Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Sangeeta Ray Banerjee' 'John W. Babich' 'Jon Zubieta' _journal_name_full 'Dalton Transactions' _publ_contact_author_name 'Prof Jon Zubieta' _publ_contact_author_address ; Department of Chemistry Syracuse University Syracuse New York 13244 UNITED STATES OF AMERICA ; _publ_contact_author_email JAZUBIET@SYR.EDU _publ_section_title ; Design and Synthesis of Site Directed Maleimide Bifunctional Chelators for Technetium and Rhenium. ; data_[Re(CO)3L3]Br _database_code_depnum_ccdc_archive 'CCDC 253367' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H24 N4 O5 Re, Br' _chemical_formula_sum 'C30 H24 Br N4 O5 Re' _chemical_formula_weight 786.64 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.639(2) _cell_length_b 11.829(2) _cell_length_c 13.249(3) _cell_angle_alpha 65.300(3) _cell_angle_beta 77.198(3) _cell_angle_gamma 72.582(3) _cell_volume 1571.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 96(2) _cell_measurement_reflns_used 10184 _cell_measurement_theta_min 1.70 _cell_measurement_theta_max 31.50 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 5.181 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.4239 _exptl_absorpt_correction_T_max 0.5104 _exptl_absorpt_process_details 'SADABS SHELX-97 (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 96(2) _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'APEX CCD area dectector' _diffrn_measurement_method 'Phi & omega Scan' _diffrn_detector_area_resol_mean 514 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 20227 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0623 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 31.50 _reflns_number_total 10184 _reflns_number_gt 8686 _reflns_threshold_expression I>2\s(I)) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0834P)^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 10184 _refine_ls_number_parameters 372 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1299 _refine_ls_wR_factor_gt 0.1260 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 Re1 Re 0.183201(15) 0.802650(16) 0.190911(14) 0.01755(6) Uani 1 1 d . . . Br1 Br 0.48252(5) 0.68735(6) 0.56891(5) 0.03523(13) Uani 1 1 d . . . O1 O 0.2779(4) 0.9412(4) -0.0529(3) 0.0301(8) Uani 1 1 d . . . O2 O -0.0523(4) 0.8368(4) 0.1021(3) 0.0321(8) Uani 1 1 d . . . O3 O 0.2566(4) 0.5581(4) 0.1405(4) 0.0379(10) Uani 1 1 d . . . O4 O 0.8894(4) 0.5680(4) 0.1205(4) 0.0370(9) Uani 1 1 d . . . O5 O 0.6002(4) 0.8946(4) -0.0754(4) 0.0380(10) Uani 1 1 d . . . N1 N 0.3547(4) 0.7640(4) 0.2591(3) 0.0217(8) Uani 1 1 d . . . N2 N 0.1460(4) 0.6925(4) 0.3731(3) 0.0193(7) Uani 1 1 d . . . N3 N 0.1449(4) 0.9598(4) 0.2525(3) 0.0204(7) Uani 1 1 d . . . N4 N 0.7275(4) 0.7342(4) 0.0502(4) 0.0259(9) Uani 1 1 d . . . C1 C 0.2399(4) 0.8930(4) 0.0393(4) 0.0210(9) Uani 1 1 d . . . C2 C 0.0336(4) 0.8258(5) 0.1374(4) 0.0207(8) Uani 1 1 d . . . C3 C 0.2309(5) 0.6495(5) 0.1583(4) 0.0248(9) Uani 1 1 d . . . C4 C 0.2474(4) 0.6228(4) 0.4216(4) 0.0209(9) Uani 1 1 d . . . C5 C 0.2485(5) 0.5400(5) 0.5345(4) 0.0244(9) Uani 1 1 d . . . H5 H 0.3232 0.4939 0.5649 0.029 Uiso 1 1 calc R . . C6 C 0.1413(5) 0.5266(5) 0.6001(4) 0.0248(9) Uani 1 1 d . . . H6 H 0.1403 0.4695 0.6762 0.030 Uiso 1 1 calc R . . C7 C 0.0317(5) 0.5990(5) 0.5533(4) 0.0231(9) Uani 1 1 d . . . C8 C -0.0824(5) 0.5897(5) 0.6196(4) 0.0278(10) Uani 1 1 d . . . H8 H -0.0852 0.5327 0.6957 0.033 Uiso 1 1 calc R . . C9 C -0.1874(5) 0.6622(5) 0.5742(5) 0.0288(11) Uani 1 1 d . . . H9 H -0.2631 0.6559 0.6187 0.035 Uiso 1 1 calc R . . C10 C -0.1838(5) 0.7460(5) 0.4621(4) 0.0269(10) Uani 1 1 d . . . H10 H -0.2576 0.7952 0.4311 0.032 Uiso 1 1 calc R . . C11 C -0.0750(4) 0.7585(5) 0.3954(4) 0.0231(9) Uani 1 1 d . . . H11 H -0.0745 0.8177 0.3201 0.028 Uiso 1 1 calc R . . C12 C 0.0359(4) 0.6832(4) 0.4395(4) 0.0194(8) Uani 1 1 d . . . C13 C 0.3661(4) 0.6342(5) 0.3495(4) 0.0239(9) Uani 1 1 d . . . H13A H 0.4293 0.6189 0.3959 0.029 Uiso 1 1 calc R . . H13B H 0.3910 0.5686 0.3160 0.029 Uiso 1 1 calc R . . C14 C 0.3482(5) 0.8609(5) 0.3061(4) 0.0271(10) Uani 1 1 d . . . H14A H 0.3785 0.8158 0.3804 0.033 Uiso 1 1 calc R . . H14B H 0.4028 0.9173 0.2570 0.033 Uiso 1 1 calc R . . C15 C 0.2258(4) 0.9409(5) 0.3182(4) 0.0236(9) Uani 1 1 d . . . C16 C 0.2019(5) 1.0034(6) 0.3953(5) 0.0303(11) Uani 1 1 d . . . H16 H 0.2619 0.9892 0.4403 0.036 Uiso 1 1 calc R . . C17 C 0.0905(6) 1.0842(6) 0.4030(5) 0.0336(12) Uani 1 1 d . . . H17 H 0.0706 1.1204 0.4583 0.040 Uiso 1 1 calc R . . C18 C 0.0060(5) 1.1136(5) 0.3298(5) 0.0266(10) Uani 1 1 d . . . C19 C -0.1062(6) 1.2023(6) 0.3284(6) 0.0379(13) Uani 1 1 d . . . H19 H -0.1286 1.2405 0.3825 0.046 Uiso 1 1 calc R . . C20 C -0.1836(6) 1.2350(6) 0.2523(7) 0.0430(15) Uani 1 1 d . . . H20 H -0.2592 1.2945 0.2535 0.052 Uiso 1 1 calc R . . C21 C -0.1494(6) 1.1789(6) 0.1712(6) 0.0383(14) Uani 1 1 d . . . H21 H -0.2011 1.2042 0.1154 0.046 Uiso 1 1 calc R . . C22 C -0.0434(5) 1.0890(5) 0.1719(5) 0.0280(10) Uani 1 1 d . . . H22 H -0.0229 1.0514 0.1175 0.034 Uiso 1 1 calc R . . C23 C 0.0354(4) 1.0517(4) 0.2518(4) 0.0221(9) Uani 1 1 d . . . C24 C 0.4656(4) 0.7609(5) 0.1740(4) 0.0268(10) Uani 1 1 d . . . H24A H 0.4622 0.8481 0.1163 0.032 Uiso 1 1 calc R . . H24B H 0.4642 0.7044 0.1366 0.032 Uiso 1 1 calc R . . C25 C 0.5853(4) 0.7129(5) 0.2263(4) 0.0268(10) Uani 1 1 d . . . H25A H 0.5718 0.7338 0.2937 0.032 Uiso 1 1 calc R . . H25B H 0.6111 0.6187 0.2501 0.032 Uiso 1 1 calc R . . C26 C 0.6859(5) 0.7724(5) 0.1453(4) 0.0271(10) Uani 1 1 d . . . H26A H 0.6567 0.8666 0.1174 0.033 Uiso 1 1 calc R . . H26B H 0.7558 0.7493 0.1869 0.033 Uiso 1 1 calc R . . C27 C 0.8280(5) 0.6375(5) 0.0446(5) 0.0286(10) Uani 1 1 d . . . C28 C 0.8441(6) 0.6386(6) -0.0711(5) 0.0363(13) Uani 1 1 d . . . H28 H 0.9057 0.5826 -0.0998 0.044 Uiso 1 1 calc R . . C29 C 0.7564(6) 0.7323(6) -0.1269(5) 0.0365(13) Uani 1 1 d . . . H29 H 0.7440 0.7523 -0.2016 0.044 Uiso 1 1 calc R . . C30 C 0.6818(5) 0.8000(5) -0.0536(5) 0.0293(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 Re1 0.01310(9) 0.01775(9) 0.01889(9) -0.00378(6) -0.00523(6) -0.00163(6) Br1 0.0275(3) 0.0374(3) 0.0431(3) -0.0201(2) -0.0186(2) 0.0071(2) O1 0.031(2) 0.0317(19) 0.0240(17) -0.0042(15) -0.0035(15) -0.0117(16) O2 0.0206(18) 0.040(2) 0.036(2) -0.0138(17) -0.0076(15) -0.0060(16) O3 0.033(2) 0.035(2) 0.046(2) -0.0200(19) 0.0023(19) -0.0067(18) O4 0.030(2) 0.037(2) 0.035(2) -0.0101(18) -0.0109(17) 0.0052(17) O5 0.036(2) 0.028(2) 0.037(2) -0.0023(17) -0.0118(18) 0.0023(17) N1 0.0176(18) 0.0211(18) 0.0203(17) -0.0010(14) -0.0065(14) -0.0029(14) N2 0.0161(17) 0.0200(18) 0.0220(17) -0.0065(14) -0.0065(14) -0.0031(14) N3 0.0174(18) 0.0232(19) 0.0196(17) -0.0067(15) -0.0050(14) -0.0036(14) N4 0.020(2) 0.028(2) 0.0245(19) -0.0062(16) -0.0045(16) -0.0010(16) C1 0.018(2) 0.0177(19) 0.028(2) -0.0070(17) -0.0088(17) -0.0030(15) C2 0.018(2) 0.025(2) 0.022(2) -0.0078(17) -0.0040(16) -0.0085(17) C3 0.021(2) 0.025(2) 0.025(2) -0.0080(18) -0.0002(18) -0.0049(18) C4 0.017(2) 0.020(2) 0.025(2) -0.0073(17) -0.0044(17) -0.0038(16) C5 0.024(2) 0.023(2) 0.022(2) -0.0049(17) -0.0065(18) -0.0034(18) C6 0.027(2) 0.024(2) 0.023(2) -0.0052(18) -0.0033(18) -0.0089(18) C7 0.022(2) 0.023(2) 0.025(2) -0.0073(18) -0.0031(17) -0.0084(17) C8 0.025(3) 0.035(3) 0.025(2) -0.013(2) 0.0015(19) -0.010(2) C9 0.024(2) 0.036(3) 0.030(2) -0.016(2) 0.004(2) -0.010(2) C10 0.020(2) 0.035(3) 0.029(2) -0.015(2) -0.0004(18) -0.0071(19) C11 0.016(2) 0.028(2) 0.027(2) -0.0104(19) -0.0062(17) -0.0043(17) C12 0.017(2) 0.020(2) 0.023(2) -0.0104(17) -0.0012(16) -0.0049(16) C13 0.015(2) 0.021(2) 0.026(2) -0.0008(18) -0.0058(17) -0.0011(16) C14 0.021(2) 0.026(2) 0.030(2) -0.0026(19) -0.0102(19) -0.0062(18) C15 0.020(2) 0.023(2) 0.028(2) -0.0048(18) -0.0115(18) -0.0048(17) C16 0.027(3) 0.038(3) 0.034(3) -0.016(2) -0.009(2) -0.011(2) C17 0.036(3) 0.037(3) 0.037(3) -0.019(2) -0.007(2) -0.011(2) C18 0.024(2) 0.027(2) 0.034(3) -0.018(2) -0.002(2) -0.0064(19) C19 0.033(3) 0.036(3) 0.055(4) -0.030(3) -0.008(3) -0.002(2) C20 0.031(3) 0.038(3) 0.065(4) -0.033(3) -0.014(3) 0.012(2) C21 0.032(3) 0.030(3) 0.056(4) -0.023(3) -0.022(3) 0.009(2) C22 0.026(2) 0.024(2) 0.033(3) -0.012(2) -0.010(2) 0.0037(19) C23 0.020(2) 0.018(2) 0.028(2) -0.0080(17) -0.0078(17) -0.0018(16) C24 0.014(2) 0.033(3) 0.023(2) -0.0016(19) -0.0036(17) -0.0033(18) C25 0.015(2) 0.035(3) 0.026(2) -0.007(2) -0.0057(17) -0.0054(18) C26 0.019(2) 0.032(3) 0.031(2) -0.011(2) -0.0059(19) -0.0068(19) C27 0.026(3) 0.025(2) 0.030(2) -0.008(2) -0.007(2) -0.0001(19) C28 0.038(3) 0.041(3) 0.028(3) -0.017(2) -0.001(2) -0.002(2) C29 0.037(3) 0.038(3) 0.029(3) -0.009(2) -0.008(2) -0.005(2) C30 0.024(2) 0.028(2) 0.030(2) -0.002(2) -0.009(2) -0.0067(19) _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 Re1 C1 1.911(5) . ? Re1 C2 1.925(5) . ? Re1 C3 1.930(5) . ? Re1 N1 2.217(4) . ? Re1 N3 2.220(4) . ? Re1 N2 2.226(4) . ? O1 C1 1.159(6) . ? O2 C2 1.146(6) . ? O3 C3 1.141(7) . ? O4 C27 1.213(6) . ? O5 C30 1.205(7) . ? N1 C13 1.491(6) . ? N1 C14 1.494(7) . ? N1 C24 1.516(6) . ? N2 C4 1.340(6) . ? N2 C12 1.391(6) . ? N3 C15 1.331(6) . ? N3 C23 1.404(6) . ? N4 C27 1.383(7) . ? N4 C30 1.400(7) . ? N4 C26 1.450(7) . ? C4 C5 1.404(7) . ? C4 C13 1.503(7) . ? C5 C6 1.364(7) . ? C5 H5 0.9500 . ? C6 C7 1.413(7) . ? C6 H6 0.9500 . ? C7 C12 1.418(7) . ? C7 C8 1.427(7) . ? C8 C9 1.363(8) . ? C8 H8 0.9500 . ? C9 C10 1.398(8) . ? C9 H9 0.9500 . ? C10 C11 1.384(7) . ? C10 H10 0.9500 . ? C11 C12 1.418(7) . ? C11 H11 0.9500 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.473(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.431(8) . ? C16 C17 1.373(8) . ? C16 H16 0.9500 . ? C17 C18 1.401(8) . ? C17 H17 0.9500 . ? C18 C19 1.407(8) . ? C18 C23 1.430(7) . ? C19 C20 1.358(9) . ? C19 H19 0.9500 . ? C20 C21 1.415(9) . ? C20 H20 0.9500 . ? C21 C22 1.366(7) . ? C21 H21 0.9500 . ? C22 C23 1.398(7) . ? C22 H22 0.9500 . ? C24 C25 1.539(7) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.523(7) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.498(8) . ? C28 C29 1.337(9) . ? C28 H28 0.9500 . ? C29 C30 1.483(9) . ? C29 H29 0.9500 . ? 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 Re1 C2 87.1(2) . . ? C1 Re1 C3 87.9(2) . . ? C2 Re1 C3 83.8(2) . . ? C1 Re1 N1 95.48(17) . . ? C2 Re1 N1 176.57(17) . . ? C3 Re1 N1 93.93(19) . . ? C1 Re1 N3 98.10(18) . . ? C2 Re1 N3 103.51(18) . . ? C3 Re1 N3 170.67(18) . . ? N1 Re1 N3 78.45(16) . . ? C1 Re1 N2 171.15(17) . . ? C2 Re1 N2 101.74(17) . . ? C3 Re1 N2 92.13(18) . . ? N1 Re1 N2 75.69(14) . . ? N3 Re1 N2 80.84(15) . . ? C13 N1 C14 110.2(4) . . ? C13 N1 C24 108.1(4) . . ? C14 N1 C24 109.4(4) . . ? C13 N1 Re1 105.1(3) . . ? C14 N1 Re1 110.5(3) . . ? C24 N1 Re1 113.5(3) . . ? C4 N2 C12 117.6(4) . . ? C4 N2 Re1 112.7(3) . . ? C12 N2 Re1 129.7(3) . . ? C15 N3 C23 119.1(4) . . ? C15 N3 Re1 112.1(3) . . ? C23 N3 Re1 126.7(3) . . ? C27 N4 C30 110.2(5) . . ? C27 N4 C26 124.4(4) . . ? C30 N4 C26 124.8(5) . . ? O1 C1 Re1 176.1(4) . . ? O2 C2 Re1 176.7(5) . . ? O3 C3 Re1 178.3(5) . . ? N2 C4 C5 123.9(5) . . ? N2 C4 C13 117.3(4) . . ? C5 C4 C13 118.8(4) . . ? C6 C5 C4 119.3(5) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C7 119.0(5) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C6 C7 C12 119.3(4) . . ? C6 C7 C8 120.8(5) . . ? C12 C7 C8 119.9(5) . . ? C9 C8 C7 120.3(5) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 120.1(5) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 121.3(5) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 120.0(5) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? N2 C12 C11 120.9(4) . . ? N2 C12 C7 120.8(4) . . ? C11 C12 C7 118.3(4) . . ? N1 C13 C4 110.4(4) . . ? N1 C13 H13A 109.6 . . ? C4 C13 H13A 109.6 . . ? N1 C13 H13B 109.6 . . ? C4 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? C15 C14 N1 114.3(4) . . ? C15 C14 H14A 108.7 . . ? N1 C14 H14A 108.7 . . ? C15 C14 H14B 108.7 . . ? N1 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? N3 C15 C16 122.5(5) . . ? N3 C15 C14 119.5(5) . . ? C16 C15 C14 117.9(5) . . ? C17 C16 C15 118.7(5) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C16 C17 C18 120.5(5) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C17 C18 C19 123.2(5) . . ? C17 C18 C23 118.6(5) . . ? C19 C18 C23 118.2(5) . . ? C20 C19 C18 122.2(6) . . ? C20 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? C19 C20 C21 118.8(5) . . ? C19 C20 H20 120.6 . . ? C21 C20 H20 120.6 . . ? C22 C21 C20 121.1(6) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C21 C22 C23 120.7(5) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C22 C23 N3 120.9(4) . . ? C22 C23 C18 118.9(5) . . ? N3 C23 C18 120.1(4) . . ? N1 C24 C25 113.0(4) . . ? N1 C24 H24A 109.0 . . ? C25 C24 H24A 109.0 . . ? N1 C24 H24B 109.0 . . ? C25 C24 H24B 109.0 . . ? H24A C24 H24B 107.8 . . ? C26 C25 C24 112.3(4) . . ? C26 C25 H25A 109.1 . . ? C24 C25 H25A 109.1 . . ? C26 C25 H25B 109.1 . . ? C24 C25 H25B 109.1 . . ? H25A C25 H25B 107.9 . . ? N4 C26 C25 115.0(5) . . ? N4 C26 H26A 108.5 . . ? C25 C26 H26A 108.5 . . ? N4 C26 H26B 108.5 . . ? C25 C26 H26B 108.5 . . ? H26A C26 H26B 107.5 . . ? O4 C27 N4 125.0(5) . . ? O4 C27 C28 128.4(5) . . ? N4 C27 C28 106.5(5) . . ? C29 C28 C27 107.9(5) . . ? C29 C28 H28 126.0 . . ? C27 C28 H28 126.0 . . ? C28 C29 C30 109.1(5) . . ? C28 C29 H29 125.5 . . ? C30 C29 H29 125.5 . . ? O5 C30 N4 124.6(6) . . ? O5 C30 C29 129.3(5) . . ? N4 C30 C29 106.1(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 C1 Re1 N1 C13 -143.8(3) . . . . ? C2 Re1 N1 C13 -6(3) . . . . ? C3 Re1 N1 C13 -55.6(3) . . . . ? N3 Re1 N1 C13 119.0(3) . . . . ? N2 Re1 N1 C13 35.6(3) . . . . ? C1 Re1 N1 C14 97.3(3) . . . . ? C2 Re1 N1 C14 -125(3) . . . . ? C3 Re1 N1 C14 -174.4(3) . . . . ? N3 Re1 N1 C14 0.1(3) . . . . ? N2 Re1 N1 C14 -83.3(3) . . . . ? C1 Re1 N1 C24 -25.9(4) . . . . ? C2 Re1 N1 C24 112(3) . . . . ? C3 Re1 N1 C24 62.3(4) . . . . ? N3 Re1 N1 C24 -123.1(3) . . . . ? N2 Re1 N1 C24 153.5(4) . . . . ? C1 Re1 N2 C4 -18.6(13) . . . . ? C2 Re1 N2 C4 155.5(3) . . . . ? C3 Re1 N2 C4 71.4(4) . . . . ? N1 Re1 N2 C4 -22.1(3) . . . . ? N3 Re1 N2 C4 -102.4(3) . . . . ? C1 Re1 N2 C12 164.0(10) . . . . ? C2 Re1 N2 C12 -21.8(4) . . . . ? C3 Re1 N2 C12 -106.0(4) . . . . ? N1 Re1 N2 C12 160.5(4) . . . . ? N3 Re1 N2 C12 80.2(4) . . . . ? C1 Re1 N3 C15 -107.2(4) . . . . ? C2 Re1 N3 C15 163.9(3) . . . . ? C3 Re1 N3 C15 22.5(12) . . . . ? N1 Re1 N3 C15 -13.2(3) . . . . ? N2 Re1 N3 C15 64.0(3) . . . . ? C1 Re1 N3 C23 89.4(4) . . . . ? C2 Re1 N3 C23 0.5(4) . . . . ? C3 Re1 N3 C23 -140.9(10) . . . . ? N1 Re1 N3 C23 -176.6(4) . . . . ? N2 Re1 N3 C23 -99.5(4) . . . . ? C2 Re1 C1 O1 -101(6) . . . . ? C3 Re1 C1 O1 -17(6) . . . . ? N1 Re1 C1 O1 77(6) . . . . ? N3 Re1 C1 O1 156(6) . . . . ? N2 Re1 C1 O1 73(7) . . . . ? C1 Re1 C2 O2 56(8) . . . . ? C3 Re1 C2 O2 -32(8) . . . . ? N1 Re1 C2 O2 -82(9) . . . . ? N3 Re1 C2 O2 154(8) . . . . ? N2 Re1 C2 O2 -123(8) . . . . ? C1 Re1 C3 O3 -139(17) . . . . ? C2 Re1 C3 O3 -52(17) . . . . ? N1 Re1 C3 O3 126(17) . . . . ? N3 Re1 C3 O3 91(17) . . . . ? N2 Re1 C3 O3 50(17) . . . . ? C12 N2 C4 C5 1.0(7) . . . . ? Re1 N2 C4 C5 -176.8(4) . . . . ? C12 N2 C4 C13 -179.5(4) . . . . ? Re1 N2 C4 C13 2.8(5) . . . . ? N2 C4 C5 C6 1.0(8) . . . . ? C13 C4 C5 C6 -178.5(5) . . . . ? C4 C5 C6 C7 -1.6(8) . . . . ? C5 C6 C7 C12 0.3(8) . . . . ? C5 C6 C7 C8 -178.8(5) . . . . ? C6 C7 C8 C9 178.5(5) . . . . ? C12 C7 C8 C9 -0.6(8) . . . . ? C7 C8 C9 C10 0.2(8) . . . . ? C8 C9 C10 C11 -0.8(9) . . . . ? C9 C10 C11 C12 1.7(8) . . . . ? C4 N2 C12 C11 177.0(4) . . . . ? Re1 N2 C12 C11 -5.7(7) . . . . ? C4 N2 C12 C7 -2.3(7) . . . . ? Re1 N2 C12 C7 174.9(3) . . . . ? C10 C11 C12 N2 178.6(5) . . . . ? C10 C11 C12 C7 -2.0(7) . . . . ? C6 C7 C12 N2 1.8(7) . . . . ? C8 C7 C12 N2 -179.2(5) . . . . ? C6 C7 C12 C11 -177.6(5) . . . . ? C8 C7 C12 C11 1.5(7) . . . . ? C14 N1 C13 C4 73.5(5) . . . . ? C24 N1 C13 C4 -167.0(4) . . . . ? Re1 N1 C13 C4 -45.5(5) . . . . ? N2 C4 C13 N1 29.9(6) . . . . ? C5 C4 C13 N1 -150.6(5) . . . . ? C13 N1 C14 C15 -103.8(5) . . . . ? C24 N1 C14 C15 137.5(4) . . . . ? Re1 N1 C14 C15 11.9(5) . . . . ? C23 N3 C15 C16 5.2(7) . . . . ? Re1 N3 C15 C16 -159.6(4) . . . . ? C23 N3 C15 C14 -170.0(4) . . . . ? Re1 N3 C15 C14 25.2(6) . . . . ? N1 C14 C15 N3 -25.7(7) . . . . ? N1 C14 C15 C16 158.9(4) . . . . ? N3 C15 C16 C17 1.1(8) . . . . ? C14 C15 C16 C17 176.3(5) . . . . ? C15 C16 C17 C18 -5.6(9) . . . . ? C16 C17 C18 C19 -175.6(6) . . . . ? C16 C17 C18 C23 3.8(8) . . . . ? C17 C18 C19 C20 176.0(7) . . . . ? C23 C18 C19 C20 -3.4(9) . . . . ? C18 C19 C20 C21 -0.6(11) . . . . ? C19 C20 C21 C22 3.0(11) . . . . ? C20 C21 C22 C23 -1.2(10) . . . . ? C21 C22 C23 N3 -179.7(5) . . . . ? C21 C22 C23 C18 -2.9(8) . . . . ? C15 N3 C23 C22 169.8(5) . . . . ? Re1 N3 C23 C22 -27.8(7) . . . . ? C15 N3 C23 C18 -6.9(7) . . . . ? Re1 N3 C23 C18 155.5(4) . . . . ? C17 C18 C23 C22 -174.3(5) . . . . ? C19 C18 C23 C22 5.1(8) . . . . ? C17 C18 C23 N3 2.5(8) . . . . ? C19 C18 C23 N3 -178.1(5) . . . . ? C13 N1 C24 C25 -54.6(6) . . . . ? C14 N1 C24 C25 65.4(5) . . . . ? Re1 N1 C24 C25 -170.7(4) . . . . ? N1 C24 C25 C26 -149.6(5) . . . . ? C27 N4 C26 C25 -96.6(6) . . . . ? C30 N4 C26 C25 92.2(6) . . . . ? C24 C25 C26 N4 -67.4(6) . . . . ? C30 N4 C27 O4 176.9(6) . . . . ? C26 N4 C27 O4 4.6(9) . . . . ? C30 N4 C27 C28 -2.6(6) . . . . ? C26 N4 C27 C28 -174.9(5) . . . . ? O4 C27 C28 C29 -179.3(7) . . . . ? N4 C27 C28 C29 0.3(7) . . . . ? C27 C28 C29 C30 2.0(7) . . . . ? C27 N4 C30 O5 -174.3(6) . . . . ? C26 N4 C30 O5 -2.0(9) . . . . ? C27 N4 C30 C29 3.8(6) . . . . ? C26 N4 C30 C29 176.1(5) . . . . ? C28 C29 C30 O5 174.3(6) . . . . ? C28 C29 C30 N4 -3.6(7) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 31.50 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 1.250 _refine_diff_density_min -1.664 _refine_diff_density_rms 0.257 data_[Re(CO)3L3]Br _database_code_depnum_ccdc_archive 'CCDC 258469' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'Ligand Hydrochloride' _chemical_melting_point ? _chemical_formula_moiety 'C26 H22 N4 O2, C H Cl3' _chemical_formula_sum 'C27 H23 Cl3 N4 O2' _chemical_formula_weight 541.84 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2492(8) _cell_length_b 11.1750(10) _cell_length_c 13.0963(11) _cell_angle_alpha 101.983(2) _cell_angle_beta 90.707(2) _cell_angle_gamma 101.991(2) _cell_volume 1293.06(19) _cell_formula_units_Z 2 _cell_measurement_temperature 96(2) _cell_measurement_reflns_used 8452 _cell_measurement_theta_min 1.91 _cell_measurement_theta_max 31.50 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.387 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.8862 _exptl_absorpt_correction_T_max 0.9623 _exptl_absorpt_process_details 'SADABS SHELX-97 (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 96(2) _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'APEX CCD area dectector' _diffrn_measurement_method 'Phi & omega Scan' _diffrn_detector_area_resol_mean 512 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16987 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 31.50 _reflns_number_total 8452 _reflns_number_gt 7216 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0553P)^2^+0.8592P] 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 8452 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1250 _refine_ls_wR_factor_gt 0.1188 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 Cl1 Cl 0.83557(4) 0.29650(3) 0.22181(3) 0.02681(9) Uani 1 1 d . . . Cl3 Cl 0.71287(5) 0.06102(4) 0.28026(3) 0.03281(10) Uani 1 1 d . . . Cl2 Cl 0.54306(6) 0.15938(6) 0.14405(7) 0.0716(2) Uani 1 1 d . . . O1 O -0.08990(14) 0.87847(11) 0.35890(9) 0.0280(2) Uani 1 1 d . . . O2 O 0.07381(14) 0.52329(10) 0.36855(9) 0.0269(2) Uani 1 1 d . . . N1 N 0.16074(13) 0.78312(11) 0.16661(9) 0.0167(2) Uani 1 1 d . . . N3 N 0.19614(13) 1.02201(11) 0.02672(9) 0.0170(2) Uani 1 1 d . . . N2 N 0.46055(13) 0.68365(11) 0.24728(9) 0.0184(2) Uani 1 1 d . . . N4 N -0.01614(13) 0.68958(11) 0.33409(9) 0.0179(2) Uani 1 1 d . . . C1 C 0.39061(15) 0.77654(13) 0.25758(11) 0.0181(2) Uani 1 1 d . . . C2 C 0.37669(17) 0.85487(14) 0.35572(12) 0.0228(3) Uani 1 1 d . . . H2 H 0.3235 0.9197 0.3599 0.027 Uiso 1 1 calc R . . C3 C 0.44042(17) 0.83592(15) 0.44371(12) 0.0246(3) Uani 1 1 d . . . H3 H 0.4323 0.8878 0.5098 0.030 Uiso 1 1 calc R . . C4 C 0.51883(16) 0.73843(14) 0.43613(11) 0.0214(3) Uani 1 1 d . . . C5 C 0.59008(18) 0.71267(16) 0.52314(13) 0.0278(3) Uani 1 1 d . . . H5 H 0.5875 0.7630 0.5909 0.033 Uiso 1 1 calc R . . C6 C 0.66252(18) 0.61594(17) 0.51029(14) 0.0301(3) Uani 1 1 d . . . H6 H 0.7108 0.6000 0.5689 0.036 Uiso 1 1 calc R . . C7 C 0.66562(17) 0.54011(16) 0.41058(14) 0.0282(3) Uani 1 1 d . . . H7 H 0.7150 0.4724 0.4026 0.034 Uiso 1 1 calc R . . C8 C 0.59826(16) 0.56263(15) 0.32469(12) 0.0238(3) Uani 1 1 d . . . H8 H 0.6011 0.5105 0.2578 0.029 Uiso 1 1 calc R . . C9 C 0.52457(15) 0.66325(13) 0.33547(11) 0.0191(2) Uani 1 1 d . . . C10 C 0.32158(15) 0.79787(13) 0.15986(11) 0.0194(2) Uani 1 1 d . . . H10A H 0.3653 0.8833 0.1504 0.023 Uiso 1 1 calc R . . H10B H 0.3429 0.7371 0.0984 0.023 Uiso 1 1 calc R . . C11 C 0.09655(16) 0.83166(13) 0.08513(11) 0.0201(3) Uani 1 1 d . . . H11A H -0.0127 0.8049 0.0825 0.024 Uiso 1 1 calc R . . H11B H 0.1306 0.7954 0.0165 0.024 Uiso 1 1 calc R . . C12 C 0.13885(15) 0.97234(13) 0.10402(11) 0.0176(2) Uani 1 1 d . . . C13 C 0.11274(17) 1.04468(14) 0.20183(12) 0.0225(3) Uani 1 1 d . . . H13 H 0.0710 1.0048 0.2553 0.027 Uiso 1 1 calc R . . C14 C 0.14827(17) 1.17217(14) 0.21825(11) 0.0226(3) Uani 1 1 d . . . H14 H 0.1313 1.2220 0.2833 0.027 Uiso 1 1 calc R . . C15 C 0.21077(15) 1.22978(13) 0.13758(11) 0.0186(2) Uani 1 1 d . . . C16 C 0.25379(18) 1.36126(14) 0.14881(12) 0.0231(3) Uani 1 1 d . . . H16 H 0.2384 1.4152 0.2122 0.028 Uiso 1 1 calc R . . C17 C 0.31745(17) 1.41118(13) 0.06876(12) 0.0230(3) Uani 1 1 d . . . H17 H 0.3464 1.4995 0.0771 0.028 Uiso 1 1 calc R . . C18 C 0.34031(15) 1.33228(13) -0.02590(11) 0.0201(3) Uani 1 1 d . . . H18 H 0.3845 1.3678 -0.0809 0.024 Uiso 1 1 calc R . . C19 C 0.29914(15) 1.20443(13) -0.03905(11) 0.0182(2) Uani 1 1 d . . . H19 H 0.3150 1.1520 -0.1031 0.022 Uiso 1 1 calc R . . C20 C 0.23314(14) 1.15038(12) 0.04228(10) 0.0160(2) Uani 1 1 d . . . C21 C 0.08716(16) 0.65240(12) 0.16133(11) 0.0188(2) Uani 1 1 d . . . H21A H 0.1561 0.6092 0.1902 0.023 Uiso 1 1 calc R . . H21B H 0.0608 0.6096 0.0874 0.023 Uiso 1 1 calc R . . C22 C -0.05243(15) 0.64366(13) 0.22257(11) 0.0189(2) Uani 1 1 d . . . H22A H -0.1172 0.6936 0.1982 0.023 Uiso 1 1 calc R . . H22B H -0.1074 0.5554 0.2094 0.023 Uiso 1 1 calc R . . C23 C -0.03571(16) 0.80335(13) 0.39218(11) 0.0203(3) Uani 1 1 d . . . C24 C 0.02198(18) 0.81263(14) 0.50112(12) 0.0239(3) Uani 1 1 d . . . H24 H 0.0249 0.8811 0.5585 0.029 Uiso 1 1 calc R . . C25 C 0.06864(18) 0.70853(15) 0.50397(11) 0.0241(3) Uani 1 1 d . . . H25 H 0.1098 0.6898 0.5641 0.029 Uiso 1 1 calc R . . C26 C 0.04571(16) 0.62582(13) 0.39723(11) 0.0199(3) Uani 1 1 d . . . C27 C 0.71945(16) 0.14624(14) 0.18105(11) 0.0213(3) Uani 1 1 d . . . H27 H 0.7616 0.1001 0.1188 0.026 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.03298(19) 0.01942(16) 0.02592(18) 0.00382(13) -0.00012(14) 0.00207(13) Cl3 0.0494(2) 0.02519(18) 0.02052(17) 0.00699(14) 0.00059(15) -0.00130(16) Cl2 0.0293(2) 0.0620(4) 0.1279(7) 0.0379(4) -0.0312(3) 0.0042(2) O1 0.0344(6) 0.0254(5) 0.0300(6) 0.0113(5) 0.0060(5) 0.0140(5) O2 0.0365(6) 0.0201(5) 0.0268(5) 0.0076(4) 0.0011(4) 0.0098(4) N1 0.0183(5) 0.0154(5) 0.0177(5) 0.0068(4) 0.0012(4) 0.0034(4) N3 0.0183(5) 0.0169(5) 0.0166(5) 0.0054(4) -0.0007(4) 0.0040(4) N2 0.0183(5) 0.0192(5) 0.0184(5) 0.0051(4) 0.0031(4) 0.0046(4) N4 0.0211(5) 0.0170(5) 0.0169(5) 0.0063(4) 0.0009(4) 0.0040(4) C1 0.0173(6) 0.0172(6) 0.0202(6) 0.0054(5) 0.0025(5) 0.0029(5) C2 0.0248(7) 0.0201(6) 0.0234(7) 0.0016(5) 0.0027(5) 0.0074(5) C3 0.0272(7) 0.0233(7) 0.0206(7) -0.0008(5) 0.0012(5) 0.0046(5) C4 0.0193(6) 0.0235(6) 0.0200(6) 0.0056(5) 0.0001(5) 0.0009(5) C5 0.0262(7) 0.0340(8) 0.0215(7) 0.0081(6) -0.0020(5) 0.0006(6) C6 0.0228(7) 0.0387(9) 0.0311(8) 0.0177(7) -0.0038(6) 0.0020(6) C7 0.0221(7) 0.0317(8) 0.0364(9) 0.0176(7) 0.0034(6) 0.0079(6) C8 0.0222(6) 0.0265(7) 0.0262(7) 0.0103(6) 0.0052(5) 0.0083(5) C9 0.0159(5) 0.0211(6) 0.0206(6) 0.0063(5) 0.0022(5) 0.0029(5) C10 0.0190(6) 0.0215(6) 0.0199(6) 0.0077(5) 0.0041(5) 0.0057(5) C11 0.0230(6) 0.0178(6) 0.0200(6) 0.0077(5) -0.0019(5) 0.0019(5) C12 0.0174(6) 0.0183(6) 0.0190(6) 0.0072(5) 0.0000(4) 0.0049(5) C13 0.0281(7) 0.0235(7) 0.0206(6) 0.0103(5) 0.0071(5) 0.0104(5) C14 0.0299(7) 0.0238(7) 0.0187(6) 0.0072(5) 0.0079(5) 0.0127(6) C15 0.0204(6) 0.0191(6) 0.0188(6) 0.0061(5) 0.0032(5) 0.0077(5) C16 0.0309(7) 0.0180(6) 0.0220(7) 0.0035(5) 0.0048(5) 0.0094(5) C17 0.0263(7) 0.0162(6) 0.0274(7) 0.0056(5) 0.0034(5) 0.0052(5) C18 0.0204(6) 0.0197(6) 0.0214(6) 0.0074(5) 0.0036(5) 0.0039(5) C19 0.0197(6) 0.0192(6) 0.0168(6) 0.0055(5) 0.0029(4) 0.0048(5) C20 0.0153(5) 0.0179(6) 0.0159(6) 0.0051(4) 0.0004(4) 0.0050(4) C21 0.0240(6) 0.0141(5) 0.0181(6) 0.0039(5) 0.0016(5) 0.0031(5) C22 0.0203(6) 0.0181(6) 0.0171(6) 0.0057(5) -0.0009(5) -0.0001(5) C23 0.0221(6) 0.0195(6) 0.0208(6) 0.0067(5) 0.0050(5) 0.0050(5) C24 0.0305(7) 0.0220(6) 0.0189(6) 0.0036(5) 0.0034(5) 0.0054(6) C25 0.0304(7) 0.0258(7) 0.0168(6) 0.0062(5) -0.0003(5) 0.0062(6) C26 0.0226(6) 0.0195(6) 0.0190(6) 0.0075(5) 0.0011(5) 0.0039(5) C27 0.0220(6) 0.0206(6) 0.0213(6) 0.0040(5) -0.0022(5) 0.0050(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 Cl1 C27 1.7670(15) . ? Cl3 C27 1.7580(15) . ? Cl2 C27 1.7400(15) . ? O1 C23 1.2112(18) . ? O2 C26 1.2120(18) . ? N1 C11 1.4642(17) . ? N1 C21 1.4648(17) . ? N1 C10 1.4682(18) . ? N3 C12 1.3184(17) . ? N3 C20 1.3746(17) . ? N2 C1 1.3180(17) . ? N2 C9 1.3730(18) . ? N4 C26 1.3860(17) . ? N4 C23 1.3876(18) . ? N4 C22 1.4540(18) . ? C1 C2 1.421(2) . ? C1 C10 1.5074(19) . ? C2 C3 1.363(2) . ? C2 H2 0.9500 . ? C3 C4 1.417(2) . ? C3 H3 0.9500 . ? C4 C9 1.417(2) . ? C4 C5 1.418(2) . ? C5 C6 1.369(3) . ? C5 H5 0.9500 . ? C6 C7 1.406(3) . ? C6 H6 0.9500 . ? C7 C8 1.372(2) . ? C7 H7 0.9500 . ? C8 C9 1.416(2) . ? C8 H8 0.9500 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5055(19) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.418(2) . ? C13 C14 1.364(2) . ? C13 H13 0.9500 . ? C14 C15 1.4169(19) . ? C14 H14 0.9500 . ? C15 C16 1.416(2) . ? C15 C20 1.4179(19) . ? C16 C17 1.370(2) . ? C16 H16 0.9500 . ? C17 C18 1.410(2) . ? C17 H17 0.9500 . ? C18 C19 1.3734(19) . ? C18 H18 0.9500 . ? C19 C20 1.4149(18) . ? C19 H19 0.9500 . ? C21 C22 1.525(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.493(2) . ? C24 C25 1.329(2) . ? C24 H24 0.9500 . ? C25 C26 1.493(2) . ? C25 H25 0.9500 . ? C27 H27 1.0000 . ? 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 C11 N1 C21 110.28(11) . . ? C11 N1 C10 111.31(11) . . ? C21 N1 C10 111.73(11) . . ? C12 N3 C20 118.14(12) . . ? C1 N2 C9 118.25(12) . . ? C26 N4 C23 110.31(12) . . ? C26 N4 C22 124.35(12) . . ? C23 N4 C22 125.34(12) . . ? N2 C1 C2 122.99(13) . . ? N2 C1 C10 117.51(12) . . ? C2 C1 C10 119.49(12) . . ? C3 C2 C1 119.27(13) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 119.67(14) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C9 C4 C3 117.26(13) . . ? C9 C4 C5 119.10(14) . . ? C3 C4 C5 123.64(14) . . ? C6 C5 C4 120.54(15) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 120.19(15) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 120.79(15) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 120.20(15) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? N2 C9 C8 118.32(13) . . ? N2 C9 C4 122.53(13) . . ? C8 C9 C4 119.16(13) . . ? N1 C10 C1 110.58(11) . . ? N1 C10 H10A 109.5 . . ? C1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? N1 C11 C12 112.23(11) . . ? N1 C11 H11A 109.2 . . ? C12 C11 H11A 109.2 . . ? N1 C11 H11B 109.2 . . ? C12 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? N3 C12 C13 123.29(13) . . ? N3 C12 C11 117.50(12) . . ? C13 C12 C11 119.19(12) . . ? C14 C13 C12 119.23(13) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C15 119.49(13) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 123.17(13) . . ? C16 C15 C20 119.25(12) . . ? C14 C15 C20 117.56(13) . . ? C17 C16 C15 120.36(13) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 120.43(13) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 120.43(13) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C20 120.32(13) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? N3 C20 C19 118.50(12) . . ? N3 C20 C15 122.28(12) . . ? C19 C20 C15 119.20(12) . . ? N1 C21 C22 111.20(11) . . ? N1 C21 H21A 109.4 . . ? C22 C21 H21A 109.4 . . ? N1 C21 H21B 109.4 . . ? C22 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? N4 C22 C21 111.05(11) . . ? N4 C22 H22A 109.4 . . ? C21 C22 H22A 109.4 . . ? N4 C22 H22B 109.4 . . ? C21 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? O1 C23 N4 125.52(14) . . ? O1 C23 C24 127.96(14) . . ? N4 C23 C24 106.52(12) . . ? C25 C24 C23 108.16(13) . . ? C25 C24 H24 125.9 . . ? C23 C24 H24 125.9 . . ? C24 C25 C26 108.82(13) . . ? C24 C25 H25 125.6 . . ? C26 C25 H25 125.6 . . ? O2 C26 N4 125.29(13) . . ? O2 C26 C25 128.53(13) . . ? N4 C26 C25 106.18(12) . . ? Cl2 C27 Cl3 111.09(9) . . ? Cl2 C27 Cl1 110.13(8) . . ? Cl3 C27 Cl1 110.77(8) . . ? Cl2 C27 H27 108.3 . . ? Cl3 C27 H27 108.3 . . ? Cl1 C27 H27 108.3 . . ? 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 C9 N2 C1 C2 -1.0(2) . . . . ? C9 N2 C1 C10 179.74(11) . . . . ? N2 C1 C2 C3 1.3(2) . . . . ? C10 C1 C2 C3 -179.42(13) . . . . ? C1 C2 C3 C4 -0.3(2) . . . . ? C2 C3 C4 C9 -1.0(2) . . . . ? C2 C3 C4 C5 179.25(14) . . . . ? C9 C4 C5 C6 -0.5(2) . . . . ? C3 C4 C5 C6 179.24(15) . . . . ? C4 C5 C6 C7 -0.7(2) . . . . ? C5 C6 C7 C8 0.9(2) . . . . ? C6 C7 C8 C9 0.1(2) . . . . ? C1 N2 C9 C8 179.29(13) . . . . ? C1 N2 C9 C4 -0.4(2) . . . . ? C7 C8 C9 N2 179.03(13) . . . . ? C7 C8 C9 C4 -1.3(2) . . . . ? C3 C4 C9 N2 1.4(2) . . . . ? C5 C4 C9 N2 -178.87(13) . . . . ? C3 C4 C9 C8 -178.28(13) . . . . ? C5 C4 C9 C8 1.5(2) . . . . ? C11 N1 C10 C1 166.61(11) . . . . ? C21 N1 C10 C1 -69.62(14) . . . . ? N2 C1 C10 N1 118.89(13) . . . . ? C2 C1 C10 N1 -60.39(16) . . . . ? C21 N1 C11 C12 165.03(11) . . . . ? C10 N1 C11 C12 -70.37(15) . . . . ? C20 N3 C12 C13 0.4(2) . . . . ? C20 N3 C12 C11 179.00(11) . . . . ? N1 C11 C12 N3 127.96(13) . . . . ? N1 C11 C12 C13 -53.42(17) . . . . ? N3 C12 C13 C14 -0.2(2) . . . . ? C11 C12 C13 C14 -178.69(13) . . . . ? C12 C13 C14 C15 -0.1(2) . . . . ? C13 C14 C15 C16 -178.60(14) . . . . ? C13 C14 C15 C20 0.1(2) . . . . ? C14 C15 C16 C17 178.18(15) . . . . ? C20 C15 C16 C17 -0.5(2) . . . . ? C15 C16 C17 C18 0.3(2) . . . . ? C16 C17 C18 C19 0.0(2) . . . . ? C17 C18 C19 C20 0.1(2) . . . . ? C12 N3 C20 C19 177.97(12) . . . . ? C12 N3 C20 C15 -0.44(19) . . . . ? C18 C19 C20 N3 -178.77(12) . . . . ? C18 C19 C20 C15 -0.3(2) . . . . ? C16 C15 C20 N3 178.95(13) . . . . ? C14 C15 C20 N3 0.2(2) . . . . ? C16 C15 C20 C19 0.6(2) . . . . ? C14 C15 C20 C19 -178.24(13) . . . . ? C11 N1 C21 C22 -85.66(14) . . . . ? C10 N1 C21 C22 149.99(11) . . . . ? C26 N4 C22 C21 -73.20(16) . . . . ? C23 N4 C22 C21 105.67(15) . . . . ? N1 C21 C22 N4 -67.19(14) . . . . ? C26 N4 C23 O1 -178.56(14) . . . . ? C22 N4 C23 O1 2.4(2) . . . . ? C26 N4 C23 C24 1.21(15) . . . . ? C22 N4 C23 C24 -177.79(12) . . . . ? O1 C23 C24 C25 178.68(16) . . . . ? N4 C23 C24 C25 -1.09(17) . . . . ? C23 C24 C25 C26 0.55(17) . . . . ? C23 N4 C26 O2 179.04(14) . . . . ? C22 N4 C26 O2 -2.0(2) . . . . ? C23 N4 C26 C25 -0.89(15) . . . . ? C22 N4 C26 C25 178.12(12) . . . . ? C24 C25 C26 O2 -179.75(16) . . . . ? C24 C25 C26 N4 0.17(17) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 31.50 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.025 _refine_diff_density_min -1.309 _refine_diff_density_rms 0.070