# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Katayev, Evgeny' _publ_contact_author_email evgeny.katayev@chemie.uni-r.de _publ_section_title ; Macrocyclic receptor for pertechnetate and perrhenate anions ; loop_ _publ_author_name G.Kolesnikov K.German G.Kirakosyan I.Tananaev Yu.Ustynyuk ; V.Khrustalev ; E.Katayev # Attachment 'DP1PYCL.CIF' data_dp1pyCl _database_code_depnum_ccdc_archive 'CCDC 818214' #TrackingRef 'DP1PYCL.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C43 H43 N7 O2, C H2 Cl2, 2(Cl)' _chemical_formula_sum 'C44 H45 Cl4 N7 O2' _chemical_formula_weight 845.67 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.89(4) _cell_length_b 15.29(4) _cell_length_c 16.64(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.63(3) _cell_angle_gamma 90.00 _cell_volume 4023(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 616 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 15.16 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1768 _exptl_absorpt_coefficient_mu 0.343 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.950 _exptl_absorpt_correction_T_max 0.973 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 33694 _diffrn_reflns_av_R_equivalents 0.1104 _diffrn_reflns_av_sigmaI/netI 0.5476 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7016 _reflns_number_gt 1635 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.01P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7016 _refine_ls_number_parameters 528 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3707 _refine_ls_R_factor_gt 0.0906 _refine_ls_wR_factor_ref 0.2213 _refine_ls_wR_factor_gt 0.1391 _refine_ls_goodness_of_fit_ref 0.876 _refine_ls_restrained_S_all 0.876 _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 O1 O 1.3426(3) 1.1195(3) 0.8961(3) 0.0556(16) Uani 1 1 d . . . O2 O 1.3382(3) 0.6805(3) 0.9716(3) 0.0580(17) Uani 1 1 d . . . N1 N 0.8397(3) 0.9700(3) 0.4874(3) 0.0460(19) Uani 1 1 d . . . H1N H 0.8678 0.9399 0.5338 0.055 Uiso 1 1 calc R . . N2 N 0.9821(3) 1.0692(3) 0.5907(3) 0.0405(18) Uani 1 1 d . . . H2N H 0.9741 1.0148 0.6034 0.049 Uiso 1 1 calc R . . N3 N 1.2206(3) 1.0426(3) 0.8459(3) 0.0427(19) Uani 1 1 d . . . H3N H 1.1977 0.9934 0.8545 0.051 Uiso 1 1 calc R . . N4 N 1.3012(3) 0.9030(3) 0.9290(3) 0.0384(17) Uani 1 1 d . . . N5 N 1.2228(3) 0.7502(4) 0.8844(3) 0.0449(19) Uani 1 1 d . . . H5N H 1.1979 0.8016 0.8776 0.054 Uiso 1 1 calc R . . N6 N 0.9812(3) 0.6790(3) 0.6459(3) 0.0453(18) Uani 1 1 d . . . H6N H 0.9644 0.7316 0.6542 0.054 Uiso 1 1 calc R . . N7 N 0.8359(3) 0.7620(3) 0.5175(3) 0.0425(18) Uani 1 1 d . . . H7N H 0.8567 0.7981 0.5611 0.051 Uiso 1 1 calc R . . C1 C 0.7673(4) 0.9432(5) 0.4252(5) 0.046(2) Uani 1 1 d . . . C2 C 0.7421(4) 1.0075(4) 0.3616(4) 0.039(2) Uani 1 1 d . . . C3 C 0.8018(4) 1.0731(4) 0.3873(5) 0.051(2) Uani 1 1 d . . . C4 C 0.8624(4) 1.0493(4) 0.4677(4) 0.041(2) Uani 1 1 d . . . C5 C 0.9309(4) 1.1003(4) 0.5193(4) 0.040(2) Uani 1 1 d . . . H5 H 0.9393 1.1575 0.5015 0.047 Uiso 1 1 calc R . . C6 C 1.0516(4) 1.1163(4) 0.6515(5) 0.048(2) Uani 1 1 d . . . C7 C 1.1042(4) 1.0641(4) 0.7173(4) 0.036(2) Uani 1 1 d . . . H7 H 1.0939 1.0030 0.7167 0.043 Uiso 1 1 calc R . . C8 C 1.1700(4) 1.0991(4) 0.7825(4) 0.044(2) Uani 1 1 d . . . C9 C 1.1830(4) 1.1887(5) 0.7792(4) 0.052(2) Uani 1 1 d . . . H9 H 1.2302 1.2155 0.8215 0.063 Uiso 1 1 calc R . . C10 C 1.1269(4) 1.2397(5) 0.7138(5) 0.051(2) Uani 1 1 d . . . H10 H 1.1345 1.3013 0.7140 0.062 Uiso 1 1 calc R . . C11 C 1.0633(4) 1.2029(4) 0.6517(4) 0.046(2) Uani 1 1 d . . . H11 H 1.0260 1.2380 0.6074 0.055 Uiso 1 1 calc R . . C12 C 1.3005(4) 1.0576(5) 0.8940(5) 0.047(2) Uani 1 1 d . . . C13 C 1.3402(4) 0.9796(5) 0.9494(5) 0.050(3) Uani 1 1 d . . . C14 C 1.4120(4) 0.9909(5) 1.0211(5) 0.064(3) Uani 1 1 d . . . H14 H 1.4370 1.0470 1.0363 0.076 Uiso 1 1 calc R . . C15 C 1.4462(4) 0.9187(5) 1.0696(5) 0.056(3) Uani 1 1 d . . . H15 H 1.4961 0.9250 1.1187 0.067 Uiso 1 1 calc R . . C16 C 1.4100(4) 0.8376(5) 1.0489(4) 0.052(3) Uani 1 1 d . . . H16 H 1.4331 0.7877 1.0831 0.063 Uiso 1 1 calc R . . C17 C 1.3374(4) 0.8321(5) 0.9751(5) 0.049(2) Uani 1 1 d . . . C18 C 1.2991(4) 0.7469(5) 0.9439(5) 0.052(3) Uani 1 1 d . . . C19 C 1.1767(4) 0.6854(4) 0.8316(5) 0.044(2) Uani 1 1 d . . . C20 C 1.1024(4) 0.7078(4) 0.7658(4) 0.041(2) Uani 1 1 d . . . H20 H 1.0844 0.7671 0.7589 0.050 Uiso 1 1 calc R . . C21 C 1.0558(4) 0.6470(4) 0.7116(5) 0.042(2) Uani 1 1 d . . . C22 C 1.0765(4) 0.5629(4) 0.7182(4) 0.045(2) Uani 1 1 d . . . H22 H 1.0420 0.5212 0.6790 0.054 Uiso 1 1 calc R . . C23 C 1.1490(4) 0.5379(5) 0.7831(4) 0.046(2) Uani 1 1 d . . . H23 H 1.1649 0.4780 0.7893 0.055 Uiso 1 1 calc R . . C24 C 1.1994(4) 0.5991(5) 0.8399(4) 0.048(2) Uani 1 1 d . . . H24 H 1.2496 0.5810 0.8845 0.058 Uiso 1 1 calc R . . C25 C 0.9346(4) 0.6396(4) 0.5744(4) 0.043(2) Uani 1 1 d . . . H25 H 0.9484 0.5813 0.5646 0.052 Uiso 1 1 calc R . . C26 C 0.8661(4) 0.6799(4) 0.5128(5) 0.044(2) Uani 1 1 d . . . C27 C 0.8136(4) 0.6443(4) 0.4349(4) 0.038(2) Uani 1 1 d . . . C28 C 0.7558(4) 0.7062(4) 0.3946(4) 0.041(2) Uani 1 1 d . . . C29 C 0.7698(4) 0.7794(5) 0.4458(5) 0.044(2) Uani 1 1 d . . . C30 C 0.7211(4) 0.8638(4) 0.4297(4) 0.037(2) Uani 1 1 d . . . H30 H 0.6761 0.8574 0.3718 0.044 Uiso 1 1 calc R . . C31 C 0.6667(4) 1.0050(5) 0.2846(4) 0.046(2) Uani 1 1 d . . . H31A H 0.6712 1.0493 0.2439 0.069 Uiso 1 1 calc R . . H31B H 0.6168 1.0170 0.2998 0.069 Uiso 1 1 calc R . . H31C H 0.6613 0.9470 0.2582 0.069 Uiso 1 1 calc R . . C32 C 0.8007(4) 1.1572(4) 0.3420(5) 0.050(2) Uani 1 1 d . . . H32A H 0.7894 1.1445 0.2806 0.060 Uiso 1 1 calc R . . H32B H 0.8575 1.1841 0.3658 0.060 Uiso 1 1 calc R . . C33 C 0.7372(4) 1.2218(5) 0.3479(5) 0.066(3) Uani 1 1 d . . . H33A H 0.7301 1.2678 0.3049 0.099 Uiso 1 1 calc R . . H33B H 0.7566 1.2478 0.4054 0.099 Uiso 1 1 calc R . . H33C H 0.6829 1.1923 0.3373 0.099 Uiso 1 1 calc R . . C34 C 0.8239(4) 0.5593(4) 0.4002(5) 0.050(2) Uani 1 1 d . . . H34A H 0.8796 0.5354 0.4362 0.059 Uiso 1 1 calc R . . H34B H 0.8257 0.5686 0.3419 0.059 Uiso 1 1 calc R . . C35 C 0.7574(4) 0.4908(4) 0.3939(4) 0.055(3) Uani 1 1 d . . . H35A H 0.7627 0.4427 0.3572 0.083 Uiso 1 1 calc R . . H35B H 0.7010 0.5171 0.3691 0.083 Uiso 1 1 calc R . . H35C H 0.7653 0.4683 0.4514 0.083 Uiso 1 1 calc R . . C36 C 0.6886(4) 0.6966(5) 0.3094(4) 0.054(3) Uani 1 1 d . . . H36A H 0.7102 0.6624 0.2717 0.081 Uiso 1 1 calc R . . H36B H 0.6711 0.7545 0.2842 0.081 Uiso 1 1 calc R . . H36C H 0.6399 0.6665 0.3157 0.081 Uiso 1 1 calc R . . C37 C 0.6741(4) 0.8744(4) 0.4926(4) 0.034(2) Uani 1 1 d . . . C38 C 0.6488(4) 0.9535(4) 0.5087(4) 0.036(2) Uani 1 1 d . . . H38 H 0.6659 1.0042 0.4859 0.043 Uiso 1 1 calc R . . C39 C 0.5982(4) 0.9624(4) 0.5582(4) 0.043(2) Uani 1 1 d . . . H39 H 0.5808 1.0192 0.5680 0.052 Uiso 1 1 calc R . . C40 C 0.5723(4) 0.8910(5) 0.5936(4) 0.048(2) Uani 1 1 d . . . C41 C 0.5995(4) 0.8108(4) 0.5756(4) 0.039(2) Uani 1 1 d . . . H41 H 0.5832 0.7592 0.5975 0.047 Uiso 1 1 calc R . . C42 C 0.6487(4) 0.8041(5) 0.5277(4) 0.042(2) Uani 1 1 d . . . H42 H 0.6666 0.7476 0.5178 0.051 Uiso 1 1 calc R . . C43 C 0.5156(4) 0.9010(4) 0.6455(4) 0.052(2) Uani 1 1 d . . . H43A H 0.5293 0.8558 0.6900 0.078 Uiso 1 1 calc R . . H43B H 0.4565 0.8949 0.6077 0.078 Uiso 1 1 calc R . . H43C H 0.5242 0.9589 0.6725 0.078 Uiso 1 1 calc R . . Cl1 Cl 0.95932(11) 0.88190(12) 0.65717(13) 0.0521(7) Uani 1 1 d . . . Cl2 Cl 1.07464(19) 0.8396(2) 1.0009(2) 0.0564(11) Uani 0.60 1 d P A 1 Cl2' Cl 1.0993(3) 0.9090(3) 0.8633(4) 0.071(2) Uani 0.40 1 d P B 2 C44 C 0.4495(5) 0.7992(5) 0.3527(5) 0.064(3) Uani 1 1 d . . . H44A H 0.4787 0.8223 0.4113 0.077 Uiso 1 1 calc R . . H44B H 0.3883 0.8110 0.3368 0.077 Uiso 1 1 calc R . . Cl3 Cl 0.46619(14) 0.68718(14) 0.35171(15) 0.0721(8) Uani 1 1 d . . . Cl4 Cl 0.48735(14) 0.85243(14) 0.28100(15) 0.0771(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.059(3) 0.033(3) 0.081(4) -0.010(3) 0.032(3) -0.009(3) O2 0.066(3) 0.045(3) 0.063(4) 0.002(3) 0.022(3) 0.012(3) N1 0.040(4) 0.039(4) 0.053(4) 0.010(3) 0.009(3) -0.009(3) N2 0.050(3) 0.032(4) 0.046(4) 0.002(3) 0.026(3) 0.001(3) N3 0.034(3) 0.040(4) 0.048(4) 0.013(3) 0.006(3) -0.010(3) N4 0.039(3) 0.046(4) 0.036(4) -0.006(3) 0.022(3) -0.001(3) N5 0.025(3) 0.050(4) 0.054(4) -0.004(3) 0.006(3) 0.002(3) N6 0.056(4) 0.036(4) 0.059(4) 0.003(3) 0.039(3) 0.013(3) N7 0.038(3) 0.039(4) 0.054(4) -0.012(3) 0.021(3) -0.003(3) C1 0.037(4) 0.053(5) 0.049(5) -0.009(4) 0.019(4) 0.018(4) C2 0.039(4) 0.050(5) 0.032(5) 0.006(4) 0.017(3) 0.001(4) C3 0.047(4) 0.045(5) 0.077(6) 0.024(4) 0.042(4) 0.004(4) C4 0.039(4) 0.043(5) 0.047(5) 0.016(4) 0.022(4) 0.005(4) C5 0.044(4) 0.025(4) 0.064(5) 0.010(4) 0.037(4) 0.008(3) C6 0.058(5) 0.025(4) 0.069(5) 0.001(4) 0.030(4) 0.002(4) C7 0.045(4) 0.017(4) 0.057(5) -0.001(4) 0.032(4) 0.006(3) C8 0.039(4) 0.045(5) 0.050(5) -0.020(4) 0.018(4) -0.017(4) C9 0.079(5) 0.045(5) 0.044(5) -0.018(4) 0.034(4) -0.014(4) C10 0.065(5) 0.035(5) 0.063(6) -0.006(4) 0.033(4) -0.004(4) C11 0.064(5) 0.030(5) 0.049(5) -0.002(4) 0.028(4) -0.003(4) C12 0.052(5) 0.044(5) 0.049(5) -0.011(4) 0.024(4) -0.005(4) C13 0.046(5) 0.040(5) 0.069(6) -0.003(4) 0.025(4) -0.008(4) C14 0.056(5) 0.062(6) 0.083(6) 0.001(5) 0.037(5) -0.017(4) C15 0.048(5) 0.070(6) 0.053(5) 0.005(5) 0.022(4) 0.005(4) C16 0.040(5) 0.063(6) 0.057(5) 0.010(5) 0.020(4) -0.006(4) C17 0.031(4) 0.047(5) 0.071(6) -0.002(4) 0.022(4) -0.003(4) C18 0.052(5) 0.047(5) 0.062(6) 0.010(5) 0.026(4) -0.002(4) C19 0.039(4) 0.036(5) 0.053(5) 0.013(4) 0.012(4) 0.014(4) C20 0.050(5) 0.031(5) 0.047(5) 0.008(4) 0.021(4) 0.000(4) C21 0.046(5) 0.022(4) 0.056(5) 0.016(4) 0.014(4) 0.012(3) C22 0.048(5) 0.043(5) 0.047(5) -0.001(4) 0.020(4) -0.005(4) C23 0.061(5) 0.033(5) 0.043(5) 0.003(4) 0.017(4) 0.005(4) C24 0.044(4) 0.055(5) 0.047(5) 0.023(4) 0.017(4) 0.018(4) C25 0.046(4) 0.036(5) 0.054(5) -0.012(4) 0.025(4) 0.004(4) C26 0.035(4) 0.038(5) 0.058(5) -0.006(4) 0.017(4) -0.006(4) C27 0.052(5) 0.018(4) 0.044(5) -0.010(4) 0.017(4) 0.005(3) C28 0.033(4) 0.041(5) 0.043(5) -0.007(4) 0.008(4) -0.004(4) C29 0.028(4) 0.052(5) 0.058(5) 0.002(4) 0.022(4) -0.003(4) C30 0.027(4) 0.044(5) 0.043(5) 0.003(4) 0.017(3) -0.004(4) C31 0.052(5) 0.051(5) 0.043(5) -0.007(4) 0.024(4) 0.000(4) C32 0.049(5) 0.047(5) 0.063(5) 0.012(4) 0.029(4) 0.006(4) C33 0.081(6) 0.044(5) 0.072(6) 0.003(5) 0.026(5) 0.013(5) C34 0.050(5) 0.048(5) 0.051(5) -0.008(4) 0.019(4) 0.001(4) C35 0.052(5) 0.048(5) 0.068(6) -0.006(4) 0.023(4) -0.016(4) C36 0.040(5) 0.052(5) 0.072(6) 0.006(5) 0.022(4) 0.002(4) C37 0.032(4) 0.034(4) 0.034(4) 0.010(4) 0.009(3) -0.004(3) C38 0.032(4) 0.023(4) 0.048(5) 0.005(4) 0.009(4) 0.004(3) C39 0.040(4) 0.039(5) 0.048(5) -0.013(4) 0.013(4) 0.001(4) C40 0.041(4) 0.067(6) 0.029(5) 0.004(4) 0.005(4) -0.001(4) C41 0.058(5) 0.026(4) 0.036(5) 0.002(4) 0.021(4) 0.005(4) C42 0.044(4) 0.053(5) 0.036(5) 0.005(4) 0.022(4) 0.011(4) C43 0.058(5) 0.064(5) 0.049(5) -0.001(4) 0.038(4) -0.003(4) Cl1 0.0542(12) 0.0313(11) 0.0606(14) 0.0055(11) 0.0074(10) -0.0006(10) Cl2 0.0468(18) 0.080(2) 0.052(2) -0.0303(19) 0.0289(15) -0.0319(17) Cl2' 0.035(3) 0.015(3) 0.122(5) 0.011(3) -0.024(3) -0.008(2) C44 0.086(6) 0.072(6) 0.045(5) -0.003(5) 0.036(4) 0.018(5) Cl3 0.0820(15) 0.0638(15) 0.0747(16) -0.0008(13) 0.0327(12) -0.0055(12) Cl4 0.0907(17) 0.0697(16) 0.0732(16) 0.0036(13) 0.0317(13) -0.0079(13) _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 O1 C12 1.177(8) . ? O2 C18 1.210(8) . ? N1 C4 1.346(8) . ? N1 C1 1.358(8) . ? N1 H1N 0.8800 . ? N2 C5 1.289(8) . ? N2 C6 1.443(8) . ? N2 H2N 0.8800 . ? N3 C12 1.324(8) . ? N3 C8 1.398(8) . ? N3 H3N 0.8800 . ? N4 C13 1.328(8) . ? N4 C17 1.344(8) . ? N5 C18 1.322(8) . ? N5 C19 1.370(8) . ? N5 H5N 0.8800 . ? N6 C25 1.318(8) . ? N6 C21 1.433(8) . ? N6 H6N 0.8800 . ? N7 C29 1.343(8) . ? N7 C26 1.367(8) . ? N7 H7N 0.8800 . ? C1 C2 1.396(9) . ? C1 C30 1.459(9) . ? C2 C3 1.380(9) . ? C2 C31 1.455(8) . ? C3 C4 1.416(9) . ? C3 C32 1.487(9) . ? C4 C5 1.408(9) . ? C5 H5 0.9500 . ? C6 C11 1.338(9) . ? C6 C7 1.393(9) . ? C7 C8 1.360(8) . ? C7 H7 0.9500 . ? C8 C9 1.392(10) . ? C9 C10 1.401(9) . ? C9 H9 0.9500 . ? C10 C11 1.325(9) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.513(10) . ? C13 C14 1.379(9) . ? C14 C15 1.369(10) . ? C14 H14 0.9500 . ? C15 C16 1.371(10) . ? C15 H15 0.9500 . ? C16 C17 1.400(9) . ? C16 H16 0.9500 . ? C17 C18 1.466(10) . ? C19 C24 1.367(9) . ? C19 C20 1.387(8) . ? C20 C21 1.340(9) . ? C20 H20 0.9500 . ? C21 C22 1.328(9) . ? C22 C23 1.372(8) . ? C22 H22 0.9500 . ? C23 C24 1.388(9) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C26 1.391(9) . ? C25 H25 0.9500 . ? C26 C27 1.399(9) . ? C27 C28 1.356(9) . ? C27 C34 1.457(9) . ? C28 C29 1.375(9) . ? C28 C36 1.479(9) . ? C29 C30 1.503(9) . ? C30 C37 1.528(9) . ? C30 H30 1.0000 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 C33 1.487(9) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 C35 1.513(9) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 C38 1.342(9) . ? C37 C42 1.362(9) . ? C38 C39 1.387(10) . ? C38 H38 0.9500 . ? C39 C40 1.383(10) . ? C39 H39 0.9500 . ? C40 C41 1.380(10) . ? C40 C43 1.507(10) . ? C41 C42 1.342(9) . ? C41 H41 0.9500 . ? C42 H42 0.9500 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 Cl3 1.737(8) . ? C44 Cl4 1.741(8) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? 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 C4 N1 C1 110.1(6) . . ? C4 N1 H1N 124.9 . . ? C1 N1 H1N 124.9 . . ? C5 N2 C6 125.3(6) . . ? C5 N2 H2N 117.3 . . ? C6 N2 H2N 117.3 . . ? C12 N3 C8 124.8(6) . . ? C12 N3 H3N 117.6 . . ? C8 N3 H3N 117.6 . . ? C13 N4 C17 118.7(6) . . ? C18 N5 C19 129.6(6) . . ? C18 N5 H5N 115.2 . . ? C19 N5 H5N 115.2 . . ? C25 N6 C21 128.2(6) . . ? C25 N6 H6N 115.9 . . ? C21 N6 H6N 115.9 . . ? C29 N7 C26 110.0(6) . . ? C29 N7 H7N 125.0 . . ? C26 N7 H7N 125.0 . . ? N1 C1 C2 108.5(6) . . ? N1 C1 C30 124.5(6) . . ? C2 C1 C30 126.8(6) . . ? C3 C2 C1 106.5(6) . . ? C3 C2 C31 127.6(6) . . ? C1 C2 C31 125.9(6) . . ? C2 C3 C4 108.2(6) . . ? C2 C3 C32 126.4(6) . . ? C4 C3 C32 125.3(6) . . ? N1 C4 C5 126.4(6) . . ? N1 C4 C3 106.8(6) . . ? C5 C4 C3 126.8(6) . . ? N2 C5 C4 119.9(6) . . ? N2 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C11 C6 C7 120.8(6) . . ? C11 C6 N2 125.3(6) . . ? C7 C6 N2 113.7(6) . . ? C8 C7 C6 121.2(6) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C9 116.9(6) . . ? C7 C8 N3 118.0(6) . . ? C9 C8 N3 125.1(6) . . ? C8 C9 C10 120.4(6) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 120.6(7) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C6 120.1(7) . . ? C10 C11 H11 120.0 . . ? C6 C11 H11 120.0 . . ? O1 C12 N3 129.3(7) . . ? O1 C12 C13 118.8(6) . . ? N3 C12 C13 111.7(6) . . ? N4 C13 C14 122.5(7) . . ? N4 C13 C12 117.7(6) . . ? C14 C13 C12 119.6(7) . . ? C15 C14 C13 117.9(7) . . ? C15 C14 H14 121.0 . . ? C13 C14 H14 121.0 . . ? C14 C15 C16 121.5(7) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C15 C16 C17 116.7(7) . . ? C15 C16 H16 121.6 . . ? C17 C16 H16 121.6 . . ? N4 C17 C16 122.3(7) . . ? N4 C17 C18 117.3(6) . . ? C16 C17 C18 120.4(7) . . ? O2 C18 N5 125.1(7) . . ? O2 C18 C17 119.8(7) . . ? N5 C18 C17 115.1(6) . . ? C24 C19 N5 123.9(6) . . ? C24 C19 C20 117.5(6) . . ? N5 C19 C20 118.6(6) . . ? C21 C20 C19 120.9(7) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C22 C21 C20 122.8(6) . . ? C22 C21 N6 121.9(6) . . ? C20 C21 N6 115.3(6) . . ? C21 C22 C23 118.1(6) . . ? C21 C22 H22 121.0 . . ? C23 C22 H22 121.0 . . ? C22 C23 C24 120.8(7) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C19 C24 C23 119.9(6) . . ? C19 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? N6 C25 C26 122.7(6) . . ? N6 C25 H25 118.7 . . ? C26 C25 H25 118.7 . . ? N7 C26 C25 126.5(6) . . ? N7 C26 C27 106.4(6) . . ? C25 C26 C27 127.0(7) . . ? C28 C27 C26 107.3(6) . . ? C28 C27 C34 126.4(6) . . ? C26 C27 C34 126.1(6) . . ? C27 C28 C29 109.0(6) . . ? C27 C28 C36 125.5(6) . . ? C29 C28 C36 125.5(6) . . ? N7 C29 C28 107.3(6) . . ? N7 C29 C30 124.0(6) . . ? C28 C29 C30 128.7(6) . . ? C1 C30 C29 117.0(6) . . ? C1 C30 C37 111.3(6) . . ? C29 C30 C37 110.7(6) . . ? C1 C30 H30 105.6 . . ? C29 C30 H30 105.6 . . ? C37 C30 H30 105.6 . . ? C2 C31 H31A 109.5 . . ? C2 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C2 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C3 C32 C33 114.9(6) . . ? C3 C32 H32A 108.6 . . ? C33 C32 H32A 108.6 . . ? C3 C32 H32B 108.6 . . ? C33 C32 H32B 108.6 . . ? H32A C32 H32B 107.5 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C27 C34 C35 117.0(6) . . ? C27 C34 H34A 108.0 . . ? C35 C34 H34A 108.0 . . ? C27 C34 H34B 108.0 . . ? C35 C34 H34B 108.0 . . ? H34A C34 H34B 107.3 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C28 C36 H36A 109.5 . . ? C28 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C28 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C38 C37 C42 117.1(7) . . ? C38 C37 C30 120.7(6) . . ? C42 C37 C30 121.9(6) . . ? C37 C38 C39 120.8(7) . . ? C37 C38 H38 119.6 . . ? C39 C38 H38 119.6 . . ? C40 C39 C38 122.0(7) . . ? C40 C39 H39 119.0 . . ? C38 C39 H39 119.0 . . ? C41 C40 C39 115.4(7) . . ? C41 C40 C43 122.9(7) . . ? C39 C40 C43 121.7(7) . . ? C42 C41 C40 121.3(7) . . ? C42 C41 H41 119.3 . . ? C40 C41 H41 119.3 . . ? C41 C42 C37 123.3(7) . . ? C41 C42 H42 118.3 . . ? C37 C42 H42 118.3 . . ? C40 C43 H43A 109.5 . . ? C40 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C40 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? Cl3 C44 Cl4 110.8(4) . . ? Cl3 C44 H44A 109.5 . . ? Cl4 C44 H44A 109.5 . . ? Cl3 C44 H44B 109.5 . . ? Cl4 C44 H44B 109.5 . . ? H44A C44 H44B 108.1 . . ? 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 C4 N1 C1 C2 0.7(8) . . . . ? C4 N1 C1 C30 -174.3(7) . . . . ? N1 C1 C2 C3 0.4(8) . . . . ? C30 C1 C2 C3 175.3(7) . . . . ? N1 C1 C2 C31 -178.7(7) . . . . ? C30 C1 C2 C31 -3.9(12) . . . . ? C1 C2 C3 C4 -1.3(9) . . . . ? C31 C2 C3 C4 177.8(7) . . . . ? C1 C2 C3 C32 -177.7(7) . . . . ? C31 C2 C3 C32 1.4(13) . . . . ? C1 N1 C4 C5 175.8(7) . . . . ? C1 N1 C4 C3 -1.5(8) . . . . ? C2 C3 C4 N1 1.7(9) . . . . ? C32 C3 C4 N1 178.2(7) . . . . ? C2 C3 C4 C5 -175.5(7) . . . . ? C32 C3 C4 C5 1.0(13) . . . . ? C6 N2 C5 C4 -176.3(7) . . . . ? N1 C4 C5 N2 4.6(12) . . . . ? C3 C4 C5 N2 -178.7(7) . . . . ? C5 N2 C6 C11 14.0(12) . . . . ? C5 N2 C6 C7 -171.5(7) . . . . ? C11 C6 C7 C8 -1.7(12) . . . . ? N2 C6 C7 C8 -176.4(6) . . . . ? C6 C7 C8 C9 -1.1(11) . . . . ? C6 C7 C8 N3 -179.4(7) . . . . ? C12 N3 C8 C7 154.7(7) . . . . ? C12 N3 C8 C9 -23.4(12) . . . . ? C7 C8 C9 C10 3.7(11) . . . . ? N3 C8 C9 C10 -178.2(7) . . . . ? C8 C9 C10 C11 -3.6(12) . . . . ? C9 C10 C11 C6 0.7(12) . . . . ? C7 C6 C11 C10 1.9(12) . . . . ? N2 C6 C11 C10 176.0(7) . . . . ? C8 N3 C12 O1 3.2(13) . . . . ? C8 N3 C12 C13 -173.6(6) . . . . ? C17 N4 C13 C14 -6.6(12) . . . . ? C17 N4 C13 C12 177.0(7) . . . . ? O1 C12 C13 N4 -160.9(7) . . . . ? N3 C12 C13 N4 16.3(10) . . . . ? O1 C12 C13 C14 22.6(12) . . . . ? N3 C12 C13 C14 -160.1(7) . . . . ? N4 C13 C14 C15 3.8(13) . . . . ? C12 C13 C14 C15 -179.9(7) . . . . ? C13 C14 C15 C16 -0.9(12) . . . . ? C14 C15 C16 C17 1.1(12) . . . . ? C13 N4 C17 C16 6.8(11) . . . . ? C13 N4 C17 C18 -171.8(7) . . . . ? C15 C16 C17 N4 -4.0(12) . . . . ? C15 C16 C17 C18 174.5(7) . . . . ? C19 N5 C18 O2 -11.5(14) . . . . ? C19 N5 C18 C17 166.8(7) . . . . ? N4 C17 C18 O2 164.6(7) . . . . ? C16 C17 C18 O2 -14.0(12) . . . . ? N4 C17 C18 N5 -13.8(11) . . . . ? C16 C17 C18 N5 167.6(7) . . . . ? C18 N5 C19 C24 8.9(13) . . . . ? C18 N5 C19 C20 -171.1(7) . . . . ? C24 C19 C20 C21 -1.1(12) . . . . ? N5 C19 C20 C21 179.0(7) . . . . ? C19 C20 C21 C22 1.1(12) . . . . ? C19 C20 C21 N6 -179.3(7) . . . . ? C25 N6 C21 C22 -16.6(12) . . . . ? C25 N6 C21 C20 163.7(7) . . . . ? C20 C21 C22 C23 -0.3(12) . . . . ? N6 C21 C22 C23 -180.0(7) . . . . ? C21 C22 C23 C24 -0.4(12) . . . . ? N5 C19 C24 C23 -179.6(7) . . . . ? C20 C19 C24 C23 0.4(11) . . . . ? C22 C23 C24 C19 0.3(12) . . . . ? C21 N6 C25 C26 -176.0(7) . . . . ? C29 N7 C26 C25 179.1(7) . . . . ? C29 N7 C26 C27 -1.9(8) . . . . ? N6 C25 C26 N7 -2.1(12) . . . . ? N6 C25 C26 C27 179.2(7) . . . . ? N7 C26 C27 C28 1.8(9) . . . . ? C25 C26 C27 C28 -179.3(8) . . . . ? N7 C26 C27 C34 176.7(7) . . . . ? C25 C26 C27 C34 -4.3(13) . . . . ? C26 C27 C28 C29 -1.0(9) . . . . ? C34 C27 C28 C29 -175.9(7) . . . . ? C26 C27 C28 C36 179.2(7) . . . . ? C34 C27 C28 C36 4.2(13) . . . . ? C26 N7 C29 C28 1.4(8) . . . . ? C26 N7 C29 C30 179.7(7) . . . . ? C27 C28 C29 N7 -0.2(9) . . . . ? C36 C28 C29 N7 179.7(7) . . . . ? C27 C28 C29 C30 -178.4(7) . . . . ? C36 C28 C29 C30 1.5(13) . . . . ? N1 C1 C30 C29 -54.8(10) . . . . ? C2 C1 C30 C29 131.1(8) . . . . ? N1 C1 C30 C37 73.8(8) . . . . ? C2 C1 C30 C37 -100.3(8) . . . . ? N7 C29 C30 C1 63.0(10) . . . . ? C28 C29 C30 C1 -119.1(8) . . . . ? N7 C29 C30 C37 -66.0(9) . . . . ? C28 C29 C30 C37 111.9(9) . . . . ? C2 C3 C32 C33 73.1(10) . . . . ? C4 C3 C32 C33 -102.7(9) . . . . ? C28 C27 C34 C35 -73.2(10) . . . . ? C26 C27 C34 C35 112.8(8) . . . . ? C1 C30 C37 C38 27.2(8) . . . . ? C29 C30 C37 C38 159.2(6) . . . . ? C1 C30 C37 C42 -159.5(6) . . . . ? C29 C30 C37 C42 -27.6(8) . . . . ? C42 C37 C38 C39 -0.8(9) . . . . ? C30 C37 C38 C39 172.8(5) . . . . ? C37 C38 C39 C40 0.7(10) . . . . ? C38 C39 C40 C41 -0.7(9) . . . . ? C38 C39 C40 C43 -178.5(6) . . . . ? C39 C40 C41 C42 0.8(9) . . . . ? C43 C40 C41 C42 178.7(6) . . . . ? C40 C41 C42 C37 -1.0(10) . . . . ? C38 C37 C42 C41 0.9(9) . . . . ? C30 C37 C42 C41 -172.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.534 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.072 _publ_section_references ; Bruker (2001). SAINTPlus, v. 6.2. Data Reduction and Correction Program, Bruker AXS, Madison, Wisconsin, USA. Bruker (2005). APEX2 software package, v. 1.27. Bruker Molecular Analysis Research Tool, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (2003). SADABS, v. 2.03, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (2008). Acta Cryst. A64, 112-122. ;