . . . no N2 C3 C16 C15 178.8(3) . . . . no C2 C3 C16 C15 0.8(5) . . . . no N2 C4 C5 C6 -177.9(3) . . . . no C9 C4 C5 C6 1.2(5) . . . . no C5 C4 C9 C8 -1.1(5) . . . . no C5 C4 C9 N3 179.6(3) . . . . no N2 C4 C9 C8 178.0(3) . . . . no N2 C4 C9 N3 -1.4(4) . . . . no C4 C5 C6 C7 -0.6(5) . . . . no C5 C6 C7 C8 -0.1(5) . . . . no C6 C7 C8 C9 0.2(5) . . . . no C7 C8 C9 C4 0.4(5) . . . . no C7 C8 C9 N3 179.7(3) . . . . no N4 C11 C17 C18 178.8(3) . . . . no C12 C11 C17 C18 -0.3(5) . . . . no C17 C11 C12 C20 0.3(5) . . . . no N4 C11 C12 N3 -0.8(3) . . . . no N4 C11 C12 C20 -178.9(3) . . . . no C17 C11 C12 N3 178.5(3) . . . . no N3 C12 C20 C19 -177.8(3) . . . . no C11 C12 C20 C19 -0.2(5) . . . . no C2 C13 C14 C15 0.2(5) . . . . no C13 C14 C15 C16 0.0(5) . . . . no C14 C15 C16 C3 -0.5(5) . . . . no C11 C17 C18 C19 0.1(6) . . . . no C17 C18 C19 C20 0.0(6) . . . . no C18 C19 C20 C12 0.1(6) . . . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C17 H17 Br1 0.9500 2.9100 3.690(3) 140.00 1_545 yes C23 H23B Br2 0.9800 2.8300 3.796(4) 169.00 2_566 yes # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.500 82 19 ' ' _platon_squeeze_details ; The unit cell contains 1 disordered acetonitrile molecule at a which has been treated as a diffuse contribution to the overall scattering without specific atom positions by SQUEEZE/PLATON. ; _iucr_refine_instructions_details ; TITL MD1533 CELL 0.71073 9.7310 10.7520 13.9470 96.0850 103.7530 98.4780 ZERR 2 0.0012 0.0024 0.0007 0.0085 0.0064 0.0146 LATT 1 SFAC C H Br N Pd UNIT 52 48 4 12 2 LIST 4 ACTA BOND $H CONF FMAP 2 PLAN -15 L.S. 6 TEMP -75 OMIT 0 -1 1 OMIT 1 0 0 OMIT -1 0 1 OMIT 0 1 1 SIZE 0.186 0.188 0.329 WGHT 0.0203 1.4433 FVAR 1.01176 PD1 5 0.173242 0.335946 0.231727 11.00000 0.01915 0.02306 = 0.01950 0.00215 0.00266 -0.00043 C1 1 0.317627 0.351623 0.155037 11.00000 0.02226 0.01663 = 0.01979 0.00145 0.00038 0.00125 BR1 3 0.093698 0.531217 0.178100 11.00000 0.03119 0.02933 = 0.03637 0.00771 0.00780 0.00747 BR2 3 -0.006391 0.296246 0.331027 11.00000 0.03208 0.04579 = 0.02885 0.00483 0.01231 -0.00093 C2 1 0.430563 0.340497 0.031754 11.00000 0.02363 0.01828 = 0.02323 0.00639 0.00397 0.00155 N1 4 0.298496 0.331152 0.055974 11.00000 0.01887 0.02279 = 0.01857 0.00139 -0.00066 -0.00008 N2 4 0.462087 0.374918 0.196328 11.00000 0.01977 0.02448 = 0.01718 0.00373 0.00061 0.00095 N4 4 0.201209 0.064110 0.241963 11.00000 0.03520 0.02237 = 0.02840 0.00163 0.01045 -0.00227 C4 1 0.527261 0.399310 0.301031 11.00000 0.01702 0.02550 = 0.02018 0.00183 -0.00055 0.00362 C23 1 0.031425 0.677581 0.400300 11.00000 0.05893 0.08752 = 0.03532 0.01275 0.01674 0.02890 AFIX 137 H23A 2 0.014588 0.585241 0.380724 11.00000 -1.50000 H23B 2 0.023267 0.696713 0.468793 11.00000 -1.50000 H23C 2 0.128018 0.714339 0.396577 11.00000 -1.50000 AFIX 0 C26 1 0.308465 -0.009931 -0.053281 11.00000 0.04958 0.04633 = 0.06627 0.01550 0.01135 0.01171 N3 4 0.396781 0.195076 0.322332 11.00000 0.03116 0.01946 = 0.02218 0.00574 0.00376 0.00247 C3 1 0.536471 0.369621 0.121329 11.00000 0.02471 0.01717 = 0.02287 0.00450 0.00634 0.00120 C8 1 0.564520 0.334325 0.463696 11.00000 0.03454 0.03610 = 0.02251 0.00778 0.00321 0.01057 AFIX 43 H8 2 0.544137 0.273856 0.505663 11.00000 -1.20000 AFIX 0 C5 1 0.623741 0.510977 0.341759 11.00000 0.02677 0.03087 = 0.02899 0.00300 0.00319 -0.00342 AFIX 43 H5 2 0.643847 0.572283 0.300362 11.00000 -1.20000 AFIX 0 C21 1 0.158707 0.300587 -0.017067 11.00000 0.02572 0.03802 = 0.02396 0.00061 -0.00310 0.00171 AFIX 137 H21A 2 0.149680 0.217520 -0.056727 11.00000 -1.50000 H21B 2 0.150555 0.365742 -0.061194 11.00000 -1.50000 H21C 2 0.082118 0.297997 0.017726 11.00000 -1.50000 AFIX 0 C9 1 0.496476 0.310615 0.362568 11.00000 0.02263 0.02702 = 0.02194 0.00217 0.00183 0.00628 C20 1 0.549886 0.028171 0.374346 11.00000 0.05379 0.03990 = 0.03086 0.01121 0.00848 0.01941 AFIX 43 H20 2 0.636054 0.084124 0.410096 11.00000 -1.20000 AFIX 0 C11 1 0.301199 -0.010799 0.277639 11.00000 0.05187 0.02172 = 0.02433 0.00487 0.01725 0.00338 C24 1 -0.075387 0.731959 0.332872 11.00000 0.04278 0.05388 = 0.03462 0.00548 0.01887 0.00202 C19 1 0.539565 -0.103123 0.363264 11.00000 0.08316 0.04675 = 0.03792 0.01944 0.01933 0.03611 AFIX 43 H19 2 0.621100 -0.138130 0.392261 11.00000 -1.20000 AFIX 0 N5 4 -0.157793 0.774391 0.281163 11.00000 0.04867 0.05754 = 0.04912 0.01165 0.00441 0.00471 C18 1 0.413481 -0.184481 0.311026 11.00000 0.09841 0.02717 = 0.03394 0.00737 0.02526 0.01876 AFIX 43 H18 2 0.411502 -0.273592 0.305483 11.00000 -1.20000 AFIX 0 C22 1 0.057335 0.013850 0.178264 11.00000 0.03528 0.03661 = 0.04441 -0.00166 0.00452 -0.01237 AFIX 137 H22A 2 0.004447 0.083842 0.165911 11.00000 -1.50000 H22B 2 0.006318 -0.046611 0.211407 11.00000 -1.50000 H22C 2 0.064520 -0.029466 0.114653 11.00000 -1.50000 AFIX 0 C16 1 0.680821 0.384123 0.124570 11.00000 0.02318 0.02701 = 0.02946 0.00388 0.00283 0.00215 AFIX 43 H16 2 0.752921 0.402980 0.185983 11.00000 -1.20000 AFIX 0 C15 1 0.714948 0.369888 0.034386 11.00000 0.02725 0.02997 = 0.04418 0.00434 0.01391 0.00349 AFIX 43 H15 2 0.813207 0.379771 0.033374 11.00000 -1.20000 AFIX 0 C10 1 0.258789 0.187905 0.268872 11.00000 0.02781 0.02322 = 0.02060 0.00222 0.00753 0.00120 C14 1 0.608173 0.341085 -0.056359 11.00000 0.04023 0.03281 = 0.02936 0.00143 0.01764 0.00501 AFIX 43 H14 2 0.635987 0.332056 -0.117212 11.00000 -1.20000 AFIX 0 C13 1 0.464473 0.325663 -0.059198 11.00000 0.03531 0.02625 = 0.02278 -0.00022 0.00589 0.00122 AFIX 43 H13 2 0.392107 0.305831 -0.120465 11.00000 -1.20000 AFIX 0 C12 1 0.426997 0.072515 0.330135 11.00000 0.04581 0.02611 = 0.02142 0.00722 0.01332 0.01123 C6 1 0.691087 0.533370 0.443048 11.00000 0.02695 0.03887 = 0.03070 -0.00778 -0.00203 -0.00451 AFIX 43 H6 2 0.757844 0.609769 0.470855 11.00000 -1.20000 AFIX 0 C17 1 0.291940 -0.141023 0.267222 11.00000 0.07352 0.02585 = 0.03234 0.00659 0.02213 0.00554 AFIX 43 H17 2 0.205968 -0.197345 0.231623 11.00000 -1.20000 AFIX 0 N6 4 0.281908 0.012270 0.020056 11.00000 0.08671 0.08368 = 0.07267 0.02032 0.03643 0.02599 C7 1 0.661313 0.444866 0.503546 11.00000 0.03413 0.04690 = 0.01981 -0.00184 -0.00270 0.01005 AFIX 43 H7 2 0.707816 0.460399 0.572851 11.00000 -1.20000 AFIX 0 C25 1 0.342929 -0.036318 -0.148796 11.00000 0.06207 0.07121 = 0.06354 0.00014 0.01909 0.00592 AFIX 137 H25A 2 0.282372 -0.115775 -0.186231 11.00000 -1.50000 H25B 2 0.444363 -0.044438 -0.137113 11.00000 -1.50000 H25C 2 0.325206 0.033530 -0.187212 11.00000 -1.50000 REM ##### HKLF 4 REM MD1533 REM R1 = 0.0308 for 4437 Fo > 4sig(Fo) and 0.0527 for all 5686 data REM 320 parameters refined using 0 restraints END WGHT 0.0203 1.4433 REM Highest difference peak 0.496, deepest hole -0.540, 1-sigma level 0.090 Q1 1 0.0428 0.5636 0.2231 11.00000 0.05 0.50 Q2 1 0.0908 0.5063 0.2441 11.00000 0.05 0.44 Q3 1 0.0483 0.2571 0.3625 11.00000 0.05 0.44 Q4 1 0.0926 0.2226 0.0012 11.00000 0.05 0.43 Q5 1 0.1120 0.4438 0.1983 11.00000 0.05 0.42 Q6 1 0.4960 0.3766 0.1652 11.00000 0.05 0.40 Q7 1 0.3803 0.3928 0.1821 11.00000 0.05 0.39 Q8 1 0.0985 0.3514 -0.0024 11.00000 0.05 0.37 Q9 1 0.1679 0.2988 -0.0776 11.00000 0.05 0.37 Q10 1 0.2260 0.2410 0.2374 11.00000 0.05 0.36 Q11 1 0.0019 0.5256 0.1970 11.00000 0.05 0.36 Q12 1 -0.0126 0.6341 0.4622 11.00000 0.05 0.35 Q13 1 0.5028 -0.1518 0.3375 11.00000 0.05 0.35 Q14 1 0.5980 0.3417 0.1156 11.00000 0.05 0.34 Q15 1 0.2412 0.3174 0.0142 11.00000 0.05 0.34 ; data_Compound_11a _database_code_depnum_ccdc_archive 'CCDC 915851' #TrackingRef '16213_web_deposit_cif_file_2_ThomasStrassner_1355568752.11a.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_formula_moiety '(C26 H21 Br4 N4 Pd), 1.5(C H2 Cl2)' _chemical_formula_sum 'C27.50 H24 Br4 Cl3 N4 Pd' _chemical_formula_weight 942.906 _chemical_compound_source 'see text' 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' Br Br -0.2901 2.4595 ' 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' N N 0.0061 0.0033 ' 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' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_space_group_name_H-M 'P b c n' _symmetry_Int_Tables_number 60 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,y,1/2-z 5 -x,-y,-z 6 1/2+x,1/2+y,1/2-z 7 1/2-x,1/2+y,z 8 x,-y,1/2+z _cell_length_a 21.297(2) _cell_length_b 18.653(5) _cell_length_c 15.986(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 6351(2) _cell_formula_units_Z 8 _cell_measurement_temperature 198 _cell_measurement_reflns_used 791 _cell_measurement_theta_min 4.081 _cell_measurement_theta_max 24.234 _exptl_crystal_description fragment _exptl_crystal_colour yellow _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.150 _exptl_crystal_density_diffrn 1.972 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 3632 _exptl_absorpt_coefficient_mu 5.896 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 2002' _exptl_absorpt_correction_T_min 0.385 _exptl_absorpt_correction_T_max 0.472 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 198 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method \f _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_wavelength_id x-ray # number of measured reflections (redundant set) _diffrn_reflns_number 148489 _diffrn_reflns_av_R_equivalents 0.0736 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.80 _diffrn_reflns_theta_max 26.40 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 6472 # number of observed reflections (> n sig(I)) _reflns_number_gt 4896 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius BV, 1999)' _computing_cell_refinement 'Dirax/lsq (Duisenberg, 1992)' _computing_data_reduction 'EvalCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SIR92(Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2011)' _computing_publication_material 'PLATON (Spek, 2011), enCIFer (Allen, 2004)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs 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^)+(0.0056P)^2^+16.6044P] 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_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 6472 _refine_ls_number_parameters 357 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0537 _refine_ls_wR_factor_gt 0.0477 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.687 _refine_diff_density_min -0.720 _refine_diff_density_rms 0.105 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd Uani 0.18756(1) 0.39082(1) 0.25605(1) 1.000 0.0207(1) d . . . Br1 Br Uani 0.26847(2) 0.47812(2) 0.21017(3) 1.000 0.0383(1) d . . . Br2 Br Uani 0.15556(2) 0.36543(2) 0.10958(2) 1.000 0.0341(1) d . . . Br3 Br Uani 0.02361(2) 0.66915(2) 0.42021(3) 1.000 0.0502(1) d . . . Br4 Br Uani -0.08476(2) 0.56659(3) 0.32338(3) 1.000 0.0498(2) d . . . N1 N Uani 0.26032(13) 0.40075(17) 0.41705(18) 1.000 0.0307(10) d . . . N2 N Uani 0.16740(13) 0.44322(15) 0.42839(17) 1.000 0.0237(9) d . . . N3 N Uani 0.07152(13) 0.35370(16) 0.34820(17) 1.000 0.0239(9) d . . . N4 N Uani 0.10825(13) 0.25873(15) 0.29105(17) 1.000 0.0238(9) d . . . C1 C Uani 0.20721(15) 0.41080(19) 0.3736(2) 1.000 0.0238(11) d . . . C2 C Uani 0.25486(19) 0.4277(2) 0.4978(2) 1.000 0.0377(14) d . . . C3 C Uani 0.19716(17) 0.4549(2) 0.5051(2) 1.000 0.0327(11) d . . . C4 C Uani 0.10679(16) 0.47007(19) 0.40699(19) 1.000 0.0231(10) d . . . C5 C Uani 0.09320(17) 0.54095(19) 0.4249(2) 1.000 0.0268(11) d . . . C6 C Uani 0.03590(17) 0.5699(2) 0.4026(2) 1.000 0.0294(11) d . . . C7 C Uani -0.00890(17) 0.5283(2) 0.3642(2) 1.000 0.0314(11) d . . . C8 C Uani 0.00311(17) 0.45638(19) 0.3497(2) 1.000 0.0271(11) d . . . C9 C Uani 0.06118(15) 0.42700(19) 0.3687(2) 1.000 0.0228(10) d . . . C10 C Uani 0.12015(15) 0.32904(19) 0.30071(19) 1.000 0.0215(11) d . . . C11 C Uani 0.05293(17) 0.2398(2) 0.3305(2) 1.000 0.0307(12) d . . . C12 C Uani 0.02899(17) 0.2989(2) 0.3653(2) 1.000 0.0304(11) d . . . C13 C Uani 0.31903(16) 0.3706(2) 0.3827(2) 1.000 0.0367(13) d . . . C14 C Uani 0.31198(17) 0.2942(2) 0.3534(2) 1.000 0.0340(13) d . . . C15 C Uani 0.2962(2) 0.2405(3) 0.4086(3) 1.000 0.0470(17) d . . . C16 C Uani 0.2902(2) 0.1708(3) 0.3821(4) 1.000 0.0580(19) d . . . C17 C Uani 0.3009(2) 0.1539(3) 0.3000(4) 1.000 0.060(2) d . . . C18 C Uani 0.3166(2) 0.2068(3) 0.2431(3) 1.000 0.0557(17) d . . . C19 C Uani 0.32182(19) 0.2769(2) 0.2698(3) 1.000 0.0440(16) d . . . C20 C Uani 0.14988(16) 0.20715(18) 0.2481(2) 1.000 0.0294(11) d . . . C21 C Uani 0.11343(17) 0.1573(2) 0.1917(2) 1.000 0.0315(11) d . . . C22 C Uani 0.09554(18) 0.1781(3) 0.1126(3) 1.000 0.0440(14) d . . . C23 C Uani 0.0604(2) 0.1334(4) 0.0628(3) 1.000 0.069(2) d . . . C24 C Uani 0.0437(3) 0.0665(4) 0.0921(5) 1.000 0.091(3) d . . . C25 C Uani 0.0624(3) 0.0445(3) 0.1688(5) 1.000 0.086(3) d . . . C26 C Uani 0.0973(2) 0.0901(2) 0.2194(3) 1.000 0.0533(17) d . . . Cl1 Cl Uani 0.35977(12) 0.71838(16) 0.52822(13) 1.000 0.1472(13) d . . . Cl2 Cl Uani 0.36334(10) 0.57614(13) 0.45770(13) 1.000 0.1311(10) d . . . C27 C Uani 0.3397(3) 0.6283(5) 0.5421(4) 1.000 0.115(4) d . . . Cl3 Cl Uani 0.49359(10) 0.35098(8) 0.33896(9) 1.000 0.1000(7) d . . . C28 C Uani 0.50000 0.2980(4) 0.25000 1.000 0.056(2) d S . . H2 H Uiso 0.28630 0.42700 0.53990 1.000 0.0450 c R . . H3 H Uiso 0.17980 0.47760 0.55300 1.000 0.0390 c R . . H5 H Uiso 0.12340 0.56990 0.45260 1.000 0.0320 c R . . H8 H Uiso -0.02880 0.42690 0.32650 1.000 0.0330 c R . . H11 H Uiso 0.03510 0.19320 0.33250 1.000 0.0370 c R . . H12 H Uiso -0.00930 0.30270 0.39550 1.000 0.0360 c R . . H13A H Uiso 0.35210 0.37260 0.42620 1.000 0.0440 c R . . H13B H Uiso 0.33300 0.40050 0.33500 1.000 0.0440 c R . . H15 H Uiso 0.28940 0.25180 0.46590 1.000 0.0560 c R . . H16 H Uiso 0.27860 0.13440 0.42060 1.000 0.0700 c R . . H17A H Uiso 0.26260 0.13000 0.27870 1.000 0.0720 c R . . H17B H Uiso 0.33490 0.11780 0.29880 1.000 0.0720 c R . . H18 H Uiso 0.32380 0.19490 0.18610 1.000 0.0670 c R . . H19 H Uiso 0.33220 0.31360 0.23090 1.000 0.0530 c R . . H20A H Uiso 0.17290 0.17860 0.29030 1.000 0.0350 c R . . H20B H Uiso 0.18120 0.23380 0.21440 1.000 0.0350 c R . . H22 H Uiso 0.10770 0.22390 0.09210 1.000 0.0530 c R . . H23 H Uiso 0.04760 0.14850 0.00860 1.000 0.0820 c R . . H24 H Uiso 0.01890 0.03560 0.05820 1.000 0.1090 c R . . H25 H Uiso 0.05160 -0.00210 0.18810 1.000 0.1030 c R . . H26 H Uiso 0.11010 0.07470 0.27340 1.000 0.0640 c R . . H27A H Uiso 0.35970 0.61010 0.59380 1.000 0.1390 c R . . H27B H Uiso 0.29360 0.62420 0.54900 1.000 0.1390 c R . . H28A H Uiso 0.53750 0.26680 0.25480 0.500 0.0670 c RP . . H28B H Uiso 0.46250 0.26680 0.24520 0.500 0.0670 c RP . . 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 0.0189(1) 0.0254(1) 0.0179(1) -0.0026(1) 0.0014(1) 0.0015(1) Br1 0.0349(2) 0.0385(2) 0.0414(2) 0.0020(2) 0.0049(2) -0.0096(2) Br2 0.0414(2) 0.0424(2) 0.0184(2) 0.0015(2) -0.0023(2) -0.0039(2) Br3 0.0738(3) 0.0358(2) 0.0409(2) -0.0065(2) -0.0040(2) 0.0257(2) Br4 0.0317(2) 0.0688(3) 0.0490(3) 0.0055(2) 0.0004(2) 0.0252(2) N1 0.0220(16) 0.042(2) 0.0280(16) -0.0095(14) -0.0051(13) 0.0059(14) N2 0.0221(15) 0.0281(17) 0.0208(15) -0.0050(12) -0.0014(12) 0.0039(12) N3 0.0233(16) 0.0273(17) 0.0211(14) -0.0036(12) 0.0011(12) 0.0009(13) N4 0.0243(15) 0.0255(17) 0.0217(14) -0.0022(12) -0.0011(13) 0.0016(13) C1 0.0201(17) 0.027(2) 0.0244(18) -0.0020(15) 0.0005(14) 0.0030(14) C2 0.037(2) 0.051(3) 0.0251(19) -0.0110(18) -0.0102(18) 0.009(2) C3 0.033(2) 0.045(2) 0.0201(18) -0.0101(16) -0.0048(16) 0.0046(18) C4 0.0218(18) 0.031(2) 0.0166(16) -0.0005(14) 0.0024(14) 0.0053(15) C5 0.029(2) 0.029(2) 0.0225(18) -0.0038(15) 0.0008(15) 0.0028(16) C6 0.037(2) 0.032(2) 0.0192(18) -0.0011(15) 0.0067(16) 0.0151(17) C7 0.024(2) 0.044(2) 0.0261(19) 0.0049(17) 0.0048(16) 0.0120(17) C8 0.0200(17) 0.038(2) 0.0234(18) -0.0006(15) 0.0012(15) -0.0006(17) C9 0.0203(17) 0.029(2) 0.0190(17) -0.0020(14) 0.0042(14) 0.0018(15) C10 0.0199(18) 0.027(2) 0.0175(17) 0.0013(14) -0.0029(14) 0.0037(15) C11 0.032(2) 0.032(2) 0.028(2) -0.0008(16) 0.0030(17) -0.0065(17) C12 0.027(2) 0.040(2) 0.0241(19) -0.0026(17) 0.0064(16) -0.0082(18) C13 0.0182(18) 0.055(3) 0.037(2) -0.0097(19) -0.0044(17) 0.0107(18) C14 0.0199(18) 0.047(3) 0.035(2) -0.0021(18) -0.0025(17) 0.0170(18) C15 0.041(3) 0.055(3) 0.045(3) 0.007(2) -0.001(2) 0.018(2) C16 0.041(3) 0.056(3) 0.077(4) 0.014(3) 0.005(3) 0.018(2) C17 0.027(2) 0.044(3) 0.109(5) -0.011(3) -0.009(3) 0.020(2) C18 0.051(3) 0.058(3) 0.058(3) -0.020(3) 0.005(2) 0.020(2) C19 0.039(2) 0.050(3) 0.043(3) -0.004(2) 0.002(2) 0.016(2) C20 0.0271(19) 0.027(2) 0.034(2) -0.0040(17) -0.0002(17) 0.0078(15) C21 0.0206(19) 0.029(2) 0.045(2) -0.0147(17) 0.0022(17) 0.0079(16) C22 0.034(2) 0.062(3) 0.036(2) -0.017(2) -0.0005(19) 0.009(2) C23 0.042(3) 0.112(5) 0.052(3) -0.050(3) -0.008(2) 0.014(3) C24 0.052(3) 0.104(6) 0.116(6) -0.083(5) -0.010(4) -0.006(4) C25 0.071(4) 0.050(4) 0.137(6) -0.043(4) 0.001(4) -0.017(3) C26 0.056(3) 0.034(3) 0.070(3) -0.011(2) -0.003(2) -0.002(2) Cl1 0.1396(19) 0.206(3) 0.0961(15) -0.0121(16) 0.0283(13) -0.0657(19) Cl2 0.1319(17) 0.158(2) 0.1035(14) 0.0460(14) 0.0494(13) 0.0361(15) C27 0.078(4) 0.212(9) 0.056(4) 0.022(5) 0.020(3) -0.030(5) Cl3 0.1691(17) 0.0725(10) 0.0584(9) -0.0176(7) 0.0289(10) -0.0424(11) C28 0.068(4) 0.053(4) 0.047(4) 0.0000 0.006(4) 0.0000 #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd1 Br1 2.4817(8) . . yes Pd1 Br2 2.4842(8) . . yes Pd1 C1 1.961(3) . . yes Pd1 C10 1.975(3) . . yes Br3 C6 1.891(4) . . yes Br4 C7 1.883(4) . . yes Cl1 C27 1.748(10) . . yes Cl2 C27 1.738(8) . . yes Cl3 C28 1.737(5) . . yes N1 C2 1.390(4) . . yes N1 C1 1.341(4) . . yes N1 C13 1.477(4) . . yes N2 C3 1.398(4) . . yes N2 C4 1.426(4) . . yes N2 C1 1.361(4) . . yes N3 C12 1.393(5) . . yes N3 C10 1.364(4) . . yes N3 C9 1.423(5) . . yes N4 C20 1.478(4) . . yes N4 C11 1.382(5) . . yes N4 C10 1.345(5) . . yes C2 C3 1.335(5) . . no C4 C9 1.401(5) . . no C4 C5 1.383(5) . . no C5 C6 1.381(5) . . no C6 C7 1.375(5) . . no C7 C8 1.385(5) . . no C8 C9 1.386(5) . . no C11 C12 1.336(5) . . no C13 C14 1.508(5) . . no C14 C19 1.391(6) . . no C14 C15 1.377(6) . . no C15 C16 1.373(8) . . no C16 C17 1.369(9) . . no C17 C18 1.383(8) . . no C18 C19 1.380(7) . . no C20 C21 1.510(5) . . no C21 C26 1.373(5) . . no C21 C22 1.377(6) . . no C22 C23 1.374(8) . . no C23 C24 1.380(10) . . no C24 C25 1.353(11) . . no C25 C26 1.389(8) . . no C2 H2 0.9500 . . no C3 H3 0.9500 . . no C5 H5 0.9500 . . no C8 H8 0.9500 . . no C11 H11 0.9500 . . no C12 H12 0.9500 . . no C13 H13B 0.9900 . . no C13 H13A 0.9900 . . no C15 H15 0.9500 . . no C16 H16 0.9500 . . no C17 H17B 0.9900 . . no C17 H17A 0.9900 . . no C18 H18 0.9500 . . no C19 H19 0.9500 . . no C20 H20B 0.9900 . . no C20 H20A 0.9900 . . no C22 H22 0.9500 . . no C23 H23 0.9500 . . no C24 H24 0.9500 . . no C25 H25 0.9500 . . no C26 H26 0.9500 . . no C27 H27A 0.9900 . . no C27 H27B 0.9900 . . no C28 H28A 0.9900 . . no C28 H28B 0.9900 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Br1 Pd1 Br2 92.12(2) . . . yes Br1 Pd1 C1 90.59(10) . . . yes Br1 Pd1 C10 174.07(10) . . . yes Br2 Pd1 C1 176.39(9) . . . yes Br2 Pd1 C10 91.73(9) . . . yes C1 Pd1 C10 85.39(13) . . . yes C1 N1 C2 111.1(3) . . . yes C1 N1 C13 125.1(3) . . . yes C2 N1 C13 123.6(3) . . . yes C1 N2 C3 110.6(3) . . . yes C1 N2 C4 124.4(3) . . . yes C3 N2 C4 124.5(3) . . . yes C9 N3 C10 124.7(3) . . . yes C9 N3 C12 124.0(3) . . . yes C10 N3 C12 110.8(3) . . . yes C10 N4 C11 110.9(3) . . . yes C10 N4 C20 125.1(3) . . . yes C11 N4 C20 123.9(3) . . . yes Pd1 C1 N1 130.6(2) . . . yes Pd1 C1 N2 124.6(2) . . . yes N1 C1 N2 104.7(3) . . . yes N1 C2 C3 107.2(3) . . . yes N2 C3 C2 106.4(3) . . . yes N2 C4 C5 118.4(3) . . . yes N2 C4 C9 122.1(3) . . . yes C5 C4 C9 119.6(3) . . . no C4 C5 C6 120.3(3) . . . no Br3 C6 C5 117.8(3) . . . yes Br3 C6 C7 121.5(3) . . . yes C5 C6 C7 120.5(3) . . . no Br4 C7 C6 122.4(3) . . . yes Br4 C7 C8 117.9(3) . . . yes C6 C7 C8 119.6(3) . . . no C7 C8 C9 120.7(3) . . . no N3 C9 C4 123.0(3) . . . yes N3 C9 C8 117.9(3) . . . yes C4 C9 C8 119.2(3) . . . no Pd1 C10 N3 123.8(3) . . . yes Pd1 C10 N4 131.7(2) . . . yes N3 C10 N4 104.5(3) . . . yes N4 C11 C12 107.7(3) . . . yes N3 C12 C11 106.0(3) . . . yes N1 C13 C14 113.0(3) . . . yes C13 C14 C15 120.9(3) . . . no C13 C14 C19 120.2(3) . . . no C15 C14 C19 118.9(4) . . . no C14 C15 C16 120.9(5) . . . no C15 C16 C17 119.9(5) . . . no C16 C17 C18 120.4(5) . . . no C17 C18 C19 119.5(5) . . . no C14 C19 C18 120.3(4) . . . no N4 C20 C21 111.7(3) . . . yes C20 C21 C22 121.2(4) . . . no C20 C21 C26 119.9(3) . . . no C22 C21 C26 119.0(4) . . . no C21 C22 C23 120.8(5) . . . no C22 C23 C24 119.5(5) . . . no C23 C24 C25 120.4(6) . . . no C24 C25 C26 120.0(6) . . . no C21 C26 C25 120.3(5) . . . no N1 C2 H2 126.00 . . . no C3 C2 H2 126.00 . . . no N2 C3 H3 127.00 . . . no C2 C3 H3 127.00 . . . no C4 C5 H5 120.00 . . . no C6 C5 H5 120.00 . . . no C7 C8 H8 120.00 . . . no C9 C8 H8 120.00 . . . no N4 C11 H11 126.00 . . . no C12 C11 H11 126.00 . . . no N3 C12 H12 127.00 . . . no C11 C12 H12 127.00 . . . no N1 C13 H13A 109.00 . . . no N1 C13 H13B 109.00 . . . no C14 C13 H13A 109.00 . . . no C14 C13 H13B 109.00 . . . no H13A C13 H13B 108.00 . . . no C14 C15 H15 120.00 . . . no C16 C15 H15 120.00 . . . no C15 C16 H16 120.00 . . . no C17 C16 H16 120.00 . . . no C16 C17 H17A 107.00 . . . no C16 C17 H17B 107.00 . . . no C18 C17 H17A 107.00 . . . no C18 C17 H17B 107.00 . . . no H17A C17 H17B 107.00 . . . no C17 C18 H18 120.00 . . . no C19 C18 H18 120.00 . . . no C14 C19 H19 120.00 . . . no C18 C19 H19 120.00 . . . no N4 C20 H20A 109.00 . . . no N4 C20 H20B 109.00 . . . no C21 C20 H20A 109.00 . . . no C21 C20 H20B 109.00 . . . no H20A C20 H20B 108.00 . . . no C21 C22 H22 120.00 . . . no C23 C22 H22 120.00 . . . no C22 C23 H23 120.00 . . . no C24 C23 H23 120.00 . . . no C23 C24 H24 120.00 . . . no C25 C24 H24 120.00 . . . no C24 C25 H25 120.00 . . . no C26 C25 H25 120.00 . . . no C21 C26 H26 120.00 . . . no C25 C26 H26 120.00 . . . no Cl1 C27 Cl2 111.6(4) . . . yes Cl1 C27 H27A 109.00 . . . no Cl1 C27 H27B 109.00 . . . no Cl2 C27 H27A 109.00 . . . no Cl2 C27 H27B 109.00 . . . no H27A C27 H27B 108.00 . . . no Cl3 C28 Cl3 110.7(4) . . 4_655 yes Cl3 C28 H28A 110.00 . . . no Cl3 C28 H28B 110.00 . . . no H28A C28 H28B 108.00 . . . no Cl3 C28 H28A 110.00 4_655 . . no Cl3 C28 H28B 110.00 4_655 . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br1 Pd1 C1 N1 -62.8(3) . . . . no Br1 Pd1 C1 N2 113.3(3) . . . . no C10 Pd1 C1 N1 121.6(4) . . . . no C10 Pd1 C1 N2 -62.3(3) . . . . no Br2 Pd1 C10 N3 -116.0(3) . . . . no Br2 Pd1 C10 N4 60.7(3) . . . . no C1 Pd1 C10 N3 61.9(3) . . . . no C1 Pd1 C10 N4 -121.5(3) . . . . no C2 N1 C1 Pd1 175.4(3) . . . . no C13 N1 C1 Pd1 0.2(5) . . . . no C2 N1 C1 N2 -1.2(4) . . . . no C13 N1 C1 N2 -176.5(3) . . . . no C1 N1 C13 C14 -63.4(4) . . . . no C2 N1 C13 C14 121.9(3) . . . . no C13 N1 C2 C3 175.6(3) . . . . no C1 N1 C2 C3 0.2(4) . . . . no C4 N2 C1 N1 174.0(3) . . . . no C3 N2 C1 N1 1.8(4) . . . . no C1 N2 C4 C5 -125.3(4) . . . . no C1 N2 C3 C2 -1.7(4) . . . . no C4 N2 C3 C2 -173.9(3) . . . . no C3 N2 C4 C9 -134.1(3) . . . . no C3 N2 C4 C5 45.9(5) . . . . no C1 N2 C4 C9 54.7(5) . . . . no C3 N2 C1 Pd1 -175.2(2) . . . . no C4 N2 C1 Pd1 -2.9(5) . . . . no C10 N3 C12 C11 2.1(4) . . . . no C12 N3 C10 N4 -1.8(3) . . . . no C9 N3 C12 C11 174.8(3) . . . . no C12 N3 C9 C8 -46.1(4) . . . . no C9 N3 C10 Pd1 3.0(4) . . . . no C12 N3 C10 Pd1 175.6(2) . . . . no C9 N3 C10 N4 -174.4(3) . . . . no C10 N3 C9 C8 125.6(3) . . . . no C10 N3 C9 C4 -54.6(5) . . . . no C12 N3 C9 C4 133.8(3) . . . . no C11 N4 C10 Pd1 -176.3(2) . . . . no C20 N4 C10 N3 -176.1(3) . . . . no C10 N4 C11 C12 0.4(4) . . . . no C10 N4 C20 C21 -136.7(3) . . . . no C11 N4 C20 C21 46.7(4) . . . . no C20 N4 C11 C12 177.4(3) . . . . no C20 N4 C10 Pd1 6.8(5) . . . . no C11 N4 C10 N3 0.9(3) . . . . no N1 C2 C3 N2 0.9(4) . . . . no C5 C4 C9 C8 -0.2(5) . . . . no N2 C4 C5 C6 177.7(3) . . . . no C5 C4 C9 N3 179.9(3) . . . . no N2 C4 C9 N3 0.0(5) . . . . no N2 C4 C9 C8 179.9(3) . . . . no C9 C4 C5 C6 -2.3(5) . . . . no C4 C5 C6 C7 1.6(5) . . . . no C4 C5 C6 Br3 -174.5(2) . . . . no Br3 C6 C7 C8 177.5(3) . . . . no Br3 C6 C7 Br4 1.8(4) . . . . no C5 C6 C7 C8 1.6(5) . . . . no C5 C6 C7 Br4 -174.2(3) . . . . no C6 C7 C8 C9 -4.1(5) . . . . no Br4 C7 C8 C9 171.9(3) . . . . no C7 C8 C9 N3 -176.8(3) . . . . no C7 C8 C9 C4 3.3(5) . . . . no N4 C11 C12 N3 -1.5(4) . . . . no N1 C13 C14 C15 -62.2(4) . . . . no N1 C13 C14 C19 118.3(4) . . . . no C13 C14 C15 C16 -179.5(4) . . . . no C15 C14 C19 C18 -0.8(6) . . . . no C19 C14 C15 C16 0.0(6) . . . . no C13 C14 C19 C18 178.7(4) . . . . no C14 C15 C16 C17 1.0(7) . . . . no C15 C16 C17 C18 -1.2(7) . . . . no C16 C17 C18 C19 0.4(7) . . . . no C17 C18 C19 C14 0.6(6) . . . . no N4 C20 C21 C22 81.8(4) . . . . no N4 C20 C21 C26 -97.9(4) . . . . no C20 C21 C22 C23 -177.6(4) . . . . no C26 C21 C22 C23 2.0(6) . . . . no C20 C21 C26 C25 178.4(4) . . . . no C22 C21 C26 C25 -1.3(6) . . . . no C21 C22 C23 C24 -1.0(7) . . . . no C22 C23 C24 C25 -0.9(9) . . . . no C23 C24 C25 C26 1.6(10) . . . . no C24 C25 C26 C21 -0.6(8) . . . . no 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C5 H5 Br2 0.9500 2.8700 3.678(3) 144.00 8_565 yes C13 H13B Br1 0.9900 2.8200 3.576(4) 133.00 . yes C17 H17B Br4 0.9900 2.7700 3.532(5) 135.00 6_545 yes C22 H22 Br2 0.9500 2.8400 3.721(6) 154.00 . yes #===END