# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_name 'Prof. Dr. Ulrich Siemeling' _publ_contact_author_address ; Institute of Chemistry University of Kassel D-34109 Kassel Germany ; _publ_contact_author_phone '+0049 561 804 4576' _publ_contact_author_fax '+0049 561 804 4777' _publ_contact_author_email siemeling@uni-kassl.de _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter ; ; #===================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #===================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Nitron: a stable N-heterocyclic carbene that has been commercially available for more than a century ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'F\"arber, Christian' ? ; Institute of Chemistry University of Kassel D-34132 Kassel Germany ; 'Leibold, Michael' ? ; Institute of Chemistry University of Kassel D-34132 Kassel Germany ; 'Bruhn, Clemens' ? ; Institute of Chemistry University of Kassel D-34132 Kassel Germany ; 'Maurer, Martin' ? ; Institute of Chemistry University of Kassel D-34132 Kassel Germany ; 'Siemeling, Ulrich' ? ; Institute of Chemistry University of Kassel D-34132 Kassel Germany ; #============================================================================ data_i0953 _database_code_depnum_ccdc_archive 'CCDC 848861' #TrackingRef '7648_web_deposit_cif_file_0_ClemensBruhn_1318591330.final_publus94.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 Cl N4 O3 Rh' _chemical_formula_weight 580.87 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' O O 0.0106 0.0060 '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' Rh Rh -1.1178 0.9187 '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 n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 16.4133(9) _cell_length_b 24.4635(16) _cell_length_c 6.4734(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2599.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 10534 _cell_measurement_theta_min 1.49 _cell_measurement_theta_max 25.60 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.794 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.7834 _exptl_absorpt_correction_T_max 0.9595 _exptl_absorpt_process_details 'X-red ver. 1.31 (Stoe & Cie. 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _diffrn_source_voltage 50 _diffrn_source_current 30 _diffrn_source_power 1.50 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_measurement_method 'rotation method' _diffrn_measurement_details ; 118 frames, detector distance = 135 mm ; _diffrn_standards_decay_% none _diffrn_reflns_number 10661 _diffrn_reflns_av_R_equivalents 0.0637 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4330 _reflns_number_gt 3397 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0610P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(5) _refine_ls_number_reflns 4330 _refine_ls_number_parameters 322 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _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 0.2524(3) 0.4266(2) 0.7545(9) 0.0330(12) Uani 1 1 d . . . C2 C 0.2911(3) 0.35097(17) 0.9163(8) 0.0329(10) Uani 1 1 d . . . C3 C 0.2379(3) 0.5372(2) 0.8502(11) 0.0466(15) Uani 1 1 d . . . C4 C 0.2645(3) 0.5715(2) 0.4755(10) 0.0435(14) Uani 1 1 d . . . C5 C 0.1051(3) 0.41373(18) 0.8227(9) 0.0371(11) Uani 1 1 d . . . C6 C 0.0734(3) 0.4365(2) 0.6445(9) 0.0432(13) Uani 1 1 d . . . H6A H 0.1072 0.4429 0.5278 0.052 Uiso 1 1 calc R . . C7 C -0.0097(3) 0.4501(2) 0.6390(12) 0.0529(16) Uani 1 1 d . . . H7A H -0.0325 0.4661 0.5184 0.063 Uiso 1 1 calc R . . C8 C -0.0581(3) 0.4402(2) 0.8086(13) 0.0559(15) Uani 1 1 d . . . H8A H -0.1142 0.4496 0.8047 0.067 Uiso 1 1 calc R . . C9 C -0.0263(4) 0.4170(3) 0.9815(12) 0.0587(17) Uani 1 1 d . . . H9A H -0.0607 0.4101 1.0966 0.070 Uiso 1 1 calc R . . C10 C 0.0568(3) 0.4033(2) 0.9927(10) 0.0472(13) Uani 1 1 d . . . H10A H 0.0790 0.3872 1.1138 0.057 Uiso 1 1 calc R . . C11 C 0.4020(3) 0.40928(18) 0.7621(8) 0.0328(10) Uani 1 1 d . . . C12 C 0.4357(3) 0.3961(2) 0.5755(10) 0.0454(14) Uani 1 1 d . . . H12A H 0.4050 0.3769 0.4744 0.054 Uiso 1 1 calc R . . C13 C 0.5171(3) 0.4116(3) 0.5363(10) 0.0501(16) Uani 1 1 d . . . H13A H 0.5420 0.4028 0.4080 0.060 Uiso 1 1 calc R . . C14 C 0.5602(3) 0.4395(2) 0.6859(11) 0.0507(16) Uani 1 1 d . . . H14A H 0.6147 0.4504 0.6586 0.061 Uiso 1 1 calc R . . C15 C 0.5259(3) 0.4519(2) 0.8729(11) 0.0506(15) Uani 1 1 d . . . H15A H 0.5565 0.4710 0.9741 0.061 Uiso 1 1 calc R . . C16 C 0.4456(3) 0.4363(2) 0.9147(11) 0.0444(13) Uani 1 1 d . . . H16A H 0.4214 0.4440 1.0448 0.053 Uiso 1 1 calc R . . C17 C 0.3183(3) 0.27624(18) 1.1564(9) 0.0384(12) Uani 1 1 d . . . C18 C 0.2707(3) 0.2936(2) 1.3193(10) 0.0444(12) Uani 1 1 d . . . H18A H 0.2510 0.3301 1.3215 0.053 Uiso 1 1 calc R . . C19 C 0.2512(3) 0.2581(2) 1.4811(11) 0.0491(14) Uani 1 1 d . . . H19A H 0.2190 0.2703 1.5939 0.059 Uiso 1 1 calc R . . C20 C 0.2797(4) 0.2047(2) 1.4743(11) 0.0561(16) Uani 1 1 d . . . H20A H 0.2660 0.1800 1.5822 0.067 Uiso 1 1 calc R . . C21 C 0.3271(4) 0.1873(2) 1.3141(12) 0.0597(17) Uani 1 1 d . . . H21A H 0.3465 0.1507 1.3126 0.072 Uiso 1 1 calc R . . C22 C 0.3475(4) 0.22255(19) 1.1517(11) 0.0535(16) Uani 1 1 d . . . H22A H 0.3806 0.2102 1.0407 0.064 Uiso 1 1 calc R . . C23 C 0.5754(5) 0.2796(3) 0.8962(16) 0.087(2) Uani 1 1 d . . . H23B H 0.6021 0.2435 0.9058 0.104 Uiso 1 1 calc R . . H23A H 0.6081 0.3032 0.8033 0.104 Uiso 1 1 calc R . . C24 C 0.5693(6) 0.3042(4) 1.0981(18) 0.102(3) Uani 1 1 d . . . H24A H 0.5305 0.2835 1.1823 0.122 Uiso 1 1 calc R . . H24B H 0.5505 0.3420 1.0845 0.122 Uiso 1 1 calc R . . H24C H 0.6229 0.3037 1.1649 0.122 Uiso 1 1 calc R . . C25 C 0.4938(4) 0.2591(3) 0.6041(17) 0.0704(18) Uani 1 1 d . . . H25B H 0.5333 0.2828 0.5310 0.084 Uiso 1 1 calc R . . H25A H 0.4393 0.2661 0.5442 0.084 Uiso 1 1 calc R . . C26 C 0.5160(5) 0.2008(3) 0.5667(16) 0.078(2) Uani 1 1 d . . . H26C H 0.5099 0.1924 0.4195 0.094 Uiso 1 1 calc R . . H26B H 0.4800 0.1771 0.6474 0.094 Uiso 1 1 calc R . . H26A H 0.5726 0.1947 0.6086 0.094 Uiso 1 1 calc R . . N1 N 0.2110(2) 0.35099(15) 0.9334(7) 0.0377(10) Uani 1 1 d . . . N2 N 0.1894(2) 0.39892(15) 0.8306(7) 0.0346(9) Uani 1 1 d . . . N3 N 0.3180(2) 0.39515(14) 0.8045(8) 0.0356(9) Uani 1 1 d . . . N4 N 0.3428(3) 0.31270(16) 0.9972(8) 0.0420(10) Uani 1 1 d . . . H4 H 0.396(4) 0.309(3) 0.915(13) 0.08(2) Uiso 1 1 d . . . O1 O 0.2263(3) 0.56029(19) 0.9939(8) 0.0633(12) Uani 1 1 d . . . O2 O 0.2686(3) 0.61475(15) 0.4064(7) 0.0543(11) Uani 1 1 d . . . O3 O 0.4926(3) 0.27375(17) 0.8163(9) 0.0620(12) Uani 1 1 d . . . Cl1 Cl 0.26955(9) 0.45345(5) 0.2893(2) 0.0481(3) Uani 1 1 d . . . Rh1 Rh 0.256491(16) 0.501471(14) 0.60379(17) 0.03320(11) 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) 0.038(3) 0.033(3) 0.000(2) 0.003(2) 0.0020(18) C2 0.035(2) 0.029(2) 0.035(3) 0.002(2) 0.007(2) -0.0012(18) C3 0.044(3) 0.033(2) 0.063(5) 0.012(3) -0.019(3) 0.006(2) C4 0.036(3) 0.054(3) 0.041(4) -0.012(3) -0.001(3) 0.006(2) C5 0.030(2) 0.035(2) 0.046(3) -0.004(2) 0.001(2) -0.0024(18) C6 0.029(2) 0.053(3) 0.047(4) 0.003(3) -0.002(2) -0.003(2) C7 0.033(2) 0.052(3) 0.073(5) 0.003(3) -0.004(3) 0.004(2) C8 0.032(3) 0.063(3) 0.073(5) -0.002(4) 0.003(3) 0.006(2) C9 0.036(3) 0.068(4) 0.072(5) -0.004(4) 0.022(3) 0.000(3) C10 0.037(3) 0.050(3) 0.054(4) 0.000(3) 0.010(3) -0.001(2) C11 0.026(2) 0.032(2) 0.041(3) 0.005(2) 0.004(2) 0.0026(17) C12 0.034(2) 0.051(3) 0.051(4) -0.001(3) 0.009(3) -0.0031(19) C13 0.035(3) 0.063(3) 0.052(4) 0.010(3) 0.014(2) 0.003(3) C14 0.028(3) 0.048(3) 0.076(5) 0.017(3) 0.006(3) 0.000(2) C15 0.028(2) 0.053(3) 0.071(5) -0.004(3) -0.003(3) -0.005(2) C16 0.030(3) 0.049(3) 0.054(4) -0.008(3) 0.000(3) 0.001(2) C17 0.039(3) 0.034(2) 0.042(3) 0.009(2) 0.000(2) -0.0019(18) C18 0.041(3) 0.044(3) 0.048(3) 0.003(2) 0.008(3) 0.004(2) C19 0.045(3) 0.050(3) 0.053(4) 0.004(3) 0.010(3) -0.003(2) C20 0.069(4) 0.048(3) 0.051(4) 0.014(3) 0.007(3) -0.002(3) C21 0.080(4) 0.035(3) 0.064(4) 0.009(3) 0.013(4) 0.001(3) C22 0.064(3) 0.037(3) 0.060(4) 0.003(3) 0.012(3) 0.003(2) C23 0.078(5) 0.090(5) 0.093(7) -0.006(5) 0.000(5) 0.014(4) C24 0.109(6) 0.110(6) 0.086(6) -0.010(6) 0.006(7) -0.015(5) C25 0.075(4) 0.069(4) 0.067(5) 0.005(5) 0.013(5) 0.013(3) C26 0.080(5) 0.064(4) 0.091(7) 0.000(4) 0.006(5) 0.005(3) N1 0.033(2) 0.0335(18) 0.047(3) 0.0035(19) 0.002(2) -0.0023(16) N2 0.0280(19) 0.0350(18) 0.041(3) 0.0059(18) 0.0000(18) -0.0029(15) N3 0.028(2) 0.0324(18) 0.047(3) 0.0031(19) 0.004(2) -0.0015(14) N4 0.038(2) 0.034(2) 0.053(3) 0.009(2) 0.007(2) 0.0052(18) O1 0.088(3) 0.056(2) 0.046(3) 0.009(2) 0.006(3) 0.024(2) O2 0.070(3) 0.0347(19) 0.058(3) 0.0101(18) 0.000(2) -0.0019(17) O3 0.039(2) 0.072(2) 0.075(4) 0.004(3) 0.003(2) 0.0115(19) Cl1 0.0587(8) 0.0438(6) 0.0417(7) -0.0001(6) 0.0035(8) 0.0004(6) Rh1 0.02905(15) 0.03348(17) 0.03707(19) 0.00150(18) 0.0002(3) 0.00037(14) _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 1.330(6) . ? C1 N3 1.363(6) . ? C1 Rh1 2.077(5) . ? C2 N1 1.320(6) . ? C2 N4 1.368(6) . ? C2 N3 1.374(6) . ? C3 O1 1.105(8) . ? C3 Rh1 1.844(7) . ? C4 O2 1.150(7) . ? C4 Rh1 1.909(6) . ? C5 C10 1.381(8) . ? C5 C6 1.383(8) . ? C5 N2 1.431(6) . ? C6 C7 1.404(7) . ? C6 H6A 0.9500 . ? C7 C8 1.377(10) . ? C7 H7A 0.9500 . ? C8 C9 1.359(10) . ? C8 H8A 0.9500 . ? C9 C10 1.406(8) . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C11 C12 1.367(8) . ? C11 C16 1.387(8) . ? C11 N3 1.447(6) . ? C12 C13 1.412(7) . ? C12 H12A 0.9500 . ? C13 C14 1.380(9) . ? C13 H13A 0.9500 . ? C14 C15 1.369(9) . ? C14 H14A 0.9500 . ? C15 C16 1.398(8) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 C18 1.379(8) . ? C17 C22 1.399(6) . ? C17 N4 1.421(7) . ? C18 C19 1.398(8) . ? C18 H18A 0.9500 . ? C19 C20 1.389(8) . ? C19 H19A 0.9500 . ? C20 C21 1.364(9) . ? C20 H20A 0.9500 . ? C21 C22 1.400(9) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? C23 C24 1.442(14) . ? C23 O3 1.461(9) . ? C23 H23B 0.9900 . ? C23 H23A 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 O3 1.420(12) . ? C25 C26 1.490(9) . ? C25 H25B 0.9900 . ? C25 H25A 0.9900 . ? C26 H26C 0.9800 . ? C26 H26B 0.9800 . ? C26 H26A 0.9800 . ? N1 N2 1.394(6) . ? N4 H4 1.02(7) . ? Cl1 Rh1 2.3601(19) . ? 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 N3 103.8(4) . . ? N2 C1 Rh1 130.4(3) . . ? N3 C1 Rh1 125.7(3) . . ? N1 C2 N4 125.9(4) . . ? N1 C2 N3 111.4(4) . . ? N4 C2 N3 122.7(4) . . ? O1 C3 Rh1 177.4(5) . . ? O2 C4 Rh1 177.0(5) . . ? C10 C5 C6 121.5(5) . . ? C10 C5 N2 118.7(5) . . ? C6 C5 N2 119.7(5) . . ? C5 C6 C7 118.8(6) . . ? C5 C6 H6A 120.6 . . ? C7 C6 H6A 120.6 . . ? C8 C7 C6 119.9(6) . . ? C8 C7 H7A 120.0 . . ? C6 C7 H7A 120.0 . . ? C9 C8 C7 120.6(5) . . ? C9 C8 H8A 119.7 . . ? C7 C8 H8A 119.7 . . ? C8 C9 C10 121.0(6) . . ? C8 C9 H9A 119.5 . . ? C10 C9 H9A 119.5 . . ? C5 C10 C9 118.2(6) . . ? C5 C10 H10A 120.9 . . ? C9 C10 H10A 120.9 . . ? C12 C11 C16 122.2(5) . . ? C12 C11 N3 119.8(5) . . ? C16 C11 N3 118.0(5) . . ? C11 C12 C13 118.6(5) . . ? C11 C12 H12A 120.7 . . ? C13 C12 H12A 120.7 . . ? C14 C13 C12 119.4(6) . . ? C14 C13 H13A 120.3 . . ? C12 C13 H13A 120.3 . . ? C15 C14 C13 121.3(5) . . ? C15 C14 H14A 119.4 . . ? C13 C14 H14A 119.4 . . ? C14 C15 C16 119.9(6) . . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? C11 C16 C15 118.6(6) . . ? C11 C16 H16A 120.7 . . ? C15 C16 H16A 120.7 . . ? C18 C17 C22 120.0(5) . . ? C18 C17 N4 121.4(4) . . ? C22 C17 N4 118.5(5) . . ? C17 C18 C19 120.8(5) . . ? C17 C18 H18A 119.6 . . ? C19 C18 H18A 119.6 . . ? C20 C19 C18 118.9(6) . . ? C20 C19 H19A 120.5 . . ? C18 C19 H19A 120.5 . . ? C21 C20 C19 120.6(6) . . ? C21 C20 H20A 119.7 . . ? C19 C20 H20A 119.7 . . ? C20 C21 C22 121.1(5) . . ? C20 C21 H21A 119.5 . . ? C22 C21 H21A 119.5 . . ? C17 C22 C21 118.7(6) . . ? C17 C22 H22A 120.7 . . ? C21 C22 H22A 120.7 . . ? C24 C23 O3 107.3(7) . . ? C24 C23 H23B 110.2 . . ? O3 C23 H23B 110.2 . . ? C24 C23 H23A 110.2 . . ? O3 C23 H23A 110.2 . . ? H23B C23 H23A 108.5 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O3 C25 C26 113.7(8) . . ? O3 C25 H25B 108.8 . . ? C26 C25 H25B 108.8 . . ? O3 C25 H25A 108.8 . . ? C26 C25 H25A 108.8 . . ? H25B C25 H25A 107.7 . . ? C25 C26 H26C 109.5 . . ? C25 C26 H26B 109.5 . . ? H26C C26 H26B 109.5 . . ? C25 C26 H26A 109.5 . . ? H26C C26 H26A 109.5 . . ? H26B C26 H26A 109.5 . . ? C2 N1 N2 102.3(3) . . ? C1 N2 N1 114.1(4) . . ? C1 N2 C5 127.5(4) . . ? N1 N2 C5 118.4(4) . . ? C1 N3 C2 108.3(4) . . ? C1 N3 C11 125.0(4) . . ? C2 N3 C11 126.5(4) . . ? C2 N4 C17 122.2(4) . . ? C2 N4 H4 113(4) . . ? C17 N4 H4 125(4) . . ? C25 O3 C23 110.8(6) . . ? C3 Rh1 C4 87.8(2) . . ? C3 Rh1 C1 90.4(2) . . ? C4 Rh1 C1 177.0(2) . . ? C3 Rh1 Cl1 175.52(18) . . ? C4 Rh1 Cl1 93.74(19) . . ? C1 Rh1 Cl1 88.23(16) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.563 _refine_diff_density_min -0.772 _refine_diff_density_rms 0.109 #===================================================================== data_i0810 _database_code_depnum_ccdc_archive 'CCDC 848862' #TrackingRef '7648_web_deposit_cif_file_0_ClemensBruhn_1318591330.final_publus94.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H28 Cl N4 Rh, C H Cl3' _chemical_formula_sum 'C29 H29 Cl4 N4 Rh' _chemical_formula_weight 678.27 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' Rh Rh -1.1178 0.9187 '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/n' _symmetry_Int_Tables_number 14 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 11.2724(9) _cell_length_b 16.7158(10) _cell_length_c 15.8324(12) _cell_angle_alpha 90.00 _cell_angle_beta 101.116(6) _cell_angle_gamma 90.00 _cell_volume 2927.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 17648 _cell_measurement_theta_min 1.79 _cell_measurement_theta_max 25.61 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.975 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.7711 _exptl_absorpt_correction_T_max 0.9351 _exptl_absorpt_process_details 'X-red ver. 1.31 (Stoe & Cie. 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _diffrn_source_voltage 50 _diffrn_source_current 30 _diffrn_source_power 1.50 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_measurement_method 'rotation method' _diffrn_measurement_details ; 125 frames, detector distance = 135 mm ; _diffrn_standards_decay_% none _diffrn_reflns_number 15306 _diffrn_reflns_av_R_equivalents 0.0677 _diffrn_reflns_av_sigmaI/netI 0.0564 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5137 _reflns_number_gt 3906 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0813P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5137 _refine_ls_number_parameters 358 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1225 _refine_ls_wR_factor_gt 0.1156 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.945 _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 -0.1356(4) 0.1014(3) 0.6137(3) 0.0389(9) Uani 1 1 d . . . C2 C -0.2654(4) 0.0285(3) 0.5174(3) 0.0402(10) Uani 1 1 d . . . C3 C -0.0566(4) 0.0821(3) 0.8012(3) 0.0438(10) Uani 1 1 d . . . H34 H -0.110(5) 0.043(3) 0.774(3) 0.053 Uiso 1 1 d . . . C4 C -0.0973(5) 0.1631(3) 0.7954(3) 0.0447(10) Uani 1 1 d . . . H30 H -0.176(5) 0.172(3) 0.761(3) 0.054 Uiso 1 1 d . . . C5 C -0.0446(5) 0.2288(3) 0.8581(3) 0.0523(12) Uani 1 1 d . . . H5A H -0.0168 0.2050 0.9158 0.063 Uiso 1 1 calc R . . H5B H -0.1090 0.2680 0.8626 0.063 Uiso 1 1 calc R . . C6 C 0.0623(5) 0.2730(3) 0.8306(3) 0.0560(13) Uani 1 1 d . . . H6A H 0.0303 0.3192 0.7941 0.067 Uiso 1 1 calc R . . H6B H 0.1161 0.2942 0.8827 0.067 Uiso 1 1 calc R . . C7 C 0.1355(5) 0.2219(3) 0.7822(3) 0.0464(11) Uani 1 1 d . . . H32 H 0.167(5) 0.253(3) 0.744(3) 0.056 Uiso 1 1 d . . . C8 C 0.1772(4) 0.1459(3) 0.8041(3) 0.0457(11) Uani 1 1 d . . . H31 H 0.229(5) 0.118(3) 0.771(3) 0.055 Uiso 1 1 d . . . C9 C 0.1584(4) 0.1032(3) 0.8850(3) 0.0476(11) Uani 1 1 d . . . H9A H 0.1489 0.1434 0.9292 0.057 Uiso 1 1 calc R . . H9B H 0.2308 0.0706 0.9079 0.057 Uiso 1 1 calc R . . C10 C 0.0462(4) 0.0487(3) 0.8678(3) 0.0487(11) Uani 1 1 d . . . H10A H 0.0697 -0.0042 0.8480 0.058 Uiso 1 1 calc R . . H10B H 0.0175 0.0404 0.9224 0.058 Uiso 1 1 calc R . . C11 C -0.2569(4) 0.2261(3) 0.5868(2) 0.0390(9) Uani 1 1 d . . . C12 C -0.3771(4) 0.2469(3) 0.5910(3) 0.0443(10) Uani 1 1 d . . . H12A H -0.4396 0.2079 0.5820 0.053 Uiso 1 1 calc R . . C13 C -0.4017(5) 0.3259(3) 0.6087(3) 0.0495(11) Uani 1 1 d . . . H13A H -0.4817 0.3410 0.6126 0.059 Uiso 1 1 calc R . . C14 C -0.3104(5) 0.3834(3) 0.6208(3) 0.0481(11) Uani 1 1 d . . . H14A H -0.3283 0.4370 0.6336 0.058 Uiso 1 1 calc R . . C15 C -0.1945(5) 0.3627(3) 0.6142(3) 0.0475(11) Uani 1 1 d . . . H15A H -0.1331 0.4024 0.6212 0.057 Uiso 1 1 calc R . . C16 C -0.1664(4) 0.2835(3) 0.5971(3) 0.0428(10) Uani 1 1 d . . . H16A H -0.0862 0.2692 0.5927 0.051 Uiso 1 1 calc R . . C17 C -0.0860(4) -0.0443(3) 0.6070(2) 0.0391(9) Uani 1 1 d . . . C18 C -0.1436(4) -0.1135(3) 0.6288(3) 0.0440(10) Uani 1 1 d . . . H18A H -0.2286 -0.1144 0.6253 0.053 Uiso 1 1 calc R . . C19 C -0.0735(5) -0.1815(3) 0.6558(3) 0.0516(12) Uani 1 1 d . . . H19A H -0.1112 -0.2290 0.6702 0.062 Uiso 1 1 calc R . . C20 C 0.0516(5) -0.1795(3) 0.6614(3) 0.0512(12) Uani 1 1 d . . . H20A H 0.0989 -0.2255 0.6802 0.061 Uiso 1 1 calc R . . C21 C 0.1073(5) -0.1102(3) 0.6396(3) 0.0501(11) Uani 1 1 d . . . H21A H 0.1924 -0.1090 0.6434 0.060 Uiso 1 1 calc R . . C22 C 0.0380(4) -0.0420(3) 0.6122(3) 0.0408(10) Uani 1 1 d . . . H22A H 0.0757 0.0053 0.5973 0.049 Uiso 1 1 calc R . . C23 C -0.4057(4) -0.0376(3) 0.3967(3) 0.0419(10) Uani 1 1 d . . . C24 C -0.4935(4) 0.0214(3) 0.3809(3) 0.0444(10) Uani 1 1 d . . . H24A H -0.4912 0.0657 0.4189 0.053 Uiso 1 1 calc R . . C25 C -0.5862(5) 0.0147(3) 0.3076(3) 0.0499(11) Uani 1 1 d . . . H25A H -0.6458 0.0555 0.2961 0.060 Uiso 1 1 calc R . . C26 C -0.5930(4) -0.0492(3) 0.2522(3) 0.0476(11) Uani 1 1 d . . . H26A H -0.6564 -0.0528 0.2032 0.057 Uiso 1 1 calc R . . C27 C -0.5058(5) -0.1078(3) 0.2692(3) 0.0562(12) Uani 1 1 d . . . H27A H -0.5092 -0.1519 0.2310 0.067 Uiso 1 1 calc R . . C28 C -0.4124(4) -0.1039(3) 0.3413(3) 0.0469(11) Uani 1 1 d . . . H28A H -0.3541 -0.1455 0.3527 0.056 Uiso 1 1 calc R . . C29 C 0.1445(5) 0.3635(3) 0.5303(4) 0.0598(13) Uani 1 1 d . . . H29A H 0.1388 0.3043 0.5378 0.072 Uiso 1 1 calc R . . N1 N -0.2308(3) 0.1440(2) 0.5726(2) 0.0393(8) Uani 1 1 d . . . N2 N -0.3135(3) 0.1006(2) 0.5119(2) 0.0405(8) Uani 1 1 d . . . N3 N -0.1585(3) 0.0259(2) 0.5792(2) 0.0376(8) Uani 1 1 d . . . N4 N -0.3072(4) -0.0370(2) 0.4685(2) 0.0422(9) Uani 1 1 d . . . H33 H -0.260(5) -0.075(3) 0.465(3) 0.051 Uiso 1 1 d . . . Cl1 Cl 0.11034(10) 0.16711(7) 0.58223(6) 0.0432(3) Uani 1 1 d . . . Cl2 Cl 0.15629(16) 0.40992(10) 0.63278(9) 0.0758(4) Uani 1 1 d . . . Cl3 Cl 0.27313(15) 0.38415(13) 0.48553(11) 0.0845(5) Uani 1 1 d . . . Cl4 Cl 0.01364(14) 0.39615(11) 0.45952(9) 0.0723(4) Uani 1 1 d . . . Rh1 Rh 0.00922(3) 0.13992(2) 0.701127(19) 0.03756(13) 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 0.039(2) 0.042(2) 0.038(2) -0.0021(18) 0.0107(18) 0.000(2) C2 0.040(2) 0.045(3) 0.035(2) 0.0012(18) 0.0082(18) -0.001(2) C3 0.043(2) 0.051(3) 0.037(2) 0.0015(19) 0.0055(18) -0.001(2) C4 0.050(3) 0.050(3) 0.031(2) -0.0010(18) 0.0020(19) 0.004(2) C5 0.059(3) 0.057(3) 0.040(2) -0.007(2) 0.009(2) 0.006(3) C6 0.071(3) 0.051(3) 0.043(2) -0.008(2) 0.003(2) -0.005(3) C7 0.052(3) 0.051(3) 0.034(2) -0.0026(19) 0.0037(19) -0.015(2) C8 0.043(2) 0.055(3) 0.035(2) 0.0001(19) -0.0041(18) -0.008(2) C9 0.046(3) 0.054(3) 0.040(2) 0.005(2) 0.0016(19) -0.001(2) C10 0.050(3) 0.054(3) 0.040(2) 0.007(2) 0.004(2) 0.000(2) C11 0.047(3) 0.039(2) 0.0311(19) -0.0013(17) 0.0076(17) 0.004(2) C12 0.046(3) 0.045(3) 0.041(2) -0.0021(19) 0.0089(19) 0.001(2) C13 0.052(3) 0.057(3) 0.039(2) -0.002(2) 0.007(2) 0.009(3) C14 0.060(3) 0.044(3) 0.037(2) -0.0053(18) 0.001(2) 0.011(2) C15 0.054(3) 0.042(2) 0.043(2) 0.000(2) 0.003(2) 0.004(2) C16 0.045(3) 0.040(2) 0.043(2) -0.0011(18) 0.0065(19) 0.004(2) C17 0.047(3) 0.038(2) 0.0320(19) 0.0033(17) 0.0052(17) 0.003(2) C18 0.043(2) 0.045(2) 0.045(2) 0.0051(19) 0.0117(19) 0.000(2) C19 0.062(3) 0.044(3) 0.049(2) 0.009(2) 0.012(2) 0.002(2) C20 0.053(3) 0.045(3) 0.055(3) 0.009(2) 0.010(2) 0.009(2) C21 0.047(3) 0.056(3) 0.049(2) 0.006(2) 0.011(2) 0.007(2) C22 0.042(2) 0.041(2) 0.040(2) 0.0005(18) 0.0074(18) 0.003(2) C23 0.039(2) 0.047(3) 0.039(2) 0.0029(19) 0.0040(18) -0.003(2) C24 0.048(3) 0.045(3) 0.040(2) -0.0062(19) 0.0070(19) 0.000(2) C25 0.049(3) 0.057(3) 0.043(2) 0.000(2) 0.006(2) 0.005(2) C26 0.040(3) 0.054(3) 0.046(2) -0.005(2) 0.004(2) -0.002(2) C27 0.057(3) 0.053(3) 0.056(3) -0.013(2) 0.004(2) -0.005(3) C28 0.045(3) 0.046(3) 0.049(2) -0.008(2) 0.006(2) -0.002(2) C29 0.068(3) 0.049(3) 0.063(3) 0.010(2) 0.012(3) -0.004(3) N1 0.043(2) 0.0383(19) 0.0354(17) 0.0000(15) 0.0033(15) 0.0008(17) N2 0.043(2) 0.041(2) 0.0354(17) 0.0002(15) 0.0039(15) -0.0002(18) N3 0.040(2) 0.0382(19) 0.0339(16) 0.0001(14) 0.0043(14) -0.0005(16) N4 0.043(2) 0.042(2) 0.0414(19) -0.0041(16) 0.0060(16) 0.0032(18) Cl1 0.0474(6) 0.0437(6) 0.0402(5) 0.0011(4) 0.0127(4) 0.0007(5) Cl2 0.0890(11) 0.0796(11) 0.0568(7) 0.0070(7) 0.0089(7) -0.0170(9) Cl3 0.0587(9) 0.1131(14) 0.0837(10) 0.0113(9) 0.0190(8) 0.0000(9) Cl4 0.0622(9) 0.0913(11) 0.0631(8) 0.0062(7) 0.0114(7) 0.0084(8) Rh1 0.0401(2) 0.0395(2) 0.03238(18) 0.00009(13) 0.00538(13) -0.00080(16) _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 N1 1.347(6) . ? C1 N3 1.380(6) . ? C1 Rh1 2.030(4) . ? C2 N2 1.317(6) . ? C2 N4 1.372(6) . ? C2 N3 1.399(5) . ? C3 C4 1.426(7) . ? C3 C10 1.516(6) . ? C3 Rh1 2.109(4) . ? C3 H34 0.94(5) . ? C4 C5 1.524(7) . ? C4 Rh1 2.123(5) . ? C4 H30 0.95(6) . ? C5 C6 1.546(8) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.497(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.375(7) . ? C7 Rh1 2.202(5) . ? C7 H32 0.92(6) . ? C8 C9 1.516(6) . ? C8 Rh1 2.250(4) . ? C8 H31 0.98(6) . ? C9 C10 1.540(7) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.387(6) . ? C11 C12 1.413(6) . ? C11 N1 1.431(6) . ? C12 C13 1.389(7) . ? C12 H12A 0.9500 . ? C13 C14 1.394(8) . ? C13 H13A 0.9500 . ? C14 C15 1.374(7) . ? C14 H14A 0.9500 . ? C15 C16 1.400(6) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 C22 1.384(6) . ? C17 C18 1.402(6) . ? C17 N3 1.449(6) . ? C18 C19 1.403(7) . ? C18 H18A 0.9500 . ? C19 C20 1.396(7) . ? C19 H19A 0.9500 . ? C20 C21 1.393(7) . ? C20 H20A 0.9500 . ? C21 C22 1.402(7) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? C23 C24 1.386(7) . ? C23 C28 1.406(6) . ? C23 N4 1.428(6) . ? C24 C25 1.409(6) . ? C24 H24A 0.9500 . ? C25 C26 1.374(7) . ? C25 H25A 0.9500 . ? C26 C27 1.377(7) . ? C26 H26A 0.9500 . ? C27 C28 1.397(7) . ? C27 H27A 0.9500 . ? C28 H28A 0.9500 . ? C29 Cl4 1.758(6) . ? C29 Cl3 1.766(6) . ? C29 Cl2 1.780(6) . ? C29 H29A 1.0000 . ? N1 N2 1.405(5) . ? N4 H33 0.84(6) . ? Cl1 Rh1 2.4242(10) . ? 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 N1 C1 N3 102.8(4) . . ? N1 C1 Rh1 128.5(3) . . ? N3 C1 Rh1 128.7(3) . . ? N2 C2 N4 127.0(4) . . ? N2 C2 N3 111.3(4) . . ? N4 C2 N3 121.7(4) . . ? C4 C3 C10 126.0(4) . . ? C4 C3 Rh1 70.9(3) . . ? C10 C3 Rh1 111.0(3) . . ? C4 C3 H34 118(3) . . ? C10 C3 H34 114(3) . . ? Rh1 C3 H34 105(3) . . ? C3 C4 C5 124.2(4) . . ? C3 C4 Rh1 69.7(3) . . ? C5 C4 Rh1 112.8(3) . . ? C3 C4 H30 116(3) . . ? C5 C4 H30 117(3) . . ? Rh1 C4 H30 103(3) . . ? C4 C5 C6 112.8(4) . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C7 C6 C5 114.1(4) . . ? C7 C6 H6A 108.7 . . ? C5 C6 H6A 108.7 . . ? C7 C6 H6B 108.7 . . ? C5 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C6 126.3(4) . . ? C8 C7 Rh1 73.9(3) . . ? C6 C7 Rh1 107.2(3) . . ? C8 C7 H32 122(3) . . ? C6 C7 H32 110(3) . . ? Rh1 C7 H32 104(3) . . ? C7 C8 C9 123.5(5) . . ? C7 C8 Rh1 70.1(3) . . ? C9 C8 Rh1 110.9(3) . . ? C7 C8 H31 121(3) . . ? C9 C8 H31 115(3) . . ? Rh1 C8 H31 95(3) . . ? C8 C9 C10 111.9(4) . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C3 C10 C9 113.4(4) . . ? C3 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? C3 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C16 C11 C12 121.0(4) . . ? C16 C11 N1 120.8(4) . . ? C12 C11 N1 118.2(4) . . ? C13 C12 C11 118.2(5) . . ? C13 C12 H12A 120.9 . . ? C11 C12 H12A 120.9 . . ? C12 C13 C14 120.8(5) . . ? C12 C13 H13A 119.6 . . ? C14 C13 H13A 119.6 . . ? C15 C14 C13 120.3(5) . . ? C15 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? C14 C15 C16 120.4(5) . . ? C14 C15 H15A 119.8 . . ? C16 C15 H15A 119.8 . . ? C11 C16 C15 119.2(4) . . ? C11 C16 H16A 120.4 . . ? C15 C16 H16A 120.4 . . ? C22 C17 C18 121.2(4) . . ? C22 C17 N3 120.0(4) . . ? C18 C17 N3 118.8(4) . . ? C17 C18 C19 118.9(4) . . ? C17 C18 H18A 120.6 . . ? C19 C18 H18A 120.6 . . ? C20 C19 C18 120.2(5) . . ? C20 C19 H19A 119.9 . . ? C18 C19 H19A 119.9 . . ? C21 C20 C19 120.1(5) . . ? C21 C20 H20A 119.9 . . ? C19 C20 H20A 119.9 . . ? C20 C21 C22 120.1(5) . . ? C20 C21 H21A 119.9 . . ? C22 C21 H21A 119.9 . . ? C17 C22 C21 119.5(4) . . ? C17 C22 H22A 120.3 . . ? C21 C22 H22A 120.3 . . ? C24 C23 C28 119.9(4) . . ? C24 C23 N4 123.9(4) . . ? C28 C23 N4 116.2(4) . . ? C23 C24 C25 118.8(4) . . ? C23 C24 H24A 120.6 . . ? C25 C24 H24A 120.6 . . ? C26 C25 C24 121.9(5) . . ? C26 C25 H25A 119.0 . . ? C24 C25 H25A 119.0 . . ? C25 C26 C27 118.6(4) . . ? C25 C26 H26A 120.7 . . ? C27 C26 H26A 120.7 . . ? C26 C27 C28 121.6(5) . . ? C26 C27 H27A 119.2 . . ? C28 C27 H27A 119.2 . . ? C27 C28 C23 119.2(5) . . ? C27 C28 H28A 120.4 . . ? C23 C28 H28A 120.4 . . ? Cl4 C29 Cl3 109.7(3) . . ? Cl4 C29 Cl2 110.6(3) . . ? Cl3 C29 Cl2 111.0(3) . . ? Cl4 C29 H29A 108.5 . . ? Cl3 C29 H29A 108.5 . . ? Cl2 C29 H29A 108.5 . . ? C1 N1 N2 114.8(3) . . ? C1 N1 C11 126.9(4) . . ? N2 N1 C11 118.3(3) . . ? C2 N2 N1 102.5(3) . . ? C1 N3 C2 108.6(4) . . ? C1 N3 C17 124.7(3) . . ? C2 N3 C17 126.7(4) . . ? C2 N4 C23 125.7(4) . . ? C2 N4 H33 119(4) . . ? C23 N4 H33 110(4) . . ? C1 Rh1 C3 90.78(18) . . ? C1 Rh1 C4 92.73(18) . . ? C3 Rh1 C4 39.38(19) . . ? C1 Rh1 C7 159.92(19) . . ? C3 Rh1 C7 97.42(18) . . ? C4 Rh1 C7 82.35(19) . . ? C1 Rh1 C8 164.06(18) . . ? C3 Rh1 C8 81.07(18) . . ? C4 Rh1 C8 89.62(18) . . ? C7 Rh1 C8 35.96(18) . . ? C1 Rh1 Cl1 88.09(11) . . ? C3 Rh1 Cl1 162.84(14) . . ? C4 Rh1 Cl1 157.78(14) . . ? C7 Rh1 Cl1 89.30(12) . . ? C8 Rh1 Cl1 95.66(13) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.744 _refine_diff_density_min -1.356 _refine_diff_density_rms 0.092 #===================================================================== data_i0903a _database_code_depnum_ccdc_archive 'CCDC 848863' #TrackingRef '7648_web_deposit_cif_file_0_ClemensBruhn_1318591330.final_publus94.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 N4 S2, C H Cl3' _chemical_formula_sum 'C22 H17 Cl3 N4 S2' _chemical_formula_weight 507.87 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1388(11) _cell_length_b 10.3661(10) _cell_length_c 12.2102(12) _cell_angle_alpha 85.985(8) _cell_angle_beta 73.991(8) _cell_angle_gamma 64.991(8) _cell_volume 1116.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8645 _cell_measurement_theta_min 1.74 _cell_measurement_theta_max 25.64 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.317 _exptl_crystal_size_min 0.250 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.616 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.7886 _exptl_absorpt_correction_T_max 0.9130 _exptl_absorpt_process_details 'X-red ver. 1.31 (Stoe & Cie. 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _diffrn_source_voltage 50 _diffrn_source_current 30 _diffrn_source_power 1.50 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_measurement_method 'rotation method' _diffrn_measurement_details ; 140 frames, detector distance = 135 mm ; _diffrn_standards_decay_% none _diffrn_reflns_number 8335 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3919 _reflns_number_gt 3276 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0981P)^2^+0.6581P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3919 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1586 _refine_ls_wR_factor_gt 0.1550 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 C1 C 0.2428(4) -0.0051(3) 0.0015(3) 0.0257(7) Uani 1 1 d . . . C2 C 0.2381(4) 0.0700(3) -0.1073(3) 0.0281(7) Uani 1 1 d . . . C3 C 0.2278(4) -0.0462(3) 0.1833(3) 0.0264(7) Uani 1 1 d . . . C4 C 0.3286(4) -0.2631(3) -0.0579(3) 0.0278(7) Uani 1 1 d . . . C5 C 0.3136(4) -0.3836(3) -0.0089(3) 0.0314(7) Uani 1 1 d . . . H5A H 0.2712 -0.3833 0.0709 0.038 Uiso 1 1 calc R . . C6 C 0.3620(4) -0.5045(3) -0.0790(3) 0.0335(8) Uani 1 1 d . . . H6A H 0.3538 -0.5878 -0.0468 0.040 Uiso 1 1 calc R . . C7 C 0.4218(4) -0.5036(4) -0.1950(3) 0.0352(8) Uani 1 1 d . . . H7A H 0.4555 -0.5866 -0.2422 0.042 Uiso 1 1 calc R . . C8 C 0.4331(4) -0.3817(4) -0.2432(3) 0.0358(8) Uani 1 1 d . . . H8A H 0.4728 -0.3811 -0.3232 0.043 Uiso 1 1 calc R . . C9 C 0.3859(4) -0.2597(4) -0.1732(3) 0.0317(7) Uani 1 1 d . . . H9A H 0.3935 -0.1761 -0.2053 0.038 Uiso 1 1 calc R . . C10 C 0.1579(4) 0.2100(3) 0.1309(3) 0.0269(7) Uani 1 1 d . . . C11 C 0.0188(4) 0.3081(4) 0.1199(3) 0.0334(8) Uani 1 1 d . . . H11A H -0.0444 0.2786 0.0934 0.040 Uiso 1 1 calc R . . C12 C -0.0266(4) 0.4513(4) 0.1488(3) 0.0355(8) Uani 1 1 d . . . H12A H -0.1208 0.5208 0.1405 0.043 Uiso 1 1 calc R . . C13 C 0.0658(4) 0.4928(4) 0.1897(3) 0.0344(8) Uani 1 1 d . . . H13A H 0.0339 0.5904 0.2096 0.041 Uiso 1 1 calc R . . C14 C 0.2030(5) 0.3932(4) 0.2016(3) 0.0370(8) Uani 1 1 d . . . H14A H 0.2641 0.4224 0.2311 0.044 Uiso 1 1 calc R . . C15 C 0.2529(4) 0.2495(4) 0.1705(3) 0.0323(8) Uani 1 1 d . . . H15A H 0.3488 0.1807 0.1762 0.039 Uiso 1 1 calc R . . C16 C 0.1998(4) -0.1122(3) 0.3849(3) 0.0278(7) Uani 1 1 d . . . C17 C 0.2175(4) -0.2506(3) 0.3674(3) 0.0328(8) Uani 1 1 d . . . H17A H 0.2318 -0.2857 0.2932 0.039 Uiso 1 1 calc R . . C18 C 0.2139(4) -0.3368(4) 0.4596(3) 0.0349(8) Uani 1 1 d . . . H18A H 0.2259 -0.4312 0.4480 0.042 Uiso 1 1 calc R . . C19 C 0.1930(4) -0.2871(4) 0.5685(3) 0.0359(8) Uani 1 1 d . . . H19A H 0.1912 -0.3472 0.6307 0.043 Uiso 1 1 calc R . . C20 C 0.1748(4) -0.1499(4) 0.5856(3) 0.0337(8) Uani 1 1 d . . . H20A H 0.1605 -0.1153 0.6600 0.040 Uiso 1 1 calc R . . C21 C 0.1774(4) -0.0618(4) 0.4942(3) 0.0311(7) Uani 1 1 d . . . H21A H 0.1639 0.0330 0.5066 0.037 Uiso 1 1 calc R . . C22 C 0.3222(4) 0.2171(4) 0.5374(3) 0.0360(8) Uani 1 1 d . . . H22A H 0.3180 0.1508 0.6004 0.043 Uiso 1 1 calc R . . N1 N 0.2835(3) -0.1431(3) 0.0193(2) 0.0263(6) Uani 1 1 d . . . N2 N 0.2760(3) -0.1711(3) 0.1330(2) 0.0267(6) Uani 1 1 d . . . N3 N 0.2067(3) 0.0602(3) 0.1052(2) 0.0257(6) Uani 1 1 d . . . N4 N 0.1998(3) -0.0164(3) 0.2958(2) 0.0291(6) Uani 1 1 d . . . H4 H 0.168(5) 0.071(4) 0.330(3) 0.035 Uiso 1 1 d . . . S1 S 0.08997(11) 0.09700(9) -0.15538(8) 0.0352(2) Uani 1 1 d . . . S2 S 0.38396(11) 0.11399(9) -0.15950(8) 0.0353(3) Uani 1 1 d . . . Cl1 Cl 0.42318(11) 0.11487(9) 0.40614(8) 0.0400(3) Uani 1 1 d . . . Cl2 Cl 0.13526(11) 0.32813(10) 0.53164(9) 0.0453(3) Uani 1 1 d . . . Cl3 Cl 0.41459(12) 0.31696(10) 0.56331(8) 0.0435(3) 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 0.0257(17) 0.0246(15) 0.0267(17) 0.0017(13) -0.0068(13) -0.0107(13) C2 0.0350(19) 0.0221(15) 0.0248(16) 0.0021(12) -0.0072(14) -0.0105(13) C3 0.0272(17) 0.0256(15) 0.0266(17) 0.0031(13) -0.0072(13) -0.0116(13) C4 0.0275(17) 0.0243(15) 0.0322(18) 0.0002(13) -0.0108(14) -0.0096(13) C5 0.0358(19) 0.0282(16) 0.0306(18) 0.0013(13) -0.0098(15) -0.0134(14) C6 0.041(2) 0.0241(15) 0.039(2) 0.0028(14) -0.0176(16) -0.0131(14) C7 0.037(2) 0.0285(17) 0.039(2) -0.0062(14) -0.0137(16) -0.0094(15) C8 0.040(2) 0.0384(18) 0.0283(18) -0.0035(14) -0.0074(15) -0.0166(16) C9 0.0328(19) 0.0306(16) 0.0312(18) 0.0003(14) -0.0080(15) -0.0130(14) C10 0.0335(18) 0.0224(15) 0.0232(16) 0.0024(12) -0.0063(13) -0.0114(13) C11 0.035(2) 0.0311(17) 0.0354(19) 0.0023(14) -0.0096(15) -0.0148(15) C12 0.035(2) 0.0263(16) 0.037(2) 0.0057(14) -0.0069(16) -0.0086(15) C13 0.044(2) 0.0236(16) 0.0315(18) 0.0013(13) -0.0065(16) -0.0129(15) C14 0.048(2) 0.0320(18) 0.038(2) 0.0044(15) -0.0152(17) -0.0215(17) C15 0.035(2) 0.0290(16) 0.0344(18) 0.0042(14) -0.0135(15) -0.0130(15) C16 0.0267(17) 0.0283(16) 0.0271(17) 0.0052(13) -0.0074(14) -0.0110(13) C17 0.040(2) 0.0275(16) 0.0300(18) 0.0024(13) -0.0098(15) -0.0136(15) C18 0.042(2) 0.0278(16) 0.0352(19) 0.0052(14) -0.0113(16) -0.0149(15) C19 0.038(2) 0.0393(19) 0.0304(18) 0.0100(15) -0.0103(15) -0.0169(16) C20 0.036(2) 0.0380(18) 0.0262(17) 0.0019(14) -0.0084(15) -0.0145(15) C21 0.0345(19) 0.0301(17) 0.0292(18) 0.0005(13) -0.0102(15) -0.0130(14) C22 0.040(2) 0.0295(17) 0.0367(19) 0.0048(14) -0.0105(16) -0.0138(15) N1 0.0296(15) 0.0258(13) 0.0245(14) 0.0022(11) -0.0092(11) -0.0116(11) N2 0.0307(15) 0.0247(13) 0.0230(14) 0.0026(10) -0.0080(12) -0.0099(11) N3 0.0293(15) 0.0232(13) 0.0254(14) 0.0035(10) -0.0083(11) -0.0116(11) N4 0.0404(17) 0.0214(13) 0.0249(14) 0.0023(11) -0.0080(12) -0.0131(12) S1 0.0391(5) 0.0333(5) 0.0348(5) 0.0059(3) -0.0167(4) -0.0133(4) S2 0.0405(5) 0.0341(5) 0.0326(5) 0.0061(3) -0.0063(4) -0.0198(4) Cl1 0.0435(5) 0.0401(5) 0.0344(5) -0.0001(4) -0.0080(4) -0.0168(4) Cl2 0.0373(5) 0.0399(5) 0.0538(6) 0.0035(4) -0.0118(4) -0.0121(4) Cl3 0.0558(6) 0.0448(5) 0.0408(5) 0.0065(4) -0.0204(4) -0.0274(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 C1 N1 1.330(4) . ? C1 N3 1.360(4) . ? C1 C2 1.494(4) . ? C2 S1 1.670(4) . ? C2 S2 1.677(4) . ? C3 N2 1.305(4) . ? C3 N4 1.354(4) . ? C3 N3 1.392(4) . ? C4 C9 1.371(5) . ? C4 C5 1.396(5) . ? C4 N1 1.445(4) . ? C5 C6 1.394(5) . ? C5 H5A 0.9500 . ? C6 C7 1.379(5) . ? C6 H6A 0.9500 . ? C7 C8 1.391(5) . ? C7 H7A 0.9500 . ? C8 C9 1.405(5) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 C11 1.384(5) . ? C10 C15 1.395(5) . ? C10 N3 1.445(4) . ? C11 C12 1.395(5) . ? C11 H11A 0.9500 . ? C12 C13 1.392(5) . ? C12 H12A 0.9500 . ? C13 C14 1.378(5) . ? C13 H13A 0.9500 . ? C14 C15 1.399(5) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 C21 1.392(5) . ? C16 C17 1.392(5) . ? C16 N4 1.421(4) . ? C17 C18 1.390(5) . ? C17 H17A 0.9500 . ? C18 C19 1.387(5) . ? C18 H18A 0.9500 . ? C19 C20 1.378(5) . ? C19 H19A 0.9500 . ? C20 C21 1.393(5) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 Cl3 1.754(4) . ? C22 Cl2 1.772(4) . ? C22 Cl1 1.776(4) . ? C22 H22A 1.0000 . ? N1 N2 1.387(4) . ? N4 H4 0.91(4) . ? 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 N1 C1 N3 106.1(3) . . ? N1 C1 C2 129.6(3) . . ? N3 C1 C2 124.4(3) . . ? C1 C2 S1 115.4(2) . . ? C1 C2 S2 113.5(2) . . ? S1 C2 S2 131.1(2) . . ? N2 C3 N4 127.2(3) . . ? N2 C3 N3 111.2(3) . . ? N4 C3 N3 121.6(3) . . ? C9 C4 C5 121.6(3) . . ? C9 C4 N1 121.7(3) . . ? C5 C4 N1 116.6(3) . . ? C6 C5 C4 118.9(3) . . ? C6 C5 H5A 120.6 . . ? C4 C5 H5A 120.6 . . ? C7 C6 C5 120.2(3) . . ? C7 C6 H6A 119.9 . . ? C5 C6 H6A 119.9 . . ? C6 C7 C8 120.4(3) . . ? C6 C7 H7A 119.8 . . ? C8 C7 H7A 119.8 . . ? C7 C8 C9 119.9(3) . . ? C7 C8 H8A 120.0 . . ? C9 C8 H8A 120.0 . . ? C4 C9 C8 119.0(3) . . ? C4 C9 H9A 120.5 . . ? C8 C9 H9A 120.5 . . ? C11 C10 C15 122.3(3) . . ? C11 C10 N3 120.0(3) . . ? C15 C10 N3 117.7(3) . . ? C10 C11 C12 118.4(3) . . ? C10 C11 H11A 120.8 . . ? C12 C11 H11A 120.8 . . ? C13 C12 C11 120.2(3) . . ? C13 C12 H12A 119.9 . . ? C11 C12 H12A 119.9 . . ? C14 C13 C12 120.5(3) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C13 C14 C15 120.4(3) . . ? C13 C14 H14A 119.8 . . ? C15 C14 H14A 119.8 . . ? C10 C15 C14 118.1(3) . . ? C10 C15 H15A 120.9 . . ? C14 C15 H15A 120.9 . . ? C21 C16 C17 119.8(3) . . ? C21 C16 N4 117.3(3) . . ? C17 C16 N4 123.0(3) . . ? C18 C17 C16 119.3(3) . . ? C18 C17 H17A 120.4 . . ? C16 C17 H17A 120.4 . . ? C19 C18 C17 121.1(3) . . ? C19 C18 H18A 119.5 . . ? C17 C18 H18A 119.5 . . ? C20 C19 C18 119.6(3) . . ? C20 C19 H19A 120.2 . . ? C18 C19 H19A 120.2 . . ? C19 C20 C21 120.2(3) . . ? C19 C20 H20A 119.9 . . ? C21 C20 H20A 119.9 . . ? C16 C21 C20 120.2(3) . . ? C16 C21 H21A 119.9 . . ? C20 C21 H21A 119.9 . . ? Cl3 C22 Cl2 111.59(19) . . ? Cl3 C22 Cl1 110.3(2) . . ? Cl2 C22 Cl1 108.7(2) . . ? Cl3 C22 H22A 108.7 . . ? Cl2 C22 H22A 108.7 . . ? Cl1 C22 H22A 108.7 . . ? C1 N1 N2 112.0(3) . . ? C1 N1 C4 131.2(3) . . ? N2 N1 C4 116.9(2) . . ? C3 N2 N1 104.3(2) . . ? C1 N3 C3 106.6(3) . . ? C1 N3 C10 127.5(3) . . ? C3 N3 C10 126.0(3) . . ? C3 N4 C16 126.6(3) . . ? C3 N4 H4 127(2) . . ? C16 N4 H4 106(2) . . ? 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 N1 C1 C2 S1 78.0(4) . . . . ? N3 C1 C2 S1 -103.5(3) . . . . ? N1 C1 C2 S2 -102.5(4) . . . . ? N3 C1 C2 S2 76.0(4) . . . . ? C9 C4 C5 C6 1.7(5) . . . . ? N1 C4 C5 C6 -177.1(3) . . . . ? C4 C5 C6 C7 -0.8(5) . . . . ? C5 C6 C7 C8 -0.6(6) . . . . ? C6 C7 C8 C9 1.1(6) . . . . ? C5 C4 C9 C8 -1.2(5) . . . . ? N1 C4 C9 C8 177.5(3) . . . . ? C7 C8 C9 C4 -0.2(5) . . . . ? C15 C10 C11 C12 0.5(5) . . . . ? N3 C10 C11 C12 178.1(3) . . . . ? C10 C11 C12 C13 -1.3(5) . . . . ? C11 C12 C13 C14 0.3(5) . . . . ? C12 C13 C14 C15 1.3(6) . . . . ? C11 C10 C15 C14 1.1(5) . . . . ? N3 C10 C15 C14 -176.5(3) . . . . ? C13 C14 C15 C10 -2.0(5) . . . . ? C21 C16 C17 C18 -0.6(5) . . . . ? N4 C16 C17 C18 -179.1(3) . . . . ? C16 C17 C18 C19 0.0(6) . . . . ? C17 C18 C19 C20 0.3(6) . . . . ? C18 C19 C20 C21 0.0(6) . . . . ? C17 C16 C21 C20 0.9(5) . . . . ? N4 C16 C21 C20 179.4(3) . . . . ? C19 C20 C21 C16 -0.6(6) . . . . ? N3 C1 N1 N2 -0.3(4) . . . . ? C2 C1 N1 N2 178.4(3) . . . . ? N3 C1 N1 C4 177.8(3) . . . . ? C2 C1 N1 C4 -3.5(6) . . . . ? C9 C4 N1 C1 23.0(5) . . . . ? C5 C4 N1 C1 -158.2(3) . . . . ? C9 C4 N1 N2 -158.9(3) . . . . ? C5 C4 N1 N2 19.9(4) . . . . ? N4 C3 N2 N1 179.0(3) . . . . ? N3 C3 N2 N1 -1.0(4) . . . . ? C1 N1 N2 C3 0.8(4) . . . . ? C4 N1 N2 C3 -177.6(3) . . . . ? N1 C1 N3 C3 -0.3(4) . . . . ? C2 C1 N3 C3 -179.0(3) . . . . ? N1 C1 N3 C10 178.9(3) . . . . ? C2 C1 N3 C10 0.2(5) . . . . ? N2 C3 N3 C1 0.8(4) . . . . ? N4 C3 N3 C1 -179.2(3) . . . . ? N2 C3 N3 C10 -178.4(3) . . . . ? N4 C3 N3 C10 1.6(5) . . . . ? C11 C10 N3 C1 67.5(5) . . . . ? C15 C10 N3 C1 -114.8(4) . . . . ? C11 C10 N3 C3 -113.4(4) . . . . ? C15 C10 N3 C3 64.2(4) . . . . ? N2 C3 N4 C16 -8.0(6) . . . . ? N3 C3 N4 C16 172.0(3) . . . . ? C21 C16 N4 C3 176.0(3) . . . . ? C17 C16 N4 C3 -5.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.693 _refine_diff_density_min -0.574 _refine_diff_density_rms 0.104 #=====================================================================