# 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