# 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 _publ_contact_author_name 'Pierre Braunstein' _publ_contact_author_email BRAUNST@CHIMIE.U-STRASBG.FR _publ_section_title ; A new stable CNHC^CH^CNHC N-heterocyclic dicarbene ligand: its mono- and dinuclear Ir(I) and Ir(I)-Rh(I) complexes ; loop_ _publ_author_name 'Pierre Braunstein' 'Catherine Cazin' 'Helene Olivier-Bourbigou' 'Matthieu Raynal' 'Christophe Vallee' # Attachment 'Ir2_Complex_9.cif' data_import_MRP0212 _database_code_depnum_ccdc_archive 'CCDC 706832' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H46 Cl2 Ir2 N4' _chemical_formula_sum 'C34 H46 Cl2 Ir2 N4' _chemical_formula_weight 966.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5520(8) _cell_length_b 11.0660(8) _cell_length_c 15.0870(12) _cell_angle_alpha 101.543(5) _cell_angle_beta 98.061(4) _cell_angle_gamma 101.036(3) _cell_volume 1664.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 19564 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description Cube _exptl_crystal_colour yellow _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.927 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 8.176 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.410 _exptl_absorpt_correction_T_max 0.482 _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _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 19970 _diffrn_reflns_av_R_equivalents 0.0681 _diffrn_reflns_av_sigmaI/netI 0.0787 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 29.00 _reflns_number_total 8774 _reflns_number_gt 6327 _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, 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^)+(0.0437P)^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 8774 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0727 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1057 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 C1 C 0.4900(6) -0.3453(6) 0.3506(4) 0.0263(13) Uani 1 1 d . . . C2 C 0.6694(6) -0.4244(7) 0.3401(5) 0.0399(17) Uani 1 1 d . . . H2 H 0.7273 -0.4704 0.3166 0.048 Uiso 1 1 calc R . . C3 C 0.6890(7) -0.3491(7) 0.4230(5) 0.0426(18) Uani 1 1 d . . . H3 H 0.7637 -0.3320 0.4683 0.051 Uiso 1 1 calc R . . C4 C 0.5611(8) -0.2118(7) 0.5109(5) 0.0472(19) Uani 1 1 d . . . H4A H 0.4853 -0.1779 0.4942 0.057 Uiso 1 1 calc R . . H4B H 0.6375 -0.1417 0.5297 0.057 Uiso 1 1 calc R . . C5 C 0.5424(8) -0.2711(9) 0.5916(5) 0.063(2) Uani 1 1 d . . . H5A H 0.5350 -0.2077 0.6431 0.095 Uiso 1 1 calc R . . H5B H 0.6164 -0.3060 0.6081 0.095 Uiso 1 1 calc R . . H5C H 0.4637 -0.3372 0.5749 0.095 Uiso 1 1 calc R . . C6 C 0.4953(6) -0.4874(6) 0.1977(4) 0.0319(14) Uani 1 1 d . . . H6A H 0.4021 -0.4898 0.1845 0.038 Uiso 1 1 calc R . . H6B H 0.5059 -0.5740 0.1871 0.038 Uiso 1 1 calc R . . C7 C 0.5638(6) -0.4209(6) 0.1340(4) 0.0317(14) Uani 1 1 d . . . C8 C 0.6517(5) -0.4779(6) 0.0861(4) 0.0261(13) Uani 1 1 d . . . H8 H 0.6699 -0.5537 0.0960 0.031 Uiso 1 1 calc R . . C9 C 0.7110(6) -0.4183(6) 0.0238(4) 0.0312(14) Uani 1 1 d . . . H9 H 0.7680 -0.4553 -0.0085 0.037 Uiso 1 1 calc R . . C10 C 0.6852(6) -0.3047(6) 0.0100(4) 0.0283(13) Uani 1 1 d . . . H10 H 0.7242 -0.2667 -0.0321 0.034 Uiso 1 1 calc R . . C11 C 0.6017(5) -0.2468(5) 0.0585(4) 0.0242(12) Uani 1 1 d . . . C12 C 0.5416(6) -0.3083(6) 0.1198(4) 0.0273(13) Uani 1 1 d . . . H12 H 0.4845 -0.2709 0.1519 0.033 Uiso 1 1 calc R . . C13 C 0.5645(6) -0.1270(6) 0.0444(4) 0.0281(13) Uani 1 1 d . . . H13A H 0.4788 -0.1483 0.0048 0.034 Uiso 1 1 calc R . . H13B H 0.5574 -0.0770 0.1034 0.034 Uiso 1 1 calc R . . C14 C 0.7601(6) 0.0421(5) 0.0518(4) 0.0246(12) Uani 1 1 d . . . C15 C 0.6485(6) -0.0611(6) -0.0907(4) 0.0305(14) Uani 1 1 d . . . H15 H 0.5850 -0.1173 -0.1374 0.037 Uiso 1 1 calc R . . C16 C 0.7512(6) 0.0276(6) -0.1007(4) 0.0326(14) Uani 1 1 d . . . H16 H 0.7715 0.0444 -0.1557 0.039 Uiso 1 1 calc R . . C17 C 0.9284(6) 0.1984(6) 0.0045(5) 0.0393(17) Uani 1 1 d . . . H17A H 0.9857 0.1841 -0.0396 0.047 Uiso 1 1 calc R . . H17B H 0.9792 0.2102 0.0656 0.047 Uiso 1 1 calc R . . C18 C 0.8802(7) 0.3156(6) -0.0022(5) 0.0456(19) Uani 1 1 d . . . H18A H 0.9540 0.3858 0.0076 0.068 Uiso 1 1 calc R . . H18B H 0.8274 0.3326 0.0437 0.068 Uiso 1 1 calc R . . H18C H 0.8284 0.3035 -0.0623 0.068 Uiso 1 1 calc R . . C19 C 0.1351(7) -0.2387(8) 0.3556(5) 0.051(2) Uani 1 1 d . . . H19 H 0.1882 -0.1573 0.3739 0.061 Uiso 1 1 calc R . . C20 C 0.1120(6) -0.2987(7) 0.2618(5) 0.0384(16) Uani 1 1 d . . . H20 H 0.1532 -0.2571 0.2222 0.046 Uiso 1 1 calc R . . C21 C 0.0239(7) -0.4268(7) 0.2231(5) 0.0477(19) Uani 1 1 d . . . H21A H -0.0151 -0.4322 0.1598 0.057 Uiso 1 1 calc R . . H21B H -0.0468 -0.4369 0.2576 0.057 Uiso 1 1 calc R . . C22 C 0.0941(8) -0.5355(8) 0.2253(6) 0.059(2) Uani 1 1 d . . . H22A H 0.1168 -0.5631 0.1656 0.071 Uiso 1 1 calc R . . H22B H 0.0349 -0.6065 0.2373 0.071 Uiso 1 1 calc R . . C23 C 0.2216(7) -0.4957(8) 0.3007(5) 0.048(2) Uani 1 1 d . . . H23 H 0.2997 -0.5049 0.2812 0.057 Uiso 1 1 calc R . . C24 C 0.2291(8) -0.4481(7) 0.3937(5) 0.050(2) Uani 1 1 d . . . H24 H 0.3089 -0.4348 0.4334 0.060 Uiso 1 1 calc R . . C25 C 0.1105(10) -0.4164(8) 0.4337(7) 0.075(3) Uani 1 1 d . . . H25A H 0.0334 -0.4822 0.4026 0.090 Uiso 1 1 calc R . . H25B H 0.1247 -0.4189 0.4982 0.090 Uiso 1 1 calc R . . C26 C 0.0826(8) -0.2938(10) 0.4267(5) 0.071(3) Uani 1 1 d . . . H26A H -0.0119 -0.3033 0.4153 0.085 Uiso 1 1 calc R . . H26B H 0.1175 -0.2344 0.4857 0.085 Uiso 1 1 calc R . . C27 C 0.8839(6) -0.0582(6) 0.2076(5) 0.0377(16) Uani 1 1 d . . . H27 H 0.8223 -0.1052 0.1561 0.045 Uiso 1 1 calc R . . C28 C 0.9832(6) 0.0398(6) 0.1975(4) 0.0325(14) Uani 1 1 d . . . H28 H 0.9838 0.0558 0.1393 0.039 Uiso 1 1 calc R . . C29 C 1.0889(7) 0.1203(7) 0.2762(5) 0.0418(17) Uani 1 1 d . . . H29A H 1.1456 0.0678 0.2963 0.050 Uiso 1 1 calc R . . H29B H 1.1420 0.1856 0.2540 0.050 Uiso 1 1 calc R . . C30 C 1.0380(7) 0.1820(8) 0.3569(5) 0.0428(17) Uani 1 1 d . . . H30A H 1.0956 0.2646 0.3843 0.051 Uiso 1 1 calc R . . H30B H 1.0415 0.1316 0.4026 0.051 Uiso 1 1 calc R . . C31 C 0.8985(6) 0.1983(6) 0.3339(4) 0.0322(14) Uani 1 1 d . . . H31 H 0.8869 0.2734 0.3187 0.039 Uiso 1 1 calc R . . C32 C 0.7873(7) 0.1084(6) 0.3340(4) 0.0383(16) Uani 1 1 d . . . H32 H 0.7068 0.1304 0.3226 0.046 Uiso 1 1 calc R . . C33 C 0.7848(8) -0.0216(8) 0.3510(6) 0.054(2) Uani 1 1 d . . . H33A H 0.6956 -0.0722 0.3319 0.065 Uiso 1 1 calc R . . H33B H 0.8107 -0.0140 0.4165 0.065 Uiso 1 1 calc R . . C34 C 0.8743(7) -0.0896(7) 0.3005(5) 0.048(2) Uani 1 1 d . . . H34A H 0.8419 -0.1802 0.2912 0.058 Uiso 1 1 calc R . . H34B H 0.9615 -0.0668 0.3383 0.058 Uiso 1 1 calc R . . N1 N 0.5493(5) -0.4221(5) 0.2957(3) 0.0284(11) Uani 1 1 d . . . N2 N 0.5783(5) -0.2999(5) 0.4305(4) 0.0349(13) Uani 1 1 d . . . N3 N 0.6580(5) -0.0503(4) 0.0037(3) 0.0240(10) Uani 1 1 d . . . N4 N 0.8188(5) 0.0870(5) -0.0136(3) 0.0288(11) Uani 1 1 d . . . Cl1 Cl 0.40231(18) -0.10830(17) 0.30249(13) 0.0448(4) Uani 1 1 d . . . Cl2 Cl 0.67531(15) 0.25137(15) 0.18647(11) 0.0343(4) Uani 1 1 d . . . Ir1 Ir 0.30831(2) -0.30849(2) 0.325679(16) 0.02841(8) Uani 1 1 d . . . Ir2 Ir 0.80860(2) 0.10326(2) 0.192009(15) 0.02551(8) Uani 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 C1 0.028(3) 0.031(3) 0.020(3) 0.007(3) 0.005(2) 0.003(3) C2 0.033(4) 0.060(5) 0.036(4) 0.020(4) 0.014(3) 0.019(3) C3 0.033(4) 0.057(5) 0.039(4) 0.015(4) 0.004(3) 0.011(4) C4 0.060(5) 0.048(5) 0.033(4) 0.004(4) -0.001(3) 0.022(4) C5 0.061(5) 0.089(7) 0.039(4) 0.012(5) 0.016(4) 0.011(5) C6 0.030(3) 0.038(4) 0.031(3) 0.009(3) 0.011(3) 0.013(3) C7 0.033(3) 0.030(3) 0.027(3) 0.000(3) 0.001(3) 0.006(3) C8 0.022(3) 0.027(3) 0.032(3) 0.009(3) 0.009(3) 0.007(2) C9 0.035(4) 0.031(3) 0.034(3) 0.007(3) 0.016(3) 0.014(3) C10 0.027(3) 0.026(3) 0.034(3) 0.007(3) 0.012(3) 0.006(3) C11 0.018(3) 0.027(3) 0.028(3) 0.007(3) 0.006(2) 0.006(2) C12 0.026(3) 0.032(3) 0.025(3) 0.005(3) 0.005(2) 0.009(3) C13 0.022(3) 0.026(3) 0.042(4) 0.011(3) 0.012(3) 0.010(2) C14 0.030(3) 0.024(3) 0.023(3) 0.005(3) 0.005(2) 0.012(3) C15 0.030(3) 0.036(4) 0.018(3) -0.005(3) -0.001(2) 0.006(3) C16 0.040(4) 0.030(3) 0.030(3) 0.005(3) 0.011(3) 0.012(3) C17 0.032(4) 0.035(4) 0.046(4) 0.003(3) 0.018(3) -0.004(3) C18 0.057(5) 0.032(4) 0.054(5) 0.016(4) 0.025(4) 0.007(3) C19 0.029(4) 0.071(6) 0.051(5) -0.001(4) 0.007(3) 0.024(4) C20 0.023(3) 0.056(5) 0.038(4) 0.009(4) 0.006(3) 0.016(3) C21 0.037(4) 0.055(5) 0.042(4) 0.001(4) -0.001(3) 0.005(4) C22 0.047(5) 0.053(5) 0.068(6) 0.003(4) 0.009(4) 0.004(4) C23 0.044(4) 0.086(6) 0.041(4) 0.038(4) 0.035(3) 0.039(4) C24 0.056(5) 0.045(5) 0.052(5) 0.020(4) 0.026(4) -0.002(4) C25 0.100(8) 0.048(5) 0.086(7) 0.012(5) 0.065(6) 0.009(5) C26 0.042(5) 0.142(10) 0.033(4) 0.009(5) 0.018(4) 0.035(5) C27 0.025(3) 0.035(4) 0.054(4) 0.008(3) 0.000(3) 0.017(3) C28 0.031(3) 0.038(4) 0.032(3) 0.005(3) 0.002(3) 0.020(3) C29 0.026(3) 0.039(4) 0.050(4) -0.008(3) -0.002(3) 0.009(3) C30 0.035(4) 0.053(5) 0.036(4) 0.005(4) 0.000(3) 0.010(3) C31 0.038(4) 0.039(4) 0.020(3) 0.003(3) 0.002(3) 0.014(3) C32 0.044(4) 0.045(4) 0.034(4) 0.012(3) 0.017(3) 0.018(3) C33 0.052(5) 0.065(6) 0.058(5) 0.031(5) 0.022(4) 0.019(4) C34 0.042(4) 0.044(4) 0.067(5) 0.031(4) 0.001(4) 0.017(4) N1 0.029(3) 0.037(3) 0.026(3) 0.014(2) 0.010(2) 0.015(2) N2 0.034(3) 0.044(3) 0.026(3) 0.008(3) 0.002(2) 0.008(3) N3 0.025(3) 0.023(3) 0.024(2) 0.004(2) 0.003(2) 0.008(2) N4 0.027(3) 0.030(3) 0.032(3) 0.008(2) 0.009(2) 0.009(2) Cl1 0.0467(10) 0.0365(9) 0.0548(11) 0.0185(9) 0.0070(8) 0.0114(8) Cl2 0.0358(9) 0.0345(9) 0.0375(8) 0.0096(7) 0.0092(7) 0.0170(7) Ir1 0.02575(14) 0.03418(15) 0.02782(14) 0.00779(11) 0.00773(10) 0.01024(11) Ir2 0.02424(13) 0.02763(14) 0.02548(13) 0.00455(10) 0.00509(10) 0.00926(10) _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 C1 N2 1.355(8) . ? C1 N1 1.367(8) . ? C1 Ir1 2.035(6) . ? C2 C3 1.322(10) . ? C2 N1 1.355(8) . ? C2 H2 0.9300 . ? C3 N2 1.388(9) . ? C3 H3 0.9300 . ? C4 N2 1.453(9) . ? C4 C5 1.513(9) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 N1 1.487(8) . ? C6 C7 1.505(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C12 1.363(9) . ? C7 C8 1.417(9) . ? C8 C9 1.402(7) . ? C8 H8 0.9300 . ? C9 C10 1.385(8) . ? C9 H9 0.9300 . ? C10 C11 1.389(8) . ? C10 H10 0.9300 . ? C11 C12 1.405(7) . ? C11 C13 1.499(8) . ? C12 H12 0.9300 . ? C13 N3 1.459(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N3 1.340(7) . ? C14 N4 1.362(7) . ? C14 Ir2 2.045(6) . ? C15 C16 1.363(8) . ? C15 N3 1.392(7) . ? C15 H15 0.9300 . ? C16 N4 1.370(8) . ? C16 H16 0.9300 . ? C17 N4 1.471(7) . ? C17 C18 1.496(10) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.403(10) . ? C19 C26 1.459(10) . ? C19 Ir1 2.184(7) . ? C19 H19 0.9300 . ? C20 C21 1.492(9) . ? C20 Ir1 2.191(6) . ? C20 H20 0.9300 . ? C21 C22 1.533(12) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.562(11) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.381(10) . ? C23 Ir1 2.034(8) . ? C23 H23 0.9300 . ? C24 C25 1.532(11) . ? C24 Ir1 2.126(6) . ? C24 H24 0.9300 . ? C25 C26 1.463(13) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.405(8) . ? C27 C34 1.521(9) . ? C27 Ir2 2.130(6) . ? C27 H27 0.9300 . ? C28 C29 1.506(9) . ? C28 Ir2 2.091(6) . ? C28 H28 0.9300 . ? C29 C30 1.493(10) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.518(9) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.386(8) . ? C31 Ir2 2.176(6) . ? C31 H31 0.9300 . ? C32 C33 1.507(10) . ? C32 Ir2 2.176(6) . ? C32 H32 0.9300 . ? C33 C34 1.511(10) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? Cl1 Ir1 2.3622(16) . ? Cl2 Ir2 2.3613(16) . ? 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 C1 N1 104.4(5) . . ? N2 C1 Ir1 125.8(5) . . ? N1 C1 Ir1 129.8(4) . . ? C3 C2 N1 107.2(6) . . ? C3 C2 H2 126.4 . . ? N1 C2 H2 126.4 . . ? C2 C3 N2 108.0(6) . . ? C2 C3 H3 126.0 . . ? N2 C3 H3 126.0 . . ? N2 C4 C5 113.4(6) . . ? N2 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? N2 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C7 111.2(5) . . ? N1 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? N1 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C12 C7 C8 119.2(5) . . ? C12 C7 C6 121.6(6) . . ? C8 C7 C6 119.2(6) . . ? C9 C8 C7 119.0(6) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C10 C9 C8 120.5(6) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 120.7(5) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C12 118.2(5) . . ? C10 C11 C13 123.8(5) . . ? C12 C11 C13 117.8(5) . . ? C7 C12 C11 122.3(6) . . ? C7 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? N3 C13 C11 113.6(5) . . ? N3 C13 H13A 108.8 . . ? C11 C13 H13A 108.8 . . ? N3 C13 H13B 108.8 . . ? C11 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? N3 C14 N4 104.3(5) . . ? N3 C14 Ir2 126.7(4) . . ? N4 C14 Ir2 129.0(4) . . ? C16 C15 N3 106.0(5) . . ? C16 C15 H15 127.0 . . ? N3 C15 H15 127.0 . . ? C15 C16 N4 106.4(5) . . ? C15 C16 H16 126.8 . . ? N4 C16 H16 126.8 . . ? N4 C17 C18 111.5(5) . . ? N4 C17 H17A 109.3 . . ? C18 C17 H17A 109.3 . . ? N4 C17 H17B 109.3 . . ? C18 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C26 125.2(8) . . ? C20 C19 Ir1 71.6(4) . . ? C26 C19 Ir1 110.0(5) . . ? C20 C19 H19 117.4 . . ? C26 C19 H19 117.4 . . ? Ir1 C19 H19 88.3 . . ? C19 C20 C21 122.6(6) . . ? C19 C20 Ir1 71.0(4) . . ? C21 C20 Ir1 112.3(5) . . ? C19 C20 H20 118.7 . . ? C21 C20 H20 118.7 . . ? Ir1 C20 H20 86.8 . . ? C20 C21 C22 113.6(6) . . ? C20 C21 H21A 108.8 . . ? C22 C21 H21A 108.8 . . ? C20 C21 H21B 108.8 . . ? C22 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C21 C22 C23 112.1(7) . . ? C21 C22 H22A 109.2 . . ? C23 C22 H22A 109.2 . . ? C21 C22 H22B 109.2 . . ? C23 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? C24 C23 C22 126.1(6) . . ? C24 C23 Ir1 74.2(5) . . ? C22 C23 Ir1 113.0(5) . . ? C24 C23 H23 117.0 . . ? C22 C23 H23 117.0 . . ? Ir1 C23 H23 82.5 . . ? C23 C24 C25 122.3(8) . . ? C23 C24 Ir1 67.0(4) . . ? C25 C24 Ir1 111.1(5) . . ? C23 C24 H24 118.9 . . ? C25 C24 H24 118.9 . . ? Ir1 C24 H24 91.7 . . ? C26 C25 C24 115.8(6) . . ? C26 C25 H25A 108.3 . . ? C24 C25 H25A 108.3 . . ? C26 C25 H25B 108.3 . . ? C24 C25 H25B 108.3 . . ? H25A C25 H25B 107.4 . . ? C19 C26 C25 116.0(7) . . ? C19 C26 H26A 108.3 . . ? C25 C26 H26A 108.3 . . ? C19 C26 H26B 108.3 . . ? C25 C26 H26B 108.3 . . ? H26A C26 H26B 107.4 . . ? C28 C27 C34 121.9(6) . . ? C28 C27 Ir2 69.1(3) . . ? C34 C27 Ir2 112.7(5) . . ? C28 C27 H27 119.1 . . ? C34 C27 H27 119.1 . . ? Ir2 C27 H27 88.3 . . ? C27 C28 C29 123.3(6) . . ? C27 C28 Ir2 72.1(4) . . ? C29 C28 Ir2 112.3(5) . . ? C27 C28 H28 118.4 . . ? C29 C28 H28 118.4 . . ? Ir2 C28 H28 85.7 . . ? C30 C29 C28 114.2(6) . . ? C30 C29 H29A 108.7 . . ? C28 C29 H29A 108.7 . . ? C30 C29 H29B 108.7 . . ? C28 C29 H29B 108.7 . . ? H29A C29 H29B 107.6 . . ? C29 C30 C31 114.2(6) . . ? C29 C30 H30A 108.7 . . ? C31 C30 H30A 108.7 . . ? C29 C30 H30B 108.7 . . ? C31 C30 H30B 108.7 . . ? H30A C30 H30B 107.6 . . ? C32 C31 C30 124.2(6) . . ? C32 C31 Ir2 71.4(4) . . ? C30 C31 Ir2 111.4(4) . . ? C32 C31 H31 117.9 . . ? C30 C31 H31 117.9 . . ? Ir2 C31 H31 87.2 . . ? C31 C32 C33 126.0(6) . . ? C31 C32 Ir2 71.4(3) . . ? C33 C32 Ir2 108.5(5) . . ? C31 C32 H32 117.0 . . ? C33 C32 H32 117.0 . . ? Ir2 C32 H32 90.1 . . ? C32 C33 C34 113.3(5) . . ? C32 C33 H33A 108.9 . . ? C34 C33 H33A 108.9 . . ? C32 C33 H33B 108.9 . . ? C34 C33 H33B 108.9 . . ? H33A C33 H33B 107.7 . . ? C33 C34 C27 112.8(5) . . ? C33 C34 H34A 109.0 . . ? C27 C34 H34A 109.0 . . ? C33 C34 H34B 109.0 . . ? C27 C34 H34B 109.0 . . ? H34A C34 H34B 107.8 . . ? C2 N1 C1 111.1(5) . . ? C2 N1 C6 123.6(5) . . ? C1 N1 C6 125.1(5) . . ? C1 N2 C3 109.4(6) . . ? C1 N2 C4 125.4(6) . . ? C3 N2 C4 125.2(6) . . ? C14 N3 C15 111.6(4) . . ? C14 N3 C13 124.6(5) . . ? C15 N3 C13 123.8(5) . . ? C14 N4 C16 111.7(5) . . ? C14 N4 C17 125.2(5) . . ? C16 N4 C17 122.4(5) . . ? C23 Ir1 C1 91.2(3) . . ? C23 Ir1 C24 38.7(3) . . ? C1 Ir1 C24 91.5(3) . . ? C23 Ir1 C19 96.2(3) . . ? C1 Ir1 C19 158.0(3) . . ? C24 Ir1 C19 81.6(3) . . ? C23 Ir1 C20 82.2(3) . . ? C1 Ir1 C20 164.6(3) . . ? C24 Ir1 C20 91.9(3) . . ? C19 Ir1 C20 37.4(3) . . ? C23 Ir1 Cl1 161.44(18) . . ? C1 Ir1 Cl1 90.26(16) . . ? C24 Ir1 Cl1 159.7(2) . . ? C19 Ir1 Cl1 89.2(2) . . ? C20 Ir1 Cl1 91.70(19) . . ? C14 Ir2 C28 92.8(2) . . ? C14 Ir2 C27 93.2(2) . . ? C28 Ir2 C27 38.9(2) . . ? C14 Ir2 C32 156.4(2) . . ? C28 Ir2 C32 97.3(3) . . ? C27 Ir2 C32 81.7(3) . . ? C14 Ir2 C31 166.5(2) . . ? C28 Ir2 C31 81.6(2) . . ? C27 Ir2 C31 90.1(3) . . ? C32 Ir2 C31 37.1(2) . . ? C14 Ir2 Cl2 89.70(17) . . ? C28 Ir2 Cl2 156.21(19) . . ? C27 Ir2 Cl2 164.49(17) . . ? C32 Ir2 Cl2 89.62(19) . . ? C31 Ir2 Cl2 90.62(18) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 3.502 _refine_diff_density_min -2.406 _refine_diff_density_rms 0.201 # Attachment 'Thione_6.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 719957' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 N4 S2' _chemical_formula_sum 'C18 H22 N4 S2' _chemical_formula_weight 358.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 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 14.1399(3) _cell_length_b 9.5935(3) _cell_length_c 28.2325(8) _cell_angle_alpha 90.00 _cell_angle_beta 103.675(2) _cell_angle_gamma 90.00 _cell_volume 3721.21(18) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8345 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 29.131 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.293 _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 173(2) _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 13019 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0509 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 27.00 _reflns_number_total 8071 _reflns_number_gt 5472 _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^)+(0.0853P)^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 8071 _refine_ls_number_parameters 437 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0805 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1499 _refine_ls_wR_factor_gt 0.1307 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1A S 0.07367(4) 0.18309(6) 0.66687(2) 0.03725(17) Uani 1 1 d . . . S2A S 0.63325(5) 0.24253(9) 0.95088(2) 0.0570(2) Uani 1 1 d . . . C1A C 0.16947(14) 0.2237(2) 0.64304(8) 0.0284(5) Uani 1 1 d . . . C2A C 0.32099(15) 0.2399(3) 0.63130(8) 0.0382(6) Uani 1 1 d . . . H2A H 0.3879 0.2295 0.6358 0.046 Uiso 1 1 calc R . . C3A C 0.26131(15) 0.3087(3) 0.59500(8) 0.0407(6) Uani 1 1 d . . . H3 H 0.2793 0.3546 0.5695 0.049 Uiso 1 1 calc R . . C4A C 0.08163(15) 0.3634(3) 0.57074(8) 0.0401(6) Uani 1 1 d . . . H4A1 H 0.0267 0.3507 0.5854 0.048 Uiso 1 1 calc R . . H4A2 H 0.0667 0.3168 0.5394 0.048 Uiso 1 1 calc R . . C5A C 0.09574(18) 0.5166(3) 0.56322(9) 0.0516(7) Uani 1 1 d . . . H5A1 H 0.1177 0.5614 0.5943 0.077 Uiso 1 1 calc R . . H5A2 H 0.0351 0.5571 0.5462 0.077 Uiso 1 1 calc R . . H5A3 H 0.1434 0.5290 0.5444 0.077 Uiso 1 1 calc R . . C6A C 0.30120(15) 0.1081(2) 0.70566(8) 0.0346(5) Uani 1 1 d . . . H6A1 H 0.3343 0.0256 0.6980 0.042 Uiso 1 1 calc R . . H6A2 H 0.2469 0.0776 0.7186 0.042 Uiso 1 1 calc R . . C7A C 0.37060(13) 0.1911(2) 0.74413(7) 0.0271(5) Uani 1 1 d . . . C8A C 0.35483(14) 0.3316(2) 0.75145(7) 0.0290(5) Uani 1 1 d . . . H8A H 0.3013 0.3768 0.7320 0.035 Uiso 1 1 calc R . . C9A C 0.41883(14) 0.4044(2) 0.78775(8) 0.0309(5) Uani 1 1 d . . . H9A H 0.4081 0.4984 0.7927 0.037 Uiso 1 1 calc R . . C10A C 0.49860(14) 0.3378(2) 0.81669(8) 0.0310(5) Uani 1 1 d . . . H10A H 0.5416 0.3874 0.8408 0.037 Uiso 1 1 calc R . . C11A C 0.51491(14) 0.1967(2) 0.80996(7) 0.0273(5) Uani 1 1 d . . . C12A C 0.45022(13) 0.1249(2) 0.77333(7) 0.0275(5) Uani 1 1 d . . . H12A H 0.4607 0.0308 0.7684 0.033 Uiso 1 1 calc R . . C13A C 0.59938(14) 0.1196(2) 0.84248(8) 0.0353(5) Uani 1 1 d . . . H13A H 0.5770 0.0750 0.8687 0.042 Uiso 1 1 calc R . . H13B H 0.6211 0.0469 0.8236 0.042 Uiso 1 1 calc R . . C14A C 0.69637(14) 0.2699(2) 0.90835(8) 0.0314(5) Uani 1 1 d . . . C15A C 0.74774(15) 0.2607(2) 0.83918(8) 0.0330(5) Uani 1 1 d . . . H15A H 0.7521 0.2367 0.8079 0.040 Uiso 1 1 calc R . . C16A C 0.80481(15) 0.3511(2) 0.86891(8) 0.0343(5) Uani 1 1 d . . . H16A H 0.8567 0.4006 0.8622 0.041 Uiso 1 1 calc R . . C17A C 0.81584(16) 0.4444(3) 0.95361(8) 0.0429(6) Uani 1 1 d . . . H17A H 0.7648 0.4761 0.9687 0.051 Uiso 1 1 calc R . . H17B H 0.8454 0.5259 0.9427 0.051 Uiso 1 1 calc R . . C18A C 0.89195(16) 0.3673(3) 0.99103(9) 0.0480(6) Uani 1 1 d . . . H18A H 0.8631 0.2866 1.0020 0.072 Uiso 1 1 calc R . . H18B H 0.9171 0.4275 1.0182 0.072 Uiso 1 1 calc R . . H18C H 0.9440 0.3388 0.9766 0.072 Uiso 1 1 calc R . . N1A N 0.26386(11) 0.18697(19) 0.66103(6) 0.0307(4) Uani 1 1 d . . . N2A N 0.16835(12) 0.2994(2) 0.60218(7) 0.0332(4) Uani 1 1 d . . . N3A N 0.68132(12) 0.20946(19) 0.86342(6) 0.0303(4) Uani 1 1 d . . . N4A N 0.77262(11) 0.3574(2) 0.91117(6) 0.0318(4) Uani 1 1 d . . . S1B S -0.16246(5) 0.76056(8) 0.54005(2) 0.04678(19) Uani 1 1 d . . . S2B S 0.40607(4) 0.78002(7) 0.82503(2) 0.03958(17) Uani 1 1 d . . . C1B C -0.19727(15) 0.7375(2) 0.59264(8) 0.0295(5) Uani 1 1 d . . . C2B C -0.19927(16) 0.7344(3) 0.67194(8) 0.0388(6) Uani 1 1 d . . . H2B H -0.1797 0.7444 0.7056 0.047 Uiso 1 1 calc R . . C3B C -0.28500(16) 0.6879(3) 0.64688(8) 0.0400(6) Uani 1 1 d . . . H3B H -0.3364 0.6593 0.6599 0.048 Uiso 1 1 calc R . . C4B C -0.36369(15) 0.6427(3) 0.55840(9) 0.0444(6) Uani 1 1 d . . . H4B1 H -0.3547 0.6803 0.5279 0.053 Uiso 1 1 calc R . . H4B2 H -0.4249 0.6780 0.5634 0.053 Uiso 1 1 calc R . . C5B C -0.3681(3) 0.4880(3) 0.55524(12) 0.0874(11) Uani 1 1 d . . . H5B1 H -0.3095 0.4532 0.5479 0.131 Uiso 1 1 calc R . . H5B2 H -0.4231 0.4606 0.5299 0.131 Uiso 1 1 calc R . . H5B3 H -0.3746 0.4503 0.5858 0.131 Uiso 1 1 calc R . . C6B C -0.04697(15) 0.8253(3) 0.65042(8) 0.0421(6) Uani 1 1 d . . . H6B1 H -0.0507 0.9218 0.6601 0.051 Uiso 1 1 calc R . . H6B2 H -0.0208 0.8237 0.6216 0.051 Uiso 1 1 calc R . . C7B C 0.02028(15) 0.7469(2) 0.69084(8) 0.0315(5) Uani 1 1 d . . . C8B C 0.03549(15) 0.6051(2) 0.68680(8) 0.0352(5) Uani 1 1 d . . . H8B H 0.0026 0.5574 0.6591 0.042 Uiso 1 1 calc R . . C9B C 0.09888(15) 0.5341(2) 0.72346(8) 0.0360(5) Uani 1 1 d . . . H9B H 0.1096 0.4394 0.7200 0.043 Uiso 1 1 calc R . . C10B C 0.14692(14) 0.6035(2) 0.76561(8) 0.0330(5) Uani 1 1 d . . . H10B H 0.1893 0.5551 0.7903 0.040 Uiso 1 1 calc R . . C11B C 0.13138(14) 0.7455(2) 0.77072(8) 0.0300(5) Uani 1 1 d . . . C12B C 0.06816(13) 0.8157(2) 0.73273(8) 0.0302(5) Uani 1 1 d . . . H12B H 0.0580 0.9108 0.7357 0.036 Uiso 1 1 calc R . . C13B C 0.17904(15) 0.8256(3) 0.81604(8) 0.0385(6) Uani 1 1 d . . . H13C H 0.2200 0.8977 0.8073 0.046 Uiso 1 1 calc R . . H13D H 0.1289 0.8713 0.8286 0.046 Uiso 1 1 calc R . . C14B C 0.33358(14) 0.7128(2) 0.85868(8) 0.0300(5) Uani 1 1 d . . . C15B C 0.20172(16) 0.6642(3) 0.88775(8) 0.0442(6) Uani 1 1 d . . . H15B H 0.1382 0.6643 0.8916 0.053 Uiso 1 1 calc R . . C16B C 0.27603(16) 0.5907(3) 0.91355(8) 0.0429(6) Uani 1 1 d . . . H16B H 0.2738 0.5303 0.9390 0.051 Uiso 1 1 calc R . . C17B C 0.45412(15) 0.5613(3) 0.91470(8) 0.0417(6) Uani 1 1 d . . . H17C H 0.4872 0.5550 0.8883 0.050 Uiso 1 1 calc R . . H17D H 0.4480 0.4676 0.9265 0.050 Uiso 1 1 calc R . . C18B C 0.51495(16) 0.6473(3) 0.95535(8) 0.0462(6) Uani 1 1 d . . . H18D H 0.5225 0.7396 0.9437 0.069 Uiso 1 1 calc R . . H18E H 0.5778 0.6049 0.9664 0.069 Uiso 1 1 calc R . . H18F H 0.4833 0.6521 0.9819 0.069 Uiso 1 1 calc R . . N1B N -0.14449(12) 0.76508(19) 0.63866(6) 0.0313(4) Uani 1 1 d . . . N2B N -0.28436(11) 0.6896(2) 0.59819(7) 0.0322(4) Uani 1 1 d . . . N3B N 0.23731(12) 0.74044(19) 0.85403(7) 0.0331(4) Uani 1 1 d . . . N4B N 0.35698(12) 0.61954(19) 0.89590(6) 0.0338(4) Uani 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 S1A 0.0287(3) 0.0349(3) 0.0504(4) -0.0010(3) 0.0138(2) -0.0035(2) S2A 0.0396(4) 0.1004(7) 0.0350(4) -0.0036(4) 0.0169(3) -0.0082(3) C1A 0.0241(10) 0.0272(12) 0.0312(12) -0.0086(9) 0.0010(8) -0.0036(8) C2A 0.0223(10) 0.0554(16) 0.0365(13) -0.0067(11) 0.0060(9) -0.0036(10) C3A 0.0342(12) 0.0590(17) 0.0301(12) -0.0031(12) 0.0100(10) -0.0110(11) C4A 0.0324(11) 0.0419(15) 0.0384(13) 0.0017(11) -0.0070(10) -0.0008(10) C5A 0.0541(15) 0.0452(17) 0.0498(16) 0.0038(13) 0.0008(12) 0.0021(12) C6A 0.0306(11) 0.0317(13) 0.0366(12) -0.0016(10) -0.0020(9) -0.0001(9) C7A 0.0243(10) 0.0305(12) 0.0265(11) -0.0009(9) 0.0061(8) -0.0026(9) C8A 0.0261(10) 0.0328(12) 0.0273(11) 0.0026(10) 0.0046(8) 0.0037(9) C9A 0.0325(11) 0.0265(12) 0.0337(12) -0.0023(10) 0.0078(9) 0.0022(9) C10A 0.0287(10) 0.0313(12) 0.0303(11) -0.0056(10) 0.0016(9) -0.0033(9) C11A 0.0259(10) 0.0302(12) 0.0261(11) 0.0010(9) 0.0070(8) 0.0019(9) C12A 0.0269(10) 0.0270(11) 0.0293(11) -0.0011(9) 0.0081(8) 0.0001(9) C13A 0.0322(11) 0.0349(13) 0.0346(12) -0.0005(10) -0.0006(9) 0.0014(10) C14A 0.0247(10) 0.0413(14) 0.0268(11) -0.0008(10) 0.0030(8) 0.0067(9) C15A 0.0327(11) 0.0399(14) 0.0276(12) 0.0041(10) 0.0091(9) 0.0107(10) C16A 0.0282(10) 0.0371(13) 0.0386(13) 0.0092(11) 0.0099(9) 0.0061(9) C17A 0.0409(12) 0.0398(15) 0.0434(14) -0.0103(12) 0.0008(10) 0.0037(11) C18A 0.0427(13) 0.0503(17) 0.0436(14) -0.0094(13) -0.0044(11) 0.0014(12) N1A 0.0251(8) 0.0352(11) 0.0296(10) -0.0052(8) 0.0023(7) -0.0005(8) N2A 0.0261(9) 0.0403(12) 0.0304(10) -0.0026(9) 0.0012(7) -0.0050(8) N3A 0.0247(8) 0.0392(11) 0.0258(10) 0.0004(8) 0.0036(7) 0.0050(8) N4A 0.0267(9) 0.0351(11) 0.0307(10) -0.0005(8) 0.0010(7) 0.0040(8) S1B 0.0479(4) 0.0651(5) 0.0285(3) 0.0071(3) 0.0115(3) -0.0080(3) S2B 0.0361(3) 0.0408(4) 0.0440(4) 0.0037(3) 0.0137(3) -0.0045(3) C1B 0.0273(10) 0.0308(12) 0.0294(12) 0.0048(10) 0.0047(9) 0.0027(9) C2B 0.0376(12) 0.0544(16) 0.0264(12) -0.0030(11) 0.0114(10) -0.0046(11) C3B 0.0310(11) 0.0540(16) 0.0387(13) 0.0007(12) 0.0152(10) -0.0027(11) C4B 0.0319(11) 0.0515(17) 0.0430(14) 0.0067(13) -0.0045(10) -0.0061(11) C5B 0.113(3) 0.047(2) 0.073(2) -0.0116(17) -0.0365(19) -0.0100(18) C6B 0.0332(11) 0.0512(16) 0.0371(13) 0.0094(12) -0.0015(10) -0.0160(11) C7B 0.0261(10) 0.0400(14) 0.0278(11) 0.0030(10) 0.0055(9) -0.0082(9) C8B 0.0332(11) 0.0419(14) 0.0301(12) -0.0068(10) 0.0066(9) -0.0123(10) C9B 0.0344(11) 0.0309(13) 0.0434(13) -0.0071(11) 0.0107(10) -0.0022(10) C10B 0.0302(11) 0.0339(13) 0.0334(12) -0.0015(10) 0.0046(9) 0.0022(9) C11B 0.0236(10) 0.0342(13) 0.0322(12) -0.0033(10) 0.0067(9) -0.0014(9) C12B 0.0235(10) 0.0306(12) 0.0356(12) 0.0000(10) 0.0050(9) -0.0008(9) C13B 0.0332(11) 0.0402(14) 0.0367(13) -0.0094(11) -0.0029(10) 0.0062(10) C14B 0.0300(11) 0.0296(12) 0.0282(12) -0.0038(9) 0.0023(9) -0.0025(9) C15B 0.0351(12) 0.0670(18) 0.0316(13) -0.0072(13) 0.0099(10) -0.0145(12) C16B 0.0493(14) 0.0507(16) 0.0286(12) -0.0005(11) 0.0089(10) -0.0174(12) C17B 0.0443(13) 0.0358(14) 0.0385(13) 0.0008(11) -0.0033(10) 0.0088(11) C18B 0.0377(12) 0.0601(18) 0.0360(13) -0.0062(13) -0.0010(10) 0.0097(12) N1B 0.0267(9) 0.0399(11) 0.0257(9) 0.0016(8) 0.0030(7) -0.0057(8) N2B 0.0224(8) 0.0394(11) 0.0328(10) 0.0019(9) 0.0028(7) -0.0008(8) N3B 0.0256(9) 0.0432(12) 0.0283(10) -0.0038(9) 0.0015(7) 0.0000(8) N4B 0.0344(9) 0.0334(11) 0.0299(10) 0.0009(8) 0.0002(8) -0.0022(8) _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 S1A C1A 1.694(2) . ? S2A C14A 1.678(2) . ? C1A N1A 1.357(2) . ? C1A N2A 1.360(3) . ? C2A C3A 1.338(3) . ? C2A N1A 1.391(3) . ? C3A N2A 1.379(3) . ? C4A N2A 1.468(3) . ? C4A C5A 1.505(3) . ? C6A N1A 1.458(3) . ? C6A C7A 1.507(3) . ? C7A C12A 1.382(3) . ? C7A C8A 1.390(3) . ? C8A C9A 1.385(3) . ? C9A C10A 1.383(3) . ? C10A C11A 1.393(3) . ? C11A C12A 1.391(3) . ? C11A C13A 1.516(3) . ? C13A N3A 1.453(3) . ? C14A N4A 1.354(3) . ? C14A N3A 1.365(3) . ? C15A C16A 1.337(3) . ? C15A N3A 1.377(3) . ? C16A N4A 1.375(3) . ? C17A N4A 1.469(3) . ? C17A C18A 1.511(3) . ? S1B C1B 1.686(2) . ? S2B C14B 1.682(2) . ? C1B N2B 1.358(3) . ? C1B N1B 1.363(3) . ? C2B C3B 1.328(3) . ? C2B N1B 1.383(3) . ? C3B N2B 1.377(3) . ? C4B N2B 1.458(3) . ? C4B C5B 1.487(4) . ? C6B N1B 1.459(3) . ? C6B C7B 1.503(3) . ? C7B C12B 1.384(3) . ? C7B C8B 1.387(3) . ? C8B C9B 1.378(3) . ? C9B C10B 1.392(3) . ? C10B C11B 1.393(3) . ? C11B C12B 1.396(3) . ? C11B C13B 1.508(3) . ? C13B N3B 1.442(3) . ? C14B N4B 1.360(3) . ? C14B N3B 1.362(3) . ? C15B C16B 1.330(3) . ? C15B N3B 1.386(3) . ? C16B N4B 1.380(3) . ? C17B N4B 1.462(3) . ? C17B C18B 1.507(3) . ? 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 N1A C1A N2A 105.61(17) . . ? N1A C1A S1A 126.84(17) . . ? N2A C1A S1A 127.55(16) . . ? C3A C2A N1A 106.92(18) . . ? C2A C3A N2A 107.8(2) . . ? N2A C4A C5A 111.99(18) . . ? N1A C6A C7A 112.95(18) . . ? C12A C7A C8A 119.56(18) . . ? C12A C7A C6A 119.14(19) . . ? C8A C7A C6A 121.29(18) . . ? C9A C8A C7A 119.97(19) . . ? C10A C9A C8A 120.2(2) . . ? C9A C10A C11A 120.45(19) . . ? C12A C11A C10A 118.79(18) . . ? C12A C11A C13A 119.62(19) . . ? C10A C11A C13A 121.56(18) . . ? C7A C12A C11A 121.0(2) . . ? N3A C13A C11A 113.27(18) . . ? N4A C14A N3A 105.38(18) . . ? N4A C14A S2A 127.30(17) . . ? N3A C14A S2A 127.32(17) . . ? C16A C15A N3A 107.52(19) . . ? C15A C16A N4A 107.38(19) . . ? N4A C17A C18A 112.49(19) . . ? C1A N1A C2A 109.84(18) . . ? C1A N1A C6A 125.53(18) . . ? C2A N1A C6A 124.59(17) . . ? C1A N2A C3A 109.80(18) . . ? C1A N2A C4A 125.24(17) . . ? C3A N2A C4A 124.95(19) . . ? C14A N3A C15A 109.60(18) . . ? C14A N3A C13A 124.36(18) . . ? C15A N3A C13A 125.55(18) . . ? C14A N4A C16A 110.12(18) . . ? C14A N4A C17A 124.89(19) . . ? C16A N4A C17A 124.98(19) . . ? N2B C1B N1B 105.25(18) . . ? N2B C1B S1B 127.43(17) . . ? N1B C1B S1B 127.31(16) . . ? C3B C2B N1B 107.3(2) . . ? C2B C3B N2B 107.90(19) . . ? N2B C4B C5B 111.6(2) . . ? N1B C6B C7B 111.66(18) . . ? C12B C7B C8B 119.0(2) . . ? C12B C7B C6B 120.3(2) . . ? C8B C7B C6B 120.7(2) . . ? C9B C8B C7B 120.6(2) . . ? C8B C9B C10B 120.3(2) . . ? C9B C10B C11B 120.0(2) . . ? C10B C11B C12B 118.7(2) . . ? C10B C11B C13B 122.5(2) . . ? C12B C11B C13B 118.82(19) . . ? C7B C12B C11B 121.4(2) . . ? N3B C13B C11B 113.85(19) . . ? N4B C14B N3B 104.93(18) . . ? N4B C14B S2B 128.26(16) . . ? N3B C14B S2B 126.80(17) . . ? C16B C15B N3B 106.7(2) . . ? C15B C16B N4B 108.1(2) . . ? N4B C17B C18B 112.66(19) . . ? C1B N1B C2B 109.75(17) . . ? C1B N1B C6B 124.69(18) . . ? C2B N1B C6B 125.49(19) . . ? C1B N2B C3B 109.84(18) . . ? C1B N2B C4B 124.68(19) . . ? C3B N2B C4B 125.45(18) . . ? C14B N3B C15B 110.33(19) . . ? C14B N3B C13B 124.36(19) . . ? C15B N3B C13B 125.01(19) . . ? C14B N4B C16B 109.87(18) . . ? C14B N4B C17B 124.63(19) . . ? C16B N4B C17B 125.5(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.517 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.071