# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 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 _database_code_depnum_ccdc_archive 'CCDC 909388' #TrackingRef '15200_web_deposit_cif_file_0_MariadelDeniz_1352130728.(1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H12 Cu F3 N3 O7 S' _chemical_formula_weight 474.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 '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/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 14.6006(3) _cell_length_b 8.0694(2) _cell_length_c 14.7344(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.067(2) _cell_angle_gamma 90.00 _cell_volume 1718.80(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.835 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 956 _exptl_absorpt_coefficient_mu 3.667 _exptl_absorpt_correction_T_min 0.74211 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_source ? _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.5953 _diffrn_measurement_device ? _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5419 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.99 _diffrn_reflns_theta_max 71.829 _reflns_number_total 3296 _reflns_number_gt 2873 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SIR92, J. Appl. Cryst. 26, 343-350, (1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0627P)^2^+0.4595P] 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 3296 _refine_ls_number_parameters 253 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.92920(2) 0.09566(4) 0.36053(2) 0.03672(13) Uani 1 1 d . . . S1 S 0.97413(4) 0.39344(7) 0.20804(4) 0.04158(16) Uani 1 1 d . . . N1 N 1.04239(13) -0.0109(2) 0.32411(14) 0.0394(4) Uani 1 1 d . . . O1W O 0.84047(12) -0.0322(2) 0.27461(12) 0.0475(4) Uani 1 1 d . . . H1WA H 0.8159 -0.1106 0.3033 0.071 Uiso 1 1 d R . . H1WB H 0.7967 0.0316 0.2490 0.071 Uiso 1 1 d R . . N2 N 1.01857(13) 0.1932(3) 0.45431(14) 0.0405(4) Uani 1 1 d . . . O2 O 1.02951(14) 0.3699(3) 0.58020(13) 0.0552(5) Uani 1 1 d . . . C1 C 1.0475(2) -0.1180(3) 0.2570(2) 0.0489(6) Uani 1 1 d . . . H1 H 0.9931 -0.1591 0.2242 0.059 Uiso 1 1 calc R . . O1 O 1.17714(13) 0.2125(3) 0.50121(16) 0.0653(6) Uani 1 1 d . . . N3 N 0.83997(13) 0.2081(3) 0.43172(13) 0.0388(4) Uani 1 1 d . . . C7 C 0.98579(17) 0.2945(3) 0.51712(16) 0.0409(5) Uani 1 1 d . . . C9 C 0.8336(2) 0.4028(3) 0.55272(19) 0.0498(6) Uani 1 1 d . . . H9 H 0.8642 0.4669 0.6000 0.060 Uiso 1 1 calc R . . C8 C 0.88219(16) 0.3037(3) 0.50057(15) 0.0394(5) Uani 1 1 d . . . C5 C 1.12134(16) 0.0462(3) 0.37303(17) 0.0421(5) Uani 1 1 d . . . C3 C 1.2121(2) -0.1100(4) 0.2822(3) 0.0632(8) Uani 1 1 d . . . H3 H 1.2692 -0.1422 0.2670 0.076 Uiso 1 1 calc R . . C6 C 1.10946(17) 0.1621(3) 0.45081(18) 0.0439(5) Uani 1 1 d . . . O3 O 0.90816(13) 0.3029(3) 0.25279(14) 0.0576(5) Uani 1 1 d . . . C12 C 0.74780(17) 0.2093(4) 0.41446(17) 0.0473(6) Uani 1 1 d . . . H12 H 0.7182 0.1423 0.3680 0.057 Uiso 1 1 calc R . . C4 C 1.20693(18) -0.0008(4) 0.3535(2) 0.0538(7) Uani 1 1 d . . . H4 H 1.2605 0.0403 0.3877 0.065 Uiso 1 1 calc R . . C10 C 0.7380(2) 0.4050(4) 0.5333(2) 0.0585(7) Uani 1 1 d . . . H10 H 0.7034 0.4719 0.5670 0.070 Uiso 1 1 calc R . . C11 C 0.69516(19) 0.3080(4) 0.4641(2) 0.0575(7) Uani 1 1 d . . . H11 H 0.6310 0.3081 0.4504 0.069 Uiso 1 1 calc R . . C2 C 1.1316(2) -0.1704(4) 0.2342(2) 0.0598(7) Uani 1 1 d . . . H2 H 1.1336 -0.2460 0.1869 0.072 Uiso 1 1 calc R . . O4 O 0.94572(16) 0.5591(3) 0.18366(17) 0.0653(6) Uani 1 1 d . . . O5 O 1.06779(14) 0.3705(3) 0.24897(18) 0.0696(6) Uani 1 1 d . . . F3 F 0.8858(2) 0.3095(5) 0.04938(17) 0.1226(11) Uani 1 1 d . . . F2 F 1.0274(2) 0.3536(5) 0.0494(2) 0.1361(14) Uani 1 1 d . . . C13 C 0.9665(3) 0.2888(5) 0.0977(2) 0.0723(9) Uani 1 1 d . . . F1 F 0.9865(3) 0.1315(3) 0.1067(2) 0.1354(14) Uani 1 1 d . . . O2W O 0.70491(14) 0.1481(3) 0.17803(15) 0.0602(5) Uani 1 1 d D . . H2WB H 0.7166 0.1761 0.1214 0.090 Uiso 1 1 d RD . . H2WA H 0.6572 0.0806 0.1646 0.090 Uiso 1 1 d RD . . 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 0.03092(19) 0.0401(2) 0.0380(2) 0.00024(13) 0.00077(13) -0.00319(12) S1 0.0323(3) 0.0428(3) 0.0493(3) 0.0072(2) 0.0047(2) -0.0004(2) N1 0.0355(9) 0.0361(10) 0.0462(11) 0.0056(8) 0.0041(8) 0.0007(8) O1W 0.0418(9) 0.0443(9) 0.0524(10) 0.0000(8) -0.0070(7) -0.0042(7) N2 0.0345(9) 0.0424(10) 0.0427(10) 0.0019(8) -0.0011(7) -0.0037(8) O2 0.0501(11) 0.0636(12) 0.0479(10) -0.0093(9) -0.0069(8) -0.0100(9) C1 0.0477(14) 0.0458(14) 0.0534(15) 0.0016(11) 0.0076(11) 0.0013(11) O1 0.0380(10) 0.0696(14) 0.0820(14) -0.0124(11) -0.0141(9) -0.0034(9) N3 0.0359(9) 0.0451(10) 0.0354(9) 0.0033(8) 0.0056(7) -0.0043(8) C7 0.0453(12) 0.0384(12) 0.0370(11) 0.0054(9) -0.0008(9) -0.0082(10) C9 0.0574(16) 0.0493(14) 0.0431(13) -0.0010(11) 0.0081(11) -0.0012(11) C8 0.0426(12) 0.0405(12) 0.0347(11) 0.0057(9) 0.0045(9) -0.0047(9) C5 0.0354(11) 0.0396(12) 0.0503(13) 0.0125(10) 0.0023(9) -0.0014(9) C3 0.0464(15) 0.0666(19) 0.081(2) 0.0133(16) 0.0229(14) 0.0130(13) C6 0.0389(12) 0.0388(12) 0.0511(13) 0.0078(10) -0.0038(10) -0.0041(10) O3 0.0456(10) 0.0735(14) 0.0549(11) 0.0186(10) 0.0108(8) -0.0057(9) C12 0.0363(12) 0.0657(16) 0.0398(12) 0.0019(11) 0.0046(9) -0.0064(11) C4 0.0369(12) 0.0548(15) 0.0694(17) 0.0150(13) 0.0067(12) 0.0006(11) C10 0.0564(17) 0.0672(19) 0.0549(16) -0.0022(13) 0.0184(13) 0.0093(13) C11 0.0410(13) 0.078(2) 0.0550(15) 0.0045(14) 0.0129(11) 0.0011(13) C2 0.0587(17) 0.0579(17) 0.0662(17) -0.0009(14) 0.0201(13) 0.0107(14) O4 0.0645(13) 0.0426(10) 0.0857(15) 0.0080(10) 0.0003(11) 0.0049(9) O5 0.0345(10) 0.0811(15) 0.0899(16) 0.0148(13) -0.0022(10) 0.0017(10) F3 0.124(2) 0.165(3) 0.0671(14) -0.0264(17) -0.0282(14) 0.023(2) F2 0.159(3) 0.170(3) 0.0991(19) 0.039(2) 0.088(2) 0.050(2) C13 0.093(3) 0.071(2) 0.0555(17) 0.0061(16) 0.0193(17) 0.0226(19) F1 0.245(4) 0.0717(15) 0.0866(17) -0.0124(14) 0.014(2) 0.044(2) O2W 0.0513(11) 0.0631(12) 0.0601(12) -0.0021(10) -0.0139(9) 0.0035(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 N2 1.9303(19) . ? Cu1 O1W 1.9712(17) . ? Cu1 N3 2.001(2) . ? Cu1 N1 2.002(2) . ? Cu1 O3 2.297(2) . ? S1 O5 1.427(2) . ? S1 O4 1.431(2) . ? S1 O3 1.4402(19) . ? S1 C13 1.821(4) . ? N1 C1 1.324(4) . ? N1 C5 1.352(3) . ? N2 C6 1.359(3) . ? N2 C7 1.370(3) . ? O2 C7 1.214(3) . ? C1 C2 1.383(4) . ? O1 C6 1.219(3) . ? N3 C12 1.334(3) . ? N3 C8 1.352(3) . ? C7 C8 1.500(3) . ? C9 C8 1.373(4) . ? C9 C10 1.385(4) . ? C5 C4 1.374(4) . ? C5 C6 1.508(4) . ? C3 C2 1.373(5) . ? C3 C4 1.382(5) . ? C12 C11 1.384(4) . ? C10 C11 1.366(5) . ? F3 C13 1.300(5) . ? F2 C13 1.321(5) . ? C13 F1 1.305(4) . ? 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 N2 Cu1 O1W 172.14(8) . . ? N2 Cu1 N3 82.20(8) . . ? O1W Cu1 N3 99.01(8) . . ? N2 Cu1 N1 82.32(9) . . ? O1W Cu1 N1 95.50(8) . . ? N3 Cu1 N1 163.33(8) . . ? N2 Cu1 O3 102.08(8) . . ? O1W Cu1 O3 85.71(8) . . ? N3 Cu1 O3 89.90(8) . . ? N1 Cu1 O3 99.37(8) . . ? O5 S1 O4 117.02(15) . . ? O5 S1 O3 113.80(13) . . ? O4 S1 O3 113.57(14) . . ? O5 S1 C13 104.58(17) . . ? O4 S1 C13 103.30(16) . . ? O3 S1 C13 102.27(17) . . ? C1 N1 C5 119.2(2) . . ? C1 N1 Cu1 128.02(18) . . ? C5 N1 Cu1 112.66(17) . . ? C6 N2 C7 124.9(2) . . ? C6 N2 Cu1 117.60(17) . . ? C7 N2 Cu1 117.49(16) . . ? N1 C1 C2 121.7(3) . . ? C12 N3 C8 118.7(2) . . ? C12 N3 Cu1 128.09(17) . . ? C8 N3 Cu1 112.97(15) . . ? O2 C7 N2 128.3(2) . . ? O2 C7 C8 120.6(2) . . ? N2 C7 C8 111.09(19) . . ? C8 C9 C10 118.5(3) . . ? N3 C8 C9 122.3(2) . . ? N3 C8 C7 115.9(2) . . ? C9 C8 C7 121.8(2) . . ? N1 C5 C4 121.8(3) . . ? N1 C5 C6 115.8(2) . . ? C4 C5 C6 122.3(2) . . ? C2 C3 C4 118.9(3) . . ? O1 C6 N2 128.9(3) . . ? O1 C6 C5 120.0(2) . . ? N2 C6 C5 111.1(2) . . ? S1 O3 Cu1 130.73(12) . . ? N3 C12 C11 121.6(3) . . ? C5 C4 C3 118.9(3) . . ? C11 C10 C9 119.3(3) . . ? C10 C11 C12 119.6(3) . . ? C3 C2 C1 119.4(3) . . ? F3 C13 F1 110.7(4) . . ? F3 C13 F2 106.3(3) . . ? F1 C13 F2 106.3(4) . . ? F3 C13 S1 111.5(3) . . ? F1 C13 S1 112.1(3) . . ? F2 C13 S1 109.6(3) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 71.829 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.268 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.066 data_shelxl2 _database_code_depnum_ccdc_archive 'CCDC 909389' #TrackingRef '15201_web_deposit_cif_file_1_MariadelDeniz_1352130728.(2).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H44 Cu2 N6 O13' _chemical_formula_weight 967.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz '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, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.5694(7) _cell_length_b 10.23660(10) _cell_length_c 20.1856(5) _cell_angle_alpha 90.00 _cell_angle_beta 134.242(4) _cell_angle_gamma 90.00 _cell_volume 4229.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 1.867 _exptl_absorpt_correction_T_min 0.60333 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_source ? _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.5953 _diffrn_measurement_device ? _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12723 _diffrn_reflns_av_R_equivalents 0.0133 _diffrn_reflns_av_sigmaI/netI 0.0117 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.32 _diffrn_reflns_theta_max 73.50 _reflns_number_total 4151 _reflns_number_gt 3955 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0620P)^2^+3.3223P] 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 4151 _refine_ls_number_parameters 288 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0369 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.087834(12) 0.20248(2) 0.975227(16) 0.03336(11) Uani 1 1 d . . . N1 N 0.08950(7) 0.03408(14) 0.92549(10) 0.0369(3) Uani 1 1 d . . . N2 N 0.08388(7) 0.08225(13) 1.04545(10) 0.0351(3) Uani 1 1 d . . . N3 N 0.08901(7) 0.33406(14) 1.05011(10) 0.0372(3) Uani 1 1 d . . . O3 O 0.09940(6) 0.31872(14) 0.91188(9) 0.0449(3) Uani 1 1 d . . . O1W O -0.02749(7) 0.20820(16) 0.85507(11) 0.0590(4) Uani 1 1 d D . . H1WA H -0.0359 0.2384 0.8087 0.089 Uiso 1 1 d RD . . H1WB H -0.0484 0.1348 0.8407 0.089 Uiso 1 1 d RD . . O1 O 0.07057(8) -0.13766(12) 1.05689(11) 0.0522(4) Uani 1 1 d . . . O2 O 0.08128(9) 0.07551(14) 1.15753(11) 0.0610(4) Uani 1 1 d . . . O4 O 0.20289(7) 0.33032(18) 1.04246(11) 0.0627(4) Uani 1 1 d . . . C1 C 0.09301(10) 0.0187(2) 0.86327(13) 0.0459(4) Uani 1 1 d . . . H1 H 0.0989 0.0919 0.8425 0.055 Uiso 1 1 calc R . . C2 C 0.08814(12) -0.1023(2) 0.82892(15) 0.0568(5) Uani 1 1 d . . . H2 H 0.0909 -0.1105 0.7859 0.068 Uiso 1 1 calc R . . C3 C 0.07916(13) -0.2102(2) 0.85896(18) 0.0593(6) Uani 1 1 d . . . H3 H 0.0750 -0.2925 0.8358 0.071 Uiso 1 1 calc R . . C4 C 0.07627(11) -0.19554(19) 0.92444(16) 0.0503(5) Uani 1 1 d . . . H4 H 0.0707 -0.2676 0.9464 0.060 Uiso 1 1 calc R . . C5 C 0.08182(8) -0.07195(17) 0.95598(12) 0.0376(4) Uani 1 1 d . . . C6 C 0.07844(8) -0.04740(16) 1.02640(12) 0.0363(3) Uani 1 1 d . . . C7 C 0.08215(9) 0.13342(17) 1.10586(12) 0.0379(4) Uani 1 1 d . . . C8 C 0.08265(9) 0.28067(16) 1.10428(12) 0.0370(4) Uani 1 1 d . . . C9 C 0.07701(11) 0.3548(2) 1.15495(13) 0.0479(4) Uani 1 1 d . . . H9 H 0.0722 0.3152 1.1914 0.058 Uiso 1 1 calc R . . C10 C 0.07863(12) 0.4895(2) 1.15101(15) 0.0568(5) Uani 1 1 d . . . H10 H 0.0743 0.5419 1.1841 0.068 Uiso 1 1 calc R . . C11 C 0.08670(12) 0.5446(2) 1.09738(16) 0.0588(5) Uani 1 1 d . . . H11 H 0.0888 0.6349 1.0946 0.071 Uiso 1 1 calc R . . C12 C 0.09167(11) 0.46437(18) 1.04812(14) 0.0489(4) Uani 1 1 d . . . H12 H 0.0971 0.5020 1.0119 0.059 Uiso 1 1 calc R . . C13 C 0.15847(9) 0.35633(17) 0.96052(13) 0.0411(4) Uani 1 1 d . . . C14 C 0.16811(10) 0.4318(2) 0.90577(15) 0.0548(5) Uani 1 1 d . . . H14A H 0.1556 0.3758 0.8568 0.066 Uiso 1 1 calc R . . H14B H 0.1386 0.5060 0.8767 0.066 Uiso 1 1 calc R . . C15 C 0.23544(11) 0.4805(3) 0.95993(15) 0.0586(6) Uani 1 1 d . . . H15A H 0.2652 0.4068 0.9877 0.070 Uiso 1 1 calc R . . H15B H 0.2486 0.5360 1.0096 0.070 Uiso 1 1 calc R . . C16 C 0.24091(9) 0.5570(2) 0.90135(14) 0.0478(4) Uani 1 1 d . . . C17 C 0.25243(11) 0.4937(2) 0.85364(16) 0.0566(5) Uani 1 1 d . . . H17 H 0.2559 0.4032 0.8564 0.068 Uiso 1 1 calc R . . C18 C 0.25880(12) 0.5632(3) 0.80202(18) 0.0647(6) Uani 1 1 d . . . H18 H 0.2665 0.5191 0.7701 0.078 Uiso 1 1 calc R . . C19 C 0.25401(13) 0.6964(3) 0.79700(19) 0.0685(7) Uani 1 1 d . . . H19 H 0.2592 0.7428 0.7629 0.082 Uiso 1 1 calc R . . C20 C 0.24149(14) 0.7607(3) 0.8427(2) 0.0715(7) Uani 1 1 d . . . H20 H 0.2380 0.8513 0.8396 0.086 Uiso 1 1 calc R . . C21 C 0.23403(13) 0.6910(2) 0.89367(17) 0.0605(6) Uani 1 1 d G . . H21 H 0.2243 0.7351 0.9231 0.073 Uiso 1 1 calc R . . O2W O 0.33688(8) 0.3537(2) 1.20230(13) 0.0845(6) Uani 1 1 d D . . H2WA H 0.2934 0.3585 1.1557 0.127 Uiso 1 1 d RD . . H2WB H 0.3454 0.4000 1.2459 0.127 Uiso 1 1 d RD . . O3W O 0.0000 0.4742(3) 0.7500 0.0880(9) Uani 1 2 d SD . . H3WA H -0.0171 0.4142 0.7066 0.132 Uiso 0.50 1 d PRD . . H3WB H -0.0344 0.5005 0.7404 0.132 Uiso 0.50 1 d PRD . . 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 0.04268(17) 0.02986(16) 0.03803(16) 0.00279(8) 0.03200(14) -0.00203(8) N1 0.0427(7) 0.0383(7) 0.0416(7) 0.0005(6) 0.0337(6) -0.0007(6) N2 0.0489(8) 0.0280(6) 0.0430(7) 0.0035(5) 0.0375(7) 0.0011(6) N3 0.0456(8) 0.0305(7) 0.0382(7) 0.0021(6) 0.0302(7) -0.0009(6) O3 0.0463(7) 0.0488(7) 0.0456(7) 0.0083(6) 0.0342(6) -0.0058(5) O1W 0.0485(8) 0.0680(10) 0.0536(8) 0.0055(7) 0.0330(7) -0.0061(6) O1 0.0845(10) 0.0308(6) 0.0765(9) 0.0054(6) 0.0690(9) -0.0006(6) O2 0.1137(13) 0.0410(7) 0.0690(9) 0.0053(7) 0.0788(10) -0.0002(8) O4 0.0463(8) 0.0809(11) 0.0531(8) 0.0182(8) 0.0318(7) -0.0013(7) C1 0.0538(10) 0.0531(11) 0.0463(9) -0.0015(8) 0.0407(9) -0.0019(8) C2 0.0693(13) 0.0652(13) 0.0558(11) -0.0080(10) 0.0510(11) 0.0008(10) C3 0.0781(15) 0.0493(12) 0.0662(14) -0.0089(9) 0.0562(13) 0.0037(10) C4 0.0666(13) 0.0375(10) 0.0629(12) -0.0014(8) 0.0511(11) 0.0012(8) C5 0.0421(8) 0.0353(9) 0.0447(9) 0.0005(7) 0.0337(8) 0.0008(6) C6 0.0441(8) 0.0314(8) 0.0456(9) 0.0027(7) 0.0359(8) 0.0010(6) C7 0.0492(9) 0.0338(9) 0.0396(8) 0.0028(7) 0.0343(8) 0.0005(7) C8 0.0437(9) 0.0327(8) 0.0355(8) 0.0026(6) 0.0280(8) 0.0013(6) C9 0.0648(12) 0.0432(10) 0.0434(9) 0.0012(8) 0.0406(9) 0.0043(8) C10 0.0787(14) 0.0413(10) 0.0509(11) -0.0028(8) 0.0454(11) 0.0088(10) C11 0.0811(15) 0.0306(9) 0.0618(12) 0.0005(8) 0.0488(12) 0.0029(9) C12 0.0683(12) 0.0317(9) 0.0524(10) 0.0031(8) 0.0442(10) -0.0012(8) C13 0.0437(9) 0.0387(9) 0.0460(9) 0.0078(7) 0.0332(8) 0.0023(7) C14 0.0460(10) 0.0663(13) 0.0528(11) 0.0145(10) 0.0347(9) -0.0030(9) C15 0.0513(11) 0.0741(15) 0.0512(11) 0.0084(10) 0.0360(10) -0.0110(10) C16 0.0421(9) 0.0561(11) 0.0469(10) 0.0058(8) 0.0317(8) -0.0060(8) C17 0.0602(12) 0.0549(12) 0.0688(13) 0.0059(10) 0.0502(11) 0.0005(9) C18 0.0669(14) 0.0821(17) 0.0704(14) 0.0047(12) 0.0571(13) 0.0010(12) C19 0.0731(15) 0.0824(18) 0.0688(15) 0.0177(12) 0.0564(14) -0.0047(12) C20 0.0874(17) 0.0508(13) 0.0789(17) 0.0115(12) 0.0590(15) -0.0043(12) C21 0.0729(15) 0.0622(14) 0.0586(13) -0.0006(10) 0.0504(12) -0.0026(10) O2W 0.0529(9) 0.1146(17) 0.0671(11) -0.0252(11) 0.0349(9) -0.0014(10) O3W 0.0655(15) 0.0670(16) 0.0706(16) 0.000 0.0251(13) 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 O3 1.9364(12) . ? Cu1 N2 1.9391(13) . ? Cu1 N3 2.0073(15) . ? Cu1 N1 2.0121(15) . ? Cu1 O1W 2.3645(15) . ? N1 C1 1.337(2) . ? N1 C5 1.339(2) . ? N2 C7 1.360(2) . ? N2 C6 1.360(2) . ? N3 C12 1.338(2) . ? N3 C8 1.344(2) . ? O3 C13 1.284(2) . ? O1 C6 1.215(2) . ? O2 C7 1.215(2) . ? O4 C13 1.220(2) . ? C1 C2 1.378(3) . ? C2 C3 1.368(3) . ? C3 C4 1.389(3) . ? C4 C5 1.375(3) . ? C5 C6 1.511(2) . ? C7 C8 1.508(2) . ? C8 C9 1.370(3) . ? C9 C10 1.384(3) . ? C10 C11 1.376(3) . ? C11 C12 1.371(3) . ? C13 C14 1.523(3) . ? C14 C15 1.486(3) . ? C15 C16 1.514(3) . ? C16 C17 1.378(3) . ? C16 C21 1.379(3) . ? C17 C18 1.375(3) . ? C18 C19 1.367(4) . ? C19 C20 1.369(4) . ? C20 C21 1.385(3) . ? 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 O3 Cu1 N2 175.22(6) . . ? O3 Cu1 N3 99.44(7) . . ? N2 Cu1 N3 81.63(6) . . ? O3 Cu1 N1 97.05(6) . . ? N2 Cu1 N1 81.64(6) . . ? N3 Cu1 N1 163.10(6) . . ? O3 Cu1 O1W 93.73(6) . . ? N2 Cu1 O1W 90.88(6) . . ? N3 Cu1 O1W 92.01(6) . . ? N1 Cu1 O1W 90.60(6) . . ? C1 N1 C5 118.67(16) . . ? C1 N1 Cu1 127.80(13) . . ? C5 N1 Cu1 113.37(11) . . ? C7 N2 C6 124.12(14) . . ? C7 N2 Cu1 117.92(11) . . ? C6 N2 Cu1 117.79(11) . . ? C12 N3 C8 118.21(16) . . ? C12 N3 Cu1 128.15(13) . . ? C8 N3 Cu1 113.53(12) . . ? C13 O3 Cu1 114.72(11) . . ? N1 C1 C2 122.07(19) . . ? C3 C2 C1 119.13(19) . . ? C2 C3 C4 119.27(19) . . ? C5 C4 C3 118.42(19) . . ? N1 C5 C4 122.41(17) . . ? N1 C5 C6 115.84(15) . . ? C4 C5 C6 121.74(17) . . ? O1 C6 N2 128.61(16) . . ? O1 C6 C5 120.38(16) . . ? N2 C6 C5 111.00(14) . . ? O2 C7 N2 128.13(17) . . ? O2 C7 C8 120.80(16) . . ? N2 C7 C8 111.07(14) . . ? N3 C8 C9 122.38(17) . . ? N3 C8 C7 115.62(15) . . ? C9 C8 C7 122.00(16) . . ? C8 C9 C10 118.86(19) . . ? C11 C10 C9 119.0(2) . . ? C12 C11 C10 118.93(19) . . ? N3 C12 C11 122.59(19) . . ? O4 C13 O3 122.72(17) . . ? O4 C13 C14 123.42(17) . . ? O3 C13 C14 113.83(16) . . ? C15 C14 C13 115.66(17) . . ? C14 C15 C16 112.62(17) . . ? C17 C16 C21 118.3(2) . . ? C17 C16 C15 120.5(2) . . ? C21 C16 C15 121.2(2) . . ? C18 C17 C16 120.6(2) . . ? C19 C18 C17 120.9(2) . . ? C18 C19 C20 119.3(2) . . ? C19 C20 C21 120.1(2) . . ? C16 C21 C20 120.8(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WB O2 0.87 2.36 3.212(2) 165.1 5_557 O1W H1WB O2W 0.87 2.40 2.873(2) 114.0 8_455 O2W H2WA O4 0.89 1.94 2.808(2) 164.8 . O2W H2WB O2 0.87 2.39 3.065(3) 134.5 4_557 O3W H3WA O3 0.89 2.09 2.885(2) 149.3 2_556 _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 73.50 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.376 _refine_diff_density_min -0.459 _refine_diff_density_rms 0.069 data_cocu _database_code_depnum_ccdc_archive 'CCDC 909390' #TrackingRef '15202_web_deposit_cif_file_2_MariadelDeniz_1352130728.(3).cif' _audit_creation_date 2012-10-23T11:49:29-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C34 H24 Cu3 N8 O12' _chemical_formula_weight 927.23 _chemical_formula_moiety 'C34 H22 Cu3 N8 O11, 0.5(H4 O2)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_space_group_name_hall '-P 1' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.6502(3) _cell_length_b 13.4289(4) _cell_length_c 13.6461(5) _cell_angle_alpha 61.971(3) _cell_angle_beta 65.206(3) _cell_angle_gamma 80.022(3) _cell_volume 1710.05(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.3181 _exptl_crystal_size_mid 0.1624 _exptl_crystal_size_min 0.0174 _exptl_crystal_density_diffrn 1.801 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 934 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.639 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.4186 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_unetI/netI 0.0253 _diffrn_reflns_number 28877 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 6982 _reflns_number_gt 5451 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^)+(0.0464P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 6982 _refine_ls_number_parameters 542 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0767 _refine_ls_wR_factor_gt 0.0747 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.784 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.055 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 0.72708(2) 0.78419(2) 0.10709(2) 0.03291(8) Uani 1 1 d . . . Cu2 Cu 1.06860(2) 0.48045(2) 0.22443(2) 0.03922(9) Uani 1 1 d . . . Cu3 Cu 1.33554(2) 0.156365(19) 0.42885(2) 0.02888(8) Uani 1 1 d . . . O2 O 0.7464(2) 1.11404(15) -0.11536(17) 0.0743(6) Uani 1 1 d . . . O9 O 1.2378(2) -0.16754(14) 0.66796(17) 0.0687(6) Uani 1 1 d . . . C32 C 1.5677(3) 0.2405(3) 0.5947(3) 0.0719(9) Uani 1 1 d . . . H32 H 1.6073 0.2548 0.6335 0.086 Uiso 1 1 calc R . . O6 O 1.24369(13) 0.42657(13) 0.18701(13) 0.0416(4) Uani 1 1 d . . . O4 O 0.74852(13) 0.64895(12) 0.24325(12) 0.0355(3) Uani 1 1 d . . . O8 O 1.15644(13) 0.24995(11) 0.49831(12) 0.0323(3) Uani 1 1 d . . . O3 O 0.91240(14) 0.71254(12) 0.01009(12) 0.0409(4) Uani 1 1 d . . . O7 O 1.35394(13) 0.29588(12) 0.28194(12) 0.0331(3) Uani 1 1 d . . . O5 O 1.05691(15) 0.59717(14) 0.07104(13) 0.0497(4) Uani 1 1 d . . . N6 N 1.23956(16) 0.06778(15) 0.40101(16) 0.0341(4) Uani 1 1 d . . . C17 C 0.7066(2) 0.45201(19) 0.6207(2) 0.0413(5) Uani 1 1 d . . . H17 H 0.6301 0.4682 0.6703 0.05 Uiso 1 1 calc R . . C11 C 0.5112(2) 0.5759(2) 0.0815(2) 0.0515(6) Uani 1 1 d . . . H11 H 0.4935 0.4996 0.112 0.062 Uiso 1 1 calc R . . C27 C 1.2101(2) -0.03873(18) 0.4888(2) 0.0383(5) Uani 1 1 d . . . N1 N 0.61739(17) 0.71833(16) 0.07110(16) 0.0374(4) Uani 1 1 d . . . O10 O 1.40897(19) -0.07861(16) 0.71343(16) 0.0686(6) Uani 1 1 d . . . N7 N 1.33055(17) 0.01202(15) 0.56279(16) 0.0360(4) Uani 1 1 d . . . C10 C 0.4587(3) 0.6562(3) 0.0049(3) 0.0582(7) Uani 1 1 d . . . H10 H 0.4027 0.6352 -0.0151 0.07 Uiso 1 1 calc R . . N2 N 0.69285(19) 0.92243(15) -0.01098(17) 0.0403(5) Uani 1 1 d . . . N8 N 1.44471(16) 0.19973(15) 0.48315(16) 0.0355(4) Uani 1 1 d . . . C26 C 1.1394(2) -0.1114(2) 0.4900(3) 0.0556(7) Uani 1 1 d . . . H26 H 1.1204 -0.1845 0.5517 0.067 Uiso 1 1 calc R . . C3 C 0.9051(3) 1.0594(2) 0.1336(2) 0.0553(7) Uani 1 1 d . . . H3 H 0.94 1.1163 0.1342 0.066 Uiso 1 1 calc R . . C2 C 0.9033(2) 0.9488(2) 0.2161(2) 0.0509(6) Uani 1 1 d . . . H2 H 0.9366 0.93 0.2736 0.061 Uiso 1 1 calc R . . N4 N 0.90499(16) 0.53220(14) 0.29647(14) 0.0319(4) Uani 1 1 d . . . N3 N 0.80266(17) 0.89055(15) 0.13122(16) 0.0359(4) Uani 1 1 d . . . N5 N 1.04981(16) 0.39067(14) 0.38894(15) 0.0321(4) Uani 1 1 d . . . C6 C 0.7436(2) 1.0198(2) -0.0358(2) 0.0453(6) Uani 1 1 d . . . O1 O 0.57060(19) 0.99503(16) -0.12608(16) 0.0632(5) Uani 1 1 d . . . C9 C 0.4897(2) 0.7677(3) -0.0419(2) 0.0536(7) Uani 1 1 d . . . H9 H 0.4575 0.8231 -0.0965 0.064 Uiso 1 1 calc R . . C33 C 1.5635(3) 0.3235(3) 0.4878(3) 0.0694(9) Uani 1 1 d . . . H33 H 1.602 0.3939 0.4524 0.083 Uiso 1 1 calc R . . C24 C 1.1249(3) 0.0340(3) 0.3095(3) 0.0573(7) Uani 1 1 d . . . H24 H 1.0957 0.0606 0.2479 0.069 Uiso 1 1 calc R . . C12 C 0.5900(2) 0.6095(2) 0.1124(2) 0.0447(6) Uani 1 1 d . . . H12 H 0.6259 0.5547 0.1639 0.054 Uiso 1 1 calc R . . C20 C 0.93591(19) 0.40308(16) 0.47415(17) 0.0279(4) Uani 1 1 d . . . C18 C 0.7838(2) 0.37329(19) 0.67133(19) 0.0415(6) Uani 1 1 d . . . H18 H 0.7585 0.3366 0.7546 0.05 Uiso 1 1 calc R . . C25 C 1.0971(3) -0.0749(3) 0.3991(3) 0.0643(8) Uani 1 1 d . . . H25 H 1.0499 -0.1234 0.3981 0.077 Uiso 1 1 calc R . . C15 C 0.85525(19) 0.48257(16) 0.42332(17) 0.0280(4) Uani 1 1 d . . . C19 C 0.8981(2) 0.34877(17) 0.59916(18) 0.0343(5) Uani 1 1 d . . . H19 H 0.9499 0.2961 0.6338 0.041 Uiso 1 1 calc R . . C16 C 0.7418(2) 0.50716(18) 0.49669(18) 0.0352(5) Uani 1 1 d . . . H16 H 0.6895 0.5602 0.4633 0.042 Uiso 1 1 calc R . . C28 C 1.2619(2) -0.07341(19) 0.5843(2) 0.0434(6) Uani 1 1 d . . . C5 C 0.8043(2) 0.99815(18) 0.05139(19) 0.0389(5) Uani 1 1 d . . . C4 C 0.8544(2) 1.0843(2) 0.0502(2) 0.0510(6) Uani 1 1 d . . . H4 H 0.854 1.1584 -0.0062 0.061 Uiso 1 1 calc R . . C34 C 1.5010(2) 0.3005(2) 0.4340(3) 0.0475(6) Uani 1 1 d . . . H34 H 1.498 0.3565 0.3615 0.057 Uiso 1 1 calc R . . C8 C 0.5693(2) 0.7970(2) -0.0072(2) 0.0408(5) Uani 1 1 d . . . C13 C 0.9494(2) 0.64140(18) 0.08902(18) 0.0356(5) Uani 1 1 d . . . C22 C 1.25575(19) 0.35153(17) 0.28116(18) 0.0294(4) Uani 1 1 d . . . C31 C 1.5125(3) 0.1351(3) 0.6444(3) 0.0594(8) Uani 1 1 d . . . H31 H 1.5161 0.0775 0.7157 0.071 Uiso 1 1 calc R . . C23 C 1.1970(2) 0.1030(2) 0.3128(2) 0.0429(6) Uani 1 1 d . . . H23 H 1.2169 0.1764 0.2518 0.052 Uiso 1 1 calc R . . C21 C 1.14437(19) 0.32468(16) 0.40497(18) 0.0278(4) Uani 1 1 d . . . C30 C 1.4522(2) 0.1178(2) 0.5857(2) 0.0398(5) Uani 1 1 d . . . C1 C 0.8520(2) 0.8668(2) 0.2127(2) 0.0416(5) Uani 1 1 d . . . H1 H 0.8513 0.7922 0.2685 0.05 Uiso 1 1 calc R . . C7 C 0.6098(2) 0.9171(2) -0.0559(2) 0.0444(6) Uani 1 1 d . . . C29 C 1.3943(2) 0.0048(2) 0.6301(2) 0.0439(6) Uani 1 1 d . . . C14 C 0.85614(19) 0.60500(17) 0.22194(18) 0.0287(4) Uani 1 1 d . . . O12A O 0.7102(10) 0.3617(8) 0.1446(7) 0.079(4) Uani 0.49(2) 1 d P A 1 O12B O 0.7749(17) 0.3895(6) 0.1624(5) 0.091(5) Uani 0.51(2) 1 d P A 2 O11 O 1.0073(2) 0.33230(19) 0.20051(18) 0.0681(6) Uani 1 1 d D . . H1WA H 0.669(7) 0.300(6) 0.177(7) 0.082 Uiso 0.49(2) 1 d PD A 1 H2WA H 0.783(6) 0.356(6) 0.080(6) 0.082 Uiso 0.49(2) 1 d PD A 1 H1WB H 0.798(7) 0.401(6) 0.101(7) 0.082 Uiso 0.51(2) 1 d PD A 2 H2WB H 0.720(7) 0.309(6) 0.202(6) 0.082 Uiso 0.51(2) 1 d PD A 2 H1W1 H 1.042(3) 0.327(3) 0.1316(16) 0.082 Uiso 1 1 d D . . H2W1 H 0.9277(13) 0.349(3) 0.208(3) 0.082 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.03536(15) 0.03088(15) 0.02963(15) -0.00761(11) -0.02021(12) 0.00979(11) Cu2 0.03147(15) 0.04535(17) 0.02352(14) -0.00519(12) -0.01215(11) 0.01436(12) Cu3 0.03151(14) 0.02630(14) 0.03001(14) -0.00914(11) -0.01876(11) 0.00578(10) O2 0.1223(18) 0.0339(10) 0.0590(12) -0.0002(9) -0.0537(13) 0.0067(10) O9 0.0889(15) 0.0325(10) 0.0557(12) 0.0027(9) -0.0262(11) -0.0035(9) C32 0.071(2) 0.101(3) 0.105(3) -0.078(2) -0.065(2) 0.0377(19) O6 0.0295(8) 0.0455(9) 0.0283(8) -0.0025(7) -0.0112(6) 0.0087(7) O4 0.0326(8) 0.0344(8) 0.0290(8) -0.0064(7) -0.0148(6) 0.0093(6) O8 0.0353(8) 0.0299(8) 0.0276(8) -0.0075(6) -0.0176(6) 0.0086(6) O3 0.0429(9) 0.0398(9) 0.0265(8) -0.0052(7) -0.0164(7) 0.0116(7) O7 0.0263(7) 0.0314(8) 0.0312(8) -0.0056(6) -0.0132(6) 0.0047(6) O5 0.0378(9) 0.0576(11) 0.0264(8) -0.0050(8) -0.0107(7) 0.0184(8) N6 0.0316(10) 0.0339(10) 0.0370(10) -0.0179(9) -0.0112(8) 0.0015(8) C17 0.0439(13) 0.0391(13) 0.0308(12) -0.0160(10) -0.0083(10) 0.0096(10) C11 0.0501(15) 0.0573(16) 0.0472(15) -0.0277(14) -0.0111(12) -0.0053(13) C27 0.0323(12) 0.0311(12) 0.0434(13) -0.0176(11) -0.0077(10) 0.0040(9) N1 0.0344(10) 0.0442(11) 0.0313(10) -0.0140(9) -0.0159(8) 0.0065(8) O10 0.0795(14) 0.0655(13) 0.0432(11) -0.0020(9) -0.0398(10) 0.0178(10) N7 0.0401(10) 0.0314(10) 0.0321(10) -0.0096(8) -0.0182(8) 0.0088(8) C10 0.0482(16) 0.084(2) 0.0600(17) -0.0451(17) -0.0217(13) 0.0014(15) N2 0.0506(12) 0.0330(10) 0.0386(11) -0.0101(9) -0.0297(9) 0.0130(9) N8 0.0336(10) 0.0398(11) 0.0433(11) -0.0219(9) -0.0256(9) 0.0161(8) C26 0.0475(15) 0.0367(14) 0.076(2) -0.0236(14) -0.0180(14) -0.0041(12) C3 0.0529(16) 0.0600(18) 0.0549(17) -0.0330(15) -0.0093(13) -0.0105(13) C2 0.0494(15) 0.0637(17) 0.0439(15) -0.0246(14) -0.0193(12) -0.0024(13) N4 0.0310(9) 0.0336(10) 0.0224(9) -0.0072(8) -0.0110(7) 0.0074(7) N3 0.0381(10) 0.0336(10) 0.0311(10) -0.0115(8) -0.0145(8) 0.0069(8) N5 0.0307(9) 0.0336(10) 0.0254(9) -0.0074(8) -0.0139(8) 0.0069(8) C6 0.0563(15) 0.0368(13) 0.0349(13) -0.0109(11) -0.0213(11) 0.0139(11) O1 0.0871(14) 0.0612(12) 0.0533(11) -0.0201(10) -0.0544(11) 0.0297(10) C9 0.0473(15) 0.082(2) 0.0488(15) -0.0385(15) -0.0296(13) 0.0197(14) C33 0.0624(18) 0.069(2) 0.120(3) -0.060(2) -0.059(2) 0.0197(15) C24 0.0533(16) 0.072(2) 0.0669(18) -0.0408(17) -0.0281(14) -0.0018(14) C12 0.0453(14) 0.0435(14) 0.0392(13) -0.0144(11) -0.0152(11) 0.0005(11) C20 0.0326(11) 0.0250(10) 0.0255(10) -0.0096(9) -0.0135(9) 0.0031(8) C18 0.0541(15) 0.0378(13) 0.0220(11) -0.0101(10) -0.0109(10) 0.0063(11) C25 0.0576(17) 0.0608(19) 0.094(2) -0.0459(19) -0.0307(17) -0.0036(14) C15 0.0319(11) 0.0241(10) 0.0246(10) -0.0072(8) -0.0127(9) 0.0020(8) C19 0.0455(13) 0.0280(11) 0.0299(11) -0.0111(9) -0.0204(10) 0.0096(9) C16 0.0375(12) 0.0309(11) 0.0324(12) -0.0118(10) -0.0148(10) 0.0087(9) C28 0.0444(14) 0.0336(13) 0.0375(13) -0.0119(11) -0.0099(11) 0.0078(10) C5 0.0421(13) 0.0343(12) 0.0318(12) -0.0135(10) -0.0104(10) 0.0071(10) C4 0.0593(16) 0.0392(14) 0.0403(14) -0.0165(12) -0.0076(12) -0.0005(12) C34 0.0471(14) 0.0427(14) 0.0714(18) -0.0309(13) -0.0378(14) 0.0137(11) C8 0.0383(12) 0.0517(15) 0.0345(12) -0.0212(11) -0.0187(10) 0.0148(11) C13 0.0366(12) 0.0342(12) 0.0268(11) -0.0070(9) -0.0141(9) 0.0070(10) C22 0.0306(11) 0.0259(10) 0.0281(11) -0.0059(9) -0.0145(9) -0.0018(9) C31 0.0548(16) 0.092(2) 0.0603(17) -0.0494(17) -0.0429(14) 0.0361(16) C23 0.0455(14) 0.0497(14) 0.0400(13) -0.0212(12) -0.0193(11) -0.0021(11) C21 0.0298(11) 0.0251(10) 0.0314(11) -0.0116(9) -0.0169(9) 0.0039(8) C30 0.0354(12) 0.0549(15) 0.0386(12) -0.0271(12) -0.0229(10) 0.0215(11) C1 0.0438(13) 0.0429(13) 0.0356(12) -0.0134(11) -0.0191(11) 0.0039(11) C7 0.0517(15) 0.0520(15) 0.0342(12) -0.0207(12) -0.0272(11) 0.0226(12) C29 0.0400(13) 0.0514(15) 0.0301(12) -0.0133(11) -0.0166(10) 0.0180(11) C14 0.0300(11) 0.0248(10) 0.0270(11) -0.0077(9) -0.0133(9) 0.0047(8) O12A 0.063(5) 0.069(4) 0.051(3) 0.002(3) -0.012(3) 0.018(4) O12B 0.115(9) 0.063(4) 0.054(3) -0.014(3) -0.018(4) 0.023(4) O11 0.0695(14) 0.0925(16) 0.0557(12) -0.0425(12) -0.0257(11) 0.0037(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N2 1.9163(17) . ? Cu1 O4 1.9682(14) . ? Cu1 N1 1.9958(19) . ? Cu1 N3 2.0111(19) . ? Cu1 O3 2.3280(15) . ? Cu2 N5 1.9175(16) . ? Cu2 N4 1.9221(16) . ? Cu2 O6 1.9767(14) . ? Cu2 O5 1.9845(15) . ? Cu2 O11 2.423(2) . ? Cu3 N7 1.9292(17) . ? Cu3 O7 1.9554(14) . ? Cu3 N8 1.9896(17) . ? Cu3 N6 2.0129(17) . ? Cu3 O8 2.3202(14) . ? O2 C6 1.215(3) . ? O9 C28 1.215(3) . ? C32 C33 1.372(4) . ? C32 C31 1.387(4) . ? C32 H32 0.93 . ? O6 C22 1.254(2) . ? O4 C14 1.267(2) . ? O8 C21 1.245(2) . ? O3 C13 1.240(2) . ? O7 C22 1.254(2) . ? O5 C13 1.266(3) . ? N6 C23 1.342(3) . ? N6 C27 1.347(3) . ? C17 C18 1.382(3) . ? C17 C16 1.387(3) . ? C17 H17 0.93 . ? C11 C12 1.368(3) . ? C11 C10 1.371(4) . ? C11 H11 0.93 . ? C27 C26 1.372(3) . ? C27 C28 1.508(3) . ? N1 C12 1.339(3) . ? N1 C8 1.344(3) . ? O10 C29 1.215(3) . ? N7 C28 1.359(3) . ? N7 C29 1.368(3) . ? C10 C9 1.369(4) . ? C10 H10 0.93 . ? N2 C6 1.362(3) . ? N2 C7 1.372(3) . ? N8 C30 1.341(3) . ? N8 C34 1.341(3) . ? C26 C25 1.371(4) . ? C26 H26 0.93 . ? C3 C2 1.376(4) . ? C3 C4 1.377(4) . ? C3 H3 0.93 . ? C2 C1 1.368(3) . ? C2 H2 0.93 . ? N4 C14 1.293(2) . ? N4 C15 1.409(3) . ? N3 C5 1.337(3) . ? N3 C1 1.345(3) . ? N5 C21 1.315(2) . ? N5 C20 1.397(3) . ? C6 C5 1.520(3) . ? O1 C7 1.216(3) . ? C9 C8 1.382(3) . ? C9 H9 0.93 . ? C33 C34 1.380(4) . ? C33 H33 0.93 . ? C24 C25 1.374(4) . ? C24 C23 1.381(3) . ? C24 H24 0.93 . ? C12 H12 0.93 . ? C20 C19 1.396(3) . ? C20 C15 1.417(3) . ? C18 C19 1.380(3) . ? C18 H18 0.93 . ? C25 H25 0.93 . ? C15 C16 1.381(3) . ? C19 H19 0.93 . ? C16 H16 0.93 . ? C5 C4 1.373(3) . ? C4 H4 0.93 . ? C34 H34 0.93 . ? C8 C7 1.503(4) . ? C13 C14 1.552(3) . ? C22 C21 1.555(3) . ? C31 C30 1.375(3) . ? C31 H31 0.93 . ? C23 H23 0.93 . ? C30 C29 1.507(4) . ? C1 H1 0.93 . ? O12A H1WA 0.85(6) . ? O12A H2WA 0.96(6) . ? O12A H1WB 1.03(7) . ? O12A H2WB 0.81(7) . ? O12B H2WA 1.36(6) . ? O12B H1WB 0.70(8) . ? O12B H2WB 1.13(8) . ? O11 H1W1 0.890(10) . ? O11 H2W1 0.890(10) . ? 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 N2 Cu1 O4 172.86(7) . . ? N2 Cu1 N1 82.55(8) . . ? O4 Cu1 N1 99.70(7) . . ? N2 Cu1 N3 82.39(8) . . ? O4 Cu1 N3 94.21(7) . . ? N1 Cu1 N3 162.40(7) . . ? N2 Cu1 O3 108.52(7) . . ? O4 Cu1 O3 78.17(5) . . ? N1 Cu1 O3 94.18(7) . . ? N3 Cu1 O3 99.21(6) . . ? N5 Cu2 N4 82.99(7) . . ? N5 Cu2 O6 84.34(6) . . ? N4 Cu2 O6 164.45(7) . . ? N5 Cu2 O5 165.65(7) . . ? N4 Cu2 O5 83.76(6) . . ? O6 Cu2 O5 107.78(6) . . ? N5 Cu2 O11 96.29(7) . . ? N4 Cu2 O11 100.28(7) . . ? O6 Cu2 O11 90.02(7) . . ? O5 Cu2 O11 91.47(7) . . ? N7 Cu3 O7 173.86(7) . . ? N7 Cu3 N8 82.51(8) . . ? O7 Cu3 N8 98.66(7) . . ? N7 Cu3 N6 82.00(8) . . ? O7 Cu3 N6 96.15(7) . . ? N8 Cu3 N6 163.49(7) . . ? N7 Cu3 O8 106.89(6) . . ? O7 Cu3 O8 78.99(5) . . ? N8 Cu3 O8 97.45(6) . . ? N6 Cu3 O8 92.47(6) . . ? C33 C32 C31 119.7(2) . . ? C33 C32 H32 120.1 . . ? C31 C32 H32 120.1 . . ? C22 O6 Cu2 110.31(13) . . ? C14 O4 Cu1 116.29(13) . . ? C21 O8 Cu3 104.18(12) . . ? C13 O3 Cu1 106.87(13) . . ? C22 O7 Cu3 116.12(12) . . ? C13 O5 Cu2 111.37(13) . . ? C23 N6 C27 118.18(19) . . ? C23 N6 Cu3 128.74(16) . . ? C27 N6 Cu3 112.95(15) . . ? C18 C17 C16 120.8(2) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C12 C11 C10 119.0(3) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? N6 C27 C26 122.2(2) . . ? N6 C27 C28 115.55(19) . . ? C26 C27 C28 122.2(2) . . ? C12 N1 C8 118.5(2) . . ? C12 N1 Cu1 128.51(16) . . ? C8 N1 Cu1 112.97(16) . . ? C28 N7 C29 125.3(2) . . ? C28 N7 Cu3 117.60(15) . . ? C29 N7 Cu3 117.11(16) . . ? C9 C10 C11 119.3(3) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C6 N2 C7 124.71(19) . . ? C6 N2 Cu1 117.57(15) . . ? C7 N2 Cu1 117.43(16) . . ? C30 N8 C34 119.2(2) . . ? C30 N8 Cu3 113.11(16) . . ? C34 N8 Cu3 127.49(15) . . ? C25 C26 C27 119.2(3) . . ? C25 C26 H26 120.4 . . ? C27 C26 H26 120.4 . . ? C2 C3 C4 118.8(2) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C1 C2 C3 119.3(2) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C14 N4 C15 129.84(17) . . ? C14 N4 Cu2 115.52(14) . . ? C15 N4 Cu2 114.63(13) . . ? C5 N3 C1 118.3(2) . . ? C5 N3 Cu1 112.76(15) . . ? C1 N3 Cu1 128.88(16) . . ? C21 N5 C20 129.62(17) . . ? C21 N5 Cu2 115.37(13) . . ? C20 N5 Cu2 114.99(12) . . ? O2 C6 N2 128.8(2) . . ? O2 C6 C5 120.3(2) . . ? N2 C6 C5 110.86(18) . . ? C10 C9 C8 119.2(2) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C32 C33 C34 118.8(3) . . ? C32 C33 H33 120.6 . . ? C34 C33 H33 120.6 . . ? C25 C24 C23 118.7(3) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? N1 C12 C11 122.5(2) . . ? N1 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? C19 C20 N5 126.96(18) . . ? C19 C20 C15 119.09(19) . . ? N5 C20 C15 113.92(17) . . ? C19 C18 C17 120.5(2) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C26 C25 C24 119.5(2) . . ? C26 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? C16 C15 N4 126.24(18) . . ? C16 C15 C20 120.27(18) . . ? N4 C15 C20 113.46(17) . . ? C18 C19 C20 119.94(19) . . ? C18 C19 H19 120 . . ? C20 C19 H19 120 . . ? C15 C16 C17 119.43(19) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? O9 C28 N7 128.8(2) . . ? O9 C28 C27 119.7(2) . . ? N7 C28 C27 111.50(19) . . ? N3 C5 C4 122.3(2) . . ? N3 C5 C6 115.7(2) . . ? C4 C5 C6 122.0(2) . . ? C5 C4 C3 119.2(2) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? N8 C34 C33 121.8(3) . . ? N8 C34 H34 119.1 . . ? C33 C34 H34 119.1 . . ? N1 C8 C9 121.4(2) . . ? N1 C8 C7 116.0(2) . . ? C9 C8 C7 122.6(2) . . ? O3 C13 O5 125.96(19) . . ? O3 C13 C14 116.93(18) . . ? O5 C13 C14 117.10(18) . . ? O6 C22 O7 123.60(18) . . ? O6 C22 C21 119.23(18) . . ? O7 C22 C21 117.17(17) . . ? C30 C31 C32 118.5(3) . . ? C30 C31 H31 120.8 . . ? C32 C31 H31 120.8 . . ? N6 C23 C24 122.3(2) . . ? N6 C23 H23 118.9 . . ? C24 C23 H23 118.9 . . ? O8 C21 N5 131.19(19) . . ? O8 C21 C22 119.12(17) . . ? N5 C21 C22 109.70(17) . . ? N8 C30 C31 122.0(2) . . ? N8 C30 C29 115.81(19) . . ? C31 C30 C29 122.2(2) . . ? N3 C1 C2 122.2(2) . . ? N3 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? O1 C7 N2 127.7(2) . . ? O1 C7 C8 121.4(2) . . ? N2 C7 C8 110.86(18) . . ? O10 C29 N7 127.7(3) . . ? O10 C29 C30 121.4(2) . . ? N7 C29 C30 110.87(18) . . ? O4 C14 N4 129.47(19) . . ? O4 C14 C13 118.78(17) . . ? N4 C14 C13 111.74(17) . . ? H1WA O12A H2WA 103(5) . . ? H1WA O12A H1WB 146(6) . . ? H2WA O12A H1WB 51(5) . . ? H1WA O12A H2WB 61(6) . . ? H2WA O12A H2WB 101(6) . . ? H1WB O12A H2WB 100(6) . . ? H2WA O12B H1WB 33(6) . . ? H2WA O12B H2WB 66(4) . . ? H1WB O12B H2WB 98(7) . . ? Cu2 O11 H1W1 123(2) . . ? Cu2 O11 H2W1 102(2) . . ? H1W1 O11 H2W1 103(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O11 H1W1 O3 0.890(10) 2.072(12) 2.945(2) 167(3) 2_765 O11 H2W1 O12B 0.890(10) 2.03(3) 2.88(2) 159(3) . data_tmcuc_final _database_code_depnum_ccdc_archive 'CCDC 909391' #TrackingRef '15203_web_deposit_cif_file_3_MariadelDeniz_1352130728.(4).cif' _audit_creation_date 2012-10-23T12:20:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_moiety 'C68 H44 Cu4 N16 O20, 6(H2 O)' _chemical_formula_sum 'C68 H56 Cu4 N16 O26' _chemical_formula_weight 1767.49 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4297(4) _cell_length_b 11.2189(9) _cell_length_c 17.0787(13) _cell_angle_alpha 75.037(7) _cell_angle_beta 80.294(5) _cell_angle_gamma 89.324(5) _cell_volume 1719.6(2) _cell_formula_units_Z 1 _cell_measurement_temperature 260(2) _cell_measurement_reflns_used 10230 _cell_measurement_theta_min 2.7086 _cell_measurement_theta_max 29.6846 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.5032 _exptl_crystal_size_mid 0.087 _exptl_crystal_size_min 0.022 _exptl_crystal_density_diffrn 1.707 _exptl_crystal_F_000 900 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 -1 0.002 0 1 1 0.02 -1 0 0 0.2731 1 0 0 0.2077 0 -1 1 0.0207 0 1 -1 0.0506 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.32 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.523 _exptl_absorpt_correction_T_max 0.946 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 260.00(14) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.4186 _diffrn_orient_matrix_ub_11 0.0212853 _diffrn_orient_matrix_ub_12 -0.0622193 _diffrn_orient_matrix_ub_13 0.0075382 _diffrn_orient_matrix_ub_21 0.0048842 _diffrn_orient_matrix_ub_22 0.0030457 _diffrn_orient_matrix_ub_23 -0.0423764 _diffrn_orient_matrix_ub_31 0.0731646 _diffrn_orient_matrix_ub_32 0.0201745 _diffrn_orient_matrix_ub_33 -0.0071677 _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_unetI/netI 0.035 _diffrn_reflns_number 61078 _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 2.71 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 7869 _reflns_number_gt 6221 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^)+(0.0388P)^2^+1.1694P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 7869 _refine_ls_number_parameters 531 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0914 _refine_ls_wR_factor_gt 0.0842 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.634 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.063 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 O8 O -0.20037(16) -0.25685(16) 0.90997(11) 0.0328(4) Uani 1 1 d . . . O6 O 0.03969(17) -0.15937(17) 1.01639(11) 0.0377(4) Uani 1 1 d . . . N8 N -0.4277(2) -0.3443(2) 1.07757(13) 0.0326(5) Uani 1 1 d . . . O2 O 0.8410(2) 0.35286(18) 0.52505(14) 0.0512(5) Uani 1 1 d . . . O3 O 0.38712(18) -0.02092(16) 0.57272(11) 0.0389(4) Uani 1 1 d . . . O7 O -0.19808(17) -0.14699(17) 1.03255(11) 0.0346(4) Uani 1 1 d . . . N5 N 0.03892(19) -0.28223(18) 0.89985(12) 0.0260(4) Uani 1 1 d . . . H5 H 0.1181 -0.2575 0.9101 0.031 Uiso 1 1 calc R . . O1 O 0.6391(2) 0.47440(17) 0.42927(13) 0.0473(5) Uani 1 1 d . . . O9 O -0.6759(2) -0.13952(18) 0.85401(12) 0.0486(5) Uani 1 1 d . . . O10 O -0.71581(18) -0.37086(17) 0.97501(12) 0.0397(4) Uani 1 1 d . . . O4 O 0.2657(2) 0.03455(19) 0.67953(13) 0.0574(6) Uani 1 1 d . . . N4 N 0.1726(2) -0.21498(18) 0.73327(12) 0.0300(4) Uani 1 1 d . . . H4 H 0.2054 -0.1815 0.7669 0.036 Uiso 1 1 calc R . . O5 O 0.1411(2) -0.17675(18) 0.59984(11) 0.0457(5) Uani 1 1 d . . . N7 N -0.5431(2) -0.21687(19) 0.95710(12) 0.0298(4) Uani 1 1 d . . . C20 C 0.1016(3) -0.4175(2) 0.72076(16) 0.0326(5) Uani 1 1 d . . . H20 H 0.1406 -0.3956 0.665 0.039 Uiso 1 1 calc R . . C16 C 0.0425(2) -0.3667(2) 0.84994(14) 0.0249(5) Uani 1 1 d . . . N3 N 0.6546(2) 0.06624(19) 0.61253(13) 0.0320(5) Uani 1 1 d . . . C23 C -0.2892(3) 0.0771(2) 0.89661(17) 0.0365(6) Uani 1 1 d . . . H23 H -0.2144 0.0747 0.9261 0.044 Uiso 1 1 calc R . . N6 N -0.3799(2) -0.02036(19) 0.91479(13) 0.0307(4) Uani 1 1 d . . . C10 C 0.8792(3) 0.0130(3) 0.69863(19) 0.0499(8) Uani 1 1 d . . . H10 H 0.9549 -0.0051 0.7278 0.06 Uiso 1 1 calc R . . N1 N 0.3759(2) 0.23577(19) 0.47580(13) 0.0312(5) Uani 1 1 d . . . C13 C 0.2887(3) -0.0348(2) 0.63547(15) 0.0317(5) Uani 1 1 d . . . C31 C -0.6009(3) -0.5103(2) 1.11340(17) 0.0377(6) Uani 1 1 d . . . H31 H -0.6803 -0.5473 1.1023 0.045 Uiso 1 1 calc R . . N2 N 0.6229(2) 0.27526(18) 0.51156(13) 0.0322(5) Uani 1 1 d . . . C18 C -0.0154(3) -0.5682(2) 0.83951(17) 0.0359(6) Uani 1 1 d . . . H18 H -0.0542 -0.6475 0.8639 0.043 Uiso 1 1 calc R . . C24 C -0.3040(3) 0.1808(3) 0.83533(19) 0.0433(7) Uani 1 1 d . . . H24 H -0.2391 0.2474 0.8234 0.052 Uiso 1 1 calc R . . C27 C -0.4878(2) -0.0158(2) 0.87135(15) 0.0288(5) Uani 1 1 d . . . C19 C 0.0429(3) -0.5342(2) 0.75726(17) 0.0369(6) Uani 1 1 d . . . H19 H 0.0426 -0.5908 0.726 0.044 Uiso 1 1 calc R . . C6 C 0.5775(3) 0.3752(2) 0.45988(16) 0.0310(5) Uani 1 1 d . . . C29 C -0.6122(2) -0.3284(2) 0.99310(15) 0.0295(5) Uani 1 1 d . . . C26 C -0.5085(3) 0.0853(2) 0.81080(16) 0.0360(6) Uani 1 1 d . . . H26 H -0.5849 0.0865 0.7826 0.043 Uiso 1 1 calc R . . C30 C -0.5447(2) -0.3991(2) 1.06413(15) 0.0311(5) Uani 1 1 d . . . C15 C 0.1031(2) -0.3321(2) 0.76669(14) 0.0257(5) Uani 1 1 d . . . C14 C 0.1923(2) -0.1507(2) 0.65380(15) 0.0302(5) Uani 1 1 d . . . C28 C -0.5815(2) -0.1312(2) 0.89294(15) 0.0311(5) Uani 1 1 d . . . C17 C -0.0160(2) -0.4839(2) 0.88544(15) 0.0321(5) Uani 1 1 d . . . H17 H -0.0562 -0.5064 0.941 0.039 Uiso 1 1 calc R . . C12 C 0.6578(3) -0.0417(3) 0.66724(16) 0.0395(6) Uani 1 1 d . . . H12 H 0.5828 -0.0992 0.6759 0.047 Uiso 1 1 calc R . . C22 C -0.0763(2) -0.1756(2) 0.99876(14) 0.0268(5) Uani 1 1 d . . . C11 C 0.7684(3) -0.0715(3) 0.71175(18) 0.0471(7) Uani 1 1 d . . . H11 H 0.7677 -0.1475 0.75 0.056 Uiso 1 1 calc R . . C4 C 0.3612(3) 0.4394(3) 0.39355(18) 0.0431(7) Uani 1 1 d . . . H4A H 0.4025 0.5183 0.3707 0.052 Uiso 1 1 calc R . . C21 C -0.0843(2) -0.2415(2) 0.93052(14) 0.0253(5) Uani 1 1 d . . . C7 C 0.7495(3) 0.2712(2) 0.54064(17) 0.0336(6) Uani 1 1 d . . . C32 C -0.5373(3) -0.5662(3) 1.17976(19) 0.0483(7) Uani 1 1 d . . . H32 H -0.5736 -0.6417 1.2144 0.058 Uiso 1 1 calc R . . C9 C 0.8774(3) 0.1247(3) 0.64188(19) 0.0440(7) Uani 1 1 d . . . H9 H 0.9522 0.1829 0.632 0.053 Uiso 1 1 calc R . . C5 C 0.4319(2) 0.3502(2) 0.44141(15) 0.0302(5) Uani 1 1 d . . . C1 C 0.2452(3) 0.2092(3) 0.46305(17) 0.0392(6) Uani 1 1 d . . . H1 H 0.2047 0.1305 0.4878 0.047 Uiso 1 1 calc R . . C2 C 0.1690(3) 0.2938(3) 0.41480(19) 0.0476(7) Uani 1 1 d . . . H2 H 0.0791 0.2723 0.4061 0.057 Uiso 1 1 calc R . . C25 C -0.4144(3) 0.1860(3) 0.79184(18) 0.0418(6) Uani 1 1 d . . . H25 H -0.4257 0.2559 0.7504 0.05 Uiso 1 1 calc R . . C8 C 0.7639(3) 0.1495(2) 0.59990(16) 0.0328(5) Uani 1 1 d . . . C3 C 0.2273(3) 0.4106(3) 0.3796(2) 0.0509(8) Uani 1 1 d . . . H3 H 0.1774 0.4696 0.3468 0.061 Uiso 1 1 calc R . . C33 C -0.4196(3) -0.5095(3) 1.19444(19) 0.0487(7) Uani 1 1 d . . . H33 H -0.3763 -0.5454 1.2396 0.058 Uiso 1 1 calc R . . C34 C -0.3673(3) -0.3997(3) 1.14174(17) 0.0418(7) Uani 1 1 d . . . H34 H -0.2865 -0.3623 1.1511 0.05 Uiso 1 1 calc R . . Cu2 Cu -0.36842(3) -0.18417(3) 0.993340(18) 0.03007(9) Uani 1 1 d . . . Cu1 Cu 0.50297(3) 0.12926(3) 0.545052(19) 0.03217(9) Uani 1 1 d . . . O11 O 0.6308(4) 0.7186(3) 0.3306(3) 0.1056(12) Uani 1 1 d D . . O12 O 0.9022(3) 0.6111(2) 0.41493(15) 0.0620(6) Uani 1 1 d D . . O13 O 1.0623(4) 0.0738(5) 0.8287(2) 0.1376(17) Uani 1 1 d D . . H111 H 0.708(4) 0.755(6) 0.307(4) 0.165 Uiso 1 1 d D . . H112 H 0.652(7) 0.654(3) 0.360(3) 0.165 Uiso 1 1 d D . . H121 H 0.971(5) 0.614(6) 0.440(3) 0.165 Uiso 1 1 d D . . H122 H 0.844(5) 0.551(4) 0.439(3) 0.165 Uiso 1 1 d D . . H131 H 1.134(3) 0.0345 0.816(3) 0.165 Uiso 1 1 d D . . H132 H 1.073(6) 0.084(6) 0.874(2) 0.165 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O8 0.0206(8) 0.0459(10) 0.0398(10) -0.0207(8) -0.0117(7) 0.0008(7) O6 0.0258(9) 0.0490(11) 0.0456(11) -0.0190(9) -0.0153(8) -0.0046(8) N8 0.0208(10) 0.0456(13) 0.0335(11) -0.0126(10) -0.0063(8) 0.0023(9) O2 0.0324(10) 0.0395(11) 0.0842(16) -0.0113(10) -0.0236(10) -0.0110(8) O3 0.0323(9) 0.0393(10) 0.0386(10) -0.0031(8) 0.0020(8) -0.0167(8) O7 0.0255(9) 0.0505(11) 0.0361(10) -0.0232(8) -0.0092(7) -0.0018(7) N5 0.0168(9) 0.0348(11) 0.0272(10) -0.0080(8) -0.0055(7) -0.0063(8) O1 0.0375(10) 0.0313(10) 0.0664(14) 0.0004(9) -0.0098(9) -0.0104(8) O9 0.0442(11) 0.0520(12) 0.0499(12) -0.0006(9) -0.0274(9) -0.0150(9) O10 0.0266(9) 0.0436(11) 0.0476(11) -0.0050(9) -0.0128(8) -0.0084(8) O4 0.0755(15) 0.0486(12) 0.0494(13) -0.0217(10) 0.0013(11) -0.0215(11) N4 0.0326(11) 0.0313(11) 0.0255(10) -0.0061(8) -0.0042(8) -0.0104(8) O5 0.0492(11) 0.0536(12) 0.0323(10) -0.0051(9) -0.0091(9) -0.0248(9) N7 0.0220(10) 0.0362(11) 0.0322(11) -0.0092(9) -0.0068(8) -0.0039(8) C20 0.0300(13) 0.0376(14) 0.0314(13) -0.0111(11) -0.0053(10) -0.0029(10) C16 0.0163(10) 0.0299(12) 0.0285(12) -0.0063(10) -0.0059(9) -0.0023(9) N3 0.0305(11) 0.0351(12) 0.0313(11) -0.0089(9) -0.0073(9) -0.0011(9) C23 0.0288(13) 0.0402(15) 0.0472(16) -0.0210(13) -0.0093(11) -0.0038(11) N6 0.0227(10) 0.0378(12) 0.0357(11) -0.0163(9) -0.0061(8) -0.0021(8) C10 0.0465(17) 0.061(2) 0.0533(19) -0.0234(16) -0.0265(14) 0.0196(15) N1 0.0243(10) 0.0370(12) 0.0345(11) -0.0118(9) -0.0068(8) -0.0042(8) C13 0.0300(13) 0.0314(13) 0.0317(13) -0.0013(11) -0.0099(11) -0.0076(10) C31 0.0276(13) 0.0429(15) 0.0406(15) -0.0085(12) -0.0040(11) 0.0015(11) N2 0.0221(10) 0.0291(11) 0.0451(13) -0.0062(9) -0.0102(9) -0.0039(8) C18 0.0340(13) 0.0267(13) 0.0451(16) -0.0008(11) -0.0140(12) -0.0065(10) C24 0.0396(15) 0.0355(15) 0.0574(18) -0.0175(14) -0.0062(13) -0.0093(12) C27 0.0219(11) 0.0375(14) 0.0299(13) -0.0141(11) -0.0043(9) 0.0008(10) C19 0.0350(14) 0.0332(14) 0.0489(17) -0.0171(12) -0.0154(12) 0.0006(11) C6 0.0264(12) 0.0290(13) 0.0375(14) -0.0096(11) -0.0030(10) -0.0026(10) C29 0.0184(11) 0.0367(14) 0.0339(13) -0.0111(11) -0.0031(9) 0.0002(9) C26 0.0322(13) 0.0391(15) 0.0390(15) -0.0122(12) -0.0089(11) 0.0007(11) C30 0.0217(11) 0.0375(14) 0.0345(14) -0.0125(11) -0.0011(10) 0.0024(10) C15 0.0182(10) 0.0274(12) 0.0303(12) -0.0044(10) -0.0054(9) -0.0033(9) C14 0.0228(11) 0.0362(13) 0.0298(13) -0.0079(11) -0.0005(10) -0.0074(10) C28 0.0219(11) 0.0408(14) 0.0317(13) -0.0100(11) -0.0067(10) -0.0039(10) C17 0.0255(12) 0.0375(14) 0.0294(13) -0.0005(11) -0.0060(10) -0.0076(10) C12 0.0455(16) 0.0377(15) 0.0344(15) -0.0071(12) -0.0075(12) -0.0001(12) C22 0.0260(12) 0.0288(12) 0.0267(12) -0.0063(10) -0.0088(9) -0.0042(9) C11 0.0574(18) 0.0460(17) 0.0402(16) -0.0102(13) -0.0176(14) 0.0133(14) C4 0.0421(15) 0.0423(16) 0.0453(17) -0.0087(13) -0.0131(13) 0.0032(12) C21 0.0219(11) 0.0281(12) 0.0245(12) -0.0027(9) -0.0060(9) -0.0047(9) C7 0.0251(12) 0.0329(14) 0.0461(15) -0.0145(12) -0.0083(11) -0.0029(10) C32 0.0446(16) 0.0456(17) 0.0470(17) -0.0002(14) -0.0052(13) 0.0030(13) C9 0.0328(14) 0.0526(18) 0.0551(18) -0.0228(15) -0.0179(13) 0.0063(12) C5 0.0258(12) 0.0317(13) 0.0337(13) -0.0098(11) -0.0047(10) -0.0005(10) C1 0.0263(12) 0.0497(16) 0.0442(16) -0.0157(13) -0.0076(11) -0.0081(11) C2 0.0288(14) 0.067(2) 0.0569(19) -0.0269(16) -0.0178(13) 0.0030(13) C25 0.0410(15) 0.0359(15) 0.0494(17) -0.0134(13) -0.0066(13) 0.0018(12) C8 0.0263(12) 0.0393(14) 0.0371(14) -0.0174(11) -0.0059(10) -0.0001(10) C3 0.0436(16) 0.061(2) 0.0553(19) -0.0174(16) -0.0250(14) 0.0156(14) C33 0.0394(16) 0.061(2) 0.0435(17) -0.0045(15) -0.0148(13) 0.0124(14) C34 0.0279(13) 0.0605(18) 0.0394(15) -0.0134(14) -0.0125(11) 0.0050(12) Cu2 0.02057(15) 0.04022(18) 0.03341(17) -0.01380(13) -0.00891(12) -0.00209(12) Cu1 0.02674(16) 0.03147(17) 0.03589(18) -0.00153(13) -0.00914(13) -0.01085(12) O11 0.098(2) 0.068(2) 0.135(3) 0.0309(18) -0.066(2) -0.0103(17) O12 0.0606(15) 0.0698(16) 0.0558(14) -0.0114(12) -0.0163(11) -0.0230(12) O13 0.096(2) 0.260(5) 0.113(3) -0.134(3) -0.046(2) 0.054(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O8 C21 1.232(3) . ? O8 Cu2 2.2386(17) . ? O6 C22 1.210(3) . ? N8 C34 1.328(3) . ? N8 C30 1.350(3) . ? N8 Cu2 2.007(2) . ? O2 C7 1.212(3) . ? O3 C13 1.271(3) . ? O3 Cu1 1.9271(16) . ? O7 C22 1.272(3) . ? O7 Cu2 1.9300(16) . ? N5 C21 1.318(3) . ? N5 C16 1.426(3) . ? N5 H5 0.86 . ? O1 C6 1.209(3) . ? O9 C28 1.215(3) . ? O10 C29 1.210(3) . ? O4 C13 1.209(3) . ? N4 C14 1.345(3) . ? N4 C15 1.410(3) . ? N4 H4 0.86 . ? O5 C14 1.208(3) . ? N7 C28 1.356(3) . ? N7 C29 1.362(3) . ? N7 Cu2 1.9253(18) . ? C20 C19 1.374(4) . ? C20 C15 1.387(3) . ? C20 H20 0.93 . ? C16 C17 1.376(3) . ? C16 C15 1.395(3) . ? N3 C12 1.328(3) . ? N3 C8 1.351(3) . ? N3 Cu1 1.996(2) . ? C23 N6 1.334(3) . ? C23 C24 1.373(4) . ? C23 H23 0.93 . ? N6 C27 1.350(3) . ? N6 Cu2 1.990(2) . ? C10 C11 1.369(4) . ? C10 C9 1.374(4) . ? C10 H10 0.93 . ? N1 C1 1.337(3) . ? N1 C5 1.340(3) . ? N1 Cu1 1.994(2) . ? C13 C14 1.529(3) . ? C31 C30 1.367(4) . ? C31 C32 1.375(4) . ? C31 H31 0.93 . ? N2 C6 1.351(3) . ? N2 C7 1.365(3) . ? N2 Cu1 1.9053(19) . ? C18 C19 1.374(4) . ? C18 C17 1.375(4) . ? C18 H18 0.93 . ? C24 C25 1.370(4) . ? C24 H24 0.93 . ? C27 C26 1.360(4) . ? C27 C28 1.504(3) . ? C19 H19 0.93 . ? C6 C5 1.505(3) . ? C29 C30 1.503(3) . ? C26 C25 1.381(4) . ? C26 H26 0.93 . ? C17 H17 0.93 . ? C12 C11 1.380(4) . ? C12 H12 0.93 . ? C22 C21 1.545(3) . ? C11 H11 0.93 . ? C4 C5 1.364(4) . ? C4 C3 1.381(4) . ? C4 H4A 0.93 . ? C7 C8 1.495(4) . ? C32 C33 1.376(4) . ? C32 H32 0.93 . ? C9 C8 1.373(4) . ? C9 H9 0.93 . ? C1 C2 1.370(4) . ? C1 H1 0.93 . ? C2 C3 1.371(4) . ? C2 H2 0.93 . ? C25 H25 0.93 . ? C3 H3 0.93 . ? C33 C34 1.365(4) . ? C33 H33 0.93 . ? C34 H34 0.93 . ? O11 H111 0.83(2) . ? O11 H112 0.81(2) . ? O12 H121 0.85(2) . ? O12 H122 0.85(2) . ? O13 H131 0.829(14) . ? O13 H132 0.829(14) . ? 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 C21 O8 Cu2 106.46(15) . . ? C34 N8 C30 118.6(2) . . ? C34 N8 Cu2 128.58(18) . . ? C30 N8 Cu2 112.83(16) . . ? C13 O3 Cu1 115.31(16) . . ? C22 O7 Cu2 118.73(14) . . ? C21 N5 C16 120.88(18) . . ? C21 N5 H5 119.6 . . ? C16 N5 H5 119.6 . . ? C14 N4 C15 126.1(2) . . ? C14 N4 H4 117 . . ? C15 N4 H4 117 . . ? C28 N7 C29 124.8(2) . . ? C28 N7 Cu2 117.31(15) . . ? C29 N7 Cu2 117.69(16) . . ? C19 C20 C15 120.3(2) . . ? C19 C20 H20 119.9 . . ? C15 C20 H20 119.9 . . ? C17 C16 C15 120.2(2) . . ? C17 C16 N5 118.6(2) . . ? C15 C16 N5 121.2(2) . . ? C12 N3 C8 118.7(2) . . ? C12 N3 Cu1 128.63(18) . . ? C8 N3 Cu1 112.61(17) . . ? N6 C23 C24 121.5(2) . . ? N6 C23 H23 119.3 . . ? C24 C23 H23 119.3 . . ? C23 N6 C27 118.6(2) . . ? C23 N6 Cu2 128.08(17) . . ? C27 N6 Cu2 113.03(16) . . ? C11 C10 C9 119.4(3) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C1 N1 C5 118.3(2) . . ? C1 N1 Cu1 129.01(18) . . ? C5 N1 Cu1 112.59(15) . . ? O4 C13 O3 126.1(2) . . ? O4 C13 C14 119.2(2) . . ? O3 C13 C14 114.7(2) . . ? C30 C31 C32 118.5(3) . . ? C30 C31 H31 120.8 . . ? C32 C31 H31 120.8 . . ? C6 N2 C7 124.5(2) . . ? C6 N2 Cu1 117.77(15) . . ? C7 N2 Cu1 117.75(17) . . ? C19 C18 C17 119.5(2) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C25 C24 C23 119.9(2) . . ? C25 C24 H24 120 . . ? C23 C24 H24 120 . . ? N6 C27 C26 122.3(2) . . ? N6 C27 C28 115.5(2) . . ? C26 C27 C28 122.2(2) . . ? C20 C19 C18 120.7(2) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? O1 C6 N2 128.2(2) . . ? O1 C6 C5 120.6(2) . . ? N2 C6 C5 111.2(2) . . ? O10 C29 N7 128.1(2) . . ? O10 C29 C30 120.8(2) . . ? N7 C29 C30 111.03(19) . . ? C27 C26 C25 119.0(2) . . ? C27 C26 H26 120.5 . . ? C25 C26 H26 120.5 . . ? N8 C30 C31 122.2(2) . . ? N8 C30 C29 115.8(2) . . ? C31 C30 C29 122.0(2) . . ? C20 C15 C16 118.7(2) . . ? C20 C15 N4 122.0(2) . . ? C16 C15 N4 119.1(2) . . ? O5 C14 N4 126.1(2) . . ? O5 C14 C13 120.7(2) . . ? N4 C14 C13 113.2(2) . . ? O9 C28 N7 128.2(2) . . ? O9 C28 C27 120.7(2) . . ? N7 C28 C27 111.10(19) . . ? C18 C17 C16 120.6(2) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? N3 C12 C11 122.3(3) . . ? N3 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? O6 C22 O7 126.8(2) . . ? O6 C22 C21 119.1(2) . . ? O7 C22 C21 114.07(18) . . ? C10 C11 C12 118.8(3) . . ? C10 C11 H11 120.6 . . ? C12 C11 H11 120.6 . . ? C5 C4 C3 118.8(3) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? O8 C21 N5 124.2(2) . . ? O8 C21 C22 120.5(2) . . ? N5 C21 C22 115.20(19) . . ? O2 C7 N2 127.5(2) . . ? O2 C7 C8 121.3(2) . . ? N2 C7 C8 111.1(2) . . ? C31 C32 C33 119.4(3) . . ? C31 C32 H32 120.3 . . ? C33 C32 H32 120.3 . . ? C8 C9 C10 119.2(3) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? N1 C5 C4 122.5(2) . . ? N1 C5 C6 115.8(2) . . ? C4 C5 C6 121.8(2) . . ? N1 C1 C2 122.3(3) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 118.9(3) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C24 C25 C26 118.6(3) . . ? C24 C25 H25 120.7 . . ? C26 C25 H25 120.7 . . ? N3 C8 C9 121.5(3) . . ? N3 C8 C7 115.8(2) . . ? C9 C8 C7 122.6(2) . . ? C2 C3 C4 119.1(3) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C34 C33 C32 119.0(3) . . ? C34 C33 H33 120.5 . . ? C32 C33 H33 120.5 . . ? N8 C34 C33 122.3(3) . . ? N8 C34 H34 118.9 . . ? C33 C34 H34 118.9 . . ? N7 Cu2 O7 177.46(8) . . ? N7 Cu2 N6 82.26(8) . . ? O7 Cu2 N6 97.07(8) . . ? N7 Cu2 N8 82.01(8) . . ? O7 Cu2 N8 98.17(8) . . ? N6 Cu2 N8 160.99(8) . . ? N7 Cu2 O8 102.41(7) . . ? O7 Cu2 O8 80.09(6) . . ? N6 Cu2 O8 95.79(7) . . ? N8 Cu2 O8 97.96(7) . . ? N2 Cu1 O3 176.44(9) . . ? N2 Cu1 N1 82.66(8) . . ? O3 Cu1 N1 97.06(8) . . ? N2 Cu1 N3 82.58(8) . . ? O3 Cu1 N3 97.95(8) . . ? N1 Cu1 N3 164.61(8) . . ? H111 O11 H112 106(6) . . ? H121 O12 H122 113(6) . . ? H131 O13 H132 104(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5 O9 0.86 2.28 3.025(2) 144.3 1_655 N5 H5 O10 0.86 2.26 2.876(2) 128.6 1_655 N4 H4 O9 0.86 2.15 2.989(3) 164.6 1_655 O11 H111 O4 0.83(2) 2.45(6) 2.900(4) 115(5) 2_666 O12 H121 O2 0.85(2) 2.02(2) 2.855(3) 166(6) 2_766 O12 H122 O1 0.85(2) 2.17(4) 2.874(3) 140(6) . O13 H132 O6 0.829(14) 2.34(3) 3.046(4) 143(5) 2_657 O13 H131 O4 0.829(14) 2.45(4) 3.046(4) 130(4) 1_655 O13 H132 O7 0.829(14) 2.39(3) 3.159(3) 155(6) 2_657 data_cuopcubp_1 _database_code_depnum_ccdc_archive 'CCDC 909392' #TrackingRef '15204_web_deposit_cif_file_4_MariadelDeniz_1352130728.(5).cif' _audit_creation_date 2012-10-23T13:43:29-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H19 Cu N5 O8' _chemical_formula_sum 'C24 H19 Cu N5 O8' _chemical_formula_weight 568.98 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.2927(3) _cell_length_b 9.66890(10) _cell_length_c 18.7558(4) _cell_angle_alpha 90 _cell_angle_beta 107.619(2) _cell_angle_gamma 90 _cell_volume 2297.52(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 12805 _cell_measurement_theta_min 3.0633 _cell_measurement_theta_max 29.4854 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prismatic _exptl_crystal_colour blue _exptl_crystal_size_max 0.5649 _exptl_crystal_size_mid 0.2629 _exptl_crystal_size_min 0.0585 _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1164 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.014 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.685 _exptl_absorpt_correction_T_max 0.942 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120.0 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.4186 _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_unetI/netI 0.0213 _diffrn_reflns_number 26663 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 5254 _reflns_number_gt 4722 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^)+(0.0317P)^2^+1.7386P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5254 _refine_ls_number_parameters 350 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0313 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0708 _refine_ls_wR_factor_gt 0.068 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.432 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.056 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 0.922358(14) 0.418128(18) 0.684186(10) 0.01183(6) Uani 1 1 d . . . O7 O 0.88324(10) 0.05809(12) 0.56985(7) 0.0227(3) Uani 1 1 d . . . O1 O 0.58590(10) 0.43820(14) 0.69677(8) 0.0290(3) Uani 1 1 d . . . O3 O 0.38223(10) 0.61132(14) 0.56456(8) 0.0286(3) Uani 1 1 d . . . O5 O 0.96801(8) 0.60737(11) 0.71480(6) 0.0146(2) Uani 1 1 d . . . O8 O 0.75853(9) 0.06384(11) 0.67393(7) 0.0189(2) Uani 1 1 d . . . N1 N 0.56078(10) 0.61841(14) 0.58192(8) 0.0169(3) Uani 1 1 d D . . O4 O 0.77438(8) 0.56445(11) 0.61254(6) 0.0150(2) Uani 1 1 d . . . N2 N 0.74376(10) 0.79743(13) 0.61105(7) 0.0129(3) Uani 1 1 d D . . N5 N 0.99962(10) 0.39066(13) 0.60894(7) 0.0137(3) Uani 1 1 d . . . O6 O 1.07940(8) 0.32699(11) 0.77500(6) 0.0174(2) Uani 1 1 d . . . C8 C 0.57201(14) 0.94188(18) 0.43411(10) 0.0217(3) Uani 1 1 d . . . H8 H 0.574 1.0165 0.4016 0.026 Uiso 1 1 calc R . . C19 C 1.03714(14) 0.21903(18) 0.52897(9) 0.0205(3) Uani 1 1 d . . . H19 H 1.0218 0.1319 0.5047 0.025 Uiso 1 1 calc R . . C12 C 0.80668(15) 0.42093(18) 0.87389(10) 0.0243(4) Uani 1 1 d . . . H12 H 0.8115 0.4774 0.9163 0.029 Uiso 1 1 calc R . . N4 N 0.86337(10) 0.23838(13) 0.64772(7) 0.0134(3) Uani 1 1 d . . . C18 C 0.98126(12) 0.26544(16) 0.57571(8) 0.0152(3) Uani 1 1 d . . . N3 N 0.84942(10) 0.38382(13) 0.76105(7) 0.0137(3) Uani 1 1 d . . . C9 C 0.65610(13) 0.91900(16) 0.49801(9) 0.0170(3) Uani 1 1 d . . . H9 H 0.7158 0.9784 0.5091 0.02 Uiso 1 1 calc R . . C21 C 1.13557(14) 0.43087(19) 0.55252(10) 0.0230(4) Uani 1 1 d . . . H21 H 1.1895 0.4893 0.5458 0.028 Uiso 1 1 calc R . . C20 C 1.11624(14) 0.30294(19) 0.51831(10) 0.0241(4) Uani 1 1 d . . . H20 H 1.157 0.2724 0.4875 0.029 Uiso 1 1 calc R . . C13 C 0.75273(14) 0.29668(19) 0.86428(10) 0.0242(4) Uani 1 1 d . . . H13 H 0.7193 0.267 0.8998 0.029 Uiso 1 1 calc R . . C7 C 0.48508(13) 0.85503(19) 0.41799(9) 0.0217(3) Uani 1 1 d . . . H7 H 0.4277 0.8695 0.3739 0.026 Uiso 1 1 calc R . . C4 C 0.79967(11) 0.68279(15) 0.63594(8) 0.0118(3) Uani 1 1 d . . . C2 C 0.47221(13) 0.57426(16) 0.59566(10) 0.0186(3) Uani 1 1 d . . . C14 C 0.74794(13) 0.21569(17) 0.80220(10) 0.0195(3) Uani 1 1 d . . . H14 H 0.7108 0.1303 0.7944 0.023 Uiso 1 1 calc R . . C5 C 0.56535(12) 0.72391(15) 0.53049(9) 0.0150(3) Uani 1 1 d . . . C17 C 0.90154(12) 0.17453(16) 0.59657(9) 0.0151(3) Uani 1 1 d . . . C10 C 0.65414(11) 0.81026(15) 0.54593(8) 0.0130(3) Uani 1 1 d . . . C22 C 1.07420(13) 0.47205(18) 0.59699(9) 0.0185(3) Uani 1 1 d . . . H22 H 1.0856 0.5609 0.6196 0.022 Uiso 1 1 calc R . . C1 C 0.49790(13) 0.46916(17) 0.66070(10) 0.0205(3) Uani 1 1 d . . . C11 C 0.85351(13) 0.46151(17) 0.82061(9) 0.0191(3) Uani 1 1 d . . . H11 H 0.8897 0.5475 0.8267 0.023 Uiso 1 1 calc R . . C6 C 0.48133(12) 0.74729(17) 0.46574(9) 0.0191(3) Uani 1 1 d . . . H6 H 0.4211 0.6888 0.4544 0.023 Uiso 1 1 calc R . . C15 C 0.79824(11) 0.26162(15) 0.75194(9) 0.0140(3) Uani 1 1 d . . . C16 C 0.80391(11) 0.17540(15) 0.68609(9) 0.0139(3) Uani 1 1 d . . . C3 C 0.90562(11) 0.71024(15) 0.69815(8) 0.0118(3) Uani 1 1 d . . . O2 O 0.40957(10) 0.42225(13) 0.67049(8) 0.0268(3) Uani 1 1 d . . . C23 C 0.42195(16) 0.3182(2) 0.72973(11) 0.0320(4) Uani 1 1 d . . . H23A H 0.4455 0.3625 0.7796 0.038 Uiso 1 1 calc R . . H23B H 0.4748 0.2479 0.727 0.038 Uiso 1 1 calc R . . C24 C 0.31650(16) 0.2532(2) 0.71686(12) 0.0331(4) Uani 1 1 d . . . H24A H 0.2664 0.3225 0.7236 0.05 Uiso 1 1 calc R . . H24B H 0.322 0.1776 0.7527 0.05 Uiso 1 1 calc R . . H24C H 0.2917 0.2165 0.6658 0.05 Uiso 1 1 calc R . . H2 H 0.7735(17) 0.8756(16) 0.6323(12) 0.04 Uiso 1 1 d D . . H1 H 0.6201(12) 0.575(2) 0.6054(12) 0.04 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01236(10) 0.00900(10) 0.01424(10) -0.00202(6) 0.00421(7) -0.00202(6) O7 0.0238(6) 0.0167(6) 0.0275(7) -0.0097(5) 0.0080(5) -0.0033(5) O1 0.0202(6) 0.0339(7) 0.0293(7) 0.0075(6) 0.0019(5) -0.0041(5) O3 0.0162(6) 0.0310(7) 0.0407(8) 0.0092(6) 0.0117(6) 0.0059(5) O5 0.0120(5) 0.0109(5) 0.0185(5) -0.0011(4) 0.0007(4) -0.0002(4) O8 0.0155(6) 0.0117(5) 0.0290(6) -0.0021(4) 0.0060(5) -0.0026(4) N1 0.0125(6) 0.0146(6) 0.0223(7) 0.0006(5) 0.0030(5) -0.0010(5) O4 0.0126(5) 0.0114(5) 0.0190(6) -0.0030(4) 0.0018(4) -0.0006(4) N2 0.0118(6) 0.0103(6) 0.0149(6) -0.0027(5) 0.0013(5) -0.0009(5) N5 0.0121(6) 0.0148(6) 0.0130(6) 0.0009(5) 0.0019(5) 0.0002(5) O6 0.0147(5) 0.0125(5) 0.0211(6) 0.0039(4) -0.0004(4) 0.0002(4) C8 0.0210(8) 0.0222(8) 0.0206(8) 0.0056(6) 0.0043(7) 0.0036(6) C19 0.0249(8) 0.0205(8) 0.0159(8) -0.0004(6) 0.0061(7) 0.0058(7) C12 0.0275(9) 0.0274(9) 0.0208(8) -0.0041(7) 0.0117(7) 0.0013(7) N4 0.0124(6) 0.0105(6) 0.0154(6) -0.0010(5) 0.0016(5) -0.0002(5) C18 0.0143(7) 0.0164(7) 0.0127(7) 0.0007(6) 0.0011(6) 0.0020(6) N3 0.0117(6) 0.0128(6) 0.0159(6) -0.0005(5) 0.0032(5) 0.0012(5) C9 0.0147(7) 0.0159(7) 0.0198(8) 0.0002(6) 0.0044(6) -0.0006(6) C21 0.0192(8) 0.0286(9) 0.0231(9) 0.0088(7) 0.0092(7) 0.0008(7) C20 0.0253(9) 0.0310(9) 0.0195(8) 0.0061(7) 0.0116(7) 0.0090(7) C13 0.0237(9) 0.0281(9) 0.0255(9) 0.0058(7) 0.0143(7) 0.0032(7) C7 0.0151(8) 0.0277(9) 0.0185(8) 0.0004(7) -0.0007(6) 0.0039(7) C4 0.0112(7) 0.0130(7) 0.0119(7) -0.0007(5) 0.0047(6) -0.0007(5) C2 0.0168(8) 0.0146(7) 0.0254(9) -0.0030(6) 0.0080(7) 0.0000(6) C14 0.0154(7) 0.0167(7) 0.0271(9) 0.0049(6) 0.0072(7) 0.0009(6) C5 0.0141(7) 0.0119(7) 0.0192(8) -0.0027(6) 0.0052(6) 0.0007(6) C17 0.0135(7) 0.0141(7) 0.0150(7) -0.0014(6) 0.0002(6) 0.0009(6) C10 0.0111(7) 0.0119(7) 0.0146(7) -0.0030(5) 0.0018(6) 0.0027(5) C22 0.0171(8) 0.0193(8) 0.0177(8) 0.0026(6) 0.0032(6) -0.0008(6) C1 0.0213(8) 0.0180(8) 0.0239(8) -0.0028(7) 0.0091(7) -0.0028(6) C11 0.0202(8) 0.0175(8) 0.0200(8) -0.0038(6) 0.0065(7) -0.0013(6) C6 0.0133(7) 0.0207(8) 0.0213(8) -0.0045(6) 0.0025(6) -0.0010(6) C15 0.0098(7) 0.0114(7) 0.0191(8) 0.0017(6) 0.0021(6) 0.0027(5) C16 0.0094(7) 0.0121(7) 0.0178(7) 0.0017(6) 0.0005(6) 0.0026(5) C3 0.0097(7) 0.0128(7) 0.0129(7) -0.0001(5) 0.0036(6) -0.0015(5) O2 0.0207(6) 0.0277(7) 0.0339(7) 0.0099(5) 0.0111(6) -0.0013(5) C23 0.0297(10) 0.0343(10) 0.0304(10) 0.0119(8) 0.0066(8) -0.0015(8) C24 0.0324(10) 0.0361(11) 0.0335(10) 0.0124(9) 0.0138(9) -0.0036(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.9438(13) . ? Cu1 O5 1.9583(11) . ? Cu1 N3 1.9937(13) . ? Cu1 N5 1.9987(13) . ? Cu1 O6 2.4255(11) . ? O7 C17 1.2264(19) . ? O1 C1 1.198(2) . ? O3 C2 1.215(2) . ? O5 C3 1.2720(18) . ? O8 C16 1.2231(19) . ? N1 C2 1.349(2) . ? N1 C5 1.418(2) . ? N1 H1 0.885(10) . ? O4 C4 1.2351(18) . ? N2 C4 1.3375(19) . ? N2 C10 1.4302(19) . ? N2 H2 0.890(10) . ? N5 C22 1.337(2) . ? N5 C18 1.350(2) . ? O6 C3 1.2275(18) 2_746 ? C8 C7 1.386(2) . ? C8 C9 1.387(2) . ? C8 H8 0.95 . ? C19 C18 1.384(2) . ? C19 C20 1.390(3) . ? C19 H19 0.95 . ? C12 C13 1.383(3) . ? C12 C11 1.384(2) . ? C12 H12 0.95 . ? N4 C17 1.361(2) . ? N4 C16 1.363(2) . ? C18 C17 1.517(2) . ? N3 C11 1.334(2) . ? N3 C15 1.348(2) . ? C9 C10 1.388(2) . ? C9 H9 0.95 . ? C21 C20 1.381(3) . ? C21 C22 1.390(2) . ? C21 H21 0.95 . ? C20 H20 0.95 . ? C13 C14 1.389(2) . ? C13 H13 0.95 . ? C7 C6 1.384(2) . ? C7 H7 0.95 . ? C4 C3 1.556(2) . ? C2 C1 1.544(2) . ? C14 C15 1.384(2) . ? C14 H14 0.95 . ? C5 C6 1.397(2) . ? C5 C10 1.402(2) . ? C22 H22 0.95 . ? C1 O2 1.322(2) . ? C11 H11 0.95 . ? C6 H6 0.95 . ? C15 C16 1.511(2) . ? C3 O6 1.2276(18) 2_756 ? O2 C23 1.470(2) . ? C23 C24 1.488(3) . ? C23 H23A 0.99 . ? C23 H23B 0.99 . ? C24 H24A 0.98 . ? C24 H24B 0.98 . ? C24 H24C 0.98 . ? 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 O5 174.13(5) . . ? N4 Cu1 N3 82.71(5) . . ? O5 Cu1 N3 96.82(5) . . ? N4 Cu1 N5 82.61(5) . . ? O5 Cu1 N5 98.71(5) . . ? N3 Cu1 N5 162.71(5) . . ? N4 Cu1 O6 95.28(5) . . ? O5 Cu1 O6 90.52(4) . . ? N3 Cu1 O6 86.29(5) . . ? N5 Cu1 O6 86.02(5) . . ? C3 O5 Cu1 122.52(9) . . ? C2 N1 C5 125.27(14) . . ? C2 N1 H1 116.9(16) . . ? C5 N1 H1 117.7(16) . . ? C4 N2 C10 126.96(13) . . ? C4 N2 H2 115.0(16) . . ? C10 N2 H2 116.8(15) . . ? C22 N5 C18 119.36(14) . . ? C22 N5 Cu1 127.29(11) . . ? C18 N5 Cu1 112.68(10) . . ? C3 O6 Cu1 128.35(10) 2_746 . ? C7 C8 C9 119.51(16) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C18 C19 C20 118.44(16) . . ? C18 C19 H19 120.8 . . ? C20 C19 H19 120.8 . . ? C13 C12 C11 118.74(16) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C17 N4 C16 124.66(13) . . ? C17 N4 Cu1 117.18(10) . . ? C16 N4 Cu1 116.76(10) . . ? N5 C18 C19 121.78(15) . . ? N5 C18 C17 116.33(13) . . ? C19 C18 C17 121.76(14) . . ? C11 N3 C15 119.40(14) . . ? C11 N3 Cu1 127.34(11) . . ? C15 N3 Cu1 113.04(10) . . ? C8 C9 C10 120.80(15) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C20 C21 C22 118.35(16) . . ? C20 C21 H21 120.8 . . ? C22 C21 H21 120.8 . . ? C21 C20 C19 119.90(16) . . ? C21 C20 H20 120 . . ? C19 C20 H20 120 . . ? C12 C13 C14 119.32(16) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C6 C7 C8 120.38(15) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? O4 C4 N2 125.52(14) . . ? O4 C4 C3 120.78(13) . . ? N2 C4 C3 113.68(12) . . ? O3 C2 N1 127.18(16) . . ? O3 C2 C1 121.56(15) . . ? N1 C2 C1 111.23(14) . . ? C15 C14 C13 118.77(15) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C6 C5 C10 118.97(15) . . ? C6 C5 N1 121.34(14) . . ? C10 C5 N1 119.64(14) . . ? O7 C17 N4 129.36(15) . . ? O7 C17 C18 119.63(14) . . ? N4 C17 C18 110.94(13) . . ? C9 C10 C5 119.78(14) . . ? C9 C10 N2 116.39(13) . . ? C5 C10 N2 123.78(14) . . ? N5 C22 C21 122.12(16) . . ? N5 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? O1 C1 O2 126.29(16) . . ? O1 C1 C2 123.71(15) . . ? O2 C1 C2 110.00(14) . . ? N3 C11 C12 122.13(16) . . ? N3 C11 H11 118.9 . . ? C12 C11 H11 118.9 . . ? C7 C6 C5 120.54(15) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? N3 C15 C14 121.62(15) . . ? N3 C15 C16 116.05(13) . . ? C14 C15 C16 122.26(14) . . ? O8 C16 N4 128.87(15) . . ? O8 C16 C15 119.69(14) . . ? N4 C16 C15 111.44(13) . . ? O6 C3 O5 127.27(14) 2_756 . ? O6 C3 C4 117.53(13) 2_756 . ? O5 C3 C4 115.19(13) . . ? C1 O2 C23 116.01(14) . . ? O2 C23 C24 106.38(15) . . ? O2 C23 H23A 110.5 . . ? C24 C23 H23A 110.5 . . ? O2 C23 H23B 110.5 . . ? C24 C23 H23B 110.5 . . ? H23A C23 H23B 108.6 . . ? 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 . . ? # END of CIF