# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Thomas Strassner' 'Sebastian Ahrens' 'Yvonne Unger' 'Alexander Zeller' _publ_contact_author_name 'Thomas Strassner' _publ_contact_author_address ; Physikalische Organische Chemie Technische Universitat Dresden Bergstrasse 66 Dresden 01062 GERMANY ; _publ_contact_author_email THOMAS.STRASSNER@CHEMIE.TU-DRESDEN.DE _publ_requested_journal 'Chemical Communications' _publ_section_title ; Blue phosphorescent emitters: new N-heterocyclic platinum(II) tetracarbene complexes ; data_str-203 _database_code_depnum_ccdc_archive 'CCDC 680958' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 N8 Pt, I, I' _chemical_formula_sum 'C18 H24 I2 N8 Pt' _chemical_formula_weight 801.33 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' N N 0.0061 0.0033 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pt Pt -1.7033 8.3905 '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/c _symmetry_space_group_name_Hall '-P 2ybc' 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 10.422(1) _cell_length_b 9.778(1) _cell_length_c 12.131(1) _cell_angle_alpha 90.00 _cell_angle_beta 110.15(1) _cell_angle_gamma 90.00 _cell_volume 1160.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 757 _cell_measurement_theta_min 4.172 _cell_measurement_theta_max 31.288 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 8.727 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.051 _exptl_absorpt_correction_T_max 0.322 _exptl_absorpt_process_details 'SADABS 2.03.(Sheldrick,Bruker AXS Inc.,2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32989 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 29.40 _reflns_number_total 3203 _reflns_number_gt 3070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep III 1.0.3 (M.Burnett,C.Johnson,2000)' _computing_publication_material 'XCIF 6.12 (Sheldrick, 1997)' _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^)+(0.0233P)^2^+1.3207P] 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 3203 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0192 _refine_ls_R_factor_gt 0.0179 _refine_ls_wR_factor_ref 0.0473 _refine_ls_wR_factor_gt 0.0466 _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_restrained_S_all 1.135 _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 Pt1 Pt 1.0000 0.0000 1.0000 0.01140(5) Uani 1 2 d S . . I1 I 1.38339(18) 0.3511(2) 1.12785(15) 0.0290(6) Uani 0.50 1 d P . . C3 C 1.0295(3) 0.0792(3) 0.6693(2) 0.0226(5) Uani 1 1 d . . . H3A H 1.0813 0.1089 0.6229 0.027 Uiso 1 1 calc R . . C1 C 0.9726(2) 0.0249(2) 0.8277(2) 0.0139(4) Uani 1 1 d . . . N4 N 1.2524(2) -0.1919(2) 1.06268(18) 0.0201(4) Uani 1 1 d . . . N1 N 0.8651(2) 0.00397(19) 0.72872(19) 0.0158(4) Uani 1 1 d . . . N3 N 1.2545(2) -0.0312(2) 0.94368(18) 0.0179(4) Uani 1 1 d . . . N2 N 1.0735(2) 0.0697(2) 0.79056(17) 0.0169(4) Uani 1 1 d . . . C2 C 0.8982(3) 0.0377(3) 0.6307(2) 0.0217(5) Uani 1 1 d . . . H2A H 0.8392 0.0325 0.5512 0.026 Uiso 1 1 calc R . . C6 C 1.3652(3) -0.2138(3) 1.0291(2) 0.0274(6) Uani 1 1 d . . . H6A H 1.4294 -0.2862 1.0546 0.033 Uiso 1 1 calc R . . C5 C 1.3667(2) -0.1139(3) 0.9543(2) 0.0250(5) Uani 1 1 d . . . H5A H 1.4315 -0.1019 0.9159 0.030 Uiso 1 1 calc R . . C7 C 1.1828(2) -0.0801(2) 1.00905(19) 0.0156(4) Uani 1 1 d . . . C4 C 1.2123(2) 0.0899(3) 0.8712(2) 0.0203(5) Uani 1 1 d . . . H4A H 1.2746 0.1058 0.8265 0.024 Uiso 1 1 calc R . . H4B H 1.2162 0.1708 0.9212 0.024 Uiso 1 1 calc R . . C9 C 1.2162(3) -0.2796(3) 1.1442(2) 0.0284(6) Uani 1 1 d . . . H9A H 1.1166 -0.2803 1.1239 0.043 Uiso 1 1 calc R . . H9B H 1.2590 -0.2449 1.2243 0.043 Uiso 1 1 calc R . . H9C H 1.2484 -0.3728 1.1394 0.043 Uiso 1 1 calc R . . C8 C 0.7320(2) -0.0493(3) 0.7221(2) 0.0213(5) Uani 1 1 d . . . H8A H 0.7435 -0.1131 0.7872 0.032 Uiso 1 1 calc R . . H8B H 0.6902 -0.0972 0.6473 0.032 Uiso 1 1 calc R . . H8C H 0.6730 0.0265 0.7274 0.032 Uiso 1 1 calc R . . I1A I 0.61790(15) -0.35100(14) 0.87249(10) 0.0138(4) Uani 0.50 1 d P . . 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 0.00956(7) 0.01479(7) 0.01107(7) 0.00054(3) 0.00513(5) 0.00096(4) I1 0.0133(9) 0.0372(11) 0.0361(9) 0.0002(7) 0.0080(6) 0.0025(7) C3 0.0247(12) 0.0312(14) 0.0139(10) 0.0033(9) 0.0092(9) -0.0021(10) C1 0.0116(10) 0.0158(10) 0.0152(10) 0.0005(8) 0.0059(8) 0.0008(8) N4 0.0181(10) 0.0215(10) 0.0189(9) -0.0031(8) 0.0041(8) 0.0061(8) N1 0.0123(10) 0.0206(11) 0.0145(9) 0.0006(6) 0.0048(8) 0.0010(6) N3 0.0109(9) 0.0269(10) 0.0166(9) -0.0035(8) 0.0056(7) -0.0001(8) N2 0.0151(9) 0.0233(10) 0.0139(8) 0.0008(7) 0.0069(7) -0.0035(8) C2 0.0214(12) 0.0306(13) 0.0133(10) 0.0040(10) 0.0062(9) 0.0021(11) C6 0.0174(12) 0.0338(15) 0.0286(13) -0.0094(11) 0.0048(10) 0.0088(10) C5 0.0099(10) 0.0383(15) 0.0270(12) -0.0110(11) 0.0067(9) 0.0014(10) C7 0.0130(9) 0.0202(11) 0.0134(9) -0.0026(8) 0.0041(8) 0.0011(8) C4 0.0169(11) 0.0271(13) 0.0178(10) 0.0005(9) 0.0070(9) -0.0069(9) C9 0.0399(16) 0.0191(13) 0.0265(12) 0.0035(10) 0.0119(11) 0.0100(11) C8 0.0123(10) 0.0296(13) 0.0208(11) -0.0039(10) 0.0043(9) -0.0033(10) I1A 0.0181(9) 0.0138(6) 0.0127(5) 0.0009(4) 0.0095(5) 0.0027(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pt1 C1 2.025(2) 3_757 ? Pt1 C1 2.025(2) . ? Pt1 C7 2.027(2) 3_757 ? Pt1 C7 2.027(2) . ? C3 C2 1.348(4) . ? C3 N2 1.384(3) . ? C3 H3A 0.9500 . ? C1 N1 1.345(3) . ? C1 N2 1.352(3) . ? N4 C7 1.349(3) . ? N4 C6 1.387(3) . ? N4 C9 1.454(4) . ? N1 C2 1.387(3) . ? N1 C8 1.458(3) . ? N3 C7 1.351(3) . ? N3 C5 1.390(3) . ? N3 C4 1.450(3) . ? N2 C4 1.454(3) . ? C2 H2A 0.9500 . ? C6 C5 1.337(4) . ? C6 H6A 0.9500 . ? C5 H5A 0.9500 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Pt1 C1 180.00(13) 3_757 . ? C1 Pt1 C7 84.15(9) 3_757 3_757 ? C1 Pt1 C7 95.85(9) . 3_757 ? C1 Pt1 C7 95.85(9) 3_757 . ? C1 Pt1 C7 84.15(9) . . ? C7 Pt1 C7 180.000(1) 3_757 . ? C2 C3 N2 105.9(2) . . ? C2 C3 H3A 127.0 . . ? N2 C3 H3A 127.0 . . ? N1 C1 N2 104.8(2) . . ? N1 C1 Pt1 132.92(18) . . ? N2 C1 Pt1 122.24(17) . . ? C7 N4 C6 110.6(2) . . ? C7 N4 C9 125.7(2) . . ? C6 N4 C9 123.6(2) . . ? C1 N1 C2 110.7(2) . . ? C1 N1 C8 125.9(2) . . ? C2 N1 C8 123.4(2) . . ? C7 N3 C5 111.0(2) . . ? C7 N3 C4 122.1(2) . . ? C5 N3 C4 126.9(2) . . ? C1 N2 C3 111.4(2) . . ? C1 N2 C4 121.89(19) . . ? C3 N2 C4 126.4(2) . . ? C3 C2 N1 107.2(2) . . ? C3 C2 H2A 126.4 . . ? N1 C2 H2A 126.4 . . ? C5 C6 N4 107.2(2) . . ? C5 C6 H6A 126.4 . . ? N4 C6 H6A 126.4 . . ? C6 C5 N3 106.3(2) . . ? C6 C5 H5A 126.8 . . ? N3 C5 H5A 126.8 . . ? N4 C7 N3 104.8(2) . . ? N4 C7 Pt1 132.71(18) . . ? N3 C7 Pt1 122.10(18) . . ? N3 C4 N2 108.7(2) . . ? N3 C4 H4A 109.9 . . ? N2 C4 H4A 109.9 . . ? N3 C4 H4B 109.9 . . ? N2 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? N4 C9 H9A 109.5 . . ? N4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 Pt1 C1 N1 -42.5(2) 3_757 . . . ? C7 Pt1 C1 N1 137.5(2) . . . . ? C7 Pt1 C1 N2 138.1(2) 3_757 . . . ? C7 Pt1 C1 N2 -41.9(2) . . . . ? N2 C1 N1 C2 -0.9(3) . . . . ? Pt1 C1 N1 C2 179.6(2) . . . . ? N2 C1 N1 C8 177.8(2) . . . . ? Pt1 C1 N1 C8 -1.6(4) . . . . ? N1 C1 N2 C3 0.9(3) . . . . ? Pt1 C1 N2 C3 -179.56(18) . . . . ? N1 C1 N2 C4 -173.1(2) . . . . ? Pt1 C1 N2 C4 6.4(3) . . . . ? C2 C3 N2 C1 -0.6(3) . . . . ? C2 C3 N2 C4 173.1(3) . . . . ? N2 C3 C2 N1 0.0(3) . . . . ? C1 N1 C2 C3 0.6(3) . . . . ? C8 N1 C2 C3 -178.2(2) . . . . ? C7 N4 C6 C5 0.4(3) . . . . ? C9 N4 C6 C5 -179.9(2) . . . . ? N4 C6 C5 N3 0.4(3) . . . . ? C7 N3 C5 C6 -1.1(3) . . . . ? C4 N3 C5 C6 -179.4(2) . . . . ? C6 N4 C7 N3 -1.1(3) . . . . ? C9 N4 C7 N3 179.2(2) . . . . ? C6 N4 C7 Pt1 171.58(19) . . . . ? C9 N4 C7 Pt1 -8.1(4) . . . . ? C5 N3 C7 N4 1.4(3) . . . . ? C4 N3 C7 N4 179.7(2) . . . . ? C5 N3 C7 Pt1 -172.28(17) . . . . ? C4 N3 C7 Pt1 6.1(3) . . . . ? C1 Pt1 C7 N4 44.0(2) 3_757 . . . ? C1 Pt1 C7 N4 -136.0(2) . . . . ? C1 Pt1 C7 N3 -144.33(19) 3_757 . . . ? C1 Pt1 C7 N3 35.67(19) . . . . ? C7 N3 C4 N2 -56.1(3) . . . . ? C5 N3 C4 N2 122.0(3) . . . . ? C1 N2 C4 N3 48.9(3) . . . . ? C3 N2 C4 N3 -124.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.40 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.671 _refine_diff_density_min -2.162 _refine_diff_density_rms 0.166