# Electronic Supplementary Material (ESI) for Chemical Communications # 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 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H6 Cu N2 O12, C12 H16 N4, 4(H2 O)' _chemical_formula_sum 'C28 H30 Cu N6 O16' _chemical_formula_weight 770.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' 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 19.2201(5) _cell_length_b 9.6352(3) _cell_length_c 17.0833(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.751(14) _cell_angle_gamma 90.00 _cell_volume 3029.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4160 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.689 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1588 _exptl_absorpt_coefficient_mu 0.813 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8947 _exptl_absorpt_correction_T_max 0.9087 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7870 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0680 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 30.03 _reflns_number_total 4420 _reflns_number_gt 2927 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0682P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4420 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0887 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1203 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.25839(12) 0.2372(2) 0.33506(14) 0.0208(5) Uani 1 1 d . . . N1 N 0.30569(10) 0.1628(2) 0.31176(11) 0.0264(4) Uani 1 1 d . . . H1 H 0.3368 0.1052 0.3436 0.032 Uiso 1 1 calc R . . C2 C 0.29987(14) 0.1884(3) 0.22519(15) 0.0326(6) Uani 1 1 d . . . H2A H 0.2964 0.1003 0.1945 0.039 Uiso 1 1 calc R . . H2B H 0.3419 0.2424 0.2192 0.039 Uiso 1 1 calc R . . C3 C 0.22942(14) 0.2720(3) 0.19648(15) 0.0314(6) Uani 1 1 d . . . H3A H 0.2359 0.3556 0.1656 0.038 Uiso 1 1 calc R . . H3B H 0.1893 0.2151 0.1619 0.038 Uiso 1 1 calc R . . N2 N 0.21592(10) 0.3092(2) 0.27416(12) 0.0264(4) Uani 1 1 d . . . H2 H 0.1839 0.3711 0.2794 0.032 Uiso 1 1 calc R . . C4 C 0.25376(11) 0.2433(2) 0.41966(14) 0.0210(5) Uani 1 1 d . . . C5 C 0.28800(12) 0.1424(3) 0.47672(14) 0.0255(5) Uani 1 1 d . . . H5 H 0.3139 0.0687 0.4608 0.031 Uiso 1 1 calc R . . C6 C 0.21582(12) 0.3501(3) 0.44355(14) 0.0255(5) Uani 1 1 d . . . H6 H 0.1923 0.4186 0.4050 0.031 Uiso 1 1 calc R . . Cu1 Cu 0.0000 0.24586(4) 0.2500 0.02083(14) Uani 1 2 d S . . N3 N 0.02830(10) 0.22666(18) 0.36770(11) 0.0179(4) Uani 1 1 d . . . C7 C 0.07364(11) 0.1231(2) 0.40209(12) 0.0180(4) Uani 1 1 d . . . C8 C 0.08555(11) 0.0892(2) 0.48380(12) 0.0190(4) Uani 1 1 d . . . H8 H 0.1170 0.0150 0.5078 0.023 Uiso 1 1 calc R . . C9 C 0.05022(11) 0.1666(2) 0.52982(13) 0.0201(5) Uani 1 1 d . . . C10 C 0.00444(12) 0.2751(2) 0.49323(14) 0.0200(5) Uani 1 1 d . . . H10 H -0.0194 0.3295 0.5241 0.024 Uiso 1 1 calc R . . C11 C -0.00566(11) 0.3021(2) 0.41130(13) 0.0186(4) Uani 1 1 d . . . C12 C 0.10717(11) 0.0472(2) 0.34370(13) 0.0201(5) Uani 1 1 d . . . O1 O 0.15068(9) -0.04634(18) 0.36905(9) 0.0304(4) Uani 1 1 d . . . O2 O 0.08633(8) 0.09290(17) 0.27029(8) 0.0246(4) Uani 1 1 d . . . C13 C 0.05772(12) 0.1307(3) 0.61752(13) 0.0233(5) Uani 1 1 d . . . O3 O 0.10353(9) 0.02780(19) 0.64430(9) 0.0287(4) Uani 1 1 d . . . H3 H 0.0999 0.0002 0.6896 0.043 Uiso 1 1 calc R . . O4 O 0.02403(10) 0.1894(2) 0.65728(10) 0.0368(4) Uani 1 1 d . . . C14 C -0.05874(11) 0.4072(2) 0.36103(13) 0.0209(5) Uani 1 1 d . . . O5 O -0.08929(8) 0.48584(18) 0.39787(10) 0.0279(4) Uani 1 1 d . . . O6 O -0.06891(8) 0.40091(17) 0.28423(8) 0.0247(4) Uani 1 1 d . . . O7 O 0.42374(14) 0.0794(3) 0.1354(2) 0.0861(9) Uani 1 1 d . . . O8 O 0.32544(15) 0.2522(3) 0.01461(19) 0.0800(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0194(11) 0.0203(12) 0.0231(11) 0.0007(9) 0.0065(9) -0.0010(9) N1 0.0325(11) 0.0262(11) 0.0220(10) 0.0041(8) 0.0104(8) 0.0075(9) C2 0.0455(15) 0.0298(14) 0.0264(13) 0.0040(11) 0.0166(11) 0.0069(12) C3 0.0367(14) 0.0337(15) 0.0232(12) 0.0017(10) 0.0078(11) 0.0008(11) N2 0.0281(10) 0.0291(11) 0.0227(10) 0.0032(9) 0.0084(8) 0.0061(9) C4 0.0168(10) 0.0249(12) 0.0215(11) 0.0009(9) 0.0061(9) -0.0030(9) C5 0.0245(12) 0.0256(13) 0.0287(12) 0.0018(10) 0.0113(10) 0.0040(10) C6 0.0237(11) 0.0269(13) 0.0255(12) 0.0034(10) 0.0063(9) 0.0034(10) Cu1 0.0244(2) 0.0219(2) 0.0161(2) 0.000 0.00579(16) 0.000 N3 0.0174(9) 0.0202(10) 0.0158(9) -0.0022(7) 0.0044(7) -0.0002(7) C7 0.0194(10) 0.0176(10) 0.0171(10) -0.0004(8) 0.0055(8) -0.0012(9) C8 0.0185(10) 0.0207(11) 0.0162(10) 0.0005(9) 0.0027(8) -0.0012(9) C9 0.0209(10) 0.0238(12) 0.0153(10) -0.0015(9) 0.0046(8) -0.0043(9) C10 0.0198(11) 0.0213(12) 0.0188(10) -0.0039(9) 0.0056(9) -0.0012(9) C11 0.0168(10) 0.0187(11) 0.0202(11) -0.0046(9) 0.0054(9) -0.0018(9) C12 0.0201(11) 0.0204(11) 0.0196(11) -0.0032(9) 0.0056(9) -0.0004(9) O1 0.0344(9) 0.0320(10) 0.0257(9) 0.0005(7) 0.0101(7) 0.0141(8) O2 0.0329(9) 0.0267(9) 0.0151(7) 0.0012(7) 0.0081(7) 0.0030(7) C13 0.0242(11) 0.0255(12) 0.0193(11) -0.0007(9) 0.0051(9) -0.0030(10) O3 0.0362(9) 0.0330(10) 0.0191(8) 0.0082(7) 0.0114(7) 0.0069(8) O4 0.0452(10) 0.0473(12) 0.0227(9) 0.0049(8) 0.0175(8) 0.0148(9) C14 0.0190(10) 0.0218(12) 0.0216(11) -0.0009(9) 0.0055(9) -0.0013(9) O5 0.0292(9) 0.0276(9) 0.0277(9) -0.0022(7) 0.0094(7) 0.0097(7) O6 0.0273(8) 0.0285(9) 0.0162(8) 0.0000(7) 0.0029(6) 0.0013(7) O7 0.0842(17) 0.0509(16) 0.154(3) 0.0233(17) 0.0842(18) 0.0110(14) O8 0.0644(16) 0.092(2) 0.087(2) -0.0480(16) 0.0268(15) -0.0171(14) _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 C1 N1 1.307(3) . ? C1 N2 1.319(3) . ? C1 C4 1.475(3) . ? N1 C2 1.471(3) . ? N1 H1 0.8800 . ? C2 C3 1.530(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N2 1.468(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N2 H2 0.8800 . ? C4 C6 1.389(3) . ? C4 C5 1.400(3) . ? C5 C6 1.387(3) 7_556 ? C5 H5 0.9500 . ? C6 C5 1.387(3) 7_556 ? C6 H6 0.9500 . ? Cu1 N3 1.9346(18) 2 ? Cu1 N3 1.9346(18) . ? Cu1 O2 2.1712(16) 2 ? Cu1 O2 2.1712(16) . ? Cu1 O6 2.1850(16) 2 ? Cu1 O6 2.1850(16) . ? N3 C11 1.338(3) . ? N3 C7 1.344(3) . ? C7 C8 1.387(3) . ? C7 C12 1.521(3) . ? C8 C9 1.394(3) . ? C8 H8 0.9500 . ? C9 C10 1.393(3) . ? C9 C13 1.504(3) . ? C10 C11 1.381(3) . ? C10 H10 0.9500 . ? C11 C14 1.516(3) . ? C12 O1 1.221(3) . ? C12 O2 1.280(3) . ? C13 O4 1.206(3) . ? C13 O3 1.317(3) . ? O3 H3 0.8400 . ? C14 O5 1.236(3) . ? C14 O6 1.271(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 N1 C1 N2 112.0(2) . . ? N1 C1 C4 124.3(2) . . ? N2 C1 C4 123.6(2) . . ? C1 N1 C2 110.87(19) . . ? C1 N1 H1 124.6 . . ? C2 N1 H1 124.6 . . ? N1 C2 C3 102.4(2) . . ? N1 C2 H2A 111.3 . . ? C3 C2 H2A 111.3 . . ? N1 C2 H2B 111.3 . . ? C3 C2 H2B 111.3 . . ? H2A C2 H2B 109.2 . . ? N2 C3 C2 102.1(2) . . ? N2 C3 H3A 111.3 . . ? C2 C3 H3A 111.3 . . ? N2 C3 H3B 111.3 . . ? C2 C3 H3B 111.3 . . ? H3A C3 H3B 109.2 . . ? C1 N2 C3 110.7(2) . . ? C1 N2 H2 124.6 . . ? C3 N2 H2 124.6 . . ? C6 C4 C5 119.4(2) . . ? C6 C4 C1 120.2(2) . . ? C5 C4 C1 120.4(2) . . ? C6 C5 C4 120.0(2) 7_556 . ? C6 C5 H5 120.0 7_556 . ? C4 C5 H5 120.0 . . ? C5 C6 C4 120.5(2) 7_556 . ? C5 C6 H6 119.7 7_556 . ? C4 C6 H6 119.7 . . ? N3 Cu1 N3 169.02(11) 2 . ? N3 Cu1 O2 78.24(7) 2 2 ? N3 Cu1 O2 94.24(6) . 2 ? N3 Cu1 O2 94.24(6) 2 . ? N3 Cu1 O2 78.24(6) . . ? O2 Cu1 O2 94.50(9) 2 . ? N3 Cu1 O6 78.33(6) 2 2 ? N3 Cu1 O6 109.45(7) . 2 ? O2 Cu1 O6 156.30(5) 2 2 ? O2 Cu1 O6 90.72(6) . 2 ? N3 Cu1 O6 109.45(6) 2 . ? N3 Cu1 O6 78.33(6) . . ? O2 Cu1 O6 90.72(6) 2 . ? O2 Cu1 O6 156.30(5) . . ? O6 Cu1 O6 93.73(9) 2 . ? C11 N3 C7 121.28(19) . . ? C11 N3 Cu1 119.38(14) . . ? C7 N3 Cu1 118.56(15) . . ? N3 C7 C8 120.9(2) . . ? N3 C7 C12 114.46(18) . . ? C8 C7 C12 124.64(19) . . ? C7 C8 C9 118.4(2) . . ? C7 C8 H8 120.8 . . ? C9 C8 H8 120.8 . . ? C10 C9 C8 119.73(19) . . ? C10 C9 C13 119.1(2) . . ? C8 C9 C13 121.1(2) . . ? C11 C10 C9 118.8(2) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? N3 C11 C10 120.9(2) . . ? N3 C11 C14 113.85(18) . . ? C10 C11 C14 125.1(2) . . ? O1 C12 O2 126.2(2) . . ? O1 C12 C7 119.89(19) . . ? O2 C12 C7 113.92(19) . . ? C12 O2 Cu1 113.49(14) . . ? O4 C13 O3 124.8(2) . . ? O4 C13 C9 122.7(2) . . ? O3 C13 C9 112.45(19) . . ? C13 O3 H3 109.5 . . ? O5 C14 O6 126.9(2) . . ? O5 C14 C11 117.52(19) . . ? O6 C14 C11 115.53(19) . . ? C14 O6 Cu1 112.59(14) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.694 _refine_diff_density_min -0.632 _refine_diff_density_rms 0.088 _database_code_depnum_ccdc_archive 'CCDC 949324' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H6 N2 Ni O12, C12 H16 N4, 4(H2 O)' _chemical_formula_sum 'C28 H30 N6 Ni O16' _chemical_formula_weight 765.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 '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 _symmetry_space_group_name_Hall '-C 2yc' 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 19.1971(5) _cell_length_b 9.6310(2) _cell_length_c 17.0962(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.581(11) _cell_angle_gamma 90.00 _cell_volume 3029.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4379 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.678 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.733 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9044 _exptl_absorpt_correction_T_max 0.9172 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7659 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0603 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 30.04 _reflns_number_total 4421 _reflns_number_gt 2974 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0752P)^2^+1.3355P] 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 4421 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1405 _refine_ls_wR_factor_gt 0.1218 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.25771(12) 0.2374(2) 0.33493(14) 0.0219(5) Uani 1 1 d . . . N1 N 0.30520(11) 0.1641(2) 0.31136(12) 0.0266(4) Uani 1 1 d . . . H1 H 0.3369 0.1074 0.3431 0.032 Uiso 1 1 calc R . . C2 C 0.29857(15) 0.1889(3) 0.22471(15) 0.0333(6) Uani 1 1 d . . . H2A H 0.2948 0.1005 0.1943 0.040 Uiso 1 1 calc R . . H2B H 0.3405 0.2425 0.2180 0.040 Uiso 1 1 calc R . . C3 C 0.22834(14) 0.2726(3) 0.19636(15) 0.0307(6) Uani 1 1 d . . . H3A H 0.2349 0.3565 0.1658 0.037 Uiso 1 1 calc R . . H3B H 0.1882 0.2159 0.1618 0.037 Uiso 1 1 calc R . . N2 N 0.21478(11) 0.3094(2) 0.27441(12) 0.0267(4) Uani 1 1 d . . . H2 H 0.1826 0.3708 0.2799 0.032 Uiso 1 1 calc R . . C4 C 0.25351(12) 0.2434(2) 0.41968(14) 0.0213(5) Uani 1 1 d . . . C5 C 0.28773(12) 0.1424(2) 0.47610(14) 0.0256(5) Uani 1 1 d . . . H5 H 0.3134 0.0686 0.4598 0.031 Uiso 1 1 calc R . . C6 C 0.21564(13) 0.3504(2) 0.44391(14) 0.0258(5) Uani 1 1 d . . . H6 H 0.1919 0.4189 0.4055 0.031 Uiso 1 1 calc R . . Ni1 Ni 0.0000 0.24755(4) 0.2500 0.01906(13) Uani 1 2 d S . . N3 N 0.02966(10) 0.22818(18) 0.36915(11) 0.0176(4) Uani 1 1 d . . . C7 C 0.07430(11) 0.1237(2) 0.40244(12) 0.0177(4) Uani 1 1 d . . . C8 C 0.08583(11) 0.0886(2) 0.48399(13) 0.0197(4) Uani 1 1 d . . . H8 H 0.1171 0.0140 0.5078 0.024 Uiso 1 1 calc R . . C9 C 0.05028(11) 0.1660(2) 0.52999(13) 0.0197(4) Uani 1 1 d . . . C10 C 0.00455(12) 0.2755(2) 0.49412(13) 0.0204(4) Uani 1 1 d . . . H10 H -0.0194 0.3299 0.5250 0.024 Uiso 1 1 calc R . . C11 C -0.00477(11) 0.3023(2) 0.41228(13) 0.0197(4) Uani 1 1 d . . . C12 C 0.10603(12) 0.0499(2) 0.34211(12) 0.0201(4) Uani 1 1 d . . . O1 O 0.15114(9) -0.04278(18) 0.36572(10) 0.0289(4) Uani 1 1 d . . . O2 O 0.08295(8) 0.09587(16) 0.26908(9) 0.0229(3) Uani 1 1 d . . . C13 C 0.05721(13) 0.1292(2) 0.61749(13) 0.0229(5) Uani 1 1 d . . . O3 O 0.10225(9) 0.02523(18) 0.64387(10) 0.0292(4) Uani 1 1 d . . . H3 H 0.0974 -0.0039 0.6883 0.044 Uiso 1 1 calc R . . O4 O 0.02396(10) 0.1884(2) 0.65721(11) 0.0380(4) Uani 1 1 d . . . C14 C -0.05792(12) 0.4065(2) 0.36049(13) 0.0216(5) Uani 1 1 d . . . O5 O -0.08973(9) 0.48616(17) 0.39542(10) 0.0277(4) Uani 1 1 d . . . O6 O -0.06694(8) 0.39766(16) 0.28354(9) 0.0231(4) Uani 1 1 d . . . O7 O 0.42319(16) 0.0816(3) 0.1358(2) 0.0919(11) Uani 1 1 d . . . O8 O 0.32551(16) 0.2552(3) 0.0175(2) 0.0811(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0193(10) 0.0224(11) 0.0238(11) 0.0012(9) 0.0060(9) -0.0023(9) N1 0.0310(10) 0.0271(10) 0.0236(10) 0.0062(8) 0.0112(8) 0.0075(8) C2 0.0461(15) 0.0310(13) 0.0266(12) 0.0034(10) 0.0168(11) 0.0073(12) C3 0.0331(13) 0.0357(14) 0.0227(11) 0.0015(10) 0.0067(10) 0.0007(11) N2 0.0264(10) 0.0301(11) 0.0238(10) 0.0040(8) 0.0075(8) 0.0059(9) C4 0.0179(10) 0.0248(11) 0.0214(10) 0.0010(9) 0.0058(9) -0.0019(9) C5 0.0243(11) 0.0253(11) 0.0284(12) 0.0003(9) 0.0097(10) 0.0034(9) C6 0.0268(12) 0.0259(12) 0.0249(11) 0.0048(9) 0.0075(10) 0.0042(10) Ni1 0.0220(2) 0.0203(2) 0.0137(2) 0.000 0.00331(15) 0.000 N3 0.0181(8) 0.0201(9) 0.0142(8) -0.0021(6) 0.0041(7) -0.0013(7) C7 0.0170(10) 0.0194(10) 0.0158(9) -0.0026(8) 0.0034(8) -0.0009(8) C8 0.0190(10) 0.0200(10) 0.0186(10) 0.0009(8) 0.0030(8) 0.0001(8) C9 0.0202(10) 0.0223(10) 0.0165(10) 0.0000(8) 0.0051(8) -0.0034(8) C10 0.0196(10) 0.0228(11) 0.0187(10) -0.0042(8) 0.0054(9) -0.0003(8) C11 0.0194(10) 0.0175(10) 0.0214(10) -0.0029(8) 0.0045(9) -0.0005(9) C12 0.0215(10) 0.0215(10) 0.0172(10) -0.0020(8) 0.0056(8) -0.0011(9) O1 0.0317(9) 0.0310(9) 0.0246(8) -0.0003(7) 0.0087(7) 0.0124(8) O2 0.0289(8) 0.0249(8) 0.0155(7) -0.0011(6) 0.0075(6) 0.0043(7) C13 0.0249(11) 0.0252(11) 0.0191(10) 0.0008(9) 0.0071(9) -0.0023(9) O3 0.0371(9) 0.0331(9) 0.0201(8) 0.0087(7) 0.0127(7) 0.0067(8) O4 0.0476(11) 0.0477(11) 0.0236(9) 0.0046(8) 0.0183(8) 0.0145(9) C14 0.0193(10) 0.0229(11) 0.0214(10) -0.0013(8) 0.0041(9) -0.0002(9) O5 0.0279(9) 0.0279(9) 0.0272(8) -0.0025(7) 0.0078(7) 0.0095(7) O6 0.0244(8) 0.0254(8) 0.0172(7) 0.0004(6) 0.0023(6) 0.0034(6) O7 0.093(2) 0.0532(16) 0.165(3) 0.0243(18) 0.094(2) 0.0116(15) O8 0.0656(17) 0.094(2) 0.088(2) -0.0511(16) 0.0299(16) -0.0205(14) _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 C1 N1 1.304(3) . ? C1 N2 1.321(3) . ? C1 C4 1.475(3) . ? N1 C2 1.470(3) . ? N1 H1 0.8800 . ? C2 C3 1.526(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N2 1.474(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N2 H2 0.8800 . ? C4 C6 1.390(3) . ? C4 C5 1.395(3) . ? C5 C6 1.389(3) 7_556 ? C5 H5 0.9500 . ? C6 C5 1.389(3) 7_556 ? C6 H6 0.9500 . ? Ni1 N3 1.9612(18) . ? Ni1 N3 1.9612(18) 2 ? Ni1 O2 2.1165(15) . ? Ni1 O2 2.1165(15) 2 ? Ni1 O6 2.1192(16) . ? Ni1 O6 2.1192(16) 2 ? N3 C11 1.330(3) . ? N3 C7 1.339(3) . ? C7 C8 1.389(3) . ? C7 C12 1.516(3) . ? C8 C9 1.395(3) . ? C8 H8 0.9500 . ? C9 C10 1.397(3) . ? C9 C13 1.506(3) . ? C10 C11 1.383(3) . ? C10 H10 0.9500 . ? C11 C14 1.522(3) . ? C12 O1 1.229(3) . ? C12 O2 1.279(3) . ? C13 O4 1.201(3) . ? C13 O3 1.315(3) . ? O3 H3 0.8400 . ? C14 O5 1.236(3) . ? C14 O6 1.280(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 N1 C1 N2 112.2(2) . . ? N1 C1 C4 124.3(2) . . ? N2 C1 C4 123.5(2) . . ? C1 N1 C2 110.86(19) . . ? C1 N1 H1 124.6 . . ? C2 N1 H1 124.6 . . ? N1 C2 C3 102.7(2) . . ? N1 C2 H2A 111.2 . . ? C3 C2 H2A 111.2 . . ? N1 C2 H2B 111.2 . . ? C3 C2 H2B 111.2 . . ? H2A C2 H2B 109.1 . . ? N2 C3 C2 102.00(19) . . ? N2 C3 H3A 111.4 . . ? C2 C3 H3A 111.4 . . ? N2 C3 H3B 111.4 . . ? C2 C3 H3B 111.4 . . ? H3A C3 H3B 109.2 . . ? C1 N2 C3 110.5(2) . . ? C1 N2 H2 124.7 . . ? C3 N2 H2 124.7 . . ? C6 C4 C5 119.6(2) . . ? C6 C4 C1 120.1(2) . . ? C5 C4 C1 120.3(2) . . ? C6 C5 C4 120.0(2) 7_556 . ? C6 C5 H5 120.0 7_556 . ? C4 C5 H5 120.0 . . ? C5 C6 C4 120.4(2) 7_556 . ? C5 C6 H6 119.8 7_556 . ? C4 C6 H6 119.8 . . ? N3 Ni1 N3 169.08(10) . 2 ? N3 Ni1 O2 77.97(7) . . ? N3 Ni1 O2 94.42(7) 2 . ? N3 Ni1 O2 94.42(7) . 2 ? N3 Ni1 O2 77.97(7) 2 2 ? O2 Ni1 O2 92.71(9) . 2 ? N3 Ni1 O6 78.62(6) . . ? N3 Ni1 O6 109.10(7) 2 . ? O2 Ni1 O6 156.47(6) . . ? O2 Ni1 O6 91.43(6) 2 . ? N3 Ni1 O6 109.10(7) . 2 ? N3 Ni1 O6 78.62(6) 2 2 ? O2 Ni1 O6 91.43(6) . 2 ? O2 Ni1 O6 156.47(6) 2 2 ? O6 Ni1 O6 93.97(9) . 2 ? C11 N3 C7 121.80(19) . . ? C11 N3 Ni1 118.81(14) . . ? C7 N3 Ni1 118.29(14) . . ? N3 C7 C8 120.6(2) . . ? N3 C7 C12 113.32(18) . . ? C8 C7 C12 126.07(19) . . ? C7 C8 C9 118.20(19) . . ? C7 C8 H8 120.9 . . ? C9 C8 H8 120.9 . . ? C8 C9 C10 120.2(2) . . ? C8 C9 C13 121.04(19) . . ? C10 C9 C13 118.7(2) . . ? C11 C10 C9 117.9(2) . . ? C11 C10 H10 121.0 . . ? C9 C10 H10 121.0 . . ? N3 C11 C10 121.3(2) . . ? N3 C11 C14 112.84(19) . . ? C10 C11 C14 125.7(2) . . ? O1 C12 O2 126.0(2) . . ? O1 C12 C7 119.96(19) . . ? O2 C12 C7 114.02(18) . . ? C12 O2 Ni1 115.18(14) . . ? O4 C13 O3 124.8(2) . . ? O4 C13 C9 122.6(2) . . ? O3 C13 C9 112.51(19) . . ? C13 O3 H3 109.5 . . ? O5 C14 O6 126.7(2) . . ? O5 C14 C11 118.04(19) . . ? O6 C14 C11 115.21(19) . . ? C14 O6 Ni1 114.13(14) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.04 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.796 _refine_diff_density_min -0.727 _refine_diff_density_rms 0.088 _database_code_depnum_ccdc_archive 'CCDC 949325' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H6 N2 O12 Zn, C12 H16 N4, 4(H2 O)' _chemical_formula_sum 'C28 H30 N6 O16 Zn' _chemical_formula_weight 771.95 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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 _symmetry_space_group_name_Hall '-C 2yc' 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 19.2791(5) _cell_length_b 9.6312(3) _cell_length_c 17.0771(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.809(14) _cell_angle_gamma 90.00 _cell_volume 3019.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3023 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1592 _exptl_absorpt_coefficient_mu 0.906 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8836 _exptl_absorpt_correction_T_max 0.8991 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6873 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 30.04 _reflns_number_total 4400 _reflns_number_gt 3442 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+3.5616P] 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 4400 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1084 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.25877(10) 0.23990(19) 0.33512(12) 0.0197(4) Uani 1 1 d . . . N1 N 0.30665(9) 0.16656(18) 0.31309(10) 0.0234(4) Uani 1 1 d . . . H1 H 0.3383 0.1098 0.3458 0.028 Uiso 1 1 calc R . . C2 C 0.30041(13) 0.1917(2) 0.22608(13) 0.0305(5) Uani 1 1 d . . . H2A H 0.2960 0.1034 0.1953 0.037 Uiso 1 1 calc R . . H2B H 0.3430 0.2440 0.2208 0.037 Uiso 1 1 calc R . . C3 C 0.23065(13) 0.2777(2) 0.19589(13) 0.0305(5) Uani 1 1 d . . . H3A H 0.2383 0.3621 0.1665 0.037 Uiso 1 1 calc R . . H3B H 0.1902 0.2227 0.1593 0.037 Uiso 1 1 calc R . . N2 N 0.21637(9) 0.31320(19) 0.27375(10) 0.0245(4) Uani 1 1 d . . . H2 H 0.1841 0.3746 0.2785 0.029 Uiso 1 1 calc R . . C4 C 0.25404(10) 0.24409(19) 0.42008(12) 0.0200(4) Uani 1 1 d . . . C5 C 0.28842(11) 0.1430(2) 0.47700(12) 0.0236(4) Uani 1 1 d . . . H5 H 0.3146 0.0701 0.4614 0.028 Uiso 1 1 calc R . . C6 C 0.21576(11) 0.3507(2) 0.44322(12) 0.0239(4) Uani 1 1 d . . . H6 H 0.1923 0.4196 0.4043 0.029 Uiso 1 1 calc R . . Zn1 Zn 0.0000 0.26502(3) 0.2500 0.02172(11) Uani 1 2 d S . . N3 N 0.02915(8) 0.22811(15) 0.37160(9) 0.0159(3) Uani 1 1 d . . . C7 C 0.07404(10) 0.12346(18) 0.40492(11) 0.0159(3) Uani 1 1 d . . . C8 C 0.08580(10) 0.08572(19) 0.48650(11) 0.0175(3) Uani 1 1 d . . . H8 H 0.1170 0.0104 0.5101 0.021 Uiso 1 1 calc R . . C9 C 0.05057(10) 0.16138(19) 0.53276(11) 0.0179(4) Uani 1 1 d . . . C10 C 0.00481(10) 0.2713(2) 0.49729(12) 0.0189(4) Uani 1 1 d . . . H10 H -0.0189 0.3245 0.5284 0.023 Uiso 1 1 calc R . . C11 C -0.00505(10) 0.30092(19) 0.41505(11) 0.0170(3) Uani 1 1 d . . . C12 C 0.10728(10) 0.05137(19) 0.34573(11) 0.0184(4) Uani 1 1 d . . . O1 O 0.14994(8) -0.04526(16) 0.37032(9) 0.0290(3) Uani 1 1 d . . . O2 O 0.08795(8) 0.10242(14) 0.27336(8) 0.0225(3) Uani 1 1 d . . . C13 C 0.05848(11) 0.1225(2) 0.62081(11) 0.0207(4) Uani 1 1 d . . . O3 O 0.10359(8) 0.01776(16) 0.64720(9) 0.0273(3) Uani 1 1 d . . . H3 H 0.0975 -0.0151 0.6902 0.041 Uiso 1 1 calc R . . O4 O 0.02589(9) 0.18207(19) 0.66061(9) 0.0349(4) Uani 1 1 d . . . C14 C -0.05784(10) 0.40849(19) 0.36501(12) 0.0192(4) Uani 1 1 d . . . O5 O -0.08933(8) 0.48452(15) 0.40163(9) 0.0260(3) Uani 1 1 d . . . O6 O -0.06724(8) 0.40722(14) 0.28757(8) 0.0231(3) Uani 1 1 d . . . O7 O 0.42307(15) 0.0857(2) 0.1353(2) 0.0899(10) Uani 1 1 d . . . O8 O 0.32506(14) 0.2544(2) 0.01388(17) 0.0676(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0199(9) 0.0191(8) 0.0195(9) 0.0014(7) 0.0051(7) -0.0026(7) N1 0.0286(9) 0.0233(8) 0.0197(8) 0.0044(7) 0.0093(7) 0.0059(7) C2 0.0423(12) 0.0310(11) 0.0215(10) 0.0025(9) 0.0147(9) 0.0063(10) C3 0.0352(12) 0.0359(11) 0.0203(10) 0.0023(9) 0.0082(9) 0.0047(9) N2 0.0257(8) 0.0270(9) 0.0208(8) 0.0036(7) 0.0070(7) 0.0054(7) C4 0.0174(8) 0.0230(9) 0.0199(9) -0.0004(7) 0.0062(7) -0.0018(7) C5 0.0245(10) 0.0237(9) 0.0245(10) 0.0022(8) 0.0103(8) 0.0048(8) C6 0.0253(10) 0.0239(9) 0.0225(10) 0.0042(8) 0.0075(8) 0.0043(8) Zn1 0.02912(19) 0.02341(18) 0.01104(16) 0.000 0.00378(12) 0.000 N3 0.0176(7) 0.0165(7) 0.0135(7) -0.0009(6) 0.0045(6) -0.0001(6) C7 0.0179(8) 0.0163(8) 0.0134(8) -0.0007(6) 0.0047(6) -0.0019(6) C8 0.0191(8) 0.0176(8) 0.0151(8) 0.0006(7) 0.0045(7) -0.0003(7) C9 0.0212(9) 0.0202(8) 0.0127(8) -0.0009(7) 0.0059(7) -0.0037(7) C10 0.0197(8) 0.0218(9) 0.0159(8) -0.0036(7) 0.0065(7) -0.0020(7) C11 0.0192(8) 0.0160(8) 0.0156(8) -0.0031(7) 0.0053(7) -0.0004(7) C12 0.0204(8) 0.0196(8) 0.0153(8) -0.0014(7) 0.0060(7) -0.0006(7) O1 0.0341(8) 0.0303(8) 0.0238(7) 0.0016(6) 0.0108(6) 0.0147(6) O2 0.0305(7) 0.0244(7) 0.0138(6) 0.0000(5) 0.0088(5) 0.0047(6) C13 0.0241(9) 0.0242(9) 0.0140(8) -0.0007(7) 0.0063(7) -0.0037(7) O3 0.0372(8) 0.0297(8) 0.0178(7) 0.0073(6) 0.0126(6) 0.0049(6) O4 0.0424(9) 0.0467(10) 0.0206(7) 0.0035(7) 0.0169(7) 0.0113(8) C14 0.0184(8) 0.0186(8) 0.0192(9) -0.0017(7) 0.0034(7) -0.0001(7) O5 0.0258(7) 0.0251(7) 0.0270(7) -0.0023(6) 0.0078(6) 0.0090(6) O6 0.0264(7) 0.0232(7) 0.0157(6) -0.0006(5) 0.0007(5) 0.0054(6) O7 0.0881(18) 0.0570(14) 0.161(3) 0.0463(17) 0.091(2) 0.0250(13) O8 0.0605(14) 0.0713(15) 0.0735(17) -0.0381(12) 0.0240(13) -0.0139(11) _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 C1 N1 1.306(3) . ? C1 N2 1.319(2) . ? C1 C4 1.482(3) . ? N1 C2 1.474(3) . ? N1 H1 0.8800 . ? C2 C3 1.528(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N2 1.478(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N2 H2 0.8800 . ? C4 C6 1.390(3) . ? C4 C5 1.392(3) . ? C5 C6 1.391(3) 7_556 ? C5 H5 0.9500 . ? C6 C5 1.391(3) 7_556 ? C6 H6 0.9500 . ? Zn1 N3 2.0100(15) . ? Zn1 N3 2.0101(15) 2 ? Zn1 O6 2.1157(14) . ? Zn1 O6 2.1157(14) 2 ? Zn1 O2 2.2523(14) 2 ? Zn1 O2 2.2523(14) . ? N3 C11 1.333(2) . ? N3 C7 1.337(2) . ? C7 C8 1.390(2) . ? C7 C12 1.520(3) . ? C8 C9 1.395(3) . ? C8 H8 0.9500 . ? C9 C10 1.393(3) . ? C9 C13 1.511(2) . ? C10 C11 1.388(3) . ? C10 H10 0.9500 . ? C11 C14 1.519(3) . ? C12 O1 1.228(2) . ? C12 O2 1.275(2) . ? C13 O4 1.203(2) . ? C13 O3 1.318(2) . ? O3 H3 0.8400 . ? C14 O5 1.236(2) . ? C14 O6 1.279(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 112.43(18) . . ? N1 C1 C4 123.88(18) . . ? N2 C1 C4 123.66(18) . . ? C1 N1 C2 110.76(17) . . ? C1 N1 H1 124.6 . . ? C2 N1 H1 124.6 . . ? N1 C2 C3 102.80(17) . . ? N1 C2 H2A 111.2 . . ? C3 C2 H2A 111.2 . . ? N1 C2 H2B 111.2 . . ? C3 C2 H2B 111.2 . . ? H2A C2 H2B 109.1 . . ? N2 C3 C2 102.04(17) . . ? N2 C3 H3A 111.4 . . ? C2 C3 H3A 111.4 . . ? N2 C3 H3B 111.4 . . ? C2 C3 H3B 111.4 . . ? H3A C3 H3B 109.2 . . ? C1 N2 C3 110.50(17) . . ? C1 N2 H2 124.8 . . ? C3 N2 H2 124.8 . . ? C6 C4 C5 119.90(18) . . ? C6 C4 C1 119.70(17) . . ? C5 C4 C1 120.39(17) . . ? C6 C5 C4 119.73(19) 7_556 . ? C6 C5 H5 120.1 7_556 . ? C4 C5 H5 120.1 . . ? C4 C6 C5 120.37(18) . 7_556 ? C4 C6 H6 119.8 . . ? C5 C6 H6 119.8 7_556 . ? N3 Zn1 N3 159.63(9) . 2 ? N3 Zn1 O6 78.75(6) . . ? N3 Zn1 O6 115.09(6) 2 . ? N3 Zn1 O6 115.09(6) . 2 ? N3 Zn1 O6 78.75(6) 2 2 ? O6 Zn1 O6 99.32(8) . 2 ? N3 Zn1 O2 91.00(6) . 2 ? N3 Zn1 O2 74.73(6) 2 2 ? O6 Zn1 O2 90.34(5) . 2 ? O6 Zn1 O2 153.41(5) 2 2 ? N3 Zn1 O2 74.73(6) . . ? N3 Zn1 O2 91.00(6) 2 . ? O6 Zn1 O2 153.41(5) . . ? O6 Zn1 O2 90.33(5) 2 . ? O2 Zn1 O2 91.90(7) 2 . ? C11 N3 C7 121.71(16) . . ? C11 N3 Zn1 116.90(12) . . ? C7 N3 Zn1 120.87(12) . . ? N3 C7 C8 120.65(17) . . ? N3 C7 C12 114.26(15) . . ? C8 C7 C12 125.06(16) . . ? C7 C8 C9 118.22(17) . . ? C7 C8 H8 120.9 . . ? C9 C8 H8 120.9 . . ? C10 C9 C8 120.28(17) . . ? C10 C9 C13 118.62(17) . . ? C8 C9 C13 121.05(17) . . ? C11 C10 C9 117.96(17) . . ? C11 C10 H10 121.0 . . ? C9 C10 H10 121.0 . . ? N3 C11 C10 121.16(17) . . ? N3 C11 C14 113.95(16) . . ? C10 C11 C14 124.77(17) . . ? O1 C12 O2 126.18(18) . . ? O1 C12 C7 119.56(16) . . ? O2 C12 C7 114.25(16) . . ? C12 O2 Zn1 114.88(12) . . ? O4 C13 O3 125.16(18) . . ? O4 C13 C9 122.19(18) . . ? O3 C13 C9 112.65(16) . . ? C13 O3 H3 109.5 . . ? O5 C14 O6 126.35(18) . . ? O5 C14 C11 117.87(17) . . ? O6 C14 C11 115.72(16) . . ? C14 O6 Zn1 114.43(12) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.04 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.712 _refine_diff_density_min -0.731 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 949326' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H6 Co N2 O12, C12 H16 N4, 4(H2 O)' _chemical_formula_sum 'C28 H30 Co N6 O16' _chemical_formula_weight 765.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 '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 _symmetry_space_group_name_Hall '-C 2yc' 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 19.2011(5) _cell_length_b 9.6470(3) _cell_length_c 17.1082(6) _cell_angle_alpha 90.00 _cell_angle_beta 107.494(4) _cell_angle_gamma 90.00 _cell_volume 3022.43(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4074 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1580 _exptl_absorpt_coefficient_mu 0.660 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9132 _exptl_absorpt_correction_T_max 0.9250 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7687 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_sigmaI/netI 0.1014 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 30.02 _reflns_number_total 4417 _reflns_number_gt 2414 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0605P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4417 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1220 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1390 _refine_ls_wR_factor_gt 0.1149 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.25832(14) 0.2400(2) 0.33550(17) 0.0228(6) Uani 1 1 d . . . N1 N 0.30596(12) 0.1658(2) 0.31266(13) 0.0276(5) Uani 1 1 d . . . H1 H 0.3376 0.1087 0.3448 0.033 Uiso 1 1 calc R . . C2 C 0.29933(16) 0.1908(3) 0.22586(18) 0.0343(7) Uani 1 1 d . . . H2A H 0.2949 0.1026 0.1952 0.041 Uiso 1 1 calc R . . H2B H 0.3418 0.2432 0.2200 0.041 Uiso 1 1 calc R . . C3 C 0.22949(16) 0.2760(3) 0.19637(17) 0.0335(7) Uani 1 1 d . . . H3A H 0.2368 0.3600 0.1665 0.040 Uiso 1 1 calc R . . H3B H 0.1889 0.2207 0.1606 0.040 Uiso 1 1 calc R . . N2 N 0.21570(12) 0.3121(2) 0.27422(14) 0.0285(5) Uani 1 1 d . . . H2 H 0.1834 0.3735 0.2791 0.034 Uiso 1 1 calc R . . C4 C 0.25384(13) 0.2438(3) 0.41970(16) 0.0231(6) Uani 1 1 d . . . C5 C 0.28829(14) 0.1439(3) 0.47691(17) 0.0268(6) Uani 1 1 d . . . H5 H 0.3145 0.0709 0.4612 0.032 Uiso 1 1 calc R . . C6 C 0.21525(15) 0.3500(3) 0.44358(17) 0.0277(6) Uani 1 1 d . . . H6 H 0.1913 0.4186 0.4050 0.033 Uiso 1 1 calc R . . Co1 Co 0.0000 0.25330(5) 0.2500 0.02241(16) Uani 1 2 d S . . N3 N 0.02949(11) 0.2266(2) 0.37206(12) 0.0181(4) Uani 1 1 d . . . C7 C 0.07446(13) 0.1220(2) 0.40560(15) 0.0183(5) Uani 1 1 d . . . C8 C 0.08617(13) 0.0858(2) 0.48650(15) 0.0204(5) Uani 1 1 d . . . H8 H 0.1177 0.0111 0.5102 0.024 Uiso 1 1 calc R . . C9 C 0.05056(13) 0.1617(3) 0.53284(15) 0.0213(5) Uani 1 1 d . . . C10 C 0.00535(14) 0.2709(2) 0.49689(16) 0.0211(6) Uani 1 1 d . . . H10 H -0.0183 0.3249 0.5279 0.025 Uiso 1 1 calc R . . C11 C -0.00477(13) 0.2999(3) 0.41495(15) 0.0193(5) Uani 1 1 d . . . C12 C 0.10691(13) 0.0501(3) 0.34543(15) 0.0213(6) Uani 1 1 d . . . O1 O 0.15052(10) -0.04458(19) 0.36908(11) 0.0306(5) Uani 1 1 d . . . O2 O 0.08627(9) 0.10144(17) 0.27273(10) 0.0246(4) Uani 1 1 d . . . C13 C 0.05841(14) 0.1243(3) 0.62041(16) 0.0245(6) Uani 1 1 d . . . O3 O 0.10372(10) 0.01996(19) 0.64699(12) 0.0308(5) Uani 1 1 d . . . H3 H 0.0990 -0.0099 0.6912 0.046 Uiso 1 1 calc R . . O4 O 0.02499(11) 0.1828(2) 0.66000(12) 0.0386(5) Uani 1 1 d . . . C14 C -0.05733(14) 0.4061(3) 0.36394(16) 0.0229(6) Uani 1 1 d . . . O5 O -0.08942(9) 0.48430(18) 0.39930(12) 0.0287(5) Uani 1 1 d . . . O6 O -0.06552(9) 0.40302(17) 0.28713(11) 0.0266(4) Uani 1 1 d . . . O7 O 0.42259(16) 0.0852(3) 0.1351(2) 0.0997(12) Uani 1 1 d . . . O8 O 0.32508(15) 0.2555(3) 0.01443(19) 0.0774(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0205(13) 0.0210(13) 0.0266(14) -0.0006(12) 0.0068(11) -0.0024(11) N1 0.0332(13) 0.0269(12) 0.0234(13) 0.0056(10) 0.0095(11) 0.0065(10) C2 0.0474(18) 0.0323(16) 0.0265(16) 0.0027(13) 0.0162(15) 0.0041(14) C3 0.0377(17) 0.0392(17) 0.0235(16) 0.0025(12) 0.0094(14) 0.0009(13) N2 0.0297(13) 0.0302(13) 0.0263(13) 0.0038(10) 0.0097(11) 0.0048(10) C4 0.0179(12) 0.0280(14) 0.0231(14) -0.0020(11) 0.0058(11) -0.0042(11) C5 0.0279(15) 0.0261(14) 0.0282(16) 0.0026(12) 0.0110(13) 0.0042(12) C6 0.0283(15) 0.0304(15) 0.0238(15) 0.0031(12) 0.0068(12) 0.0013(12) Co1 0.0264(3) 0.0241(3) 0.0157(3) 0.000 0.0049(2) 0.000 N3 0.0183(10) 0.0221(11) 0.0139(11) -0.0020(8) 0.0048(9) -0.0014(9) C7 0.0175(12) 0.0208(13) 0.0159(13) -0.0008(10) 0.0038(11) -0.0017(10) C8 0.0196(12) 0.0219(13) 0.0181(13) 0.0009(10) 0.0034(11) -0.0013(11) C9 0.0229(13) 0.0255(13) 0.0156(13) -0.0013(11) 0.0057(11) -0.0044(11) C10 0.0218(13) 0.0244(14) 0.0183(13) -0.0053(10) 0.0079(11) -0.0034(11) C11 0.0173(12) 0.0207(12) 0.0191(14) -0.0029(10) 0.0041(11) -0.0010(10) C12 0.0222(13) 0.0212(13) 0.0207(14) -0.0044(11) 0.0064(12) -0.0024(11) O1 0.0332(11) 0.0323(11) 0.0262(11) 0.0002(9) 0.0090(9) 0.0131(9) O2 0.0318(10) 0.0271(10) 0.0165(10) -0.0006(8) 0.0098(8) 0.0045(8) C13 0.0273(14) 0.0274(15) 0.0179(14) 0.0000(11) 0.0057(12) -0.0042(12) O3 0.0403(11) 0.0330(11) 0.0229(11) 0.0097(9) 0.0151(9) 0.0057(9) O4 0.0471(13) 0.0494(13) 0.0254(11) 0.0024(10) 0.0201(10) 0.0100(11) C14 0.0207(13) 0.0231(14) 0.0237(15) -0.0024(11) 0.0049(12) -0.0023(11) O5 0.0275(10) 0.0289(11) 0.0293(11) -0.0043(8) 0.0079(9) 0.0087(8) O6 0.0311(10) 0.0279(10) 0.0186(10) 0.0010(8) 0.0045(9) 0.0060(8) O7 0.101(2) 0.0618(19) 0.175(3) 0.041(2) 0.099(3) 0.0225(17) O8 0.0677(18) 0.086(2) 0.083(2) -0.0448(16) 0.0286(17) -0.0218(14) _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 C1 N1 1.310(3) . ? C1 N2 1.318(3) . ? C1 C4 1.469(4) . ? N1 C2 1.472(3) . ? N1 H1 0.8800 . ? C2 C3 1.523(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N2 1.476(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N2 H2 0.8800 . ? C4 C5 1.391(4) . ? C4 C6 1.396(4) . ? C5 C6 1.383(3) 7_556 ? C5 H5 0.9500 . ? C6 C5 1.383(3) 7_556 ? C6 H6 0.9500 . ? Co1 N3 2.009(2) . ? Co1 N3 2.009(2) 2 ? Co1 O6 2.1336(16) 2 ? Co1 O6 2.1337(16) . ? Co1 O2 2.1572(17) 2 ? Co1 O2 2.1572(17) . ? N3 C11 1.327(3) . ? N3 C7 1.340(3) . ? C7 C8 1.379(3) . ? C7 C12 1.521(3) . ? C8 C9 1.399(3) . ? C8 H8 0.9500 . ? C9 C10 1.385(4) . ? C9 C13 1.504(3) . ? C10 C11 1.385(3) . ? C10 H10 0.9500 . ? C11 C14 1.517(4) . ? C12 O1 1.223(3) . ? C12 O2 1.286(3) . ? C13 O4 1.204(3) . ? C13 O3 1.319(3) . ? O3 H3 0.8400 . ? C14 O5 1.241(3) . ? C14 O6 1.276(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 N1 C1 N2 111.9(2) . . ? N1 C1 C4 123.9(2) . . ? N2 C1 C4 124.2(2) . . ? C1 N1 C2 110.8(2) . . ? C1 N1 H1 124.6 . . ? C2 N1 H1 124.6 . . ? N1 C2 C3 102.9(2) . . ? N1 C2 H2A 111.2 . . ? C3 C2 H2A 111.2 . . ? N1 C2 H2B 111.2 . . ? C3 C2 H2B 111.2 . . ? H2A C2 H2B 109.1 . . ? N2 C3 C2 102.0(2) . . ? N2 C3 H3A 111.4 . . ? C2 C3 H3A 111.4 . . ? N2 C3 H3B 111.4 . . ? C2 C3 H3B 111.4 . . ? H3A C3 H3B 109.2 . . ? C1 N2 C3 110.9(2) . . ? C1 N2 H2 124.6 . . ? C3 N2 H2 124.6 . . ? C5 C4 C6 119.0(2) . . ? C5 C4 C1 121.1(2) . . ? C6 C4 C1 119.9(2) . . ? C6 C5 C4 120.6(2) 7_556 . ? C6 C5 H5 119.7 7_556 . ? C4 C5 H5 119.7 . . ? C5 C6 C4 120.4(2) 7_556 . ? C5 C6 H6 119.8 7_556 . ? C4 C6 H6 119.8 . . ? N3 Co1 N3 165.28(11) . 2 ? N3 Co1 O6 112.89(7) . 2 ? N3 Co1 O6 77.55(7) 2 2 ? N3 Co1 O6 77.55(7) . . ? N3 Co1 O6 112.89(7) 2 . ? O6 Co1 O6 94.79(9) 2 . ? N3 Co1 O2 93.54(7) . 2 ? N3 Co1 O2 76.37(7) 2 2 ? O6 Co1 O2 153.57(7) 2 2 ? O6 Co1 O2 91.37(7) . 2 ? N3 Co1 O2 76.37(7) . . ? N3 Co1 O2 93.53(7) 2 . ? O6 Co1 O2 91.37(7) 2 . ? O6 Co1 O2 153.57(7) . . ? O2 Co1 O2 94.46(9) 2 . ? C11 N3 C7 121.8(2) . . ? C11 N3 Co1 118.35(17) . . ? C7 N3 Co1 119.04(15) . . ? N3 C7 C8 120.7(2) . . ? N3 C7 C12 113.3(2) . . ? C8 C7 C12 126.0(2) . . ? C7 C8 C9 118.5(2) . . ? C7 C8 H8 120.8 . . ? C9 C8 H8 120.8 . . ? C10 C9 C8 119.6(2) . . ? C10 C9 C13 119.1(2) . . ? C8 C9 C13 121.3(2) . . ? C11 C10 C9 118.8(2) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? N3 C11 C10 120.7(2) . . ? N3 C11 C14 113.3(2) . . ? C10 C11 C14 125.8(2) . . ? O1 C12 O2 126.1(2) . . ? O1 C12 C7 119.7(2) . . ? O2 C12 C7 114.1(2) . . ? C12 O2 Co1 115.64(15) . . ? O4 C13 O3 124.9(2) . . ? O4 C13 C9 122.5(3) . . ? O3 C13 C9 112.6(2) . . ? C13 O3 H3 109.5 . . ? O5 C14 O6 126.2(2) . . ? O5 C14 C11 118.2(2) . . ? O6 C14 C11 115.6(2) . . ? C14 O6 Co1 114.90(16) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.630 _refine_diff_density_min -0.673 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 949327'