# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_update_record ; 2013-09-02 # Formatted by publCIF ; # publcif _publ_body_element loop end _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common '[CuL2](ClO4)2' _chemical_melting_point ? _chemical_formula_moiety 'C30 H40 Cu N8 O4, 2(Cl O4)' _chemical_formula_sum 'C30 H40 Cl2 Cu N8 O12' _chemical_formula_weight 839.15 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.390(5) _cell_length_b 10.293(5) _cell_length_c 10.426(5) _cell_angle_alpha 101.979(4) _cell_angle_beta 108.296(5) _cell_angle_gamma 106.798(5) _cell_volume 865.2(7) _cell_formula_units_Z 1 _cell_measurement_temperature 110.0(1) _cell_measurement_reflns_used 21737 _cell_measurement_theta_min 3.2106 _cell_measurement_theta_max 33.0227 _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 435 _exptl_absorpt_coefficient_mu 0.864 _exptl_absorpt_correction_T_min 0.82667 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ? _diffrn_ambient_temperature 110.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4508 _diffrn_reflns_number 41373 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0718 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.2106 _diffrn_reflns_theta_max 28.000 _reflns_number_total 4169 _reflns_number_gt 3866 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution SIR2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0336P)^2^+0.5393P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4169 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0274 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0678 _refine_ls_wR_factor_gt 0.0661 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 H1A H 0.232(2) -0.1918(18) 0.2243(18) 0.011(4) Uiso 1 1 d . . . H1B H 0.260(2) -0.1591(17) 0.0942(18) 0.012(4) Uiso 1 1 d . . . Cu1 Cu 0.0000 0.0000 0.0000 0.00922(7) Uani 1 2 d S . . O3 O -0.07440(12) -0.35319(10) 0.10291(10) 0.01497(19) Uani 1 1 d . . . O1 O -0.25873(11) -0.21782(10) -0.08204(10) 0.01426(19) Uani 1 1 d . . . N1 N 0.06139(13) -0.08882(11) -0.15508(11) 0.0112(2) Uani 1 1 d . . . N2 N -0.15101(13) 0.03922(11) -0.17093(11) 0.0102(2) Uani 1 1 d . . . N5 N 0.13484(13) -0.17954(12) -0.17033(12) 0.0122(2) Uani 1 1 d . . . N6 N 0.11783(13) -0.21246(12) -0.30654(11) 0.0110(2) Uani 1 1 d . . . C1 C 0.18182(16) -0.17434(14) 0.13557(14) 0.0124(2) Uani 1 1 d . . . C2 C 0.03317(16) -0.30634(14) 0.03559(14) 0.0140(2) Uani 1 1 d . . . H2A H -0.0241 -0.2852 -0.0475 0.017 Uiso 1 1 calc R . . H2B H 0.0667 -0.3833 0.0031 0.017 Uiso 1 1 calc R . . C3 C -0.24076(17) -0.41612(15) 0.00496(16) 0.0181(3) Uani 1 1 d . . . H3A H -0.3003 -0.4881 0.0361 0.022 Uiso 1 1 calc R . . H3B H -0.2478 -0.4644 -0.0885 0.022 Uiso 1 1 calc R . . C4 C -0.31999(17) -0.30863(16) -0.00826(16) 0.0191(3) Uani 1 1 d . . . H4A H -0.4364 -0.3591 -0.0600 0.023 Uiso 1 1 calc R . . H4B H -0.2995 -0.2500 0.0864 0.023 Uiso 1 1 calc R . . C5 C -0.36508(15) -0.14805(15) -0.13636(15) 0.0146(3) Uani 1 1 d . . . H5A H -0.3578 -0.0721 -0.0588 0.018 Uiso 1 1 calc R . . H5B H -0.4765 -0.2166 -0.1842 0.018 Uiso 1 1 calc R . . C6 C -0.31187(15) -0.08661(14) -0.24023(14) 0.0130(2) Uani 1 1 d . . . H6A H -0.3942 -0.0563 -0.2930 0.016 Uiso 1 1 calc R . . H6B H -0.3045 -0.1617 -0.3084 0.016 Uiso 1 1 calc R . . C7 C -0.07916(16) 0.04111(14) -0.28048(13) 0.0117(2) Uani 1 1 d . . . H7A H -0.1635 0.0156 -0.3744 0.014 Uiso 1 1 calc R . . H7B H -0.0003 0.1365 -0.2577 0.014 Uiso 1 1 calc R . . C8 C 0.00039(15) -0.06411(13) -0.27983(13) 0.0108(2) Uani 1 1 d . . . C9 C 0.03536(15) -0.14415(14) -0.37868(14) 0.0118(2) Uani 1 1 d . . . H9 H 0.0085 -0.1503 -0.4741 0.014 Uiso 1 1 calc R . . C10 C 0.18292(15) -0.31125(14) -0.36021(14) 0.0117(2) Uani 1 1 d . . . C11 C 0.17524(16) -0.42869(14) -0.31240(15) 0.0152(3) Uani 1 1 d . . . H11 H 0.1281 -0.4434 -0.2477 0.018 Uiso 1 1 calc R . . C12 C 0.23949(18) -0.52322(15) -0.36345(16) 0.0193(3) Uani 1 1 d . . . H12 H 0.2378 -0.6012 -0.3313 0.023 Uiso 1 1 calc R . . C13 C 0.30642(18) -0.50197(16) -0.46258(17) 0.0218(3) Uani 1 1 d . . . H13 H 0.3480 -0.5666 -0.4973 0.026 Uiso 1 1 calc R . . C15 C 0.25100(16) -0.28709(15) -0.45742(15) 0.0157(3) Uani 1 1 d . . . H15 H 0.2561 -0.2071 -0.4868 0.019 Uiso 1 1 calc R . . C14 C 0.31164(18) -0.38465(16) -0.51020(16) 0.0200(3) Uani 1 1 d . . . H14 H 0.3556 -0.3715 -0.5772 0.024 Uiso 1 1 calc R . . Cl1 Cl 0.40218(4) 0.15437(3) 0.69192(3) 0.01240(8) Uani 1 1 d . . . O21 O 0.40901(13) 0.07327(12) 0.78925(12) 0.0217(2) Uani 1 1 d . . . O22 O 0.44256(14) 0.09080(13) 0.57860(11) 0.0253(2) Uani 1 1 d . . . O23 O 0.51392(13) 0.30053(11) 0.76665(13) 0.0258(2) Uani 1 1 d . . . O24 O 0.23934(12) 0.15174(11) 0.63127(11) 0.0187(2) 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 Cu1 0.00927(11) 0.01038(11) 0.00852(11) 0.00297(8) 0.00278(8) 0.00538(8) O3 0.0146(4) 0.0143(4) 0.0154(4) 0.0064(4) 0.0058(4) 0.0038(4) O1 0.0115(4) 0.0151(4) 0.0180(5) 0.0089(4) 0.0058(4) 0.0055(4) N1 0.0112(5) 0.0109(5) 0.0116(5) 0.0036(4) 0.0039(4) 0.0052(4) N2 0.0093(5) 0.0098(5) 0.0108(5) 0.0029(4) 0.0032(4) 0.0038(4) N5 0.0132(5) 0.0133(5) 0.0116(5) 0.0037(4) 0.0054(4) 0.0070(4) N6 0.0115(5) 0.0110(5) 0.0104(5) 0.0029(4) 0.0046(4) 0.0042(4) C1 0.0126(6) 0.0124(6) 0.0146(6) 0.0053(5) 0.0053(5) 0.0076(5) C2 0.0173(6) 0.0106(6) 0.0157(6) 0.0045(5) 0.0081(5) 0.0058(5) C3 0.0159(6) 0.0138(6) 0.0200(7) 0.0073(5) 0.0048(5) 0.0005(5) C4 0.0156(6) 0.0240(7) 0.0226(7) 0.0141(6) 0.0102(5) 0.0069(6) C5 0.0093(6) 0.0159(6) 0.0177(6) 0.0065(5) 0.0037(5) 0.0047(5) C6 0.0089(5) 0.0129(6) 0.0131(6) 0.0032(5) 0.0012(5) 0.0028(5) C7 0.0138(6) 0.0123(6) 0.0113(5) 0.0048(5) 0.0057(5) 0.0067(5) C8 0.0093(5) 0.0103(5) 0.0109(5) 0.0036(4) 0.0028(4) 0.0024(4) C9 0.0109(5) 0.0123(6) 0.0119(6) 0.0046(5) 0.0035(5) 0.0048(5) C10 0.0100(5) 0.0109(6) 0.0123(6) 0.0012(4) 0.0027(4) 0.0050(5) C11 0.0153(6) 0.0136(6) 0.0165(6) 0.0045(5) 0.0062(5) 0.0059(5) C12 0.0199(7) 0.0132(6) 0.0243(7) 0.0055(5) 0.0067(6) 0.0082(5) C13 0.0203(7) 0.0179(7) 0.0272(7) 0.0010(6) 0.0107(6) 0.0107(6) C15 0.0154(6) 0.0155(6) 0.0160(6) 0.0050(5) 0.0063(5) 0.0059(5) C14 0.0191(7) 0.0218(7) 0.0206(7) 0.0036(6) 0.0117(6) 0.0081(6) Cl1 0.01102(14) 0.01231(14) 0.01221(14) 0.00282(11) 0.00335(11) 0.00441(11) O21 0.0202(5) 0.0263(5) 0.0234(5) 0.0155(4) 0.0077(4) 0.0116(4) O22 0.0292(6) 0.0349(6) 0.0161(5) 0.0047(5) 0.0104(4) 0.0195(5) O23 0.0196(5) 0.0146(5) 0.0301(6) 0.0008(4) 0.0051(5) -0.0014(4) O24 0.0126(4) 0.0198(5) 0.0236(5) 0.0089(4) 0.0041(4) 0.0082(4) _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 Cu1 N1 2.0145(13) . ? Cu1 N1 2.0145(13) 2 ? Cu1 N2 2.0958(13) . ? Cu1 N2 2.0958(13) 2 ? O3 C3 1.4289(18) . ? O3 C2 1.4316(17) . ? O1 C4 1.4358(17) . ? O1 C5 1.4360(16) . ? N1 N5 1.3239(16) . ? N1 C8 1.3558(17) . ? N2 C1 1.4968(17) 2 ? N2 C7 1.4986(17) . ? N2 C6 1.5088(17) . ? N5 N6 1.3355(16) . ? N6 C9 1.3521(17) . ? N6 C10 1.4347(16) . ? C1 N2 1.4968(17) 2 ? C1 C2 1.5111(19) . ? C1 H1A 0.977(17) . ? C1 H1B 0.950(17) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.507(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.5046(19) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.4827(18) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.3657(18) . ? C9 H9 0.9300 . ? C10 C15 1.385(2) . ? C10 C11 1.3918(19) . ? C11 C12 1.3857(19) . ? C11 H11 0.9300 . ? C12 C13 1.390(2) . ? C12 H12 0.9300 . ? C13 C14 1.392(2) . ? C13 H13 0.9300 . ? C15 C14 1.390(2) . ? C15 H15 0.9300 . ? C14 H14 0.9300 . ? Cl1 O23 1.4349(12) . ? Cl1 O22 1.4393(12) . ? Cl1 O21 1.4396(12) . ? Cl1 O24 1.4493(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 180.00(5) . 2 ? N1 Cu1 N2 81.10(6) . . ? N1 Cu1 N2 98.90(6) 2 . ? N1 Cu1 N2 98.90(6) . 2 ? N1 Cu1 N2 81.10(6) 2 2 ? N2 Cu1 N2 180.00(6) . 2 ? C3 O3 C2 112.39(11) . . ? C4 O1 C5 111.89(11) . . ? N5 N1 C8 110.26(11) . . ? N5 N1 Cu1 134.87(9) . . ? C8 N1 Cu1 114.43(9) . . ? C1 N2 C7 108.52(10) 2 . ? C1 N2 C6 108.46(10) 2 . ? C7 N2 C6 106.72(10) . . ? C1 N2 Cu1 116.59(8) 2 . ? C7 N2 Cu1 108.33(8) . . ? C6 N2 Cu1 107.81(8) . . ? N1 N5 N6 105.40(10) . . ? N5 N6 C9 112.18(11) . . ? N5 N6 C10 120.06(11) . . ? C9 N6 C10 127.76(11) . . ? N2 C1 C2 114.86(11) 2 . ? N2 C1 H1A 108.8(10) 2 . ? C2 C1 H1A 109.1(10) . . ? N2 C1 H1B 108.2(10) 2 . ? C2 C1 H1B 109.1(10) . . ? H1A C1 H1B 106.5(14) . . ? O3 C2 C1 112.07(11) . . ? O3 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? O3 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? O3 C3 C4 113.43(12) . . ? O3 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? O3 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? O1 C4 C3 111.07(12) . . ? O1 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? O1 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? O1 C5 C6 107.02(11) . . ? O1 C5 H5A 110.3 . . ? C6 C5 H5A 110.3 . . ? O1 C5 H5B 110.3 . . ? C6 C5 H5B 110.3 . . ? H5A C5 H5B 108.6 . . ? C5 C6 N2 114.03(11) . . ? C5 C6 H6A 108.7 . . ? N2 C6 H6A 108.7 . . ? C5 C6 H6B 108.7 . . ? N2 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C8 C7 N2 108.14(10) . . ? C8 C7 H7A 110.1 . . ? N2 C7 H7A 110.1 . . ? C8 C7 H7B 110.1 . . ? N2 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? N1 C8 C9 107.70(12) . . ? N1 C8 C7 117.65(11) . . ? C9 C8 C7 134.59(12) . . ? N6 C9 C8 104.45(12) . . ? N6 C9 H9 127.8 . . ? C8 C9 H9 127.8 . . ? C15 C10 C11 122.18(12) . . ? C15 C10 N6 119.25(12) . . ? C11 C10 N6 118.56(12) . . ? C12 C11 C10 118.44(13) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? C11 C12 C13 120.28(14) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 120.46(13) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C10 C15 C14 118.73(13) . . ? C10 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C15 C14 C13 119.88(14) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? O23 Cl1 O22 109.88(8) . . ? O23 Cl1 O21 109.94(8) . . ? O22 Cl1 O21 109.41(7) . . ? O23 Cl1 O24 109.11(7) . . ? O22 Cl1 O24 109.18(7) . . ? O21 Cl1 O24 109.30(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 N1 N5 -28.81(12) 2 . . . ? N2 Cu1 N1 N5 -162.68(13) . . . . ? N2 Cu1 N1 N5 17.32(13) 2 . . . ? N1 Cu1 N1 C8 142.70(14) 2 . . . ? N2 Cu1 N1 C8 8.83(9) . . . . ? N2 Cu1 N1 C8 -171.17(9) 2 . . . ? N1 Cu1 N2 C1 -146.76(9) . . . 2 ? N1 Cu1 N2 C1 33.24(9) 2 . . 2 ? N2 Cu1 N2 C1 109(45) 2 . . 2 ? N1 Cu1 N2 C7 -24.08(8) . . . . ? N1 Cu1 N2 C7 155.92(8) 2 . . . ? N2 Cu1 N2 C7 -128(45) 2 . . . ? N1 Cu1 N2 C6 91.06(9) . . . . ? N1 Cu1 N2 C6 -88.94(9) 2 . . . ? N2 Cu1 N2 C6 -13(45) 2 . . . ? C8 N1 N5 N6 -0.57(14) . . . . ? Cu1 N1 N5 N6 171.20(9) . . . . ? N1 N5 N6 C9 0.22(14) . . . . ? N1 N5 N6 C10 -179.30(11) . . . . ? C3 O3 C2 C1 147.17(11) . . . . ? N2 C1 C2 O3 -70.56(14) 2 . . . ? C2 O3 C3 C4 -88.72(14) . . . . ? C5 O1 C4 C3 161.24(11) . . . . ? O3 C3 C4 O1 70.72(16) . . . . ? C4 O1 C5 C6 -166.38(11) . . . . ? O1 C5 C6 N2 -70.04(14) . . . . ? C1 N2 C6 C5 -90.16(13) 2 . . . ? C7 N2 C6 C5 153.11(11) . . . . ? Cu1 N2 C6 C5 36.91(12) . . . . ? C1 N2 C7 C8 161.46(10) 2 . . . ? C6 N2 C7 C8 -81.84(12) . . . . ? Cu1 N2 C7 C8 34.00(11) . . . . ? N5 N1 C8 C9 0.71(14) . . . . ? Cu1 N1 C8 C9 -172.89(8) . . . . ? N5 N1 C8 C7 -176.99(11) . . . . ? Cu1 N1 C8 C7 9.41(14) . . . . ? N2 C7 C8 N1 -29.62(15) . . . . ? N2 C7 C8 C9 153.46(14) . . . . ? N5 N6 C9 C8 0.20(14) . . . . ? C10 N6 C9 C8 179.68(12) . . . . ? N1 C8 C9 N6 -0.54(14) . . . . ? C7 C8 C9 N6 176.60(14) . . . . ? N5 N6 C10 C15 -142.68(13) . . . . ? C9 N6 C10 C15 37.88(19) . . . . ? N5 N6 C10 C11 37.34(17) . . . . ? C9 N6 C10 C11 -142.10(13) . . . . ? C15 C10 C11 C12 0.6(2) . . . . ? N6 C10 C11 C12 -179.44(12) . . . . ? C10 C11 C12 C13 -1.4(2) . . . . ? C11 C12 C13 C14 0.9(2) . . . . ? C11 C10 C15 C14 0.9(2) . . . . ? N6 C10 C15 C14 -179.11(12) . . . . ? C10 C15 C14 C13 -1.5(2) . . . . ? C12 C13 C14 C15 0.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.412 _refine_diff_density_min -0.448 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 853231' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_update_record ; 2013-09-02 # Formatted by publCIF ; # publcif _publ_body_element loop end _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common '[CuL3](ClO4)2' _chemical_melting_point ? _chemical_formula_moiety 'C32 H44 Cu N8 O6, 2(Cl O4)' _chemical_formula_sum 'C32 H44 Cl2 Cu N8 O14' _chemical_formula_weight 899.20 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.383(5) _cell_length_b 10.299(8) _cell_length_c 11.300(9) _cell_angle_alpha 70.19(4) _cell_angle_beta 66.08(3) _cell_angle_gamma 73.30(5) _cell_volume 924.7(12) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4065 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 27.83 _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.310 _exptl_crystal_size_mid 0.190 _exptl_crystal_size_min 0.110 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 467 _exptl_absorpt_coefficient_mu 0.816 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 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 KappaAPEX _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 4383 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.83 _reflns_number_total 4383 _reflns_number_gt 4065 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2, Bruker (2007). Program name(s). Bruker AXS Inc., Madison, Wisconsin, USA' _computing_cell_refinement 'Apex2, Bruker (2007). Program name(s). Bruker AXS Inc., Madison, Wisconsin, USA' _computing_data_reduction 'Apex2, Bruker (2007). Program name(s). Bruker AXS Inc., Madison, Wisconsin, USA' _computing_structure_solution 'SIR92, Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435' _computing_structure_refinement 'SHELXL-97 Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122' _computing_molecular_graphics ? _computing_publication_material 'WinGX Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854' _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^)+(0.0321P)^2^+1.3518P] 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 4383 _refine_ls_number_parameters 260 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0839 _refine_ls_wR_factor_gt 0.0806 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 Cu1 Cu 0.0000 0.0000 0.5000 0.00859(8) Uani 1 2 d S . . O3 O -0.15998(15) 0.35925(13) 0.60089(13) 0.0143(3) Uani 1 1 d . . . O1 O -0.19121(15) 0.21246(13) 0.42275(13) 0.0129(3) Uani 1 1 d . . . O4 O 0.80621(16) 0.54934(14) -0.02451(14) 0.0189(3) Uani 1 1 d . . . N1 N 0.19078(17) 0.07512(15) 0.35522(15) 0.0104(3) Uani 1 1 d . . . N2 N -0.01153(17) -0.05182(15) 0.33943(14) 0.0098(3) Uani 1 1 d . . . N5 N 0.28006(17) 0.16235(16) 0.34130(15) 0.0111(3) Uani 1 1 d . . . N6 N 0.37432(17) 0.18504(15) 0.21293(15) 0.0101(3) Uani 1 1 d . . . C1 C 0.0716(2) 0.18439(18) 0.62618(17) 0.0115(3) Uani 1 1 d . . . H1A H 0.1882 0.1665 0.5834 0.014 Uiso 1 1 calc R . . H1B H 0.0477 0.2096 0.7102 0.014 Uiso 1 1 calc R . . C2 C 0.0035(2) 0.30817(18) 0.53415(18) 0.0130(3) Uani 1 1 d . . . H2A H 0.0653 0.3844 0.5017 0.016 Uiso 1 1 calc R . . H2B H 0.0129 0.2799 0.4554 0.016 Uiso 1 1 calc R . . C3 C -0.2503(2) 0.41290(19) 0.51334(19) 0.0169(4) Uani 1 1 d . . . H3A H -0.1826 0.4593 0.4239 0.020 Uiso 1 1 calc R . . H3B H -0.3398 0.4851 0.5475 0.020 Uiso 1 1 calc R . . C4 C -0.3150(2) 0.3033(2) 0.4985(2) 0.0177(4) Uani 1 1 d . . . H4A H -0.3694 0.2467 0.5883 0.021 Uiso 1 1 calc R . . H4B H -0.3939 0.3500 0.4530 0.021 Uiso 1 1 calc R . . C5 C -0.2540(2) 0.13855(19) 0.37292(19) 0.0137(3) Uani 1 1 d . . . H5A H -0.3273 0.2046 0.3275 0.016 Uiso 1 1 calc R . . H5B H -0.3127 0.0679 0.4474 0.016 Uiso 1 1 calc R . . C6 C -0.1153(2) 0.06800(18) 0.27559(18) 0.0130(3) Uani 1 1 d . . . H6A H -0.1557 0.0326 0.2260 0.016 Uiso 1 1 calc R . . H6B H -0.0499 0.1387 0.2097 0.016 Uiso 1 1 calc R . . C7 C 0.1505(2) -0.06112(18) 0.23579(17) 0.0115(3) Uani 1 1 d . . . H7A H 0.2118 -0.1567 0.2557 0.014 Uiso 1 1 calc R . . H7B H 0.1428 -0.0408 0.1462 0.014 Uiso 1 1 calc R . . C8 C 0.2304(2) 0.04279(18) 0.23787(17) 0.0111(3) Uani 1 1 d . . . C9 C 0.3467(2) 0.11466(18) 0.14515(18) 0.0121(3) Uani 1 1 d . . . H9 H 0.3973 0.1152 0.0532 0.015 Uiso 1 1 calc R . . C10 C 0.4907(2) 0.27341(18) 0.15996(17) 0.0109(3) Uani 1 1 d . . . C11 C 0.4566(2) 0.39791(18) 0.19654(18) 0.0122(3) Uani 1 1 d . . . H11 H 0.3582 0.4226 0.2620 0.015 Uiso 1 1 calc R . . C12 C 0.5681(2) 0.48557(19) 0.13604(19) 0.0146(3) Uani 1 1 d . . . H12 H 0.5475 0.5698 0.1617 0.018 Uiso 1 1 calc R . . C13 C 0.7109(2) 0.45022(19) 0.03737(18) 0.0139(3) Uani 1 1 d . . . C14 C 0.7466(2) 0.32252(19) 0.00550(18) 0.0146(3) Uani 1 1 d . . . H14 H 0.8461 0.2963 -0.0580 0.017 Uiso 1 1 calc R . . C15 C 0.6354(2) 0.23370(19) 0.06752(18) 0.0128(3) Uani 1 1 d . . . H15 H 0.6585 0.1464 0.0466 0.015 Uiso 1 1 calc R . . C16 C 0.9440(2) 0.5242(2) -0.1372(2) 0.0244(4) Uani 1 1 d . . . H16A H 1.0161 0.4409 -0.1077 0.037 Uiso 1 1 calc R . . H16B H 0.9978 0.6055 -0.1775 0.037 Uiso 1 1 calc R . . H16C H 0.9124 0.5091 -0.2036 0.037 Uiso 1 1 calc R . . Cl1 Cl 0.33781(5) 0.18066(4) 0.79247(4) 0.01232(10) Uani 1 1 d . . . O31 O 0.46169(15) 0.19032(14) 0.83316(13) 0.0156(3) Uani 1 1 d . . . O32 O 0.28159(18) 0.31712(15) 0.72016(15) 0.0229(3) Uani 1 1 d . . . O33 O 0.20918(17) 0.12879(16) 0.90977(14) 0.0233(3) Uani 1 1 d . . . O34 O 0.40139(17) 0.08512(15) 0.70759(14) 0.0188(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.00918(14) 0.00962(14) 0.00744(14) -0.00194(10) -0.00237(11) -0.00329(10) O3 0.0137(6) 0.0140(6) 0.0138(6) -0.0053(5) -0.0043(5) 0.0009(5) O1 0.0125(6) 0.0131(6) 0.0158(6) -0.0070(5) -0.0060(5) -0.0002(5) O4 0.0162(6) 0.0170(7) 0.0224(7) -0.0023(5) -0.0035(6) -0.0093(5) N1 0.0110(6) 0.0100(7) 0.0102(7) -0.0016(5) -0.0038(5) -0.0028(5) N2 0.0106(6) 0.0094(7) 0.0099(7) -0.0018(5) -0.0035(5) -0.0034(5) N5 0.0109(7) 0.0127(7) 0.0095(7) -0.0023(5) -0.0018(5) -0.0050(5) N6 0.0100(6) 0.0099(7) 0.0097(7) -0.0015(5) -0.0028(5) -0.0025(5) C1 0.0143(8) 0.0100(8) 0.0123(8) -0.0032(6) -0.0046(6) -0.0049(6) C2 0.0134(8) 0.0104(8) 0.0138(8) -0.0023(6) -0.0030(7) -0.0036(6) C3 0.0195(9) 0.0129(8) 0.0180(9) -0.0054(7) -0.0085(7) 0.0027(7) C4 0.0119(8) 0.0218(9) 0.0201(9) -0.0109(8) -0.0050(7) 0.0020(7) C5 0.0144(8) 0.0134(8) 0.0173(9) -0.0046(7) -0.0097(7) -0.0010(6) C6 0.0163(8) 0.0115(8) 0.0130(8) -0.0009(6) -0.0086(7) -0.0024(6) C7 0.0119(8) 0.0127(8) 0.0102(8) -0.0042(6) -0.0017(6) -0.0041(6) C8 0.0122(8) 0.0104(8) 0.0105(8) -0.0027(6) -0.0042(6) -0.0011(6) C9 0.0144(8) 0.0123(8) 0.0111(8) -0.0033(6) -0.0058(6) -0.0018(6) C10 0.0114(7) 0.0110(8) 0.0096(7) 0.0002(6) -0.0042(6) -0.0036(6) C11 0.0113(8) 0.0130(8) 0.0121(8) -0.0031(6) -0.0043(6) -0.0017(6) C12 0.0162(8) 0.0123(8) 0.0169(9) -0.0033(7) -0.0069(7) -0.0034(7) C13 0.0138(8) 0.0140(8) 0.0141(8) 0.0023(7) -0.0072(7) -0.0063(7) C14 0.0114(8) 0.0144(8) 0.0150(8) -0.0019(7) -0.0029(7) -0.0024(6) C15 0.0135(8) 0.0114(8) 0.0126(8) -0.0025(6) -0.0036(7) -0.0030(6) C16 0.0187(9) 0.0283(11) 0.0231(10) -0.0020(8) -0.0010(8) -0.0140(8) Cl1 0.01325(19) 0.01130(19) 0.01215(19) -0.00155(15) -0.00511(15) -0.00233(15) O31 0.0159(6) 0.0193(7) 0.0150(6) -0.0055(5) -0.0070(5) -0.0039(5) O32 0.0274(8) 0.0132(7) 0.0274(8) 0.0012(6) -0.0168(6) 0.0009(6) O33 0.0194(7) 0.0292(8) 0.0178(7) -0.0023(6) 0.0000(6) -0.0126(6) O34 0.0217(7) 0.0173(7) 0.0221(7) -0.0103(6) -0.0099(6) -0.0003(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 Cu1 N1 2.0107(14) 2_556 ? Cu1 N1 2.0107(14) . ? Cu1 N2 2.1065(14) 2_556 ? Cu1 N2 2.1065(14) . ? O3 C3 1.429(2) . ? O3 C2 1.437(2) . ? O1 C5 1.436(2) . ? O1 C4 1.439(2) . ? O4 C13 1.366(2) . ? O4 C16 1.434(2) . ? N1 N5 1.328(2) . ? N1 C8 1.355(2) . ? N2 C1 1.496(2) 2_556 ? N2 C7 1.497(2) . ? N2 C6 1.506(2) . ? N5 N6 1.338(2) . ? N6 C9 1.351(2) . ? N6 C10 1.432(2) . ? C1 N2 1.496(2) 2_556 ? C1 C2 1.512(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.509(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.506(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.483(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.360(2) . ? C9 H9 0.9500 . ? C10 C15 1.386(2) . ? C10 C11 1.390(2) . ? C11 C12 1.386(2) . ? C11 H11 0.9500 . ? C12 C13 1.398(3) . ? C12 H12 0.9500 . ? C13 C14 1.393(3) . ? C14 C15 1.393(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? Cl1 O32 1.4374(14) . ? Cl1 O34 1.4430(14) . ? Cl1 O33 1.4466(14) . ? Cl1 O31 1.4503(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 180.00(16) 2_556 . ? N1 Cu1 N2 81.33(6) 2_556 2_556 ? N1 Cu1 N2 98.67(6) . 2_556 ? N1 Cu1 N2 98.67(6) 2_556 . ? N1 Cu1 N2 81.33(6) . . ? N2 Cu1 N2 180.0 2_556 . ? C3 O3 C2 112.73(14) . . ? C5 O1 C4 111.36(13) . . ? C13 O4 C16 116.97(15) . . ? N5 N1 C8 110.28(14) . . ? N5 N1 Cu1 135.09(12) . . ? C8 N1 Cu1 114.19(11) . . ? C1 N2 C7 108.91(13) 2_556 . ? C1 N2 C6 108.81(13) 2_556 . ? C7 N2 C6 106.40(13) . . ? C1 N2 Cu1 115.98(10) 2_556 . ? C7 N2 Cu1 108.21(10) . . ? C6 N2 Cu1 108.12(10) . . ? N1 N5 N6 105.02(13) . . ? N5 N6 C9 112.25(14) . . ? N5 N6 C10 121.45(14) . . ? C9 N6 C10 126.29(15) . . ? N2 C1 C2 114.95(14) 2_556 . ? N2 C1 H1A 108.5 2_556 . ? C2 C1 H1A 108.5 . . ? N2 C1 H1B 108.5 2_556 . ? C2 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? O3 C2 C1 111.59(14) . . ? O3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? O3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? O3 C3 C4 114.19(15) . . ? O3 C3 H3A 108.7 . . ? C4 C3 H3A 108.7 . . ? O3 C3 H3B 108.7 . . ? C4 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? O1 C4 C3 111.42(15) . . ? O1 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? O1 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? O1 C5 C6 106.96(14) . . ? O1 C5 H5A 110.3 . . ? C6 C5 H5A 110.3 . . ? O1 C5 H5B 110.3 . . ? C6 C5 H5B 110.3 . . ? H5A C5 H5B 108.6 . . ? N2 C6 C5 114.34(14) . . ? N2 C6 H6A 108.7 . . ? C5 C6 H6A 108.7 . . ? N2 C6 H6B 108.7 . . ? C5 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C8 C7 N2 108.09(14) . . ? C8 C7 H7A 110.1 . . ? N2 C7 H7A 110.1 . . ? C8 C7 H7B 110.1 . . ? N2 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? N1 C8 C9 107.83(15) . . ? N1 C8 C7 118.19(15) . . ? C9 C8 C7 133.92(16) . . ? N6 C9 C8 104.60(15) . . ? N6 C9 H9 127.7 . . ? C8 C9 H9 127.7 . . ? C15 C10 C11 121.32(16) . . ? C15 C10 N6 117.96(15) . . ? C11 C10 N6 120.67(15) . . ? C12 C11 C10 119.02(16) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 C13 120.12(17) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? O4 C13 C14 124.17(17) . . ? O4 C13 C12 115.51(17) . . ? C14 C13 C12 120.30(16) . . ? C15 C14 C13 119.43(17) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C10 C15 C14 119.64(17) . . ? C10 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? O4 C16 H16A 109.5 . . ? O4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O32 Cl1 O34 109.74(9) . . ? O32 Cl1 O33 109.91(9) . . ? O34 Cl1 O33 109.43(9) . . ? O32 Cl1 O31 109.23(8) . . ? O34 Cl1 O31 109.06(8) . . ? O33 Cl1 O31 109.45(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 N1 N5 180(2) 2_556 . . . ? N2 Cu1 N1 N5 -16.37(17) 2_556 . . . ? N2 Cu1 N1 N5 163.63(17) . . . . ? N1 Cu1 N1 C8 8(2) 2_556 . . . ? N2 Cu1 N1 C8 172.19(12) 2_556 . . . ? N2 Cu1 N1 C8 -7.81(12) . . . . ? N1 Cu1 N2 C1 -34.13(12) 2_556 . . 2_556 ? N1 Cu1 N2 C1 145.87(12) . . . 2_556 ? N2 Cu1 N2 C1 95(11) 2_556 . . 2_556 ? N1 Cu1 N2 C7 -156.81(11) 2_556 . . . ? N1 Cu1 N2 C7 23.19(11) . . . . ? N2 Cu1 N2 C7 -28(12) 2_556 . . . ? N1 Cu1 N2 C6 88.34(11) 2_556 . . . ? N1 Cu1 N2 C6 -91.66(11) . . . . ? N2 Cu1 N2 C6 -143(13) 2_556 . . . ? C8 N1 N5 N6 0.77(18) . . . . ? Cu1 N1 N5 N6 -170.90(12) . . . . ? N1 N5 N6 C9 0.15(19) . . . . ? N1 N5 N6 C10 -178.94(14) . . . . ? C3 O3 C2 C1 -146.58(15) . . . . ? N2 C1 C2 O3 70.80(19) 2_556 . . . ? C2 O3 C3 C4 86.05(19) . . . . ? C5 O1 C4 C3 -161.89(15) . . . . ? O3 C3 C4 O1 -71.0(2) . . . . ? C4 O1 C5 C6 169.89(14) . . . . ? C1 N2 C6 C5 90.23(17) 2_556 . . . ? C7 N2 C6 C5 -152.57(14) . . . . ? Cu1 N2 C6 C5 -36.53(17) . . . . ? O1 C5 C6 N2 69.81(18) . . . . ? C1 N2 C7 C8 -160.07(14) 2_556 . . . ? C6 N2 C7 C8 82.79(16) . . . . ? Cu1 N2 C7 C8 -33.19(15) . . . . ? N5 N1 C8 C9 -1.40(19) . . . . ? Cu1 N1 C8 C9 172.16(11) . . . . ? N5 N1 C8 C7 176.04(14) . . . . ? Cu1 N1 C8 C7 -10.4(2) . . . . ? N2 C7 C8 N1 29.9(2) . . . . ? N2 C7 C8 C9 -153.48(19) . . . . ? N5 N6 C9 C8 -0.98(19) . . . . ? C10 N6 C9 C8 178.06(15) . . . . ? N1 C8 C9 N6 1.40(19) . . . . ? C7 C8 C9 N6 -175.47(18) . . . . ? N5 N6 C10 C15 141.88(17) . . . . ? C9 N6 C10 C15 -37.1(2) . . . . ? N5 N6 C10 C11 -40.7(2) . . . . ? C9 N6 C10 C11 140.37(18) . . . . ? C15 C10 C11 C12 1.9(3) . . . . ? N6 C10 C11 C12 -175.45(16) . . . . ? C10 C11 C12 C13 1.6(3) . . . . ? C16 O4 C13 C14 6.0(3) . . . . ? C16 O4 C13 C12 -172.48(17) . . . . ? C11 C12 C13 O4 174.23(16) . . . . ? C11 C12 C13 C14 -4.3(3) . . . . ? O4 C13 C14 C15 -174.93(17) . . . . ? C12 C13 C14 C15 3.5(3) . . . . ? C11 C10 C15 C14 -2.7(3) . . . . ? N6 C10 C15 C14 174.71(16) . . . . ? C13 C14 C15 C10 0.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.83 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.395 _refine_diff_density_min -0.612 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 851236' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl #Added by publCIF _audit_update_record ; 2013-09-04 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common '[CuL4](ClO4)2, DMF' _chemical_melting_point ? _chemical_formula_moiety 'C30 H38 Cl2 Cu N8 O4, 2(Cl O4), C3 H7 N O' _chemical_formula_sum 'C33 H45 Cl4 Cu N9 O13' _chemical_formula_weight 981.13 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall -p2ybc 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 26.3848(4) _cell_length_b 18.7279(3) _cell_length_c 27.6457(6) _cell_angle_alpha 90.00 _cell_angle_beta 143.2590(10) _cell_angle_gamma 90.00 _cell_volume 8171.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 18278 _cell_measurement_theta_min 3.30 _cell_measurement_theta_max 30.51 _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.595 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4056 _exptl_absorpt_coefficient_mu 0.871 _exptl_absorpt_correction_T_min 0.94200 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4508 _diffrn_reflns_number 251365 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_sigmaI/netI 0.1847 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 30.51 _reflns_number_total 24958 _reflns_number_gt 18278 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^, conventioN3l 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^)+(0.0427P)^2^+12.7901P] 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 18732 _refine_ls_number_parameters 1131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1075 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.003 _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 Cu1 Cu 0.495909(16) 0.013058(14) 0.733645(15) 0.01194(6) Uani 1 1 d . . . Cl1 Cl 0.63109(4) 0.02217(3) 1.17774(3) 0.02368(13) Uani 1 1 d . . . Cl2 Cl 0.33475(4) -0.00973(4) 0.27153(3) 0.02452(13) Uani 1 1 d . . . O1 O 0.32727(10) -0.00042(9) 0.62085(10) 0.0190(3) Uani 1 1 d . . . O2 O 0.42735(10) -0.08573(9) 0.74599(10) 0.0203(3) Uani 1 1 d . . . O3 O 0.67451(10) 0.05220(8) 0.86276(9) 0.0183(3) Uani 1 1 d . . . O4 O 0.60756(11) 0.19159(9) 0.79567(10) 0.0224(4) Uani 1 1 d . . . N3 N 0.51560(11) 0.05378(10) 0.81225(11) 0.0132(4) Uani 1 1 d . . . N4 N 0.43956(12) 0.11554(10) 0.67636(11) 0.0140(4) Uani 1 1 d . . . N1 N 0.47593(11) -0.02540(10) 0.65359(11) 0.0136(4) Uani 1 1 d . . . N2 N 0.56712(12) -0.08545(10) 0.79412(11) 0.0133(4) Uani 1 1 d . . . N5 N 0.54679(11) 0.02708(10) 0.87644(11) 0.0135(4) Uani 1 1 d . . . N6 N 0.53221(11) 0.07658(10) 0.89917(11) 0.0133(4) Uani 1 1 d . . . N7 N 0.44512(12) 0.00243(10) 0.58985(11) 0.0140(4) Uani 1 1 d . . . N8 N 0.44823(11) -0.05040(10) 0.55983(11) 0.0139(4) Uani 1 1 d . . . C1 C 0.34681(14) 0.10748(12) 0.59415(13) 0.0168(4) Uani 1 1 d . . . H1A H 0.3223 0.1555 0.5700 0.020 Uiso 1 1 calc R . . H1B H 0.3409 0.0802 0.5591 0.020 Uiso 1 1 calc R . . C2 C 0.29686(15) 0.07077(13) 0.59461(14) 0.0204(5) Uani 1 1 d . . . H2A H 0.3045 0.0955 0.6318 0.024 Uiso 1 1 calc R . . H2B H 0.2358 0.0710 0.5397 0.024 Uiso 1 1 calc R . . C3 C 0.29225(15) -0.03852(14) 0.63383(14) 0.0214(5) Uani 1 1 d . . . H3A H 0.2316 -0.0488 0.5816 0.026 Uiso 1 1 calc R . . H3B H 0.2972 -0.0100 0.6676 0.026 Uiso 1 1 calc R . . C4 C 0.34115(15) -0.10680(14) 0.67595(14) 0.0217(5) Uani 1 1 d . . . H4A H 0.3230 -0.1336 0.6911 0.026 Uiso 1 1 calc R . . H4B H 0.3327 -0.1373 0.6407 0.026 Uiso 1 1 calc R . . C5 C 0.48370(15) -0.14323(13) 0.79724(14) 0.0185(5) Uani 1 1 d . . . H5A H 0.4639 -0.1864 0.7647 0.022 Uiso 1 1 calc R . . H5B H 0.4867 -0.1543 0.8345 0.022 Uiso 1 1 calc R . . C6 C 0.57014(14) -0.12100(12) 0.84483(13) 0.0161(4) Uani 1 1 d . . . H6A H 0.5962 -0.0879 0.8884 0.019 Uiso 1 1 calc R . . H6B H 0.6068 -0.1638 0.8706 0.019 Uiso 1 1 calc R . . C7 C 0.45049(15) 0.16194(12) 0.72879(13) 0.0163(4) Uani 1 1 d . . . H7A H 0.4911 0.2008 0.7526 0.020 Uiso 1 1 calc R . . H7B H 0.3955 0.1839 0.6953 0.020 Uiso 1 1 calc R . . C8 C 0.48222(13) 0.11920(12) 0.79455(13) 0.0138(4) Uani 1 1 d . . . C9 C 0.49228(14) 0.13440(12) 0.85021(13) 0.0145(4) Uani 1 1 d . . . H9 H 0.4751 0.1763 0.8538 0.017 Uiso 1 1 calc R . . C10 C 0.55764(13) 0.06390(12) 0.96758(13) 0.0137(4) Uani 1 1 d . . . C11 C 0.53664(14) 0.11343(13) 0.98681(13) 0.0171(4) Uani 1 1 d . . . H11 H 0.5073 0.1560 0.9560 0.021 Uiso 1 1 calc R . . C12 C 0.55891(15) 0.10014(13) 1.05144(14) 0.0191(5) Uani 1 1 d . . . H12 H 0.5442 0.1331 1.0649 0.023 Uiso 1 1 calc R . . C13 C 0.60281(14) 0.03847(13) 1.09627(13) 0.0179(5) Uani 1 1 d . . . C14 C 0.62342(15) -0.01129(13) 1.07680(14) 0.0185(5) Uani 1 1 d . . . H14 H 0.6531 -0.0537 1.1079 0.022 Uiso 1 1 calc R . . C15 C 0.60030(14) 0.00148(12) 1.01169(14) 0.0169(4) Uani 1 1 d . . . H15 H 0.6135 -0.0322 0.9973 0.020 Uiso 1 1 calc R . . C16 C 0.65677(14) -0.07286(12) 0.84647(13) 0.0156(4) Uani 1 1 d . . . H16A H 0.6566 -0.0634 0.8111 0.019 Uiso 1 1 calc R . . H16B H 0.6898 -0.1171 0.8772 0.019 Uiso 1 1 calc R . . C17 C 0.70096(14) -0.01205(12) 0.90528(13) 0.0162(4) Uani 1 1 d . . . H17A H 0.6860 -0.0115 0.9287 0.019 Uiso 1 1 calc R . . H17B H 0.7631 -0.0175 0.9499 0.019 Uiso 1 1 calc R . . C18 C 0.71119(15) 0.11438(13) 0.91261(14) 0.0204(5) Uani 1 1 d . . . H18A H 0.7728 0.1072 0.9642 0.025 Uiso 1 1 calc R . . H18B H 0.6854 0.1228 0.9250 0.025 Uiso 1 1 calc R . . C19 C 0.69581(15) 0.17764(13) 0.86870(15) 0.0231(5) Uani 1 1 d . . . H19A H 0.7238 0.2202 0.9041 0.028 Uiso 1 1 calc R . . H19B H 0.7212 0.1686 0.8560 0.028 Uiso 1 1 calc R . . C20 C 0.56945(15) 0.15326(13) 0.72757(14) 0.0187(5) Uani 1 1 d . . . H20A H 0.5898 0.1033 0.7432 0.022 Uiso 1 1 calc R . . H20B H 0.5860 0.1753 0.7091 0.022 Uiso 1 1 calc R . . C21 C 0.47493(14) 0.15447(12) 0.66027(13) 0.0165(4) Uani 1 1 d . . . H21A H 0.4499 0.1335 0.6116 0.020 Uiso 1 1 calc R . . H21B H 0.4563 0.2049 0.6477 0.020 Uiso 1 1 calc R . . C22 C 0.52873(15) -0.13560(12) 0.72933(13) 0.0163(4) Uani 1 1 d . . . H22A H 0.4807 -0.1613 0.7077 0.020 Uiso 1 1 calc R . . H22B H 0.5713 -0.1713 0.7515 0.020 Uiso 1 1 calc R . . C23 C 0.49850(13) -0.09417(12) 0.66376(13) 0.0139(4) Uani 1 1 d . . . C24 C 0.48114(14) -0.11122(12) 0.60363(13) 0.0167(4) Uani 1 1 d . . . H24 H 0.4901 -0.1555 0.5945 0.020 Uiso 1 1 calc R . . C25 C 0.41742(14) -0.03917(13) 0.48805(13) 0.0157(4) Uani 1 1 d . . . C26 C 0.39577(18) -0.09848(14) 0.44395(16) 0.0272(6) Uani 1 1 d . . . H26 H 0.3986 -0.1451 0.4595 0.033 Uiso 1 1 calc R . . C27 C 0.37006(18) -0.08832(15) 0.37697(16) 0.0288(6) Uani 1 1 d . . . H27 H 0.3563 -0.1282 0.3467 0.035 Uiso 1 1 calc R . . C28 C 0.36445(14) -0.02026(14) 0.35434(14) 0.0197(5) Uani 1 1 d . . . C29 C 0.38272(15) 0.03884(14) 0.39645(14) 0.0200(5) Uani 1 1 d . . . H29 H 0.3764 0.0855 0.3787 0.024 Uiso 1 1 calc R . . C30 C 0.41018(14) 0.02945(13) 0.46449(14) 0.0174(4) Uani 1 1 d . . . H30 H 0.4239 0.0695 0.4946 0.021 Uiso 1 1 calc R . . Cu2 Cu 0.019995(17) 0.009563(14) 0.280669(16) 0.01358(7) Uani 1 1 d . . . Cl3 Cl 0.16572(4) -0.00781(4) 0.73034(3) 0.02711(14) Uani 1 1 d . . . Cl4 Cl -0.14043(4) -0.01995(4) -0.17978(4) 0.03157(16) Uani 1 1 d . . . O5 O -0.16254(10) -0.02908(9) 0.14701(10) 0.0195(3) Uani 1 1 d . . . O6 O -0.08224(11) -0.16349(9) 0.21376(10) 0.0235(4) Uani 1 1 d . . . O7 O 0.08590(11) 0.11063(10) 0.26794(11) 0.0284(4) Uani 1 1 d . . . O8 O 0.18822(11) 0.02962(10) 0.39720(11) 0.0237(4) Uani 1 1 d . . . N9 N 0.03563(12) 0.04525(10) 0.35807(11) 0.0149(4) Uani 1 1 d . . . N10 N -0.05480(12) 0.10790(10) 0.21954(11) 0.0144(4) Uani 1 1 d . . . N11 N 0.00020(12) -0.03256(10) 0.20238(11) 0.0145(4) Uani 1 1 d . . . N12 N 0.08345(11) -0.09195(10) 0.34257(11) 0.0143(4) Uani 1 1 d . . . N13 N 0.06382(12) 0.01399(10) 0.41937(11) 0.0158(4) Uani 1 1 d . . . N14 N 0.05516(11) 0.06313(10) 0.44755(11) 0.0136(4) Uani 1 1 d . . . N15 N -0.03832(12) -0.00887(10) 0.13386(11) 0.0163(4) Uani 1 1 d . . . N16 N -0.02577(11) -0.05909(10) 0.10994(11) 0.0145(4) Uani 1 1 d . . . C31 C -0.14470(14) 0.09569(12) 0.16593(13) 0.0166(4) Uani 1 1 d . . . H31A H -0.1769 0.1404 0.1361 0.020 Uiso 1 1 calc R . . H31B H -0.1455 0.0854 0.2004 0.020 Uiso 1 1 calc R . . C32 C -0.18969(14) 0.03620(12) 0.10570(14) 0.0184(5) Uani 1 1 d . . . H32A H -0.2518 0.0415 0.0620 0.022 Uiso 1 1 calc R . . H32B H -0.1760 0.0373 0.0813 0.022 Uiso 1 1 calc R . . C33 C -0.19568(15) -0.08955(13) 0.09622(14) 0.0224(5) Uani 1 1 d . . . H33A H -0.1723 -0.0908 0.0809 0.027 Uiso 1 1 calc R . . H33B H -0.2581 -0.0858 0.0462 0.027 Uiso 1 1 calc R . . C34 C -0.17204(15) -0.15652(13) 0.14072(15) 0.0261(5) Uani 1 1 d . . . H34A H -0.1978 -0.1558 0.1537 0.031 Uiso 1 1 calc R . . H34B H -0.1949 -0.1983 0.1056 0.031 Uiso 1 1 calc R . . C35 C -0.05007(15) -0.13376(13) 0.28205(14) 0.0208(5) Uani 1 1 d . . . H35A H -0.0707 -0.1619 0.2942 0.025 Uiso 1 1 calc R . . H35B H -0.0707 -0.0841 0.2700 0.025 Uiso 1 1 calc R . . C36 C 0.04519(14) -0.13433(12) 0.35404(14) 0.0174(5) Uani 1 1 d . . . H36A H 0.0663 -0.1150 0.4013 0.021 Uiso 1 1 calc R . . H36B H 0.0648 -0.1844 0.3665 0.021 Uiso 1 1 calc R . . C37 C -0.01713(15) 0.15662(12) 0.28524(13) 0.0174(5) Uani 1 1 d . . . H37A H 0.0323 0.1820 0.3092 0.021 Uiso 1 1 calc R . . H37B H -0.0594 0.1925 0.2632 0.021 Uiso 1 1 calc R . . C38 C 0.00962(13) 0.11254(12) 0.34767(13) 0.0143(4) Uani 1 1 d . . . C39 C 0.02132(14) 0.12445(12) 0.40467(13) 0.0152(4) Uani 1 1 d . . . H39 H 0.0085 0.1666 0.4126 0.018 Uiso 1 1 calc R . . C40 C 0.08300(13) 0.04572(13) 0.51678(13) 0.0153(4) Uani 1 1 d . . . C41 C 0.10117(16) 0.10041(14) 0.56280(15) 0.0233(5) Uani 1 1 d . . . H41 H 0.0963 0.1489 0.5494 0.028 Uiso 1 1 calc R . . C42 C 0.12656(17) 0.08305(15) 0.62869(15) 0.0260(5) Uani 1 1 d . . . H42 H 0.1382 0.1197 0.6604 0.031 Uiso 1 1 calc R . . C43 C 0.13489(15) 0.01251(14) 0.64804(14) 0.0208(5) Uani 1 1 d . . . C44 C 0.11841(14) -0.04230(13) 0.60314(14) 0.0191(5) Uani 1 1 d . . . H44 H 0.1257 -0.0907 0.6181 0.023 Uiso 1 1 calc R . . C45 C 0.09118(14) -0.02549(13) 0.53610(14) 0.0169(4) Uani 1 1 d . . . H45 H 0.0783 -0.0623 0.5037 0.020 Uiso 1 1 calc R . . C46 C 0.17408(14) -0.08038(12) 0.42633(13) 0.0174(5) Uani 1 1 d . . . H46A H 0.1754 -0.0546 0.4586 0.021 Uiso 1 1 calc R . . H46B H 0.2013 -0.1274 0.4522 0.021 Uiso 1 1 calc R . . C47 C 0.22432(15) -0.03915(14) 0.42839(15) 0.0229(5) Uani 1 1 d . . . H47A H 0.2842 -0.0356 0.4846 0.028 Uiso 1 1 calc R . . H47B H 0.2225 -0.0634 0.3952 0.028 Uiso 1 1 calc R . . C48 C 0.22240(16) 0.06806(15) 0.38321(16) 0.0273(6) Uani 1 1 d . . . H48A H 0.2184 0.0391 0.3503 0.033 Uiso 1 1 calc R . . H48B H 0.2827 0.0798 0.4352 0.033 Uiso 1 1 calc R . . C49 C 0.17165(16) 0.13435(14) 0.33951(16) 0.0267(6) Uani 1 1 d . . . H49A H 0.1772 0.1644 0.3730 0.032 Uiso 1 1 calc R . . H49B H 0.1904 0.1623 0.3254 0.032 Uiso 1 1 calc R . . C50 C 0.02923(16) 0.16790(13) 0.21809(15) 0.0217(5) Uani 1 1 d . . . H50A H 0.0265 0.1814 0.1814 0.026 Uiso 1 1 calc R . . H50B H 0.0483 0.2099 0.2515 0.026 Uiso 1 1 calc R . . C51 C -0.05678(15) 0.14381(12) 0.16967(14) 0.0178(5) Uani 1 1 d . . . H51A H -0.0947 0.1858 0.1425 0.021 Uiso 1 1 calc R . . H51B H -0.0810 0.1104 0.1271 0.021 Uiso 1 1 calc R . . C52 C 0.08018(15) -0.13588(12) 0.29454(14) 0.0181(5) Uani 1 1 d . . . H52A H 0.1386 -0.1477 0.3288 0.022 Uiso 1 1 calc R . . H52B H 0.0500 -0.1812 0.2780 0.022 Uiso 1 1 calc R . . C53 C 0.03631(14) -0.09686(12) 0.22164(13) 0.0149(4) Uani 1 1 d . . . C54 C 0.01987(14) -0.11451(12) 0.16210(14) 0.0172(4) Uani 1 1 d . . . H54 H 0.0368 -0.1564 0.1582 0.021 Uiso 1 1 calc R . . C55 C -0.05697(14) -0.04949(13) 0.03773(13) 0.0166(4) Uani 1 1 d . . . C56 C -0.04996(16) -0.10606(14) 0.01081(15) 0.0225(5) Uani 1 1 d . . . H56 H -0.0281 -0.1508 0.0379 0.027 Uiso 1 1 calc R . . C57 C -0.07550(16) -0.09610(15) -0.05627(15) 0.0254(5) Uani 1 1 d . . . H57 H -0.0698 -0.1337 -0.0747 0.030 Uiso 1 1 calc R . . C58 C -0.10904(15) -0.03166(15) -0.09583(14) 0.0242(5) Uani 1 1 d . . . C59 C -0.11683(16) 0.02469(15) -0.06953(15) 0.0249(5) Uani 1 1 d . . . H59 H -0.1404 0.0689 -0.0977 0.030 Uiso 1 1 calc R . . C60 C -0.08971(15) 0.01545(14) -0.00146(14) 0.0203(5) Uani 1 1 d . . . H60 H -0.0937 0.0536 0.0180 0.024 Uiso 1 1 calc R . . O10 O -0.10481(13) 0.25292(11) 0.30948(14) 0.0401(5) Uani 1 1 d . . . N101 N -0.23542(14) 0.23019(13) 0.23930(13) 0.0285(5) Uani 1 1 d . . . C101 C -0.28891(19) 0.21808(17) 0.24003(19) 0.0334(6) Uani 1 1 d . . . H10A H -0.3010 0.1669 0.2338 0.050 Uiso 1 1 calc R . . H10B H -0.3422 0.2443 0.1953 0.050 Uiso 1 1 calc R . . H10C H -0.2599 0.2348 0.2915 0.050 Uiso 1 1 calc R . . C102 C -0.2692(2) 0.20991(19) 0.16603(19) 0.0420(8) Uani 1 1 d . . . H10D H -0.2332 0.2299 0.1681 0.063 Uiso 1 1 calc R . . H10E H -0.3270 0.2285 0.1184 0.063 Uiso 1 1 calc R . . H10F H -0.2701 0.1577 0.1626 0.063 Uiso 1 1 calc R . . C103 C -0.15581(19) 0.24879(16) 0.30430(18) 0.0337(6) Uani 1 1 d . . . H103 H -0.1356 0.2600 0.3512 0.040 Uiso 1 1 calc R . . O11 O 0.42165(12) 0.24130(10) 0.35710(12) 0.0312(4) Uani 1 1 d . . . N401 N 0.28079(14) 0.22345(12) 0.26098(13) 0.0261(5) Uani 1 1 d . . . C201 C 0.35635(18) 0.24663(15) 0.33115(17) 0.0293(6) Uani 1 1 d . . . H201 H 0.3610 0.2698 0.3651 0.035 Uiso 1 1 calc R . . C202 C 0.2084(2) 0.22817(19) 0.2374(2) 0.0427(8) Uani 1 1 d . . . H20C H 0.2231 0.2569 0.2771 0.064 Uiso 1 1 calc R . . H20D H 0.1918 0.1801 0.2351 0.064 Uiso 1 1 calc R . . H20E H 0.1611 0.2507 0.1840 0.064 Uiso 1 1 calc R . . C203 C 0.2680(2) 0.1865(2) 0.2056(2) 0.0520(10) Uani 1 1 d . . . H20F H 0.3191 0.1908 0.2249 0.078 Uiso 1 1 calc R . . H20G H 0.2199 0.2079 0.1517 0.078 Uiso 1 1 calc R . . H20H H 0.2563 0.1360 0.2030 0.078 Uiso 1 1 calc R . . Cl10 Cl 0.39379(4) 0.26280(3) 0.49681(3) 0.02201(12) Uani 1 1 d . . . O10A O 0.48448(12) 0.25729(12) 0.56913(12) 0.0367(5) Uani 1 1 d . . . O10B O 0.37153(14) 0.32217(10) 0.44963(12) 0.0347(5) Uani 1 1 d . . . O10C O 0.35947(14) 0.27409(14) 0.51821(13) 0.0449(6) Uani 1 1 d . . . O10D O 0.35978(14) 0.19866(11) 0.45077(14) 0.0420(5) Uani 1 1 d . . . Cl20 Cl 0.18868(3) 0.26102(3) 0.51526(3) 0.01986(12) Uani 1 1 d . . . O20A O 0.27745(11) 0.25516(10) 0.59438(11) 0.0321(4) Uani 1 1 d . . . O20B O 0.13994(14) 0.24140(12) 0.52012(14) 0.0413(5) Uani 1 1 d . . . O20C O 0.16996(12) 0.33376(11) 0.48958(12) 0.0366(5) Uani 1 1 d . . . O20D O 0.16787(13) 0.21515(12) 0.45970(12) 0.0360(5) Uani 1 1 d . . . Cl30 Cl 0.68658(3) 0.25298(3) 0.99811(3) 0.01790(11) Uani 1 1 d . . . O30A O 0.69154(12) 0.31215(10) 1.03520(11) 0.0275(4) Uani 1 1 d . . . O30B O 0.76632(11) 0.24658(10) 1.03396(12) 0.0286(4) Uani 1 1 d . . . O30C O 0.61986(12) 0.26564(10) 0.91268(10) 0.0281(4) Uani 1 1 d . . . O30D O 0.67002(12) 0.18795(10) 1.01142(11) 0.0288(4) Uani 1 1 d . . . Cl40 Cl -0.0809(3) 0.2484(3) 0.0059(3) 0.0274(8) Uani 0.345(6) 1 d P A 1 O4A O -0.0010(7) 0.2915(7) 0.0836(8) 0.052(3) Uani 0.345(6) 1 d P A 1 O4B O -0.1019(4) 0.2168(4) 0.0342(4) 0.050(2) Uani 0.345(6) 1 d P A 1 O4C O -0.1255(19) 0.3111(11) -0.0349(19) 0.082(8) Uani 0.345(6) 1 d P A 1 O4D O -0.1145(5) 0.1922(5) -0.0466(5) 0.0350(19) Uani 0.345(6) 1 d P A 1 Cl50 Cl -0.06580(16) 0.25855(14) 0.00259(16) 0.0296(4) Uani 0.655(6) 1 d P A 2 O5A O -0.0014(5) 0.2613(5) 0.0797(5) 0.108(3) Uani 0.655(6) 1 d P A 2 O5B O -0.0241(3) 0.2634(4) -0.0104(3) 0.103(2) Uani 0.655(6) 1 d P A 2 O5C O -0.1371(9) 0.3058(6) -0.0483(9) 0.060(3) Uani 0.655(6) 1 d P A 2 O5D O -0.0895(5) 0.1935(4) -0.0150(6) 0.184(6) Uani 0.655(6) 1 d P A 2 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 Cu1 0.01554(13) 0.01067(13) 0.01096(12) 0.00164(9) 0.01092(12) 0.00256(10) Cl1 0.0259(3) 0.0327(3) 0.0158(3) -0.0032(2) 0.0174(3) -0.0070(2) Cl2 0.0238(3) 0.0389(4) 0.0167(3) 0.0017(2) 0.0176(3) 0.0005(2) O1 0.0197(8) 0.0203(8) 0.0216(8) 0.0035(7) 0.0176(8) 0.0024(7) O2 0.0158(8) 0.0164(8) 0.0187(8) 0.0001(6) 0.0116(7) -0.0012(6) O3 0.0213(8) 0.0129(8) 0.0151(8) 0.0021(6) 0.0133(7) 0.0012(6) O4 0.0216(9) 0.0154(8) 0.0160(8) 0.0005(6) 0.0119(8) 0.0031(7) N3 0.0161(9) 0.0109(9) 0.0128(9) 0.0011(7) 0.0116(8) 0.0013(7) N4 0.0189(9) 0.0111(9) 0.0139(9) 0.0008(7) 0.0136(8) 0.0017(7) N1 0.0148(9) 0.0136(9) 0.0122(8) 0.0008(7) 0.0108(8) 0.0005(7) N2 0.0166(9) 0.0105(9) 0.0124(9) 0.0006(7) 0.0115(8) 0.0005(7) N5 0.0164(9) 0.0132(9) 0.0138(9) 0.0017(7) 0.0127(8) 0.0022(7) N6 0.0152(9) 0.0128(9) 0.0129(9) -0.0017(7) 0.0115(8) -0.0008(7) N7 0.0163(9) 0.0154(9) 0.0122(9) -0.0010(7) 0.0119(8) 0.0004(7) N8 0.0149(9) 0.0145(9) 0.0137(9) -0.0034(7) 0.0117(8) -0.0029(7) C1 0.0169(10) 0.0159(11) 0.0141(10) 0.0018(8) 0.0116(10) 0.0037(8) C2 0.0163(11) 0.0216(12) 0.0188(11) 0.0028(9) 0.0130(10) 0.0053(9) C3 0.0162(11) 0.0304(14) 0.0183(11) 0.0022(10) 0.0140(10) -0.0003(10) C4 0.0198(11) 0.0255(13) 0.0202(12) -0.0016(10) 0.0161(11) -0.0058(10) C5 0.0218(11) 0.0163(11) 0.0191(11) 0.0040(9) 0.0168(11) 0.0021(9) C6 0.0224(11) 0.0127(10) 0.0164(11) 0.0031(8) 0.0163(10) 0.0027(9) C7 0.0226(11) 0.0125(10) 0.0139(10) 0.0011(8) 0.0147(10) 0.0036(9) C8 0.0138(10) 0.0115(10) 0.0139(10) -0.0004(8) 0.0106(9) -0.0002(8) C9 0.0182(10) 0.0120(10) 0.0162(10) 0.0002(8) 0.0144(10) 0.0007(8) C10 0.0127(10) 0.0159(11) 0.0112(10) -0.0025(8) 0.0093(9) -0.0037(8) C11 0.0198(11) 0.0170(11) 0.0152(10) 0.0008(9) 0.0141(10) 0.0013(9) C12 0.0206(11) 0.0225(12) 0.0178(11) -0.0035(9) 0.0162(10) -0.0018(9) C13 0.0172(11) 0.0253(12) 0.0115(10) -0.0031(9) 0.0116(10) -0.0073(9) C14 0.0188(11) 0.0180(11) 0.0149(11) 0.0009(9) 0.0127(10) -0.0002(9) C15 0.0187(11) 0.0164(11) 0.0164(11) -0.0011(9) 0.0143(10) -0.0008(9) C16 0.0158(10) 0.0147(11) 0.0154(10) 0.0030(8) 0.0123(10) 0.0030(8) C17 0.0146(10) 0.0147(11) 0.0132(10) 0.0044(8) 0.0098(9) 0.0019(8) C18 0.0204(11) 0.0165(11) 0.0170(11) -0.0032(9) 0.0134(10) -0.0022(9) C19 0.0194(12) 0.0176(12) 0.0198(12) -0.0005(9) 0.0129(11) -0.0023(9) C20 0.0232(12) 0.0151(11) 0.0189(11) 0.0009(9) 0.0171(11) -0.0004(9) C21 0.0231(11) 0.0113(10) 0.0165(11) 0.0017(8) 0.0162(10) 0.0010(9) C22 0.0234(11) 0.0111(10) 0.0166(11) -0.0023(8) 0.0165(10) -0.0019(9) C23 0.0144(10) 0.0117(10) 0.0138(10) -0.0018(8) 0.0109(9) -0.0018(8) C24 0.0206(11) 0.0135(11) 0.0174(11) -0.0017(8) 0.0156(10) -0.0027(9) C25 0.0151(10) 0.0210(12) 0.0127(10) -0.0009(9) 0.0115(9) -0.0024(9) C26 0.0429(16) 0.0211(13) 0.0272(13) -0.0076(10) 0.0303(14) -0.0105(11) C27 0.0427(16) 0.0255(13) 0.0254(13) -0.0108(11) 0.0289(13) -0.0124(12) C28 0.0160(11) 0.0324(14) 0.0126(10) -0.0014(9) 0.0119(10) -0.0022(9) C29 0.0198(11) 0.0228(12) 0.0183(11) 0.0053(9) 0.0154(10) 0.0043(9) C30 0.0186(11) 0.0182(11) 0.0164(11) 0.0014(9) 0.0143(10) 0.0033(9) Cu2 0.01668(13) 0.01308(14) 0.01210(13) 0.00310(10) 0.01178(12) 0.00390(10) Cl3 0.0243(3) 0.0437(4) 0.0158(3) 0.0011(2) 0.0166(3) -0.0036(3) Cl4 0.0228(3) 0.0580(5) 0.0154(3) -0.0039(3) 0.0156(3) -0.0093(3) O5 0.0227(8) 0.0138(8) 0.0172(8) 0.0004(6) 0.0149(8) -0.0001(6) O6 0.0197(8) 0.0180(8) 0.0170(8) -0.0018(7) 0.0112(8) 0.0008(7) O7 0.0170(8) 0.0220(9) 0.0272(10) 0.0034(7) 0.0134(8) -0.0012(7) O8 0.0229(9) 0.0246(9) 0.0259(9) 0.0037(7) 0.0201(8) -0.0011(7) N9 0.0150(9) 0.0149(9) 0.0126(9) 0.0026(7) 0.0105(8) 0.0024(7) N10 0.0169(9) 0.0123(9) 0.0129(9) 0.0011(7) 0.0117(8) 0.0000(7) N11 0.0164(9) 0.0127(9) 0.0145(9) 0.0016(7) 0.0123(8) 0.0013(7) N12 0.0155(9) 0.0121(9) 0.0122(9) 0.0005(7) 0.0104(8) 0.0013(7) N13 0.0202(9) 0.0158(9) 0.0139(9) 0.0015(7) 0.0141(8) 0.0033(7) N14 0.0132(8) 0.0148(9) 0.0123(9) -0.0006(7) 0.0101(8) -0.0003(7) N15 0.0184(9) 0.0160(9) 0.0158(9) 0.0005(7) 0.0140(9) 0.0006(7) N16 0.0146(9) 0.0149(9) 0.0135(9) -0.0026(7) 0.0112(8) -0.0034(7) C31 0.0166(10) 0.0169(11) 0.0159(11) 0.0033(9) 0.0129(10) 0.0030(8) C32 0.0154(10) 0.0180(11) 0.0145(11) 0.0022(9) 0.0103(10) 0.0005(9) C33 0.0186(11) 0.0191(12) 0.0182(11) -0.0042(9) 0.0122(11) -0.0025(9) C34 0.0190(12) 0.0178(12) 0.0218(12) -0.0034(10) 0.0120(11) -0.0045(9) C35 0.0224(12) 0.0175(12) 0.0214(12) -0.0003(9) 0.0173(11) -0.0012(9) C36 0.0206(11) 0.0146(11) 0.0167(11) 0.0019(8) 0.0149(10) 0.0011(9) C37 0.0235(11) 0.0134(11) 0.0166(11) -0.0010(8) 0.0163(10) -0.0013(9) C38 0.0142(10) 0.0121(10) 0.0129(10) -0.0025(8) 0.0100(9) -0.0032(8) C39 0.0158(10) 0.0122(10) 0.0142(10) -0.0011(8) 0.0113(9) -0.0013(8) C40 0.0125(10) 0.0212(12) 0.0116(10) 0.0004(8) 0.0095(9) -0.0004(8) C41 0.0296(13) 0.0197(12) 0.0215(12) -0.0042(10) 0.0206(12) -0.0052(10) C42 0.0322(14) 0.0276(14) 0.0196(12) -0.0068(10) 0.0210(12) -0.0056(11) C43 0.0176(11) 0.0331(14) 0.0117(10) 0.0011(9) 0.0117(10) -0.0024(10) C44 0.0153(10) 0.0239(12) 0.0180(11) 0.0042(9) 0.0133(10) 0.0017(9) C45 0.0155(10) 0.0181(11) 0.0173(11) 0.0007(9) 0.0132(10) 0.0015(8) C46 0.0159(10) 0.0160(11) 0.0129(10) 0.0001(8) 0.0099(10) 0.0031(9) C47 0.0190(11) 0.0234(13) 0.0242(12) -0.0022(10) 0.0168(11) -0.0001(10) C48 0.0231(12) 0.0330(15) 0.0276(13) 0.0009(11) 0.0207(12) -0.0035(11) C49 0.0214(12) 0.0260(14) 0.0266(13) -0.0015(11) 0.0179(12) -0.0054(10) C50 0.0261(12) 0.0168(11) 0.0239(12) 0.0025(9) 0.0205(12) -0.0010(9) C51 0.0229(11) 0.0149(11) 0.0172(11) 0.0037(9) 0.0164(10) 0.0028(9) C52 0.0235(12) 0.0145(11) 0.0175(11) 0.0001(9) 0.0167(11) 0.0022(9) C53 0.0141(10) 0.0132(10) 0.0150(10) -0.0004(8) 0.0111(9) -0.0014(8) C54 0.0193(11) 0.0151(11) 0.0192(11) -0.0014(9) 0.0159(10) -0.0003(9) C55 0.0152(10) 0.0217(12) 0.0139(10) -0.0027(9) 0.0119(10) -0.0058(9) C56 0.0246(12) 0.0246(13) 0.0201(12) -0.0039(10) 0.0183(11) -0.0047(10) C57 0.0237(12) 0.0348(15) 0.0205(12) -0.0094(11) 0.0183(11) -0.0088(11) C58 0.0157(11) 0.0427(16) 0.0133(11) -0.0038(10) 0.0114(10) -0.0080(10) C59 0.0209(12) 0.0315(14) 0.0186(12) 0.0031(10) 0.0149(11) -0.0012(10) C60 0.0196(11) 0.0243(13) 0.0167(11) -0.0008(9) 0.0144(10) -0.0018(9) O10 0.0340(11) 0.0293(11) 0.0594(14) -0.0028(10) 0.0379(12) -0.0050(9) N101 0.0254(11) 0.0364(13) 0.0266(12) 0.0016(10) 0.0216(11) -0.0030(10) C101 0.0360(15) 0.0376(16) 0.0418(16) -0.0076(13) 0.0346(15) -0.0087(13) C102 0.0452(18) 0.053(2) 0.0363(17) -0.0102(15) 0.0346(16) -0.0142(15) C103 0.0343(15) 0.0320(15) 0.0361(16) -0.0022(12) 0.0285(14) -0.0046(12) O11 0.0314(10) 0.0214(9) 0.0449(12) -0.0007(8) 0.0315(10) -0.0030(8) N401 0.0307(12) 0.0292(12) 0.0298(12) -0.0019(9) 0.0268(11) -0.0023(9) C201 0.0361(15) 0.0278(14) 0.0343(15) -0.0051(11) 0.0305(14) -0.0072(11) C202 0.0371(17) 0.051(2) 0.053(2) -0.0146(16) 0.0392(17) -0.0098(15) C203 0.051(2) 0.072(3) 0.051(2) -0.0276(19) 0.045(2) -0.0204(18) Cl10 0.0222(3) 0.0215(3) 0.0173(3) 0.0035(2) 0.0147(2) 0.0005(2) O10A 0.0208(9) 0.0526(14) 0.0250(10) 0.0042(9) 0.0157(9) 0.0009(9) O10B 0.0517(13) 0.0202(10) 0.0341(11) 0.0070(8) 0.0348(11) 0.0019(9) O10C 0.0374(12) 0.0762(17) 0.0321(11) 0.0254(11) 0.0304(11) 0.0244(11) O10D 0.0419(12) 0.0199(10) 0.0464(13) -0.0077(9) 0.0314(12) -0.0097(9) Cl20 0.0161(2) 0.0171(3) 0.0196(3) -0.0028(2) 0.0128(2) -0.0027(2) O20A 0.0190(9) 0.0247(10) 0.0228(9) 0.0005(8) 0.0101(8) 0.0058(7) O20B 0.0463(13) 0.0451(13) 0.0497(13) -0.0202(10) 0.0423(12) -0.0250(10) O20C 0.0294(10) 0.0251(10) 0.0328(11) 0.0100(8) 0.0199(10) 0.0090(8) O20D 0.0323(11) 0.0438(12) 0.0334(11) -0.0182(9) 0.0266(10) -0.0114(9) Cl30 0.0161(2) 0.0151(3) 0.0175(3) 0.0010(2) 0.0124(2) 0.0003(2) O30A 0.0288(10) 0.0243(10) 0.0306(10) -0.0061(8) 0.0240(9) -0.0020(8) O30B 0.0228(9) 0.0225(9) 0.0380(11) 0.0012(8) 0.0238(9) 0.0013(7) O30C 0.0281(10) 0.0283(10) 0.0166(9) 0.0062(7) 0.0154(8) 0.0075(8) O30D 0.0269(9) 0.0231(10) 0.0268(10) 0.0020(7) 0.0194(9) -0.0060(7) Cl40 0.0308(17) 0.0234(16) 0.0205(10) -0.0026(10) 0.0188(12) -0.0009(12) O4A 0.031(4) 0.081(8) 0.038(5) -0.043(6) 0.026(4) -0.029(5) O4B 0.048(4) 0.049(5) 0.031(4) 0.014(3) 0.027(4) -0.002(3) O4C 0.067(13) 0.012(5) 0.085(14) 0.004(6) 0.043(11) 0.016(6) O4D 0.027(4) 0.025(4) 0.022(3) -0.017(3) 0.013(3) -0.014(3) Cl50 0.0347(9) 0.0226(8) 0.0292(7) -0.0065(5) 0.0251(6) -0.0059(6) O5A 0.067(4) 0.106(7) 0.034(3) -0.023(4) 0.014(3) 0.007(4) O5B 0.086(4) 0.183(7) 0.082(4) -0.051(4) 0.077(4) -0.054(4) O5C 0.043(3) 0.046(5) 0.057(4) 0.028(4) 0.033(4) 0.010(3) O5D 0.075(6) 0.031(3) 0.172(10) -0.034(5) 0.037(6) 0.004(3) _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 Cu1 N3 1.9401(18) . ? Cu1 N1 1.9559(18) . ? Cu1 N4 2.1514(18) . ? Cu1 N2 2.1666(18) . ? Cl1 C13 1.741(2) . ? Cl2 C28 1.738(2) . ? O1 C2 1.419(3) . ? O1 C3 1.422(3) . ? O2 C5 1.415(3) . ? O2 C4 1.421(3) . ? O3 C17 1.415(3) . ? O3 C18 1.433(3) . ? O4 C19 1.425(3) . ? O4 C20 1.427(3) . ? N3 N5 1.318(2) . ? N3 C8 1.351(3) . ? N4 C1 1.504(3) . ? N4 C21 1.505(3) . ? N4 C7 1.506(3) . ? N1 N7 1.320(3) . ? N1 C23 1.351(3) . ? N2 C22 1.486(3) . ? N2 C6 1.495(3) . ? N2 C16 1.503(3) . ? N5 N6 1.338(3) . ? N6 C9 1.353(3) . ? N6 C10 1.432(3) . ? N7 N8 1.335(3) . ? N8 C24 1.354(3) . ? N8 C25 1.434(3) . ? C1 C2 1.496(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.499(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.516(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.486(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.365(3) . ? C9 H9 0.9500 . ? C10 C15 1.386(3) . ? C10 C11 1.387(3) . ? C11 C12 1.384(3) . ? C11 H11 0.9500 . ? C12 C13 1.382(3) . ? C12 H12 0.9500 . ? C13 C14 1.387(3) . ? C14 C15 1.382(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.504(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.501(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.498(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.486(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.362(3) . ? C24 H24 0.9500 . ? C25 C30 1.383(3) . ? C25 C26 1.389(3) . ? C26 C27 1.383(3) . ? C26 H26 0.9500 . ? C27 C28 1.375(4) . ? C27 H27 0.9500 . ? C28 C29 1.383(3) . ? C29 C30 1.382(3) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? Cu2 N11 1.9411(19) . ? Cu2 N9 1.9446(19) . ? Cu2 N12 2.1804(18) . ? Cu2 N10 2.1902(19) . ? Cl3 C43 1.737(2) . ? Cl4 C58 1.743(2) . ? O5 C32 1.415(3) . ? O5 C33 1.432(3) . ? O6 C35 1.424(3) . ? O6 C34 1.429(3) . ? O7 C50 1.408(3) . ? O7 C49 1.434(3) . ? O8 C47 1.412(3) . ? O8 C48 1.428(3) . ? N9 N13 1.322(3) . ? N9 C38 1.351(3) . ? N10 C37 1.492(3) . ? N10 C51 1.497(3) . ? N10 C31 1.497(3) . ? N11 N15 1.316(3) . ? N11 C53 1.352(3) . ? N12 C46 1.501(3) . ? N12 C36 1.504(3) . ? N12 C52 1.505(3) . ? N13 N14 1.338(3) . ? N14 C39 1.351(3) . ? N14 C40 1.434(3) . ? N15 N16 1.335(3) . ? N16 C54 1.351(3) . ? N16 C55 1.436(3) . ? C31 C32 1.502(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.499(3) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.504(3) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C38 1.485(3) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 C39 1.360(3) . ? C39 H39 0.9500 . ? C40 C41 1.386(3) . ? C40 C45 1.388(3) . ? C41 C42 1.384(3) . ? C41 H41 0.9500 . ? C42 C43 1.375(4) . ? C42 H42 0.9500 . ? C43 C44 1.385(3) . ? C44 C45 1.384(3) . ? C44 H44 0.9500 . ? C45 H45 0.9500 . ? C46 C47 1.495(3) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C48 C49 1.484(4) . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C50 C51 1.509(3) . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 C53 1.482(3) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 C54 1.365(3) . ? C54 H54 0.9500 . ? C55 C60 1.378(3) . ? C55 C56 1.390(3) . ? C56 C57 1.387(3) . ? C56 H56 0.9500 . ? C57 C58 1.373(4) . ? C57 H57 0.9500 . ? C58 C59 1.387(4) . ? C59 C60 1.387(3) . ? C59 H59 0.9500 . ? C60 H60 0.9500 . ? O10 C103 1.236(3) . ? N101 C103 1.309(4) . ? N101 C101 1.445(3) . ? N101 C102 1.465(4) . ? C101 H10A 0.9800 . ? C101 H10B 0.9800 . ? C101 H10C 0.9800 . ? C102 H10D 0.9800 . ? C102 H10E 0.9800 . ? C102 H10F 0.9800 . ? C103 H103 0.9500 . ? O11 C201 1.230(3) . ? N401 C201 1.315(4) . ? N401 C202 1.444(3) . ? N401 C203 1.450(4) . ? C201 H201 0.9500 . ? C202 H20C 0.9800 . ? C202 H20D 0.9800 . ? C202 H20E 0.9800 . ? C203 H20F 0.9800 . ? C203 H20G 0.9800 . ? C203 H20H 0.9800 . ? Cl10 O10D 1.428(2) . ? Cl10 O10B 1.4334(19) . ? Cl10 O10A 1.437(2) . ? Cl10 O10C 1.440(2) . ? Cl20 O20C 1.429(2) . ? Cl20 O20D 1.4308(19) . ? Cl20 O20A 1.4393(18) . ? Cl20 O20B 1.444(2) . ? Cl30 O30D 1.4378(18) . ? Cl30 O30C 1.4387(17) . ? Cl30 O30B 1.4425(18) . ? Cl30 O30A 1.4428(18) . ? Cl40 O4C 1.38(2) . ? Cl40 O4D 1.393(9) . ? Cl40 O4B 1.403(8) . ? Cl40 O4A 1.565(11) . ? Cl50 O5D 1.275(8) . ? Cl50 O5A 1.277(9) . ? Cl50 O5B 1.409(5) . ? Cl50 O5C 1.436(13) . ? 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 N3 Cu1 N1 178.46(8) . . ? N3 Cu1 N4 83.15(7) . . ? N1 Cu1 N4 95.44(7) . . ? N3 Cu1 N2 100.49(7) . . ? N1 Cu1 N2 80.81(7) . . ? N4 Cu1 N2 171.13(7) . . ? C2 O1 C3 112.63(18) . . ? C5 O2 C4 113.77(18) . . ? C17 O3 C18 112.87(17) . . ? C19 O4 C20 113.61(18) . . ? N5 N3 C8 110.73(18) . . ? N5 N3 Cu1 132.62(15) . . ? C8 N3 Cu1 116.05(14) . . ? C1 N4 C21 104.20(16) . . ? C1 N4 C7 109.69(17) . . ? C21 N4 C7 108.60(17) . . ? C1 N4 Cu1 110.52(13) . . ? C21 N4 Cu1 115.05(13) . . ? C7 N4 Cu1 108.64(13) . . ? N7 N1 C23 110.59(18) . . ? N7 N1 Cu1 133.20(15) . . ? C23 N1 Cu1 116.20(14) . . ? C22 N2 C6 108.74(17) . . ? C22 N2 C16 106.64(17) . . ? C6 N2 C16 107.87(17) . . ? C22 N2 Cu1 106.02(13) . . ? C6 N2 Cu1 117.67(13) . . ? C16 N2 Cu1 109.38(13) . . ? N3 N5 N6 105.39(17) . . ? N5 N6 C9 111.80(17) . . ? N5 N6 C10 119.92(18) . . ? C9 N6 C10 128.27(19) . . ? N1 N7 N8 104.96(17) . . ? N7 N8 C24 112.49(18) . . ? N7 N8 C25 120.13(18) . . ? C24 N8 C25 127.38(19) . . ? C2 C1 N4 114.27(18) . . ? C2 C1 H1A 108.7 . . ? N4 C1 H1A 108.7 . . ? C2 C1 H1B 108.7 . . ? N4 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? O1 C2 C1 107.17(18) . . ? O1 C2 H2A 110.3 . . ? C1 C2 H2A 110.3 . . ? O1 C2 H2B 110.3 . . ? C1 C2 H2B 110.3 . . ? H2A C2 H2B 108.5 . . ? O1 C3 C4 107.17(19) . . ? O1 C3 H3A 110.3 . . ? C4 C3 H3A 110.3 . . ? O1 C3 H3B 110.3 . . ? C4 C3 H3B 110.3 . . ? H3A C3 H3B 108.5 . . ? O2 C4 C3 105.2(2) . . ? O2 C4 H4A 110.7 . . ? C3 C4 H4A 110.7 . . ? O2 C4 H4B 110.7 . . ? C3 C4 H4B 110.7 . . ? H4A C4 H4B 108.8 . . ? O2 C5 C6 107.63(18) . . ? O2 C5 H5A 110.2 . . ? C6 C5 H5A 110.2 . . ? O2 C5 H5B 110.2 . . ? C6 C5 H5B 110.2 . . ? H5A C5 H5B 108.5 . . ? N2 C6 C5 113.33(18) . . ? N2 C6 H6A 108.9 . . ? C5 C6 H6A 108.9 . . ? N2 C6 H6B 108.9 . . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? C8 C7 N4 110.64(18) . . ? C8 C7 H7A 109.5 . . ? N4 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? N4 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? N3 C8 C9 107.43(19) . . ? N3 C8 C7 119.74(19) . . ? C9 C8 C7 132.6(2) . . ? N6 C9 C8 104.64(19) . . ? N6 C9 H9 127.7 . . ? C8 C9 H9 127.7 . . ? C15 C10 C11 121.3(2) . . ? C15 C10 N6 119.5(2) . . ? C11 C10 N6 119.2(2) . . ? C12 C11 C10 119.2(2) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C13 C12 C11 119.4(2) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 121.4(2) . . ? C12 C13 Cl1 119.29(18) . . ? C14 C13 Cl1 119.31(19) . . ? C15 C14 C13 119.2(2) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C14 C15 C10 119.4(2) . . ? C14 C15 H15 120.3 . . ? C10 C15 H15 120.3 . . ? N2 C16 C17 114.71(18) . . ? N2 C16 H16A 108.6 . . ? C17 C16 H16A 108.6 . . ? N2 C16 H16B 108.6 . . ? C17 C16 H16B 108.6 . . ? H16A C16 H16B 107.6 . . ? O3 C17 C16 107.87(18) . . ? O3 C17 H17A 110.1 . . ? C16 C17 H17A 110.1 . . ? O3 C17 H17B 110.1 . . ? C16 C17 H17B 110.1 . . ? H17A C17 H17B 108.4 . . ? O3 C18 C19 109.09(19) . . ? O3 C18 H18A 109.9 . . ? C19 C18 H18A 109.9 . . ? O3 C18 H18B 109.9 . . ? C19 C18 H18B 109.9 . . ? H18A C18 H18B 108.3 . . ? O4 C19 C18 111.5(2) . . ? O4 C19 H19A 109.3 . . ? C18 C19 H19A 109.3 . . ? O4 C19 H19B 109.3 . . ? C18 C19 H19B 109.3 . . ? H19A C19 H19B 108.0 . . ? O4 C20 C21 110.02(19) . . ? O4 C20 H20A 109.7 . . ? C21 C20 H20A 109.7 . . ? O4 C20 H20B 109.7 . . ? C21 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? C20 C21 N4 115.78(18) . . ? C20 C21 H21A 108.3 . . ? N4 C21 H21A 108.3 . . ? C20 C21 H21B 108.3 . . ? N4 C21 H21B 108.3 . . ? H21A C21 H21B 107.4 . . ? N2 C22 C23 108.76(18) . . ? N2 C22 H22A 109.9 . . ? C23 C22 H22A 109.9 . . ? N2 C22 H22B 109.9 . . ? C23 C22 H22B 109.9 . . ? H22A C22 H22B 108.3 . . ? N1 C23 C24 108.0(2) . . ? N1 C23 C22 117.90(19) . . ? C24 C23 C22 133.9(2) . . ? N8 C24 C23 104.0(2) . . ? N8 C24 H24 128.0 . . ? C23 C24 H24 128.0 . . ? C30 C25 C26 121.7(2) . . ? C30 C25 N8 119.9(2) . . ? C26 C25 N8 118.4(2) . . ? C27 C26 C25 118.7(2) . . ? C27 C26 H26 120.6 . . ? C25 C26 H26 120.6 . . ? C28 C27 C26 119.7(2) . . ? C28 C27 H27 120.2 . . ? C26 C27 H27 120.2 . . ? C27 C28 C29 121.4(2) . . ? C27 C28 Cl2 118.37(19) . . ? C29 C28 Cl2 120.21(19) . . ? C30 C29 C28 119.5(2) . . ? C30 C29 H29 120.2 . . ? C28 C29 H29 120.2 . . ? C29 C30 C25 118.9(2) . . ? C29 C30 H30 120.6 . . ? C25 C30 H30 120.6 . . ? N11 Cu2 N9 175.54(8) . . ? N11 Cu2 N12 82.65(7) . . ? N9 Cu2 N12 94.80(7) . . ? N11 Cu2 N10 102.14(7) . . ? N9 Cu2 N10 79.95(7) . . ? N12 Cu2 N10 171.55(7) . . ? C32 O5 C33 112.06(17) . . ? C35 O6 C34 112.92(19) . . ? C50 O7 C49 112.22(19) . . ? C47 O8 C48 111.22(19) . . ? N13 N9 C38 110.73(18) . . ? N13 N9 Cu2 131.58(15) . . ? C38 N9 Cu2 117.57(15) . . ? C37 N10 C51 110.13(17) . . ? C37 N10 C31 106.24(17) . . ? C51 N10 C31 107.38(17) . . ? C37 N10 Cu2 105.40(13) . . ? C51 N10 Cu2 115.69(14) . . ? C31 N10 Cu2 111.63(13) . . ? N15 N11 C53 110.78(18) . . ? N15 N11 Cu2 132.47(15) . . ? C53 N11 Cu2 116.60(15) . . ? C46 N12 C36 105.05(16) . . ? C46 N12 C52 109.52(17) . . ? C36 N12 C52 108.90(17) . . ? C46 N12 Cu2 110.91(13) . . ? C36 N12 Cu2 113.74(13) . . ? C52 N12 Cu2 108.61(13) . . ? N9 N13 N14 104.98(17) . . ? N13 N14 C39 112.02(18) . . ? N13 N14 C40 118.48(18) . . ? C39 N14 C40 129.49(19) . . ? N11 N15 N16 105.27(18) . . ? N15 N16 C54 112.04(18) . . ? N15 N16 C55 120.47(19) . . ? C54 N16 C55 127.5(2) . . ? N10 C31 C32 115.37(18) . . ? N10 C31 H31A 108.4 . . ? C32 C31 H31A 108.4 . . ? N10 C31 H31B 108.4 . . ? C32 C31 H31B 108.4 . . ? H31A C31 H31B 107.5 . . ? O5 C32 C31 107.89(18) . . ? O5 C32 H32A 110.1 . . ? C31 C32 H32A 110.1 . . ? O5 C32 H32B 110.1 . . ? C31 C32 H32B 110.1 . . ? H32A C32 H32B 108.4 . . ? O5 C33 C34 109.4(2) . . ? O5 C33 H33A 109.8 . . ? C34 C33 H33A 109.8 . . ? O5 C33 H33B 109.8 . . ? C34 C33 H33B 109.8 . . ? H33A C33 H33B 108.3 . . ? O6 C34 C33 111.4(2) . . ? O6 C34 H34A 109.4 . . ? C33 C34 H34A 109.4 . . ? O6 C34 H34B 109.4 . . ? C33 C34 H34B 109.4 . . ? H34A C34 H34B 108.0 . . ? O6 C35 C36 109.89(19) . . ? O6 C35 H35A 109.7 . . ? C36 C35 H35A 109.7 . . ? O6 C35 H35B 109.7 . . ? C36 C35 H35B 109.7 . . ? H35A C35 H35B 108.2 . . ? N12 C36 C35 114.18(18) . . ? N12 C36 H36A 108.7 . . ? C35 C36 H36A 108.7 . . ? N12 C36 H36B 108.7 . . ? C35 C36 H36B 108.7 . . ? H36A C36 H36B 107.6 . . ? C38 C37 N10 107.91(18) . . ? C38 C37 H37A 110.1 . . ? N10 C37 H37A 110.1 . . ? C38 C37 H37B 110.1 . . ? N10 C37 H37B 110.1 . . ? H37A C37 H37B 108.4 . . ? N9 C38 C39 107.55(19) . . ? N9 C38 C37 116.94(19) . . ? C39 C38 C37 135.3(2) . . ? N14 C39 C38 104.71(19) . . ? N14 C39 H39 127.6 . . ? C38 C39 H39 127.6 . . ? C41 C40 C45 121.6(2) . . ? C41 C40 N14 119.2(2) . . ? C45 C40 N14 119.2(2) . . ? C42 C41 C40 118.8(2) . . ? C42 C41 H41 120.6 . . ? C40 C41 H41 120.6 . . ? C43 C42 C41 119.7(2) . . ? C43 C42 H42 120.2 . . ? C41 C42 H42 120.2 . . ? C42 C43 C44 121.7(2) . . ? C42 C43 Cl3 118.76(19) . . ? C44 C43 Cl3 119.52(19) . . ? C45 C44 C43 119.0(2) . . ? C45 C44 H44 120.5 . . ? C43 C44 H44 120.5 . . ? C44 C45 C40 119.2(2) . . ? C44 C45 H45 120.4 . . ? C40 C45 H45 120.4 . . ? C47 C46 N12 113.66(19) . . ? C47 C46 H46A 108.8 . . ? N12 C46 H46A 108.8 . . ? C47 C46 H46B 108.8 . . ? N12 C46 H46B 108.8 . . ? H46A C46 H46B 107.7 . . ? O8 C47 C46 107.71(19) . . ? O8 C47 H47A 110.2 . . ? C46 C47 H47A 110.2 . . ? O8 C47 H47B 110.2 . . ? C46 C47 H47B 110.2 . . ? H47A C47 H47B 108.5 . . ? O8 C48 C49 106.8(2) . . ? O8 C48 H48A 110.4 . . ? C49 C48 H48A 110.4 . . ? O8 C48 H48B 110.4 . . ? C49 C48 H48B 110.4 . . ? H48A C48 H48B 108.6 . . ? O7 C49 C48 105.1(2) . . ? O7 C49 H49A 110.7 . . ? C48 C49 H49A 110.7 . . ? O7 C49 H49B 110.7 . . ? C48 C49 H49B 110.7 . . ? H49A C49 H49B 108.8 . . ? O7 C50 C51 107.64(19) . . ? O7 C50 H50A 110.2 . . ? C51 C50 H50A 110.2 . . ? O7 C50 H50B 110.2 . . ? C51 C50 H50B 110.2 . . ? H50A C50 H50B 108.5 . . ? N10 C51 C50 113.55(19) . . ? N10 C51 H51A 108.9 . . ? C50 C51 H51A 108.9 . . ? N10 C51 H51B 108.9 . . ? C50 C51 H51B 108.9 . . ? H51A C51 H51B 107.7 . . ? C53 C52 N12 111.13(18) . . ? C53 C52 H52A 109.4 . . ? N12 C52 H52A 109.4 . . ? C53 C52 H52B 109.4 . . ? N12 C52 H52B 109.4 . . ? H52A C52 H52B 108.0 . . ? N11 C53 C54 107.3(2) . . ? N11 C53 C52 120.7(2) . . ? C54 C53 C52 131.9(2) . . ? N16 C54 C53 104.6(2) . . ? N16 C54 H54 127.7 . . ? C53 C54 H54 127.7 . . ? C60 C55 C56 121.4(2) . . ? C60 C55 N16 120.2(2) . . ? C56 C55 N16 118.4(2) . . ? C57 C56 C55 118.9(2) . . ? C57 C56 H56 120.6 . . ? C55 C56 H56 120.6 . . ? C58 C57 C56 119.7(2) . . ? C58 C57 H57 120.2 . . ? C56 C57 H57 120.2 . . ? C57 C58 C59 121.5(2) . . ? C57 C58 Cl4 119.1(2) . . ? C59 C58 Cl4 119.4(2) . . ? C60 C59 C58 119.0(2) . . ? C60 C59 H59 120.5 . . ? C58 C59 H59 120.5 . . ? C55 C60 C59 119.6(2) . . ? C55 C60 H60 120.2 . . ? C59 C60 H60 120.2 . . ? C103 N101 C101 122.2(2) . . ? C103 N101 C102 119.7(2) . . ? C101 N101 C102 117.3(2) . . ? N101 C101 H10A 109.5 . . ? N101 C101 H10B 109.5 . . ? H10A C101 H10B 109.5 . . ? N101 C101 H10C 109.5 . . ? H10A C101 H10C 109.5 . . ? H10B C101 H10C 109.5 . . ? N101 C102 H10D 109.5 . . ? N101 C102 H10E 109.5 . . ? H10D C102 H10E 109.5 . . ? N101 C102 H10F 109.5 . . ? H10D C102 H10F 109.5 . . ? H10E C102 H10F 109.5 . . ? O10 C103 N101 125.2(3) . . ? O10 C103 H103 117.4 . . ? N101 C103 H103 117.4 . . ? C201 N401 C202 122.6(2) . . ? C201 N401 C203 120.7(2) . . ? C202 N401 C203 116.6(2) . . ? O11 C201 N401 126.4(3) . . ? O11 C201 H201 116.8 . . ? N401 C201 H201 116.8 . . ? N401 C202 H20C 109.5 . . ? N401 C202 H20D 109.5 . . ? H20C C202 H20D 109.5 . . ? N401 C202 H20E 109.5 . . ? H20C C202 H20E 109.5 . . ? H20D C202 H20E 109.5 . . ? N401 C203 H20F 109.5 . . ? N401 C203 H20G 109.5 . . ? H20F C203 H20G 109.5 . . ? N401 C203 H20H 109.5 . . ? H20F C203 H20H 109.5 . . ? H20G C203 H20H 109.5 . . ? O10D Cl10 O10B 109.57(13) . . ? O10D Cl10 O10A 109.63(13) . . ? O10B Cl10 O10A 109.44(13) . . ? O10D Cl10 O10C 109.70(15) . . ? O10B Cl10 O10C 109.03(13) . . ? O10A Cl10 O10C 109.45(12) . . ? O20C Cl20 O20D 110.89(13) . . ? O20C Cl20 O20A 108.75(12) . . ? O20D Cl20 O20A 110.05(12) . . ? O20C Cl20 O20B 108.05(14) . . ? O20D Cl20 O20B 110.06(12) . . ? O20A Cl20 O20B 108.98(13) . . ? O30D Cl30 O30C 109.68(11) . . ? O30D Cl30 O30B 109.20(11) . . ? O30C Cl30 O30B 109.51(12) . . ? O30D Cl30 O30A 109.98(11) . . ? O30C Cl30 O30A 109.57(11) . . ? O30B Cl30 O30A 108.89(11) . . ? O4C Cl40 O4D 112.1(14) . . ? O4C Cl40 O4B 110.8(13) . . ? O4D Cl40 O4B 93.2(6) . . ? O4C Cl40 O4A 90.7(15) . . ? O4D Cl40 O4A 148.5(6) . . ? O4B Cl40 O4A 98.7(6) . . ? O5D Cl50 O5A 105.4(7) . . ? O5D Cl50 O5B 102.1(7) . . ? O5A Cl50 O5B 99.1(5) . . ? O5D Cl50 O5C 111.0(7) . . ? O5A Cl50 O5C 123.9(7) . . ? O5B Cl50 O5C 112.9(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 N1 Cu1 N3 N5 -161(3) . . . . ? N4 Cu1 N3 N5 175.2(2) . . . . ? N2 Cu1 N3 N5 -13.0(2) . . . . ? N1 Cu1 N3 C8 29(3) . . . . ? N4 Cu1 N3 C8 5.08(16) . . . . ? N2 Cu1 N3 C8 176.90(15) . . . . ? N3 Cu1 N4 C1 -117.18(14) . . . . ? N1 Cu1 N4 C1 63.45(14) . . . . ? N2 Cu1 N4 C1 128.0(4) . . . . ? N3 Cu1 N4 C21 125.17(15) . . . . ? N1 Cu1 N4 C21 -54.21(15) . . . . ? N2 Cu1 N4 C21 10.4(5) . . . . ? N3 Cu1 N4 C7 3.21(14) . . . . ? N1 Cu1 N4 C7 -176.16(14) . . . . ? N2 Cu1 N4 C7 -111.6(4) . . . . ? N3 Cu1 N1 N7 -19(3) . . . . ? N4 Cu1 N1 N7 4.8(2) . . . . ? N2 Cu1 N1 N7 -167.0(2) . . . . ? N3 Cu1 N1 C23 160(3) . . . . ? N4 Cu1 N1 C23 -176.36(16) . . . . ? N2 Cu1 N1 C23 11.75(15) . . . . ? N3 Cu1 N2 C22 155.54(13) . . . . ? N1 Cu1 N2 C22 -25.29(13) . . . . ? N4 Cu1 N2 C22 -90.9(5) . . . . ? N3 Cu1 N2 C6 33.66(16) . . . . ? N1 Cu1 N2 C6 -147.17(16) . . . . ? N4 Cu1 N2 C6 147.2(4) . . . . ? N3 Cu1 N2 C16 -89.83(14) . . . . ? N1 Cu1 N2 C16 89.34(14) . . . . ? N4 Cu1 N2 C16 23.7(5) . . . . ? C8 N3 N5 N6 0.4(2) . . . . ? Cu1 N3 N5 N6 -170.16(15) . . . . ? N3 N5 N6 C9 -0.1(2) . . . . ? N3 N5 N6 C10 179.20(18) . . . . ? C23 N1 N7 N8 0.4(2) . . . . ? Cu1 N1 N7 N8 179.29(15) . . . . ? N1 N7 N8 C24 -0.6(2) . . . . ? N1 N7 N8 C25 178.62(18) . . . . ? C21 N4 C1 C2 -179.01(18) . . . . ? C7 N4 C1 C2 -62.9(2) . . . . ? Cu1 N4 C1 C2 56.9(2) . . . . ? C3 O1 C2 C1 172.46(18) . . . . ? N4 C1 C2 O1 -65.0(2) . . . . ? C2 O1 C3 C4 -169.35(19) . . . . ? C5 O2 C4 C3 175.93(18) . . . . ? O1 C3 C4 O2 55.1(2) . . . . ? C4 O2 C5 C6 154.77(19) . . . . ? C22 N2 C6 C5 -59.2(2) . . . . ? C16 N2 C6 C5 -174.48(18) . . . . ? Cu1 N2 C6 C5 61.3(2) . . . . ? O2 C5 C6 N2 -44.7(2) . . . . ? C1 N4 C7 C8 111.0(2) . . . . ? C21 N4 C7 C8 -135.75(19) . . . . ? Cu1 N4 C7 C8 -9.9(2) . . . . ? N5 N3 C8 C9 -0.5(2) . . . . ? Cu1 N3 C8 C9 171.76(14) . . . . ? N5 N3 C8 C7 174.48(19) . . . . ? Cu1 N3 C8 C7 -13.3(3) . . . . ? N4 C7 C8 N3 15.5(3) . . . . ? N4 C7 C8 C9 -171.0(2) . . . . ? N5 N6 C9 C8 -0.2(2) . . . . ? C10 N6 C9 C8 -179.4(2) . . . . ? N3 C8 C9 N6 0.4(2) . . . . ? C7 C8 C9 N6 -173.7(2) . . . . ? N5 N6 C10 C15 2.6(3) . . . . ? C9 N6 C10 C15 -178.2(2) . . . . ? N5 N6 C10 C11 -175.38(19) . . . . ? C9 N6 C10 C11 3.8(3) . . . . ? C15 C10 C11 C12 0.1(3) . . . . ? N6 C10 C11 C12 178.0(2) . . . . ? C10 C11 C12 C13 1.1(3) . . . . ? C11 C12 C13 C14 -1.5(4) . . . . ? C11 C12 C13 Cl1 179.73(18) . . . . ? C12 C13 C14 C15 0.7(3) . . . . ? Cl1 C13 C14 C15 179.47(18) . . . . ? C13 C14 C15 C10 0.5(3) . . . . ? C11 C10 C15 C14 -0.9(3) . . . . ? N6 C10 C15 C14 -178.8(2) . . . . ? C22 N2 C16 C17 167.90(18) . . . . ? C6 N2 C16 C17 -75.4(2) . . . . ? Cu1 N2 C16 C17 53.7(2) . . . . ? C18 O3 C17 C16 178.54(18) . . . . ? N2 C16 C17 O3 -80.5(2) . . . . ? C17 O3 C18 C19 167.43(19) . . . . ? C20 O4 C19 C18 -88.1(2) . . . . ? O3 C18 C19 O4 62.2(3) . . . . ? C19 O4 C20 C21 164.27(19) . . . . ? O4 C20 C21 N4 -65.8(2) . . . . ? C1 N4 C21 C20 -164.60(19) . . . . ? C7 N4 C21 C20 78.5(2) . . . . ? Cu1 N4 C21 C20 -43.4(2) . . . . ? C6 N2 C22 C23 160.72(18) . . . . ? C16 N2 C22 C23 -83.2(2) . . . . ? Cu1 N2 C22 C23 33.3(2) . . . . ? N7 N1 C23 C24 -0.2(2) . . . . ? Cu1 N1 C23 C24 -179.23(15) . . . . ? N7 N1 C23 C22 -175.63(19) . . . . ? Cu1 N1 C23 C22 5.3(3) . . . . ? N2 C22 C23 N1 -27.6(3) . . . . ? N2 C22 C23 C24 158.4(2) . . . . ? N7 N8 C24 C23 0.5(2) . . . . ? C25 N8 C24 C23 -178.7(2) . . . . ? N1 C23 C24 N8 -0.2(2) . . . . ? C22 C23 C24 N8 174.3(2) . . . . ? N7 N8 C25 C30 20.8(3) . . . . ? C24 N8 C25 C30 -160.1(2) . . . . ? N7 N8 C25 C26 -159.4(2) . . . . ? C24 N8 C25 C26 19.7(3) . . . . ? C30 C25 C26 C27 3.0(4) . . . . ? N8 C25 C26 C27 -176.8(2) . . . . ? C25 C26 C27 C28 -1.6(4) . . . . ? C26 C27 C28 C29 -1.0(4) . . . . ? C26 C27 C28 Cl2 178.2(2) . . . . ? C27 C28 C29 C30 2.4(4) . . . . ? Cl2 C28 C29 C30 -176.90(18) . . . . ? C28 C29 C30 C25 -1.0(3) . . . . ? C26 C25 C30 C29 -1.7(4) . . . . ? N8 C25 C30 C29 178.1(2) . . . . ? N11 Cu2 N9 N13 46.4(11) . . . . ? N12 Cu2 N9 N13 -8.5(2) . . . . ? N10 Cu2 N9 N13 164.8(2) . . . . ? N11 Cu2 N9 C38 -129.1(10) . . . . ? N12 Cu2 N9 C38 175.96(16) . . . . ? N10 Cu2 N9 C38 -10.71(16) . . . . ? N11 Cu2 N10 C37 -157.64(13) . . . . ? N9 Cu2 N10 C37 26.37(13) . . . . ? N12 Cu2 N10 C37 78.4(5) . . . . ? N11 Cu2 N10 C51 -35.73(16) . . . . ? N9 Cu2 N10 C51 148.28(16) . . . . ? N12 Cu2 N10 C51 -159.7(4) . . . . ? N11 Cu2 N10 C31 87.45(14) . . . . ? N9 Cu2 N10 C31 -88.54(14) . . . . ? N12 Cu2 N10 C31 -36.5(5) . . . . ? N9 Cu2 N11 N15 125.0(10) . . . . ? N12 Cu2 N11 N15 -179.7(2) . . . . ? N10 Cu2 N11 N15 7.4(2) . . . . ? N9 Cu2 N11 C53 -60.0(11) . . . . ? N12 Cu2 N11 C53 -4.65(16) . . . . ? N10 Cu2 N11 C53 -177.59(15) . . . . ? N11 Cu2 N12 C46 122.44(15) . . . . ? N9 Cu2 N12 C46 -61.24(14) . . . . ? N10 Cu2 N12 C46 -112.4(5) . . . . ? N11 Cu2 N12 C36 -119.40(15) . . . . ? N9 Cu2 N12 C36 56.92(15) . . . . ? N10 Cu2 N12 C36 5.7(5) . . . . ? N11 Cu2 N12 C52 2.03(14) . . . . ? N9 Cu2 N12 C52 178.35(14) . . . . ? N10 Cu2 N12 C52 127.2(4) . . . . ? C38 N9 N13 N14 -0.1(2) . . . . ? Cu2 N9 N13 N14 -175.87(15) . . . . ? N9 N13 N14 C39 0.6(2) . . . . ? N9 N13 N14 C40 -178.23(18) . . . . ? C53 N11 N15 N16 -0.3(2) . . . . ? Cu2 N11 N15 N16 174.94(15) . . . . ? N11 N15 N16 C54 0.3(2) . . . . ? N11 N15 N16 C55 -177.70(18) . . . . ? C37 N10 C31 C32 -167.58(18) . . . . ? C51 N10 C31 C32 74.6(2) . . . . ? Cu2 N10 C31 C32 -53.2(2) . . . . ? C33 O5 C32 C31 -174.23(19) . . . . ? N10 C31 C32 O5 78.3(2) . . . . ? C32 O5 C33 C34 -174.2(2) . . . . ? C35 O6 C34 C33 92.2(3) . . . . ? O5 C33 C34 O6 -59.0(3) . . . . ? C34 O6 C35 C36 -172.60(19) . . . . ? C46 N12 C36 C35 162.75(19) . . . . ? C52 N12 C36 C35 -80.0(2) . . . . ? Cu2 N12 C36 C35 41.3(2) . . . . ? O6 C35 C36 N12 60.3(3) . . . . ? C51 N10 C37 C38 -161.57(18) . . . . ? C31 N10 C37 C38 82.4(2) . . . . ? Cu2 N10 C37 C38 -36.14(19) . . . . ? N13 N9 C38 C39 -0.4(2) . . . . ? Cu2 N9 C38 C39 176.03(14) . . . . ? N13 N9 C38 C37 175.04(19) . . . . ? Cu2 N9 C38 C37 -8.5(3) . . . . ? N10 C37 C38 N9 31.8(3) . . . . ? N10 C37 C38 C39 -154.4(2) . . . . ? N13 N14 C39 C38 -0.8(2) . . . . ? C40 N14 C39 C38 177.8(2) . . . . ? N9 C38 C39 N14 0.7(2) . . . . ? C37 C38 C39 N14 -173.5(2) . . . . ? N13 N14 C40 C41 158.8(2) . . . . ? C39 N14 C40 C41 -19.8(3) . . . . ? N13 N14 C40 C45 -21.1(3) . . . . ? C39 N14 C40 C45 160.3(2) . . . . ? C45 C40 C41 C42 -1.2(4) . . . . ? N14 C40 C41 C42 178.9(2) . . . . ? C40 C41 C42 C43 1.3(4) . . . . ? C41 C42 C43 C44 -0.1(4) . . . . ? C41 C42 C43 Cl3 -179.3(2) . . . . ? C42 C43 C44 C45 -1.4(4) . . . . ? Cl3 C43 C44 C45 177.88(17) . . . . ? C43 C44 C45 C40 1.5(3) . . . . ? C41 C40 C45 C44 -0.2(3) . . . . ? N14 C40 C45 C44 179.72(19) . . . . ? C36 N12 C46 C47 179.53(19) . . . . ? C52 N12 C46 C47 62.7(2) . . . . ? Cu2 N12 C46 C47 -57.2(2) . . . . ? C48 O8 C47 C46 -169.3(2) . . . . ? N12 C46 C47 O8 63.2(2) . . . . ? C47 O8 C48 C49 171.7(2) . . . . ? C50 O7 C49 C48 -178.4(2) . . . . ? O8 C48 C49 O7 -57.4(3) . . . . ? C49 O7 C50 C51 -153.6(2) . . . . ? C37 N10 C51 C50 57.6(2) . . . . ? C31 N10 C51 C50 172.86(19) . . . . ? Cu2 N10 C51 C50 -61.8(2) . . . . ? O7 C50 C51 N10 47.4(3) . . . . ? C46 N12 C52 C53 -120.7(2) . . . . ? C36 N12 C52 C53 124.9(2) . . . . ? Cu2 N12 C52 C53 0.6(2) . . . . ? N15 N11 C53 C54 0.2(3) . . . . ? Cu2 N11 C53 C54 -175.85(15) . . . . ? N15 N11 C53 C52 -177.2(2) . . . . ? Cu2 N11 C53 C52 6.7(3) . . . . ? N12 C52 C53 N11 -4.6(3) . . . . ? N12 C52 C53 C54 178.7(2) . . . . ? N15 N16 C54 C53 -0.1(2) . . . . ? C55 N16 C54 C53 177.7(2) . . . . ? N11 C53 C54 N16 -0.1(2) . . . . ? C52 C53 C54 N16 177.0(2) . . . . ? N15 N16 C55 C60 9.0(3) . . . . ? C54 N16 C55 C60 -168.6(2) . . . . ? N15 N16 C55 C56 -173.6(2) . . . . ? C54 N16 C55 C56 8.8(3) . . . . ? C60 C55 C56 C57 0.9(4) . . . . ? N16 C55 C56 C57 -176.4(2) . . . . ? C55 C56 C57 C58 -1.7(4) . . . . ? C56 C57 C58 C59 1.1(4) . . . . ? C56 C57 C58 Cl4 179.75(19) . . . . ? C57 C58 C59 C60 0.2(4) . . . . ? Cl4 C58 C59 C60 -178.39(18) . . . . ? C56 C55 C60 C59 0.4(4) . . . . ? N16 C55 C60 C59 177.7(2) . . . . ? C58 C59 C60 C55 -1.0(4) . . . . ? C101 N101 C103 O10 172.3(3) . . . . ? C102 N101 C103 O10 2.1(5) . . . . ? C202 N401 C201 O11 176.1(3) . . . . ? C203 N401 C201 O11 0.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.123 _refine_diff_density_min -0.813 _refine_diff_density_rms 0.078 _database_code_depnum_ccdc_archive 'CCDC 851237' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_update_record ; 2013-09-02 # Formatted by publCIF ; # publcif _publ_body_element loop end _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common '[CuL7(MCN)](ClO4)2' _chemical_melting_point ? _chemical_formula_moiety 'C25 H31 Cu N9, 2(Cl O4)' _chemical_formula_sum 'C25 H31 Cl2 Cu N9 O8' _chemical_formula_weight 720.03 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.8278(5) _cell_length_b 14.1824(5) _cell_length_c 16.0830(7) _cell_angle_alpha 89.792(4) _cell_angle_beta 78.263(4) _cell_angle_gamma 87.476(2) _cell_volume 3085.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 27245 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.50 _exptl_crystal_description prismatic _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1484 _exptl_absorpt_coefficient_mu 0.944 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 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-Nonius KappaAPEXII' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27245 _diffrn_reflns_av_R_equivalents 0.0552 _diffrn_reflns_av_sigmaI/netI 0.0652 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_point_group_measured_fraction_full 0.998 _reflns_number_total 14144 _reflns_number_gt 11118 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect Bruker-Nonius' _computing_cell_refinement HKL2000 _computing_data_reduction HKL2000 _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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 ; w=1/[\s^2^(Fo^2^)+(0.0349P)^2^+19.2453P] 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 14140 _refine_ls_number_parameters 845 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1138 _refine_ls_R_factor_gt 0.0864 _refine_ls_wR_factor_ref 0.2355 _refine_ls_wR_factor_gt 0.2113 _refine_ls_goodness_of_fit_ref 1.212 _refine_ls_restrained_S_all 1.212 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.40989(5) -0.75384(5) -0.29058(4) 0.01891(17) Uani 1 1 d . . . . . N4 N 0.3993(4) -0.8588(4) -0.2068(3) 0.0219(10) Uani 1 1 d . . . . . N3 N 0.4004(4) -0.8632(4) -0.3717(3) 0.0231(10) Uani 1 1 d . . . . . N2 N 0.3977(4) -0.6465(4) -0.3754(3) 0.0213(10) Uani 1 1 d . . . . . N1 N 0.4008(4) -0.6460(3) -0.2113(3) 0.0211(10) Uani 1 1 d . . . . . N5 N 0.5820(4) -0.7572(4) -0.3090(3) 0.0290(12) Uani 1 1 d . . . . . N6 N 0.3850(4) -0.6368(3) -0.1276(3) 0.0227(10) Uani 1 1 d . . . . . N7 N 0.3936(4) -0.5444(3) -0.1138(3) 0.0221(10) Uani 1 1 d . . . . . N8 N 0.3792(3) -0.8646(3) -0.1234(3) 0.0198(10) Uani 1 1 d . . . . . N9 N 0.3877(4) -0.9571(3) -0.1071(3) 0.0211(10) Uani 1 1 d . . . . . C1 C 0.4512(5) -0.6681(5) -0.4647(4) 0.0265(13) Uani 1 1 d . . . . . H1A H 0.5231 -0.6731 -0.4659 0.032 Uiso 1 1 calc R U . . . H1B H 0.4388 -0.6147 -0.5015 0.032 Uiso 1 1 calc R U . . . C2 C 0.2913(4) -0.6231(5) -0.3716(4) 0.0268(13) Uani 1 1 d . . . . . H2A H 0.2844 -0.5712 -0.4107 0.040 Uiso 1 1 calc R U . . . H2B H 0.2596 -0.6040 -0.3137 0.040 Uiso 1 1 calc R U . . . H2C H 0.2596 -0.6786 -0.3880 0.040 Uiso 1 1 calc R U . . . C3 C 0.4433(5) -0.5633(4) -0.3451(4) 0.0259(13) Uani 1 1 d . . . . . H3A H 0.4170 -0.5045 -0.3674 0.031 Uiso 1 1 calc R U . . . H3B H 0.5158 -0.5677 -0.3659 0.031 Uiso 1 1 calc R U . . . C4 C 0.4198(4) -0.5612(4) -0.2501(4) 0.0216(11) Uani 1 1 d . . . . . C5 C 0.4146(4) -0.4959(4) -0.1878(4) 0.0219(11) Uani 1 1 d . . . . . H5 H 0.4237 -0.4301 -0.1945 0.026 Uiso 1 1 calc R U . . . C6 C 0.3788(4) -0.5099(4) -0.0288(4) 0.0216(11) Uani 1 1 d . . . . . C7 C 0.3705(6) -0.4138(5) -0.0138(4) 0.0370(16) Uani 1 1 d . . . . . H7 H 0.3761 -0.3710 -0.0599 0.044 Uiso 1 1 calc R U . . . C8 C 0.3540(7) -0.3800(5) 0.0687(5) 0.046(2) Uani 1 1 d . . . . . H8 H 0.3495 -0.3139 0.0790 0.055 Uiso 1 1 calc R U . . . C9 C 0.3441(5) -0.4413(5) 0.1353(4) 0.0362(16) Uani 1 1 d . . . . . H9 H 0.3329 -0.4177 0.1918 0.043 Uiso 1 1 calc R U . . . C10 C 0.3505(6) -0.5375(5) 0.1204(4) 0.0368(16) Uani 1 1 d . . . . . H10 H 0.3429 -0.5800 0.1669 0.044 Uiso 1 1 calc R U . . . C11 C 0.3680(6) -0.5722(5) 0.0379(4) 0.0345(15) Uani 1 1 d . . . . . H11 H 0.3725 -0.6383 0.0275 0.041 Uiso 1 1 calc R U . . . C12 C 0.4212(5) -0.7584(5) -0.5013(4) 0.0276(13) Uani 1 1 d . . . . . H12A H 0.3482 -0.7569 -0.4934 0.033 Uiso 1 1 calc R U . . . H12B H 0.4489 -0.7603 -0.5631 0.033 Uiso 1 1 calc R U . . . C13 C 0.4551(5) -0.8478(5) -0.4615(4) 0.0268(13) Uani 1 1 d . . . . . H13A H 0.4461 -0.9025 -0.4968 0.032 Uiso 1 1 calc R U . . . H13B H 0.5266 -0.8450 -0.4618 0.032 Uiso 1 1 calc R U . . . C14 C 0.2951(5) -0.8827(5) -0.3686(4) 0.0295(14) Uani 1 1 d . . . . . H14A H 0.2616 -0.8917 -0.3094 0.044 Uiso 1 1 calc R U . . . H14B H 0.2912 -0.9400 -0.4014 0.044 Uiso 1 1 calc R U . . . H14C H 0.2630 -0.8293 -0.3928 0.044 Uiso 1 1 calc R U . . . C15 C 0.4478(5) -0.9479(4) -0.3382(4) 0.0269(13) Uani 1 1 d . . . . . H15A H 0.5206 -0.9471 -0.3563 0.032 Uiso 1 1 calc R U . . . H15B H 0.4254 -1.0063 -0.3605 0.032 Uiso 1 1 calc R U . . . C16 C 0.4190(4) -0.9456(4) -0.2434(4) 0.0228(12) Uani 1 1 d . . . . . C17 C 0.4121(4) -1.0098(4) -0.1796(4) 0.0244(12) Uani 1 1 d . . . . . H17 H 0.4220 -1.0764 -0.1846 0.029 Uiso 1 1 calc R U . . . C18 C 0.3734(4) -0.9876(4) -0.0205(4) 0.0244(12) Uani 1 1 d . . . . . C19 C 0.3293(4) -0.9257(4) 0.0439(4) 0.0250(12) Uani 1 1 d . . . . . H19 H 0.3059 -0.8644 0.0310 0.030 Uiso 1 1 calc R U . . . C20 C 0.3199(5) -0.9547(5) 0.1277(4) 0.0311(14) Uani 1 1 d . . . . . H20 H 0.2907 -0.9128 0.1727 0.037 Uiso 1 1 calc R U . . . C21 C 0.3531(5) -1.0447(5) 0.1457(4) 0.0340(16) Uani 1 1 d . . . . . H21 H 0.3466 -1.0641 0.2031 0.041 Uiso 1 1 calc R U . . . C22 C 0.3954(5) -1.1063(5) 0.0810(5) 0.0328(15) Uani 1 1 d . . . . . H22 H 0.4175 -1.1680 0.0941 0.039 Uiso 1 1 calc R U . . . C23 C 0.4060(5) -1.0786(4) -0.0032(4) 0.0284(13) Uani 1 1 d . . . . . H23 H 0.4349 -1.1208 -0.0480 0.034 Uiso 1 1 calc R U . . . C24 C 0.6585(5) -0.7596(4) -0.2961(4) 0.0237(12) Uani 1 1 d . . . . . C25 C 0.7572(5) -0.7616(5) -0.2788(4) 0.0327(14) Uani 1 1 d . . . . . H25A H 0.7533 -0.7604 -0.2173 0.049 Uiso 1 1 calc R U . . . H25B H 0.7916 -0.7064 -0.3046 0.049 Uiso 1 1 calc R U . . . H25C H 0.7937 -0.8193 -0.3030 0.049 Uiso 1 1 calc R U . . . Cu1' Cu 0.01145(5) -0.75087(5) 0.30155(4) 0.01913(17) Uani 1 1 d . . . . . N4' N 0.0464(4) -0.6471(3) 0.2203(3) 0.0204(10) Uani 1 1 d . . . . . N3' N -0.0353(4) -0.6396(3) 0.3834(3) 0.0210(10) Uani 1 1 d . . . . . N2' N -0.0466(4) -0.8551(4) 0.3828(3) 0.0217(10) Uani 1 1 d . . . . . N1' N 0.0382(4) -0.8570(3) 0.2201(3) 0.0230(10) Uani 1 1 d . . . . . N5' N 0.1716(4) -0.7601(4) 0.3226(4) 0.0308(12) Uani 1 1 d . . . . . N6' N 0.0658(4) -0.8648(3) 0.1368(3) 0.0216(10) Uani 1 1 d . . . . . N7' N 0.0784(4) -0.9572(3) 0.1209(3) 0.0225(10) Uani 1 1 d . . . . . N8' N 0.0692(4) -0.6412(3) 0.1365(3) 0.0220(10) Uani 1 1 d . . . . . N9' N 0.0888(3) -0.5501(3) 0.1210(3) 0.0195(9) Uani 1 1 d . . . . . C1' C -0.0369(5) -0.8402(5) 0.4732(4) 0.0274(13) Uani 1 1 d . . . . . H1'1 H 0.0340 -0.8461 0.4758 0.033 Uiso 1 1 calc R U . . . H1'2 H -0.0707 -0.8911 0.5085 0.033 Uiso 1 1 calc R U . . . C2' C -0.1528(5) -0.8644(5) 0.3775(4) 0.0298(14) Uani 1 1 d . . . . . H2'1 H -0.1788 -0.9197 0.4099 0.045 Uiso 1 1 calc R U . . . H2'2 H -0.1577 -0.8720 0.3180 0.045 Uiso 1 1 calc R U . . . H2'3 H -0.1913 -0.8076 0.4012 0.045 Uiso 1 1 calc R U . . . C3' C 0.0080(5) -0.9450(4) 0.3519(4) 0.0254(12) Uani 1 1 d . . . . . H3'1 H -0.0333 -0.9991 0.3717 0.030 Uiso 1 1 calc R U . . . H3'2 H 0.0693 -0.9519 0.3745 0.030 Uiso 1 1 calc R U . . . C4' C 0.0329(4) -0.9438(4) 0.2567(4) 0.0214(11) Uani 1 1 d . . . . . C5' C 0.0580(4) -1.0087(4) 0.1939(4) 0.0244(12) Uani 1 1 d . . . . . H5' H 0.0607 -1.0754 0.1992 0.029 Uiso 1 1 calc R U . . . C6' C 0.1108(4) -0.9900(4) 0.0349(4) 0.0209(11) Uani 1 1 d . . . . . C7' C 0.1384(5) -1.0841(5) 0.0189(4) 0.0281(13) Uani 1 1 d . . . . . H7' H 0.1345 -1.1281 0.0641 0.034 Uiso 1 1 calc R U . . . C8' C 0.1719(5) -1.1127(5) -0.0648(4) 0.0342(15) Uani 1 1 d . . . . . H8' H 0.1926 -1.1768 -0.0770 0.041 Uiso 1 1 calc R U . . . C9' C 0.1757(5) -1.0490(5) -0.1311(4) 0.0335(15) Uani 1 1 d . . . . . H9' H 0.1983 -1.0697 -0.1881 0.040 Uiso 1 1 calc R U . . . C10' C 0.1463(5) -0.9547(5) -0.1139(4) 0.0299(14) Uani 1 1 d . . . . . H10' H 0.1486 -0.9112 -0.1593 0.036 Uiso 1 1 calc R U . . . C11' C 0.1139(5) -0.9245(5) -0.0310(4) 0.0269(13) Uani 1 1 d . . . . . H11' H 0.0940 -0.8602 -0.0187 0.032 Uiso 1 1 calc R U . . . C12' C -0.0791(5) -0.7458(5) 0.5114(4) 0.0299(14) Uani 1 1 d . . . . . H12C H -0.1488 -0.7385 0.5053 0.036 Uiso 1 1 calc R U . . . H12D H -0.0789 -0.7469 0.5729 0.036 Uiso 1 1 calc R U . . . C13' C -0.0253(5) -0.6600(5) 0.4731(4) 0.0260(13) Uani 1 1 d . . . . . H13C H -0.0512 -0.6042 0.5089 0.031 Uiso 1 1 calc R U . . . H13D H 0.0457 -0.6695 0.4744 0.031 Uiso 1 1 calc R U . . . C14' C -0.1384(5) -0.6078(5) 0.3808(4) 0.0299(14) Uani 1 1 d . . . . . H14D H -0.1427 -0.5910 0.3225 0.045 Uiso 1 1 calc R U . . . H14E H -0.1577 -0.5525 0.4179 0.045 Uiso 1 1 calc R U . . . H14F H -0.1829 -0.6588 0.4004 0.045 Uiso 1 1 calc R U . . . C15' C 0.0311(5) -0.5603(5) 0.3519(4) 0.0276(13) Uani 1 1 d . . . . . H15C H -0.0012 -0.4991 0.3738 0.033 Uiso 1 1 calc R U . . . H15D H 0.0941 -0.5687 0.3719 0.033 Uiso 1 1 calc R U . . . C16' C 0.0502(4) -0.5618(4) 0.2571(4) 0.0216(11) Uani 1 1 d . . . . . C17' C 0.0772(5) -0.4977(4) 0.1933(4) 0.0242(12) Uani 1 1 d . . . . . H17' H 0.0857 -0.4320 0.1985 0.029 Uiso 1 1 calc R U . . . C18' C 0.1131(4) -0.5191(4) 0.0351(4) 0.0204(11) Uani 1 1 d . . . . . C19' C 0.1353(4) -0.5859(4) -0.0296(4) 0.0252(12) Uani 1 1 d . . . . . H19' H 0.1352 -0.6514 -0.0167 0.030 Uiso 1 1 calc R U . . . C20' C 0.1578(5) -0.5559(5) -0.1134(4) 0.0298(14) Uani 1 1 d . . . . . H20' H 0.1721 -0.6009 -0.1583 0.036 Uiso 1 1 calc R U . . . C21' C 0.1594(5) -0.4596(5) -0.1318(4) 0.0309(14) Uani 1 1 d . . . . . H21' H 0.1761 -0.4391 -0.1891 0.037 Uiso 1 1 calc R U . . . C22' C 0.1365(5) -0.3945(5) -0.0668(4) 0.0330(15) Uani 1 1 d . . . . . H22' H 0.1371 -0.3291 -0.0798 0.040 Uiso 1 1 calc R U . . . C23' C 0.1125(5) -0.4226(5) 0.0178(4) 0.0285(13) Uani 1 1 d . . . . . H23' H 0.0962 -0.3773 0.0624 0.034 Uiso 1 1 calc R U . . . C24' C 0.2562(5) -0.7568(5) 0.3040(4) 0.0315(14) Uani 1 1 d . . . . . C25' C 0.3639(5) -0.7525(6) 0.2803(5) 0.0398(17) Uani 1 1 d . . . . . H25D H 0.3948 -0.8050 0.3066 0.060 Uiso 1 1 calc R U . . . H25E H 0.3841 -0.6926 0.2999 0.060 Uiso 1 1 calc R U . . . H25F H 0.3847 -0.7571 0.2184 0.060 Uiso 1 1 calc R U . . . Cl1 Cl 0.26791(11) -0.99433(11) -0.58883(9) 0.0263(3) Uani 1 1 d . . . . . O11 O 0.2982(10) -1.0834(8) -0.5586(8) 0.038(3) Uani 0.5648 1 d . . P . . O11' O 0.3236(12) -1.0505(12) -0.5371(10) 0.040(4) Uani 0.4352 1 d . . P . . O12 O 0.1907(5) -0.9457(5) -0.5304(4) 0.066(2) Uani 1 1 d . . . . . O13 O 0.3423(8) -0.9306(8) -0.5990(8) 0.046(3) Uani 0.5648 1 d . . P . . O13' O 0.3439(11) -0.9445(13) -0.6505(12) 0.059(5) Uani 0.4352 1 d . . P . . O14 O 0.2352(10) -1.0078(10) -0.6673(6) 0.046(3) Uani 0.5648 1 d . . P . . O14' O 0.2165(13) -1.0510(14) -0.6332(13) 0.062(5) Uani 0.4352 1 d . . P . . Cl2 Cl 0.03926(11) -0.74778(10) -0.26449(9) 0.0263(3) Uani 1 1 d . . . . . O21 O 0.1284(4) -0.7510(4) -0.2323(3) 0.0411(12) Uani 1 1 d . . . . . O22 O -0.0463(4) -0.7460(3) -0.1947(3) 0.0368(11) Uani 1 1 d . . . . . O23 O 0.0351(4) -0.6641(3) -0.3146(3) 0.0436(13) Uani 1 1 d . . . . . O24 O 0.0370(4) -0.8301(3) -0.3155(3) 0.0406(12) Uani 1 1 d . . . . . Cl3 Cl 0.71764(11) -0.50144(11) -0.39752(10) 0.0279(3) Uani 1 1 d . . . . . O31 O 0.7881(4) -0.5594(4) -0.3641(5) 0.0646(19) Uani 1 1 d . . . . . O32 O 0.6751(4) -0.5544(4) -0.4556(3) 0.0530(16) Uani 1 1 d . . . . . O33 O 0.7648(4) -0.4215(4) -0.4388(3) 0.0472(14) Uani 1 1 d . . . . . O34 O 0.6404(4) -0.4712(5) -0.3277(4) 0.0538(16) Uani 1 1 d . . . . . Cl4 Cl 0.64871(13) -0.74789(10) 0.26378(9) 0.0294(3) Uani 1 1 d . . . . . O41 O 0.7512(4) -0.7368(4) 0.2379(3) 0.0435(13) Uani 1 1 d . . . . . O42 O 0.6339(4) -0.8357(3) 0.3081(3) 0.0400(12) Uani 1 1 d . . . . . O43 O 0.6034(5) -0.6712(4) 0.3190(3) 0.0539(16) Uani 1 1 d . . . . . O44 O 0.6033(4) -0.7490(4) 0.1897(3) 0.0421(12) 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 Cu1 0.0227(4) 0.0200(3) 0.0137(3) -0.0009(2) -0.0030(3) 0.0001(3) N4 0.022(2) 0.025(3) 0.018(2) -0.0017(19) -0.0022(18) -0.0039(19) N3 0.026(3) 0.027(3) 0.016(2) -0.0035(19) -0.0013(19) -0.003(2) N2 0.022(2) 0.027(3) 0.014(2) -0.0007(19) -0.0035(18) -0.0011(19) N1 0.023(2) 0.022(2) 0.019(2) -0.0014(18) -0.0049(19) -0.0009(19) N5 0.033(3) 0.029(3) 0.023(3) 0.002(2) -0.003(2) 0.004(2) N6 0.027(3) 0.023(2) 0.018(2) -0.0027(19) -0.0024(19) -0.003(2) N7 0.026(3) 0.019(2) 0.022(2) -0.0006(19) -0.008(2) -0.0020(19) N8 0.023(2) 0.021(2) 0.016(2) 0.0028(18) -0.0051(18) -0.0055(19) N9 0.023(2) 0.018(2) 0.022(2) -0.0003(18) -0.0039(19) -0.0034(19) C1 0.028(3) 0.034(3) 0.014(3) 0.002(2) 0.002(2) 0.001(3) C2 0.026(3) 0.031(3) 0.023(3) -0.001(2) -0.004(2) 0.001(2) C3 0.029(3) 0.028(3) 0.020(3) 0.007(2) -0.002(2) -0.005(2) C4 0.022(3) 0.021(3) 0.021(3) -0.002(2) -0.004(2) -0.001(2) C5 0.022(3) 0.022(3) 0.022(3) 0.003(2) -0.004(2) -0.006(2) C6 0.021(3) 0.028(3) 0.017(3) -0.005(2) -0.004(2) 0.000(2) C7 0.057(5) 0.028(3) 0.026(3) -0.002(3) -0.008(3) -0.010(3) C8 0.068(5) 0.030(4) 0.037(4) -0.013(3) 0.001(4) -0.012(4) C9 0.039(4) 0.045(4) 0.026(3) -0.014(3) -0.008(3) -0.007(3) C10 0.056(5) 0.036(4) 0.020(3) -0.002(3) -0.011(3) 0.001(3) C11 0.052(4) 0.030(3) 0.024(3) -0.004(3) -0.014(3) 0.003(3) C12 0.033(3) 0.034(3) 0.015(3) 0.000(2) -0.004(2) 0.000(3) C13 0.029(3) 0.033(3) 0.015(3) -0.005(2) 0.003(2) 0.002(3) C14 0.029(3) 0.042(4) 0.020(3) -0.004(3) -0.008(2) -0.011(3) C15 0.031(3) 0.026(3) 0.022(3) -0.001(2) -0.001(2) -0.002(2) C16 0.019(3) 0.024(3) 0.024(3) -0.003(2) -0.001(2) 0.002(2) C17 0.028(3) 0.021(3) 0.026(3) -0.004(2) -0.006(2) -0.006(2) C18 0.026(3) 0.026(3) 0.022(3) 0.003(2) -0.007(2) -0.008(2) C19 0.021(3) 0.028(3) 0.028(3) 0.006(2) -0.009(2) -0.009(2) C20 0.033(3) 0.040(4) 0.023(3) -0.001(3) -0.009(3) -0.011(3) C21 0.036(4) 0.045(4) 0.028(3) 0.016(3) -0.017(3) -0.025(3) C22 0.032(3) 0.031(3) 0.041(4) 0.013(3) -0.019(3) -0.010(3) C23 0.029(3) 0.022(3) 0.037(4) 0.008(3) -0.012(3) -0.011(2) C24 0.028(3) 0.023(3) 0.019(3) 0.000(2) -0.002(2) -0.001(2) C25 0.030(3) 0.041(4) 0.027(3) 0.002(3) -0.005(3) -0.004(3) Cu1' 0.0245(4) 0.0191(3) 0.0138(3) 0.0000(2) -0.0037(3) -0.0016(3) N4' 0.027(3) 0.019(2) 0.013(2) -0.0003(17) -0.0014(18) -0.0004(19) N3' 0.025(2) 0.023(2) 0.015(2) -0.0006(18) -0.0056(19) -0.0018(19) N2' 0.025(2) 0.026(3) 0.016(2) 0.0025(19) -0.0065(19) -0.005(2) N1' 0.028(3) 0.022(2) 0.018(2) 0.0004(19) -0.0029(19) -0.001(2) N5' 0.030(3) 0.026(3) 0.040(3) -0.003(2) -0.015(2) 0.001(2) N6' 0.023(2) 0.020(2) 0.020(2) -0.0029(18) 0.0000(19) -0.0020(19) N7' 0.025(3) 0.020(2) 0.021(2) -0.0015(19) -0.0012(19) -0.0022(19) N8' 0.023(2) 0.022(2) 0.019(2) 0.0017(19) 0.0012(19) -0.0027(19) N9' 0.021(2) 0.018(2) 0.018(2) -0.0006(18) -0.0013(18) 0.0006(18) C1' 0.038(3) 0.032(3) 0.014(3) 0.002(2) -0.010(2) -0.005(3) C2' 0.029(3) 0.039(4) 0.023(3) 0.003(3) -0.006(2) -0.008(3) C3' 0.034(3) 0.020(3) 0.022(3) 0.003(2) -0.006(2) -0.005(2) C4' 0.021(3) 0.019(3) 0.024(3) 0.001(2) -0.006(2) -0.003(2) C5' 0.029(3) 0.018(3) 0.028(3) 0.001(2) -0.007(2) -0.007(2) C6' 0.019(3) 0.023(3) 0.019(3) -0.006(2) 0.003(2) -0.007(2) C7' 0.024(3) 0.030(3) 0.029(3) -0.008(3) -0.002(2) -0.006(2) C8' 0.035(4) 0.030(3) 0.034(4) -0.014(3) 0.002(3) -0.011(3) C9' 0.024(3) 0.050(4) 0.027(3) -0.012(3) -0.002(3) -0.011(3) C10' 0.024(3) 0.041(4) 0.026(3) -0.004(3) -0.006(2) -0.005(3) C11' 0.026(3) 0.028(3) 0.025(3) -0.006(2) -0.002(2) -0.006(2) C12' 0.039(4) 0.038(4) 0.012(3) -0.002(2) -0.003(2) -0.003(3) C13' 0.032(3) 0.032(3) 0.017(3) -0.004(2) -0.009(2) -0.001(3) C14' 0.027(3) 0.048(4) 0.013(3) -0.002(3) -0.002(2) 0.009(3) C15' 0.039(4) 0.028(3) 0.016(3) -0.003(2) -0.004(2) -0.009(3) C16' 0.025(3) 0.018(3) 0.022(3) 0.000(2) -0.004(2) -0.001(2) C17' 0.032(3) 0.021(3) 0.019(3) 0.000(2) -0.004(2) -0.002(2) C18' 0.017(3) 0.026(3) 0.017(3) 0.004(2) -0.001(2) -0.003(2) C19' 0.025(3) 0.027(3) 0.022(3) 0.002(2) -0.001(2) -0.003(2) C20' 0.027(3) 0.042(4) 0.020(3) -0.001(3) -0.003(2) -0.005(3) C21' 0.026(3) 0.048(4) 0.020(3) 0.010(3) -0.007(2) -0.009(3) C22' 0.035(4) 0.031(3) 0.037(4) 0.013(3) -0.014(3) -0.014(3) C23' 0.035(3) 0.030(3) 0.022(3) 0.001(2) -0.009(3) -0.008(3) C24' 0.045(4) 0.030(3) 0.020(3) 0.001(2) -0.006(3) -0.001(3) C25' 0.040(4) 0.041(4) 0.039(4) 0.004(3) -0.009(3) -0.006(3) Cl1 0.0277(7) 0.0266(7) 0.0246(7) -0.0037(6) -0.0059(6) 0.0007(6) O11 0.041(7) 0.024(6) 0.044(7) 0.007(5) 0.003(5) 0.011(4) O11' 0.041(9) 0.047(11) 0.026(7) 0.006(6) 0.006(6) 0.021(7) O12 0.070(4) 0.086(5) 0.044(3) -0.037(3) -0.030(3) 0.054(4) O13 0.028(5) 0.041(6) 0.068(8) 0.002(6) -0.006(6) -0.013(4) O13' 0.033(7) 0.070(12) 0.069(11) 0.043(10) 0.004(8) 0.000(7) O14 0.048(7) 0.075(9) 0.015(5) -0.018(5) -0.013(4) 0.018(6) O14' 0.040(8) 0.071(13) 0.076(14) -0.043(10) -0.016(9) -0.005(8) Cl2 0.0349(8) 0.0198(7) 0.0237(7) -0.0016(5) -0.0044(6) -0.0032(6) O21 0.030(3) 0.048(3) 0.048(3) -0.003(2) -0.014(2) -0.002(2) O22 0.034(3) 0.037(3) 0.034(3) -0.004(2) 0.006(2) -0.006(2) O23 0.071(4) 0.025(2) 0.032(3) 0.008(2) -0.004(2) 0.002(2) O24 0.063(3) 0.027(2) 0.029(3) -0.010(2) -0.002(2) -0.011(2) Cl3 0.0277(7) 0.0292(8) 0.0265(7) -0.0022(6) -0.0040(6) -0.0060(6) O31 0.044(3) 0.046(4) 0.107(6) 0.036(4) -0.021(3) -0.011(3) O32 0.051(3) 0.070(4) 0.033(3) -0.031(3) 0.010(2) -0.030(3) O33 0.060(4) 0.049(3) 0.043(3) 0.023(3) -0.029(3) -0.030(3) O34 0.038(3) 0.080(4) 0.041(3) -0.030(3) 0.001(2) -0.008(3) Cl4 0.0484(9) 0.0192(7) 0.0201(7) 0.0004(5) -0.0059(6) -0.0017(6) O41 0.061(4) 0.039(3) 0.032(3) 0.001(2) -0.013(2) -0.011(3) O42 0.063(4) 0.030(3) 0.029(3) 0.010(2) -0.013(2) -0.007(2) O43 0.094(5) 0.027(3) 0.035(3) -0.010(2) -0.002(3) 0.015(3) O44 0.062(3) 0.042(3) 0.027(3) 0.002(2) -0.020(2) -0.001(2) _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 Cu1 N1 1.978(5) . ? Cu1 N4 1.994(5) . ? Cu1 N3 2.056(5) . ? Cu1 N2 2.064(5) . ? Cu1 N5 2.336(6) . ? N4 N8 1.317(7) . ? N4 C16 1.359(8) . ? N3 C14 1.485(8) . ? N3 C15 1.495(8) . ? N3 C13 1.508(7) . ? N2 C2 1.483(7) . ? N2 C3 1.491(8) . ? N2 C1 1.501(7) . ? N1 N6 1.325(7) . ? N1 C4 1.364(7) . ? N5 C24 1.117(8) . ? N6 N7 1.345(7) . ? N7 C5 1.358(7) . ? N7 C6 1.425(7) . ? N8 N9 1.342(7) . ? N9 C17 1.363(8) . ? N9 C18 1.434(7) . ? C1 C12 1.519(9) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.497(8) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.355(8) . ? C5 H5 0.9500 . ? C6 C11 1.377(9) . ? C6 C7 1.380(9) . ? C7 C8 1.382(10) . ? C7 H7 0.9500 . ? C8 C9 1.366(11) . ? C8 H8 0.9500 . ? C9 C10 1.383(10) . ? C9 H9 0.9500 . ? C10 C11 1.388(9) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.517(9) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.496(8) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.360(8) . ? C17 H17 0.9500 . ? C18 C19 1.386(9) . ? C18 C23 1.394(9) . ? C19 C20 1.390(9) . ? C19 H19 0.9500 . ? C20 C21 1.388(10) . ? C20 H20 0.9500 . ? C21 C22 1.379(11) . ? C21 H21 0.9500 . ? C22 C23 1.389(9) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C25 1.447(9) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? Cu1' N1' 1.972(5) . ? Cu1' N4' 1.975(5) . ? Cu1' N2' 2.050(5) . ? Cu1' N3' 2.054(5) . ? Cu1' N5' 2.305(5) . ? N4' N8' 1.324(6) . ? N4' C16' 1.357(7) . ? N3' C14' 1.485(8) . ? N3' C15' 1.504(8) . ? N3' C13' 1.503(7) . ? N2' C3' 1.487(8) . ? N2' C2' 1.499(8) . ? N2' C1' 1.504(7) . ? N1' N6' 1.319(7) . ? N1' C4' 1.362(7) . ? N5' C24' 1.149(9) . ? N6' N7' 1.334(7) . ? N7' C5' 1.366(7) . ? N7' C6' 1.436(7) . ? N8' N9' 1.343(7) . ? N9' C17' 1.361(7) . ? N9' C18' 1.426(7) . ? C1' C12' 1.517(9) . ? C1' H1'1 0.9900 . ? C1' H1'2 0.9900 . ? C2' H2'1 0.9800 . ? C2' H2'2 0.9800 . ? C2' H2'3 0.9800 . ? C3' C4' 1.498(8) . ? C3' H3'1 0.9900 . ? C3' H3'2 0.9900 . ? C4' C5' 1.351(8) . ? C5' H5' 0.9500 . ? C6' C7' 1.383(9) . ? C6' C11' 1.402(9) . ? C7' C8' 1.388(9) . ? C7' H7' 0.9500 . ? C8' C9' 1.390(10) . ? C8' H8' 0.9500 . ? C9' C10' 1.392(10) . ? C9' H9' 0.9500 . ? C10' C11' 1.382(9) . ? C10' H10' 0.9500 . ? C11' H11' 0.9500 . ? C12' C13' 1.517(9) . ? C12' H12C 0.9900 . ? C12' H12D 0.9900 . ? C13' H13C 0.9900 . ? C13' H13D 0.9900 . ? C14' H14D 0.9800 . ? C14' H14E 0.9800 . ? C14' H14F 0.9800 . ? C15' C16' 1.494(8) . ? C15' H15C 0.9900 . ? C15' H15D 0.9900 . ? C16' C17' 1.373(8) . ? C17' H17' 0.9500 . ? C18' C19' 1.388(8) . ? C18' C23' 1.396(8) . ? C19' C20' 1.390(8) . ? C19' H19' 0.9500 . ? C20' C21' 1.396(10) . ? C20' H20' 0.9500 . ? C21' C22' 1.376(10) . ? C21' H21' 0.9500 . ? C22' C23' 1.395(9) . ? C22' H22' 0.9500 . ? C23' H23' 0.9500 . ? C24' C25' 1.464(10) . ? C25' H25D 0.9800 . ? C25' H25E 0.9800 . ? C25' H25F 0.9800 . ? Cl1 O13 1.383(11) . ? Cl1 O14' 1.386(16) . ? Cl1 O11 1.428(12) . ? Cl1 O12 1.425(6) . ? Cl1 O14 1.440(11) . ? Cl1 O11' 1.456(16) . ? Cl1 O13' 1.491(14) . ? O11 O11' 0.725(16) . ? O13 O13' 0.847(18) . ? O14 O14' 0.834(19) . ? Cl2 O21 1.430(5) . ? Cl2 O24 1.434(5) . ? Cl2 O23 1.438(5) . ? Cl2 O22 1.454(5) . ? Cl3 O33 1.427(5) . ? Cl3 O32 1.431(5) . ? Cl3 O31 1.433(6) . ? Cl3 O34 1.435(5) . ? Cl4 O41 1.409(6) . ? Cl4 O42 1.435(5) . ? Cl4 O43 1.444(5) . ? Cl4 O44 1.455(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N4 99.0(2) . . ? N1 Cu1 N3 172.8(2) . . ? N4 Cu1 N3 81.7(2) . . ? N1 Cu1 N2 81.8(2) . . ? N4 Cu1 N2 171.2(2) . . ? N3 Cu1 N2 96.4(2) . . ? N1 Cu1 N5 89.6(2) . . ? N4 Cu1 N5 92.09(19) . . ? N3 Cu1 N5 97.6(2) . . ? N2 Cu1 N5 96.69(19) . . ? N8 N4 C16 111.2(5) . . ? N8 N4 Cu1 135.2(4) . . ? C16 N4 Cu1 113.5(4) . . ? C14 N3 C15 107.8(5) . . ? C14 N3 C13 111.5(5) . . ? C15 N3 C13 107.6(5) . . ? C14 N3 Cu1 109.9(4) . . ? C15 N3 Cu1 106.1(4) . . ? C13 N3 Cu1 113.6(4) . . ? C2 N2 C3 108.7(5) . . ? C2 N2 C1 111.3(5) . . ? C3 N2 C1 107.8(5) . . ? C2 N2 Cu1 108.6(4) . . ? C3 N2 Cu1 106.3(3) . . ? C1 N2 Cu1 113.9(4) . . ? N6 N1 C4 110.9(5) . . ? N6 N1 Cu1 134.7(4) . . ? C4 N1 Cu1 114.3(4) . . ? C24 N5 Cu1 162.4(5) . . ? N1 N6 N7 105.0(4) . . ? N6 N7 C5 111.6(5) . . ? N6 N7 C6 119.5(5) . . ? C5 N7 C6 129.0(5) . . ? N4 N8 N9 104.9(5) . . ? N8 N9 C17 112.0(5) . . ? N8 N9 C18 119.1(5) . . ? C17 N9 C18 128.9(5) . . ? N2 C1 C12 114.2(5) . . ? N2 C1 H1A 108.7 . . ? C12 C1 H1A 108.7 . . ? N2 C1 H1B 108.7 . . ? C12 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? N2 C2 H2A 109.5 . . ? N2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N2 C3 C4 109.1(5) . . ? N2 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? N2 C3 H3B 109.9 . . ? C4 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? C5 C4 N1 107.1(5) . . ? C5 C4 C3 137.1(6) . . ? N1 C4 C3 115.8(5) . . ? C4 C5 N7 105.5(5) . . ? C4 C5 H5 127.2 . . ? N7 C5 H5 127.2 . . ? C11 C6 C7 120.3(6) . . ? C11 C6 N7 119.9(5) . . ? C7 C6 N7 119.6(5) . . ? C8 C7 C6 119.8(7) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C9 C8 C7 120.3(7) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 120.0(6) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C11 120.2(7) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C6 C11 C10 119.3(6) . . ? C6 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C13 C12 C1 114.1(5) . . ? C13 C12 H12A 108.7 . . ? C1 C12 H12A 108.7 . . ? C13 C12 H12B 108.7 . . ? C1 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? N3 C13 C12 113.6(5) . . ? N3 C13 H13A 108.8 . . ? C12 C13 H13A 108.8 . . ? N3 C13 H13B 108.8 . . ? C12 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? N3 C14 H14A 109.5 . . ? N3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N3 C15 C16 108.2(5) . . ? N3 C15 H15A 110.1 . . ? C16 C15 H15A 110.1 . . ? N3 C15 H15B 110.1 . . ? C16 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? N4 C16 C17 107.4(5) . . ? N4 C16 C15 116.2(5) . . ? C17 C16 C15 136.3(6) . . ? N9 C17 C16 104.5(5) . . ? N9 C17 H17 127.7 . . ? C16 C17 H17 127.7 . . ? C19 C18 C23 121.6(6) . . ? C19 C18 N9 119.4(5) . . ? C23 C18 N9 119.0(6) . . ? C18 C19 C20 118.8(6) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? C19 C20 C21 120.0(6) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C22 C21 C20 120.6(6) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 120.3(6) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C22 C23 C18 118.6(7) . . ? C22 C23 H23 120.7 . . ? C18 C23 H23 120.7 . . ? N5 C24 C25 179.2(7) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N1' Cu1' N4' 98.2(2) . . ? N1' Cu1' N2' 82.1(2) . . ? N4' Cu1' N2' 171.1(2) . . ? N1' Cu1' N3' 172.3(2) . . ? N4' Cu1' N3' 81.75(19) . . ? N2' Cu1' N3' 96.7(2) . . ? N1' Cu1' N5' 91.8(2) . . ? N4' Cu1' N5' 89.7(2) . . ? N2' Cu1' N5' 99.2(2) . . ? N3' Cu1' N5' 95.9(2) . . ? N8' N4' C16' 111.1(5) . . ? N8' N4' Cu1' 134.6(4) . . ? C16' N4' Cu1' 114.3(4) . . ? C14' N3' C15' 108.1(5) . . ? C14' N3' C13' 110.5(5) . . ? C15' N3' C13' 107.3(4) . . ? C14' N3' Cu1' 111.0(4) . . ? C15' N3' Cu1' 106.2(4) . . ? C13' N3' Cu1' 113.4(4) . . ? C3' N2' C2' 107.9(5) . . ? C3' N2' C1' 107.9(5) . . ? C2' N2' C1' 110.8(5) . . ? C3' N2' Cu1' 107.2(3) . . ? C2' N2' Cu1' 108.7(4) . . ? C1' N2' Cu1' 114.0(4) . . ? N6' N1' C4' 110.5(5) . . ? N6' N1' Cu1' 135.0(4) . . ? C4' N1' Cu1' 114.3(4) . . ? C24' N5' Cu1' 156.3(5) . . ? N1' N6' N7' 105.5(5) . . ? N6' N7' C5' 111.6(5) . . ? N6' N7' C6' 119.6(5) . . ? C5' N7' C6' 128.8(5) . . ? N4' N8' N9' 104.7(4) . . ? N8' N9' C17' 112.7(5) . . ? N8' N9' C18' 118.9(5) . . ? C17' N9' C18' 128.3(5) . . ? N2' C1' C12' 114.6(5) . . ? N2' C1' H1'1 108.6 . . ? C12' C1' H1'1 108.6 . . ? N2' C1' H1'2 108.6 . . ? C12' C1' H1'2 108.6 . . ? H1'1 C1' H1'2 107.6 . . ? N2' C2' H2'1 109.5 . . ? N2' C2' H2'2 109.5 . . ? H2'1 C2' H2'2 109.5 . . ? N2' C2' H2'3 109.5 . . ? H2'1 C2' H2'3 109.5 . . ? H2'2 C2' H2'3 109.5 . . ? N2' C3' C4' 108.8(5) . . ? N2' C3' H3'1 109.9 . . ? C4' C3' H3'1 109.9 . . ? N2' C3' H3'2 109.9 . . ? C4' C3' H3'2 109.9 . . ? H3'1 C3' H3'2 108.3 . . ? C5' C4' N1' 107.5(5) . . ? C5' C4' C3' 136.3(5) . . ? N1' C4' C3' 116.1(5) . . ? C4' C5' N7' 104.9(5) . . ? C4' C5' H5' 127.6 . . ? N7' C5' H5' 127.6 . . ? C7' C6' C11' 121.7(6) . . ? C7' C6' N7' 119.9(5) . . ? C11' C6' N7' 118.4(5) . . ? C6' C7' C8' 118.3(6) . . ? C6' C7' H7' 120.8 . . ? C8' C7' H7' 120.8 . . ? C7' C8' C9' 121.0(7) . . ? C7' C8' H8' 119.5 . . ? C9' C8' H8' 119.5 . . ? C10' C9' C8' 120.0(6) . . ? C10' C9' H9' 120.0 . . ? C8' C9' H9' 120.0 . . ? C11' C10' C9' 119.9(6) . . ? C11' C10' H10' 120.0 . . ? C9' C10' H10' 120.0 . . ? C10' C11' C6' 119.1(6) . . ? C10' C11' H11' 120.5 . . ? C6' C11' H11' 120.5 . . ? C13' C12' C1' 115.7(5) . . ? C13' C12' H12C 108.4 . . ? C1' C12' H12C 108.4 . . ? C13' C12' H12D 108.4 . . ? C1' C12' H12D 108.4 . . ? H12C C12' H12D 107.4 . . ? N3' C13' C12' 114.1(5) . . ? N3' C13' H13C 108.7 . . ? C12' C13' H13C 108.7 . . ? N3' C13' H13D 108.7 . . ? C12' C13' H13D 108.7 . . ? H13C C13' H13D 107.6 . . ? N3' C14' H14D 109.5 . . ? N3' C14' H14E 109.5 . . ? H14D C14' H14E 109.5 . . ? N3' C14' H14F 109.5 . . ? H14D C14' H14F 109.5 . . ? H14E C14' H14F 109.5 . . ? C16' C15' N3' 107.7(5) . . ? C16' C15' H15C 110.2 . . ? N3' C15' H15C 110.2 . . ? C16' C15' H15D 110.2 . . ? N3' C15' H15D 110.2 . . ? H15C C15' H15D 108.5 . . ? N4' C16' C17' 107.6(5) . . ? N4' C16' C15' 116.2(5) . . ? C17' C16' C15' 136.1(5) . . ? N9' C17' C16' 103.9(5) . . ? N9' C17' H17' 128.0 . . ? C16' C17' H17' 128.0 . . ? C19' C18' C23' 121.4(5) . . ? C19' C18' N9' 119.1(5) . . ? C23' C18' N9' 119.5(5) . . ? C18' C19' C20' 119.2(6) . . ? C18' C19' H19' 120.4 . . ? C20' C19' H19' 120.4 . . ? C19' C20' C21' 120.2(6) . . ? C19' C20' H20' 119.9 . . ? C21' C20' H20' 119.9 . . ? C22' C21' C20' 119.8(6) . . ? C22' C21' H21' 120.1 . . ? C20' C21' H21' 120.1 . . ? C21' C22' C23' 121.3(6) . . ? C21' C22' H22' 119.3 . . ? C23' C22' H22' 119.3 . . ? C22' C23' C18' 118.1(6) . . ? C22' C23' H23' 120.9 . . ? C18' C23' H23' 120.9 . . ? N5' C24' C25' 179.9(9) . . ? C24' C25' H25D 109.5 . . ? C24' C25' H25E 109.5 . . ? H25D C25' H25E 109.5 . . ? C24' C25' H25F 109.5 . . ? H25D C25' H25F 109.5 . . ? H25E C25' H25F 109.5 . . ? O13 Cl1 O14' 143.1(10) . . ? O13 Cl1 O11 112.0(7) . . ? O14' Cl1 O11 82.3(10) . . ? O13 Cl1 O12 101.9(6) . . ? O14' Cl1 O12 102.7(8) . . ? O11 Cl1 O12 113.7(6) . . ? O13 Cl1 O14 110.9(8) . . ? O14' Cl1 O14 34.3(8) . . ? O11 Cl1 O14 109.5(8) . . ? O12 Cl1 O14 108.7(5) . . ? O13 Cl1 O11' 87.7(9) . . ? O14' Cl1 O11' 111.4(11) . . ? O11 Cl1 O11' 29.1(6) . . ? O12 Cl1 O11' 105.7(6) . . ? O14 Cl1 O11' 135.9(8) . . ? O13 Cl1 O13' 34.0(8) . . ? O14' Cl1 O13' 109.1(12) . . ? O11 Cl1 O13' 116.6(8) . . ? O12 Cl1 O13' 122.9(8) . . ? O14 Cl1 O13' 78.2(10) . . ? O11' Cl1 O13' 105.1(9) . . ? O11' O11 Cl1 78(2) . . ? O11 O11' Cl1 73(2) . . ? O13' O13 Cl1 79.9(15) . . ? O13 O13' Cl1 66.0(13) . . ? O14' O14 Cl1 69.3(15) . . ? O14 O14' Cl1 76.4(16) . . ? O21 Cl2 O24 109.5(3) . . ? O21 Cl2 O23 109.4(3) . . ? O24 Cl2 O23 110.0(3) . . ? O21 Cl2 O22 110.2(3) . . ? O24 Cl2 O22 108.6(3) . . ? O23 Cl2 O22 109.1(3) . . ? O33 Cl3 O32 110.4(3) . . ? O33 Cl3 O31 109.6(3) . . ? O32 Cl3 O31 110.5(4) . . ? O33 Cl3 O34 110.0(4) . . ? O32 Cl3 O34 108.5(3) . . ? O31 Cl3 O34 107.8(4) . . ? O41 Cl4 O42 108.4(3) . . ? O41 Cl4 O43 110.6(4) . . ? O42 Cl4 O43 109.7(3) . . ? O41 Cl4 O44 109.7(3) . . ? O42 Cl4 O44 109.7(3) . . ? O43 Cl4 O44 108.8(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 N1 N6 N7 0.4(6) . . . . ? Cu1 N1 N6 N7 176.5(4) . . . . ? N1 N6 N7 C5 0.0(6) . . . . ? N1 N6 N7 C6 178.8(5) . . . . ? C16 N4 N8 N9 0.8(6) . . . . ? Cu1 N4 N8 N9 -177.8(4) . . . . ? N4 N8 N9 C17 -0.6(6) . . . . ? N4 N8 N9 C18 178.0(5) . . . . ? C2 N2 C1 C12 -67.5(7) . . . . ? C3 N2 C1 C12 173.3(5) . . . . ? Cu1 N2 C1 C12 55.6(6) . . . . ? C2 N2 C3 C4 79.9(6) . . . . ? C1 N2 C3 C4 -159.3(5) . . . . ? Cu1 N2 C3 C4 -36.8(5) . . . . ? N6 N1 C4 C5 -0.6(7) . . . . ? Cu1 N1 C4 C5 -177.6(4) . . . . ? N6 N1 C4 C3 177.4(5) . . . . ? Cu1 N1 C4 C3 0.4(7) . . . . ? N2 C3 C4 C5 -157.4(7) . . . . ? N2 C3 C4 N1 25.3(7) . . . . ? N1 C4 C5 N7 0.6(6) . . . . ? C3 C4 C5 N7 -176.8(7) . . . . ? N6 N7 C5 C4 -0.4(7) . . . . ? C6 N7 C5 C4 -179.0(5) . . . . ? N6 N7 C6 C11 8.0(8) . . . . ? C5 N7 C6 C11 -173.4(6) . . . . ? N6 N7 C6 C7 -168.8(6) . . . . ? C5 N7 C6 C7 9.8(9) . . . . ? C11 C6 C7 C8 1.8(11) . . . . ? N7 C6 C7 C8 178.6(7) . . . . ? C6 C7 C8 C9 -1.2(12) . . . . ? C7 C8 C9 C10 -0.1(12) . . . . ? C8 C9 C10 C11 0.7(12) . . . . ? C7 C6 C11 C10 -1.2(10) . . . . ? N7 C6 C11 C10 -178.0(6) . . . . ? C9 C10 C11 C6 -0.1(11) . . . . ? N2 C1 C12 C13 -70.1(7) . . . . ? C14 N3 C13 C12 67.3(7) . . . . ? C15 N3 C13 C12 -174.6(5) . . . . ? Cu1 N3 C13 C12 -57.5(6) . . . . ? C1 C12 C13 N3 71.1(7) . . . . ? C14 N3 C15 C16 -78.3(6) . . . . ? C13 N3 C15 C16 161.2(5) . . . . ? Cu1 N3 C15 C16 39.4(5) . . . . ? N8 N4 C16 C17 -0.7(7) . . . . ? Cu1 N4 C16 C17 178.2(4) . . . . ? N8 N4 C16 C15 -177.1(5) . . . . ? Cu1 N4 C16 C15 1.8(7) . . . . ? N3 C15 C16 N4 -28.4(7) . . . . ? N3 C15 C16 C17 156.5(7) . . . . ? N8 N9 C17 C16 0.2(6) . . . . ? C18 N9 C17 C16 -178.2(5) . . . . ? N4 C16 C17 N9 0.3(6) . . . . ? C15 C16 C17 N9 175.6(7) . . . . ? N8 N9 C18 C19 14.9(8) . . . . ? C17 N9 C18 C19 -166.8(6) . . . . ? N8 N9 C18 C23 -163.9(5) . . . . ? C17 N9 C18 C23 14.4(9) . . . . ? C23 C18 C19 C20 1.6(9) . . . . ? N9 C18 C19 C20 -177.2(5) . . . . ? C18 C19 C20 C21 -0.9(9) . . . . ? C19 C20 C21 C22 -0.2(9) . . . . ? C20 C21 C22 C23 0.5(10) . . . . ? C21 C22 C23 C18 0.2(9) . . . . ? C19 C18 C23 C22 -1.3(9) . . . . ? N9 C18 C23 C22 177.5(5) . . . . ? C4' N1' N6' N7' -0.3(6) . . . . ? Cu1' N1' N6' N7' 175.3(4) . . . . ? N1' N6' N7' C5' 0.6(6) . . . . ? N1' N6' N7' C6' -178.9(5) . . . . ? C16' N4' N8' N9' 0.7(6) . . . . ? Cu1' N4' N8' N9' -177.8(4) . . . . ? N4' N8' N9' C17' -1.1(6) . . . . ? N4' N8' N9' C18' -178.0(5) . . . . ? C3' N2' C1' C12' 173.5(5) . . . . ? C2' N2' C1' C12' -68.6(7) . . . . ? Cu1' N2' C1' C12' 54.5(6) . . . . ? C2' N2' C3' C4' 81.7(6) . . . . ? C1' N2' C3' C4' -158.5(5) . . . . ? Cu1' N2' C3' C4' -35.3(5) . . . . ? N6' N1' C4' C5' -0.2(7) . . . . ? Cu1' N1' C4' C5' -176.8(4) . . . . ? N6' N1' C4' C3' 176.6(5) . . . . ? Cu1' N1' C4' C3' 0.0(7) . . . . ? N2' C3' C4' C5' -160.1(7) . . . . ? N2' C3' C4' N1' 24.4(7) . . . . ? N1' C4' C5' N7' 0.5(6) . . . . ? C3' C4' C5' N7' -175.2(7) . . . . ? N6' N7' C5' C4' -0.7(7) . . . . ? C6' N7' C5' C4' 178.7(5) . . . . ? N6' N7' C6' C7' 170.2(5) . . . . ? C5' N7' C6' C7' -9.2(9) . . . . ? N6' N7' C6' C11' -9.4(8) . . . . ? C5' N7' C6' C11' 171.2(6) . . . . ? C11' C6' C7' C8' 1.5(9) . . . . ? N7' C6' C7' C8' -178.2(5) . . . . ? C6' C7' C8' C9' -1.4(10) . . . . ? C7' C8' C9' C10' 0.5(10) . . . . ? C8' C9' C10' C11' 0.3(9) . . . . ? C9' C10' C11' C6' -0.3(9) . . . . ? C7' C6' C11' C10' -0.6(9) . . . . ? N7' C6' C11' C10' 179.0(5) . . . . ? N2' C1' C12' C13' -67.1(7) . . . . ? C14' N3' C13' C12' 68.8(7) . . . . ? C15' N3' C13' C12' -173.6(5) . . . . ? Cu1' N3' C13' C12' -56.6(6) . . . . ? C1' C12' C13' N3' 68.4(7) . . . . ? C14' N3' C15' C16' -80.6(6) . . . . ? C13' N3' C15' C16' 160.2(5) . . . . ? Cu1' N3' C15' C16' 38.6(6) . . . . ? N8' N4' C16' C17' -0.1(7) . . . . ? Cu1' N4' C16' C17' 178.8(4) . . . . ? N8' N4' C16' C15' -176.9(5) . . . . ? Cu1' N4' C16' C15' 2.0(7) . . . . ? N3' C15' C16' N4' -28.0(7) . . . . ? N3' C15' C16' C17' 156.4(7) . . . . ? N8' N9' C17' C16' 1.0(7) . . . . ? C18' N9' C17' C16' 177.5(5) . . . . ? N4' C16' C17' N9' -0.5(7) . . . . ? C15' C16' C17' N9' 175.3(7) . . . . ? N8' N9' C18' C19' -12.8(8) . . . . ? C17' N9' C18' C19' 170.9(6) . . . . ? N8' N9' C18' C23' 166.1(5) . . . . ? C17' N9' C18' C23' -10.2(9) . . . . ? C23' C18' C19' C20' 0.2(9) . . . . ? N9' C18' C19' C20' 179.1(5) . . . . ? C18' C19' C20' C21' 1.0(9) . . . . ? C19' C20' C21' C22' -1.4(10) . . . . ? C20' C21' C22' C23' 0.6(10) . . . . ? C21' C22' C23' C18' 0.6(10) . . . . ? C19' C18' C23' C22' -1.0(9) . . . . ? N9' C18' C23' C22' -179.9(5) . . . . ? O13 Cl1 O11 O11' 35(2) . . . . ? O14' Cl1 O11 O11' 180(2) . . . . ? O12 Cl1 O11 O11' -80(2) . . . . ? O14 Cl1 O11 O11' 158.7(19) . . . . ? O13' Cl1 O11 O11' 72(2) . . . . ? O13 Cl1 O11' O11 -148(2) . . . . ? O14' Cl1 O11' O11 0(2) . . . . ? O12 Cl1 O11' O11 110.7(19) . . . . ? O14 Cl1 O11' O11 -30(3) . . . . ? O13' Cl1 O11' O11 -118(2) . . . . ? O14' Cl1 O13 O13' -2(3) . . . . ? O11 Cl1 O13 O13' 105.3(17) . . . . ? O12 Cl1 O13 O13' -132.8(16) . . . . ? O14 Cl1 O13 O13' -17.3(18) . . . . ? O11' Cl1 O13 O13' 121.7(17) . . . . ? O14' Cl1 O13' O13 178.8(16) . . . . ? O11 Cl1 O13' O13 -90.4(18) . . . . ? O12 Cl1 O13' O13 58.8(17) . . . . ? O14 Cl1 O13' O13 163.5(18) . . . . ? O11' Cl1 O13' O13 -61.7(18) . . . . ? O13 Cl1 O14 O14' 163.6(18) . . . . ? O11 Cl1 O14 O14' 40(2) . . . . ? O12 Cl1 O14 O14' -85.2(19) . . . . ? O11' Cl1 O14 O14' 54(2) . . . . ? O13' Cl1 O14 O14' 154(2) . . . . ? O13 Cl1 O14' O14 -26(3) . . . . ? O11 Cl1 O14' O14 -142.7(19) . . . . ? O12 Cl1 O14' O14 104.6(17) . . . . ? O11' Cl1 O14' O14 -142.7(17) . . . . ? O13' Cl1 O14' O14 -27(2) . . . . ? _refine_diff_density_max 1.718 _refine_diff_density_min -1.107 _refine_diff_density_rms 0.178 _shelxl_version_number 2013-2 _database_code_depnum_ccdc_archive 'CCDC 851238' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_update_record ; 2013-09-02 # Formatted by publCIF ; # publcif _publ_body_element loop end _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common '[CuL8(DMF)2](ClO4)2' _chemical_melting_point ? _chemical_formula_moiety 'C31 H46 Cu N10 O4, 2(Cl O4)' _chemical_formula_sum 'C31 H46 Cl2 Cu N10 O12' _chemical_formula_weight 885.22 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.806(3) _cell_length_b 12.898(3) _cell_length_c 14.296(3) _cell_angle_alpha 80.451(10) _cell_angle_beta 85.534(14) _cell_angle_gamma 73.186(12) _cell_volume 1880.1(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7603 _cell_measurement_theta_min 1.67 _cell_measurement_theta_max 28.00 _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 922 _exptl_absorpt_coefficient_mu 0.799 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.794 _exptl_absorpt_correction_T_max 0.916 _exptl_absorpt_process_details 'ABSORB, De Titta (1985)' _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 KappaCCD _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17715 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0590 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 28.00 _reflns_number_total 9063 _reflns_number_gt 7603 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect Bruker-Nonius' _computing_cell_refinement HKL2000 _computing_data_reduction HKL2000 _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0391P)^2^+1.9251P] 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 9061 _refine_ls_number_parameters 580 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1139 _refine_ls_wR_factor_gt 0.1067 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.005 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.90330(3) 0.26392(2) 0.27499(2) 0.02141(8) Uani 1 1 d . . . . . O2 O 1.19986(16) -0.41605(14) 0.06919(12) 0.0277(4) Uani 1 1 d . . . . . O3 O 0.32596(18) -0.16100(14) 0.35536(13) 0.0327(4) Uani 1 1 d . . . . . N1 N 0.77752(19) 0.18958(16) 0.34569(14) 0.0241(4) Uani 1 1 d . . . . . N2 N 0.78142(19) 0.39902(16) 0.32685(15) 0.0259(4) Uani 1 1 d . . . . . N3 N 1.02580(18) 0.34536(16) 0.20028(14) 0.0230(4) Uani 1 1 d . . . . . N4 N 1.02130(18) 0.13828(16) 0.21992(14) 0.0242(4) Uani 1 1 d . . . . . N5 N 1.01459(19) 0.04180(16) 0.20711(14) 0.0248(4) Uani 1 1 d . . . . . N6 N 1.12111(19) 0.00073(17) 0.15577(14) 0.0254(4) Uani 1 1 d . . . . . N7 N 0.73843(19) 0.10621(16) 0.33239(14) 0.0244(4) Uani 1 1 d . . . . . N8 N 0.62265(19) 0.11965(16) 0.37762(14) 0.0231(4) Uani 1 1 d . . . . . C1 C 0.9270(3) 0.5192(2) 0.2695(2) 0.0317(5) Uani 1 1 d . . . . . H1A H 0.8748 0.5456 0.2136 0.038 Uiso 1 1 calc R U . . . H1B H 0.9508 0.5807 0.2860 0.038 Uiso 1 1 calc R U . . . C2 C 1.0480(2) 0.4333(2) 0.24585(18) 0.0281(5) Uani 1 1 d . . . . . H2A H 1.1033 0.4690 0.2039 0.034 Uiso 1 1 calc R U . . . H2B H 1.0940 0.4002 0.3039 0.034 Uiso 1 1 calc R U . . . C3 C 0.9765(2) 0.3898(2) 0.10390(17) 0.0309(5) Uani 1 1 d . . . . . H3A H 0.8927 0.4412 0.1082 0.046 Uiso 1 1 calc R U . . . H3B H 0.9701 0.3309 0.0731 0.046 Uiso 1 1 calc R U . . . H3C H 1.0349 0.4260 0.0678 0.046 Uiso 1 1 calc R U . . . C4 C 1.1536(2) 0.2633(2) 0.19092(18) 0.0274(5) Uani 1 1 d . . . . . H4A H 1.2024 0.2887 0.1365 0.033 Uiso 1 1 calc R U . . . H4B H 1.2029 0.2530 0.2473 0.033 Uiso 1 1 calc R U . . . C5 C 1.1306(2) 0.1589(2) 0.17861(17) 0.0265(5) Uani 1 1 d . . . . . C6 C 1.1956(2) 0.0708(2) 0.13648(18) 0.0282(5) Uani 1 1 d . . . . . H6 H 1.2738 0.0607 0.1021 0.034 Uiso 1 1 calc R U . . . C7 C 1.1441(2) -0.1059(2) 0.13083(17) 0.0252(5) Uani 1 1 d . . . . . C8 C 1.2690(2) -0.1717(2) 0.12587(17) 0.0250(5) Uani 1 1 d . . . . . H8 H 1.3378 -0.1458 0.1367 0.030 Uiso 1 1 calc R U . . . C9 C 1.2916(2) -0.2764(2) 0.10472(17) 0.0267(5) Uani 1 1 d . . . . . H9 H 1.3759 -0.3212 0.1005 0.032 Uiso 1 1 calc R U . . . C10 C 1.1882(2) -0.3145(2) 0.08982(16) 0.0251(5) Uani 1 1 d . . . . . C11 C 1.3271(3) -0.4817(2) 0.0503(2) 0.0352(6) Uani 1 1 d . . . . . H11A H 1.3677 -0.4427 0.0000 0.053 Uiso 1 1 calc R U . . . H11B H 1.3228 -0.5488 0.0318 0.053 Uiso 1 1 calc R U . . . H11C H 1.3768 -0.4980 0.1065 0.053 Uiso 1 1 calc R U . . . C12 C 1.0621(2) -0.2475(2) 0.09607(17) 0.0281(5) Uani 1 1 d . . . . . H12 H 0.9928 -0.2736 0.0872 0.034 Uiso 1 1 calc R U . . . C13 C 1.0404(2) -0.1433(2) 0.11529(18) 0.0276(5) Uani 1 1 d . . . . . H13 H 0.9564 -0.0975 0.1179 0.033 Uiso 1 1 calc R U . . . C14 C 0.8467(3) 0.4776(2) 0.35044(19) 0.0306(5) Uani 1 1 d . . . . . H14A H 0.9023 0.4424 0.4035 0.037 Uiso 1 1 calc R U . . . H14B H 0.7815 0.5397 0.3707 0.037 Uiso 1 1 calc R U . . . C15 C 0.6772(2) 0.4572(2) 0.2597(2) 0.0326(6) Uani 1 1 d . . . . . H15A H 0.6282 0.4085 0.2506 0.049 Uiso 1 1 calc R U . . . H15B H 0.7146 0.4813 0.1999 0.049 Uiso 1 1 calc R U . . . H15C H 0.6213 0.5194 0.2849 0.049 Uiso 1 1 calc R U . . . C16 C 0.7192(2) 0.3554(2) 0.41534(18) 0.0289(5) Uani 1 1 d . . . . . H16A H 0.7774 0.3377 0.4677 0.035 Uiso 1 1 calc R U . . . H16B H 0.6406 0.4095 0.4314 0.035 Uiso 1 1 calc R U . . . C17 C 0.6890(2) 0.2558(2) 0.39736(17) 0.0258(5) Uani 1 1 d . . . . . C18 C 0.5887(2) 0.21140(19) 0.41835(17) 0.0251(5) Uani 1 1 d . . . . . H18 H 0.5131 0.2384 0.4532 0.030 Uiso 1 1 calc R U . . . C19 C 0.5485(2) 0.04467(19) 0.37315(16) 0.0235(5) Uani 1 1 d . . . . . C20 C 0.6101(2) -0.0597(2) 0.35637(18) 0.0294(5) Uani 1 1 d . . . . . H20 H 0.6999 -0.0825 0.3500 0.035 Uiso 1 1 calc R U . . . C21 C 0.5385(2) -0.1310(2) 0.34884(18) 0.0291(5) Uani 1 1 d . . . . . H21 H 0.5801 -0.2015 0.3365 0.035 Uiso 1 1 calc R U . . . C22 C 0.4052(2) -0.0975(2) 0.35971(17) 0.0269(5) Uani 1 1 d . . . . . C23 C 0.3856(3) -0.2741(2) 0.34672(19) 0.0327(6) Uani 1 1 d . . . . . H23A H 0.4370 -0.2789 0.2889 0.049 Uiso 1 1 calc R U . . . H23B H 0.3198 -0.3105 0.3457 0.049 Uiso 1 1 calc R U . . . H23C H 0.4397 -0.3085 0.3997 0.049 Uiso 1 1 calc R U . . . C24 C 0.3434(2) 0.0092(2) 0.37619(18) 0.0293(5) Uani 1 1 d . . . . . H24 H 0.2537 0.0323 0.3830 0.035 Uiso 1 1 calc R U . . . C25 C 0.4148(2) 0.0809(2) 0.38249(17) 0.0271(5) Uani 1 1 d . . . . . H25 H 0.3738 0.1522 0.3928 0.033 Uiso 1 1 calc R U . . . Cl2 Cl 0.31283(6) 0.44874(5) 0.38724(5) 0.03334(15) Uani 1 1 d . . . . . O21 O 0.19191(17) 0.52717(17) 0.39681(16) 0.0426(5) Uani 1 1 d . . . . . O22 O 0.2787(4) 0.3492(3) 0.4386(6) 0.067(2) Uani 0.533(8) 1 d . . P . . O23 O 0.3538(5) 0.4350(8) 0.2990(3) 0.076(3) Uani 0.533(8) 1 d . . P . . O24 O 0.4065(13) 0.4618(12) 0.4420(12) 0.044(2) Uani 0.533(8) 1 d . . P . . O2A O 0.3126(4) 0.3485(3) 0.3587(4) 0.0343(16) Uani 0.467(8) 1 d . . P . . O2B O 0.3748(7) 0.5032(5) 0.2997(6) 0.073(2) Uani 0.467(8) 1 d . . P . . O2C O 0.3948(17) 0.4384(15) 0.4609(14) 0.078(5) Uani 0.467(8) 1 d . . P . . Cl1 Cl 0.68687(5) 0.75631(5) 0.10214(4) 0.02641(13) Uani 1 1 d . . . . . O11 O 0.7752(2) 0.6753(2) 0.05428(17) 0.0552(6) Uani 1 1 d . . . . . O12 O 0.75409(19) 0.78648(19) 0.17065(15) 0.0450(5) Uani 1 1 d . . . . . O13 O 0.5879(2) 0.7132(2) 0.14799(19) 0.0598(7) Uani 1 1 d . . . . . O14 O 0.6302(3) 0.8497(2) 0.03540(18) 0.0633(7) Uani 1 1 d . . . . . O1A O 1.0460(2) 0.21460(16) 0.40274(13) 0.0385(4) Uani 1 1 d . . . . . N1A N 1.0276(4) 0.1723(5) 0.5582(3) 0.0267(10) Uani 0.519(6) 1 d . . P A 1 C1A C 1.0658(5) 0.2304(4) 0.4814(4) 0.0281(12) Uani 0.519(6) 1 d . . P A 1 H1G H 1.1073 0.2827 0.4876 0.034 Uiso 0.519(6) 1 calc R U P A 1 C2A C 0.9731(5) 0.0838(4) 0.5510(4) 0.0339(13) Uani 0.519(6) 1 d . . P A 1 H2A' H 0.9782 0.0721 0.4861 0.051 Uiso 0.519(6) 1 calc R U P A 1 H2B' H 0.8842 0.1026 0.5728 0.051 Uiso 0.519(6) 1 calc R U P A 1 H2C' H 1.0207 0.0181 0.5894 0.051 Uiso 0.519(6) 1 calc R U P A 1 C3A C 1.0060(14) 0.2031(9) 0.6562(8) 0.050(4) Uani 0.519(6) 1 d . . P A 1 H3A' H 1.0555 0.1441 0.7003 0.076 Uiso 0.519(6) 1 calc R U P A 1 H3B' H 0.9158 0.2173 0.6740 0.076 Uiso 0.519(6) 1 calc R U P A 1 H3C' H 1.0329 0.2677 0.6569 0.076 Uiso 0.519(6) 1 calc R U P A 1 N1A' N 1.0359(4) 0.2291(5) 0.5616(3) 0.0255(11) Uani 0.481(6) 1 d . . P A 2 C1A' C 1.0020(5) 0.1921(4) 0.4909(5) 0.0313(14) Uani 0.481(6) 1 d . . P A 2 H1G' H 0.9454 0.1489 0.5026 0.038 Uiso 0.481(6) 1 calc R U P A 2 C2A' C 1.1122(5) 0.3065(5) 0.5439(4) 0.0346(14) Uani 0.481(6) 1 d . . P A 2 H2D' H 1.1529 0.3041 0.4819 0.052 Uiso 0.481(6) 1 calc R U P A 2 H2E' H 1.1774 0.2876 0.5907 0.052 Uiso 0.481(6) 1 calc R U P A 2 H2F' H 1.0571 0.3790 0.5475 0.052 Uiso 0.481(6) 1 calc R U P A 2 C3A' C 1.0164(19) 0.2002(12) 0.6543(12) 0.081(7) Uani 0.481(6) 1 d . . P A 2 H3D' H 0.9742 0.1431 0.6639 0.122 Uiso 0.481(6) 1 calc R U P A 2 H3E' H 0.9631 0.2624 0.6810 0.122 Uiso 0.481(6) 1 calc R U P A 2 H3F' H 1.0981 0.1742 0.6849 0.122 Uiso 0.481(6) 1 calc R U P A 2 O1B O 0.75476(18) 0.27385(15) 0.14181(13) 0.0335(4) Uani 1 1 d . . . . . N1B N 0.6304(2) 0.16585(19) 0.12114(16) 0.0326(5) Uani 1 1 d . . . . . C1B C 0.7408(3) 0.1898(2) 0.12195(18) 0.0319(5) Uani 1 1 d . . . . . H1D H 0.8152 0.1374 0.1058 0.038 Uiso 1 1 calc R U . . . C2B C 0.5093(3) 0.2421(3) 0.1432(2) 0.0432(7) Uani 1 1 d . . . . . H2C H 0.5251 0.3070 0.1581 0.065 Uiso 1 1 calc R U . . . H2D H 0.4674 0.2091 0.1968 0.065 Uiso 1 1 calc R U . . . H2E H 0.4548 0.2611 0.0895 0.065 Uiso 1 1 calc R U . . . C3B C 0.6252(3) 0.0619(2) 0.0995(2) 0.0416(7) Uani 1 1 d . . . . . H3F H 0.7110 0.0185 0.0855 0.062 Uiso 1 1 calc R U . . . H3G H 0.5725 0.0740 0.0455 0.062 Uiso 1 1 calc R U . . . H3H H 0.5885 0.0241 0.1531 0.062 Uiso 1 1 calc R U . . . 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 Cu1 0.02295(14) 0.01866(14) 0.02193(15) -0.00118(10) 0.00048(10) -0.00611(11) O2 0.0269(8) 0.0251(8) 0.0320(9) -0.0055(7) -0.0011(7) -0.0078(7) O3 0.0378(10) 0.0250(9) 0.0384(10) -0.0025(8) -0.0070(8) -0.0133(8) N1 0.0295(10) 0.0201(9) 0.0232(10) -0.0024(7) 0.0007(8) -0.0084(8) N2 0.0269(10) 0.0224(10) 0.0281(10) -0.0032(8) 0.0030(8) -0.0079(8) N3 0.0251(9) 0.0234(10) 0.0203(9) 0.0000(7) -0.0024(7) -0.0080(8) N4 0.0244(9) 0.0249(10) 0.0231(10) -0.0025(8) 0.0012(8) -0.0078(8) N5 0.0265(10) 0.0226(10) 0.0244(10) -0.0042(8) 0.0010(8) -0.0057(8) N6 0.0233(9) 0.0268(10) 0.0258(10) -0.0066(8) 0.0006(8) -0.0055(8) N7 0.0269(10) 0.0216(9) 0.0249(10) -0.0033(8) 0.0009(8) -0.0079(8) N8 0.0270(9) 0.0194(9) 0.0226(10) -0.0009(7) 0.0012(8) -0.0077(8) C1 0.0358(13) 0.0245(12) 0.0367(14) -0.0059(10) 0.0077(11) -0.0128(11) C2 0.0317(12) 0.0260(12) 0.0297(12) -0.0043(10) 0.0020(10) -0.0138(10) C3 0.0328(12) 0.0354(14) 0.0230(12) 0.0041(10) -0.0019(10) -0.0118(11) C4 0.0224(11) 0.0312(13) 0.0288(12) -0.0038(10) -0.0010(9) -0.0083(10) C5 0.0238(11) 0.0298(12) 0.0254(12) -0.0017(9) -0.0020(9) -0.0080(10) C6 0.0233(11) 0.0316(13) 0.0307(13) -0.0072(10) 0.0013(9) -0.0084(10) C7 0.0268(11) 0.0257(12) 0.0230(11) -0.0053(9) -0.0013(9) -0.0061(9) C8 0.0225(10) 0.0286(12) 0.0245(11) -0.0042(9) -0.0017(9) -0.0076(9) C9 0.0232(11) 0.0286(12) 0.0280(12) -0.0051(10) -0.0021(9) -0.0062(9) C10 0.0302(12) 0.0241(11) 0.0208(11) -0.0016(9) -0.0017(9) -0.0080(10) C11 0.0326(13) 0.0238(12) 0.0478(16) -0.0074(11) -0.0048(12) -0.0039(10) C12 0.0244(11) 0.0357(13) 0.0273(12) -0.0080(10) 0.0012(9) -0.0121(10) C13 0.0201(10) 0.0326(13) 0.0291(12) -0.0072(10) -0.0006(9) -0.0044(9) C14 0.0340(13) 0.0242(12) 0.0361(14) -0.0078(10) 0.0055(11) -0.0118(10) C15 0.0319(13) 0.0241(12) 0.0383(14) -0.0015(10) -0.0015(11) -0.0038(10) C16 0.0329(12) 0.0258(12) 0.0301(13) -0.0077(10) 0.0064(10) -0.0115(10) C17 0.0294(11) 0.0236(11) 0.0247(11) -0.0033(9) 0.0016(9) -0.0085(9) C18 0.0287(11) 0.0215(11) 0.0247(11) -0.0042(9) 0.0028(9) -0.0070(9) C19 0.0283(11) 0.0210(11) 0.0215(11) 0.0014(9) -0.0008(9) -0.0098(9) C20 0.0296(12) 0.0253(12) 0.0329(13) -0.0028(10) 0.0022(10) -0.0087(10) C21 0.0362(13) 0.0202(11) 0.0310(13) -0.0022(9) 0.0014(10) -0.0098(10) C22 0.0351(12) 0.0230(11) 0.0241(12) 0.0016(9) -0.0047(10) -0.0121(10) C23 0.0437(14) 0.0254(12) 0.0332(14) -0.0043(10) -0.0054(11) -0.0154(11) C24 0.0295(12) 0.0268(12) 0.0301(13) 0.0008(10) -0.0047(10) -0.0076(10) C25 0.0303(12) 0.0226(11) 0.0275(12) -0.0001(9) -0.0036(10) -0.0073(10) Cl2 0.0246(3) 0.0278(3) 0.0511(4) -0.0131(3) -0.0078(3) -0.0070(2) O21 0.0247(9) 0.0439(12) 0.0566(13) -0.0147(10) -0.0064(9) -0.0003(8) O22 0.036(2) 0.028(2) 0.134(7) -0.005(3) 0.013(3) -0.0149(18) O23 0.038(2) 0.154(8) 0.035(3) -0.039(4) 0.0055(19) -0.013(3) O24 0.026(3) 0.050(4) 0.061(6) -0.020(3) -0.015(3) -0.008(3) O2A 0.023(2) 0.024(2) 0.060(4) -0.019(2) -0.004(2) -0.0052(15) O2B 0.084(5) 0.038(3) 0.094(5) -0.010(3) 0.049(4) -0.025(3) O2C 0.060(8) 0.089(11) 0.070(9) -0.057(8) -0.041(6) 0.037(6) Cl1 0.0208(2) 0.0286(3) 0.0291(3) 0.0000(2) -0.0020(2) -0.0080(2) O11 0.0374(11) 0.0749(17) 0.0579(15) -0.0385(13) 0.0010(10) -0.0078(11) O12 0.0340(10) 0.0541(13) 0.0473(12) -0.0229(10) -0.0124(9) -0.0015(9) O13 0.0421(12) 0.0659(16) 0.0770(18) -0.0038(13) 0.0178(12) -0.0330(12) O14 0.0929(19) 0.0442(13) 0.0542(15) 0.0188(11) -0.0330(14) -0.0279(13) O1A 0.0510(12) 0.0385(11) 0.0268(10) -0.0028(8) -0.0078(8) -0.0131(9) N1A 0.027(2) 0.031(3) 0.021(2) -0.003(2) -0.0011(16) -0.008(2) C1A 0.027(2) 0.025(2) 0.035(3) -0.0031(19) -0.005(2) -0.010(2) C2A 0.035(3) 0.031(3) 0.035(3) 0.007(2) -0.008(2) -0.014(2) C3A 0.095(8) 0.042(7) 0.026(6) 0.014(4) -0.024(5) -0.043(7) N1A' 0.026(2) 0.029(3) 0.020(2) -0.005(2) 0.0006(16) -0.007(2) C1A' 0.032(3) 0.019(2) 0.044(4) -0.002(2) -0.006(2) -0.010(2) C2A' 0.035(3) 0.043(3) 0.032(3) -0.005(2) -0.001(2) -0.021(3) C3A' 0.131(13) 0.046(8) 0.036(9) -0.020(6) -0.004(7) 0.031(7) O1B 0.0389(10) 0.0321(10) 0.0302(10) -0.0014(8) -0.0028(8) -0.0124(8) N1B 0.0308(11) 0.0321(12) 0.0320(12) 0.0010(9) -0.0056(9) -0.0065(9) C1B 0.0319(13) 0.0331(14) 0.0288(13) -0.0021(10) -0.0053(10) -0.0066(11) C2B 0.0307(13) 0.0466(17) 0.0491(18) -0.0076(14) -0.0041(12) -0.0049(13) C3B 0.0468(16) 0.0355(15) 0.0420(16) 0.0010(12) -0.0127(13) -0.0118(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 Cu1 N4 1.986(2) . ? Cu1 N1 2.002(2) . ? Cu1 N3 2.051(2) . ? Cu1 N2 2.066(2) . ? Cu1 O1A 2.367(2) . ? O2 C10 1.358(3) . ? O2 C11 1.424(3) . ? O3 C22 1.356(3) . ? O3 C23 1.436(3) . ? N1 N7 1.309(3) . ? N1 C17 1.347(3) . ? N2 C15 1.481(3) . ? N2 C14 1.484(3) . ? N2 C16 1.490(3) . ? N3 C3 1.478(3) . ? N3 C2 1.482(3) . ? N3 C4 1.489(3) . ? N4 N5 1.310(3) . ? N4 C5 1.355(3) . ? N5 N6 1.337(3) . ? N6 C6 1.358(3) . ? N6 C7 1.425(3) . ? N7 N8 1.341(3) . ? N8 C18 1.348(3) . ? N8 C19 1.434(3) . ? C1 C2 1.506(4) . ? C1 C14 1.512(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.478(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.359(3) . ? C6 H6 0.9300 . ? C7 C8 1.374(3) . ? C7 C13 1.387(3) . ? C8 C9 1.382(3) . ? C8 H8 0.9300 . ? C9 C10 1.388(3) . ? C9 H9 0.9300 . ? C10 C12 1.392(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.367(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.479(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.358(3) . ? C18 H18 0.9300 . ? C19 C20 1.370(3) . ? C19 C25 1.388(3) . ? C20 C21 1.384(3) . ? C20 H20 0.9300 . ? C21 C22 1.384(4) . ? C21 H21 0.9300 . ? C22 C24 1.396(4) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.381(3) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? Cl2 O23 1.327(5) . ? Cl2 O24 1.390(14) . ? Cl2 O2C 1.393(19) . ? Cl2 O21 1.415(2) . ? Cl2 O2A 1.420(4) . ? Cl2 O22 1.497(5) . ? Cl2 O2B 1.536(6) . ? O22 O2A 1.174(7) . ? O23 O2B 0.972(8) . ? O23 O2A 1.443(9) . ? Cl1 O13 1.413(2) . ? Cl1 O14 1.421(2) . ? Cl1 O11 1.425(2) . ? Cl1 O12 1.428(2) . ? O1A C1A 1.221(5) . ? O1A C1A' 1.328(7) . ? N1A C1A 1.331(7) . ? N1A C2A 1.449(8) . ? N1A C3A 1.502(13) . ? C1A H1G 0.9300 . ? C2A H2A' 0.9600 . ? C2A H2B' 0.9600 . ? C2A H2C' 0.9600 . ? C3A H3A' 0.9600 . ? C3A H3B' 0.9600 . ? C3A H3C' 0.9600 . ? N1A' C1A' 1.305(8) . ? N1A' C3A' 1.333(17) . ? N1A' C2A' 1.449(8) . ? C1A' H1G' 0.9300 . ? C2A' H2D' 0.9600 . ? C2A' H2E' 0.9600 . ? C2A' H2F' 0.9600 . ? C3A' H3D' 0.9600 . ? C3A' H3E' 0.9600 . ? C3A' H3F' 0.9600 . ? O1B C1B 1.218(3) . ? N1B C1B 1.317(3) . ? N1B C2B 1.440(4) . ? N1B C3B 1.442(4) . ? C1B H1D 0.9300 . ? C2B H2C 0.9600 . ? C2B H2D 0.9600 . ? C2B H2E 0.9600 . ? C3B H3F 0.9600 . ? C3B H3G 0.9600 . ? C3B H3H 0.9600 . ? 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 N4 Cu1 N1 99.48(8) . . ? N4 Cu1 N3 82.15(8) . . ? N1 Cu1 N3 177.61(8) . . ? N4 Cu1 N2 177.51(8) . . ? N1 Cu1 N2 82.48(8) . . ? N3 Cu1 N2 95.84(8) . . ? N4 Cu1 O1A 86.58(8) . . ? N1 Cu1 O1A 93.47(8) . . ? N3 Cu1 O1A 88.37(8) . . ? N2 Cu1 O1A 94.86(8) . . ? C10 O2 C11 116.94(19) . . ? C22 O3 C23 117.4(2) . . ? N7 N1 C17 110.93(19) . . ? N7 N1 Cu1 133.07(16) . . ? C17 N1 Cu1 112.45(16) . . ? C15 N2 C14 109.6(2) . . ? C15 N2 C16 107.31(19) . . ? C14 N2 C16 108.38(19) . . ? C15 N2 Cu1 110.52(16) . . ? C14 N2 Cu1 114.77(15) . . ? C16 N2 Cu1 105.95(14) . . ? C3 N3 C2 110.32(19) . . ? C3 N3 C4 107.95(19) . . ? C2 N3 C4 107.10(18) . . ? C3 N3 Cu1 108.99(15) . . ? C2 N3 Cu1 114.91(15) . . ? C4 N3 Cu1 107.31(14) . . ? N5 N4 C5 111.1(2) . . ? N5 N4 Cu1 135.04(16) . . ? C5 N4 Cu1 113.60(16) . . ? N4 N5 N6 105.29(18) . . ? N5 N6 C6 111.7(2) . . ? N5 N6 C7 119.30(19) . . ? C6 N6 C7 129.0(2) . . ? N1 N7 N8 105.30(18) . . ? N7 N8 C18 111.50(19) . . ? N7 N8 C19 120.04(19) . . ? C18 N8 C19 128.3(2) . . ? C2 C1 C14 113.2(2) . . ? C2 C1 H1A 108.9 . . ? C14 C1 H1A 108.9 . . ? C2 C1 H1B 108.9 . . ? C14 C1 H1B 108.9 . . ? H1A C1 H1B 107.8 . . ? N3 C2 C1 114.7(2) . . ? N3 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? N3 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? N3 C3 H3A 109.5 . . ? N3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 N3 108.24(19) . . ? C5 C4 H4A 110.1 . . ? N3 C4 H4A 110.1 . . ? C5 C4 H4B 110.1 . . ? N3 C4 H4B 110.1 . . ? H4A C4 H4B 108.4 . . ? N4 C5 C6 107.2(2) . . ? N4 C5 C4 116.9(2) . . ? C6 C5 C4 135.8(2) . . ? N6 C6 C5 104.7(2) . . ? N6 C6 H6 127.7 . . ? C5 C6 H6 127.7 . . ? C8 C7 C13 121.0(2) . . ? C8 C7 N6 119.2(2) . . ? C13 C7 N6 119.7(2) . . ? C7 C8 C9 119.5(2) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C8 C9 C10 119.8(2) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? O2 C10 C9 124.4(2) . . ? O2 C10 C12 115.4(2) . . ? C9 C10 C12 120.1(2) . . ? O2 C11 H11A 109.5 . . ? O2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C10 119.8(2) . . ? C13 C12 H12 120.1 . . ? C10 C12 H12 120.1 . . ? C12 C13 C7 119.8(2) . . ? C12 C13 H13 120.1 . . ? C7 C13 H13 120.1 . . ? N2 C14 C1 114.3(2) . . ? N2 C14 H14A 108.7 . . ? C1 C14 H14A 108.7 . . ? N2 C14 H14B 108.7 . . ? C1 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? N2 C15 H15A 109.5 . . ? N2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 N2 107.3(2) . . ? C17 C16 H16A 110.3 . . ? N2 C16 H16A 110.3 . . ? C17 C16 H16B 110.3 . . ? N2 C16 H16B 110.3 . . ? H16A C16 H16B 108.5 . . ? N1 C17 C18 107.4(2) . . ? N1 C17 C16 116.6(2) . . ? C18 C17 C16 135.9(2) . . ? N8 C18 C17 104.8(2) . . ? N8 C18 H18 127.6 . . ? C17 C18 H18 127.6 . . ? C20 C19 C25 121.2(2) . . ? C20 C19 N8 119.7(2) . . ? C25 C19 N8 119.1(2) . . ? C19 C20 C21 119.8(2) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 120.1(2) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? O3 C22 C21 125.0(2) . . ? O3 C22 C24 115.4(2) . . ? C21 C22 C24 119.6(2) . . ? O3 C23 H23A 109.5 . . ? O3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C22 120.3(2) . . ? C25 C24 H24 119.9 . . ? C22 C24 H24 119.9 . . ? C24 C25 C19 119.0(2) . . ? C24 C25 H25 120.5 . . ? C19 C25 H25 120.5 . . ? O23 Cl2 O24 113.3(7) . . ? O23 Cl2 O2C 123.8(8) . . ? O24 Cl2 O2C 17.0(12) . . ? O23 Cl2 O21 115.8(3) . . ? O24 Cl2 O21 112.3(7) . . ? O2C Cl2 O21 112.8(8) . . ? O23 Cl2 O2A 63.3(4) . . ? O24 Cl2 O2A 124.9(7) . . ? O2C Cl2 O2A 115.0(8) . . ? O21 Cl2 O2A 117.56(18) . . ? O23 Cl2 O22 110.6(4) . . ? O24 Cl2 O22 104.4(6) . . ? O2C Cl2 O22 87.7(8) . . ? O21 Cl2 O22 98.8(2) . . ? O2A Cl2 O22 47.4(3) . . ? O23 Cl2 O2B 38.8(4) . . ? O24 Cl2 O2B 88.6(7) . . ? O2C Cl2 O2B 104.8(8) . . ? O21 Cl2 O2B 102.3(3) . . ? O2A Cl2 O2B 101.9(3) . . ? O22 Cl2 O2B 148.7(3) . . ? O2A O22 Cl2 62.9(3) . . ? O2B O23 Cl2 82.3(6) . . ? O2B O23 O2A 143.3(7) . . ? Cl2 O23 O2A 61.5(3) . . ? O22 O2A Cl2 69.8(3) . . ? O22 O2A O23 124.9(4) . . ? Cl2 O2A O23 55.2(3) . . ? O23 O2B Cl2 58.9(4) . . ? O13 Cl1 O14 108.80(16) . . ? O13 Cl1 O11 109.22(16) . . ? O14 Cl1 O11 109.70(17) . . ? O13 Cl1 O12 109.74(16) . . ? O14 Cl1 O12 109.96(15) . . ? O11 Cl1 O12 109.41(13) . . ? C1A O1A Cu1 146.6(3) . . ? C1A' O1A Cu1 120.0(3) . . ? C1A N1A C2A 121.5(5) . . ? C1A N1A C3A 125.9(6) . . ? C2A N1A C3A 111.1(5) . . ? O1A C1A N1A 119.6(5) . . ? O1A C1A H1G 120.2 . . ? N1A C1A H1G 120.2 . . ? N1A C2A H2A' 109.5 . . ? N1A C2A H2B' 109.5 . . ? H2A' C2A H2B' 109.5 . . ? N1A C2A H2C' 109.5 . . ? H2A' C2A H2C' 109.5 . . ? H2B' C2A H2C' 109.5 . . ? N1A C3A H3A' 109.5 . . ? N1A C3A H3B' 109.5 . . ? H3A' C3A H3B' 109.5 . . ? N1A C3A H3C' 109.5 . . ? H3A' C3A H3C' 109.5 . . ? H3B' C3A H3C' 109.5 . . ? C1A' N1A' C3A' 128.4(10) . . ? C1A' N1A' C2A' 120.1(5) . . ? C3A' N1A' C2A' 111.5(10) . . ? N1A' C1A' O1A 121.9(5) . . ? N1A' C1A' H1G' 119.1 . . ? O1A C1A' H1G' 119.1 . . ? N1A' C2A' H2D' 109.5 . . ? N1A' C2A' H2E' 109.5 . . ? H2D' C2A' H2E' 109.5 . . ? N1A' C2A' H2F' 109.5 . . ? H2D' C2A' H2F' 109.5 . . ? H2E' C2A' H2F' 109.5 . . ? N1A' C3A' H3D' 109.5 . . ? N1A' C3A' H3E' 109.5 . . ? H3D' C3A' H3E' 109.5 . . ? N1A' C3A' H3F' 109.5 . . ? H3D' C3A' H3F' 109.5 . . ? H3E' C3A' H3F' 109.5 . . ? C1B N1B C2B 121.3(2) . . ? C1B N1B C3B 121.7(2) . . ? C2B N1B C3B 117.0(2) . . ? O1B C1B N1B 126.3(3) . . ? O1B C1B H1D 116.9 . . ? N1B C1B H1D 116.9 . . ? N1B C2B H2C 109.5 . . ? N1B C2B H2D 109.5 . . ? H2C C2B H2D 109.5 . . ? N1B C2B H2E 109.5 . . ? H2C C2B H2E 109.5 . . ? H2D C2B H2E 109.5 . . ? N1B C3B H3F 109.5 . . ? N1B C3B H3G 109.5 . . ? H3F C3B H3G 109.5 . . ? N1B C3B H3H 109.5 . . ? H3F C3B H3H 109.5 . . ? H3G C3B H3H 109.5 . . ? 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 C5 N4 N5 N6 -0.7(2) . . . . ? Cu1 N4 N5 N6 172.89(17) . . . . ? N4 N5 N6 C6 0.3(3) . . . . ? N4 N5 N6 C7 178.92(19) . . . . ? C17 N1 N7 N8 -0.5(2) . . . . ? Cu1 N1 N7 N8 -157.05(17) . . . . ? N1 N7 N8 C18 0.6(2) . . . . ? N1 N7 N8 C19 176.73(19) . . . . ? C3 N3 C2 C1 68.1(3) . . . . ? C4 N3 C2 C1 -174.6(2) . . . . ? Cu1 N3 C2 C1 -55.6(2) . . . . ? C14 C1 C2 N3 70.8(3) . . . . ? C3 N3 C4 C5 -81.1(2) . . . . ? C2 N3 C4 C5 160.11(19) . . . . ? Cu1 N3 C4 C5 36.2(2) . . . . ? N5 N4 C5 C6 0.7(3) . . . . ? Cu1 N4 C5 C6 -174.30(16) . . . . ? N5 N4 C5 C4 -177.5(2) . . . . ? Cu1 N4 C5 C4 7.5(3) . . . . ? N3 C4 C5 N4 -29.9(3) . . . . ? N3 C4 C5 C6 152.5(3) . . . . ? N5 N6 C6 C5 0.1(3) . . . . ? C7 N6 C6 C5 -178.3(2) . . . . ? N4 C5 C6 N6 -0.5(3) . . . . ? C4 C5 C6 N6 177.3(3) . . . . ? N5 N6 C7 C8 -145.5(2) . . . . ? C6 N6 C7 C8 32.8(4) . . . . ? N5 N6 C7 C13 32.2(3) . . . . ? C6 N6 C7 C13 -149.4(3) . . . . ? C13 C7 C8 C9 0.2(4) . . . . ? N6 C7 C8 C9 177.9(2) . . . . ? C7 C8 C9 C10 -0.7(4) . . . . ? C11 O2 C10 C9 -8.1(3) . . . . ? C11 O2 C10 C12 172.2(2) . . . . ? C8 C9 C10 O2 -179.6(2) . . . . ? C8 C9 C10 C12 0.1(4) . . . . ? O2 C10 C12 C13 -179.1(2) . . . . ? C9 C10 C12 C13 1.2(4) . . . . ? C10 C12 C13 C7 -1.6(4) . . . . ? C8 C7 C13 C12 1.0(4) . . . . ? N6 C7 C13 C12 -176.7(2) . . . . ? C15 N2 C14 C1 -69.7(3) . . . . ? C16 N2 C14 C1 173.5(2) . . . . ? Cu1 N2 C14 C1 55.3(3) . . . . ? C2 C1 C14 N2 -70.6(3) . . . . ? C15 N2 C16 C17 78.1(2) . . . . ? C14 N2 C16 C17 -163.6(2) . . . . ? Cu1 N2 C16 C17 -40.0(2) . . . . ? N7 N1 C17 C18 0.3(3) . . . . ? Cu1 N1 C17 C18 161.98(16) . . . . ? N7 N1 C17 C16 -178.2(2) . . . . ? Cu1 N1 C17 C16 -16.6(3) . . . . ? N2 C16 C17 N1 39.0(3) . . . . ? N2 C16 C17 C18 -139.1(3) . . . . ? N7 N8 C18 C17 -0.3(3) . . . . ? C19 N8 C18 C17 -176.1(2) . . . . ? N1 C17 C18 N8 0.0(3) . . . . ? C16 C17 C18 N8 178.2(3) . . . . ? N7 N8 C19 C20 25.1(3) . . . . ? C18 N8 C19 C20 -159.5(2) . . . . ? N7 N8 C19 C25 -152.6(2) . . . . ? C18 N8 C19 C25 22.9(3) . . . . ? C25 C19 C20 C21 -0.2(4) . . . . ? N8 C19 C20 C21 -177.8(2) . . . . ? C19 C20 C21 C22 -1.0(4) . . . . ? C23 O3 C22 C21 5.5(4) . . . . ? C23 O3 C22 C24 -174.8(2) . . . . ? C20 C21 C22 O3 -178.8(2) . . . . ? C20 C21 C22 C24 1.4(4) . . . . ? O3 C22 C24 C25 179.6(2) . . . . ? C21 C22 C24 C25 -0.6(4) . . . . ? C22 C24 C25 C19 -0.6(4) . . . . ? C20 C19 C25 C24 1.1(4) . . . . ? N8 C19 C25 C24 178.7(2) . . . . ? O23 Cl2 O22 O2A -2.3(4) . . . . ? O24 Cl2 O22 O2A -124.5(8) . . . . ? O2C Cl2 O22 O2A -127.7(8) . . . . ? O21 Cl2 O22 O2A 119.6(3) . . . . ? O2B Cl2 O22 O2A -12.5(8) . . . . ? O24 Cl2 O23 O2B -54.7(10) . . . . ? O2C Cl2 O23 O2B -70.0(11) . . . . ? O21 Cl2 O23 O2B 77.2(6) . . . . ? O2A Cl2 O23 O2B -173.4(7) . . . . ? O22 Cl2 O23 O2B -171.5(6) . . . . ? O24 Cl2 O23 O2A 118.8(7) . . . . ? O2C Cl2 O23 O2A 103.4(9) . . . . ? O21 Cl2 O23 O2A -109.4(3) . . . . ? O22 Cl2 O23 O2A 1.9(3) . . . . ? O2B Cl2 O23 O2A 173.4(7) . . . . ? Cl2 O22 O2A O23 2.4(4) . . . . ? O23 Cl2 O2A O22 177.6(4) . . . . ? O24 Cl2 O2A O22 76.7(8) . . . . ? O2C Cl2 O2A O22 60.7(9) . . . . ? O21 Cl2 O2A O22 -75.7(3) . . . . ? O2B Cl2 O2A O22 173.4(4) . . . . ? O24 Cl2 O2A O23 -100.9(8) . . . . ? O2C Cl2 O2A O23 -116.9(9) . . . . ? O21 Cl2 O2A O23 106.7(3) . . . . ? O22 Cl2 O2A O23 -177.6(4) . . . . ? O2B Cl2 O2A O23 -4.2(5) . . . . ? O2B O23 O2A O22 8.2(15) . . . . ? Cl2 O23 O2A O22 -2.8(5) . . . . ? O2B O23 O2A Cl2 10.9(12) . . . . ? O2A O23 O2B Cl2 -9.7(11) . . . . ? O24 Cl2 O2B O23 131.5(9) . . . . ? O2C Cl2 O2B O23 126.1(10) . . . . ? O21 Cl2 O2B O23 -116.0(6) . . . . ? O2A Cl2 O2B O23 6.0(7) . . . . ? O22 Cl2 O2B O23 15.4(12) . . . . ? C1A' O1A C1A N1A 17.1(4) . . . . ? Cu1 O1A C1A N1A 90.7(6) . . . . ? C2A N1A C1A O1A 5.5(7) . . . . ? C3A N1A C1A O1A -159.7(8) . . . . ? C3A' N1A' C1A' O1A -168.5(10) . . . . ? C2A' N1A' C1A' O1A 6.9(8) . . . . ? C1A O1A C1A' N1A' 5.9(5) . . . . ? Cu1 O1A C1A' N1A' -136.5(4) . . . . ? C2B N1B C1B O1B 1.2(4) . . . . ? C3B N1B C1B O1B -177.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.479 _refine_diff_density_min -0.627 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 851239' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_[CuL5(MeCN)](ClO4)2 _audit_creation_date 2011-03-21T16:48:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_name_common '[CuL5(MeCN)](ClO4)2' _chemical_formula_moiety 'C26 H33 Cl Cu1 N9 O4, Cl O4' _chemical_formula_sum 'C26 H33 Cl2 Cu1 N9 O8' _chemical_formula_weight 734.06 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _symmetry_cell_setting triclinic _cell_length_a 10.573(4) _cell_length_b 10.596(4) _cell_length_c 16.788(5) _cell_angle_alpha 73.602(4) _cell_angle_beta 79.087(5) _cell_angle_gamma 60.693(3) _cell_volume 1570.4(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 15208 _cell_measurement_theta_min 3.2551 _cell_measurement_theta_max 28.2193 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.552 _exptl_crystal_F_000 758 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.929 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.64179 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 10.4508 _diffrn_orient_matrix_ub_11 -0.0433698 _diffrn_orient_matrix_ub_12 0.0597136 _diffrn_orient_matrix_ub_13 -0.0310857 _diffrn_orient_matrix_ub_21 -0.0561059 _diffrn_orient_matrix_ub_22 0.027275 _diffrn_orient_matrix_ub_23 0.0307945 _diffrn_orient_matrix_ub_31 0.0301941 _diffrn_orient_matrix_ub_32 0.0434374 _diffrn_orient_matrix_ub_33 0.0056873 _diffrn_measurement_device 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0711 _diffrn_reflns_av_unetI/netI 0.0373 _diffrn_reflns_number 64933 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 28.28 _reflns_number_total 7198 _reflns_number_gt 6140 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0304P)^2^+1.5886P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7198 _refine_ls_number_parameters 418 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0854 _refine_ls_wR_factor_gt 0.0795 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 Cu1 Cu 0.55144(2) 0.50819(3) 0.191375(15) 0.01244(7) Uani 1 1 d . . . Cl1 Cl 0.12772(5) 0.15599(5) -0.00187(3) 0.01705(11) Uani 1 1 d . . . Cl2 Cl 0.17724(5) 0.69561(5) 0.34982(3) 0.01625(11) Uani 1 1 d . . . O13 O 0.12243(17) 0.09698(17) 0.08651(10) 0.0239(3) Uani 1 1 d . . . O22 O 0.24230(18) 0.75292(18) 0.38909(10) 0.0270(4) Uani 1 1 d . . . O14 O 0.26335(17) 0.05591(18) -0.03844(10) 0.0275(4) Uani 1 1 d . . . O23 O 0.28972(17) 0.59106(19) 0.30431(11) 0.0279(4) Uani 1 1 d . . . N4 N 0.41779(18) 0.45175(18) 0.16217(10) 0.0137(3) Uani 1 1 d . . . O12 O 0.12067(18) 0.29991(18) -0.01846(10) 0.0278(4) Uani 1 1 d . . . N6 N 0.40700(18) 0.32796(19) 0.18093(11) 0.0157(3) Uani 1 1 d . . . N9 N 0.64213(18) 0.24478(19) 0.42470(10) 0.0151(3) Uani 1 1 d . . . O11 O 0.00826(17) 0.16722(18) -0.03731(10) 0.0258(4) Uani 1 1 d . . . O21 O 0.07479(18) 0.81592(19) 0.29297(11) 0.0315(4) Uani 1 1 d . . . N8 N 0.62315(18) 0.25133(18) 0.34682(10) 0.0152(3) Uani 1 1 d . . . N3 N 0.43698(17) 0.70113(18) 0.10972(10) 0.0129(3) Uani 1 1 d . . . N1 N 0.60455(17) 0.38403(18) 0.30478(10) 0.0140(3) Uani 1 1 d . . . N2 N 0.63828(18) 0.61828(18) 0.22517(10) 0.0143(3) Uani 1 1 d . . . C7 C 0.1499(2) 0.2467(2) 0.25669(13) 0.0162(4) Uani 1 1 d . . . N7 N 0.28106(18) 0.36589(19) 0.15211(11) 0.0154(3) Uani 1 1 d . . . N5 N 0.7402(2) 0.3563(2) 0.12005(12) 0.0237(4) Uani 1 1 d . . . C24 C 0.3831(2) 0.2474(2) 0.51469(13) 0.0176(4) Uani 1 1 d . . . H24 H 0.3760 0.3159 0.4629 0.021 Uiso 1 1 calc R . . C20 C 0.5270(2) 0.0342(2) 0.61690(13) 0.0181(4) Uani 1 1 d . . . H20 H 0.6192 -0.0425 0.6353 0.022 Uiso 1 1 calc R . . O24 O 0.1072(2) 0.6227(2) 0.41182(11) 0.0351(4) Uani 1 1 d . . . C11 C 0.0254(2) 0.1290(2) 0.36004(14) 0.0219(5) Uani 1 1 d . . . H11 H -0.0102 0.0581 0.3773 0.026 Uiso 1 1 calc R . . C19 C 0.5184(2) 0.1356(2) 0.54096(13) 0.0155(4) Uani 1 1 d . . . C4 C 0.3006(2) 0.5672(2) 0.12227(12) 0.0148(4) Uani 1 1 d . . . C17 C 0.6362(2) 0.3712(2) 0.43251(13) 0.0160(4) Uani 1 1 d . . . H17 H 0.6468 0.3929 0.4813 0.019 Uiso 1 1 calc R . . C3 C 0.2897(2) 0.7187(2) 0.10327(13) 0.0164(4) Uani 1 1 d . . . H3A H 0.2567 0.7724 0.0465 0.020 Uiso 1 1 calc R . . H3B H 0.2188 0.7763 0.1433 0.020 Uiso 1 1 calc R . . C5 C 0.2110(2) 0.5118(2) 0.11556(13) 0.0166(4) Uani 1 1 d . . . H5 H 0.1201 0.5641 0.0908 0.020 Uiso 1 1 calc R . . C1 C 0.4276(2) 0.8181(2) 0.14708(13) 0.0162(4) Uani 1 1 d . . . H1A H 0.3569 0.8309 0.1959 0.019 Uiso 1 1 calc R . . H1B H 0.3938 0.9140 0.1058 0.019 Uiso 1 1 calc R . . C8 C 0.1301(2) 0.3361(2) 0.30932(14) 0.0183(4) Uani 1 1 d . . . H8 H 0.1661 0.4067 0.2924 0.022 Uiso 1 1 calc R . . C12 C 0.0974(2) 0.1427(2) 0.28246(14) 0.0194(4) Uani 1 1 d . . . H12 H 0.1110 0.0812 0.2467 0.023 Uiso 1 1 calc R . . C22 C 0.2677(2) 0.1578(3) 0.63939(14) 0.0216(5) Uani 1 1 d . . . H22 H 0.1822 0.1658 0.6730 0.026 Uiso 1 1 calc R . . C15 C 0.5904(2) 0.6146(2) 0.31518(12) 0.0154(4) Uani 1 1 d . . . H15A H 0.6491 0.6390 0.3418 0.018 Uiso 1 1 calc R . . H15B H 0.4869 0.6875 0.3214 0.018 Uiso 1 1 calc R . . C13 C 0.5761(2) 0.7727(2) 0.17358(13) 0.0175(4) Uani 1 1 d . . . H13A H 0.6418 0.7786 0.1237 0.021 Uiso 1 1 calc R . . H13B H 0.5675 0.8416 0.2060 0.021 Uiso 1 1 calc R . . C10 C 0.0054(2) 0.2186(3) 0.41255(14) 0.0236(5) Uani 1 1 d . . . H10 H -0.0438 0.2091 0.4657 0.028 Uiso 1 1 calc R . . C9 C 0.0573(2) 0.3218(2) 0.38718(14) 0.0215(4) Uani 1 1 d . . . H9 H 0.0432 0.3833 0.4230 0.026 Uiso 1 1 calc R . . C6 C 0.2271(2) 0.2566(2) 0.17084(14) 0.0194(4) Uani 1 1 d . . . H6A H 0.3097 0.1580 0.1673 0.023 Uiso 1 1 calc R . . H6B H 0.1590 0.2837 0.1286 0.023 Uiso 1 1 calc R . . C21 C 0.4028(2) 0.0448(2) 0.66511(14) 0.0214(4) Uani 1 1 d . . . H21 H 0.4096 -0.0253 0.7161 0.026 Uiso 1 1 calc R . . C18 C 0.6586(2) 0.1134(2) 0.48985(13) 0.0170(4) Uani 1 1 d . . . H18A H 0.7335 0.0892 0.5270 0.020 Uiso 1 1 calc R . . H18B H 0.6927 0.0281 0.4639 0.020 Uiso 1 1 calc R . . C25 C 0.7881(2) 0.2308(3) 0.13574(13) 0.0210(4) Uani 1 1 d . . . C23 C 0.2581(2) 0.2591(2) 0.56426(14) 0.0203(4) Uani 1 1 d . . . H23 H 0.1658 0.3368 0.5467 0.024 Uiso 1 1 calc R . . C14 C 0.7992(2) 0.5471(2) 0.21619(14) 0.0200(4) Uani 1 1 d . . . H14A H 0.8316 0.5408 0.1581 0.030 Uiso 1 1 calc R . . H14B H 0.8389 0.4471 0.2519 0.030 Uiso 1 1 calc R . . H14C H 0.8335 0.6064 0.2326 0.030 Uiso 1 1 calc R . . C16 C 0.6117(2) 0.4610(2) 0.35447(12) 0.0140(4) Uani 1 1 d . . . C2 C 0.5154(2) 0.7012(2) 0.02659(13) 0.0196(4) Uani 1 1 d . . . H2A H 0.4656 0.7988 -0.0104 0.029 Uiso 1 1 calc R . . H2B H 0.5173 0.6251 0.0034 0.029 Uiso 1 1 calc R . . H2C H 0.6151 0.6798 0.0318 0.029 Uiso 1 1 calc R . . C26 C 0.8435(3) 0.0706(3) 0.15848(16) 0.0282(5) Uani 1 1 d . . . H26A H 0.8863 0.0315 0.2126 0.042 Uiso 1 1 calc R . . H26B H 0.9179 0.0257 0.1163 0.042 Uiso 1 1 calc R . . H26C H 0.7638 0.0468 0.1620 0.042 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 Cu1 0.01291(12) 0.01358(12) 0.01158(12) -0.00235(9) -0.00261(9) -0.00629(9) Cl1 0.0168(2) 0.0181(2) 0.0171(2) -0.00098(18) -0.00423(18) -0.00915(19) Cl2 0.0150(2) 0.0187(2) 0.0147(2) -0.00491(18) -0.00049(17) -0.00703(19) O13 0.0283(8) 0.0252(8) 0.0183(8) 0.0010(6) -0.0040(6) -0.0146(7) O22 0.0301(9) 0.0309(9) 0.0260(9) -0.0124(7) -0.0077(7) -0.0134(7) O14 0.0189(8) 0.0275(9) 0.0286(9) -0.0038(7) 0.0013(7) -0.0074(7) O23 0.0208(8) 0.0350(9) 0.0303(9) -0.0213(8) 0.0053(7) -0.0095(7) N4 0.0165(8) 0.0142(8) 0.0118(8) -0.0040(6) -0.0024(6) -0.0070(7) O12 0.0369(9) 0.0224(8) 0.0274(9) -0.0012(7) -0.0048(7) -0.0176(7) N6 0.0178(8) 0.0170(8) 0.0156(8) -0.0053(7) -0.0022(7) -0.0092(7) N9 0.0158(8) 0.0174(8) 0.0115(8) -0.0023(7) -0.0014(6) -0.0075(7) O11 0.0218(8) 0.0274(8) 0.0298(9) -0.0070(7) -0.0102(7) -0.0094(7) O21 0.0250(8) 0.0312(9) 0.0320(10) 0.0005(7) -0.0141(7) -0.0079(7) N8 0.0165(8) 0.0163(8) 0.0123(8) -0.0026(7) -0.0024(6) -0.0071(7) N3 0.0139(8) 0.0148(8) 0.0113(8) -0.0033(6) -0.0017(6) -0.0071(7) N1 0.0141(8) 0.0153(8) 0.0135(8) -0.0026(6) -0.0019(6) -0.0072(7) N2 0.0146(8) 0.0161(8) 0.0136(8) -0.0018(6) -0.0022(6) -0.0085(7) C7 0.0136(9) 0.0151(10) 0.0184(10) -0.0020(8) -0.0057(8) -0.0048(8) N7 0.0169(8) 0.0183(9) 0.0155(8) -0.0060(7) -0.0014(7) -0.0102(7) N5 0.0178(9) 0.0230(10) 0.0262(10) -0.0099(8) 0.0027(7) -0.0053(8) C24 0.0210(10) 0.0171(10) 0.0151(10) -0.0030(8) -0.0040(8) -0.0086(8) C20 0.0229(10) 0.0148(10) 0.0168(10) -0.0014(8) -0.0057(8) -0.0085(8) O24 0.0377(10) 0.0360(10) 0.0310(10) -0.0053(8) 0.0124(8) -0.0228(8) C11 0.0195(10) 0.0195(11) 0.0249(12) -0.0013(9) -0.0016(9) -0.0094(9) C19 0.0193(10) 0.0156(10) 0.0150(10) -0.0041(8) -0.0042(8) -0.0092(8) C4 0.0146(9) 0.0162(10) 0.0137(10) -0.0046(8) -0.0017(7) -0.0064(8) C17 0.0143(9) 0.0193(10) 0.0158(10) -0.0062(8) -0.0016(8) -0.0074(8) C3 0.0147(9) 0.0160(10) 0.0188(10) -0.0028(8) -0.0044(8) -0.0066(8) C5 0.0170(9) 0.0175(10) 0.0154(10) -0.0040(8) -0.0030(8) -0.0073(8) C1 0.0185(10) 0.0132(9) 0.0184(10) -0.0036(8) -0.0041(8) -0.0074(8) C8 0.0160(9) 0.0172(10) 0.0221(11) -0.0052(8) -0.0056(8) -0.0060(8) C12 0.0182(10) 0.0174(10) 0.0225(11) -0.0053(8) -0.0036(8) -0.0068(8) C22 0.0233(11) 0.0287(12) 0.0228(11) -0.0103(9) 0.0034(9) -0.0189(10) C15 0.0181(9) 0.0183(10) 0.0133(10) -0.0044(8) -0.0010(7) -0.0106(8) C13 0.0205(10) 0.0157(10) 0.0187(10) -0.0009(8) -0.0042(8) -0.0107(8) C10 0.0179(10) 0.0270(12) 0.0186(11) -0.0019(9) -0.0019(8) -0.0063(9) C9 0.0193(10) 0.0243(11) 0.0198(11) -0.0079(9) -0.0058(8) -0.0060(9) C6 0.0231(10) 0.0199(10) 0.0224(11) -0.0094(9) 0.0000(8) -0.0134(9) C21 0.0322(12) 0.0215(11) 0.0168(10) -0.0018(8) -0.0017(9) -0.0184(10) C18 0.0186(10) 0.0151(10) 0.0140(10) -0.0001(8) -0.0037(8) -0.0059(8) C25 0.0162(10) 0.0303(13) 0.0164(10) -0.0093(9) 0.0029(8) -0.0099(9) C23 0.0180(10) 0.0246(11) 0.0228(11) -0.0098(9) -0.0039(8) -0.0100(9) C14 0.0139(9) 0.0255(11) 0.0217(11) -0.0031(9) -0.0006(8) -0.0113(9) C16 0.0134(9) 0.0171(10) 0.0136(9) -0.0046(8) -0.0009(7) -0.0079(8) C2 0.0231(10) 0.0219(11) 0.0134(10) -0.0031(8) 0.0011(8) -0.0112(9) C26 0.0255(12) 0.0235(12) 0.0345(14) -0.0053(10) 0.0000(10) -0.0118(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 1.9622(17) . ? Cu1 N1 1.9845(17) . ? Cu1 N2 2.0359(18) . ? Cu1 N3 2.0364(17) . ? Cu1 N5 2.2466(19) . ? Cl1 O11 1.4356(16) . ? Cl1 O12 1.4372(18) . ? Cl1 O13 1.4404(16) . ? Cl1 O14 1.4503(17) . ? Cl2 O24 1.4296(17) . ? Cl2 O21 1.4360(17) . ? Cl2 O23 1.4386(16) . ? Cl2 O22 1.4434(16) . ? N4 N6 1.316(2) . ? N4 C4 1.360(2) . ? N6 N7 1.334(2) . ? N9 N8 1.338(2) . ? N9 C17 1.353(3) . ? N9 C18 1.463(3) . ? N8 N1 1.317(2) . ? N3 C2 1.482(3) . ? N3 C1 1.495(3) . ? N3 C3 1.496(3) . ? N1 C16 1.354(3) . ? N2 C14 1.482(3) . ? N2 C13 1.490(3) . ? N2 C15 1.496(3) . ? C7 C8 1.389(3) . ? C7 C12 1.396(3) . ? C7 C6 1.519(3) . ? N7 C5 1.353(3) . ? N7 C6 1.463(3) . ? N5 C25 1.134(3) . ? C24 C19 1.389(3) . ? C24 C23 1.391(3) . ? C24 H24 0.9500 . ? C20 C21 1.377(3) . ? C20 C19 1.401(3) . ? C20 H20 0.9500 . ? C11 C12 1.387(3) . ? C11 C10 1.389(3) . ? C11 H11 0.9500 . ? C19 C18 1.510(3) . ? C4 C5 1.370(3) . ? C4 C3 1.495(3) . ? C17 C16 1.368(3) . ? C17 H17 0.9500 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 H5 0.9500 . ? C1 C13 1.516(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C8 C9 1.395(3) . ? C8 H8 0.9500 . ? C12 H12 0.9500 . ? C22 C21 1.388(3) . ? C22 C23 1.390(3) . ? C22 H22 0.9500 . ? C15 C16 1.492(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C10 C9 1.383(3) . ? C10 H10 0.9500 . ? C9 H9 0.9500 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C21 H21 0.9500 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C25 C26 1.455(3) . ? C23 H23 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? 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 N4 Cu1 N1 103.29(7) . . ? N4 Cu1 N2 164.16(7) . . ? N1 Cu1 N2 81.49(7) . . ? N4 Cu1 N3 82.42(7) . . ? N1 Cu1 N3 153.35(7) . . ? N2 Cu1 N3 86.80(7) . . ? N4 Cu1 N5 92.36(8) . . ? N1 Cu1 N5 97.70(7) . . ? N2 Cu1 N5 102.04(8) . . ? N3 Cu1 N5 108.16(7) . . ? O11 Cl1 O12 109.73(10) . . ? O11 Cl1 O13 109.70(10) . . ? O12 Cl1 O13 110.10(10) . . ? O11 Cl1 O14 109.36(10) . . ? O12 Cl1 O14 109.39(10) . . ? O13 Cl1 O14 108.55(10) . . ? O24 Cl2 O21 110.70(11) . . ? O24 Cl2 O23 109.47(11) . . ? O21 Cl2 O23 109.11(11) . . ? O24 Cl2 O22 109.70(11) . . ? O21 Cl2 O22 109.12(11) . . ? O23 Cl2 O22 108.71(10) . . ? N6 N4 C4 111.29(16) . . ? N6 N4 Cu1 133.77(13) . . ? C4 N4 Cu1 114.41(13) . . ? N4 N6 N7 104.88(15) . . ? N8 N9 C17 112.11(16) . . ? N8 N9 C18 119.66(17) . . ? C17 N9 C18 128.16(18) . . ? N1 N8 N9 105.06(16) . . ? C2 N3 C1 111.64(16) . . ? C2 N3 C3 109.58(16) . . ? C1 N3 C3 111.63(15) . . ? C2 N3 Cu1 110.15(12) . . ? C1 N3 Cu1 103.78(12) . . ? C3 N3 Cu1 109.94(12) . . ? N8 N1 C16 111.15(16) . . ? N8 N1 Cu1 137.23(13) . . ? C16 N1 Cu1 111.33(13) . . ? C14 N2 C13 110.19(15) . . ? C14 N2 C15 109.05(16) . . ? C13 N2 C15 111.87(16) . . ? C14 N2 Cu1 113.75(13) . . ? C13 N2 Cu1 107.82(12) . . ? C15 N2 Cu1 104.06(11) . . ? C8 C7 C12 119.6(2) . . ? C8 C7 C6 122.84(18) . . ? C12 C7 C6 117.54(19) . . ? N6 N7 C5 112.57(16) . . ? N6 N7 C6 119.20(17) . . ? C5 N7 C6 127.80(17) . . ? C25 N5 Cu1 124.70(17) . . ? C19 C24 C23 119.9(2) . . ? C19 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C21 C20 C19 120.5(2) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C12 C11 C10 120.1(2) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C24 C19 C20 119.36(19) . . ? C24 C19 C18 123.08(18) . . ? C20 C19 C18 117.52(18) . . ? N4 C4 C5 106.82(18) . . ? N4 C4 C3 117.95(17) . . ? C5 C4 C3 134.95(18) . . ? N9 C17 C16 104.65(18) . . ? N9 C17 H17 127.7 . . ? C16 C17 H17 127.7 . . ? N3 C3 C4 108.00(15) . . ? N3 C3 H3A 110.1 . . ? C4 C3 H3A 110.1 . . ? N3 C3 H3B 110.1 . . ? C4 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? N7 C5 C4 104.44(18) . . ? N7 C5 H5 127.8 . . ? C4 C5 H5 127.8 . . ? N3 C1 C13 109.36(16) . . ? N3 C1 H1A 109.8 . . ? C13 C1 H1A 109.8 . . ? N3 C1 H1B 109.8 . . ? C13 C1 H1B 109.8 . . ? H1A C1 H1B 108.3 . . ? C7 C8 C9 119.8(2) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C11 C12 C7 120.2(2) . . ? C11 C12 H12 119.9 . . ? C7 C12 H12 119.9 . . ? C21 C22 C23 119.7(2) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C16 C15 N2 106.81(16) . . ? C16 C15 H15A 110.4 . . ? N2 C15 H15A 110.4 . . ? C16 C15 H15B 110.4 . . ? N2 C15 H15B 110.4 . . ? H15A C15 H15B 108.6 . . ? N2 C13 C1 110.28(16) . . ? N2 C13 H13A 109.6 . . ? C1 C13 H13A 109.6 . . ? N2 C13 H13B 109.6 . . ? C1 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? C9 C10 C11 119.8(2) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C9 C8 120.5(2) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? N7 C6 C7 112.39(17) . . ? N7 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? N7 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.9 . . ? C20 C21 C22 120.2(2) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? N9 C18 C19 112.35(16) . . ? N9 C18 H18A 109.1 . . ? C19 C18 H18A 109.1 . . ? N9 C18 H18B 109.1 . . ? C19 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? N5 C25 C26 177.3(2) . . ? C22 C23 C24 120.3(2) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C16 C17 107.04(18) . . ? N1 C16 C15 116.98(17) . . ? C17 C16 C15 135.98(19) . . ? N3 C2 H2A 109.5 . . ? N3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? 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 N1 Cu1 N4 N6 -31.79(19) . . . . ? N2 Cu1 N4 N6 -137.8(2) . . . . ? N3 Cu1 N4 N6 174.70(19) . . . . ? N5 Cu1 N4 N6 66.69(19) . . . . ? N1 Cu1 N4 C4 138.89(14) . . . . ? N2 Cu1 N4 C4 32.9(3) . . . . ? N3 Cu1 N4 C4 -14.62(14) . . . . ? N5 Cu1 N4 C4 -122.62(15) . . . . ? C4 N4 N6 N7 0.2(2) . . . . ? Cu1 N4 N6 N7 171.11(14) . . . . ? C17 N9 N8 N1 -0.2(2) . . . . ? C18 N9 N8 N1 176.84(16) . . . . ? N4 Cu1 N3 C2 -97.03(14) . . . . ? N1 Cu1 N3 C2 158.39(14) . . . . ? N2 Cu1 N3 C2 94.60(13) . . . . ? N5 Cu1 N3 C2 -7.02(14) . . . . ? N4 Cu1 N3 C1 143.34(12) . . . . ? N1 Cu1 N3 C1 38.8(2) . . . . ? N2 Cu1 N3 C1 -25.03(12) . . . . ? N5 Cu1 N3 C1 -126.65(12) . . . . ? N4 Cu1 N3 C3 23.83(13) . . . . ? N1 Cu1 N3 C3 -80.76(19) . . . . ? N2 Cu1 N3 C3 -144.55(13) . . . . ? N5 Cu1 N3 C3 113.83(13) . . . . ? N9 N8 N1 C16 0.1(2) . . . . ? N9 N8 N1 Cu1 -172.86(15) . . . . ? N4 Cu1 N1 N8 32.8(2) . . . . ? N2 Cu1 N1 N8 -162.6(2) . . . . ? N3 Cu1 N1 N8 132.46(19) . . . . ? N5 Cu1 N1 N8 -61.5(2) . . . . ? N4 Cu1 N1 C16 -140.20(13) . . . . ? N2 Cu1 N1 C16 24.42(13) . . . . ? N3 Cu1 N1 C16 -40.5(2) . . . . ? N5 Cu1 N1 C16 125.52(14) . . . . ? N4 Cu1 N2 C14 -170.4(2) . . . . ? N1 Cu1 N2 C14 80.70(14) . . . . ? N3 Cu1 N2 C14 -123.31(14) . . . . ? N5 Cu1 N2 C14 -15.42(15) . . . . ? N4 Cu1 N2 C13 -47.8(3) . . . . ? N1 Cu1 N2 C13 -156.78(13) . . . . ? N3 Cu1 N2 C13 -0.80(13) . . . . ? N5 Cu1 N2 C13 107.10(13) . . . . ? N4 Cu1 N2 C15 71.1(3) . . . . ? N1 Cu1 N2 C15 -37.84(12) . . . . ? N3 Cu1 N2 C15 118.14(12) . . . . ? N5 Cu1 N2 C15 -133.97(12) . . . . ? N4 N6 N7 C5 -0.2(2) . . . . ? N4 N6 N7 C6 -173.28(17) . . . . ? N4 Cu1 N5 C25 -64.2(2) . . . . ? N1 Cu1 N5 C25 39.6(2) . . . . ? N2 Cu1 N5 C25 122.5(2) . . . . ? N3 Cu1 N5 C25 -146.9(2) . . . . ? C23 C24 C19 C20 0.9(3) . . . . ? C23 C24 C19 C18 178.52(19) . . . . ? C21 C20 C19 C24 0.1(3) . . . . ? C21 C20 C19 C18 -177.64(19) . . . . ? N6 N4 C4 C5 -0.1(2) . . . . ? Cu1 N4 C4 C5 -172.91(13) . . . . ? N6 N4 C4 C3 174.71(17) . . . . ? Cu1 N4 C4 C3 1.9(2) . . . . ? N8 N9 C17 C16 0.2(2) . . . . ? C18 N9 C17 C16 -176.54(18) . . . . ? C2 N3 C3 C4 93.49(19) . . . . ? C1 N3 C3 C4 -142.31(17) . . . . ? Cu1 N3 C3 C4 -27.70(19) . . . . ? N4 C4 C3 N3 17.6(2) . . . . ? C5 C4 C3 N3 -169.4(2) . . . . ? N6 N7 C5 C4 0.2(2) . . . . ? C6 N7 C5 C4 172.48(19) . . . . ? N4 C4 C5 N7 0.0(2) . . . . ? C3 C4 C5 N7 -173.6(2) . . . . ? C2 N3 C1 C13 -72.1(2) . . . . ? C3 N3 C1 C13 164.83(16) . . . . ? Cu1 N3 C1 C13 46.48(17) . . . . ? C12 C7 C8 C9 -0.4(3) . . . . ? C6 C7 C8 C9 179.54(19) . . . . ? C10 C11 C12 C7 -0.1(3) . . . . ? C8 C7 C12 C11 0.2(3) . . . . ? C6 C7 C12 C11 -179.71(19) . . . . ? C14 N2 C15 C16 -78.01(19) . . . . ? C13 N2 C15 C16 159.84(15) . . . . ? Cu1 N2 C15 C16 43.71(16) . . . . ? C14 N2 C13 C1 151.72(18) . . . . ? C15 N2 C13 C1 -86.8(2) . . . . ? Cu1 N2 C13 C1 27.04(19) . . . . ? N3 C1 C13 N2 -50.6(2) . . . . ? C12 C11 C10 C9 0.1(3) . . . . ? C11 C10 C9 C8 -0.2(3) . . . . ? C7 C8 C9 C10 0.4(3) . . . . ? N6 N7 C6 C7 81.8(2) . . . . ? C5 N7 C6 C7 -90.0(2) . . . . ? C8 C7 C6 N7 1.9(3) . . . . ? C12 C7 C6 N7 -178.16(17) . . . . ? C19 C20 C21 C22 -0.9(3) . . . . ? C23 C22 C21 C20 0.8(3) . . . . ? N8 N9 C18 C19 -98.4(2) . . . . ? C17 N9 C18 C19 78.1(2) . . . . ? C24 C19 C18 N9 17.8(3) . . . . ? C20 C19 C18 N9 -164.57(18) . . . . ? Cu1 N5 C25 C26 12(6) . . . . ? C21 C22 C23 C24 0.3(3) . . . . ? C19 C24 C23 C22 -1.1(3) . . . . ? N8 N1 C16 C17 0.0(2) . . . . ? Cu1 N1 C16 C17 174.86(13) . . . . ? N8 N1 C16 C15 -179.20(16) . . . . ? Cu1 N1 C16 C15 -4.3(2) . . . . ? N9 C17 C16 N1 -0.1(2) . . . . ? N9 C17 C16 C15 178.9(2) . . . . ? N2 C15 C16 N1 -27.5(2) . . . . ? N2 C15 C16 C17 153.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.618 _refine_diff_density_min -0.454 _refine_diff_density_rms 0.072 # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 851241' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_update_record ; 2013-09-02 # Formatted by publCIF ; # publcif _publ_body_element loop end _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common '[CuL6(ClO4)](ClO4)' _chemical_melting_point ? _chemical_formula_moiety 'C25 H32 Cl Cu N8 O4, Cl O4' _chemical_formula_sum 'C25 H32 Cl2 Cu N8 O8' _chemical_formula_weight 707.04 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Cmc21 _symmetry_space_group_Hall C2c-2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 14.8356(4) _cell_length_b 25.4907(6) _cell_length_c 8.1556(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3084.20(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2520 _cell_measurement_theta_min 1.588 _cell_measurement_theta_max 30.238 _exptl_crystal_description prismatic _exptl_crystal_colour purple _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1460.0 _exptl_absorpt_coefficient_mu 0.942 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.754 _exptl_absorpt_correction_T_max 0.885 _exptl_absorpt_process_details ; (see. N.W. Alcock (1970). Cryst. Computing, p271) ; _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 KappaCCD _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8960 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 30.238 _reflns_number_total 4755 _reflns_number_gt 4401 _reflns_threshold_expression >2sigma(I) _reflns_Friedel_coverage 0.799 _reflns_Friedel_fraction_max 0.909 _reflns_Friedel_fraction_full 0.898 _computing_data_collection 'Collect Bruker-Nonius' _computing_cell_refinement HKL2000 _computing_data_reduction HKL2000 _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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 ; w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+10.6592P] 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_abs_structure_details ; Flack x determined using 1871 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.473(8) _refine_ls_number_reflns 4755 _refine_ls_number_parameters 212 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1365 _refine_ls_wR_factor_gt 0.1239 _refine_ls_goodness_of_fit_ref 1.192 _refine_ls_restrained_S_all 1.192 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.77978(2) 0.62396(8) 0.01190(16) Uani 1 2 d S T P . . N1 N 0.0994(2) 0.82954(14) 0.6545(5) 0.0162(7) Uani 1 1 d . . . . . N2 N 0.1030(2) 0.72642(12) 0.6226(6) 0.0125(5) Uani 1 1 d . . . . . N3 N 0.1057(2) 0.87715(15) 0.7151(5) 0.0177(7) Uani 1 1 d . . . . . N4 N 0.1934(2) 0.88738(15) 0.7242(5) 0.0158(7) Uani 1 1 d . . . . . C1 C 0.0000 0.6494(2) 0.5653(8) 0.0150(10) Uani 1 2 d S T P . . H1A H 0.0000 0.6423 0.6846 0.018 Uiso 1 2 calc R U P . . H1B H 0.0000 0.6151 0.5080 0.018 Uiso 1 2 calc R U P . . C2 C 0.0862(3) 0.67853(16) 0.5216(5) 0.0139(7) Uani 1 1 d . . . . . H2A H 0.1379 0.6543 0.5347 0.017 Uiso 1 1 calc R U . . . H2B H 0.0834 0.6889 0.4047 0.017 Uiso 1 1 calc R U . . . C3 C 0.1238(3) 0.71192(18) 0.7958(6) 0.0171(8) Uani 1 1 d . . . . . H3A H 0.0732 0.6920 0.8418 0.026 Uiso 1 1 calc R U . . . H3B H 0.1331 0.7439 0.8606 0.026 Uiso 1 1 calc R U . . . H3C H 0.1785 0.6904 0.7989 0.026 Uiso 1 1 calc R U . . . C7 C 0.1837(3) 0.75491(17) 0.5549(6) 0.0160(7) Uani 1 1 d . . . . . H7A H 0.2399 0.7365 0.5858 0.019 Uiso 1 1 calc R U . . . H7B H 0.1802 0.7567 0.4338 0.019 Uiso 1 1 calc R U . . . C8 C 0.1827(2) 0.80886(14) 0.6263(6) 0.0148(6) Uani 1 1 d . . . . . C9 C 0.2442(3) 0.84629(16) 0.6716(5) 0.0151(7) Uani 1 1 d . . . . . H9 H 0.3081 0.8440 0.6671 0.018 Uiso 1 1 calc R U . . . C10 C 0.2220(3) 0.93743(17) 0.7958(6) 0.0173(8) Uani 1 1 d . . . . . H10A H 0.1739 0.9638 0.7792 0.021 Uiso 1 1 calc R U . . . H10B H 0.2767 0.9499 0.7385 0.021 Uiso 1 1 calc R U . . . C11 C 0.2417(3) 0.93269(17) 0.9767(6) 0.0162(8) Uani 1 1 d . . . . . C16 C 0.3238(3) 0.95146(17) 1.0390(6) 0.0164(8) Uani 1 1 d . . . . . H16 H 0.3668 0.9667 0.9671 0.020 Uiso 1 1 calc R U . . . C15 C 0.3423(3) 0.94786(19) 1.2055(6) 0.0203(9) Uani 1 1 d . . . . . H15 H 0.3977 0.9610 1.2472 0.024 Uiso 1 1 calc R U . . . C14 C 0.2803(4) 0.92519(19) 1.3112(6) 0.0245(10) Uani 1 1 d . . . . . H14 H 0.2935 0.9226 1.4249 0.029 Uiso 1 1 calc R U . . . C13 C 0.1987(4) 0.9062(2) 1.2510(7) 0.0283(11) Uani 1 1 d . . . . . H13 H 0.1563 0.8907 1.3235 0.034 Uiso 1 1 calc R U . . . C12 C 0.1791(3) 0.9101(2) 1.0841(6) 0.0241(10) Uani 1 1 d . . . . . H12 H 0.1233 0.8974 1.0433 0.029 Uiso 1 1 calc R U . . . Cl1 Cl 0.0000 0.77778(7) 0.1770(2) 0.0225(3) Uani 1 2 d S T P . . O1A O 0.0000 0.8033(3) 0.3350(7) 0.0315(12) Uani 1 2 d S T P . . O1B O 0.0000 0.8156(3) 0.0480(7) 0.0351(13) Uani 1 2 d S T P . . O1C O -0.0792(4) 0.7457(3) 0.1655(6) 0.0562(16) Uani 1 1 d . . . . . Cl2 Cl 0.0000 0.58251(5) 0.10445(18) 0.0153(3) Uani 1 2 d S T P . . O2A O 0.0000 0.6185(3) -0.0283(9) 0.052(2) Uani 1 2 d S T P . . O2B O 0.0791(3) 0.58981(19) 0.2037(6) 0.0350(10) Uani 1 1 d . . . . . O2C O 0.0000 0.5301(2) 0.0378(9) 0.0350(13) Uani 1 2 d S T P . . 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 Cu1 0.0090(3) 0.0111(3) 0.0155(3) -0.0014(3) 0.000 0.000 N1 0.0127(14) 0.0141(14) 0.022(2) -0.0016(13) -0.0011(12) -0.0005(11) N2 0.0109(12) 0.0124(13) 0.0141(14) 0.0000(14) -0.0003(15) 0.0002(10) N3 0.0123(15) 0.0166(16) 0.0241(19) -0.0021(14) -0.0018(14) -0.0018(12) N4 0.0135(16) 0.0160(16) 0.0179(17) 0.0012(13) -0.0020(13) -0.0031(12) C1 0.017(2) 0.012(2) 0.016(2) -0.0034(19) 0.000 0.000 C2 0.0171(17) 0.0110(16) 0.0134(17) -0.0026(14) 0.0015(14) 0.0008(13) C3 0.019(2) 0.0187(19) 0.0133(18) 0.0020(15) -0.0033(15) 0.0013(15) C7 0.0130(17) 0.0165(18) 0.0186(19) -0.0024(15) 0.0018(15) -0.0002(14) C8 0.0115(14) 0.0158(15) 0.0173(17) -0.0004(18) 0.0010(17) -0.0004(12) C9 0.0129(16) 0.0161(17) 0.0162(17) 0.0007(14) -0.0013(13) -0.0007(14) C10 0.020(2) 0.0135(18) 0.018(2) 0.0022(15) -0.0039(16) -0.0050(15) C11 0.0172(19) 0.0127(18) 0.019(2) -0.0005(15) 0.0005(16) 0.0000(15) C16 0.0200(19) 0.0104(17) 0.019(2) -0.0020(15) -0.0023(16) 0.0001(15) C15 0.026(2) 0.0151(19) 0.020(2) -0.0028(16) -0.0045(17) 0.0016(16) C14 0.038(3) 0.019(2) 0.017(2) -0.0004(16) 0.0017(19) 0.0023(19) C13 0.036(3) 0.028(2) 0.021(2) 0.0037(19) 0.007(2) -0.003(2) C12 0.022(2) 0.025(2) 0.025(3) 0.0023(17) 0.0027(17) -0.0061(17) Cl1 0.0267(8) 0.0264(8) 0.0144(6) 0.0029(6) 0.000 0.000 O1A 0.043(3) 0.031(3) 0.021(3) -0.004(2) 0.000 0.000 O1B 0.041(3) 0.040(3) 0.025(3) 0.016(2) 0.000 0.000 O1C 0.066(3) 0.078(4) 0.025(2) 0.009(2) -0.010(2) -0.043(3) Cl2 0.0143(5) 0.0177(5) 0.0139(6) 0.0029(5) 0.000 0.000 O2A 0.093(6) 0.036(4) 0.026(3) 0.016(3) 0.000 0.000 O2B 0.0177(17) 0.053(3) 0.035(2) -0.0073(19) -0.0076(16) -0.0047(16) O2C 0.034(3) 0.023(3) 0.048(4) -0.010(2) 0.000 0.000 _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 Cu1 N1 1.961(4) . ? Cu1 N1 1.961(4) 3 ? Cu1 N2 2.046(3) . ? Cu1 N2 2.046(3) 3 ? Cu1 O1A 2.432(6) . ? N1 N3 1.314(5) . ? N1 C8 1.362(5) . ? N2 C3 1.493(6) . ? N2 C2 1.494(5) . ? N2 C7 1.504(5) . ? N3 N4 1.330(5) . ? N4 C9 1.360(6) . ? N4 C10 1.466(6) . ? C1 C2 1.521(5) . ? C1 C2 1.522(5) 3 ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C7 C8 1.493(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.371(5) . ? C9 H9 0.9500 . ? C10 C11 1.509(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.400(6) . ? C11 C16 1.403(6) . ? C16 C15 1.388(6) . ? C16 H16 0.9500 . ? C15 C14 1.386(7) . ? C15 H15 0.9500 . ? C14 C13 1.393(8) . ? C14 H14 0.9500 . ? C13 C12 1.395(8) . ? C13 H13 0.9500 . ? C12 H12 0.9500 . ? Cl1 O1B 1.426(6) . ? Cl1 O1C 1.434(5) 3 ? Cl1 O1C 1.434(5) . ? Cl1 O1A 1.444(6) . ? Cl2 O2A 1.420(6) . ? Cl2 O2B 1.438(4) . ? Cl2 O2B 1.438(4) 3 ? Cl2 O2C 1.443(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 97.5(2) . 3 ? N1 Cu1 N2 82.46(13) . . ? N1 Cu1 N2 172.96(18) 3 . ? N1 Cu1 N2 172.96(18) . 3 ? N1 Cu1 N2 82.46(13) 3 3 ? N2 Cu1 N2 96.68(17) . 3 ? N1 Cu1 O1A 87.89(15) . . ? N1 Cu1 O1A 87.89(15) 3 . ? N2 Cu1 O1A 99.14(16) . . ? N2 Cu1 O1A 99.14(16) 3 . ? N3 N1 C8 110.9(3) . . ? N3 N1 Cu1 134.3(3) . . ? C8 N1 Cu1 114.2(3) . . ? C3 N2 C2 110.7(3) . . ? C3 N2 C7 107.7(3) . . ? C2 N2 C7 109.0(3) . . ? C3 N2 Cu1 108.2(3) . . ? C2 N2 Cu1 114.9(3) . . ? C7 N2 Cu1 106.0(2) . . ? N1 N3 N4 105.7(3) . . ? N3 N4 C9 111.9(4) . . ? N3 N4 C10 118.4(4) . . ? C9 N4 C10 129.5(4) . . ? C2 C1 C2 114.4(5) . 3 ? C2 C1 H1A 108.7 . . ? C2 C1 H1A 108.7 3 . ? C2 C1 H1B 108.7 . . ? C2 C1 H1B 108.7 3 . ? H1A C1 H1B 107.6 . . ? N2 C2 C1 114.2(4) . . ? N2 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? N2 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? N2 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C8 C7 N2 107.1(3) . . ? C8 C7 H7A 110.3 . . ? N2 C7 H7A 110.3 . . ? C8 C7 H7B 110.3 . . ? N2 C7 H7B 110.3 . . ? H7A C7 H7B 108.6 . . ? N1 C8 C9 106.8(3) . . ? N1 C8 C7 115.5(3) . . ? C9 C8 C7 137.6(4) . . ? N4 C9 C8 104.6(3) . . ? N4 C9 H9 127.7 . . ? C8 C9 H9 127.7 . . ? N4 C10 C11 112.1(4) . . ? N4 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? N4 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C12 C11 C16 119.2(5) . . ? C12 C11 C10 121.1(4) . . ? C16 C11 C10 119.7(4) . . ? C15 C16 C11 120.2(5) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? C14 C15 C16 120.3(5) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C14 C13 120.1(5) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C13 C12 120.0(5) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C12 C11 120.1(5) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? O1B Cl1 O1C 109.7(3) . 3 ? O1B Cl1 O1C 109.7(3) . . ? O1C Cl1 O1C 110.0(6) 3 . ? O1B Cl1 O1A 110.7(4) . . ? O1C Cl1 O1A 108.4(3) 3 . ? O1C Cl1 O1A 108.4(3) . . ? Cl1 O1A Cu1 138.9(4) . . ? O2A Cl2 O2B 110.2(3) . . ? O2A Cl2 O2B 110.2(3) . 3 ? O2B Cl2 O2B 109.4(4) . 3 ? O2A Cl2 O2C 108.2(4) . . ? O2B Cl2 O2C 109.4(2) . . ? O2B Cl2 O2C 109.4(2) 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 C8 N1 N3 N4 0.7(5) . . . . ? Cu1 N1 N3 N4 171.1(3) . . . . ? N1 N3 N4 C9 -0.8(5) . . . . ? N1 N3 N4 C10 -177.0(4) . . . . ? C3 N2 C2 C1 68.3(4) . . . . ? C7 N2 C2 C1 -173.4(4) . . . . ? Cu1 N2 C2 C1 -54.7(5) . . . . ? C2 C1 C2 N2 68.9(6) 3 . . . ? C3 N2 C7 C8 -75.5(4) . . . . ? C2 N2 C7 C8 164.3(4) . . . . ? Cu1 N2 C7 C8 40.1(4) . . . . ? N3 N1 C8 C9 -0.4(5) . . . . ? Cu1 N1 C8 C9 -172.9(3) . . . . ? N3 N1 C8 C7 -179.2(4) . . . . ? Cu1 N1 C8 C7 8.3(5) . . . . ? N2 C7 C8 N1 -33.1(6) . . . . ? N2 C7 C8 C9 148.6(6) . . . . ? N3 N4 C9 C8 0.5(5) . . . . ? C10 N4 C9 C8 176.2(4) . . . . ? N1 C8 C9 N4 -0.1(5) . . . . ? C7 C8 C9 N4 178.3(6) . . . . ? N3 N4 C10 C11 93.5(5) . . . . ? C9 N4 C10 C11 -82.0(6) . . . . ? N4 C10 C11 C12 -51.5(6) . . . . ? N4 C10 C11 C16 128.9(4) . . . . ? C12 C11 C16 C15 -0.3(7) . . . . ? C10 C11 C16 C15 179.3(4) . . . . ? C11 C16 C15 C14 0.7(7) . . . . ? C16 C15 C14 C13 -0.5(8) . . . . ? C15 C14 C13 C12 -0.1(8) . . . . ? C14 C13 C12 C11 0.5(8) . . . . ? C16 C11 C12 C13 -0.3(7) . . . . ? C10 C11 C12 C13 -179.8(5) . . . . ? O1B Cl1 O1A Cu1 180.000(2) . . . . ? O1C Cl1 O1A Cu1 -59.7(3) 3 . . . ? O1C Cl1 O1A Cu1 59.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.371 _refine_diff_density_min -0.618 _refine_diff_density_rms 0.167 _database_code_depnum_ccdc_archive 'CCDC 851242' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_update_record ; 2013-09-02 # Formatted by publCIF ; # publcif _publ_body_element loop end _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common '[CuL1](ClO4)2' _chemical_melting_point ? _chemical_formula_moiety 'C32 H44 Cu N8 O4, 2(Cl O4)' _chemical_formula_sum 'C32 H44 Cl2 Cu N8 O12' _chemical_formula_weight 867.19 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1849(15) _cell_length_b 9.2931(8) _cell_length_c 11.8913(12) _cell_angle_alpha 98.876(4) _cell_angle_beta 108.784(5) _cell_angle_gamma 105.480(6) _cell_volume 893.40(19) _cell_formula_units_Z 1 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 8835 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 28.27 _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 451 _exptl_absorpt_coefficient_mu 0.837 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.778 _exptl_absorpt_correction_T_max 0.920 _exptl_absorpt_process_details ; (see. N.W. Alcock (1970). Cryst. Computing, p271) ; _exptl_special_details ? _diffrn_ambient_temperature 110(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-Nonius KappaApex' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4508 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8835 _diffrn_reflns_av_R_equivalents 0.0145 _diffrn_reflns_av_sigmaI/netI 0.0176 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 28.27 _reflns_number_total 4418 _reflns_number_gt 4153 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect Bruker-Nonius' _computing_cell_refinement HKL2000 _computing_data_reduction HKL2000 _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0322P)^2^+0.6072P] 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 4418 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0286 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0696 _refine_ls_wR_factor_gt 0.0684 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 Cu1 Cu 0.5000 0.5000 0.5000 0.01153(6) Uani 1 2 d S . . O3 O 0.73134(12) 0.28922(12) 0.34770(10) 0.0190(2) Uani 1 1 d . . . O1 O 0.43089(12) 0.74096(11) 0.47239(9) 0.01679(19) Uani 1 1 d . . . N1 N 0.70919(13) 0.60968(13) 0.64366(10) 0.0134(2) Uani 1 1 d . . . N2 N 0.65100(13) 0.58497(13) 0.40634(10) 0.0126(2) Uani 1 1 d . . . N3 N 0.75044(13) 0.64538(13) 0.76477(10) 0.0142(2) Uani 1 1 d . . . N4 N 0.91240(13) 0.70847(13) 0.81270(10) 0.0130(2) Uani 1 1 d . . . C1 C 0.61446(16) 0.48356(15) 0.28263(12) 0.0148(2) Uani 1 1 d . . . H1A H 0.7072 0.5223 0.2574 0.018 Uiso 1 1 calc R . . H1B H 0.5167 0.4931 0.2220 0.018 Uiso 1 1 calc R . . C2 C 0.58462(17) 0.31384(16) 0.27749(12) 0.0165(3) Uani 1 1 d . . . H2A H 0.4994 0.2763 0.3103 0.020 Uiso 1 1 calc R . . H2B H 0.5442 0.2535 0.1907 0.020 Uiso 1 1 calc R . . C3 C 0.70526(18) 0.16554(17) 0.40460(14) 0.0199(3) Uani 1 1 d . . . H3A H 0.7900 0.1172 0.4082 0.024 Uiso 1 1 calc R . . H3B H 0.5976 0.0859 0.3529 0.024 Uiso 1 1 calc R . . C4 C 0.28982(18) 0.78375(18) 0.46685(14) 0.0203(3) Uani 1 1 d . . . H4A H 0.1891 0.6944 0.4173 0.024 Uiso 1 1 calc R . . H4B H 0.2882 0.8692 0.4266 0.024 Uiso 1 1 calc R . . C5 C 0.46432(17) 0.74368(16) 0.36287(12) 0.0166(3) Uani 1 1 d . . . H5A H 0.4564 0.8390 0.3379 0.020 Uiso 1 1 calc R . . H5B H 0.3849 0.6530 0.2946 0.020 Uiso 1 1 calc R . . C6 C 0.63536(16) 0.73928(15) 0.39259(12) 0.0160(2) Uani 1 1 d . . . H6A H 0.6719 0.7660 0.3264 0.019 Uiso 1 1 calc R . . H6B H 0.7093 0.8193 0.4701 0.019 Uiso 1 1 calc R . . C7 C 0.82617(15) 0.61662(16) 0.48553(12) 0.0154(2) Uani 1 1 d . . . H7A H 0.8582 0.5253 0.4652 0.018 Uiso 1 1 calc R . . H7B H 0.8977 0.7059 0.4707 0.018 Uiso 1 1 calc R . . C8 C 0.84471(15) 0.65093(15) 0.61660(12) 0.0132(2) Uani 1 1 d . . . C9 C 0.97685(16) 0.71478(15) 0.72562(12) 0.0142(2) Uani 1 1 d . . . H9 H 1.0888 0.7546 0.7374 0.017 Uiso 1 1 calc R . . C10 C 0.99903(16) 0.77312(16) 0.94702(12) 0.0154(2) Uani 1 1 d . . . H10A H 0.9332 0.7199 0.9896 0.018 Uiso 1 1 calc R . . H10B H 1.0130 0.8845 0.9690 0.018 Uiso 1 1 calc R . . C11 C 1.16421(16) 0.75318(15) 0.98904(11) 0.0138(2) Uani 1 1 d . . . C12 C 1.17698(17) 0.60609(16) 0.96791(12) 0.0171(3) Uani 1 1 d . . . H12 H 1.0810 0.5176 0.9274 0.021 Uiso 1 1 calc R . . C13 C 1.32955(18) 0.58834(17) 1.00592(13) 0.0189(3) Uani 1 1 d . . . H13 H 1.3377 0.4878 0.9923 0.023 Uiso 1 1 calc R . . C14 C 1.47021(17) 0.71786(17) 1.06396(12) 0.0183(3) Uani 1 1 d . . . H14 H 1.5746 0.7060 1.0892 0.022 Uiso 1 1 calc R . . C15 C 1.45801(17) 0.86461(17) 1.08493(12) 0.0181(3) Uani 1 1 d . . . H15 H 1.5541 0.9530 1.1249 0.022 Uiso 1 1 calc R . . C16 C 1.30543(16) 0.88250(16) 1.04749(12) 0.0164(2) Uani 1 1 d . . . H16 H 1.2976 0.9831 1.0618 0.020 Uiso 1 1 calc R . . Cl1 Cl 0.01921(4) 0.09988(4) 0.75179(3) 0.01646(8) Uani 1 1 d . . . O32 O 0.05806(16) 0.26561(13) 0.78098(11) 0.0318(3) Uani 1 1 d . . . O31 O 0.14905(14) 0.06346(14) 0.83508(12) 0.0336(3) Uani 1 1 d . . . O33 O -0.13104(14) 0.02694(14) 0.76534(11) 0.0271(2) Uani 1 1 d . . . O34 O 0.00221(15) 0.04457(14) 0.62685(10) 0.0300(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.00911(11) 0.01432(11) 0.00930(10) 0.00333(8) 0.00295(8) 0.00165(8) O3 0.0165(5) 0.0216(5) 0.0245(5) 0.0100(4) 0.0108(4) 0.0091(4) O1 0.0180(5) 0.0207(5) 0.0170(5) 0.0084(4) 0.0091(4) 0.0098(4) N1 0.0115(5) 0.0157(5) 0.0113(5) 0.0035(4) 0.0040(4) 0.0025(4) N2 0.0111(5) 0.0150(5) 0.0110(5) 0.0035(4) 0.0040(4) 0.0033(4) N3 0.0114(5) 0.0174(5) 0.0115(5) 0.0033(4) 0.0028(4) 0.0034(4) N4 0.0107(5) 0.0141(5) 0.0122(5) 0.0023(4) 0.0029(4) 0.0037(4) C1 0.0152(6) 0.0180(6) 0.0111(6) 0.0039(5) 0.0059(5) 0.0045(5) C2 0.0166(6) 0.0181(6) 0.0146(6) 0.0032(5) 0.0060(5) 0.0059(5) C3 0.0222(7) 0.0191(6) 0.0242(7) 0.0081(5) 0.0123(6) 0.0105(5) C4 0.0183(7) 0.0258(7) 0.0223(7) 0.0101(6) 0.0090(5) 0.0122(6) C5 0.0198(6) 0.0171(6) 0.0157(6) 0.0075(5) 0.0081(5) 0.0071(5) C6 0.0172(6) 0.0144(6) 0.0170(6) 0.0063(5) 0.0077(5) 0.0037(5) C7 0.0101(6) 0.0209(6) 0.0135(6) 0.0033(5) 0.0041(5) 0.0037(5) C8 0.0111(6) 0.0147(6) 0.0132(6) 0.0036(5) 0.0046(5) 0.0035(4) C9 0.0116(6) 0.0163(6) 0.0142(6) 0.0030(5) 0.0052(5) 0.0041(5) C10 0.0142(6) 0.0183(6) 0.0110(6) 0.0002(5) 0.0030(5) 0.0057(5) C11 0.0142(6) 0.0168(6) 0.0098(5) 0.0031(4) 0.0037(5) 0.0054(5) C12 0.0172(6) 0.0160(6) 0.0165(6) 0.0031(5) 0.0060(5) 0.0043(5) C13 0.0227(7) 0.0204(6) 0.0165(6) 0.0057(5) 0.0075(5) 0.0111(5) C14 0.0161(6) 0.0269(7) 0.0139(6) 0.0066(5) 0.0051(5) 0.0104(5) C15 0.0149(6) 0.0221(7) 0.0138(6) 0.0034(5) 0.0034(5) 0.0039(5) C16 0.0163(6) 0.0162(6) 0.0149(6) 0.0030(5) 0.0047(5) 0.0048(5) Cl1 0.01673(15) 0.01565(15) 0.01526(15) 0.00339(11) 0.00550(12) 0.00389(12) O32 0.0436(7) 0.0143(5) 0.0312(6) 0.0031(4) 0.0102(5) 0.0064(5) O31 0.0207(6) 0.0296(6) 0.0386(7) 0.0106(5) -0.0030(5) 0.0069(5) O33 0.0223(5) 0.0329(6) 0.0323(6) 0.0118(5) 0.0171(5) 0.0089(5) O34 0.0369(7) 0.0313(6) 0.0196(5) 0.0010(5) 0.0162(5) 0.0049(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 Cu1 N1 1.9881(11) 2_666 ? Cu1 N1 1.9881(11) . ? Cu1 N2 2.1140(11) . ? Cu1 N2 2.1140(11) 2_666 ? O3 C3 1.4260(17) . ? O3 C2 1.4369(16) . ? O1 C5 1.4334(16) . ? O1 C4 1.4386(16) . ? N1 N3 1.3272(15) . ? N1 C8 1.3570(16) . ? N2 C7 1.4993(16) . ? N2 C1 1.5001(16) . ? N2 C6 1.5070(17) . ? N3 N4 1.3292(15) . ? N4 C9 1.3494(17) . ? N4 C10 1.4750(16) . ? C1 C2 1.5150(18) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.511(2) 2_666 ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C3 1.511(2) 2_666 ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5085(19) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.4854(18) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.3678(18) . ? C9 H9 0.9500 . ? C10 C11 1.5087(18) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.3927(19) . ? C11 C12 1.3942(18) . ? C12 C13 1.391(2) . ? C12 H12 0.9500 . ? C13 C14 1.391(2) . ? C13 H13 0.9500 . ? C14 C15 1.389(2) . ? C14 H14 0.9500 . ? C15 C16 1.3911(19) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? Cl1 O33 1.4379(11) . ? Cl1 O34 1.4380(11) . ? Cl1 O31 1.4409(12) . ? Cl1 O32 1.4428(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 180.0 2_666 . ? N1 Cu1 N2 99.28(4) 2_666 . ? N1 Cu1 N2 80.72(4) . . ? N1 Cu1 N2 80.72(4) 2_666 2_666 ? N1 Cu1 N2 99.28(4) . 2_666 ? N2 Cu1 N2 180.0 . 2_666 ? C3 O3 C2 114.41(11) . . ? C5 O1 C4 112.30(10) . . ? N3 N1 C8 110.15(10) . . ? N3 N1 Cu1 134.21(9) . . ? C8 N1 Cu1 115.50(9) . . ? C7 N2 C1 108.24(10) . . ? C7 N2 C6 106.47(10) . . ? C1 N2 C6 109.49(10) . . ? C7 N2 Cu1 109.52(8) . . ? C1 N2 Cu1 116.24(8) . . ? C6 N2 Cu1 106.46(8) . . ? N1 N3 N4 105.42(10) . . ? N3 N4 C9 112.45(11) . . ? N3 N4 C10 119.81(11) . . ? C9 N4 C10 127.54(11) . . ? N2 C1 C2 114.84(10) . . ? N2 C1 H1A 108.6 . . ? C2 C1 H1A 108.6 . . ? N2 C1 H1B 108.6 . . ? C2 C1 H1B 108.6 . . ? H1A C1 H1B 107.5 . . ? O3 C2 C1 111.35(11) . . ? O3 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? O3 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? O3 C3 C4 113.40(12) . 2_666 ? O3 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 2_666 . ? O3 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 2_666 . ? H3A C3 H3B 107.7 . . ? O1 C4 C3 109.80(11) . 2_666 ? O1 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 2_666 . ? O1 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 2_666 . ? H4A C4 H4B 108.2 . . ? O1 C5 C6 106.89(11) . . ? O1 C5 H5A 110.3 . . ? C6 C5 H5A 110.3 . . ? O1 C5 H5B 110.3 . . ? C6 C5 H5B 110.3 . . ? H5A C5 H5B 108.6 . . ? N2 C6 C5 114.01(11) . . ? N2 C6 H6A 108.7 . . ? C5 C6 H6A 108.7 . . ? N2 C6 H6B 108.7 . . ? C5 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C8 C7 N2 108.56(10) . . ? C8 C7 H7A 110.0 . . ? N2 C7 H7A 110.0 . . ? C8 C7 H7B 110.0 . . ? N2 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? N1 C8 C9 107.51(11) . . ? N1 C8 C7 118.90(11) . . ? C9 C8 C7 133.54(12) . . ? N4 C9 C8 104.47(11) . . ? N4 C9 H9 127.8 . . ? C8 C9 H9 127.8 . . ? N4 C10 C11 110.55(10) . . ? N4 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? N4 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C16 C11 C12 119.56(12) . . ? C16 C11 C10 119.95(12) . . ? C12 C11 C10 120.48(12) . . ? C13 C12 C11 120.29(13) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 119.93(13) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C15 C14 C13 119.95(13) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.19(13) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 120.08(13) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? O33 Cl1 O34 109.43(7) . . ? O33 Cl1 O31 109.03(8) . . ? O34 Cl1 O31 110.13(8) . . ? O33 Cl1 O32 110.15(8) . . ? O34 Cl1 O32 109.17(7) . . ? O31 Cl1 O32 108.93(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 N1 N3 17(100) 2_666 . . . ? N2 Cu1 N1 N3 170.97(13) . . . . ? N2 Cu1 N1 N3 -9.03(13) 2_666 . . . ? N1 Cu1 N1 C8 -168(100) 2_666 . . . ? N2 Cu1 N1 C8 -14.01(9) . . . . ? N2 Cu1 N1 C8 165.99(9) 2_666 . . . ? N1 Cu1 N2 C7 -157.27(8) 2_666 . . . ? N1 Cu1 N2 C7 22.73(8) . . . . ? N2 Cu1 N2 C7 77(100) 2_666 . . . ? N1 Cu1 N2 C1 -34.25(9) 2_666 . . . ? N1 Cu1 N2 C1 145.75(9) . . . . ? N2 Cu1 N2 C1 -160(100) 2_666 . . . ? N1 Cu1 N2 C6 88.00(8) 2_666 . . . ? N1 Cu1 N2 C6 -92.00(8) . . . . ? N2 Cu1 N2 C6 -38(100) 2_666 . . . ? C8 N1 N3 N4 -0.24(14) . . . . ? Cu1 N1 N3 N4 174.98(9) . . . . ? N1 N3 N4 C9 0.15(14) . . . . ? N1 N3 N4 C10 175.30(11) . . . . ? C7 N2 C1 C2 78.76(13) . . . . ? C6 N2 C1 C2 -165.57(11) . . . . ? Cu1 N2 C1 C2 -44.93(13) . . . . ? C3 O3 C2 C1 146.96(11) . . . . ? N2 C1 C2 O3 -68.15(14) . . . . ? C2 O3 C3 C4 -90.76(14) . . . 2_666 ? C5 O1 C4 C3 -159.78(11) . . . 2_666 ? C4 O1 C5 C6 165.26(11) . . . . ? C7 N2 C6 C5 -156.14(11) . . . . ? C1 N2 C6 C5 87.06(13) . . . . ? Cu1 N2 C6 C5 -39.35(12) . . . . ? O1 C5 C6 N2 71.83(14) . . . . ? C1 N2 C7 C8 -154.38(10) . . . . ? C6 N2 C7 C8 87.99(12) . . . . ? Cu1 N2 C7 C8 -26.73(12) . . . . ? N3 N1 C8 C9 0.25(15) . . . . ? Cu1 N1 C8 C9 -175.96(9) . . . . ? N3 N1 C8 C7 178.14(11) . . . . ? Cu1 N1 C8 C7 1.94(15) . . . . ? N2 C7 C8 N1 17.40(16) . . . . ? N2 C7 C8 C9 -165.37(14) . . . . ? N3 N4 C9 C8 0.00(15) . . . . ? C10 N4 C9 C8 -174.70(12) . . . . ? N1 C8 C9 N4 -0.14(14) . . . . ? C7 C8 C9 N4 -177.60(14) . . . . ? N3 N4 C10 C11 147.40(12) . . . . ? C9 N4 C10 C11 -38.25(18) . . . . ? N4 C10 C11 C16 120.08(13) . . . . ? N4 C10 C11 C12 -58.79(16) . . . . ? C16 C11 C12 C13 0.6(2) . . . . ? C10 C11 C12 C13 179.49(12) . . . . ? C11 C12 C13 C14 -0.8(2) . . . . ? C12 C13 C14 C15 0.6(2) . . . . ? C13 C14 C15 C16 -0.3(2) . . . . ? C14 C15 C16 C11 0.1(2) . . . . ? C12 C11 C16 C15 -0.3(2) . . . . ? C10 C11 C16 C15 -179.18(12) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.359 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 854682' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_update_record ; 2013-09-02 # Formatted by publCIF ; # publcif _publ_body_element loop end _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H42 N8 O4, 2(Cl O4), 2(H2 O)' _chemical_formula_sum 'C30 H46 Cl2 N8 O14' _chemical_formula_weight 813.65 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_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.900(4) _cell_length_b 11.582(3) _cell_length_c 16.395(3) _cell_angle_alpha 71.824(11) _cell_angle_beta 79.864(15) _cell_angle_gamma 68.647(12) _cell_volume 1827.1(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12810 _cell_measurement_theta_min 1.31 _cell_measurement_theta_max 25.00 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 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-Nonius KappaApex' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4508 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12810 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.310 _diffrn_reflns_theta_max 26.000 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 7193 _reflns_number_gt 5539 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect Bruker-Nonius' _computing_cell_refinement HKL2000 _computing_data_reduction HKL2000 _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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 ; w=1/[\s^2^(Fo^2^)+(0.0702P)^2^+3.0544P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 7193 _refine_ls_number_parameters 527 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0968 _refine_ls_R_factor_gt 0.0706 _refine_ls_wR_factor_ref 0.1779 _refine_ls_wR_factor_gt 0.1638 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.9160(2) 0.0766(2) 0.82561(15) 0.0276(6) Uani 1 1 d . . . . . N4 N 0.5149(3) -0.2972(3) 0.97686(17) 0.0194(6) Uani 1 1 d . . . . . N2' N 0.6743(3) 0.6264(3) 0.54348(17) 0.0213(6) Uani 1 1 d . . . . . H1' H 0.5905 0.6229 0.5291 0.026 Uiso 1 1 calc R U . . . O2' O 0.6841(3) 0.5379(3) 0.39911(15) 0.0329(6) Uani 1 1 d . . . . . O2 O 1.1297(2) 0.0977(2) 0.87858(15) 0.0288(6) Uani 1 1 d . . . . . N3' N 1.0139(3) 0.7727(3) 0.45628(19) 0.0284(7) Uani 1 1 d . . . . . N2 N 0.8011(3) -0.0930(3) 0.96161(18) 0.0233(6) Uani 1 1 d . . . . . H1 H 0.8916 -0.0903 0.9623 0.028 Uiso 1 1 calc R U . . . O22 O 0.8003(3) 0.5230(3) 0.81942(17) 0.0365(6) Uani 1 1 d . . . . . N3 N 0.4957(3) -0.2827(3) 1.05736(18) 0.0239(6) Uani 1 1 d . . . . . N1' N 0.9166(3) 0.7477(3) 0.43700(19) 0.0268(7) Uani 1 1 d . . . . . N4' N 0.9743(3) 0.8112(3) 0.52945(18) 0.0236(6) Uani 1 1 d . . . . . N1 N 0.5965(3) -0.2554(3) 1.06963(18) 0.0243(6) Uani 1 1 d . . . . . C8' C 0.8139(3) 0.7702(3) 0.4977(2) 0.0214(7) Uani 1 1 d . . . . . C9' C 0.8501(3) 0.8107(3) 0.5567(2) 0.0259(7) Uani 1 1 d . . . . . H9' H 0.7991 0.8335 0.6061 0.031 Uiso 1 1 calc R U . . . C6' C 0.8049(4) 0.5241(4) 0.4280(2) 0.0279(8) Uani 1 1 d . . . . . H6'1 H 0.8333 0.5992 0.3964 0.033 Uiso 1 1 calc R U . . . H6'2 H 0.8744 0.4454 0.4178 0.033 Uiso 1 1 calc R U . . . C9 C 0.6284(3) -0.2789(3) 0.9380(2) 0.0225(7) Uani 1 1 d . . . . . H9 H 0.6643 -0.2829 0.8814 0.027 Uiso 1 1 calc R U . . . O1' O 0.4953(3) 0.5200(2) 0.66664(15) 0.0299(6) Uani 1 1 d . . . . . C7 C 0.8093(3) -0.2325(3) 0.9927(2) 0.0240(7) Uani 1 1 d . . . . . H7A H 0.8734 -0.2798 0.9537 0.029 Uiso 1 1 calc R U . . . H7B H 0.8436 -0.2696 1.0506 0.029 Uiso 1 1 calc R U . . . C15 C 0.3317(3) -0.3804(3) 1.0017(2) 0.0254(7) Uani 1 1 d . . . . . H15 H 0.3327 -0.3942 1.0619 0.030 Uiso 1 1 calc R U . . . C8 C 0.6808(3) -0.2534(3) 0.9972(2) 0.0211(7) Uani 1 1 d . . . . . C10' C 1.0607(3) 0.8451(3) 0.5680(2) 0.0257(7) Uani 1 1 d . . . . . C5' C 0.7839(3) 0.5148(3) 0.5224(2) 0.0247(7) Uani 1 1 d . . . . . H5'1 H 0.7642 0.4347 0.5536 0.030 Uiso 1 1 calc R U . . . H5'2 H 0.8665 0.5091 0.5429 0.030 Uiso 1 1 calc R U . . . C10 C 0.4209(3) -0.3291(3) 0.9449(2) 0.0223(7) Uani 1 1 d . . . . . C11 C 0.4209(4) -0.3093(4) 0.8570(2) 0.0291(8) Uani 1 1 d . . . . . H11 H 0.4813 -0.2731 0.8180 0.035 Uiso 1 1 calc R U . . . O23 O 0.9076(3) 0.6668(3) 0.8170(2) 0.0542(9) Uani 1 1 d . . . . . C2' C 0.6186(4) 0.5048(4) 0.6929(2) 0.0304(8) Uani 1 1 d . . . . . H2'1 H 0.6852 0.4233 0.6849 0.037 Uiso 1 1 calc R U . . . H2'2 H 0.6103 0.5020 0.7545 0.037 Uiso 1 1 calc R U . . . C14 C 0.2407(3) -0.4114(3) 0.9702(2) 0.0287(8) Uani 1 1 d . . . . . H14 H 0.1781 -0.4448 1.0087 0.034 Uiso 1 1 calc R U . . . C1' C 0.6604(4) 0.6178(4) 0.6386(2) 0.0268(8) Uani 1 1 d . . . . . H1'1 H 0.7460 0.6096 0.6566 0.032 Uiso 1 1 calc R U . . . H1'2 H 0.5943 0.6983 0.6486 0.032 Uiso 1 1 calc R U . . . C7' C 0.6861(3) 0.7561(3) 0.4914(2) 0.0233(7) Uani 1 1 d . . . . . H7'1 H 0.6752 0.7685 0.4303 0.028 Uiso 1 1 calc R U . . . H7'2 H 0.6135 0.8248 0.5115 0.028 Uiso 1 1 calc R U . . . C6 C 0.7094(4) -0.0122(4) 1.0186(3) 0.0313(8) Uani 1 1 d . . . . . H6A H 0.7198 0.0739 0.9999 0.038 Uiso 1 1 calc R U . . . H6B H 0.6171 -0.0003 1.0109 0.038 Uiso 1 1 calc R U . . . C1 C 0.7626(4) -0.0354(4) 0.8696(2) 0.0303(8) Uani 1 1 d . . . . . H1A H 0.6689 -0.0260 0.8685 0.036 Uiso 1 1 calc R U . . . H1B H 0.8164 -0.0958 0.8354 0.036 Uiso 1 1 calc R U . . . C12 C 0.3315(4) -0.3432(4) 0.8270(2) 0.0329(9) Uani 1 1 d . . . . . H12 H 0.3319 -0.3316 0.7670 0.039 Uiso 1 1 calc R U . . . C13 C 0.2417(4) -0.3937(3) 0.8828(3) 0.0316(8) Uani 1 1 d . . . . . H13 H 0.1806 -0.4161 0.8612 0.038 Uiso 1 1 calc R U . . . O24 O 1.0216(3) 0.4482(3) 0.8503(2) 0.0639(10) Uani 1 1 d . . . . . C15' C 1.1750(4) 0.8616(4) 0.5214(3) 0.0381(9) Uani 1 1 d . . . . . H15' H 1.1967 0.8508 0.4649 0.046 Uiso 1 1 calc R U . . . C3' C 0.4466(4) 0.4169(4) 0.7146(2) 0.0358(9) Uani 1 1 d . . . . . H3'1 H 0.4466 0.4049 0.7771 0.043 Uiso 1 1 calc R U . . . H3'2 H 0.5038 0.3356 0.7009 0.043 Uiso 1 1 calc R U . . . C11' C 1.0265(4) 0.8628(4) 0.6496(3) 0.0358(9) Uani 1 1 d . . . . . H11' H 0.9476 0.8513 0.6806 0.043 Uiso 1 1 calc R U . . . C5 C 1.2666(4) 0.0697(4) 0.8874(3) 0.0335(9) Uani 1 1 d . . . . . H5A H 1.2898 0.1496 0.8652 0.040 Uiso 1 1 calc R U . . . H5B H 1.3218 0.0082 0.8542 0.040 Uiso 1 1 calc R U . . . C2 C 0.7804(4) 0.0942(4) 0.8277(3) 0.0339(9) Uani 1 1 d . . . . . H2A H 0.7507 0.1284 0.7685 0.041 Uiso 1 1 calc R U . . . H2B H 0.7277 0.1562 0.8611 0.041 Uiso 1 1 calc R U . . . C13' C 1.2247(4) 0.9130(4) 0.6407(3) 0.0375(10) Uani 1 1 d . . . . . H13' H 1.2813 0.9363 0.6658 0.045 Uiso 1 1 calc R U . . . C3 C 0.9456(4) 0.1943(3) 0.7920(2) 0.0318(8) Uani 1 1 d . . . . . H3A H 0.8985 0.2537 0.8283 0.038 Uiso 1 1 calc R U . . . H3B H 0.9170 0.2370 0.7328 0.038 Uiso 1 1 calc R U . . . C4 C 1.0912(4) 0.1624(4) 0.7919(2) 0.0326(9) Uani 1 1 d . . . . . H4A H 1.1380 0.1059 0.7537 0.039 Uiso 1 1 calc R U . . . H4B H 1.1146 0.2421 0.7702 0.039 Uiso 1 1 calc R U . . . O11 O 0.5282(3) -0.0288(3) 0.6121(2) 0.0431(7) Uani 1 1 d . . . . . C4' C 0.3088(4) 0.4509(4) 0.6906(2) 0.0384(10) Uani 1 1 d . . . . . H4'1 H 0.2709 0.3830 0.7242 0.046 Uiso 1 1 calc R U . . . H4'2 H 0.2521 0.5333 0.7028 0.046 Uiso 1 1 calc R U . . . C12' C 1.1090(4) 0.8975(4) 0.6855(3) 0.0419(10) Uani 1 1 d . . . . . H12' H 1.0861 0.9109 0.7413 0.050 Uiso 1 1 calc R U . . . C14' C 1.2571(4) 0.8943(4) 0.5598(3) 0.0401(10) Uani 1 1 d . . . . . H14' H 1.3371 0.9040 0.5296 0.048 Uiso 1 1 calc R U . . . O21 O 0.9630(3) 0.5593(3) 0.71011(18) 0.0470(8) Uani 1 1 d . . . . . O1W O 1.0613(3) -0.1213(3) 0.9668(2) 0.0404(7) Uani 1 1 d D . . . . H1AW H 1.073(5) -0.041(3) 0.930(3) 0.061 Uiso 1 1 d D U . . . H1BW H 1.122(4) -0.202(2) 0.960(3) 0.061 Uiso 1 1 d D U . . . O2W O 0.4410(3) 0.6478(3) 0.4854(2) 0.0503(8) Uani 1 1 d D . . . . H2AW H 0.402(5) 0.611(5) 0.5420(18) 0.075 Uiso 1 1 d D U . . . H2BW H 0.485(5) 0.592(4) 0.446(3) 0.075 Uiso 1 1 d D U . . . Cl1 Cl 0.55079(9) 0.00524(9) 0.68395(6) 0.0311(2) Uani 1 1 d . . . . . O11A O 0.5412(8) -0.0860(5) 0.7696(5) 0.049(2) Uani 0.581(16) 1 d . . P . . O12A O 0.6784(8) 0.0157(12) 0.6772(5) 0.046(2) Uani 0.581(16) 1 d . . P . . O13A O 0.4501(10) 0.1264(7) 0.6941(5) 0.045(2) Uani 0.581(16) 1 d . . P . . O11B O 0.6237(16) -0.1119(10) 0.7339(7) 0.061(5) Uani 0.419(16) 1 d . . P . . O12B O 0.6343(12) 0.0852(12) 0.6489(6) 0.041(2) Uani 0.419(16) 1 d . . P . . O13B O 0.4309(12) 0.066(2) 0.7136(11) 0.083(5) Uani 0.419(16) 1 d . . P . . Cl02 Cl 0.92339(8) 0.54811(8) 0.79931(5) 0.0253(2) 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 0.0308(14) 0.0287(13) 0.0272(13) -0.0050(10) -0.0012(10) -0.0169(11) N4 0.0198(14) 0.0211(14) 0.0176(14) -0.0031(11) -0.0041(11) -0.0075(11) N2' 0.0227(14) 0.0248(15) 0.0195(14) -0.0053(11) -0.0037(11) -0.0109(12) O2' 0.0385(15) 0.0503(17) 0.0214(13) -0.0127(12) 0.0026(11) -0.0276(13) O2 0.0352(14) 0.0356(14) 0.0238(13) -0.0075(11) -0.0008(10) -0.0220(12) N3' 0.0294(16) 0.0306(17) 0.0286(16) -0.0085(13) 0.0004(13) -0.0148(13) N2 0.0236(15) 0.0254(15) 0.0236(15) -0.0030(12) -0.0048(12) -0.0128(12) O22 0.0342(15) 0.0562(18) 0.0288(14) -0.0117(13) 0.0027(11) -0.0282(13) N3 0.0246(15) 0.0273(15) 0.0217(15) -0.0081(12) 0.0024(11) -0.0113(12) N1' 0.0276(16) 0.0282(16) 0.0271(16) -0.0065(12) 0.0000(12) -0.0137(13) N4' 0.0253(15) 0.0237(15) 0.0227(15) -0.0037(12) -0.0020(12) -0.0113(12) N1 0.0268(15) 0.0288(16) 0.0213(15) -0.0066(12) -0.0001(12) -0.0146(13) C8' 0.0211(16) 0.0210(17) 0.0204(17) -0.0014(13) -0.0005(13) -0.0092(13) C9' 0.0229(18) 0.0319(19) 0.0239(18) -0.0077(15) 0.0005(14) -0.0110(15) C6' 0.0292(19) 0.0294(19) 0.0304(19) -0.0112(15) 0.0017(15) -0.0150(15) C9 0.0246(17) 0.0260(17) 0.0168(16) -0.0048(13) 0.0006(13) -0.0101(14) O1' 0.0376(14) 0.0352(14) 0.0230(13) -0.0022(11) -0.0047(11) -0.0226(12) C7 0.0208(17) 0.0243(18) 0.0275(18) -0.0060(14) -0.0036(14) -0.0080(14) C15 0.0249(18) 0.0269(18) 0.0249(18) -0.0047(14) -0.0027(14) -0.0106(14) C8 0.0211(16) 0.0196(16) 0.0201(17) -0.0018(13) -0.0005(13) -0.0072(13) C10' 0.0271(18) 0.0212(17) 0.0311(19) -0.0001(14) -0.0078(15) -0.0139(14) C5' 0.0254(18) 0.0202(17) 0.0291(19) -0.0041(14) -0.0026(14) -0.0099(14) C10 0.0221(17) 0.0199(16) 0.0270(18) -0.0089(14) -0.0040(14) -0.0060(13) C11 0.033(2) 0.034(2) 0.0253(19) -0.0079(15) -0.0012(15) -0.0174(16) O23 0.059(2) 0.0433(18) 0.073(2) -0.0331(17) 0.0198(17) -0.0288(16) C2' 0.0302(19) 0.041(2) 0.0212(18) -0.0023(16) -0.0051(15) -0.0162(17) C14 0.0231(18) 0.0278(19) 0.035(2) -0.0066(15) -0.0030(15) -0.0096(15) C1' 0.0281(19) 0.041(2) 0.0174(17) -0.0075(15) 0.0006(14) -0.0196(16) C7' 0.0264(18) 0.0208(17) 0.0236(18) -0.0048(13) -0.0022(14) -0.0096(14) C6 0.0234(18) 0.0256(19) 0.048(2) -0.0124(17) -0.0041(16) -0.0085(15) C1 0.034(2) 0.037(2) 0.0229(18) 0.0000(15) -0.0089(15) -0.0193(17) C12 0.040(2) 0.038(2) 0.0264(19) -0.0104(16) -0.0079(16) -0.0161(18) C13 0.030(2) 0.0282(19) 0.041(2) -0.0104(16) -0.0103(16) -0.0108(16) O24 0.050(2) 0.060(2) 0.065(2) 0.0145(18) -0.0280(17) -0.0138(17) C15' 0.034(2) 0.049(2) 0.036(2) -0.0024(18) -0.0051(17) -0.0252(19) C3' 0.053(2) 0.044(2) 0.0198(18) 0.0012(16) -0.0069(17) -0.033(2) C11' 0.034(2) 0.042(2) 0.042(2) -0.0168(19) -0.0019(17) -0.0194(18) C5 0.031(2) 0.038(2) 0.039(2) -0.0159(17) 0.0021(16) -0.0159(17) C2 0.035(2) 0.034(2) 0.033(2) 0.0000(16) -0.0078(16) -0.0167(17) C13' 0.037(2) 0.029(2) 0.050(3) -0.0030(18) -0.0174(19) -0.0154(17) C3 0.039(2) 0.0256(19) 0.031(2) -0.0008(15) -0.0038(16) -0.0162(16) C4 0.043(2) 0.040(2) 0.0220(19) -0.0058(16) -0.0020(16) -0.0252(18) O11 0.0362(16) 0.0469(17) 0.0551(19) -0.0274(15) -0.0085(13) -0.0102(13) C4' 0.052(3) 0.059(3) 0.0182(18) -0.0089(17) 0.0066(17) -0.039(2) C12' 0.040(2) 0.052(3) 0.046(2) -0.022(2) -0.0046(19) -0.020(2) C14' 0.035(2) 0.044(2) 0.043(2) 0.0038(19) -0.0099(18) -0.0246(19) O21 0.0331(15) 0.081(2) 0.0292(15) -0.0223(15) 0.0093(12) -0.0207(15) O1W 0.0314(15) 0.0286(15) 0.0571(19) -0.0071(13) -0.0081(13) -0.0067(12) O2W 0.0365(17) 0.086(3) 0.0361(17) -0.0239(17) 0.0036(13) -0.0253(17) Cl1 0.0286(5) 0.0331(5) 0.0318(5) -0.0051(4) -0.0039(4) -0.0127(4) O11A 0.045(4) 0.037(3) 0.042(4) 0.013(2) 0.003(3) -0.010(3) O12A 0.042(4) 0.084(7) 0.036(4) -0.025(4) 0.006(3) -0.044(4) O13A 0.060(5) 0.031(3) 0.034(3) -0.013(3) -0.014(3) 0.005(3) O11B 0.095(11) 0.059(6) 0.038(6) 0.015(4) -0.027(6) -0.047(6) O12B 0.054(6) 0.042(6) 0.033(5) 0.002(4) -0.005(4) -0.032(5) O13B 0.042(5) 0.144(16) 0.086(10) -0.083(11) 0.030(6) -0.029(9) Cl02 0.0237(4) 0.0328(5) 0.0223(4) -0.0089(3) -0.0011(3) -0.0117(3) _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 C2 1.412(4) . ? O1 C3 1.434(4) . ? N4 C9 1.346(4) . ? N4 N3 1.352(4) . ? N4 C10 1.431(4) . ? N2' C5' 1.492(4) . ? N2' C1' 1.515(4) . ? N2' C7' 1.518(4) . ? N2' H1' 1.0000 . ? O2' C6' 1.415(4) . ? O2' C4' 1.426(4) 2_666 ? O2 C5 1.431(4) . ? O2 C4 1.440(4) . ? N3' N1' 1.307(4) . ? N3' N4' 1.355(4) . ? N2 C7 1.509(4) . ? N2 C6 1.511(5) . ? N2 C1 1.512(4) . ? N2 H1 1.0000 . ? O22 Cl02 1.436(3) . ? N3 N1 1.311(4) . ? N1' C8' 1.367(4) . ? N4' C9' 1.350(4) . ? N4' C10' 1.439(4) . ? N1 C8 1.367(4) . ? C8' C9' 1.364(5) . ? C8' C7' 1.484(5) . ? C9' H9' 0.9500 . ? C6' C5' 1.499(5) . ? C6' H6'1 0.9900 . ? C6' H6'2 0.9900 . ? C9 C8 1.362(5) . ? C9 H9 0.9500 . ? O1' C2' 1.416(4) . ? O1' C3' 1.433(4) . ? C7 C8 1.491(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C15 C10 1.387(5) . ? C15 C14 1.391(5) . ? C15 H15 0.9500 . ? C10' C11' 1.384(5) . ? C10' C15' 1.385(5) . ? C5' H5'1 0.9900 . ? C5' H5'2 0.9900 . ? C10 C11 1.386(5) . ? C11 C12 1.383(5) . ? C11 H11 0.9500 . ? O23 Cl02 1.436(3) . ? C2' C1' 1.510(5) . ? C2' H2'1 0.9900 . ? C2' H2'2 0.9900 . ? C14 C13 1.381(5) . ? C14 H14 0.9500 . ? C1' H1'1 0.9900 . ? C1' H1'2 0.9900 . ? C7' H7'1 0.9900 . ? C7' H7'2 0.9900 . ? C6 C5 1.503(5) 2_757 ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C1 C2 1.512(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C12 C13 1.380(5) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? O24 Cl02 1.412(3) . ? C15' C14' 1.392(6) . ? C15' H15' 0.9500 . ? C3' C4' 1.499(6) . ? C3' H3'1 0.9900 . ? C3' H3'2 0.9900 . ? C11' C12' 1.383(5) . ? C11' H11' 0.9500 . ? C5 C6 1.503(5) 2_757 ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C13' C14' 1.374(6) . ? C13' C12' 1.385(6) . ? C13' H13' 0.9500 . ? C3 C4 1.492(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? O11 Cl1 1.437(3) . ? C4' O2' 1.426(4) 2_666 ? C4' H4'1 0.9900 . ? C4' H4'2 0.9900 . ? C12' H12' 0.9500 . ? C14' H14' 0.9500 . ? O21 Cl02 1.429(3) . ? O1W H1AW 0.974(19) . ? O1W H1BW 0.960(19) . ? O2W H2AW 0.983(19) . ? O2W H2BW 0.988(19) . ? Cl1 O13B 1.329(12) . ? Cl1 O11B 1.376(10) . ? Cl1 O12A 1.422(6) . ? Cl1 O12B 1.454(8) . ? Cl1 O13A 1.471(7) . ? Cl1 O11A 1.484(7) . ? O11A O11B 0.984(13) . ? O11A O13B 1.80(2) . ? O12A O12B 0.811(8) . ? O12A O11B 1.731(11) . ? O13A O13B 0.756(17) . ? 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 C2 O1 C3 113.4(3) . . ? C9 N4 N3 110.6(3) . . ? C9 N4 C10 129.2(3) . . ? N3 N4 C10 120.2(3) . . ? C5' N2' C1' 111.9(3) . . ? C5' N2' C7' 113.6(3) . . ? C1' N2' C7' 109.6(3) . . ? C5' N2' H1' 107.1 . . ? C1' N2' H1' 107.1 . . ? C7' N2' H1' 107.1 . . ? C6' O2' C4' 113.4(3) . 2_666 ? C5 O2 C4 113.6(3) . . ? N1' N3' N4' 107.4(3) . . ? C7 N2 C6 113.3(3) . . ? C7 N2 C1 110.8(3) . . ? C6 N2 C1 110.5(3) . . ? C7 N2 H1 107.3 . . ? C6 N2 H1 107.3 . . ? C1 N2 H1 107.3 . . ? N1 N3 N4 107.1(3) . . ? N3' N1' C8' 108.8(3) . . ? C9' N4' N3' 110.4(3) . . ? C9' N4' C10' 128.7(3) . . ? N3' N4' C10' 120.9(3) . . ? N3 N1 C8 108.9(3) . . ? C9' C8' N1' 108.5(3) . . ? C9' C8' C7' 129.8(3) . . ? N1' C8' C7' 121.7(3) . . ? N4' C9' C8' 104.9(3) . . ? N4' C9' H9' 127.6 . . ? C8' C9' H9' 127.6 . . ? O2' C6' C5' 108.1(3) . . ? O2' C6' H6'1 110.1 . . ? C5' C6' H6'1 110.1 . . ? O2' C6' H6'2 110.1 . . ? C5' C6' H6'2 110.1 . . ? H6'1 C6' H6'2 108.4 . . ? N4 C9 C8 105.2(3) . . ? N4 C9 H9 127.4 . . ? C8 C9 H9 127.4 . . ? C2' O1' C3' 112.4(3) . . ? C8 C7 N2 114.1(3) . . ? C8 C7 H7A 108.7 . . ? N2 C7 H7A 108.7 . . ? C8 C7 H7B 108.7 . . ? N2 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C10 C15 C14 119.7(3) . . ? C10 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C9 C8 N1 108.2(3) . . ? C9 C8 C7 129.8(3) . . ? N1 C8 C7 121.9(3) . . ? C11' C10' C15' 121.6(3) . . ? C11' C10' N4' 119.4(3) . . ? C15' C10' N4' 119.0(3) . . ? N2' C5' C6' 113.2(3) . . ? N2' C5' H5'1 108.9 . . ? C6' C5' H5'1 108.9 . . ? N2' C5' H5'2 108.9 . . ? C6' C5' H5'2 108.9 . . ? H5'1 C5' H5'2 107.7 . . ? C11 C10 C15 120.6(3) . . ? C11 C10 N4 119.4(3) . . ? C15 C10 N4 120.0(3) . . ? C12 C11 C10 118.8(3) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? O1' C2' C1' 108.0(3) . . ? O1' C2' H2'1 110.1 . . ? C1' C2' H2'1 110.1 . . ? O1' C2' H2'2 110.1 . . ? C1' C2' H2'2 110.1 . . ? H2'1 C2' H2'2 108.4 . . ? C13 C14 C15 119.9(3) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C2' C1' N2' 112.2(3) . . ? C2' C1' H1'1 109.2 . . ? N2' C1' H1'1 109.2 . . ? C2' C1' H1'2 109.2 . . ? N2' C1' H1'2 109.2 . . ? H1'1 C1' H1'2 107.9 . . ? C8' C7' N2' 113.6(3) . . ? C8' C7' H7'1 108.8 . . ? N2' C7' H7'1 108.8 . . ? C8' C7' H7'2 108.8 . . ? N2' C7' H7'2 108.8 . . ? H7'1 C7' H7'2 107.7 . . ? C5 C6 N2 113.7(3) 2_757 . ? C5 C6 H6A 108.8 2_757 . ? N2 C6 H6A 108.8 . . ? C5 C6 H6B 108.8 2_757 . ? N2 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? N2 C1 C2 113.9(3) . . ? N2 C1 H1A 108.8 . . ? C2 C1 H1A 108.8 . . ? N2 C1 H1B 108.8 . . ? C2 C1 H1B 108.8 . . ? H1A C1 H1B 107.7 . . ? C13 C12 C11 121.1(4) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 119.8(3) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C10' C15' C14' 118.1(4) . . ? C10' C15' H15' 121.0 . . ? C14' C15' H15' 121.0 . . ? O1' C3' C4' 108.1(3) . . ? O1' C3' H3'1 110.1 . . ? C4' C3' H3'1 110.1 . . ? O1' C3' H3'2 110.1 . . ? C4' C3' H3'2 110.1 . . ? H3'1 C3' H3'2 108.4 . . ? C12' C11' C10' 118.9(4) . . ? C12' C11' H11' 120.5 . . ? C10' C11' H11' 120.5 . . ? O2 C5 C6 107.9(3) . 2_757 ? O2 C5 H5A 110.1 . . ? C6 C5 H5A 110.1 2_757 . ? O2 C5 H5B 110.1 . . ? C6 C5 H5B 110.1 2_757 . ? H5A C5 H5B 108.4 . . ? O1 C2 C1 107.6(3) . . ? O1 C2 H2A 110.2 . . ? C1 C2 H2A 110.2 . . ? O1 C2 H2B 110.2 . . ? C1 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? C14' C13' C12' 119.6(4) . . ? C14' C13' H13' 120.2 . . ? C12' C13' H13' 120.2 . . ? O1 C3 C4 108.0(3) . . ? O1 C3 H3A 110.1 . . ? C4 C3 H3A 110.1 . . ? O1 C3 H3B 110.1 . . ? C4 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? O2 C4 C3 108.6(3) . . ? O2 C4 H4A 110.0 . . ? C3 C4 H4A 110.0 . . ? O2 C4 H4B 110.0 . . ? C3 C4 H4B 110.0 . . ? H4A C4 H4B 108.4 . . ? O2' C4' C3' 107.5(3) 2_666 . ? O2' C4' H4'1 110.2 2_666 . ? C3' C4' H4'1 110.2 . . ? O2' C4' H4'2 110.2 2_666 . ? C3' C4' H4'2 110.2 . . ? H4'1 C4' H4'2 108.5 . . ? C11' C12' C13' 120.6(4) . . ? C11' C12' H12' 119.7 . . ? C13' C12' H12' 119.7 . . ? C13' C14' C15' 121.2(4) . . ? C13' C14' H14' 119.4 . . ? C15' C14' H14' 119.4 . . ? H1AW O1W H1BW 120(3) . . ? H2AW O2W H2BW 119(4) . . ? O13B Cl1 O11B 119.4(8) . . ? O13B Cl1 O12A 135.4(7) . . ? O11B Cl1 O12A 76.4(5) . . ? O13B Cl1 O11 104.5(6) . . ? O11B Cl1 O11 102.2(5) . . ? O12A Cl1 O11 112.6(3) . . ? O13B Cl1 O12B 114.3(8) . . ? O11B Cl1 O12B 109.1(5) . . ? O12A Cl1 O12B 32.7(3) . . ? O11 Cl1 O12B 105.6(4) . . ? O13B Cl1 O13A 30.8(8) . . ? O11B Cl1 O13A 139.5(7) . . ? O12A Cl1 O13A 109.3(4) . . ? O11 Cl1 O13A 111.2(3) . . ? O12B Cl1 O13A 83.7(5) . . ? O13B Cl1 O11A 79.3(9) . . ? O11B Cl1 O11A 40.0(5) . . ? O12A Cl1 O11A 104.6(4) . . ? O11 Cl1 O11A 115.7(3) . . ? O12B Cl1 O11A 131.7(5) . . ? O13A Cl1 O11A 102.7(4) . . ? O11B O11A Cl1 64.0(7) . . ? O11B O11A O13B 110.5(9) . . ? Cl1 O11A O13B 46.5(4) . . ? O12B O12A Cl1 75.8(8) . . ? O12B O12A O11B 126.4(10) . . ? Cl1 O12A O11B 50.6(4) . . ? O13B O13A Cl1 64.2(13) . . ? O11A O11B Cl1 75.9(10) . . ? O11A O11B O12A 112.9(11) . . ? Cl1 O11B O12A 53.0(4) . . ? O12A O12B Cl1 71.5(8) . . ? O13A O13B Cl1 85.0(14) . . ? O13A O13B O11A 123.8(18) . . ? Cl1 O13B O11A 54.2(6) . . ? O24 Cl02 O21 110.0(2) . . ? O24 Cl02 O22 110.29(19) . . ? O21 Cl02 O22 109.69(17) . . ? O24 Cl02 O23 108.5(2) . . ? O21 Cl02 O23 108.8(2) . . ? O22 Cl02 O23 109.55(18) . . ? 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 N4 N3 N1 0.0(4) . . . . ? C10 N4 N3 N1 179.3(3) . . . . ? N4' N3' N1' C8' 0.1(4) . . . . ? N1' N3' N4' C9' -0.1(4) . . . . ? N1' N3' N4' C10' 179.5(3) . . . . ? N4 N3 N1 C8 -0.4(3) . . . . ? N3' N1' C8' C9' -0.1(4) . . . . ? N3' N1' C8' C7' 177.2(3) . . . . ? N3' N4' C9' C8' 0.1(4) . . . . ? C10' N4' C9' C8' -179.5(3) . . . . ? N1' C8' C9' N4' 0.0(4) . . . . ? C7' C8' C9' N4' -177.0(3) . . . . ? C4' O2' C6' C5' 179.4(3) 2_666 . . . ? N3 N4 C9 C8 0.5(4) . . . . ? C10 N4 C9 C8 -178.8(3) . . . . ? C6 N2 C7 C8 60.6(4) . . . . ? C1 N2 C7 C8 -64.3(4) . . . . ? N4 C9 C8 N1 -0.7(4) . . . . ? N4 C9 C8 C7 176.1(3) . . . . ? N3 N1 C8 C9 0.8(4) . . . . ? N3 N1 C8 C7 -176.4(3) . . . . ? N2 C7 C8 C9 93.9(4) . . . . ? N2 C7 C8 N1 -89.6(4) . . . . ? C9' N4' C10' C11' 10.4(5) . . . . ? N3' N4' C10' C11' -169.2(3) . . . . ? C9' N4' C10' C15' -168.3(4) . . . . ? N3' N4' C10' C15' 12.1(5) . . . . ? C1' N2' C5' C6' -176.9(3) . . . . ? C7' N2' C5' C6' -52.1(4) . . . . ? O2' C6' C5' N2' -56.1(4) . . . . ? C14 C15 C10 C11 -0.4(5) . . . . ? C14 C15 C10 N4 -179.9(3) . . . . ? C9 N4 C10 C11 -18.4(5) . . . . ? N3 N4 C10 C11 162.3(3) . . . . ? C9 N4 C10 C15 161.0(3) . . . . ? N3 N4 C10 C15 -18.2(5) . . . . ? C15 C10 C11 C12 -0.9(5) . . . . ? N4 C10 C11 C12 178.6(3) . . . . ? C3' O1' C2' C1' 180.0(3) . . . . ? C10 C15 C14 C13 1.4(5) . . . . ? O1' C2' C1' N2' -59.7(4) . . . . ? C5' N2' C1' C2' -65.6(4) . . . . ? C7' N2' C1' C2' 167.4(3) . . . . ? C9' C8' C7' N2' -87.1(4) . . . . ? N1' C8' C7' N2' 96.3(4) . . . . ? C5' N2' C7' C8' -55.1(4) . . . . ? C1' N2' C7' C8' 71.0(3) . . . . ? C7 N2 C6 C5 49.6(4) . . . 2_757 ? C1 N2 C6 C5 174.7(3) . . . 2_757 ? C7 N2 C1 C2 -167.7(3) . . . . ? C6 N2 C1 C2 65.8(4) . . . . ? C10 C11 C12 C13 1.3(6) . . . . ? C11 C12 C13 C14 -0.3(6) . . . . ? C15 C14 C13 C12 -1.0(5) . . . . ? C11' C10' C15' C14' 1.3(6) . . . . ? N4' C10' C15' C14' 180.0(3) . . . . ? C2' O1' C3' C4' 172.4(3) . . . . ? C15' C10' C11' C12' -0.2(6) . . . . ? N4' C10' C11' C12' -178.9(3) . . . . ? C4 O2 C5 C6 175.7(3) . . . 2_757 ? C3 O1 C2 C1 -176.3(3) . . . . ? N2 C1 C2 O1 61.9(4) . . . . ? C2 O1 C3 C4 -179.0(3) . . . . ? C5 O2 C4 C3 -176.1(3) . . . . ? O1 C3 C4 O2 -58.3(4) . . . . ? O1' C3' C4' O2' 61.9(4) . . . 2_666 ? C10' C11' C12' C13' -0.7(6) . . . . ? C14' C13' C12' C11' 0.4(6) . . . . ? C12' C13' C14' C15' 0.8(6) . . . . ? C10' C15' C14' C13' -1.6(6) . . . . ? O13B Cl1 O11A O11B 179.1(10) . . . . ? O12A Cl1 O11A O11B -46.5(8) . . . . ? O11 Cl1 O11A O11B 78.0(7) . . . . ? O12B Cl1 O11A O11B -67.8(9) . . . . ? O13A Cl1 O11A O11B -160.7(7) . . . . ? O11B Cl1 O11A O13B -179.1(10) . . . . ? O12A Cl1 O11A O13B 134.4(7) . . . . ? O11 Cl1 O11A O13B -101.1(7) . . . . ? O12B Cl1 O11A O13B 113.1(8) . . . . ? O13A Cl1 O11A O13B 20.2(7) . . . . ? O13B Cl1 O12A O12B -60.3(15) . . . . ? O11B Cl1 O12A O12B -178.5(11) . . . . ? O11 Cl1 O12A O12B 83.7(10) . . . . ? O13A Cl1 O12A O12B -40.5(10) . . . . ? O11A Cl1 O12A O12B -149.8(9) . . . . ? O13B Cl1 O12A O11B 118.3(11) . . . . ? O11 Cl1 O12A O11B -97.8(5) . . . . ? O12B Cl1 O12A O11B 178.5(11) . . . . ? O13A Cl1 O12A O11B 138.1(7) . . . . ? O11A Cl1 O12A O11B 28.7(6) . . . . ? O11B Cl1 O13A O13B -60.7(19) . . . . ? O12A Cl1 O13A O13B -152.3(15) . . . . ? O11 Cl1 O13A O13B 82.8(16) . . . . ? O12B Cl1 O13A O13B -173.0(16) . . . . ? O11A Cl1 O13A O13B -41.6(17) . . . . ? O13B O11A O11B Cl1 0.7(8) . . . . ? Cl1 O11A O11B O12A 38.8(5) . . . . ? O13B O11A O11B O12A 39.5(10) . . . . ? O13B Cl1 O11B O11A -1.1(11) . . . . ? O12A Cl1 O11B O11A 133.7(7) . . . . ? O11 Cl1 O11B O11A -115.6(6) . . . . ? O12B Cl1 O11B O11A 132.9(7) . . . . ? O13A Cl1 O11B O11A 29.8(11) . . . . ? O13B Cl1 O11B O12A -134.8(8) . . . . ? O11 Cl1 O11B O12A 110.6(3) . . . . ? O12B Cl1 O11B O12A -0.8(7) . . . . ? O13A Cl1 O11B O12A -104.0(7) . . . . ? O11A Cl1 O11B O12A -133.7(7) . . . . ? O12B O12A O11B O11A -47.8(16) . . . . ? Cl1 O12A O11B O11A -49.5(9) . . . . ? O12B O12A O11B Cl1 1.8(14) . . . . ? O11B O12A O12B Cl1 -1.4(11) . . . . ? O13B Cl1 O12B O12A 138.0(11) . . . . ? O11B Cl1 O12B O12A 1.5(12) . . . . ? O11 Cl1 O12B O12A -107.7(9) . . . . ? O13A Cl1 O12B O12A 142.0(9) . . . . ? O11A Cl1 O12B O12A 40.6(12) . . . . ? Cl1 O13A O13B O11A 40.0(11) . . . . ? O11B Cl1 O13B O13A 139.4(15) . . . . ? O12A Cl1 O13B O13A 39(2) . . . . ? O11 Cl1 O13B O13A -107.2(14) . . . . ? O12B Cl1 O13B O13A 7.7(18) . . . . ? O11A Cl1 O13B O13A 138.8(16) . . . . ? O11B Cl1 O13B O11A 0.7(7) . . . . ? O12A Cl1 O13B O11A -100.1(9) . . . . ? O11 Cl1 O13B O11A 114.1(4) . . . . ? O12B Cl1 O13B O11A -131.1(5) . . . . ? O13A Cl1 O13B O11A -138.8(16) . . . . ? O11B O11A O13B O13A -53(2) . . . . ? Cl1 O11A O13B O13A -52.2(18) . . . . ? O11B O11A O13B Cl1 -0.9(9) . . . . ? _refine_diff_density_max 0.743 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.080 _shelxl_version_number 2013-2 _database_code_depnum_ccdc_archive 'CCDC 851240'