# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Biprajit Sarkar' _publ_contact_author_email SARKAR@IAC.UNI-STUTTGART.DE _publ_section_title ; New 1, 2, 3-Triazole Ligands Through 'Click Reactions' and Their Palladium and Platinum Complexes ; loop_ _publ_author_name 'Biprajit Sarkar' 'Roberto Pattacini' 'David Schweinfurth' 'Sabine Strobel' # Attachment '1a_revised.cif' data_1a _database_code_depnum_ccdc_archive 'CCDC 733411' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C16 H16 Cl2 N4 Pd' _chemical_formula_sum 'C16 H16 Cl2 N4 Pd' _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour yellow _diffrn_ambient_temperature 173(2) _chemical_formula_weight 441.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Pd Pd -0.9988 1.0072 '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' 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_int_tables_number 61 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 6.8228(2) _cell_length_b 18.1883(6) _cell_length_c 27.2193(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3377.78(19) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3968 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.737 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 1.418 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7108 _diffrn_reflns_av_R_equivalents 0.0573 _diffrn_reflns_av_sigmaI/netI 0.0744 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3868 _reflns_number_gt 2522 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material PLATON _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^)+(0.0612P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3868 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0922 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1266 _refine_ls_wR_factor_gt 0.0903 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.87206(5) 0.94127(2) 0.790800(12) 0.01937(14) Uani 1 1 d . . . N1 N 0.8992(5) 1.0381(2) 0.75243(14) 0.0197(9) Uani 1 1 d . . . N2 N 0.8673(5) 0.9014(2) 0.72205(13) 0.0183(9) Uani 1 1 d . . . N3 N 0.8505(5) 0.8360(2) 0.70222(13) 0.0208(9) Uani 1 1 d . . . N4 N 0.8482(5) 0.8483(2) 0.65335(14) 0.0223(9) Uani 1 1 d . . . Cl1 Cl 0.84089(17) 0.82919(7) 0.82609(4) 0.0280(3) Uani 1 1 d . . . Cl2 Cl 0.87651(18) 0.99668(7) 0.86615(4) 0.0327(3) Uani 1 1 d . . . C1 C 0.9212(7) 1.1058(3) 0.77160(19) 0.0247(11) Uani 1 1 d . . . H1 H 0.9225 1.1112 0.8056 0.030 Uiso 1 1 calc R . . C2 C 0.9418(7) 1.1674(3) 0.7425(2) 0.0300(12) Uani 1 1 d . . . H2 H 0.9589 1.2136 0.7566 0.036 Uiso 1 1 calc R . . C3 C 0.9365(7) 1.1591(3) 0.6922(2) 0.0310(12) Uani 1 1 d . . . H3 H 0.9491 1.1999 0.6719 0.037 Uiso 1 1 calc R . . C4 C 0.9126(7) 1.0904(3) 0.6721(2) 0.0285(12) Uani 1 1 d . . . H4 H 0.9083 1.0843 0.6382 0.034 Uiso 1 1 calc R . . C5 C 0.8951(6) 1.0310(3) 0.70294(17) 0.0219(11) Uani 1 1 d . . . C6 C 0.8747(6) 0.9546(3) 0.68677(18) 0.0211(11) Uani 1 1 d . . . C7 C 0.8618(6) 0.9202(3) 0.64256(18) 0.0242(11) Uani 1 1 d . . . H7 H 0.8624 0.9417 0.6116 0.029 Uiso 1 1 calc R . . C8 C 0.8300(7) 0.7888(3) 0.61887(16) 0.0218(11) Uani 1 1 d . . . C9 C 0.6896(7) 0.7932(3) 0.58273(17) 0.0292(12) Uani 1 1 d . . . H9 H 0.6030 0.8326 0.5819 0.035 Uiso 1 1 calc R . . C10 C 0.6788(8) 0.7382(3) 0.54766(17) 0.0307(13) Uani 1 1 d . . . H10 H 0.5834 0.7410 0.5233 0.037 Uiso 1 1 calc R . . C11 C 0.8073(8) 0.6791(3) 0.54805(17) 0.0283(12) Uani 1 1 d . . . C12 C 0.9471(7) 0.6762(3) 0.58565(17) 0.0272(12) Uani 1 1 d . . . H12 H 1.0333 0.6366 0.5870 0.033 Uiso 1 1 calc R . . C13 C 0.9602(7) 0.7304(3) 0.62071(17) 0.0244(11) Uani 1 1 d . . . H13 H 1.0549 0.7280 0.6452 0.029 Uiso 1 1 calc R . . C14 C 0.8048(8) 0.6187(3) 0.50920(18) 0.0337(13) Uani 1 1 d . . . H14 H 0.9401 0.6120 0.4980 0.040 Uiso 1 1 calc R . . C15 C 0.6824(9) 0.6366(4) 0.4644(2) 0.0519(18) Uani 1 1 d . . . H15A H 0.5464 0.6381 0.4734 0.078 Uiso 1 1 calc R . . H15B H 0.7021 0.5996 0.4398 0.078 Uiso 1 1 calc R . . H15C H 0.7209 0.6836 0.4516 0.078 Uiso 1 1 calc R . . C16 C 0.7387(11) 0.5460(3) 0.5312(2) 0.0530(18) Uani 1 1 d . . . H16A H 0.8162 0.5353 0.5598 0.080 Uiso 1 1 calc R . . H16B H 0.7550 0.5075 0.5075 0.080 Uiso 1 1 calc R . . H16C H 0.6031 0.5494 0.5404 0.080 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 0.0206(2) 0.0186(2) 0.0189(2) -0.00020(15) -0.00088(16) 0.00009(16) N1 0.018(2) 0.021(2) 0.019(2) -0.0002(17) -0.0020(17) 0.0013(16) N2 0.021(2) 0.016(2) 0.0174(19) 0.0002(16) -0.0013(16) 0.0007(17) N3 0.024(2) 0.021(2) 0.018(2) -0.0034(16) -0.0007(17) 0.0012(18) N4 0.025(2) 0.021(2) 0.021(2) 0.0012(17) 0.0014(17) -0.0003(18) Cl1 0.0338(7) 0.0240(7) 0.0260(6) 0.0055(5) -0.0006(5) 0.0007(6) Cl2 0.0454(8) 0.0291(7) 0.0236(6) -0.0047(6) -0.0003(6) -0.0038(6) C1 0.024(3) 0.022(3) 0.028(3) -0.004(2) -0.004(2) -0.002(2) C2 0.028(3) 0.021(3) 0.041(3) -0.003(2) -0.007(3) -0.001(2) C3 0.034(3) 0.023(3) 0.037(3) 0.007(2) -0.003(3) 0.000(2) C4 0.030(3) 0.026(3) 0.030(3) 0.005(2) -0.003(2) -0.004(2) C5 0.019(2) 0.022(3) 0.024(3) 0.000(2) 0.002(2) -0.001(2) C6 0.019(2) 0.020(3) 0.024(2) 0.002(2) 0.004(2) 0.000(2) C7 0.028(3) 0.021(3) 0.024(2) 0.005(2) 0.001(2) 0.002(2) C8 0.028(3) 0.021(3) 0.017(2) 0.000(2) 0.003(2) -0.007(2) C9 0.028(3) 0.033(3) 0.027(3) -0.004(2) -0.003(2) 0.002(2) C10 0.034(3) 0.038(3) 0.020(3) -0.004(2) -0.005(2) 0.003(3) C11 0.038(3) 0.028(3) 0.018(2) -0.003(2) 0.007(2) -0.006(3) C12 0.038(3) 0.021(3) 0.023(3) 0.001(2) -0.002(2) 0.000(3) C13 0.028(3) 0.022(3) 0.023(2) 0.002(2) -0.006(2) -0.002(2) C14 0.045(3) 0.033(3) 0.023(3) -0.005(2) -0.003(2) -0.001(3) C15 0.075(5) 0.052(4) 0.030(3) -0.009(3) -0.011(3) 0.013(4) C16 0.079(5) 0.039(4) 0.042(3) -0.008(3) -0.011(4) -0.014(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 N2 2.007(4) . ? Pd1 N1 2.055(4) . ? Pd1 Cl1 2.2635(13) . ? Pd1 Cl2 2.2854(13) . ? N1 C1 1.346(6) . ? N1 C5 1.354(6) . ? N2 N3 1.312(6) . ? N2 C6 1.364(6) . ? N3 N4 1.349(5) . ? N4 C7 1.343(6) . ? N4 C8 1.438(6) . ? C1 C2 1.380(7) . ? C1 H1 0.9300 . ? C2 C3 1.378(8) . ? C2 H2 0.9300 . ? C3 C4 1.373(7) . ? C3 H3 0.9300 . ? C4 C5 1.375(7) . ? C4 H4 0.9300 . ? C5 C6 1.464(7) . ? C6 C7 1.359(7) . ? C7 H7 0.9300 . ? C8 C9 1.375(6) . ? C8 C13 1.385(7) . ? C9 C10 1.384(7) . ? C9 H9 0.9300 . ? C10 C11 1.387(7) . ? C10 H10 0.9300 . ? C11 C12 1.400(7) . ? C11 C14 1.525(7) . ? C12 C13 1.375(6) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.514(7) . ? C14 C16 1.520(7) . ? C14 H14 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 N2 Pd1 N1 80.61(16) . . ? N2 Pd1 Cl1 93.96(12) . . ? N1 Pd1 Cl1 174.57(11) . . ? N2 Pd1 Cl2 174.99(12) . . ? N1 Pd1 Cl2 94.42(11) . . ? Cl1 Pd1 Cl2 91.01(5) . . ? C1 N1 C5 118.4(4) . . ? C1 N1 Pd1 126.6(3) . . ? C5 N1 Pd1 115.0(3) . . ? N3 N2 C6 110.9(4) . . ? N3 N2 Pd1 135.5(3) . . ? C6 N2 Pd1 113.6(3) . . ? N2 N3 N4 104.8(4) . . ? C7 N4 N3 112.1(4) . . ? C7 N4 C8 126.6(4) . . ? N3 N4 C8 121.3(4) . . ? N1 C1 C2 122.2(5) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C3 C2 C1 118.5(5) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C4 C3 C2 120.0(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 118.8(5) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? N1 C5 C4 122.1(5) . . ? N1 C5 C6 113.1(4) . . ? C4 C5 C6 124.8(4) . . ? C7 C6 N2 107.1(4) . . ? C7 C6 C5 135.2(5) . . ? N2 C6 C5 117.7(4) . . ? N4 C7 C6 105.0(4) . . ? N4 C7 H7 127.5 . . ? C6 C7 H7 127.5 . . ? C9 C8 C13 121.1(5) . . ? C9 C8 N4 118.9(5) . . ? C13 C8 N4 119.9(4) . . ? C8 C9 C10 119.2(5) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C9 C10 C11 121.4(5) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C10 C11 C12 117.7(5) . . ? C10 C11 C14 123.1(5) . . ? C12 C11 C14 119.1(5) . . ? C13 C12 C11 121.6(5) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C8 118.9(4) . . ? C12 C13 H13 120.6 . . ? C8 C13 H13 120.6 . . ? C15 C14 C16 110.0(5) . . ? C15 C14 C11 114.2(5) . . ? C16 C14 C11 110.9(4) . . ? C15 C14 H14 107.2 . . ? C16 C14 H14 107.2 . . ? C11 C14 H14 107.2 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.665 _refine_diff_density_min -1.309 _refine_diff_density_rms 0.301 # Attachment '3_revised.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 733412' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 N4' _chemical_formula_sum 'C13 H10 N4' _chemical_formula_weight 222.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.7757(2) _cell_length_b 19.3231(6) _cell_length_c 9.7917(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.295(2) _cell_angle_gamma 90.00 _cell_volume 1078.45(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2671 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 28.28 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5135 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 28.30 _reflns_number_total 2660 _reflns_number_gt 2095 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0420P)^2^+0.2974P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2660 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0926 _refine_ls_wR_factor_gt 0.0850 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.85076(17) 0.19796(5) -0.06851(10) 0.0179(2) Uani 1 1 d . . . N2 N 0.43590(17) 0.08831(5) 0.07382(11) 0.0219(2) Uani 1 1 d . . . N3 N 0.48461(17) 0.03913(5) 0.16588(11) 0.0221(2) Uani 1 1 d . . . N4 N 0.72075(16) 0.03046(5) 0.18792(10) 0.0163(2) Uani 1 1 d . . . C1 C 0.8567(2) 0.24818(6) -0.16264(12) 0.0193(3) Uani 1 1 d . . . H1 H 1.007(3) 0.2713(7) -0.1614(14) 0.022(3) Uiso 1 1 d . . . C2 C 0.6636(2) 0.26862(6) -0.25761(12) 0.0200(3) Uani 1 1 d . . . H2 H 0.680(3) 0.3044(8) -0.3268(15) 0.032(4) Uiso 1 1 d . . . C3 C 0.4510(2) 0.23627(6) -0.25287(12) 0.0200(3) Uani 1 1 d . . . H3 H 0.307(3) 0.2492(7) -0.3186(15) 0.026(4) Uiso 1 1 d . . . C4 C 0.4381(2) 0.18522(6) -0.15488(12) 0.0184(2) Uani 1 1 d . . . H4 H 0.294(2) 0.1627(7) -0.1478(13) 0.019(3) Uiso 1 1 d . . . C5 C 0.6421(2) 0.16712(6) -0.06590(11) 0.0155(2) Uani 1 1 d . . . C6 C 0.64021(19) 0.11172(6) 0.03676(11) 0.0156(2) Uani 1 1 d . . . C7 C 0.8235(2) 0.07482(6) 0.10891(11) 0.0154(2) Uani 1 1 d . . . H7 H 0.990(3) 0.0763(7) 0.1064(14) 0.025(4) Uiso 1 1 d . . . C8 C 0.8234(2) -0.02118(6) 0.28395(11) 0.0155(2) Uani 1 1 d . . . C9 C 0.7073(2) -0.03898(6) 0.39244(12) 0.0187(3) Uani 1 1 d . . . H9 H 0.564(3) -0.0165(8) 0.3995(14) 0.027(4) Uiso 1 1 d . . . C10 C 0.8018(2) -0.08946(6) 0.48511(13) 0.0226(3) Uani 1 1 d . . . H10 H 0.718(3) -0.1023(8) 0.5589(15) 0.029(4) Uiso 1 1 d . . . C11 C 1.0109(2) -0.12179(6) 0.47014(12) 0.0219(3) Uani 1 1 d . . . H11 H 1.080(2) -0.1576(8) 0.5370(14) 0.024(4) Uiso 1 1 d . . . C12 C 1.1261(2) -0.10285(6) 0.36158(12) 0.0199(3) Uani 1 1 d . . . H12 H 1.276(3) -0.1253(8) 0.3508(14) 0.027(4) Uiso 1 1 d . . . C13 C 1.0326(2) -0.05247(6) 0.26752(12) 0.0173(2) Uani 1 1 d . . . H13 H 1.112(2) -0.0391(7) 0.1929(15) 0.025(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0173(5) 0.0177(5) 0.0190(5) -0.0023(4) 0.0033(4) -0.0001(4) N2 0.0172(5) 0.0253(5) 0.0241(5) 0.0046(4) 0.0064(4) 0.0016(4) N3 0.0152(5) 0.0266(5) 0.0255(5) 0.0051(4) 0.0061(4) 0.0007(4) N4 0.0152(5) 0.0163(5) 0.0182(5) -0.0012(4) 0.0050(4) -0.0009(4) C1 0.0180(6) 0.0174(5) 0.0234(6) -0.0013(5) 0.0063(5) -0.0013(4) C2 0.0228(6) 0.0169(6) 0.0213(6) 0.0017(5) 0.0064(5) 0.0025(4) C3 0.0193(6) 0.0201(6) 0.0203(6) -0.0003(4) 0.0022(5) 0.0042(4) C4 0.0161(6) 0.0180(6) 0.0210(6) -0.0020(4) 0.0032(4) 0.0000(4) C5 0.0167(5) 0.0147(5) 0.0158(5) -0.0031(4) 0.0047(4) 0.0006(4) C6 0.0155(5) 0.0158(5) 0.0162(5) -0.0028(4) 0.0045(4) -0.0011(4) C7 0.0162(6) 0.0140(5) 0.0170(5) -0.0009(4) 0.0050(4) -0.0020(4) C8 0.0179(6) 0.0120(5) 0.0169(5) -0.0020(4) 0.0035(4) -0.0027(4) C9 0.0194(6) 0.0187(6) 0.0195(6) -0.0021(4) 0.0080(5) -0.0006(5) C10 0.0278(7) 0.0221(6) 0.0198(6) 0.0014(5) 0.0096(5) -0.0025(5) C11 0.0268(6) 0.0174(6) 0.0210(6) 0.0017(5) 0.0021(5) -0.0010(5) C12 0.0185(6) 0.0169(5) 0.0243(6) -0.0028(5) 0.0037(5) -0.0001(4) C13 0.0178(6) 0.0164(5) 0.0189(6) -0.0021(4) 0.0065(4) -0.0024(4) _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 N1 C1 1.3427(15) . ? N1 C5 1.3482(14) . ? N2 N3 1.3089(14) . ? N2 C6 1.3664(14) . ? N3 N4 1.3563(14) . ? N4 C7 1.3541(14) . ? N4 C8 1.4323(14) . ? C1 C2 1.3889(17) . ? C1 H1 0.977(15) . ? C2 C3 1.3853(17) . ? C2 H2 0.983(15) . ? C3 C4 1.3866(16) . ? C3 H3 0.997(15) . ? C4 C5 1.3924(16) . ? C4 H4 0.954(14) . ? C5 C6 1.4698(15) . ? C6 C7 1.3733(15) . ? C7 H7 0.967(15) . ? C8 C13 1.3836(16) . ? C8 C9 1.3880(15) . ? C9 C10 1.3829(17) . ? C9 H9 0.945(15) . ? C10 C11 1.3886(18) . ? C10 H10 0.963(15) . ? C11 C12 1.3910(17) . ? C11 H11 0.992(14) . ? C12 C13 1.3882(17) . ? C12 H12 0.988(15) . ? C13 H13 0.958(14) . ? 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 N1 C5 117.03(10) . . ? N3 N2 C6 108.93(10) . . ? N2 N3 N4 107.34(9) . . ? C7 N4 N3 110.67(9) . . ? C7 N4 C8 130.03(10) . . ? N3 N4 C8 119.30(9) . . ? N1 C1 C2 123.95(11) . . ? N1 C1 H1 116.3(8) . . ? C2 C1 H1 119.7(8) . . ? C3 C2 C1 117.99(11) . . ? C3 C2 H2 121.7(9) . . ? C1 C2 H2 120.3(9) . . ? C2 C3 C4 119.44(11) . . ? C2 C3 H3 121.0(8) . . ? C4 C3 H3 119.6(8) . . ? C3 C4 C5 118.47(11) . . ? C3 C4 H4 121.4(8) . . ? C5 C4 H4 120.1(8) . . ? N1 C5 C4 123.09(10) . . ? N1 C5 C6 116.14(10) . . ? C4 C5 C6 120.77(10) . . ? N2 C6 C7 108.57(10) . . ? N2 C6 C5 121.67(10) . . ? C7 C6 C5 129.76(10) . . ? N4 C7 C6 104.49(10) . . ? N4 C7 H7 124.2(8) . . ? C6 C7 H7 131.2(8) . . ? C13 C8 C9 121.32(11) . . ? C13 C8 N4 120.31(10) . . ? C9 C8 N4 118.37(10) . . ? C10 C9 C8 119.25(11) . . ? C10 C9 H9 122.2(9) . . ? C8 C9 H9 118.5(9) . . ? C9 C10 C11 120.39(11) . . ? C9 C10 H10 118.7(9) . . ? C11 C10 H10 120.9(9) . . ? C10 C11 C12 119.60(11) . . ? C10 C11 H11 120.6(8) . . ? C12 C11 H11 119.8(8) . . ? C13 C12 C11 120.58(11) . . ? C13 C12 H12 119.4(8) . . ? C11 C12 H12 120.0(8) . . ? C8 C13 C12 118.86(10) . . ? C8 C13 H13 120.3(9) . . ? C12 C13 H13 120.9(9) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.271 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.043 # Attachment '3b_revised.cif' data_3b _database_code_depnum_ccdc_archive 'CCDC 733413' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C13 H10 Cl2 N4 Pt' _chemical_formula_sum 'C13 H10 Cl2 N4 Pt' _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour yellow _diffrn_ambient_temperature 173(2) _chemical_formula_weight 488.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Pt Pt -1.7033 8.3905 '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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 7.5513(3) _cell_length_b 19.237(1) _cell_length_c 9.6692(7) _cell_angle_alpha 90.00 _cell_angle_beta 102.301(4) _cell_angle_gamma 90.00 _cell_volume 1372.34(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2501 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 26.373 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 10.607 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.195 _exptl_absorpt_correction_T_max 0.412 _exptl_absorpt_process_details 'L. Spek, J. Appl.Cryst. 2003, 36, 7, B. Blessing, Acta Cryst, 1995, A51, 33' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4587 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0621 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 26.35 _reflns_number_total 2773 _reflns_number_gt 2104 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material PLATON _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^)+(0.0484P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2773 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0977 _refine_ls_wR_factor_gt 0.0714 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pt1 Pt 0.22387(4) -0.054711(17) -0.13146(4) 0.02470(14) Uani 1 1 d . . . N1 N 0.1725(8) -0.0804(4) 0.0613(7) 0.0234(15) Uani 1 1 d . . . N2 N 0.2858(8) 0.0345(4) -0.0292(7) 0.0239(16) Uani 1 1 d . . . N3 N 0.3299(9) 0.0969(4) -0.0708(7) 0.0275(17) Uani 1 1 d . . . N4 N 0.3301(9) 0.1385(4) 0.0410(7) 0.0251(16) Uani 1 1 d . . . Cl1 Cl 0.3013(3) -0.01754(12) -0.3349(2) 0.0348(5) Uani 1 1 d . . . Cl2 Cl 0.1247(3) -0.15854(12) -0.2359(3) 0.0407(6) Uani 1 1 d . . . C1 C 0.1182(10) -0.1424(5) 0.1006(10) 0.030(2) Uani 1 1 d . . . H1 H 0.0970 -0.1782 0.0344 0.036 Uiso 1 1 calc R . . C2 C 0.0928(12) -0.1550(5) 0.2355(10) 0.034(2) Uani 1 1 d . . . H2 H 0.0593 -0.1990 0.2608 0.041 Uiso 1 1 calc R . . C3 C 0.1180(11) -0.1012(5) 0.3323(10) 0.033(2) Uani 1 1 d . . . H3 H 0.0983 -0.1083 0.4230 0.039 Uiso 1 1 calc R . . C4 C 0.1721(11) -0.0374(5) 0.2943(10) 0.031(2) Uani 1 1 d . . . H4 H 0.1910 -0.0009 0.3589 0.038 Uiso 1 1 calc R . . C5 C 0.1977(11) -0.0282(5) 0.1600(10) 0.029(2) Uani 1 1 d . . . C6 C 0.2555(10) 0.0374(4) 0.1033(10) 0.028(2) Uani 1 1 d . . . C7 C 0.2866(10) 0.1037(5) 0.1516(9) 0.027(2) Uani 1 1 d . . . H7 H 0.2796 0.1212 0.2399 0.032 Uiso 1 1 calc R . . C8 C 0.3691(11) 0.2112(4) 0.0325(9) 0.0274(19) Uani 1 1 d . . . C9 C 0.2826(11) 0.2579(5) 0.1048(9) 0.029(2) Uani 1 1 d . . . H9 H 0.2000 0.2426 0.1571 0.035 Uiso 1 1 calc R . . C10 C 0.3215(12) 0.3274(5) 0.0976(9) 0.034(2) Uani 1 1 d . . . H10 H 0.2656 0.3598 0.1456 0.040 Uiso 1 1 calc R . . C11 C 0.4432(12) 0.3491(5) 0.0193(9) 0.033(2) Uani 1 1 d . . . H11 H 0.4711 0.3961 0.0160 0.040 Uiso 1 1 calc R . . C12 C 0.5241(11) 0.3017(5) -0.0545(10) 0.036(2) Uani 1 1 d . . . H12 H 0.6036 0.3174 -0.1091 0.043 Uiso 1 1 calc R . . C13 C 0.4898(11) 0.2319(5) -0.0489(10) 0.031(2) Uani 1 1 d . . . H13 H 0.5453 0.1998 -0.0977 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 Pt1 0.0258(2) 0.0210(2) 0.0279(2) -0.00257(16) 0.00733(14) 0.00207(14) N1 0.020(3) 0.024(4) 0.027(4) 0.003(3) 0.005(3) 0.008(3) N2 0.024(4) 0.021(4) 0.026(4) -0.005(3) 0.004(3) 0.000(3) N3 0.029(4) 0.023(4) 0.031(4) 0.000(3) 0.008(3) -0.001(3) N4 0.029(4) 0.023(4) 0.023(4) -0.008(3) 0.004(3) 0.000(3) Cl1 0.0472(13) 0.0297(13) 0.0303(13) -0.0012(10) 0.0142(10) 0.0020(10) Cl2 0.0521(14) 0.0278(13) 0.0484(15) -0.0141(12) 0.0242(11) -0.0098(11) C1 0.025(5) 0.024(5) 0.043(6) 0.002(4) 0.011(4) 0.002(4) C2 0.043(5) 0.025(5) 0.038(6) 0.007(5) 0.017(4) 0.001(4) C3 0.032(5) 0.034(5) 0.034(5) 0.003(5) 0.011(4) 0.005(4) C4 0.033(5) 0.031(5) 0.029(6) 0.002(4) 0.005(4) -0.002(4) C5 0.023(4) 0.033(5) 0.033(5) 0.000(4) 0.011(4) 0.001(4) C6 0.026(5) 0.019(5) 0.036(6) -0.005(4) 0.002(4) 0.003(3) C7 0.028(4) 0.034(5) 0.019(5) 0.002(4) 0.005(4) 0.003(4) C8 0.030(4) 0.021(5) 0.029(5) 0.000(4) 0.001(4) -0.003(4) C9 0.037(5) 0.022(5) 0.033(6) -0.009(4) 0.017(4) -0.003(4) C10 0.049(5) 0.023(5) 0.030(5) -0.006(4) 0.011(4) -0.001(4) C11 0.041(5) 0.024(5) 0.034(5) 0.001(4) 0.006(4) -0.004(4) C12 0.031(5) 0.038(6) 0.041(6) 0.002(5) 0.015(4) -0.008(4) C13 0.028(4) 0.029(5) 0.037(6) -0.001(4) 0.009(4) 0.000(4) _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 Pt1 N2 1.987(7) . ? Pt1 N1 2.044(7) . ? Pt1 Cl1 2.283(2) . ? Pt1 Cl2 2.291(2) . ? N1 C1 1.342(10) . ? N1 C5 1.370(11) . ? N2 N3 1.331(10) . ? N2 C6 1.349(11) . ? N3 N4 1.344(9) . ? N4 C7 1.359(10) . ? N4 C8 1.435(10) . ? C1 C2 1.380(12) . ? C1 H1 0.9300 . ? C2 C3 1.382(12) . ? C2 H2 0.9300 . ? C3 C4 1.369(12) . ? C3 H3 0.9300 . ? C4 C5 1.365(12) . ? C4 H4 0.9300 . ? C5 C6 1.480(12) . ? C6 C7 1.361(12) . ? C7 H7 0.9300 . ? C8 C13 1.383(12) . ? C8 C9 1.386(11) . ? C9 C10 1.374(12) . ? C9 H9 0.9300 . ? C10 C11 1.374(12) . ? C10 H10 0.9300 . ? C11 C12 1.378(13) . ? C11 H11 0.9300 . ? C12 C13 1.372(12) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Pt1 N1 80.0(3) . . ? N2 Pt1 Cl1 94.7(2) . . ? N1 Pt1 Cl1 174.1(2) . . ? N2 Pt1 Cl2 173.2(2) . . ? N1 Pt1 Cl2 94.8(2) . . ? Cl1 Pt1 Cl2 90.75(9) . . ? C1 N1 C5 117.4(7) . . ? C1 N1 Pt1 127.0(6) . . ? C5 N1 Pt1 115.6(6) . . ? N3 N2 C6 110.7(7) . . ? N3 N2 Pt1 132.6(6) . . ? C6 N2 Pt1 116.0(6) . . ? N2 N3 N4 104.5(6) . . ? N3 N4 C7 112.4(7) . . ? N3 N4 C8 119.9(7) . . ? C7 N4 C8 127.7(7) . . ? N1 C1 C2 122.4(9) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 118.8(9) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 119.8(9) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 118.8(9) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 N1 122.8(8) . . ? C4 C5 C6 125.1(9) . . ? N1 C5 C6 112.1(7) . . ? N2 C6 C7 108.2(8) . . ? N2 C6 C5 116.1(8) . . ? C7 C6 C5 135.7(9) . . ? N4 C7 C6 104.1(8) . . ? N4 C7 H7 127.9 . . ? C6 C7 H7 127.9 . . ? C13 C8 C9 122.6(8) . . ? C13 C8 N4 118.8(8) . . ? C9 C8 N4 118.6(7) . . ? C10 C9 C8 118.5(8) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? C11 C10 C9 119.9(8) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 120.5(9) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 121.2(8) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C8 117.2(8) . . ? C12 C13 H13 121.4 . . ? C8 C13 H13 121.4 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.429 _refine_diff_density_min -1.473 _refine_diff_density_rms 0.326