# 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_aaa _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H17 Cl N4 O' _chemical_formula_weight 376.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.921(2) _cell_length_b 11.098(2) _cell_length_c 17.289(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.50(3) _cell_angle_gamma 90.00 _cell_volume 1887.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 836 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 25.5 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9572 _exptl_absorpt_correction_T_max 0.9740 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 18344 _diffrn_reflns_av_R_equivalents 0.0646 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _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 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4323 _reflns_number_gt 3019 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+0.9294P] 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 4323 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1255 _refine_ls_R_factor_gt 0.0837 _refine_ls_wR_factor_ref 0.1722 _refine_ls_wR_factor_gt 0.1561 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.166 _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 Cl1 Cl 0.27942(9) 0.17341(9) 0.12161(6) 0.0763(4) Uani 1 1 d . . . N3 N 0.8368(2) 0.5178(2) 0.08821(13) 0.0421(6) Uani 1 1 d . . . C1 C 1.1702(3) 0.4818(2) 0.20332(15) 0.0371(6) Uani 1 1 d . . . N2 N 1.3822(2) 0.5898(2) 0.20070(14) 0.0446(6) Uani 1 1 d . . . C2 C 0.9733(3) 0.5450(2) 0.10850(15) 0.0377(6) Uani 1 1 d . . . N4 N 0.9270(2) 0.4014(2) 0.18835(13) 0.0410(6) Uani 1 1 d . . . H4A H 0.9324 0.3480 0.2247 0.049 Uiso 1 1 calc R . . C3 C 1.1914(3) 0.6462(2) 0.10567(15) 0.0385(6) Uani 1 1 d . . . N1 N 1.2755(2) 0.7270(2) 0.07707(14) 0.0478(6) Uani 1 1 d . . . C4 C 1.0302(3) 0.4738(2) 0.16978(16) 0.0381(6) Uani 1 1 d . . . C5 C 1.2500(3) 0.5705(2) 0.17176(15) 0.0381(6) Uani 1 1 d . . . C6 C 1.0025(3) 0.7078(3) 0.01163(18) 0.0504(8) Uani 1 1 d . . . H6A H 0.9122 0.7020 -0.0106 0.061 Uiso 1 1 calc R . . C7 C 0.6815(3) 0.3688(3) 0.13718(16) 0.0408(7) Uani 1 1 d . . . C8 C 1.0529(3) 0.6331(2) 0.07407(15) 0.0381(6) Uani 1 1 d . . . C9 C 0.8131(3) 0.4305(2) 0.13762(16) 0.0396(6) Uani 1 1 d . . . C10 C 1.4365(3) 0.5194(3) 0.25875(18) 0.0514(8) Uani 1 1 d . . . H10A H 1.5272 0.5320 0.2784 0.062 Uiso 1 1 calc R . . C11 C 0.4435(3) 0.3535(3) 0.08431(17) 0.0476(7) Uani 1 1 d . . . H11A H 0.3683 0.3829 0.0521 0.057 Uiso 1 1 calc R . . C12 C 0.6679(3) 0.2652(3) 0.18095(19) 0.0546(8) Uani 1 1 d . . . H12A H 0.7425 0.2355 0.2135 0.065 Uiso 1 1 calc R . . C13 C 1.3674(3) 0.4281(3) 0.29218(18) 0.0524(8) Uani 1 1 d . . . H13A H 1.4112 0.3809 0.3322 0.063 Uiso 1 1 calc R . . C14 C 0.4335(3) 0.2509(3) 0.12780(17) 0.0479(7) Uani 1 1 d . . . C15 C 1.2329(3) 0.4094(3) 0.26464(17) 0.0452(7) Uani 1 1 d . . . H15A H 1.1837 0.3496 0.2862 0.054 Uiso 1 1 calc R . . C16 C 0.5679(3) 0.4124(3) 0.08935(17) 0.0464(7) Uani 1 1 d . . . H16A H 0.5755 0.4821 0.0603 0.056 Uiso 1 1 calc R . . C17 C 1.0878(3) 0.7896(3) -0.01633(19) 0.0587(9) Uani 1 1 d . . . H17A H 1.0561 0.8403 -0.0575 0.070 Uiso 1 1 calc R . . C18 C 1.2228(3) 0.7954(3) 0.01808(19) 0.0584(9) Uani 1 1 d . . . H18A H 1.2795 0.8510 -0.0017 0.070 Uiso 1 1 calc R . . C19 C 0.5442(3) 0.2061(3) 0.1764(2) 0.0579(9) Uani 1 1 d . . . H19A H 0.5355 0.1369 0.2057 0.069 Uiso 1 1 calc R . . O1 O 0.9309(2) 0.2679(2) 0.32503(14) 0.0683(7) Uani 1 1 d . . . H1A H 1.0012 0.2287 0.3346 0.103 Uiso 1 1 calc R . . C21 C 0.8952(5) 0.3160(6) 0.3942(3) 0.135(2) Uani 1 1 d . . . H21A H 0.9707 0.3640 0.4188 0.162 Uiso 1 1 calc R . . H21B H 0.8821 0.2500 0.4293 0.162 Uiso 1 1 calc R . . C20 C 0.7776(6) 0.3880(6) 0.3858(3) 0.138(2) Uani 1 1 d . . . H20A H 0.7601 0.4156 0.4362 0.207 Uiso 1 1 calc R . . H20B H 0.7016 0.3416 0.3622 0.207 Uiso 1 1 calc R . . H20C H 0.7908 0.4562 0.3534 0.207 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0554(5) 0.0875(7) 0.0811(7) 0.0293(5) -0.0099(4) -0.0294(5) N3 0.0373(13) 0.0453(14) 0.0426(13) 0.0017(11) 0.0008(10) -0.0005(11) C1 0.0385(15) 0.0346(14) 0.0381(15) -0.0034(12) 0.0045(11) 0.0031(12) N2 0.0350(13) 0.0479(14) 0.0495(14) -0.0008(12) 0.0008(11) -0.0004(11) C2 0.0369(15) 0.0389(15) 0.0370(15) -0.0010(12) 0.0038(12) 0.0009(12) N4 0.0390(13) 0.0416(13) 0.0413(13) 0.0076(11) 0.0014(10) -0.0012(11) C3 0.0423(16) 0.0374(15) 0.0360(15) -0.0053(12) 0.0060(12) -0.0020(12) N1 0.0499(15) 0.0498(15) 0.0441(14) 0.0016(12) 0.0072(11) -0.0088(12) C4 0.0376(15) 0.0366(15) 0.0399(15) -0.0024(12) 0.0037(12) 0.0019(12) C5 0.0362(14) 0.0384(15) 0.0392(15) -0.0062(12) 0.0034(12) 0.0015(12) C6 0.0463(17) 0.0564(19) 0.0464(18) 0.0072(15) -0.0025(14) 0.0001(15) C7 0.0345(15) 0.0453(16) 0.0424(16) 0.0000(13) 0.0040(12) -0.0032(12) C8 0.0413(15) 0.0384(15) 0.0338(14) -0.0023(12) 0.0018(12) 0.0010(12) C9 0.0365(15) 0.0424(16) 0.0395(15) 0.0006(13) 0.0034(12) 0.0014(12) C10 0.0365(16) 0.0554(19) 0.059(2) 0.0003(16) -0.0059(14) 0.0039(14) C11 0.0384(16) 0.0595(19) 0.0432(17) 0.0063(14) -0.0007(13) -0.0040(14) C12 0.0449(18) 0.0548(19) 0.061(2) 0.0151(16) -0.0044(15) 0.0006(15) C13 0.0483(18) 0.0546(19) 0.0520(18) 0.0124(15) -0.0019(14) 0.0074(15) C14 0.0433(17) 0.0548(19) 0.0449(17) 0.0015(15) 0.0034(13) -0.0112(14) C15 0.0441(16) 0.0429(17) 0.0479(17) 0.0067(14) 0.0031(13) 0.0017(14) C16 0.0435(17) 0.0495(18) 0.0453(17) 0.0080(14) 0.0028(13) -0.0043(14) C17 0.068(2) 0.060(2) 0.0464(18) 0.0193(16) -0.0009(16) -0.0048(17) C18 0.064(2) 0.059(2) 0.052(2) 0.0120(16) 0.0053(16) -0.0149(17) C19 0.0500(19) 0.058(2) 0.064(2) 0.0230(17) 0.0007(16) -0.0102(16) O1 0.0545(14) 0.0886(18) 0.0629(15) 0.0282(13) 0.0113(11) 0.0271(13) C21 0.112(4) 0.229(7) 0.064(3) 0.026(4) 0.017(3) 0.089(4) C20 0.151(5) 0.158(5) 0.114(4) 0.004(4) 0.052(4) 0.056(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C14 1.745(3) . ? N3 C9 1.333(3) . ? N3 C2 1.387(3) . ? C1 C15 1.409(4) . ? C1 C5 1.417(4) . ? C1 C4 1.436(4) . ? N2 C10 1.330(4) . ? N2 C5 1.359(3) . ? C2 C4 1.382(4) . ? C2 C8 1.434(4) . ? N4 C4 1.373(3) . ? N4 C9 1.375(3) . ? N4 H4A 0.8600 . ? C3 N1 1.361(3) . ? C3 C8 1.419(4) . ? C3 C5 1.475(4) . ? N1 C18 1.323(4) . ? C6 C17 1.371(4) . ? C6 C8 1.401(4) . ? C6 H6A 0.9300 . ? C7 C12 1.393(4) . ? C7 C16 1.395(4) . ? C7 C9 1.473(4) . ? C10 C13 1.391(4) . ? C10 H10A 0.9300 . ? C11 C14 1.375(4) . ? C11 C16 1.389(4) . ? C11 H11A 0.9300 . ? C12 C19 1.385(4) . ? C12 H12A 0.9300 . ? C13 C15 1.373(4) . ? C13 H13A 0.9300 . ? C14 C19 1.385(4) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 C18 1.395(5) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? O1 C21 1.398(5) . ? O1 H1A 0.8200 . ? C21 C20 1.406(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 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 C9 N3 C2 104.1(2) . . ? C15 C1 C5 118.2(2) . . ? C15 C1 C4 125.3(3) . . ? C5 C1 C4 116.5(2) . . ? C10 N2 C5 117.5(2) . . ? N3 C2 C4 111.0(2) . . ? N3 C2 C8 128.0(2) . . ? C4 C2 C8 121.1(2) . . ? C4 N4 C9 106.8(2) . . ? C4 N4 H4A 126.6 . . ? C9 N4 H4A 126.6 . . ? N1 C3 C8 122.5(2) . . ? N1 C3 C5 117.3(2) . . ? C8 C3 C5 120.3(2) . . ? C18 N1 C3 117.3(3) . . ? N4 C4 C2 105.7(2) . . ? N4 C4 C1 130.8(2) . . ? C2 C4 C1 123.4(2) . . ? N2 C5 C1 121.9(2) . . ? N2 C5 C3 117.3(2) . . ? C1 C5 C3 120.7(2) . . ? C17 C6 C8 119.3(3) . . ? C17 C6 H6A 120.3 . . ? C8 C6 H6A 120.3 . . ? C12 C7 C16 118.7(3) . . ? C12 C7 C9 122.0(3) . . ? C16 C7 C9 119.3(3) . . ? C6 C8 C3 117.8(3) . . ? C6 C8 C2 124.3(3) . . ? C3 C8 C2 117.9(2) . . ? N3 C9 N4 112.4(2) . . ? N3 C9 C7 124.4(2) . . ? N4 C9 C7 123.2(2) . . ? N2 C10 C13 124.7(3) . . ? N2 C10 H10A 117.6 . . ? C13 C10 H10A 117.6 . . ? C14 C11 C16 118.8(3) . . ? C14 C11 H11A 120.6 . . ? C16 C11 H11A 120.6 . . ? C19 C12 C7 120.6(3) . . ? C19 C12 H12A 119.7 . . ? C7 C12 H12A 119.7 . . ? C15 C13 C10 118.4(3) . . ? C15 C13 H13A 120.8 . . ? C10 C13 H13A 120.8 . . ? C11 C14 C19 121.4(3) . . ? C11 C14 Cl1 120.0(2) . . ? C19 C14 Cl1 118.6(2) . . ? C13 C15 C1 119.2(3) . . ? C13 C15 H15A 120.4 . . ? C1 C15 H15A 120.4 . . ? C11 C16 C7 121.1(3) . . ? C11 C16 H16A 119.5 . . ? C7 C16 H16A 119.5 . . ? C6 C17 C18 118.9(3) . . ? C6 C17 H17A 120.6 . . ? C18 C17 H17A 120.6 . . ? N1 C18 C17 124.3(3) . . ? N1 C18 H18A 117.9 . . ? C17 C18 H18A 117.9 . . ? C14 C19 C12 119.4(3) . . ? C14 C19 H19A 120.3 . . ? C12 C19 H19A 120.3 . . ? C21 O1 H1A 109.5 . . ? O1 C21 C20 115.4(4) . . ? O1 C21 H21A 108.4 . . ? C20 C21 H21A 108.4 . . ? O1 C21 H21B 108.4 . . ? C20 C21 H21B 108.4 . . ? H21A C21 H21B 107.5 . . ? C21 C20 H20A 109.5 . . ? C21 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C21 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 C9 N3 C2 C4 0.1(3) . . . . ? C9 N3 C2 C8 -179.9(3) . . . . ? C8 C3 N1 C18 0.7(4) . . . . ? C5 C3 N1 C18 -179.6(3) . . . . ? C9 N4 C4 C2 0.6(3) . . . . ? C9 N4 C4 C1 -179.9(3) . . . . ? N3 C2 C4 N4 -0.4(3) . . . . ? C8 C2 C4 N4 179.6(2) . . . . ? N3 C2 C4 C1 -180.0(2) . . . . ? C8 C2 C4 C1 0.0(4) . . . . ? C15 C1 C4 N4 1.9(5) . . . . ? C5 C1 C4 N4 -177.8(3) . . . . ? C15 C1 C4 C2 -178.6(3) . . . . ? C5 C1 C4 C2 1.7(4) . . . . ? C10 N2 C5 C1 2.1(4) . . . . ? C10 N2 C5 C3 -178.0(2) . . . . ? C15 C1 C5 N2 -2.3(4) . . . . ? C4 C1 C5 N2 177.4(2) . . . . ? C15 C1 C5 C3 177.8(2) . . . . ? C4 C1 C5 C3 -2.5(4) . . . . ? N1 C3 C5 N2 2.0(4) . . . . ? C8 C3 C5 N2 -178.2(2) . . . . ? N1 C3 C5 C1 -178.1(2) . . . . ? C8 C3 C5 C1 1.7(4) . . . . ? C17 C6 C8 C3 0.1(4) . . . . ? C17 C6 C8 C2 179.6(3) . . . . ? N1 C3 C8 C6 -0.6(4) . . . . ? C5 C3 C8 C6 179.6(2) . . . . ? N1 C3 C8 C2 179.9(2) . . . . ? C5 C3 C8 C2 0.1(4) . . . . ? N3 C2 C8 C6 -0.4(5) . . . . ? C4 C2 C8 C6 179.6(3) . . . . ? N3 C2 C8 C3 179.1(3) . . . . ? C4 C2 C8 C3 -1.0(4) . . . . ? C2 N3 C9 N4 0.3(3) . . . . ? C2 N3 C9 C7 -178.0(3) . . . . ? C4 N4 C9 N3 -0.6(3) . . . . ? C4 N4 C9 C7 177.7(2) . . . . ? C12 C7 C9 N3 169.0(3) . . . . ? C16 C7 C9 N3 -8.6(4) . . . . ? C12 C7 C9 N4 -9.1(4) . . . . ? C16 C7 C9 N4 173.4(3) . . . . ? C5 N2 C10 C13 -0.4(5) . . . . ? C16 C7 C12 C19 0.7(5) . . . . ? C9 C7 C12 C19 -176.9(3) . . . . ? N2 C10 C13 C15 -1.0(5) . . . . ? C16 C11 C14 C19 0.3(5) . . . . ? C16 C11 C14 Cl1 -179.0(2) . . . . ? C10 C13 C15 C1 0.7(4) . . . . ? C5 C1 C15 C13 0.8(4) . . . . ? C4 C1 C15 C13 -178.8(3) . . . . ? C14 C11 C16 C7 0.3(4) . . . . ? C12 C7 C16 C11 -0.8(4) . . . . ? C9 C7 C16 C11 176.8(3) . . . . ? C8 C6 C17 C18 0.4(5) . . . . ? C3 N1 C18 C17 -0.2(5) . . . . ? C6 C17 C18 N1 -0.4(6) . . . . ? C11 C14 C19 C12 -0.4(5) . . . . ? Cl1 C14 C19 C12 178.9(3) . . . . ? C7 C12 C19 C14 -0.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.264 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 920155' ####################################################################### # # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H22 Cl Cu N5 O6' _chemical_formula_weight 587.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5860(17) _cell_length_b 11.180(2) _cell_length_c 13.844(3) _cell_angle_alpha 97.13(3) _cell_angle_beta 104.40(3) _cell_angle_gamma 94.66(3) _cell_volume 1268.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 997 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 25.5 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 602 _exptl_absorpt_coefficient_mu 1.017 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.783 _exptl_absorpt_correction_T_max 0.859 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7555 _diffrn_reflns_av_R_equivalents 0.0972 _diffrn_reflns_av_sigmaI/netI 0.1758 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.05 _reflns_number_total 4419 _reflns_number_gt 2222 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1002P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4419 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1818 _refine_ls_R_factor_gt 0.0950 _refine_ls_wR_factor_ref 0.2538 _refine_ls_wR_factor_gt 0.2131 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 0.54737(13) 0.77620(9) 0.25952(8) 0.0495(4) Uani 1 1 d . . . Cl1 Cl 0.9003(3) -0.1009(2) 0.78404(19) 0.0630(8) Uani 1 1 d . . . N1 N 0.4623(8) 0.6095(6) 0.2679(5) 0.0446(18) Uani 1 1 d . . . N2 N 0.7043(8) 0.7529(6) 0.3863(5) 0.0408(17) Uani 1 1 d . . . N3 N 0.6129(8) 0.2954(6) 0.4759(5) 0.0453(18) Uani 1 1 d . . . N4 N 0.8236(8) 0.4188(5) 0.5782(5) 0.0420(17) Uani 1 1 d . . . H4A H 0.9083 0.4433 0.6272 0.050 Uiso 1 1 calc R . . N9 N 0.8517(11) 0.4348(8) 0.2078(7) 0.071(2) Uani 1 1 d . . . C1 C 0.8186(11) 0.8301(8) 0.4419(7) 0.052(2) Uani 1 1 d . . . H1A H 0.8309 0.9076 0.4250 0.063 Uiso 1 1 calc R . . C2 C 0.9285(11) 0.8012(8) 0.5295(7) 0.054(2) Uani 1 1 d . . . H2A H 1.0101 0.8590 0.5700 0.064 Uiso 1 1 calc R . . C3 C 0.9100(10) 0.6860(7) 0.5521(6) 0.043(2) Uani 1 1 d . . . H3B H 0.9814 0.6629 0.6071 0.051 Uiso 1 1 calc R . . C4 C 0.7831(10) 0.6045(7) 0.4914(6) 0.039(2) Uani 1 1 d . . . C5 C 0.6842(10) 0.6406(7) 0.4105(6) 0.039(2) Uani 1 1 d . . . C6 C 0.5517(10) 0.5617(7) 0.3465(6) 0.040(2) Uani 1 1 d . . . C7 C 0.5170(10) 0.4438(7) 0.3606(6) 0.043(2) Uani 1 1 d . . . C8 C 0.3880(11) 0.3726(8) 0.2963(7) 0.053(2) Uani 1 1 d . . . H8A H 0.3613 0.2931 0.3050 0.063 Uiso 1 1 calc R . . C9 C 0.2991(11) 0.4224(9) 0.2183(7) 0.065(3) Uani 1 1 d . . . H9A H 0.2100 0.3757 0.1731 0.077 Uiso 1 1 calc R . . C10 C 0.3386(11) 0.5409(8) 0.2049(7) 0.054(2) Uani 1 1 d . . . H10A H 0.2766 0.5720 0.1506 0.065 Uiso 1 1 calc R . . C11 C 0.6223(10) 0.4054(7) 0.4446(6) 0.042(2) Uani 1 1 d . . . C12 C 0.7514(9) 0.4839(7) 0.5080(6) 0.039(2) Uani 1 1 d . . . C13 C 0.7368(10) 0.3063(7) 0.5570(7) 0.043(2) Uani 1 1 d . . . C14 C 0.7782(10) 0.2091(7) 0.6164(6) 0.039(2) Uani 1 1 d . . . C15 C 0.9190(11) 0.2199(8) 0.6939(7) 0.056(3) Uani 1 1 d . . . H15A H 0.9883 0.2920 0.7113 0.067 Uiso 1 1 calc R . . C16 C 0.9555(10) 0.1240(8) 0.7445(7) 0.054(2) Uani 1 1 d . . . H16A H 1.0512 0.1300 0.7953 0.064 Uiso 1 1 calc R . . C17 C 0.8507(11) 0.0190(7) 0.7202(7) 0.047(2) Uani 1 1 d . . . C18 C 0.7099(11) 0.0059(8) 0.6466(7) 0.051(2) Uani 1 1 d . . . H18A H 0.6400 -0.0658 0.6317 0.061 Uiso 1 1 calc R . . C19 C 0.6731(10) 0.1028(7) 0.5941(7) 0.050(2) Uani 1 1 d . . . H19A H 0.5771 0.0960 0.5436 0.060 Uiso 1 1 calc R . . C20 C 0.6690(11) 1.1380(8) 0.2449(8) 0.066(3) Uani 1 1 d . . . H20A H 0.7575 1.1402 0.3035 0.099 Uiso 1 1 calc R . . H20B H 0.5972 1.1951 0.2595 0.099 Uiso 1 1 calc R . . H20C H 0.7100 1.1590 0.1900 0.099 Uiso 1 1 calc R . . C21 C 0.5786(12) 1.0126(8) 0.2165(7) 0.052(2) Uani 1 1 d . . . C22 C 0.4484(12) 0.9892(8) 0.1354(7) 0.058(3) Uani 1 1 d . . . H22A H 0.4252 1.0502 0.0959 0.069 Uiso 1 1 calc R . . C23 C 0.3487(12) 0.8821(9) 0.1075(7) 0.058(3) Uani 1 1 d . . . C24 C 0.2038(13) 0.8663(9) 0.0220(8) 0.086(4) Uani 1 1 d . . . H24A H 0.1494 0.7858 0.0138 0.129 Uiso 1 1 calc R . . H24B H 0.2351 0.8783 -0.0383 0.129 Uiso 1 1 calc R . . H24C H 0.1323 0.9245 0.0348 0.129 Uiso 1 1 calc R . . C25 C 0.6500(16) 0.7042(14) 0.0448(9) 0.151(7) Uani 1 1 d . . . H25A H 0.7243 0.6659 0.0130 0.226 Uiso 1 1 calc R . . H25B H 0.6541 0.7882 0.0362 0.226 Uiso 1 1 calc R . . H25C H 0.5422 0.6647 0.0145 0.226 Uiso 1 1 calc R . . O1 O 0.6355(7) 0.9384(5) 0.2730(4) 0.0503(15) Uani 1 1 d . . . O2 O 0.3685(7) 0.7884(5) 0.1502(5) 0.0585(17) Uani 1 1 d . . . O3 O 0.6949(8) 0.6949(6) 0.1531(5) 0.0675(19) Uani 1 1 d . . . H7A H 0.7840 0.6557 0.1793 0.081 Uiso 1 1 calc R . . O4 O 0.9255(9) 0.3492(6) 0.2080(6) 0.090(2) Uani 1 1 d . . . O5 O 0.8802(8) 0.5127(7) 0.2816(6) 0.084(2) Uani 1 1 d . . . O6 O 0.7359(15) 0.4388(9) 0.1391(9) 0.178(6) 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 0.0579(8) 0.0446(7) 0.0475(8) 0.0136(5) 0.0123(6) 0.0096(5) Cl1 0.0669(17) 0.0498(14) 0.0730(18) 0.0269(12) 0.0089(14) 0.0133(12) N1 0.050(5) 0.048(4) 0.034(4) 0.006(4) 0.007(4) 0.005(4) N2 0.049(4) 0.037(4) 0.031(4) 0.006(3) 0.001(3) -0.001(3) N3 0.058(5) 0.037(4) 0.041(5) 0.011(3) 0.013(4) 0.003(3) N4 0.048(4) 0.038(4) 0.039(4) 0.009(3) 0.007(3) 0.008(3) N9 0.084(7) 0.065(6) 0.054(6) 0.013(5) -0.008(5) 0.023(5) C1 0.057(6) 0.047(5) 0.049(6) 0.007(5) 0.009(5) -0.002(5) C2 0.052(6) 0.050(5) 0.055(6) 0.001(5) 0.015(5) -0.010(4) C3 0.051(6) 0.049(5) 0.031(5) 0.010(4) 0.013(4) 0.014(4) C4 0.049(5) 0.034(4) 0.032(5) -0.001(4) 0.011(4) -0.001(4) C5 0.047(5) 0.037(5) 0.030(5) -0.001(4) 0.010(4) 0.005(4) C6 0.042(5) 0.051(5) 0.030(5) 0.009(4) 0.011(4) 0.016(4) C7 0.048(5) 0.044(5) 0.037(5) 0.002(4) 0.010(4) 0.007(4) C8 0.060(6) 0.048(5) 0.050(6) 0.017(5) 0.010(5) -0.002(5) C9 0.065(7) 0.062(6) 0.054(7) -0.003(5) 0.002(5) -0.010(5) C10 0.057(6) 0.055(6) 0.050(6) 0.010(5) 0.015(5) 0.003(5) C11 0.042(5) 0.050(5) 0.039(5) 0.008(4) 0.017(4) 0.011(4) C12 0.046(5) 0.036(4) 0.038(5) 0.006(4) 0.019(4) 0.004(4) C13 0.049(5) 0.041(5) 0.044(6) 0.011(4) 0.020(5) 0.009(4) C14 0.041(5) 0.038(5) 0.046(6) 0.006(4) 0.022(4) 0.009(4) C15 0.052(6) 0.045(5) 0.073(7) 0.017(5) 0.019(5) 0.004(4) C16 0.045(6) 0.063(6) 0.050(6) 0.013(5) 0.005(5) 0.010(5) C17 0.057(6) 0.038(5) 0.054(6) 0.018(4) 0.022(5) 0.014(4) C18 0.053(6) 0.045(5) 0.055(6) 0.013(4) 0.012(5) 0.006(4) C19 0.051(6) 0.047(5) 0.049(6) 0.012(4) 0.005(5) 0.005(4) C20 0.073(7) 0.054(6) 0.081(8) 0.025(5) 0.028(6) 0.015(5) C21 0.071(7) 0.043(5) 0.052(6) 0.015(5) 0.027(6) 0.013(5) C22 0.075(7) 0.050(6) 0.048(7) 0.019(5) 0.010(6) 0.009(5) C23 0.075(7) 0.064(7) 0.040(6) 0.012(5) 0.013(5) 0.029(6) C24 0.100(9) 0.084(8) 0.060(8) 0.024(6) -0.012(7) 0.011(7) C25 0.142(13) 0.232(19) 0.069(10) -0.027(10) 0.006(9) 0.114(13) O1 0.056(4) 0.049(3) 0.049(4) 0.019(3) 0.013(3) 0.010(3) O2 0.064(4) 0.054(4) 0.055(4) 0.014(3) 0.006(3) 0.016(3) O3 0.073(5) 0.076(4) 0.061(5) 0.017(4) 0.024(4) 0.026(4) O4 0.091(6) 0.060(5) 0.123(7) 0.015(4) 0.026(5) 0.029(4) O5 0.077(5) 0.067(5) 0.094(6) -0.021(4) 0.016(5) -0.003(4) O6 0.209(12) 0.146(10) 0.124(9) -0.012(7) -0.062(9) 0.086(9) _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 O1 1.876(6) . ? Cu1 O2 1.896(6) . ? Cu1 N1 1.974(7) . ? Cu1 N2 1.990(6) . ? Cu1 O3 2.321(6) . ? Cl1 C17 1.719(8) . ? N1 C10 1.311(11) . ? N1 C6 1.362(10) . ? N2 C1 1.274(10) . ? N2 C5 1.347(9) . ? N3 C13 1.326(10) . ? N3 C11 1.357(10) . ? N4 C12 1.345(9) . ? N4 C13 1.368(10) . ? N4 H4A 0.8600 . ? N9 O4 1.190(9) . ? N9 O6 1.201(11) . ? N9 O5 1.217(10) . ? C1 C2 1.429(11) . ? C1 H1A 0.9300 . ? C2 C3 1.368(10) . ? C2 H2A 0.9300 . ? C3 C4 1.384(11) . ? C3 H3B 0.9300 . ? C4 C5 1.355(11) . ? C4 C12 1.412(10) . ? C5 C6 1.414(11) . ? C6 C7 1.375(11) . ? C7 C8 1.358(11) . ? C7 C11 1.420(11) . ? C8 C9 1.366(12) . ? C8 H8A 0.9300 . ? C9 C10 1.387(11) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C12 1.391(11) . ? C13 C14 1.457(10) . ? C14 C19 1.385(11) . ? C14 C15 1.388(11) . ? C15 C16 1.368(11) . ? C15 H15A 0.9300 . ? C16 C17 1.372(11) . ? C16 H16A 0.9300 . ? C17 C18 1.357(11) . ? C18 C19 1.393(10) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C20 C21 1.503(12) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 O1 1.254(9) . ? C21 C22 1.355(12) . ? C22 C23 1.367(12) . ? C22 H22A 0.9300 . ? C23 O2 1.269(10) . ? C23 C24 1.469(12) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 O3 1.471(13) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? O3 H7A 0.9300 . ? 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 O1 Cu1 O2 94.6(2) . . ? O1 Cu1 N1 171.3(3) . . ? O2 Cu1 N1 91.7(3) . . ? O1 Cu1 N2 91.4(3) . . ? O2 Cu1 N2 169.5(3) . . ? N1 Cu1 N2 81.4(3) . . ? O1 Cu1 O3 96.9(2) . . ? O2 Cu1 O3 92.6(2) . . ? N1 Cu1 O3 88.7(3) . . ? N2 Cu1 O3 95.3(3) . . ? C10 N1 C6 118.5(8) . . ? C10 N1 Cu1 127.6(6) . . ? C6 N1 Cu1 113.7(6) . . ? C1 N2 C5 119.6(7) . . ? C1 N2 Cu1 127.0(6) . . ? C5 N2 Cu1 113.4(5) . . ? C13 N3 C11 103.9(7) . . ? C12 N4 C13 107.0(7) . . ? C12 N4 H4A 126.5 . . ? C13 N4 H4A 126.5 . . ? O4 N9 O6 120.2(11) . . ? O4 N9 O5 120.7(9) . . ? O6 N9 O5 118.6(10) . . ? N2 C1 C2 122.0(8) . . ? N2 C1 H1A 119.0 . . ? C2 C1 H1A 119.0 . . ? C3 C2 C1 118.1(8) . . ? C3 C2 H2A 121.0 . . ? C1 C2 H2A 121.0 . . ? C2 C3 C4 118.8(8) . . ? C2 C3 H3B 120.6 . . ? C4 C3 H3B 120.6 . . ? C5 C4 C3 118.9(7) . . ? C5 C4 C12 117.4(7) . . ? C3 C4 C12 123.7(8) . . ? N2 C5 C4 122.7(7) . . ? N2 C5 C6 116.0(7) . . ? C4 C5 C6 121.3(8) . . ? N1 C6 C7 122.0(8) . . ? N1 C6 C5 115.2(8) . . ? C7 C6 C5 122.8(8) . . ? C8 C7 C6 119.8(8) . . ? C8 C7 C11 124.3(8) . . ? C6 C7 C11 115.9(8) . . ? C7 C8 C9 117.4(8) . . ? C7 C8 H8A 121.3 . . ? C9 C8 H8A 121.3 . . ? C8 C9 C10 121.5(9) . . ? C8 C9 H9A 119.2 . . ? C10 C9 H9A 119.2 . . ? N1 C10 C9 120.7(9) . . ? N1 C10 H10A 119.6 . . ? C9 C10 H10A 119.6 . . ? N3 C11 C12 111.3(7) . . ? N3 C11 C7 127.5(8) . . ? C12 C11 C7 121.1(8) . . ? N4 C12 C11 105.3(7) . . ? N4 C12 C4 133.2(8) . . ? C11 C12 C4 121.5(8) . . ? N3 C13 N4 112.5(7) . . ? N3 C13 C14 124.1(7) . . ? N4 C13 C14 123.4(8) . . ? C19 C14 C15 119.4(7) . . ? C19 C14 C13 118.5(8) . . ? C15 C14 C13 122.1(7) . . ? C16 C15 C14 119.7(8) . . ? C16 C15 H15A 120.1 . . ? C14 C15 H15A 120.1 . . ? C15 C16 C17 119.8(8) . . ? C15 C16 H16A 120.1 . . ? C17 C16 H16A 120.1 . . ? C18 C17 C16 122.2(8) . . ? C18 C17 Cl1 118.8(7) . . ? C16 C17 Cl1 118.9(7) . . ? C17 C18 C19 118.2(8) . . ? C17 C18 H18A 120.9 . . ? C19 C18 H18A 120.9 . . ? C14 C19 C18 120.6(8) . . ? C14 C19 H19A 119.7 . . ? C18 C19 H19A 119.7 . . ? C21 C20 H20A 109.5 . . ? C21 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C21 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O1 C21 C22 126.4(8) . . ? O1 C21 C20 114.2(9) . . ? C22 C21 C20 119.3(8) . . ? C21 C22 C23 124.6(8) . . ? C21 C22 H22A 117.7 . . ? C23 C22 H22A 117.7 . . ? O2 C23 C22 125.4(9) . . ? O2 C23 C24 113.3(9) . . ? C22 C23 C24 121.3(9) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O3 C25 H25A 109.5 . . ? O3 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O3 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C21 O1 Cu1 124.6(6) . . ? C23 O2 Cu1 124.1(6) . . ? C25 O3 Cu1 121.2(6) . . ? C25 O3 H7A 119.4 . . ? Cu1 O3 H7A 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 N1 C10 145.2(15) . . . . ? O2 Cu1 N1 C10 8.3(8) . . . . ? N2 Cu1 N1 C10 -179.8(8) . . . . ? O3 Cu1 N1 C10 -84.2(7) . . . . ? O1 Cu1 N1 C6 -39(2) . . . . ? O2 Cu1 N1 C6 -175.5(5) . . . . ? N2 Cu1 N1 C6 -3.6(5) . . . . ? O3 Cu1 N1 C6 92.0(5) . . . . ? O1 Cu1 N2 C1 -3.0(8) . . . . ? O2 Cu1 N2 C1 -127.8(13) . . . . ? N1 Cu1 N2 C1 -178.0(8) . . . . ? O3 Cu1 N2 C1 94.1(8) . . . . ? O1 Cu1 N2 C5 178.9(5) . . . . ? O2 Cu1 N2 C5 54.1(16) . . . . ? N1 Cu1 N2 C5 3.9(5) . . . . ? O3 Cu1 N2 C5 -84.0(6) . . . . ? C5 N2 C1 C2 0.6(13) . . . . ? Cu1 N2 C1 C2 -177.4(6) . . . . ? N2 C1 C2 C3 1.2(13) . . . . ? C1 C2 C3 C4 -2.3(12) . . . . ? C2 C3 C4 C5 1.7(12) . . . . ? C2 C3 C4 C12 -179.4(7) . . . . ? C1 N2 C5 C4 -1.2(12) . . . . ? Cu1 N2 C5 C4 177.0(6) . . . . ? C1 N2 C5 C6 178.2(8) . . . . ? Cu1 N2 C5 C6 -3.6(9) . . . . ? C3 C4 C5 N2 0.1(12) . . . . ? C12 C4 C5 N2 -178.9(7) . . . . ? C3 C4 C5 C6 -179.3(7) . . . . ? C12 C4 C5 C6 1.7(12) . . . . ? C10 N1 C6 C7 0.9(12) . . . . ? Cu1 N1 C6 C7 -175.7(6) . . . . ? C10 N1 C6 C5 179.3(7) . . . . ? Cu1 N1 C6 C5 2.7(9) . . . . ? N2 C5 C6 N1 0.6(11) . . . . ? C4 C5 C6 N1 -179.9(7) . . . . ? N2 C5 C6 C7 179.0(7) . . . . ? C4 C5 C6 C7 -1.6(13) . . . . ? N1 C6 C7 C8 -1.6(12) . . . . ? C5 C6 C7 C8 -179.9(8) . . . . ? N1 C6 C7 C11 178.8(7) . . . . ? C5 C6 C7 C11 0.5(12) . . . . ? C6 C7 C8 C9 1.1(13) . . . . ? C11 C7 C8 C9 -179.3(8) . . . . ? C7 C8 C9 C10 0.1(14) . . . . ? C6 N1 C10 C9 0.3(13) . . . . ? Cu1 N1 C10 C9 176.3(6) . . . . ? C8 C9 C10 N1 -0.8(14) . . . . ? C13 N3 C11 C12 -0.9(9) . . . . ? C13 N3 C11 C7 -179.3(8) . . . . ? C8 C7 C11 N3 -1.0(14) . . . . ? C6 C7 C11 N3 178.6(7) . . . . ? C8 C7 C11 C12 -179.3(8) . . . . ? C6 C7 C11 C12 0.3(12) . . . . ? C13 N4 C12 C11 -1.1(8) . . . . ? C13 N4 C12 C4 178.9(8) . . . . ? N3 C11 C12 N4 1.2(9) . . . . ? C7 C11 C12 N4 179.8(7) . . . . ? N3 C11 C12 C4 -178.7(7) . . . . ? C7 C11 C12 C4 -0.2(12) . . . . ? C5 C4 C12 N4 179.2(8) . . . . ? C3 C4 C12 N4 0.3(14) . . . . ? C5 C4 C12 C11 -0.9(12) . . . . ? C3 C4 C12 C11 -179.8(8) . . . . ? C11 N3 C13 N4 0.2(9) . . . . ? C11 N3 C13 C14 -178.9(7) . . . . ? C12 N4 C13 N3 0.6(9) . . . . ? C12 N4 C13 C14 179.6(7) . . . . ? N3 C13 C14 C19 -7.2(12) . . . . ? N4 C13 C14 C19 173.8(8) . . . . ? N3 C13 C14 C15 172.6(8) . . . . ? N4 C13 C14 C15 -6.3(12) . . . . ? C19 C14 C15 C16 2.6(13) . . . . ? C13 C14 C15 C16 -177.3(8) . . . . ? C14 C15 C16 C17 -1.7(13) . . . . ? C15 C16 C17 C18 0.1(14) . . . . ? C15 C16 C17 Cl1 179.3(7) . . . . ? C16 C17 C18 C19 0.6(13) . . . . ? Cl1 C17 C18 C19 -178.6(6) . . . . ? C15 C14 C19 C18 -1.9(13) . . . . ? C13 C14 C19 C18 178.0(7) . . . . ? C17 C18 C19 C14 0.3(13) . . . . ? O1 C21 C22 C23 6.2(16) . . . . ? C20 C21 C22 C23 -174.1(9) . . . . ? C21 C22 C23 O2 -3.8(16) . . . . ? C21 C22 C23 C24 176.2(9) . . . . ? C22 C21 O1 Cu1 -1.8(13) . . . . ? C20 C21 O1 Cu1 178.4(6) . . . . ? O2 Cu1 O1 C21 -2.9(7) . . . . ? N1 Cu1 O1 C21 -139.7(16) . . . . ? N2 Cu1 O1 C21 -174.3(7) . . . . ? O3 Cu1 O1 C21 90.3(7) . . . . ? C22 C23 O2 Cu1 -2.5(13) . . . . ? C24 C23 O2 Cu1 177.6(6) . . . . ? O1 Cu1 O2 C23 4.9(7) . . . . ? N1 Cu1 O2 C23 179.0(7) . . . . ? N2 Cu1 O2 C23 129.5(13) . . . . ? O3 Cu1 O2 C23 -92.2(7) . . . . ? O1 Cu1 O3 C25 -78.3(9) . . . . ? O2 Cu1 O3 C25 16.7(9) . . . . ? N1 Cu1 O3 C25 108.4(9) . . . . ? N2 Cu1 O3 C25 -170.4(9) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.706 _refine_diff_density_min -0.710 _refine_diff_density_rms 0.113 _database_code_depnum_ccdc_archive 'CCDC 801495' ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 Cu N6 O7' _chemical_formula_weight 565.99 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.418(3) _cell_length_b 9.753(3) _cell_length_c 28.363(10) _cell_angle_alpha 92.028(7) _cell_angle_beta 90.542(6) _cell_angle_gamma 93.765(8) _cell_volume 2322.0(14) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 951 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 28.12 _exptl_crystal_description Prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.619 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1156 _exptl_absorpt_coefficient_mu 1.001 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8249 _exptl_absorpt_correction_T_max 0.8893 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 19659 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0944 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 25.10 _reflns_number_total 8116 _reflns_number_gt 6070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8116 _refine_ls_number_parameters 685 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0778 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1225 _refine_ls_wR_factor_gt 0.1122 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 Cu1 Cu 0.47327(6) -0.04777(5) 0.396862(16) 0.02301(15) Uani 1 1 d . . . O1 O -0.0600(3) 0.5476(3) 0.57114(9) 0.0291(7) Uani 1 1 d . . . O2 O 0.1542(3) 0.6260(3) 0.61028(10) 0.0297(7) Uani 1 1 d . . . O3 O 0.4839(3) -0.2333(3) 0.37338(9) 0.0258(7) Uani 1 1 d . . . O4 O 0.6223(3) 0.0282(3) 0.35323(10) 0.0291(7) Uani 1 1 d . . . O5 O 0.2437(3) -0.0031(3) 0.35582(10) 0.0287(7) Uani 1 1 d . . . O6 O 0.2635(3) 0.2147(3) 0.34119(10) 0.0312(7) Uani 1 1 d . . . O7 O 0.0467(4) 0.1233(3) 0.37109(10) 0.0377(8) Uani 1 1 d . . . N1 N 0.3379(4) -0.1092(3) 0.45092(11) 0.0197(8) Uani 1 1 d . . . N2 N 0.4560(4) 0.1362(3) 0.42955(11) 0.0211(8) Uani 1 1 d . . . N3 N 0.0835(4) 0.1171(3) 0.58723(10) 0.0199(8) Uani 1 1 d . . . H3B H 0.0329 0.0542 0.6027 0.024 Uiso 1 1 calc R . . N4 N 0.1788(4) 0.3271(3) 0.56671(11) 0.0212(8) Uani 1 1 d . . . N5 N 0.0320(4) 0.5494(3) 0.60519(11) 0.0228(8) Uani 1 1 d . . . N6 N 0.1852(4) 0.1128(3) 0.35603(11) 0.0231(8) Uani 1 1 d . . . C1 C -0.1228(5) 0.4344(4) 0.72015(14) 0.0275(10) Uani 1 1 d . . . H1A H -0.1704 0.4731 0.7465 0.033 Uiso 1 1 calc R . . C2 C 0.1752(5) -0.2640(4) 0.49724(13) 0.0213(9) Uani 1 1 d . . . H2A H 0.1338 -0.3533 0.5017 0.026 Uiso 1 1 calc R . . C3 C 0.3779(5) 0.3773(4) 0.47637(13) 0.0214(9) Uani 1 1 d . . . H3A H 0.3513 0.4586 0.4915 0.026 Uiso 1 1 calc R . . C4 C 0.2974(5) -0.0043(4) 0.48090(13) 0.0186(9) Uani 1 1 d . . . C5 C 0.3213(5) 0.2498(4) 0.49378(13) 0.0182(9) Uani 1 1 d . . . C6 C 0.3620(5) 0.1316(4) 0.46805(13) 0.0197(9) Uani 1 1 d . . . C7 C 0.1698(5) 0.0981(4) 0.54732(13) 0.0182(9) Uani 1 1 d . . . C8 C 0.1996(5) -0.0239(4) 0.51988(13) 0.0186(9) Uani 1 1 d . . . C9 C 0.6666(5) -0.0351(5) 0.31559(15) 0.0318(11) Uani 1 1 d . . . C10 C 0.0928(5) 0.2567(4) 0.59798(13) 0.0199(9) Uani 1 1 d . . . C11 C 0.2767(5) -0.2367(4) 0.45942(13) 0.0229(9) Uani 1 1 d . . . H11A H 0.3027 -0.3093 0.4395 0.027 Uiso 1 1 calc R . . C12 C 0.2274(4) 0.2294(4) 0.53473(13) 0.0185(9) Uani 1 1 d . . . C13 C -0.0088(5) 0.4565(4) 0.64384(13) 0.0191(9) Uani 1 1 d . . . C14 C 0.5476(5) -0.2664(4) 0.33404(14) 0.0284(10) Uani 1 1 d . . . C15 C 0.0178(5) 0.3168(4) 0.63976(13) 0.0205(9) Uani 1 1 d . . . C16 C -0.0990(5) 0.2944(4) 0.71759(14) 0.0267(10) Uani 1 1 d . . . H16A H -0.1307 0.2393 0.7424 0.032 Uiso 1 1 calc R . . C17 C 0.5102(5) 0.2583(4) 0.41446(14) 0.0255(10) Uani 1 1 d . . . H17A H 0.5753 0.2617 0.3882 0.031 Uiso 1 1 calc R . . C18 C 0.1365(5) -0.1595(4) 0.52776(13) 0.0208(9) Uani 1 1 d . . . H18A H 0.0702 -0.1772 0.5532 0.025 Uiso 1 1 calc R . . C19 C 0.4718(5) 0.3818(4) 0.43719(14) 0.0265(10) Uani 1 1 d . . . H19A H 0.5097 0.4658 0.4258 0.032 Uiso 1 1 calc R . . C20 C -0.0749(5) 0.5154(4) 0.68316(14) 0.0256(10) Uani 1 1 d . . . H20A H -0.0873 0.6095 0.6849 0.031 Uiso 1 1 calc R . . C21 C 0.6286(5) -0.1747(5) 0.30473(14) 0.0322(11) Uani 1 1 d . . . H21A H 0.6602 -0.2090 0.2755 0.039 Uiso 1 1 calc R . . C22 C -0.0279(5) 0.2365(4) 0.67814(13) 0.0232(9) Uani 1 1 d . . . H22A H -0.0104 0.1432 0.6772 0.028 Uiso 1 1 calc R . . C23 C 0.5342(5) -0.4178(4) 0.32065(14) 0.0348(11) Uani 1 1 d . . . H23A H 0.4752 -0.4668 0.3443 0.052 Uiso 1 1 calc R . . H23B H 0.6388 -0.4511 0.3184 0.052 Uiso 1 1 calc R . . H23C H 0.4801 -0.4320 0.2908 0.052 Uiso 1 1 calc R . . C24 C 0.7681(5) 0.0510(5) 0.28300(15) 0.0412(12) Uani 1 1 d . . . H24A H 0.7820 0.1435 0.2958 0.062 Uiso 1 1 calc R . . H24B H 0.7169 0.0510 0.2526 0.062 Uiso 1 1 calc R . . H24C H 0.8701 0.0133 0.2798 0.062 Uiso 1 1 calc R . . Cu2 Cu 0.92315(6) 0.54403(5) 0.912593(17) 0.02525(15) Uani 1 1 d . . . O8 O 0.6319(4) -0.1344(3) 1.13498(11) 0.0507(10) Uani 1 1 d . . . O9 O 0.4249(4) -0.0824(3) 1.09367(10) 0.0416(8) Uani 1 1 d . . . O10 O 0.9340(3) 0.7277(3) 0.89056(9) 0.0296(7) Uani 1 1 d . . . O11 O 1.0755(3) 0.4802(3) 0.86960(10) 0.0324(7) Uani 1 1 d . . . O12 O 0.6926(3) 0.4693(3) 0.87117(9) 0.0267(7) Uani 1 1 d . . . O13 O 0.5862(4) 0.3840(3) 0.80567(11) 0.0414(9) Uani 1 1 d . . . O14 O 0.7938(4) 0.2958(3) 0.83412(10) 0.0391(8) Uani 1 1 d . . . N7 N 0.9117(4) 0.3636(3) 0.94510(11) 0.0240(8) Uani 1 1 d . . . N8 N 0.7931(4) 0.6007(3) 0.96861(11) 0.0211(8) Uani 1 1 d . . . N9 N 0.6473(4) 0.1654(3) 1.08423(11) 0.0222(8) Uani 1 1 d . . . N10 N 0.5476(4) 0.3669(3) 1.10445(10) 0.0201(8) Uani 1 1 d . . . H10A H 0.4959 0.4265 1.1200 0.024 Uiso 1 1 calc R . . N11 N 0.5151(5) -0.0678(4) 1.12832(12) 0.0325(9) Uani 1 1 d . . . N12 N 0.6908(4) 0.3801(3) 0.83662(11) 0.0259(8) Uani 1 1 d . . . C25 C 0.8219(5) 0.3651(4) 0.98472(13) 0.0234(9) Uani 1 1 d . . . C26 C 0.6429(5) 0.7466(4) 1.01810(13) 0.0230(9) Uani 1 1 d . . . H26A H 0.6074 0.8335 1.0245 0.028 Uiso 1 1 calc R . . C27 C 0.6050(5) 0.6398(4) 1.04793(13) 0.0221(9) Uani 1 1 d . . . H27A H 0.5422 0.6537 1.0742 0.027 Uiso 1 1 calc R . . C28 C 0.5582(5) 0.2315(4) 1.11536(13) 0.0219(9) Uani 1 1 d . . . C29 C 0.6939(5) 0.2639(4) 1.05225(13) 0.0221(9) Uani 1 1 d . . . C30 C 0.7576(5) 0.4951(4) 0.99810(13) 0.0222(9) Uani 1 1 d . . . C31 C 0.9659(5) 0.2462(4) 0.92942(14) 0.0275(10) Uani 1 1 d . . . H31A H 1.0273 0.2453 0.9023 0.033 Uiso 1 1 calc R . . C32 C 0.4749(5) 0.0343(4) 1.16605(13) 0.0234(10) Uani 1 1 d . . . C33 C 0.6629(5) 0.5105(4) 1.03778(13) 0.0191(9) Uani 1 1 d . . . C34 C 0.6337(5) 0.3897(4) 1.06463(13) 0.0199(9) Uani 1 1 d . . . C35 C 0.4419(5) 0.2611(4) 1.19493(13) 0.0278(10) Uani 1 1 d . . . H35A H 0.4495 0.3557 1.1914 0.033 Uiso 1 1 calc R . . C36 C 0.9961(5) 0.7608(5) 0.85088(15) 0.0304(11) Uani 1 1 d . . . C37 C 1.0761(5) 0.6737(5) 0.82050(14) 0.0345(11) Uani 1 1 d . . . H37A H 1.1058 0.7058 0.7912 0.041 Uiso 1 1 calc R . . C38 C 0.7873(5) 0.2469(4) 1.01096(13) 0.0199(9) Uani 1 1 d . . . C39 C 0.7349(5) 0.7220(4) 0.97856(13) 0.0253(10) Uani 1 1 d . . . H39A H 0.7566 0.7933 0.9582 0.030 Uiso 1 1 calc R . . C40 C 1.1145(5) 0.5399(5) 0.83168(15) 0.0333(11) Uani 1 1 d . . . C41 C 0.4890(5) 0.1741(4) 1.15775(13) 0.0214(9) Uani 1 1 d . . . C42 C 0.3742(5) 0.0681(4) 1.24313(14) 0.0299(11) Uani 1 1 d . . . H42A H 0.3359 0.0337 1.2713 0.036 Uiso 1 1 calc R . . C43 C 0.8449(5) 0.1233(4) 0.99314(14) 0.0251(10) Uani 1 1 d . . . H43A H 0.8231 0.0421 1.0088 0.030 Uiso 1 1 calc R . . C44 C 0.9329(5) 0.1222(4) 0.95283(14) 0.0291(11) Uani 1 1 d . . . H44A H 0.9706 0.0406 0.9409 0.035 Uiso 1 1 calc R . . C45 C 0.4212(5) -0.0215(4) 1.20751(14) 0.0270(10) Uani 1 1 d . . . H45A H 0.4166 -0.1159 1.2115 0.032 Uiso 1 1 calc R . . C46 C 0.3844(5) 0.2086(4) 1.23666(14) 0.0304(11) Uani 1 1 d . . . H46A H 0.3524 0.2681 1.2606 0.036 Uiso 1 1 calc R . . C47 C 1.2095(6) 0.4579(5) 0.79755(15) 0.0417(13) Uani 1 1 d . . . H47A H 1.2253 0.3697 0.8101 0.062 Uiso 1 1 calc R . . H47B H 1.3109 0.5060 0.7927 0.062 Uiso 1 1 calc R . . H47C H 1.1529 0.4457 0.7680 0.062 Uiso 1 1 calc R . . C48 C 0.9827(6) 0.9089(4) 0.83813(15) 0.0406(12) Uani 1 1 d . . . H48A H 0.9249 0.9554 0.8622 0.061 Uiso 1 1 calc R . . H48B H 0.9274 0.9118 0.8085 0.061 Uiso 1 1 calc R . . H48C H 1.0874 0.9533 0.8357 0.061 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 0.0221(3) 0.0276(3) 0.0195(3) 0.0001(2) 0.0045(2) 0.0024(2) O1 0.0294(19) 0.0314(17) 0.0274(16) 0.0034(13) -0.0034(14) 0.0069(14) O2 0.0216(18) 0.0285(17) 0.0383(18) 0.0032(14) 0.0057(14) -0.0058(14) O3 0.0261(18) 0.0282(16) 0.0234(15) -0.0010(13) 0.0051(13) 0.0049(13) O4 0.0249(18) 0.0332(17) 0.0294(17) 0.0016(14) 0.0073(14) 0.0016(13) O5 0.0290(18) 0.0215(16) 0.0356(18) -0.0011(13) -0.0080(14) 0.0049(13) O6 0.037(2) 0.0269(17) 0.0294(17) 0.0070(13) 0.0058(14) -0.0057(14) O7 0.034(2) 0.0374(19) 0.043(2) 0.0012(15) 0.0201(16) 0.0036(15) N1 0.022(2) 0.0177(18) 0.0195(17) -0.0009(14) 0.0000(15) 0.0059(14) N2 0.020(2) 0.0238(19) 0.0195(18) 0.0011(14) 0.0000(15) -0.0021(15) N3 0.023(2) 0.0158(17) 0.0207(18) 0.0002(14) 0.0049(15) -0.0009(14) N4 0.022(2) 0.0217(18) 0.0200(18) 0.0009(14) -0.0004(15) 0.0016(15) N5 0.028(2) 0.0167(18) 0.0247(19) 0.0019(15) 0.0067(16) 0.0075(16) N6 0.027(2) 0.026(2) 0.0158(18) -0.0022(15) -0.0007(16) 0.0045(17) C1 0.029(3) 0.029(2) 0.024(2) -0.0059(19) 0.0096(19) 0.004(2) C2 0.023(3) 0.022(2) 0.019(2) 0.0007(17) -0.0012(18) 0.0032(18) C3 0.022(2) 0.022(2) 0.020(2) 0.0011(17) -0.0020(18) -0.0014(18) C4 0.015(2) 0.022(2) 0.020(2) 0.0011(17) -0.0031(17) 0.0035(17) C5 0.013(2) 0.022(2) 0.019(2) 0.0004(17) -0.0033(17) 0.0007(17) C6 0.013(2) 0.027(2) 0.018(2) 0.0057(17) -0.0026(17) -0.0044(17) C7 0.020(2) 0.018(2) 0.016(2) 0.0002(16) 0.0006(17) -0.0003(17) C8 0.018(2) 0.021(2) 0.017(2) 0.0016(16) -0.0009(17) 0.0039(17) C9 0.023(3) 0.049(3) 0.025(2) 0.008(2) 0.004(2) 0.007(2) C10 0.021(2) 0.021(2) 0.019(2) -0.0001(16) -0.0011(18) 0.0029(17) C11 0.022(3) 0.025(2) 0.022(2) -0.0024(17) -0.0018(18) 0.0085(18) C12 0.013(2) 0.022(2) 0.019(2) -0.0019(17) 0.0002(17) -0.0007(17) C13 0.018(2) 0.020(2) 0.019(2) 0.0037(16) -0.0009(17) -0.0065(17) C14 0.025(3) 0.039(3) 0.022(2) -0.001(2) -0.0001(19) 0.008(2) C15 0.023(2) 0.021(2) 0.018(2) -0.0028(16) -0.0006(17) 0.0013(17) C16 0.026(3) 0.033(3) 0.020(2) 0.0002(19) 0.0048(19) -0.003(2) C17 0.019(3) 0.035(3) 0.022(2) -0.0010(19) -0.0014(18) -0.0061(19) C18 0.020(2) 0.023(2) 0.019(2) 0.0044(17) 0.0033(17) 0.0014(18) C19 0.028(3) 0.025(2) 0.025(2) 0.0010(18) -0.0011(19) -0.0076(19) C20 0.026(3) 0.022(2) 0.029(2) -0.0013(18) -0.001(2) 0.0038(18) C21 0.033(3) 0.045(3) 0.020(2) -0.002(2) 0.012(2) 0.013(2) C22 0.028(3) 0.020(2) 0.021(2) -0.0007(17) 0.0022(18) -0.0027(18) C23 0.040(3) 0.038(3) 0.028(2) -0.003(2) 0.004(2) 0.014(2) C24 0.036(3) 0.053(3) 0.036(3) 0.010(2) 0.015(2) 0.000(2) Cu2 0.0247(3) 0.0330(3) 0.0183(3) 0.0006(2) 0.0048(2) 0.0032(2) O8 0.075(3) 0.038(2) 0.042(2) -0.0010(16) 0.0002(19) 0.0290(19) O9 0.042(2) 0.053(2) 0.0274(17) -0.0125(16) -0.0025(16) -0.0112(16) O10 0.0306(19) 0.0376(18) 0.0206(15) 0.0029(13) 0.0091(13) 0.0008(14) O11 0.0258(19) 0.046(2) 0.0256(16) 0.0001(14) 0.0065(14) 0.0050(14) O12 0.0283(18) 0.0297(16) 0.0223(15) -0.0081(13) -0.0003(13) 0.0080(13) O13 0.037(2) 0.044(2) 0.043(2) -0.0151(16) -0.0190(17) 0.0101(16) O14 0.039(2) 0.044(2) 0.0361(18) -0.0133(15) -0.0098(16) 0.0219(17) N7 0.022(2) 0.034(2) 0.0163(17) -0.0034(15) 0.0002(15) 0.0092(16) N8 0.022(2) 0.0216(18) 0.0194(17) -0.0008(14) -0.0021(15) 0.0026(15) N9 0.023(2) 0.0241(19) 0.0190(18) 0.0034(14) 0.0035(15) 0.0005(15) N10 0.023(2) 0.0187(18) 0.0187(17) -0.0040(14) 0.0023(15) 0.0057(15) N11 0.048(3) 0.024(2) 0.025(2) 0.0003(16) 0.0088(19) -0.0037(19) N12 0.026(2) 0.028(2) 0.0235(19) 0.0047(16) 0.0024(17) -0.0006(17) C25 0.023(3) 0.030(2) 0.018(2) -0.0050(18) 0.0008(18) 0.0065(19) C26 0.022(3) 0.023(2) 0.023(2) -0.0042(17) 0.0018(18) -0.0005(18) C27 0.022(3) 0.024(2) 0.019(2) -0.0011(17) 0.0005(18) -0.0015(18) C28 0.028(3) 0.019(2) 0.018(2) -0.0016(17) -0.0009(18) 0.0011(18) C29 0.023(3) 0.025(2) 0.019(2) -0.0040(17) -0.0022(18) 0.0015(18) C30 0.021(3) 0.026(2) 0.019(2) -0.0008(17) -0.0041(18) 0.0020(18) C31 0.021(3) 0.043(3) 0.020(2) -0.0054(19) -0.0013(18) 0.010(2) C32 0.030(3) 0.025(2) 0.015(2) -0.0064(17) -0.0024(18) 0.0002(19) C33 0.020(2) 0.021(2) 0.015(2) -0.0058(16) -0.0010(17) 0.0025(18) C34 0.021(2) 0.023(2) 0.015(2) -0.0004(16) 0.0004(17) 0.0009(18) C35 0.038(3) 0.025(2) 0.021(2) 0.0040(18) 0.003(2) 0.006(2) C36 0.022(3) 0.043(3) 0.026(2) 0.000(2) 0.001(2) -0.001(2) C37 0.034(3) 0.050(3) 0.019(2) 0.003(2) 0.007(2) -0.004(2) C38 0.020(2) 0.023(2) 0.016(2) -0.0030(17) 0.0001(17) 0.0043(18) C39 0.028(3) 0.030(2) 0.017(2) 0.0017(18) -0.0020(18) -0.004(2) C40 0.021(3) 0.053(3) 0.024(2) -0.006(2) 0.003(2) -0.006(2) C41 0.020(2) 0.024(2) 0.020(2) -0.0025(17) 0.0033(17) 0.0029(18) C42 0.042(3) 0.030(2) 0.019(2) 0.0055(19) 0.003(2) 0.006(2) C43 0.023(3) 0.029(2) 0.024(2) 0.0016(18) -0.0008(19) 0.0088(19) C44 0.030(3) 0.032(3) 0.026(2) -0.0022(19) -0.003(2) 0.014(2) C45 0.035(3) 0.021(2) 0.025(2) 0.0009(18) 0.001(2) -0.0011(19) C46 0.039(3) 0.031(3) 0.021(2) -0.0032(19) 0.005(2) 0.008(2) C47 0.036(3) 0.064(3) 0.026(2) -0.005(2) 0.016(2) 0.011(3) C48 0.047(3) 0.046(3) 0.028(3) 0.009(2) 0.008(2) -0.007(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 O4 1.904(3) . ? Cu1 O3 1.914(3) . ? Cu1 N1 2.004(3) . ? Cu1 N2 2.005(3) . ? Cu1 O5 2.320(3) . ? O1 N5 1.231(4) . ? O2 N5 1.235(4) . ? O3 C14 1.283(5) . ? O4 C9 1.285(5) . ? O5 N6 1.263(4) . ? O6 N6 1.244(4) . ? O7 N6 1.255(4) . ? N1 C11 1.345(5) . ? N1 C4 1.370(5) . ? N2 C17 1.333(5) . ? N2 C6 1.355(5) . ? N3 C7 1.364(5) . ? N3 C10 1.381(4) . ? N3 H3B 0.8600 . ? N4 C10 1.331(5) . ? N4 C12 1.376(5) . ? N5 C13 1.476(5) . ? C1 C20 1.383(5) . ? C1 C16 1.393(5) . ? C1 H1A 0.9300 . ? C2 C18 1.372(5) . ? C2 C11 1.400(5) . ? C2 H2A 0.9300 . ? C3 C19 1.370(5) . ? C3 C5 1.410(5) . ? C3 H3A 0.9300 . ? C4 C8 1.396(5) . ? C4 C6 1.459(5) . ? C5 C6 1.406(5) . ? C5 C12 1.424(5) . ? C7 C12 1.399(5) . ? C7 C8 1.436(5) . ? C8 C18 1.419(5) . ? C9 C21 1.401(6) . ? C9 C24 1.505(6) . ? C10 C15 1.470(5) . ? C11 H11A 0.9300 . ? C13 C20 1.375(5) . ? C13 C15 1.396(5) . ? C14 C21 1.393(6) . ? C14 C23 1.509(5) . ? C15 C22 1.406(5) . ? C16 C22 1.394(5) . ? C16 H16A 0.9300 . ? C17 C19 1.404(5) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C20 H20A 0.9300 . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? Cu2 O11 1.897(3) . ? Cu2 O10 1.914(3) . ? Cu2 N7 2.012(3) . ? Cu2 N8 2.020(3) . ? Cu2 O12 2.322(3) . ? O8 N11 1.230(4) . ? O9 N11 1.235(4) . ? O10 C36 1.288(5) . ? O11 C40 1.277(5) . ? O12 N12 1.286(4) . ? O13 N12 1.241(4) . ? O14 N12 1.234(4) . ? N7 C31 1.324(5) . ? N7 C25 1.361(5) . ? N8 C39 1.332(5) . ? N8 C30 1.369(5) . ? N9 C28 1.339(5) . ? N9 C29 1.385(5) . ? N10 C34 1.365(5) . ? N10 C28 1.375(4) . ? N10 H10A 0.8600 . ? N11 C32 1.493(5) . ? C25 C38 1.410(5) . ? C25 C30 1.450(5) . ? C26 C27 1.388(5) . ? C26 C39 1.391(5) . ? C26 H26A 0.9300 . ? C27 C33 1.403(5) . ? C27 H27A 0.9300 . ? C28 C41 1.455(5) . ? C29 C34 1.393(5) . ? C29 C38 1.427(5) . ? C30 C33 1.395(5) . ? C31 C44 1.413(6) . ? C31 H31A 0.9300 . ? C32 C45 1.380(5) . ? C32 C41 1.390(5) . ? C33 C34 1.435(5) . ? C35 C46 1.385(5) . ? C35 C41 1.406(5) . ? C35 H35A 0.9300 . ? C36 C37 1.397(6) . ? C36 C48 1.512(6) . ? C37 C40 1.410(6) . ? C37 H37A 0.9300 . ? C38 C43 1.408(5) . ? C39 H39A 0.9300 . ? C40 C47 1.504(6) . ? C42 C46 1.386(5) . ? C42 C45 1.389(5) . ? C42 H42A 0.9300 . ? C43 C44 1.368(6) . ? C43 H43A 0.9300 . ? C44 H44A 0.9300 . ? C45 H45A 0.9300 . ? C46 H46A 0.9300 . ? C47 H47A 0.9600 . ? C47 H47B 0.9600 . ? C47 H47C 0.9600 . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 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 O4 Cu1 O3 94.92(12) . . ? O4 Cu1 N1 170.49(12) . . ? O3 Cu1 N1 91.41(12) . . ? O4 Cu1 N2 91.49(13) . . ? O3 Cu1 N2 172.61(12) . . ? N1 Cu1 N2 81.78(13) . . ? O4 Cu1 O5 97.31(11) . . ? O3 Cu1 O5 96.37(10) . . ? N1 Cu1 O5 89.01(12) . . ? N2 Cu1 O5 86.44(11) . . ? C14 O3 Cu1 123.8(3) . . ? C9 O4 Cu1 124.4(3) . . ? N6 O5 Cu1 123.9(2) . . ? C11 N1 C4 117.5(4) . . ? C11 N1 Cu1 128.3(3) . . ? C4 N1 Cu1 114.0(3) . . ? C17 N2 C6 118.9(3) . . ? C17 N2 Cu1 127.2(3) . . ? C6 N2 Cu1 113.4(3) . . ? C7 N3 C10 106.9(3) . . ? C7 N3 H3B 126.5 . . ? C10 N3 H3B 126.5 . . ? C10 N4 C12 105.1(3) . . ? O1 N5 O2 125.1(3) . . ? O1 N5 C13 117.8(3) . . ? O2 N5 C13 117.0(3) . . ? O6 N6 O7 120.7(3) . . ? O6 N6 O5 120.4(4) . . ? O7 N6 O5 118.9(3) . . ? C20 C1 C16 119.3(4) . . ? C20 C1 H1A 120.4 . . ? C16 C1 H1A 120.4 . . ? C18 C2 C11 120.2(4) . . ? C18 C2 H2A 119.9 . . ? C11 C2 H2A 119.9 . . ? C19 C3 C5 120.2(4) . . ? C19 C3 H3A 119.9 . . ? C5 C3 H3A 119.9 . . ? N1 C4 C8 123.4(4) . . ? N1 C4 C6 114.3(4) . . ? C8 C4 C6 122.3(4) . . ? C6 C5 C3 116.5(4) . . ? C6 C5 C12 117.1(3) . . ? C3 C5 C12 126.4(4) . . ? N2 C6 C5 123.1(4) . . ? N2 C6 C4 116.4(4) . . ? C5 C6 C4 120.5(4) . . ? N3 C7 C12 105.8(3) . . ? N3 C7 C8 131.5(3) . . ? C12 C7 C8 122.6(4) . . ? C4 C8 C18 117.7(4) . . ? C4 C8 C7 115.7(3) . . ? C18 C8 C7 126.6(4) . . ? O4 C9 C21 124.1(4) . . ? O4 C9 C24 115.3(4) . . ? C21 C9 C24 120.6(4) . . ? N4 C10 N3 111.9(3) . . ? N4 C10 C15 125.2(3) . . ? N3 C10 C15 122.8(4) . . ? N1 C11 C2 122.4(4) . . ? N1 C11 H11A 118.8 . . ? C2 C11 H11A 118.8 . . ? N4 C12 C7 110.3(4) . . ? N4 C12 C5 128.2(4) . . ? C7 C12 C5 121.6(4) . . ? C20 C13 C15 122.9(4) . . ? C20 C13 N5 116.2(3) . . ? C15 C13 N5 121.0(4) . . ? O3 C14 C21 125.0(4) . . ? O3 C14 C23 115.3(4) . . ? C21 C14 C23 119.7(4) . . ? C13 C15 C22 116.6(4) . . ? C13 C15 C10 122.0(4) . . ? C22 C15 C10 121.4(3) . . ? C22 C16 C1 120.4(4) . . ? C22 C16 H16A 119.8 . . ? C1 C16 H16A 119.8 . . ? N2 C17 C19 121.8(4) . . ? N2 C17 H17A 119.1 . . ? C19 C17 H17A 119.1 . . ? C2 C18 C8 118.8(4) . . ? C2 C18 H18A 120.6 . . ? C8 C18 H18A 120.6 . . ? C3 C19 C17 119.3(4) . . ? C3 C19 H19A 120.3 . . ? C17 C19 H19A 120.3 . . ? C13 C20 C1 119.9(4) . . ? C13 C20 H20A 120.1 . . ? C1 C20 H20A 120.1 . . ? C14 C21 C9 125.4(4) . . ? C14 C21 H21A 117.3 . . ? C9 C21 H21A 117.3 . . ? C16 C22 C15 121.0(4) . . ? C16 C22 H22A 119.5 . . ? C15 C22 H22A 119.5 . . ? C14 C23 H23A 109.5 . . ? C14 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C14 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C9 C24 H24A 109.5 . . ? C9 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C9 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O11 Cu2 O10 94.91(13) . . ? O11 Cu2 N7 91.13(13) . . ? O10 Cu2 N7 171.79(12) . . ? O11 Cu2 N8 168.14(12) . . ? O10 Cu2 N8 91.09(12) . . ? N7 Cu2 N8 81.99(13) . . ? O11 Cu2 O12 98.95(11) . . ? O10 Cu2 O12 96.05(11) . . ? N7 Cu2 O12 88.47(11) . . ? N8 Cu2 O12 90.55(11) . . ? C36 O10 Cu2 123.2(3) . . ? C40 O11 Cu2 123.9(3) . . ? N12 O12 Cu2 122.9(2) . . ? C31 N7 C25 119.3(4) . . ? C31 N7 Cu2 127.2(3) . . ? C25 N7 Cu2 113.1(3) . . ? C39 N8 C30 118.3(4) . . ? C39 N8 Cu2 128.7(3) . . ? C30 N8 Cu2 112.9(3) . . ? C28 N9 C29 104.5(3) . . ? C34 N10 C28 107.8(3) . . ? C34 N10 H10A 126.1 . . ? C28 N10 H10A 126.1 . . ? O8 N11 O9 125.2(4) . . ? O8 N11 C32 117.5(3) . . ? O9 N11 C32 117.3(4) . . ? O14 N12 O13 121.6(3) . . ? O14 N12 O12 120.2(3) . . ? O13 N12 O12 118.3(3) . . ? N7 C25 C38 122.7(4) . . ? N7 C25 C30 116.3(4) . . ? C38 C25 C30 120.9(4) . . ? C27 C26 C39 119.2(4) . . ? C27 C26 H26A 120.4 . . ? C39 C26 H26A 120.4 . . ? C26 C27 C33 119.0(4) . . ? C26 C27 H27A 120.5 . . ? C33 C27 H27A 120.5 . . ? N9 C28 N10 111.6(3) . . ? N9 C28 C41 125.8(3) . . ? N10 C28 C41 122.5(4) . . ? N9 C29 C34 110.7(4) . . ? N9 C29 C38 127.8(4) . . ? C34 C29 C38 121.4(4) . . ? N8 C30 C33 122.3(4) . . ? N8 C30 C25 115.6(4) . . ? C33 C30 C25 122.2(4) . . ? N7 C31 C44 121.6(4) . . ? N7 C31 H31A 119.2 . . ? C44 C31 H31A 119.2 . . ? C45 C32 C41 124.7(4) . . ? C45 C32 N11 115.2(3) . . ? C41 C32 N11 120.2(4) . . ? C30 C33 C27 118.3(4) . . ? C30 C33 C34 115.7(3) . . ? C27 C33 C34 126.0(4) . . ? N10 C34 C29 105.4(3) . . ? N10 C34 C33 131.6(4) . . ? C29 C34 C33 123.0(4) . . ? C46 C35 C41 121.3(4) . . ? C46 C35 H35A 119.3 . . ? C41 C35 H35A 119.3 . . ? O10 C36 C37 125.7(4) . . ? O10 C36 C48 115.2(4) . . ? C37 C36 C48 119.1(4) . . ? C36 C37 C40 123.9(4) . . ? C36 C37 H37A 118.1 . . ? C40 C37 H37A 118.1 . . ? C43 C38 C25 116.7(4) . . ? C43 C38 C29 126.5(4) . . ? C25 C38 C29 116.7(4) . . ? N8 C39 C26 122.9(4) . . ? N8 C39 H39A 118.6 . . ? C26 C39 H39A 118.6 . . ? O11 C40 C37 125.0(4) . . ? O11 C40 C47 115.4(4) . . ? C37 C40 C47 119.5(4) . . ? C32 C41 C35 115.6(4) . . ? C32 C41 C28 123.8(4) . . ? C35 C41 C28 120.5(4) . . ? C46 C42 C45 120.0(4) . . ? C46 C42 H42A 120.0 . . ? C45 C42 H42A 120.0 . . ? C44 C43 C38 120.1(4) . . ? C44 C43 H43A 119.9 . . ? C38 C43 H43A 119.9 . . ? C43 C44 C31 119.5(4) . . ? C43 C44 H44A 120.3 . . ? C31 C44 H44A 120.3 . . ? C32 C45 C42 117.8(4) . . ? C32 C45 H45A 121.1 . . ? C42 C45 H45A 121.1 . . ? C35 C46 C42 120.6(4) . . ? C35 C46 H46A 119.7 . . ? C42 C46 H46A 119.7 . . ? C40 C47 H47A 109.5 . . ? C40 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C40 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C36 C48 H48A 109.5 . . ? C36 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C36 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 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 O4 Cu1 O3 C14 -13.5(3) . . . . ? N1 Cu1 O3 C14 173.6(3) . . . . ? N2 Cu1 O3 C14 -163.6(9) . . . . ? O5 Cu1 O3 C14 84.4(3) . . . . ? O3 Cu1 O4 C9 15.4(3) . . . . ? N1 Cu1 O4 C9 147.0(6) . . . . ? N2 Cu1 O4 C9 -168.2(3) . . . . ? O5 Cu1 O4 C9 -81.6(3) . . . . ? O4 Cu1 O5 N6 -79.6(3) . . . . ? O3 Cu1 O5 N6 -175.4(3) . . . . ? N1 Cu1 O5 N6 93.3(3) . . . . ? N2 Cu1 O5 N6 11.5(3) . . . . ? O4 Cu1 N1 C11 -136.7(6) . . . . ? O3 Cu1 N1 C11 -5.0(3) . . . . ? N2 Cu1 N1 C11 177.9(3) . . . . ? O5 Cu1 N1 C11 91.4(3) . . . . ? O4 Cu1 N1 C4 47.3(8) . . . . ? O3 Cu1 N1 C4 179.0(2) . . . . ? N2 Cu1 N1 C4 1.9(2) . . . . ? O5 Cu1 N1 C4 -84.6(2) . . . . ? O4 Cu1 N2 C17 12.1(3) . . . . ? O3 Cu1 N2 C17 162.3(8) . . . . ? N1 Cu1 N2 C17 -174.6(3) . . . . ? O5 Cu1 N2 C17 -85.1(3) . . . . ? O4 Cu1 N2 C6 -176.1(3) . . . . ? O3 Cu1 N2 C6 -25.9(11) . . . . ? N1 Cu1 N2 C6 -2.9(3) . . . . ? O5 Cu1 N2 C6 86.6(3) . . . . ? Cu1 O5 N6 O6 60.7(4) . . . . ? Cu1 O5 N6 O7 -119.9(3) . . . . ? C11 N1 C4 C8 1.4(5) . . . . ? Cu1 N1 C4 C8 177.8(3) . . . . ? C11 N1 C4 C6 -177.1(3) . . . . ? Cu1 N1 C4 C6 -0.7(4) . . . . ? C19 C3 C5 C6 -2.1(5) . . . . ? C19 C3 C5 C12 177.9(4) . . . . ? C17 N2 C6 C5 -1.5(6) . . . . ? Cu1 N2 C6 C5 -174.0(3) . . . . ? C17 N2 C6 C4 175.9(3) . . . . ? Cu1 N2 C6 C4 3.4(4) . . . . ? C3 C5 C6 N2 2.7(5) . . . . ? C12 C5 C6 N2 -177.3(3) . . . . ? C3 C5 C6 C4 -174.6(3) . . . . ? C12 C5 C6 C4 5.5(5) . . . . ? N1 C4 C6 N2 -1.8(5) . . . . ? C8 C4 C6 N2 179.7(3) . . . . ? N1 C4 C6 C5 175.6(3) . . . . ? C8 C4 C6 C5 -2.9(6) . . . . ? C10 N3 C7 C12 -0.9(4) . . . . ? C10 N3 C7 C8 -178.9(4) . . . . ? N1 C4 C8 C18 -1.6(5) . . . . ? C6 C4 C8 C18 176.8(3) . . . . ? N1 C4 C8 C7 -179.9(3) . . . . ? C6 C4 C8 C7 -1.5(5) . . . . ? N3 C7 C8 C4 -179.0(4) . . . . ? C12 C7 C8 C4 3.3(5) . . . . ? N3 C7 C8 C18 2.9(7) . . . . ? C12 C7 C8 C18 -174.8(4) . . . . ? Cu1 O4 C9 C21 -9.2(6) . . . . ? Cu1 O4 C9 C24 172.1(3) . . . . ? C12 N4 C10 N3 -0.3(4) . . . . ? C12 N4 C10 C15 178.6(3) . . . . ? C7 N3 C10 N4 0.7(4) . . . . ? C7 N3 C10 C15 -178.2(3) . . . . ? C4 N1 C11 C2 0.0(5) . . . . ? Cu1 N1 C11 C2 -175.9(3) . . . . ? C18 C2 C11 N1 -1.1(6) . . . . ? C10 N4 C12 C7 -0.3(4) . . . . ? C10 N4 C12 C5 179.3(4) . . . . ? N3 C7 C12 N4 0.7(4) . . . . ? C8 C7 C12 N4 178.9(3) . . . . ? N3 C7 C12 C5 -178.9(3) . . . . ? C8 C7 C12 C5 -0.6(6) . . . . ? C6 C5 C12 N4 176.7(3) . . . . ? C3 C5 C12 N4 -3.3(6) . . . . ? C6 C5 C12 C7 -3.8(5) . . . . ? C3 C5 C12 C7 176.2(4) . . . . ? O1 N5 C13 C20 -100.9(4) . . . . ? O2 N5 C13 C20 77.0(5) . . . . ? O1 N5 C13 C15 78.4(5) . . . . ? O2 N5 C13 C15 -103.6(4) . . . . ? Cu1 O3 C14 C21 5.3(6) . . . . ? Cu1 O3 C14 C23 -176.3(2) . . . . ? C20 C13 C15 C22 0.5(6) . . . . ? N5 C13 C15 C22 -178.8(3) . . . . ? C20 C13 C15 C10 -178.2(4) . . . . ? N5 C13 C15 C10 2.4(6) . . . . ? N4 C10 C15 C13 18.6(6) . . . . ? N3 C10 C15 C13 -162.6(4) . . . . ? N4 C10 C15 C22 -160.1(4) . . . . ? N3 C10 C15 C22 18.7(6) . . . . ? C20 C1 C16 C22 -0.1(6) . . . . ? C6 N2 C17 C19 -0.4(6) . . . . ? Cu1 N2 C17 C19 171.0(3) . . . . ? C11 C2 C18 C8 0.8(5) . . . . ? C4 C8 C18 C2 0.5(5) . . . . ? C7 C8 C18 C2 178.6(3) . . . . ? C5 C3 C19 C17 0.4(6) . . . . ? N2 C17 C19 C3 0.9(6) . . . . ? C15 C13 C20 C1 -2.1(6) . . . . ? N5 C13 C20 C1 177.2(3) . . . . ? C16 C1 C20 C13 1.9(6) . . . . ? O3 C14 C21 C9 6.6(7) . . . . ? C23 C14 C21 C9 -171.8(4) . . . . ? O4 C9 C21 C14 -4.5(7) . . . . ? C24 C9 C21 C14 174.2(4) . . . . ? C1 C16 C22 C15 -1.5(6) . . . . ? C13 C15 C22 C16 1.3(6) . . . . ? C10 C15 C22 C16 -180.0(4) . . . . ? O11 Cu2 O10 C36 16.0(3) . . . . ? N7 Cu2 O10 C36 153.3(8) . . . . ? N8 Cu2 O10 C36 -174.2(3) . . . . ? O12 Cu2 O10 C36 -83.5(3) . . . . ? O10 Cu2 O11 C40 -19.5(3) . . . . ? N7 Cu2 O11 C40 166.1(3) . . . . ? N8 Cu2 O11 C40 -139.7(6) . . . . ? O12 Cu2 O11 C40 77.4(3) . . . . ? O11 Cu2 O12 N12 15.5(3) . . . . ? O10 Cu2 O12 N12 111.5(3) . . . . ? N7 Cu2 O12 N12 -75.4(3) . . . . ? N8 Cu2 O12 N12 -157.3(3) . . . . ? O11 Cu2 N7 C31 -14.4(3) . . . . ? O10 Cu2 N7 C31 -151.9(8) . . . . ? N8 Cu2 N7 C31 175.3(3) . . . . ? O12 Cu2 N7 C31 84.5(3) . . . . ? O11 Cu2 N7 C25 173.3(3) . . . . ? O10 Cu2 N7 C25 35.8(10) . . . . ? N8 Cu2 N7 C25 3.0(3) . . . . ? O12 Cu2 N7 C25 -87.8(3) . . . . ? O11 Cu2 N8 C39 125.6(6) . . . . ? O10 Cu2 N8 C39 5.1(3) . . . . ? N7 Cu2 N8 C39 -179.3(3) . . . . ? O12 Cu2 N8 C39 -91.0(3) . . . . ? O11 Cu2 N8 C30 -57.4(7) . . . . ? O10 Cu2 N8 C30 -178.0(3) . . . . ? N7 Cu2 N8 C30 -2.4(3) . . . . ? O12 Cu2 N8 C30 86.0(3) . . . . ? Cu2 O12 N12 O14 25.8(5) . . . . ? Cu2 O12 N12 O13 -152.4(3) . . . . ? C31 N7 C25 C38 1.9(6) . . . . ? Cu2 N7 C25 C38 174.9(3) . . . . ? C31 N7 C25 C30 -176.0(3) . . . . ? Cu2 N7 C25 C30 -3.0(4) . . . . ? C39 C26 C27 C33 1.1(6) . . . . ? C29 N9 C28 N10 -0.3(4) . . . . ? C29 N9 C28 C41 -176.0(4) . . . . ? C34 N10 C28 N9 -0.2(4) . . . . ? C34 N10 C28 C41 175.8(4) . . . . ? C28 N9 C29 C34 0.6(4) . . . . ? C28 N9 C29 C38 -178.1(4) . . . . ? C39 N8 C30 C33 0.2(6) . . . . ? Cu2 N8 C30 C33 -177.1(3) . . . . ? C39 N8 C30 C25 178.7(3) . . . . ? Cu2 N8 C30 C25 1.5(4) . . . . ? N7 C25 C30 N8 1.1(5) . . . . ? C38 C25 C30 N8 -176.9(3) . . . . ? N7 C25 C30 C33 179.6(3) . . . . ? C38 C25 C30 C33 1.6(6) . . . . ? C25 N7 C31 C44 0.0(6) . . . . ? Cu2 N7 C31 C44 -171.9(3) . . . . ? O8 N11 C32 C45 -68.5(5) . . . . ? O9 N11 C32 C45 108.9(4) . . . . ? O8 N11 C32 C41 113.0(4) . . . . ? O9 N11 C32 C41 -69.7(5) . . . . ? N8 C30 C33 C27 -1.2(6) . . . . ? C25 C30 C33 C27 -179.6(3) . . . . ? N8 C30 C33 C34 178.7(3) . . . . ? C25 C30 C33 C34 0.3(5) . . . . ? C26 C27 C33 C30 0.5(5) . . . . ? C26 C27 C33 C34 -179.4(4) . . . . ? C28 N10 C34 C29 0.5(4) . . . . ? C28 N10 C34 C33 179.7(4) . . . . ? N9 C29 C34 N10 -0.7(4) . . . . ? C38 C29 C34 N10 178.1(3) . . . . ? N9 C29 C34 C33 -180.0(3) . . . . ? C38 C29 C34 C33 -1.2(6) . . . . ? C30 C33 C34 N10 -179.5(4) . . . . ? C27 C33 C34 N10 0.4(7) . . . . ? C30 C33 C34 C29 -0.5(6) . . . . ? C27 C33 C34 C29 179.4(4) . . . . ? Cu2 O10 C36 C37 -6.1(6) . . . . ? Cu2 O10 C36 C48 175.8(3) . . . . ? O10 C36 C37 C40 -6.9(7) . . . . ? C48 C36 C37 C40 171.1(4) . . . . ? N7 C25 C38 C43 -2.6(6) . . . . ? C30 C25 C38 C43 175.2(4) . . . . ? N7 C25 C38 C29 179.0(3) . . . . ? C30 C25 C38 C29 -3.2(6) . . . . ? N9 C29 C38 C43 3.3(7) . . . . ? C34 C29 C38 C43 -175.2(4) . . . . ? N9 C29 C38 C25 -178.4(4) . . . . ? C34 C29 C38 C25 3.0(6) . . . . ? C30 N8 C39 C26 1.5(6) . . . . ? Cu2 N8 C39 C26 178.3(3) . . . . ? C27 C26 C39 N8 -2.2(6) . . . . ? Cu2 O11 C40 C37 13.1(6) . . . . ? Cu2 O11 C40 C47 -167.3(3) . . . . ? C36 C37 C40 O11 3.2(7) . . . . ? C36 C37 C40 C47 -176.4(4) . . . . ? C45 C32 C41 C35 -0.9(6) . . . . ? N11 C32 C41 C35 177.5(4) . . . . ? C45 C32 C41 C28 174.6(4) . . . . ? N11 C32 C41 C28 -7.0(6) . . . . ? C46 C35 C41 C32 -0.5(6) . . . . ? C46 C35 C41 C28 -176.2(4) . . . . ? N9 C28 C41 C32 -15.5(6) . . . . ? N10 C28 C41 C32 169.1(4) . . . . ? N9 C28 C41 C35 159.8(4) . . . . ? N10 C28 C41 C35 -15.5(6) . . . . ? C25 C38 C43 C44 1.5(6) . . . . ? C29 C38 C43 C44 179.7(4) . . . . ? C38 C43 C44 C31 0.3(6) . . . . ? N7 C31 C44 C43 -1.1(6) . . . . ? C41 C32 C45 C42 1.6(7) . . . . ? N11 C32 C45 C42 -176.8(4) . . . . ? C46 C42 C45 C32 -1.0(6) . . . . ? C41 C35 C46 C42 1.0(7) . . . . ? C45 C42 C46 C35 -0.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.673 _refine_diff_density_min -0.485 _refine_diff_density_rms 0.082 _database_code_depnum_ccdc_archive 'CCDC 859802'