# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Alamgir Hossain' _publ_contact_author_email ALAMGIR@CHEM.JSUMS.EDU _publ_section_title ; Ditopic binding of perchlorate anion to hexaazamacrocyclic hosts ; loop_ _publ_author_name 'Alamgir Hossain' 'Frank R Fronczek' 'Musabbir. A. Saeed' 'Jameskia J. Thompson' # Attachment 'Ligand_L2_ThEAClO4.cif' data_THEMOCTCLO4 _database_code_depnum_ccdc_archive 'CCDC 739057' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H40 N6 S2, 6(Cl O4), 4(H2 O)' _chemical_formula_sum 'C20 H48 Cl6 N6 O28 S2' _chemical_formula_weight 1097.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3060(6) _cell_length_b 10.5205(9) _cell_length_c 12.4149(10) _cell_angle_alpha 103.619(5) _cell_angle_beta 90.201(5) _cell_angle_gamma 94.123(5) _cell_volume 1051.39(15) _cell_formula_units_Z 1 _cell_measurement_temperature 90.0(5) _cell_measurement_reflns_used 7445 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 68.3 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.733 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 5.589 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.314 _exptl_absorpt_correction_T_max 0.605 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(5) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex-II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10176 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.6 _diffrn_reflns_theta_max 68.7 _reflns_number_total 3690 _reflns_number_gt 3561 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker Apex2' _computing_data_reduction 'Bruker Apex2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _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. The disordered perchlorate was modeled with SADI restraints in order to yield similar Cl-O and O...O distances for all such occurrences in both of the orientations. O-H and H...H distances were also restrained in the water molecules. This led to 103 total restraints. ; _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^)+(0.0406P)^2^+1.0629P] 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 SHELXL _refine_ls_extinction_coef 0.0022(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3690 _refine_ls_number_parameters 345 _refine_ls_number_restraints 103 _refine_ls_R_factor_all 0.033 _refine_ls_R_factor_gt 0.032 _refine_ls_wR_factor_ref 0.087 _refine_ls_wR_factor_gt 0.086 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.89877(6) 0.35253(5) 0.61960(4) 0.01703(14) Uani 1 1 d . . . N1 N 0.6642(2) 0.36054(16) 0.84590(14) 0.0166(4) Uani 1 1 d . . . H1A H 0.7501 0.3174 0.8571 0.020 Uiso 1 1 calc R . . H1B H 0.6176 0.3876 0.9119 0.020 Uiso 1 1 calc R . . N2 N 0.3952(2) 0.05329(16) 0.74913(14) 0.0163(4) Uani 1 1 d . . . H2A H 0.4535 0.0322 0.6873 0.020 Uiso 1 1 calc R . . H2B H 0.3007 0.0799 0.7303 0.020 Uiso 1 1 calc R . . N3 N 0.13291(19) -0.18683(16) 0.66896(14) 0.0158(3) Uani 1 1 d . . . H3A H 0.1268 -0.1326 0.6230 0.019 Uiso 1 1 calc R . . H3B H 0.0738 -0.1558 0.7287 0.019 Uiso 1 1 calc R . . C1 C 0.8500(2) 0.38043(19) 0.49209(16) 0.0162(4) Uani 1 1 d . . . C2 C 0.7313(2) 0.4646(2) 0.50078(17) 0.0193(4) Uani 1 1 d . . . H2 H 0.6915 0.4933 0.4412 0.023 Uiso 1 1 calc R . . C3 C 0.6748(2) 0.5041(2) 0.61037(18) 0.0194(4) Uani 1 1 d . . . H3 H 0.5925 0.5600 0.6299 0.023 Uiso 1 1 calc R . . C4 C 0.7533(2) 0.45160(19) 0.68385(17) 0.0173(4) Uani 1 1 d . . . C5 C 0.7238(3) 0.47987(19) 0.80581(17) 0.0193(4) Uani 1 1 d . . . H5A H 0.6449 0.5449 0.8236 0.023 Uiso 1 1 calc R . . H5B H 0.8235 0.5173 0.8454 0.023 Uiso 1 1 calc R . . C6 C 0.5469(2) 0.26663(19) 0.77047(17) 0.0163(4) Uani 1 1 d . . . H6A H 0.5995 0.2255 0.7029 0.020 Uiso 1 1 calc R . . H6B H 0.4582 0.3126 0.7510 0.020 Uiso 1 1 calc R . . C7 C 0.4839(2) 0.16329(19) 0.83021(16) 0.0175(4) Uani 1 1 d . . . H7A H 0.5733 0.1309 0.8637 0.021 Uiso 1 1 calc R . . H7B H 0.4123 0.2014 0.8886 0.021 Uiso 1 1 calc R . . C8 C 0.3630(2) -0.0658(2) 0.79423(17) 0.0192(4) Uani 1 1 d . . . H8A H 0.2817 -0.0487 0.8507 0.023 Uiso 1 1 calc R . . H8B H 0.4610 -0.0833 0.8291 0.023 Uiso 1 1 calc R . . C9 C 0.3055(2) -0.1860(2) 0.70522(18) 0.0182(4) Uani 1 1 d . . . H9A H 0.3736 -0.1910 0.6413 0.022 Uiso 1 1 calc R . . H9B H 0.3183 -0.2636 0.7330 0.022 Uiso 1 1 calc R . . C10 C 0.9381(2) 0.32170(19) 0.38928(16) 0.0163(4) Uani 1 1 d . . . H10A H 1.0502 0.3162 0.4088 0.020 Uiso 1 1 calc R . . H10B H 0.9357 0.3791 0.3387 0.020 Uiso 1 1 calc R . . Cl1 Cl -0.18286(6) -0.14686(5) 0.89583(4) 0.02019(15) Uani 1 1 d . . . O1 O -0.26909(19) -0.03002(16) 0.93014(14) 0.0285(4) Uani 1 1 d . . . O2 O -0.01534(19) -0.10825(17) 0.87822(14) 0.0294(4) Uani 1 1 d . . . O3 O -0.1896(2) -0.21854(17) 0.98103(14) 0.0310(4) Uani 1 1 d . . . O4 O -0.2516(2) -0.22729(16) 0.79432(14) 0.0355(4) Uani 1 1 d . . . Cl2 Cl 0.27560(5) 0.07197(5) 0.46682(4) 0.01900(15) Uani 1 1 d . . . O5 O 0.3174(2) 0.03091(18) 0.35281(14) 0.0329(4) Uani 1 1 d . . . O6 O 0.11739(18) 0.12008(16) 0.47567(13) 0.0265(4) Uani 1 1 d . . . O7 O 0.2767(2) -0.03843(17) 0.51668(14) 0.0331(4) Uani 1 1 d . . . O8 O 0.3905(2) 0.1727(2) 0.52497(19) 0.0483(5) Uani 1 1 d . . . Cl3A Cl 0.2636(5) 0.5500(4) 0.8741(4) 0.0216(8) Uani 0.351(6) 1 d PD A 1 O9A O 0.3017(15) 0.5087(12) 0.7590(6) 0.039(6) Uani 0.351(6) 1 d PD A 1 O10A O 0.3273(13) 0.4606(9) 0.9319(10) 0.074(5) Uani 0.351(6) 1 d PD A 1 O11A O 0.3409(9) 0.6761(5) 0.9189(4) 0.053(2) Uani 0.351(6) 1 d PD A 1 O12A O 0.0953(6) 0.5501(10) 0.8861(7) 0.114(5) Uani 0.351(6) 1 d PD A 1 Cl3B Cl 0.2353(3) 0.5114(2) 0.8614(2) 0.0175(4) Uani 0.649(6) 1 d PD A 2 O9B O 0.2952(8) 0.4982(7) 0.7518(4) 0.028(3) Uani 0.649(6) 1 d PD A 2 O10B O 0.3621(4) 0.4886(5) 0.9329(4) 0.0241(10) Uani 0.649(6) 1 d PD A 2 O11B O 0.1839(5) 0.6393(3) 0.9018(3) 0.0595(15) Uani 0.649(6) 1 d PD A 2 O12B O 0.1040(4) 0.4160(4) 0.8602(3) 0.0572(13) Uani 0.649(6) 1 d PD A 2 O1W O 0.08962(19) 0.09734(16) 0.70745(14) 0.0269(4) Uani 1 1 d D . . H11W H 0.023(3) 0.124(3) 0.7586(18) 0.040 Uiso 1 1 d D . . H12W H 0.055(3) 0.114(3) 0.6485(16) 0.040 Uiso 1 1 d D . . O2W O 0.9011(2) 0.19797(18) 0.88324(14) 0.0306(4) Uani 1 1 d D . . H21W H 0.968(5) 0.253(4) 0.921(4) 0.046 Uiso 0.649(6) 1 d PD . . H22W H 0.868(6) 0.135(3) 0.911(4) 0.046 Uiso 0.649(6) 1 d PD . . H23W H 0.968(9) 0.197(9) 0.937(6) 0.046 Uiso 0.351(6) 1 d PD . . H24W H 0.937(10) 0.272(5) 0.867(8) 0.046 Uiso 0.351(6) 1 d PD . . 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 S1 0.0198(3) 0.0181(2) 0.0140(3) 0.00463(18) 0.00260(18) 0.00416(18) N1 0.0199(8) 0.0158(8) 0.0130(8) 0.0013(6) 0.0026(7) 0.0010(7) N2 0.0150(8) 0.0181(8) 0.0160(9) 0.0047(7) 0.0012(6) 0.0001(6) N3 0.0155(8) 0.0169(8) 0.0145(8) 0.0027(6) 0.0027(6) 0.0019(6) C1 0.0167(10) 0.0177(9) 0.0137(10) 0.0034(8) 0.0016(7) -0.0012(8) C2 0.0184(10) 0.0225(10) 0.0166(10) 0.0043(8) -0.0019(8) 0.0002(8) C3 0.0158(9) 0.0205(10) 0.0206(11) 0.0021(8) 0.0023(8) 0.0023(8) C4 0.0189(10) 0.0148(9) 0.0171(10) 0.0018(8) 0.0043(8) -0.0006(7) C5 0.0250(11) 0.0147(9) 0.0171(10) 0.0027(8) 0.0050(8) -0.0020(8) C6 0.0185(10) 0.0144(9) 0.0151(10) 0.0017(8) 0.0004(8) 0.0007(7) C7 0.0184(10) 0.0181(10) 0.0147(10) 0.0021(8) 0.0008(8) -0.0007(8) C8 0.0200(10) 0.0202(10) 0.0191(11) 0.0086(8) -0.0012(8) -0.0017(8) C9 0.0154(10) 0.0177(10) 0.0228(11) 0.0078(8) -0.0005(8) 0.0002(7) C10 0.0163(9) 0.0171(9) 0.0145(10) 0.0028(8) 0.0010(7) -0.0018(7) Cl1 0.0212(3) 0.0231(3) 0.0174(3) 0.00664(19) 0.00211(18) 0.00258(18) O1 0.0254(8) 0.0310(9) 0.0289(9) 0.0043(7) 0.0013(7) 0.0105(7) O2 0.0236(8) 0.0353(9) 0.0289(9) 0.0060(7) 0.0109(6) 0.0032(7) O3 0.0286(9) 0.0427(10) 0.0277(9) 0.0193(8) 0.0043(7) 0.0054(7) O4 0.0518(11) 0.0268(9) 0.0256(9) 0.0039(7) -0.0090(8) -0.0046(8) Cl2 0.0160(2) 0.0244(3) 0.0184(3) 0.00738(19) 0.00306(18) 0.00533(18) O5 0.0331(9) 0.0499(11) 0.0207(8) 0.0141(8) 0.0099(7) 0.0171(8) O6 0.0197(8) 0.0386(9) 0.0245(8) 0.0106(7) 0.0025(6) 0.0129(7) O7 0.0413(10) 0.0359(9) 0.0301(9) 0.0190(7) 0.0136(7) 0.0188(8) O8 0.0283(9) 0.0467(11) 0.0601(13) -0.0041(10) -0.0044(9) -0.0075(8) Cl3A 0.0213(15) 0.029(2) 0.0118(11) -0.0005(13) -0.0003(9) 0.0050(13) O9A 0.060(12) 0.040(8) 0.020(8) 0.011(6) 0.004(7) 0.017(7) O10A 0.174(14) 0.033(4) 0.022(5) 0.011(3) 0.016(7) 0.036(6) O11A 0.096(6) 0.041(3) 0.019(3) 0.005(2) 0.011(3) -0.014(3) O12A 0.017(3) 0.181(13) 0.094(7) -0.066(7) -0.003(3) 0.012(5) Cl3B 0.0178(8) 0.0217(9) 0.0136(7) 0.0044(7) -0.0006(5) 0.0050(6) O9B 0.039(5) 0.037(4) 0.012(4) 0.007(3) 0.004(3) 0.018(3) O10B 0.0149(12) 0.044(2) 0.0138(18) 0.0039(16) -0.0016(10) 0.0146(13) O11B 0.096(4) 0.046(2) 0.044(2) 0.0106(16) 0.023(2) 0.052(2) O12B 0.0405(18) 0.087(3) 0.053(2) 0.045(2) -0.0191(15) -0.0303(18) O1W 0.0235(8) 0.0369(9) 0.0238(9) 0.0111(7) 0.0035(6) 0.0119(7) O2W 0.0239(8) 0.0419(10) 0.0282(9) 0.0113(8) 0.0016(7) 0.0075(7) _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 S1 C4 1.726(2) . ? S1 C1 1.728(2) . ? N1 C6 1.491(3) . ? N1 C5 1.509(2) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? N2 C7 1.490(3) . ? N2 C8 1.496(3) . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? N3 C9 1.500(3) . ? N3 C10 1.509(2) 2_656 ? N3 H3A 0.9000 . ? N3 H3B 0.9000 . ? C1 C2 1.360(3) . ? C1 C10 1.499(3) . ? C2 C3 1.418(3) . ? C2 H2 0.9300 . ? C3 C4 1.359(3) . ? C3 H3 0.9300 . ? C4 C5 1.497(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.519(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.516(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N3 1.509(2) 2_656 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? Cl1 O4 1.4331(17) . ? Cl1 O3 1.4356(17) . ? Cl1 O1 1.4448(16) . ? Cl1 O2 1.4531(16) . ? Cl2 O8 1.4300(19) . ? Cl2 O5 1.4311(17) . ? Cl2 O6 1.4372(15) . ? Cl2 O7 1.4395(17) . ? Cl3A O12A 1.406(5) . ? Cl3A O11A 1.418(5) . ? Cl3A O9A 1.435(5) . ? Cl3A O10A 1.439(6) . ? Cl3B O11B 1.418(3) . ? Cl3B O12B 1.427(3) . ? Cl3B O9B 1.429(4) . ? Cl3B O10B 1.444(3) . ? O1W H11W 0.854(17) . ? O1W H12W 0.846(17) . ? O2W H21W 0.831(19) . ? O2W H22W 0.848(19) . ? O2W H23W 0.87(2) . ? O2W H24W 0.89(2) . ? 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 S1 C1 91.61(10) . . ? C6 N1 C5 115.63(16) . . ? C6 N1 H1A 108.4 . . ? C5 N1 H1A 108.4 . . ? C6 N1 H1B 108.4 . . ? C5 N1 H1B 108.4 . . ? H1A N1 H1B 107.4 . . ? C7 N2 C8 112.45(15) . . ? C7 N2 H2A 109.1 . . ? C8 N2 H2A 109.1 . . ? C7 N2 H2B 109.1 . . ? C8 N2 H2B 109.1 . . ? H2A N2 H2B 107.8 . . ? C9 N3 C10 112.89(15) . 2_656 ? C9 N3 H3A 109.0 . . ? C10 N3 H3A 109.0 2_656 . ? C9 N3 H3B 109.0 . . ? C10 N3 H3B 109.0 2_656 . ? H3A N3 H3B 107.8 . . ? C2 C1 C10 126.74(19) . . ? C2 C1 S1 111.26(15) . . ? C10 C1 S1 121.92(15) . . ? C1 C2 C3 112.79(19) . . ? C1 C2 H2 123.6 . . ? C3 C2 H2 123.6 . . ? C4 C3 C2 113.04(18) . . ? C4 C3 H3 123.5 . . ? C2 C3 H3 123.5 . . ? C3 C4 C5 124.90(19) . . ? C3 C4 S1 111.26(15) . . ? C5 C4 S1 123.79(16) . . ? C4 C5 N1 113.64(16) . . ? C4 C5 H5A 108.8 . . ? N1 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? N1 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? N1 C6 C7 108.26(16) . . ? N1 C6 H6A 110.0 . . ? C7 C6 H6A 110.0 . . ? N1 C6 H6B 110.0 . . ? C7 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? N2 C7 C6 109.10(16) . . ? N2 C7 H7A 109.9 . . ? C6 C7 H7A 109.9 . . ? N2 C7 H7B 109.9 . . ? C6 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? N2 C8 C9 112.46(17) . . ? N2 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N2 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? N3 C9 C8 113.85(17) . . ? N3 C9 H9A 108.8 . . ? C8 C9 H9A 108.8 . . ? N3 C9 H9B 108.8 . . ? C8 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C1 C10 N3 113.01(15) . 2_656 ? C1 C10 H10A 109.0 . . ? N3 C10 H10A 109.0 2_656 . ? C1 C10 H10B 109.0 . . ? N3 C10 H10B 109.0 2_656 . ? H10A C10 H10B 107.8 . . ? O4 Cl1 O3 110.15(11) . . ? O4 Cl1 O1 110.16(10) . . ? O3 Cl1 O1 109.67(10) . . ? O4 Cl1 O2 109.03(11) . . ? O3 Cl1 O2 109.11(10) . . ? O1 Cl1 O2 108.68(10) . . ? O8 Cl2 O5 110.43(12) . . ? O8 Cl2 O6 109.42(11) . . ? O5 Cl2 O6 110.23(10) . . ? O8 Cl2 O7 108.58(13) . . ? O5 Cl2 O7 108.89(10) . . ? O6 Cl2 O7 109.26(10) . . ? O12A Cl3A O11A 111.3(5) . . ? O12A Cl3A O9A 110.0(5) . . ? O11A Cl3A O9A 109.3(5) . . ? O12A Cl3A O10A 110.0(5) . . ? O11A Cl3A O10A 107.7(5) . . ? O9A Cl3A O10A 108.4(5) . . ? O11B Cl3B O12B 110.0(3) . . ? O11B Cl3B O9B 109.9(3) . . ? O12B Cl3B O9B 109.7(3) . . ? O11B Cl3B O10B 109.7(3) . . ? O12B Cl3B O10B 108.4(2) . . ? O9B Cl3B O10B 109.1(3) . . ? H11W O1W H12W 108(2) . . ? H21W O2W H22W 116(3) . . ? H21W O2W H23W 46(5) . . ? H22W O2W H23W 73(5) . . ? H21W O2W H24W 55(5) . . ? H22W O2W H24W 169(6) . . ? H23W O2W H24W 100(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 C4 S1 C1 C2 1.70(16) . . . . ? C4 S1 C1 C10 178.79(16) . . . . ? C10 C1 C2 C3 -178.89(18) . . . . ? S1 C1 C2 C3 -2.0(2) . . . . ? C1 C2 C3 C4 1.3(3) . . . . ? C2 C3 C4 C5 177.51(18) . . . . ? C2 C3 C4 S1 0.1(2) . . . . ? C1 S1 C4 C3 -0.98(16) . . . . ? C1 S1 C4 C5 -178.47(17) . . . . ? C3 C4 C5 N1 118.2(2) . . . . ? S1 C4 C5 N1 -64.7(2) . . . . ? C6 N1 C5 C4 -38.9(2) . . . . ? C5 N1 C6 C7 -172.67(16) . . . . ? C8 N2 C7 C6 166.52(16) . . . . ? N1 C6 C7 N2 -167.80(15) . . . . ? C7 N2 C8 C9 -167.81(16) . . . . ? C10 N3 C9 C8 -161.13(16) 2_656 . . . ? N2 C8 C9 N3 -75.9(2) . . . . ? C2 C1 C10 N3 -95.8(2) . . . 2_656 ? S1 C1 C10 N3 87.63(19) . . . 2_656 ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 66.6 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.45 _refine_diff_density_min -0.37 _refine_diff_density_rms 0.063 # END OF CIF # Attachment 'PEAClO4.cif' data_JAMISCA_CLO4 _database_code_depnum_ccdc_archive 'CCDC 739058' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H42 N6, 4(Cl O4), H2 O' _chemical_formula_sum 'C24 H44 Cl4 N6 O17' _chemical_formula_weight 830.45 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' Cl Cl 0.1484 0.1585 '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' _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ' P 2ac 2ab ' _symmetry_cell_setting Orthorhombic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.9131(10) _cell_length_b 14.5341(15) _cell_length_c 20.786(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3599.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 90.0(5) _cell_measurement_reflns_used 4436 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.1 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1736 _exptl_absorpt_coefficient_mu 0.410 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.910 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(5) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'KappaCCD (with Oxford Cryostream)' _diffrn_measurement_method ' \w and \f scans ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 61377 _diffrn_reflns_av_R_equivalents 0.097 _diffrn_reflns_av_sigmaI/netI 0.0967 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.6 _diffrn_reflns_theta_max 27.1 _reflns_number_total 7932 _reflns_number_gt 5349 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (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^)+(0.0420P)^2^+1.0851P] 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 SHELXL _refine_ls_extinction_coef 0.0008(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack (1983) ' _refine_ls_abs_structure_Flack 0.28(5) _refine_ls_number_reflns 7932 _refine_ls_number_parameters 474 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.108 _refine_ls_R_factor_gt 0.051 _refine_ls_wR_factor_ref 0.105 _refine_ls_wR_factor_gt 0.089 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 N1 N 0.7333(2) 0.5534(2) 0.62094(15) 0.0178(7) Uani 1 1 d . . . H1N H 0.658(3) 0.580(2) 0.6227(18) 0.021 Uiso 1 1 d . . . N2 N 0.7703(2) 0.52398(19) 0.48392(16) 0.0186(7) Uani 1 1 d . . . H21N H 0.8444 0.5062 0.4848 0.022 Uiso 1 1 calc R . . H22N H 0.7297 0.4821 0.5076 0.022 Uiso 1 1 calc R . . N3 N 0.7020(2) 0.09166(19) 0.32201(15) 0.0196(7) Uani 1 1 d . . . H31N H 0.7337 0.0813 0.3617 0.024 Uiso 1 1 calc R . . H32N H 0.6288 0.1096 0.3284 0.024 Uiso 1 1 calc R . . N4 N 0.7069(3) -0.0868(2) 0.38118(17) 0.0222(8) Uani 1 1 d . . . H4N H 0.772(3) -0.101(3) 0.373(2) 0.027 Uiso 1 1 d . . . N5 N 0.7123(2) -0.05583(19) 0.51573(16) 0.0186(7) Uani 1 1 d . . . H51N H 0.6384 -0.0428 0.5248 0.022 Uiso 1 1 calc R . . H52N H 0.7372 -0.0134 0.4861 0.022 Uiso 1 1 calc R . . N6 N 0.7475(2) 0.3786(2) 0.68427(15) 0.0190(7) Uani 1 1 d . . . H61N H 0.8239 0.3708 0.6879 0.023 Uiso 1 1 calc R . . H62N H 0.7307 0.3847 0.6413 0.023 Uiso 1 1 calc R . . C1 C 0.8014(3) 0.6168(3) 0.5823(2) 0.0223(9) Uani 1 1 d . . . H1A H 0.8810 0.5974 0.5834 0.027 Uiso 1 1 calc R . . H1B H 0.7962 0.6797 0.6003 0.027 Uiso 1 1 calc R . . C2 C 0.7594(3) 0.6165(2) 0.51374(19) 0.0194(9) Uani 1 1 d . . . H2A H 0.6796 0.6355 0.5130 0.023 Uiso 1 1 calc R . . H2B H 0.8028 0.6617 0.4882 0.023 Uiso 1 1 calc R . . C3 C 0.7298(3) 0.5233(2) 0.41635(19) 0.0199(9) Uani 1 1 d . . . H3A H 0.7737 0.5684 0.3911 0.024 Uiso 1 1 calc R . . H3B H 0.6502 0.5430 0.4156 0.024 Uiso 1 1 calc R . . C4 C 0.7394(3) 0.4298(2) 0.38474(18) 0.0167(8) Uani 1 1 d . . . C5 C 0.6443(3) 0.3879(3) 0.35879(19) 0.0221(9) Uani 1 1 d . . . H5 H 0.5734 0.4174 0.3623 0.027 Uiso 1 1 calc R . . C6 C 0.6524(3) 0.3039(3) 0.3280(2) 0.0236(9) Uani 1 1 d . . . H6 H 0.5874 0.2773 0.3092 0.028 Uiso 1 1 calc R . . C7 C 0.7543(3) 0.2579(2) 0.32422(18) 0.0182(8) Uani 1 1 d . . . C8 C 0.8487(3) 0.2986(3) 0.35085(19) 0.0238(10) Uani 1 1 d . . . H8 H 0.9186 0.2673 0.3493 0.029 Uiso 1 1 calc R . . C9 C 0.8422(3) 0.3847(3) 0.37977(19) 0.0212(9) Uani 1 1 d . . . H9 H 0.9082 0.4130 0.3962 0.025 Uiso 1 1 calc R . . C10 C 0.7644(3) 0.1673(3) 0.2890(2) 0.0234(9) Uani 1 1 d . . . H10A H 0.7348 0.1745 0.2448 0.028 Uiso 1 1 calc R . . H10B H 0.8446 0.1502 0.2857 0.028 Uiso 1 1 calc R . . C11 C 0.7036(3) 0.0047(3) 0.2842(2) 0.0229(9) Uani 1 1 d . . . H11A H 0.7823 -0.0127 0.2748 0.028 Uiso 1 1 calc R . . H11B H 0.6644 0.0144 0.2428 0.028 Uiso 1 1 calc R . . C12 C 0.6468(3) -0.0723(3) 0.32104(19) 0.0225(9) Uani 1 1 d . . . H12A H 0.5677 -0.0559 0.3300 0.027 Uiso 1 1 calc R . . H12B H 0.6476 -0.1295 0.2951 0.027 Uiso 1 1 calc R . . C13 C 0.6563(3) -0.1530(3) 0.42469(19) 0.0229(9) Uani 1 1 d . . . H13A H 0.6603 -0.2155 0.4059 0.028 Uiso 1 1 calc R . . H13B H 0.5765 -0.1374 0.4320 0.028 Uiso 1 1 calc R . . C14 C 0.7199(3) -0.1499(2) 0.48723(19) 0.0194(9) Uani 1 1 d . . . H14A H 0.6881 -0.1955 0.5176 0.023 Uiso 1 1 calc R . . H14B H 0.7996 -0.1658 0.4796 0.023 Uiso 1 1 calc R . . C15 C 0.7804(3) -0.0468(3) 0.5763(2) 0.0223(9) Uani 1 1 d . . . H15A H 0.7622 -0.0983 0.6056 0.027 Uiso 1 1 calc R . . H15B H 0.8612 -0.0508 0.5655 0.027 Uiso 1 1 calc R . . C16 C 0.7576(3) 0.0425(2) 0.60957(18) 0.0189(9) Uani 1 1 d . . . C17 C 0.6606(3) 0.0544(3) 0.64561(19) 0.0214(9) Uani 1 1 d . . . H17 H 0.6076 0.0058 0.6485 0.026 Uiso 1 1 calc R . . C18 C 0.6403(3) 0.1367(2) 0.67745(18) 0.0194(9) Uani 1 1 d . . . H18 H 0.5735 0.1437 0.7020 0.023 Uiso 1 1 calc R . . C19 C 0.7164(3) 0.2088(2) 0.67379(18) 0.0174(9) Uani 1 1 d . . . C20 C 0.8144(3) 0.1962(3) 0.63819(19) 0.0208(9) Uani 1 1 d . . . H20 H 0.8685 0.2442 0.6362 0.025 Uiso 1 1 calc R . . C21 C 0.8337(3) 0.1146(2) 0.60584(18) 0.0192(9) Uani 1 1 d . . . H21 H 0.8999 0.1079 0.5807 0.023 Uiso 1 1 calc R . . C22 C 0.6894(3) 0.2952(3) 0.71028(19) 0.0205(9) Uani 1 1 d . . . H22A H 0.6073 0.3056 0.7090 0.025 Uiso 1 1 calc R . . H22B H 0.7112 0.2869 0.7559 0.025 Uiso 1 1 calc R . . C23 C 0.7140(3) 0.4646(3) 0.7188(2) 0.0224(9) Uani 1 1 d . . . H23A H 0.7363 0.4604 0.7646 0.027 Uiso 1 1 calc R . . H23B H 0.6315 0.4722 0.7168 0.027 Uiso 1 1 calc R . . C24 C 0.7704(3) 0.5460(3) 0.68803(19) 0.0231(9) Uani 1 1 d . . . H24A H 0.7507 0.6029 0.7117 0.028 Uiso 1 1 calc R . . H24B H 0.8530 0.5383 0.6896 0.028 Uiso 1 1 calc R . . Cl1 Cl 0.46997(7) 0.45498(6) 0.57966(5) 0.0227(2) Uani 1 1 d . . . O1 O 0.35741(18) 0.42555(17) 0.56271(13) 0.0233(6) Uani 1 1 d . . . O2 O 0.5287(2) 0.37930(17) 0.60826(13) 0.0294(7) Uani 1 1 d . . . O3 O 0.5264(2) 0.4853(2) 0.52286(14) 0.0388(8) Uani 1 1 d . . . O4 O 0.4635(2) 0.5286(2) 0.62601(17) 0.0470(9) Uani 1 1 d . . . Cl2 Cl 0.52387(7) 0.12667(6) 0.46116(4) 0.0195(2) Uani 1 1 d . . . O5 O 0.49841(19) 0.04276(16) 0.49719(12) 0.0230(6) Uani 1 1 d . . . O6 O 0.4678(2) 0.20412(16) 0.48990(13) 0.0254(6) Uani 1 1 d . . . O7 O 0.64379(18) 0.14036(18) 0.46163(13) 0.0246(6) Uani 1 1 d . . . O8 O 0.4860(2) 0.11364(17) 0.39565(11) 0.0261(6) Uani 1 1 d . . . Cl3 Cl 0.97972(7) 0.34588(6) 0.80431(4) 0.0202(2) Uani 1 1 d . . . O9 O 0.9809(2) 0.36417(17) 0.73509(11) 0.0240(6) Uani 1 1 d . . . O10 O 0.86550(19) 0.32853(18) 0.82313(13) 0.0276(7) Uani 1 1 d . . . O11 O 1.0220(2) 0.42519(18) 0.83713(13) 0.0331(7) Uani 1 1 d . . . O12 O 1.0475(2) 0.26760(19) 0.81745(14) 0.0409(8) Uani 1 1 d . . . Cl4 Cl 0.49450(7) -0.19186(6) 0.62383(5) 0.0273(2) Uani 1 1 d . . . O13 O 0.4959(2) -0.12239(16) 0.57339(13) 0.0278(6) Uani 1 1 d . . . O14 O 0.3893(2) -0.23944(18) 0.62343(15) 0.0328(7) Uani 1 1 d . . . O15 O 0.5067(3) -0.1457(2) 0.68458(14) 0.0550(9) Uani 1 1 d . . . O16 O 0.5862(2) -0.2531(2) 0.61480(19) 0.0618(11) Uani 1 1 d . . . O1W O 0.7275(2) 0.34353(19) 0.53654(14) 0.0271(7) Uani 1 1 d D . . H1W H 0.6589(19) 0.323(3) 0.538(2) 0.041 Uiso 1 1 d D . . H2W H 0.776(3) 0.304(2) 0.522(2) 0.041 Uiso 1 1 d 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 N1 0.0157(16) 0.0206(17) 0.017(2) 0.0020(15) -0.0021(14) -0.0025(14) N2 0.0174(16) 0.0158(17) 0.023(2) 0.0004(14) -0.0018(14) 0.0008(13) N3 0.0207(16) 0.0199(17) 0.018(2) -0.0030(15) -0.0016(14) 0.0013(13) N4 0.0191(16) 0.0256(18) 0.022(2) 0.0015(16) -0.0019(16) -0.0008(15) N5 0.0176(15) 0.0168(17) 0.021(2) -0.0007(15) 0.0024(14) -0.0008(13) N6 0.0209(16) 0.0230(17) 0.0133(19) -0.0028(15) -0.0024(13) 0.0026(14) C1 0.0215(19) 0.020(2) 0.025(3) -0.004(2) 0.0016(18) -0.0028(16) C2 0.0218(19) 0.0132(18) 0.023(2) 0.0006(18) 0.0040(17) 0.0006(16) C3 0.021(2) 0.021(2) 0.018(2) 0.0075(18) -0.0051(17) -0.0001(16) C4 0.0208(19) 0.0183(19) 0.011(2) 0.0041(17) 0.0004(16) -0.0016(16) C5 0.018(2) 0.027(2) 0.022(2) 0.0029(19) -0.0024(17) -0.0002(16) C6 0.020(2) 0.026(2) 0.025(2) -0.002(2) -0.0022(17) -0.0048(17) C7 0.022(2) 0.022(2) 0.011(2) 0.0011(17) 0.0021(16) 0.0019(17) C8 0.0168(19) 0.031(2) 0.024(3) 0.002(2) 0.0034(17) 0.0042(18) C9 0.0154(18) 0.028(2) 0.020(2) -0.0011(19) -0.0035(17) -0.0020(16) C10 0.022(2) 0.028(2) 0.020(2) -0.0003(19) 0.0022(17) 0.0003(17) C11 0.027(2) 0.022(2) 0.020(3) -0.0070(19) 0.0010(18) 0.0029(18) C12 0.028(2) 0.021(2) 0.019(2) -0.0041(18) -0.0015(18) 0.0031(17) C13 0.023(2) 0.021(2) 0.024(2) -0.003(2) 0.0012(18) -0.0037(17) C14 0.0205(19) 0.0149(19) 0.023(2) -0.0020(17) 0.0024(17) 0.0027(16) C15 0.0217(19) 0.026(2) 0.019(2) -0.0011(19) -0.0042(18) 0.0046(17) C16 0.0198(19) 0.0191(19) 0.018(2) 0.0014(17) -0.0058(17) 0.0011(17) C17 0.023(2) 0.019(2) 0.023(2) 0.0003(18) -0.0065(17) -0.0051(17) C18 0.0215(19) 0.023(2) 0.013(2) 0.0035(17) -0.0024(16) 0.0001(17) C19 0.0214(19) 0.018(2) 0.013(2) 0.0022(17) -0.0036(16) 0.0005(16) C20 0.0170(18) 0.021(2) 0.024(3) 0.0024(19) -0.0001(17) -0.0022(16) C21 0.0173(19) 0.022(2) 0.019(2) 0.0016(18) 0.0004(16) 0.0007(16) C22 0.0194(18) 0.025(2) 0.017(2) 0.0039(18) 0.0001(16) -0.0045(17) C23 0.027(2) 0.023(2) 0.017(2) -0.0033(18) -0.0027(17) -0.0006(18) C24 0.024(2) 0.024(2) 0.022(3) -0.0058(19) -0.0055(18) -0.0004(18) Cl1 0.0161(4) 0.0236(5) 0.0284(6) -0.0004(4) -0.0023(4) -0.0011(4) O1 0.0131(12) 0.0286(15) 0.0284(17) -0.0029(13) -0.0035(11) -0.0045(11) O2 0.0184(13) 0.0339(15) 0.0361(18) 0.0112(13) -0.0067(12) 0.0013(13) O3 0.0235(14) 0.060(2) 0.0330(18) 0.0215(15) 0.0003(14) -0.0107(14) O4 0.0255(15) 0.0449(18) 0.071(2) -0.0338(18) -0.0071(16) 0.0009(14) Cl2 0.0168(4) 0.0218(5) 0.0198(5) 0.0009(4) 0.0012(4) 0.0022(4) O5 0.0212(13) 0.0229(13) 0.0249(15) 0.0083(11) 0.0054(12) 0.0015(11) O6 0.0279(14) 0.0201(14) 0.0283(16) -0.0032(12) 0.0058(13) 0.0074(12) O7 0.0137(12) 0.0343(16) 0.0257(17) 0.0034(13) 0.0017(11) -0.0013(11) O8 0.0247(14) 0.0362(15) 0.0174(15) -0.0008(12) -0.0018(12) 0.0028(12) Cl3 0.0192(4) 0.0237(5) 0.0177(5) 0.0003(4) 0.0017(4) 0.0028(4) O9 0.0225(13) 0.0363(16) 0.0132(14) -0.0003(12) 0.0014(12) 0.0009(13) O10 0.0196(14) 0.0380(17) 0.0253(17) 0.0022(13) 0.0066(12) -0.0035(12) O11 0.0309(14) 0.0392(16) 0.0292(17) -0.0124(14) -0.0043(14) -0.0111(14) O12 0.0450(18) 0.0389(18) 0.039(2) 0.0149(15) 0.0065(14) 0.0249(14) Cl4 0.0210(5) 0.0285(5) 0.0323(6) 0.0059(5) 0.0031(4) -0.0027(4) O13 0.0239(14) 0.0287(14) 0.0308(16) 0.0130(13) 0.0000(12) -0.0006(12) O14 0.0232(14) 0.0324(16) 0.043(2) 0.0017(15) 0.0005(13) -0.0156(12) O15 0.066(2) 0.073(2) 0.0258(19) -0.0050(16) -0.0016(17) -0.0354(19) O16 0.0367(18) 0.056(2) 0.093(3) 0.040(2) 0.0297(19) 0.0250(17) O1W 0.0245(15) 0.0282(16) 0.0285(18) 0.0018(14) 0.0028(13) 0.0003(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 N1 C1 1.467(5) . ? N1 C24 1.467(5) . ? N1 H1N 0.98(3) . ? N2 C3 1.485(5) . ? N2 C2 1.487(4) . ? N2 H21N 0.9200 . ? N2 H22N 0.9200 . ? N3 C11 1.488(5) . ? N3 C10 1.493(5) . ? N3 H31N 0.9200 . ? N3 H32N 0.9200 . ? N4 C13 1.452(5) . ? N4 C12 1.456(5) . ? N4 H4N 0.82(4) . ? N5 C14 1.492(4) . ? N5 C15 1.503(5) . ? N5 H51N 0.9200 . ? N5 H52N 0.9200 . ? N6 C23 1.496(5) . ? N6 C22 1.496(4) . ? N6 H61N 0.9200 . ? N6 H62N 0.9200 . ? C1 C2 1.510(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.513(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C9 1.393(5) . ? C4 C5 1.394(5) . ? C5 C6 1.382(5) . ? C5 H5 0.9500 . ? C6 C7 1.388(5) . ? C6 H6 0.9500 . ? C7 C8 1.386(5) . ? C7 C10 1.512(5) . ? C8 C9 1.391(5) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.516(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.505(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.495(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C21 1.388(5) . ? C16 C17 1.389(5) . ? C17 C18 1.388(5) . ? C17 H17 0.9500 . ? C18 C19 1.388(5) . ? C18 H18 0.9500 . ? C19 C20 1.395(5) . ? C19 C22 1.502(5) . ? C20 C21 1.382(5) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.504(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? Cl1 O3 1.428(3) . ? Cl1 O2 1.433(3) . ? Cl1 O4 1.442(3) . ? Cl1 O1 1.451(2) . ? Cl2 O6 1.438(2) . ? Cl2 O7 1.442(2) . ? Cl2 O8 1.447(3) . ? Cl2 O5 1.463(2) . ? Cl3 O12 1.422(3) . ? Cl3 O11 1.431(3) . ? Cl3 O10 1.438(2) . ? Cl3 O9 1.463(3) . ? Cl4 O16 1.422(3) . ? Cl4 O14 1.432(3) . ? Cl4 O15 1.437(3) . ? Cl4 O13 1.456(3) . ? O1W H1W 0.869(19) . ? O1W H2W 0.874(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 C1 N1 C24 113.5(3) . . ? C1 N1 H1N 107(2) . . ? C24 N1 H1N 106(2) . . ? C3 N2 C2 111.8(3) . . ? C3 N2 H21N 109.2 . . ? C2 N2 H21N 109.2 . . ? C3 N2 H22N 109.2 . . ? C2 N2 H22N 109.2 . . ? H21N N2 H22N 107.9 . . ? C11 N3 C10 112.1(3) . . ? C11 N3 H31N 109.2 . . ? C10 N3 H31N 109.2 . . ? C11 N3 H32N 109.2 . . ? C10 N3 H32N 109.2 . . ? H31N N3 H32N 107.9 . . ? C13 N4 C12 115.2(3) . . ? C13 N4 H4N 111(3) . . ? C12 N4 H4N 109(3) . . ? C14 N5 C15 112.3(3) . . ? C14 N5 H51N 109.1 . . ? C15 N5 H51N 109.1 . . ? C14 N5 H52N 109.1 . . ? C15 N5 H52N 109.1 . . ? H51N N5 H52N 107.9 . . ? C23 N6 C22 112.3(3) . . ? C23 N6 H61N 109.1 . . ? C22 N6 H61N 109.1 . . ? C23 N6 H62N 109.1 . . ? C22 N6 H62N 109.1 . . ? H61N N6 H62N 107.9 . . ? N1 C1 C2 109.4(3) . . ? N1 C1 H1A 109.8 . . ? C2 C1 H1A 109.8 . . ? N1 C1 H1B 109.8 . . ? C2 C1 H1B 109.8 . . ? H1A C1 H1B 108.2 . . ? N2 C2 C1 111.5(3) . . ? N2 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? N2 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? N2 C3 C4 113.1(3) . . ? N2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? N2 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C9 C4 C5 118.7(3) . . ? C9 C4 C3 121.4(3) . . ? C5 C4 C3 119.9(3) . . ? C6 C5 C4 120.5(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 120.9(3) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 118.8(3) . . ? C8 C7 C10 120.1(3) . . ? C6 C7 C10 121.1(3) . . ? C7 C8 C9 120.8(3) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C8 C9 C4 120.2(3) . . ? C8 C9 H9 119.9 . . ? C4 C9 H9 119.9 . . ? N3 C10 C7 112.3(3) . . ? N3 C10 H10A 109.2 . . ? C7 C10 H10A 109.2 . . ? N3 C10 H10B 109.2 . . ? C7 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? N3 C11 C12 110.8(3) . . ? N3 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? N3 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? N4 C12 C11 108.7(3) . . ? N4 C12 H12A 109.9 . . ? C11 C12 H12A 109.9 . . ? N4 C12 H12B 109.9 . . ? C11 C12 H12B 109.9 . . ? H12A C12 H12B 108.3 . . ? N4 C13 C14 108.0(3) . . ? N4 C13 H13A 110.1 . . ? C14 C13 H13A 110.1 . . ? N4 C13 H13B 110.1 . . ? C14 C13 H13B 110.1 . . ? H13A C13 H13B 108.4 . . ? N5 C14 C13 109.9(3) . . ? N5 C14 H14A 109.7 . . ? C13 C14 H14A 109.7 . . ? N5 C14 H14B 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C16 C15 N5 111.4(3) . . ? C16 C15 H15A 109.3 . . ? N5 C15 H15A 109.3 . . ? C16 C15 H15B 109.3 . . ? N5 C15 H15B 109.3 . . ? H15A C15 H15B 108.0 . . ? C21 C16 C17 118.7(3) . . ? C21 C16 C15 120.7(3) . . ? C17 C16 C15 120.6(3) . . ? C18 C17 C16 120.7(3) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 120.7(3) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C18 C19 C20 118.5(3) . . ? C18 C19 C22 117.7(3) . . ? C20 C19 C22 123.8(3) . . ? C21 C20 C19 120.7(3) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C16 120.8(3) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? N6 C22 C19 113.3(3) . . ? N6 C22 H22A 108.9 . . ? C19 C22 H22A 108.9 . . ? N6 C22 H22B 108.9 . . ? C19 C22 H22B 108.9 . . ? H22A C22 H22B 107.7 . . ? N6 C23 C24 109.5(3) . . ? N6 C23 H23A 109.8 . . ? C24 C23 H23A 109.8 . . ? N6 C23 H23B 109.8 . . ? C24 C23 H23B 109.8 . . ? H23A C23 H23B 108.2 . . ? N1 C24 C23 109.1(3) . . ? N1 C24 H24A 109.9 . . ? C23 C24 H24A 109.9 . . ? N1 C24 H24B 109.9 . . ? C23 C24 H24B 109.9 . . ? H24A C24 H24B 108.3 . . ? O3 Cl1 O2 110.46(16) . . ? O3 Cl1 O4 110.41(19) . . ? O2 Cl1 O4 108.59(18) . . ? O3 Cl1 O1 108.97(17) . . ? O2 Cl1 O1 109.03(15) . . ? O4 Cl1 O1 109.36(15) . . ? O6 Cl2 O7 110.42(15) . . ? O6 Cl2 O8 110.39(16) . . ? O7 Cl2 O8 109.47(16) . . ? O6 Cl2 O5 110.09(15) . . ? O7 Cl2 O5 108.47(15) . . ? O8 Cl2 O5 107.93(15) . . ? O12 Cl3 O11 110.69(18) . . ? O12 Cl3 O10 110.18(17) . . ? O11 Cl3 O10 110.13(16) . . ? O12 Cl3 O9 109.21(16) . . ? O11 Cl3 O9 108.60(16) . . ? O10 Cl3 O9 107.96(16) . . ? O16 Cl4 O14 111.69(18) . . ? O16 Cl4 O15 109.3(2) . . ? O14 Cl4 O15 108.60(19) . . ? O16 Cl4 O13 109.28(17) . . ? O14 Cl4 O13 109.95(16) . . ? O15 Cl4 O13 107.91(18) . . ? H1W O1W H2W 114(4) . . ? 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 C24 N1 C1 C2 177.7(3) . . . . ? C3 N2 C2 C1 -179.7(3) . . . . ? N1 C1 C2 N2 -61.9(4) . . . . ? C2 N2 C3 C4 -179.7(3) . . . . ? N2 C3 C4 C9 -57.9(5) . . . . ? N2 C3 C4 C5 123.3(4) . . . . ? C9 C4 C5 C6 -0.9(6) . . . . ? C3 C4 C5 C6 178.0(3) . . . . ? C4 C5 C6 C7 2.3(6) . . . . ? C5 C6 C7 C8 -1.3(6) . . . . ? C5 C6 C7 C10 -178.3(4) . . . . ? C6 C7 C8 C9 -1.2(6) . . . . ? C10 C7 C8 C9 175.8(4) . . . . ? C7 C8 C9 C4 2.7(6) . . . . ? C5 C4 C9 C8 -1.6(5) . . . . ? C3 C4 C9 C8 179.6(4) . . . . ? C11 N3 C10 C7 174.9(3) . . . . ? C8 C7 C10 N3 115.5(4) . . . . ? C6 C7 C10 N3 -67.6(5) . . . . ? C10 N3 C11 C12 176.0(3) . . . . ? C13 N4 C12 C11 174.6(3) . . . . ? N3 C11 C12 N4 -60.3(4) . . . . ? C12 N4 C13 C14 -172.5(3) . . . . ? C15 N5 C14 C13 -176.4(3) . . . . ? N4 C13 C14 N5 60.6(4) . . . . ? C14 N5 C15 C16 -171.1(3) . . . . ? N5 C15 C16 C21 -103.4(4) . . . . ? N5 C15 C16 C17 77.5(4) . . . . ? C21 C16 C17 C18 -0.2(5) . . . . ? C15 C16 C17 C18 178.9(3) . . . . ? C16 C17 C18 C19 0.2(6) . . . . ? C17 C18 C19 C20 -0.9(5) . . . . ? C17 C18 C19 C22 -179.2(3) . . . . ? C18 C19 C20 C21 1.8(5) . . . . ? C22 C19 C20 C21 179.9(3) . . . . ? C19 C20 C21 C16 -1.9(6) . . . . ? C17 C16 C21 C20 1.1(5) . . . . ? C15 C16 C21 C20 -178.0(3) . . . . ? C23 N6 C22 C19 176.5(3) . . . . ? C18 C19 C22 N6 -157.2(3) . . . . ? C20 C19 C22 N6 24.7(5) . . . . ? C22 N6 C23 C24 -176.9(3) . . . . ? C1 N1 C24 C23 -166.9(3) . . . . ? N6 C23 C24 N1 61.6(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O4 0.98(3) 2.43(3) 3.236(4) 139(3) . N1 H1N O16 0.98(3) 2.58(3) 3.316(4) 132(3) 1_565 N2 H21N O5 0.92 2.00 2.911(4) 169.3 3_556 N2 H22N O1W 0.92 2.10 2.887(4) 142.5 . N2 H22N O3 0.92 2.44 3.069(4) 125.3 . N3 H31N O1 0.92 2.16 3.038(4) 160.3 3_556 N3 H31N O7 0.92 2.49 3.067(4) 121.0 . N3 H32N O8 0.92 2.20 3.011(4) 146.2 . N3 H32N O9 0.92 2.23 2.960(4) 135.4 3_456 N4 H4N O4 0.82(4) 2.50(4) 3.174(4) 139(3) 3_556 N5 H51N O5 0.92 2.16 2.949(4) 143.5 . N5 H51N O13 0.92 2.29 3.002(4) 134.1 . N5 H52N O1 0.92 2.17 3.039(4) 156.8 3_556 N5 H52N O7 0.92 2.55 3.172(4) 125.5 . N6 H61N O9 0.92 2.11 2.982(4) 156.7 . N6 H61N O8 0.92 2.61 3.293(4) 131.9 3_556 N6 H62N O1W 0.92 2.26 3.122(4) 156.2 . N6 H62N O2 0.92 2.50 3.048(4) 118.2 . O1W H1W O2 0.869(19) 2.28(4) 2.846(4) 123(4) . O1W H2W O6 0.874(19) 2.30(3) 2.997(3) 137(3) 3_556 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.55 _refine_diff_density_min -0.41 _refine_diff_density_rms 0.080 # END OF CIF