# 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H20 Cd N4 O5' _chemical_formula_weight 496.79 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' Cd Cd -0.8075 1.2024 '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 12.0288(9) _cell_length_b 10.2873(8) _cell_length_c 17.0184(15) _cell_angle_alpha 90.00 _cell_angle_beta 96.400(6) _cell_angle_gamma 90.00 _cell_volume 2092.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5269 _cell_measurement_theta_min 2.1931 _cell_measurement_theta_max 27.4719 _exptl_crystal_description lamellar _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 1.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8293 _exptl_absorpt_correction_T_max 0.8997 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SCXmini CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16153 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4751 _reflns_number_gt 4208 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0780P)^2^+2.4070P] 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 SHELXL _refine_ls_extinction_coef 0.0071(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4751 _refine_ls_number_parameters 290 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1442 _refine_ls_wR_factor_gt 0.1366 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 Cd1 Cd 0.34609(2) 0.50694(2) 0.193469(16) 0.03593(15) Uani 1 1 d . . . C5 C 0.0765(4) 0.4943(3) 0.3335(3) 0.0387(9) Uani 1 1 d . . . C4 C 0.0359(3) 0.3786(4) 0.3623(2) 0.0393(9) Uani 1 1 d . . . C3 C 0.0240(4) 0.6105(4) 0.3493(3) 0.0482(10) Uani 1 1 d . . . H3A H 0.0495 0.6882 0.3299 0.058 Uiso 1 1 calc R . . C2 C -0.0656(4) 0.6114(5) 0.3936(3) 0.0601(13) Uani 1 1 d . . . H2A H -0.1001 0.6897 0.4035 0.072 Uiso 1 1 calc R . . C10 C 0.6936(3) 0.2681(4) 0.5195(2) 0.0414(9) Uani 1 1 d . . . C1 C -0.0544(4) 0.3826(5) 0.4079(3) 0.0526(11) Uani 1 1 d . . . H1A H -0.0811 0.3060 0.4280 0.063 Uiso 1 1 calc R . . O2 O 0.1881(2) 0.2262(3) 0.37043(19) 0.0504(7) Uani 1 1 d . . . C15 C 0.4781(3) 0.2129(4) 0.3658(2) 0.0444(10) Uani 1 1 d . . . N4 N 0.7396(3) 0.2228(3) 0.5896(2) 0.0415(7) Uani 1 1 d . . . H4A H 0.7324 0.2601 0.6340 0.050 Uiso 1 1 calc R . . O1 O 0.0227(3) 0.1606(3) 0.3187(2) 0.0612(9) Uani 1 1 d . . . C7 C -0.1035(5) 0.4988(4) 0.4227(4) 0.0636(15) Uani 1 1 d . . . H7A H -0.1632 0.5007 0.4529 0.076 Uiso 1 1 calc R . . C12 C 0.7214(3) 0.1815(4) 0.4628(2) 0.0376(8) Uani 1 1 d . . . C9 C 0.7871(3) 0.0855(4) 0.5056(2) 0.0389(8) Uani 1 1 d . . . C8 C 0.8394(4) -0.0317(5) 0.4727(3) 0.0543(12) Uani 1 1 d . . . H8A H 0.8800 -0.0797 0.5151 0.081 Uiso 1 1 calc R . . H8B H 0.8898 -0.0048 0.4359 0.081 Uiso 1 1 calc R . . H8C H 0.7821 -0.0860 0.4462 0.081 Uiso 1 1 calc R . . N3 N 0.4542(3) 0.3786(3) 0.2800(2) 0.0407(7) Uani 1 1 d . . . C14 C 0.5822(3) 0.2473(4) 0.3461(2) 0.0404(9) Uani 1 1 d . . . N1 N 0.7983(3) 0.1123(3) 0.58271(19) 0.0398(7) Uani 1 1 d . . . N2 N 0.4047(3) 0.2930(3) 0.3258(2) 0.0452(8) Uani 1 1 d . . . H2B H 0.3338 0.2904 0.3289 0.054 Uiso 1 1 calc R . . C18 C 0.5631(3) 0.3512(4) 0.2930(2) 0.0413(9) Uani 1 1 d . . . C13 C 0.6922(4) 0.1827(4) 0.3746(2) 0.0495(10) Uani 1 1 d . . . H13A H 0.7514 0.2271 0.3510 0.059 Uiso 1 1 calc R . . H13B H 0.6900 0.0937 0.3557 0.059 Uiso 1 1 calc R . . C11 C 0.6257(4) 0.3912(5) 0.5158(3) 0.0623(13) Uani 1 1 d . . . H11A H 0.6253 0.4259 0.5681 0.093 Uiso 1 1 calc R . . H11B H 0.5504 0.3727 0.4938 0.093 Uiso 1 1 calc R . . H11C H 0.6582 0.4535 0.4831 0.093 Uiso 1 1 calc R . . C6 C 0.0871(3) 0.2483(4) 0.3492(2) 0.0410(9) Uani 1 1 d . . . C17 C 0.4464(4) 0.1096(5) 0.4202(3) 0.0652(14) Uani 1 1 d . . . H17A H 0.3668 0.1104 0.4214 0.098 Uiso 1 1 calc R . . H17B H 0.4829 0.1253 0.4724 0.098 Uiso 1 1 calc R . . H17C H 0.4690 0.0264 0.4019 0.098 Uiso 1 1 calc R . . C16 C 0.6474(4) 0.4273(6) 0.2537(3) 0.0655(14) Uani 1 1 d . . . H16A H 0.6099 0.4935 0.2209 0.098 Uiso 1 1 calc R . . H16B H 0.6866 0.3702 0.2217 0.098 Uiso 1 1 calc R . . H16C H 0.6997 0.4671 0.2932 0.098 Uiso 1 1 calc R . . O4 O 0.2363(3) 0.5910(3) 0.28600(18) 0.0491(7) Uani 1 1 d . . . O3 O 0.1810(3) 0.4025(3) 0.23707(18) 0.0538(8) Uani 1 1 d U . . C19 C 0.1704(4) 0.4950(3) 0.2825(3) 0.0395(9) Uani 1 1 d U . . O2W O 0.685(2) 0.684(2) 0.4666(16) 0.112(9) Uani 0.20 1 d P . . O1W O 0.554(3) 0.818(2) 0.3421(14) 0.114(7) Uani 0.40 1 d P . . O3W O 0.524(3) 0.760(3) 0.3444(18) 0.087(8) Uani 0.25 1 d PU . . O4W O 0.597(4) 0.774(6) 0.333(3) 0.111(19) Uani 0.15 1 d PU . . 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 Cd1 0.0422(2) 0.03341(19) 0.0312(2) 0.00091(10) -0.00016(14) 0.00007(10) C5 0.042(2) 0.037(2) 0.037(2) -0.0050(14) 0.0052(18) -0.0009(14) C4 0.039(2) 0.0361(19) 0.042(2) -0.0047(16) 0.0027(16) -0.0003(15) C3 0.054(2) 0.035(2) 0.057(3) -0.0003(18) 0.011(2) 0.0011(17) C2 0.058(3) 0.053(3) 0.072(4) -0.010(2) 0.019(2) 0.010(2) C10 0.044(2) 0.0385(19) 0.040(2) 0.0044(17) -0.0023(16) 0.0036(15) C1 0.047(2) 0.050(2) 0.061(3) 0.001(2) 0.010(2) -0.0062(18) O2 0.0443(16) 0.0446(15) 0.062(2) 0.0002(14) 0.0042(14) 0.0015(12) C15 0.046(2) 0.045(2) 0.039(2) 0.0104(17) -0.0082(17) -0.0033(17) N4 0.0534(19) 0.0379(16) 0.0330(18) -0.0012(14) 0.0032(14) 0.0063(14) O1 0.0517(18) 0.0404(16) 0.089(3) -0.0164(16) -0.0008(16) -0.0026(13) C7 0.051(3) 0.061(3) 0.082(4) -0.008(2) 0.026(3) 0.0010(19) C12 0.0355(18) 0.0393(19) 0.037(2) 0.0055(16) -0.0010(15) 0.0003(14) C9 0.043(2) 0.0398(19) 0.033(2) 0.0043(15) -0.0016(16) -0.0021(15) C8 0.068(3) 0.056(2) 0.039(3) 0.005(2) 0.004(2) 0.015(2) N3 0.0417(17) 0.0380(16) 0.0407(19) 0.0102(14) -0.0024(14) -0.0028(13) C14 0.041(2) 0.051(2) 0.0273(19) 0.0070(17) -0.0059(15) 0.0003(16) N1 0.0469(18) 0.0360(16) 0.0354(18) 0.0005(13) 0.0003(14) 0.0056(13) N2 0.0406(18) 0.0466(18) 0.046(2) 0.0100(15) -0.0053(15) -0.0075(14) C18 0.039(2) 0.048(2) 0.036(2) 0.0052(17) -0.0016(16) -0.0039(16) C13 0.051(2) 0.059(3) 0.036(2) 0.0079(19) -0.0048(18) 0.0063(19) C11 0.073(3) 0.049(2) 0.063(3) 0.002(2) 0.000(2) 0.021(2) C6 0.048(2) 0.0327(18) 0.043(2) -0.0022(16) 0.0078(17) -0.0033(15) C17 0.058(3) 0.066(3) 0.068(3) 0.033(3) -0.009(2) -0.013(2) C16 0.050(3) 0.082(4) 0.065(3) 0.032(3) 0.008(2) 0.007(2) O4 0.0587(18) 0.0393(15) 0.0513(19) -0.0066(13) 0.0152(14) -0.0056(13) O3 0.069(2) 0.0454(16) 0.0506(19) -0.0124(14) 0.0205(15) -0.0074(14) C19 0.049(2) 0.0343(19) 0.035(2) -0.0001(14) 0.0022(18) 0.0023(14) O2W 0.114(19) 0.080(15) 0.13(2) -0.049(15) -0.023(15) 0.030(13) O1W 0.141(18) 0.103(14) 0.087(11) -0.014(11) -0.037(11) 0.021(14) O3W 0.088(11) 0.091(11) 0.081(11) 0.002(9) 0.009(8) 0.010(8) O4W 0.11(2) 0.11(2) 0.11(2) -0.004(10) 0.012(10) -0.002(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 Cd1 O1 2.260(3) 2 ? Cd1 N1 2.268(3) 4_565 ? Cd1 N3 2.275(3) . ? Cd1 O4 2.331(3) . ? Cd1 O3 2.445(3) . ? Cd1 O2 2.518(3) 2 ? Cd1 C6 2.733(4) 2 ? Cd1 C19 2.737(5) . ? C5 C3 1.392(5) . ? C5 C4 1.397(5) . ? C5 C19 1.498(6) . ? C4 C1 1.404(6) . ? C4 C6 1.502(5) . ? C3 C2 1.382(6) . ? C2 C7 1.359(7) . ? C10 N4 1.341(5) . ? C10 C12 1.382(6) . ? C10 C11 1.504(5) . ? C1 C7 1.369(6) . ? O2 C6 1.249(5) . ? O2 Cd1 2.518(3) 2_545 ? C15 N2 1.337(5) . ? C15 C14 1.377(6) . ? C15 C17 1.487(6) . ? N4 N1 1.351(4) . ? O1 C6 1.262(5) . ? O1 Cd1 2.260(3) 2_545 ? C12 C9 1.414(5) . ? C12 C13 1.503(6) . ? C9 N1 1.334(5) . ? C9 C8 1.498(6) . ? N3 C18 1.335(5) . ? N3 N2 1.358(4) . ? C14 C18 1.402(6) . ? C14 C13 1.512(5) . ? N1 Cd1 2.268(3) 4_666 ? C18 C16 1.496(6) . ? C6 Cd1 2.733(4) 2_545 ? O4 C19 1.264(5) . ? O3 C19 1.242(5) . ? O1W O3W 0.69(3) . ? O1W O4W 0.71(5) . ? O3W O4W 0.93(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cd1 N1 114.63(13) 2 4_565 ? O1 Cd1 N3 96.36(11) 2 . ? N1 Cd1 N3 107.32(12) 4_565 . ? O1 Cd1 O4 104.86(12) 2 . ? N1 Cd1 O4 130.68(11) 4_565 . ? N3 Cd1 O4 95.97(12) . . ? O1 Cd1 O3 159.17(12) 2 . ? N1 Cd1 O3 82.84(11) 4_565 . ? N3 Cd1 O3 88.48(11) . . ? O4 Cd1 O3 54.40(10) . . ? O1 Cd1 O2 54.24(10) 2 2 ? N1 Cd1 O2 96.39(11) 4_565 2 ? N3 Cd1 O2 148.59(11) . 2 ? O4 Cd1 O2 83.21(10) . 2 ? O3 Cd1 O2 115.21(10) . 2 ? O1 Cd1 C6 27.24(11) 2 2 ? N1 Cd1 C6 108.97(12) 4_565 2 ? N3 Cd1 C6 122.38(12) . 2 ? O4 Cd1 C6 92.74(11) . 2 ? O3 Cd1 C6 138.85(11) . 2 ? O2 Cd1 C6 27.12(10) 2 2 ? O1 Cd1 C19 132.26(12) 2 . ? N1 Cd1 C19 107.23(12) 4_565 . ? N3 Cd1 C19 92.08(12) . . ? O4 Cd1 C19 27.42(10) . . ? O3 Cd1 C19 26.99(10) . . ? O2 Cd1 C19 100.40(10) 2 . ? C6 Cd1 C19 117.13(11) 2 . ? C3 C5 C4 118.6(4) . . ? C3 C5 C19 119.7(3) . . ? C4 C5 C19 121.5(3) . . ? C5 C4 C1 119.5(4) . . ? C5 C4 C6 122.9(4) . . ? C1 C4 C6 117.6(4) . . ? C2 C3 C5 120.7(4) . . ? C7 C2 C3 120.4(5) . . ? N4 C10 C12 106.8(3) . . ? N4 C10 C11 119.8(4) . . ? C12 C10 C11 133.4(4) . . ? C7 C1 C4 120.2(4) . . ? C6 O2 Cd1 86.1(2) . 2_545 ? N2 C15 C14 106.5(4) . . ? N2 C15 C17 123.8(4) . . ? C14 C15 C17 129.7(4) . . ? C10 N4 N1 112.5(3) . . ? C6 O1 Cd1 97.7(3) . 2_545 ? C2 C7 C1 120.6(5) . . ? C10 C12 C9 104.8(3) . . ? C10 C12 C13 130.1(3) . . ? C9 C12 C13 125.1(4) . . ? N1 C9 C12 110.6(4) . . ? N1 C9 C8 122.2(3) . . ? C12 C9 C8 127.2(4) . . ? C18 N3 N2 104.6(3) . . ? C18 N3 Cd1 135.2(3) . . ? N2 N3 Cd1 119.6(2) . . ? C18 C14 C15 105.4(3) . . ? C18 C14 C13 128.1(4) . . ? C15 C14 C13 126.6(4) . . ? C9 N1 N4 105.2(3) . . ? C9 N1 Cd1 134.0(3) . 4_666 ? N4 N1 Cd1 118.0(2) . 4_666 ? C15 N2 N3 112.7(3) . . ? N3 C18 C14 110.8(3) . . ? N3 C18 C16 121.1(4) . . ? C14 C18 C16 128.1(4) . . ? C14 C13 C12 115.0(4) . . ? O2 C6 O1 121.4(4) . . ? O2 C6 C4 121.4(3) . . ? O1 C6 C4 117.1(4) . . ? O2 C6 Cd1 66.8(2) . 2_545 ? O1 C6 Cd1 55.0(2) . 2_545 ? C4 C6 Cd1 171.1(3) . 2_545 ? C19 O4 Cd1 94.5(3) . . ? C19 O3 Cd1 89.7(3) . . ? O3 C19 O4 121.4(5) . . ? O3 C19 C5 119.6(4) . . ? O4 C19 C5 119.1(4) . . ? O3 C19 Cd1 63.3(3) . . ? O4 C19 Cd1 58.1(2) . . ? C5 C19 Cd1 177.1(3) . . ? O3W O1W O4W 83(6) . . ? O1W O3W O4W 50(4) . . ? O1W O4W O3W 48(4) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.671 _refine_diff_density_min -0.801 _refine_diff_density_rms 0.102 _database_code_depnum_ccdc_archive 'CCDC 877568' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H20.20 Cd N4 O4.10' _chemical_formula_weight 482.59 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8799(16) _cell_length_b 10.0359(15) _cell_length_c 12.070(2) _cell_angle_alpha 103.223(4) _cell_angle_beta 109.450(5) _cell_angle_gamma 96.942(6) _cell_volume 1073.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2308 _cell_measurement_theta_min 2.1342 _cell_measurement_theta_max 27.4680 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 486 _exptl_absorpt_coefficient_mu 1.048 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7946 _exptl_absorpt_correction_T_max 0.8338 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SCXmini CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6994 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0722 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3724 _reflns_number_gt 3115 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.1247P)^2^+1.8502P] 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 SHELXL _refine_ls_extinction_coef 0.064(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3724 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0712 _refine_ls_wR_factor_ref 0.2166 _refine_ls_wR_factor_gt 0.1873 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.42531(6) 0.02040(6) 0.33564(5) 0.0511(3) Uani 1 1 d . . . O4 O 0.3733(7) 0.8742(6) 0.4343(6) 0.0573(15) Uani 1 1 d . . . O3 O 0.3993(7) 0.2384(6) 0.3451(6) 0.0601(15) Uani 1 1 d . . . N4 N 0.2536(9) -0.0613(8) 0.1307(7) 0.0575(18) Uani 1 1 d . . . O2 O 0.3761(9) 0.7127(7) 0.2768(6) 0.0755(19) Uani 1 1 d . . . N3 N 0.2097(9) -0.2032(8) 0.0788(7) 0.0618(19) Uani 1 1 d . . . H3D H 0.2281 -0.2624 0.1205 0.074 Uiso 1 1 calc R . . O1 O 0.2864(8) 0.1673(6) 0.4578(6) 0.0671(17) Uani 1 1 d . . . N2 N 0.3707(7) -0.0027(7) -0.2929(6) 0.0528(16) Uani 1 1 d . . . C19 C 0.3533(9) 0.7464(8) 0.3738(8) 0.0518(19) Uani 1 1 d . . . C18 C 0.3294(8) 0.5016(8) 0.3922(7) 0.0445(17) Uani 1 1 d . . . H18A H 0.3768 0.4805 0.3376 0.053 Uiso 1 1 calc R . . N1 N 0.2729(8) 0.0730(7) -0.3400(6) 0.0574(18) Uani 1 1 d . . . H1D H 0.2865 0.1291 -0.3814 0.069 Uiso 1 1 calc R . . C17 C 0.1364(11) -0.2412(10) -0.0413(8) 0.062(2) Uani 1 1 d . . . C16 C 0.2881(8) 0.3989(8) 0.4423(7) 0.0449(17) Uani 1 1 d . . . C15 C 0.1698(9) -0.0430(9) -0.2460(8) 0.0525(19) Uani 1 1 d . . . C14 C 0.2006(9) -0.0109(9) 0.0352(8) 0.055(2) Uani 1 1 d . . . C13 C 0.1547(10) 0.0493(9) -0.3142(8) 0.058(2) Uani 1 1 d . . . C12 C 0.3255(9) 0.2602(8) 0.4133(7) 0.0505(19) Uani 1 1 d . . . C11 C 0.3011(9) 0.6355(8) 0.4222(7) 0.0470(17) Uani 1 1 d . . . C10 C 0.2123(11) 0.4309(9) 0.5203(9) 0.062(2) Uani 1 1 d . . . H10A H 0.1829 0.3638 0.5542 0.074 Uiso 1 1 calc R . . C9 C 0.0594(10) -0.1036(11) -0.1990(8) 0.061(2) Uani 1 1 d . . . H9A H -0.0098 -0.0430 -0.1976 0.074 Uiso 1 1 calc R . . H9B H 0.0046 -0.1944 -0.2557 0.074 Uiso 1 1 calc R . . C8 C 0.0314(12) 0.1291(13) -0.3521(12) 0.086(3) Uani 1 1 d . . . H8A H 0.0531 0.1862 -0.4004 0.129 Uiso 1 1 calc R . . H8B H 0.0246 0.1877 -0.2799 0.129 Uiso 1 1 calc R . . H8C H -0.0603 0.0634 -0.3994 0.129 Uiso 1 1 calc R . . C7 C 0.2263(9) 0.6653(9) 0.5011(8) 0.056(2) Uani 1 1 d . . . H7A H 0.2076 0.7543 0.5222 0.068 Uiso 1 1 calc R . . C6 C 0.3086(9) -0.0712(9) -0.2330(7) 0.0506(19) Uani 1 1 d . . . C5 C 0.1802(11) 0.5644(9) 0.5479(9) 0.067(3) Uani 1 1 d . . . H5A H 0.1272 0.5843 0.5982 0.081 Uiso 1 1 calc R . . C4 C 0.1273(9) -0.1204(10) -0.0737(8) 0.059(2) Uani 1 1 d . . . C3 C 0.3896(11) -0.1652(11) -0.1680(9) 0.070(3) Uani 1 1 d . . . H3A H 0.4830 -0.1614 -0.1766 0.105 Uiso 1 1 calc R . . H3B H 0.3331 -0.2597 -0.2032 0.105 Uiso 1 1 calc R . . H3C H 0.4046 -0.1347 -0.0826 0.105 Uiso 1 1 calc R . . C2 C 0.2182(11) 0.1423(10) 0.0480(9) 0.063(2) Uani 1 1 d . . . H2A H 0.2851 0.1941 0.1293 0.094 Uiso 1 1 calc R . . H2B H 0.1245 0.1675 0.0337 0.094 Uiso 1 1 calc R . . H2C H 0.2564 0.1639 -0.0108 0.094 Uiso 1 1 calc R . . C1 C 0.0770(15) -0.3930(12) -0.1117(11) 0.098(4) Uani 1 1 d . . . H1A H 0.1073 -0.4497 -0.0576 0.146 Uiso 1 1 calc R . . H1B H 0.1139 -0.4155 -0.1763 0.146 Uiso 1 1 calc R . . H1C H -0.0284 -0.4110 -0.1464 0.146 Uiso 1 1 calc R . . O1W O 0.552(8) 0.543(8) 0.161(7) 0.079(19) Uiso 0.10 1 d P . . H1WC H 0.4946 0.5848 0.1879 0.095 Uiso 0.10 1 d PR . . H1WD H 0.5152 0.5171 0.0835 0.095 Uiso 0.10 1 d PR . . 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 Cd1 0.0646(5) 0.0443(4) 0.0620(5) 0.0259(3) 0.0358(4) 0.0195(3) O4 0.073(4) 0.039(3) 0.077(4) 0.035(3) 0.036(3) 0.018(3) O3 0.074(4) 0.046(3) 0.076(4) 0.024(3) 0.038(3) 0.026(3) N4 0.070(5) 0.063(5) 0.055(4) 0.031(4) 0.031(4) 0.024(4) O2 0.121(6) 0.059(4) 0.073(4) 0.037(3) 0.055(4) 0.028(4) N3 0.083(5) 0.047(4) 0.064(5) 0.025(3) 0.033(4) 0.012(4) O1 0.094(5) 0.050(3) 0.079(4) 0.039(3) 0.042(4) 0.025(3) N2 0.055(4) 0.058(4) 0.063(4) 0.030(3) 0.032(3) 0.024(3) C19 0.053(5) 0.044(4) 0.067(5) 0.028(4) 0.023(4) 0.019(4) C18 0.048(4) 0.043(4) 0.044(4) 0.015(3) 0.019(3) 0.007(3) N1 0.070(5) 0.059(4) 0.064(4) 0.035(4) 0.036(4) 0.027(4) C17 0.071(6) 0.071(6) 0.048(5) 0.018(4) 0.029(4) 0.010(5) C16 0.045(4) 0.043(4) 0.049(4) 0.016(3) 0.019(3) 0.007(3) C15 0.047(4) 0.060(5) 0.052(5) 0.023(4) 0.017(4) 0.007(4) C14 0.055(5) 0.068(5) 0.064(5) 0.036(5) 0.035(4) 0.018(4) C13 0.063(5) 0.064(5) 0.067(6) 0.032(4) 0.034(5) 0.031(4) C12 0.050(4) 0.039(4) 0.057(5) 0.021(4) 0.009(4) 0.010(3) C11 0.051(4) 0.040(4) 0.052(4) 0.018(3) 0.018(4) 0.013(3) C10 0.081(6) 0.054(5) 0.074(6) 0.035(4) 0.044(5) 0.022(5) C9 0.054(5) 0.086(7) 0.051(5) 0.033(5) 0.020(4) 0.014(5) C8 0.076(7) 0.097(8) 0.116(9) 0.068(7) 0.041(7) 0.048(6) C7 0.057(5) 0.044(4) 0.074(6) 0.018(4) 0.029(4) 0.017(4) C6 0.047(4) 0.061(5) 0.050(5) 0.020(4) 0.023(4) 0.014(4) C5 0.091(7) 0.046(5) 0.089(7) 0.022(4) 0.060(6) 0.013(5) C4 0.054(5) 0.078(6) 0.057(5) 0.029(5) 0.030(4) 0.014(4) C3 0.073(6) 0.082(7) 0.086(7) 0.053(6) 0.043(5) 0.034(5) C2 0.070(6) 0.064(5) 0.069(6) 0.032(5) 0.034(5) 0.015(5) C1 0.125(10) 0.077(7) 0.079(8) 0.010(6) 0.043(7) -0.009(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O4 2.204(5) 1_545 ? Cd1 O3 2.215(5) . ? Cd1 N2 2.257(6) 2_655 ? Cd1 N4 2.369(7) . ? Cd1 O4 2.694(6) 2_666 ? O4 C19 1.277(10) . ? O4 Cd1 2.204(5) 1_565 ? O3 C12 1.271(10) . ? N4 C14 1.336(10) . ? N4 N3 1.368(10) . ? O2 C19 1.244(10) . ? N3 C17 1.324(11) . ? O1 C12 1.259(10) . ? N2 C6 1.340(10) . ? N2 N1 1.358(9) . ? N2 Cd1 2.257(6) 2_655 ? C19 C11 1.485(11) . ? C18 C16 1.393(10) . ? C18 C11 1.397(10) . ? N1 C13 1.314(11) . ? C17 C4 1.360(13) . ? C17 C1 1.499(14) . ? C16 C10 1.393(11) . ? C16 C12 1.478(11) . ? C15 C13 1.363(11) . ? C15 C6 1.399(11) . ? C15 C9 1.514(11) . ? C14 C4 1.405(13) . ? C14 C2 1.492(12) . ? C13 C8 1.538(12) . ? C11 C7 1.391(11) . ? C10 C5 1.405(12) . ? C9 C4 1.495(12) . ? C7 C5 1.369(12) . ? C6 C3 1.500(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cd1 O3 132.3(2) 1_545 . ? O4 Cd1 N2 114.4(2) 1_545 2_655 ? O3 Cd1 N2 105.8(2) . 2_655 ? O4 Cd1 N4 107.6(2) 1_545 . ? O3 Cd1 N4 91.1(2) . . ? N2 Cd1 N4 97.1(2) 2_655 . ? O4 Cd1 O4 75.6(2) 1_545 2_666 ? O3 Cd1 O4 86.5(2) . 2_666 ? N2 Cd1 O4 81.6(2) 2_655 2_666 ? N4 Cd1 O4 176.83(19) . 2_666 ? C19 O4 Cd1 112.1(5) . 1_565 ? C12 O3 Cd1 103.1(5) . . ? C14 N4 N3 103.1(7) . . ? C14 N4 Cd1 138.3(6) . . ? N3 N4 Cd1 117.2(5) . . ? C17 N3 N4 113.8(7) . . ? C6 N2 N1 104.8(6) . . ? C6 N2 Cd1 130.8(5) . 2_655 ? N1 N2 Cd1 124.0(5) . 2_655 ? O2 C19 O4 122.2(7) . . ? O2 C19 C11 119.6(7) . . ? O4 C19 C11 118.2(7) . . ? C16 C18 C11 121.5(7) . . ? C13 N1 N2 111.2(7) . . ? N3 C17 C4 106.2(8) . . ? N3 C17 C1 120.6(9) . . ? C4 C17 C1 133.1(9) . . ? C10 C16 C18 118.4(7) . . ? C10 C16 C12 121.3(7) . . ? C18 C16 C12 120.3(7) . . ? C13 C15 C6 103.9(7) . . ? C13 C15 C9 127.7(8) . . ? C6 C15 C9 128.4(8) . . ? N4 C14 C4 110.8(8) . . ? N4 C14 C2 122.7(8) . . ? C4 C14 C2 126.5(8) . . ? N1 C13 C15 109.3(7) . . ? N1 C13 C8 120.8(8) . . ? C15 C13 C8 129.8(8) . . ? O1 C12 O3 121.4(7) . . ? O1 C12 C16 119.9(8) . . ? O3 C12 C16 118.6(7) . . ? C7 C11 C18 119.1(7) . . ? C7 C11 C19 120.0(7) . . ? C18 C11 C19 120.9(7) . . ? C16 C10 C5 120.2(8) . . ? C4 C9 C15 113.7(7) . . ? C5 C7 C11 120.4(8) . . ? N2 C6 C15 110.8(7) . . ? N2 C6 C3 118.8(7) . . ? C15 C6 C3 130.3(7) . . ? C7 C5 C10 120.4(8) . . ? C17 C4 C14 106.0(8) . . ? C17 C4 C9 128.2(9) . . ? C14 C4 C9 125.7(9) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.156 _refine_diff_density_min -1.163 _refine_diff_density_rms 0.345 _database_code_depnum_ccdc_archive 'CCDC 877569' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H23 Cd N4 O5.50' _chemical_formula_weight 507.79 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting TRICLINIC _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.17(2) _cell_length_b 11.31(2) _cell_length_c 11.92(3) _cell_angle_alpha 99.587(14) _cell_angle_beta 109.51(2) _cell_angle_gamma 107.60(3) _cell_volume 1060(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 669 _cell_measurement_theta_min 3.1249 _cell_measurement_theta_max 27.3986 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 1.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7911 _exptl_absorpt_correction_T_max 0.8561 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SCXmini CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9186 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_sigmaI/netI 0.0649 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 27.34 _reflns_number_total 4747 _reflns_number_gt 3805 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0640P)^2^+1.3995P] 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 4747 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1384 _refine_ls_wR_factor_gt 0.1246 _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 Cd1 Cd 0.70098(4) 0.17931(3) 0.24854(3) 0.04053(14) Uani 1 1 d . . . O2 O 0.4353(5) 0.0248(4) 0.1259(4) 0.0654(12) Uani 1 1 d . . . N4 N 0.6498(5) -0.1107(4) 0.1334(4) 0.0418(9) Uani 1 1 d . . . H4A H 0.5499 -0.1186 0.0887 0.050 Uiso 1 1 calc R . . N3 N 0.7672(5) -0.0012(4) 0.2258(4) 0.0414(9) Uani 1 1 d . . . N2 N 0.9875(5) -0.3523(4) 0.4988(4) 0.0399(9) Uani 1 1 d . . . H2A H 0.9416 -0.3969 0.5385 0.048 Uiso 1 1 calc R . . C12 C 1.0200(6) -0.2666(4) 0.3515(4) 0.0360(10) Uani 1 1 d . . . O1 O 0.4362(5) 0.2042(4) 0.2277(4) 0.0642(11) Uani 1 1 d . . . C11 C 0.7091(6) -0.2047(5) 0.1207(5) 0.0410(11) Uani 1 1 d . . . N1 N 1.1526(5) -0.2742(4) 0.5457(4) 0.0449(10) Uani 1 1 d . . . C10 C 0.9022(6) -0.0288(5) 0.2733(4) 0.0377(10) Uani 1 1 d . . . C9 C 0.8717(6) -0.1567(5) 0.2104(4) 0.0368(10) Uani 1 1 d . . . C8 C 0.1706(6) 0.0454(5) 0.0744(4) 0.0371(10) Uani 1 1 d . . . C7 C 0.0867(6) -0.0795(5) -0.0061(5) 0.0441(12) Uani 1 1 d . . . H7A H 0.1450 -0.1333 -0.0107 0.053 Uiso 1 1 calc R . . C6 C 0.9885(6) -0.2277(5) 0.2329(4) 0.0411(11) Uani 1 1 d . . . H6A H 1.0949 -0.1727 0.2361 0.049 Uiso 1 1 calc R . . H6B H 0.9419 -0.3052 0.1628 0.049 Uiso 1 1 calc R . . C5 C 0.9047(6) -0.3509(4) 0.3821(5) 0.0383(10) Uani 1 1 d . . . C4 C 1.1721(6) -0.2231(5) 0.4552(5) 0.0444(12) Uani 1 1 d . . . C3 C -0.0828(7) -0.1252(5) -0.0797(5) 0.0451(12) Uani 1 1 d . . . H3A H -0.1383 -0.2098 -0.1330 0.054 Uiso 1 1 calc R . . C2 C 0.3582(6) 0.0945(5) 0.1487(5) 0.0450(12) Uani 1 1 d . . . C1 C 1.0620(7) 0.0710(5) 0.3755(5) 0.0518(13) Uani 1 1 d . . . H1A H 1.0455 0.1495 0.4003 0.078 Uiso 1 1 calc R . . H1B H 1.1494 0.0888 0.3460 0.078 Uiso 1 1 calc R . . H1C H 1.0932 0.0385 0.4457 0.078 Uiso 1 1 calc R . . O4 O 0.7232(8) 0.2755(5) 0.1024(6) 0.0881(17) Uani 1 1 d . . . O3 O 0.9763(9) 0.3632(5) 0.2550(6) 0.0951(19) Uani 1 1 d . . . C13 C 0.6088(8) -0.3327(6) 0.0229(6) 0.0608(16) Uani 1 1 d . . . H13A H 0.4993 -0.3358 -0.0245 0.091 Uiso 1 1 calc R . . H13B H 0.5985 -0.4009 0.0617 0.091 Uiso 1 1 calc R . . H13C H 0.6639 -0.3439 -0.0314 0.091 Uiso 1 1 calc R . . C14 C 0.7212(7) -0.4299(7) 0.3129(6) 0.0655(17) Uani 1 1 d . . . H14A H 0.6817 -0.4776 0.3635 0.098 Uiso 1 1 calc R . . H14B H 0.7013 -0.4895 0.2368 0.098 Uiso 1 1 calc R . . H14C H 0.6627 -0.3734 0.2940 0.098 Uiso 1 1 calc R . . C17 C 0.9407(10) 0.4281(6) 0.0710(7) 0.0636(19) Uani 1 1 d . . . C15 C 1.3404(8) -0.1318(9) 0.4757(7) 0.085(2) Uani 1 1 d . . . H15A H 1.4200 -0.1205 0.5572 0.128 Uiso 1 1 calc R . . H15B H 1.3359 -0.0494 0.4692 0.128 Uiso 1 1 calc R . . H15C H 1.3741 -0.1666 0.4138 0.128 Uiso 1 1 calc R . . C18 C 1.1060(11) 0.5164(7) 0.1199(7) 0.075(2) Uani 1 1 d . . . H18A H 1.1778 0.5280 0.2010 0.090 Uiso 1 1 calc R . . C16 C 0.8787(13) 0.3523(8) 0.1500(8) 0.080(3) Uani 1 1 d . . . C19 C 0.8353(11) 0.4122(7) -0.0480(8) 0.075(2) Uani 1 1 d . . . H19A H 0.7244 0.3538 -0.0810 0.090 Uiso 1 1 calc R . . O1W O 0.3637(17) -0.6082(15) 0.3926(14) 0.130(5) Uani 0.55 1 d P . . O2W O 1.440(2) 0.3235(17) 0.4514(16) 0.134(5) Uani 0.50 1 d P . . O3W O 0.727(2) -0.4757(19) 0.5864(13) 0.138(7) Uani 0.45 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.0289(2) 0.0418(2) 0.0458(2) 0.02068(16) 0.00758(15) 0.01167(16) O2 0.0257(19) 0.066(3) 0.090(3) 0.019(2) 0.008(2) 0.0189(19) N4 0.028(2) 0.041(2) 0.047(2) 0.0161(18) 0.0032(17) 0.0111(18) N3 0.033(2) 0.040(2) 0.049(2) 0.0183(19) 0.0098(18) 0.0160(19) N2 0.035(2) 0.036(2) 0.039(2) 0.0160(17) 0.0097(17) 0.0046(18) C12 0.030(2) 0.035(2) 0.045(3) 0.016(2) 0.013(2) 0.014(2) O1 0.034(2) 0.066(3) 0.064(3) 0.007(2) 0.0028(18) 0.008(2) C11 0.034(3) 0.041(3) 0.044(3) 0.020(2) 0.009(2) 0.013(2) N1 0.035(2) 0.049(2) 0.045(2) 0.023(2) 0.0085(18) 0.013(2) C10 0.029(2) 0.042(3) 0.040(3) 0.019(2) 0.0095(19) 0.013(2) C9 0.037(3) 0.039(2) 0.036(2) 0.019(2) 0.012(2) 0.018(2) C8 0.026(2) 0.048(3) 0.036(2) 0.018(2) 0.0082(18) 0.015(2) C7 0.034(3) 0.046(3) 0.051(3) 0.013(2) 0.013(2) 0.019(2) C6 0.037(3) 0.053(3) 0.036(2) 0.015(2) 0.010(2) 0.024(2) C5 0.029(2) 0.033(2) 0.046(3) 0.012(2) 0.009(2) 0.009(2) C4 0.032(3) 0.053(3) 0.045(3) 0.022(2) 0.011(2) 0.013(2) C3 0.037(3) 0.046(3) 0.048(3) 0.012(2) 0.014(2) 0.015(2) C2 0.025(2) 0.055(3) 0.049(3) 0.027(3) 0.008(2) 0.011(2) C1 0.038(3) 0.048(3) 0.061(3) 0.013(3) 0.012(3) 0.015(3) O4 0.107(5) 0.090(4) 0.142(5) 0.085(4) 0.095(4) 0.060(4) O3 0.154(6) 0.078(3) 0.100(4) 0.054(3) 0.089(4) 0.050(4) C13 0.051(4) 0.048(3) 0.061(4) 0.013(3) 0.003(3) 0.014(3) C14 0.035(3) 0.075(4) 0.060(4) 0.022(3) 0.005(3) 0.004(3) C17 0.096(5) 0.054(3) 0.099(5) 0.051(3) 0.077(5) 0.050(4) C15 0.035(3) 0.122(6) 0.090(5) 0.068(5) 0.017(3) 0.009(4) C18 0.109(6) 0.075(5) 0.095(5) 0.056(4) 0.072(5) 0.058(5) C16 0.140(8) 0.076(5) 0.112(6) 0.071(5) 0.100(6) 0.080(6) C19 0.098(6) 0.061(4) 0.115(6) 0.053(4) 0.077(5) 0.041(4) O1W 0.073(8) 0.123(11) 0.138(12) -0.028(9) 0.027(8) 0.019(8) O2W 0.108(12) 0.123(12) 0.138(13) 0.023(10) 0.049(10) 0.011(10) O3W 0.100(12) 0.167(16) 0.082(10) 0.026(10) 0.012(8) -0.001(12) _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 Cd1 O4 2.235(6) . ? Cd1 N1 2.241(7) 2_756 ? Cd1 N3 2.299(5) . ? Cd1 O2 2.307(5) . ? Cd1 O1 2.464(7) . ? Cd1 O3 2.710(7) . ? Cd1 C2 2.742(8) . ? O2 C2 1.260(7) . ? N4 C11 1.342(7) . ? N4 N3 1.361(6) . ? N4 H4A 0.8600 . ? N3 C10 1.332(6) . ? N2 C5 1.350(7) . ? N2 N1 1.359(6) . ? N2 H2A 0.8600 . ? C12 C5 1.387(7) . ? C12 C4 1.395(7) . ? C12 C6 1.513(7) . ? O1 C2 1.250(7) . ? C11 C9 1.383(7) . ? C11 C13 1.489(8) . ? N1 C4 1.343(7) . ? N1 Cd1 2.241(7) 2_756 ? C10 C9 1.409(7) . ? C10 C1 1.502(7) . ? C9 C6 1.504(7) . ? C8 C7 1.381(7) . ? C8 C3 1.386(7) 2 ? C8 C2 1.514(7) . ? C7 C3 1.380(8) . ? C7 H7A 0.9300 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C5 C14 1.493(8) . ? C4 C15 1.486(8) . ? C3 C8 1.386(7) 2 ? C3 H3A 0.9300 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? O4 C16 1.286(11) . ? O3 C16 1.231(10) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C17 C19 1.368(11) . ? C17 C18 1.391(11) . ? C17 C16 1.509(9) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C18 C19 1.398(9) 2_765 ? C18 H18A 0.9300 . ? C19 C18 1.398(9) 2_765 ? C19 H19A 0.9300 . ? O1W O2W 1.32(2) 1_445 ? O1W O3W 1.48(2) 2_646 ? O2W O1W 1.32(2) 1_665 ? O3W O1W 1.48(2) 2_646 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cd1 N1 124.8(3) . 2_756 ? O4 Cd1 N3 111.38(19) . . ? N1 Cd1 N3 100.07(17) 2_756 . ? O4 Cd1 O2 95.6(3) . . ? N1 Cd1 O2 134.21(17) 2_756 . ? N3 Cd1 O2 81.3(2) . . ? O4 Cd1 O1 92.52(18) . . ? N1 Cd1 O1 99.01(17) 2_756 . ? N3 Cd1 O1 131.76(15) . . ? O2 Cd1 O1 54.24(19) . . ? O4 Cd1 O3 51.9(2) . . ? N1 Cd1 O3 78.8(2) 2_756 . ? N3 Cd1 O3 101.3(2) . . ? O2 Cd1 O3 146.4(2) . . ? O1 Cd1 O3 125.7(2) . . ? O4 Cd1 C2 93.1(2) . . ? N1 Cd1 C2 119.73(17) 2_756 . ? N3 Cd1 C2 107.39(19) . . ? O2 Cd1 C2 27.21(16) . . ? O1 Cd1 C2 27.11(17) . . ? O3 Cd1 C2 141.4(2) . . ? C2 O2 Cd1 96.0(4) . . ? C11 N4 N3 111.7(4) . . ? C11 N4 H4A 124.2 . . ? N3 N4 H4A 124.2 . . ? C10 N3 N4 105.6(4) . . ? C10 N3 Cd1 136.8(3) . . ? N4 N3 Cd1 117.2(3) . . ? C5 N2 N1 111.4(4) . . ? C5 N2 H2A 124.3 . . ? N1 N2 H2A 124.3 . . ? C5 C12 C4 105.0(5) . . ? C5 C12 C6 127.8(4) . . ? C4 C12 C6 127.1(5) . . ? C2 O1 Cd1 88.9(3) . . ? N4 C11 C9 107.1(4) . . ? N4 C11 C13 122.7(5) . . ? C9 C11 C13 130.1(5) . . ? C4 N1 N2 105.3(4) . . ? C4 N1 Cd1 126.4(4) . 2_756 ? N2 N1 Cd1 120.6(3) . 2_756 ? N3 C10 C9 110.5(4) . . ? N3 C10 C1 121.4(5) . . ? C9 C10 C1 128.1(5) . . ? C11 C9 C10 105.1(4) . . ? C11 C9 C6 126.5(5) . . ? C10 C9 C6 128.5(4) . . ? C7 C8 C3 119.2(5) . 2 ? C7 C8 C2 119.1(5) . . ? C3 C8 C2 121.6(5) 2 . ? C3 C7 C8 120.7(5) . . ? C3 C7 H7A 119.7 . . ? C8 C7 H7A 119.7 . . ? C9 C6 C12 114.2(4) . . ? C9 C6 H6A 108.7 . . ? C12 C6 H6A 108.7 . . ? C9 C6 H6B 108.7 . . ? C12 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? N2 C5 C12 107.2(4) . . ? N2 C5 C14 120.3(5) . . ? C12 C5 C14 132.5(5) . . ? N1 C4 C12 111.0(5) . . ? N1 C4 C15 119.7(5) . . ? C12 C4 C15 129.3(5) . . ? C7 C3 C8 120.2(5) . 2 ? C7 C3 H3A 119.9 . . ? C8 C3 H3A 119.9 2 . ? O1 C2 O2 120.5(5) . . ? O1 C2 C8 120.7(5) . . ? O2 C2 C8 118.7(5) . . ? O1 C2 Cd1 64.0(3) . . ? O2 C2 Cd1 56.8(3) . . ? C8 C2 Cd1 171.2(4) . . ? C10 C1 H1A 109.5 . . ? C10 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C10 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C16 O4 Cd1 103.3(5) . . ? C16 O3 Cd1 82.4(5) . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C5 C14 H14A 109.5 . . ? C5 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C5 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C19 C17 C18 119.5(6) . . ? C19 C17 C16 120.7(8) . . ? C18 C17 C16 119.8(8) . . ? C4 C15 H15A 109.5 . . ? C4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C18 C19 120.4(8) . 2_765 ? C17 C18 H18A 119.8 . . ? C19 C18 H18A 119.8 2_765 . ? O3 C16 O4 122.3(7) . . ? O3 C16 C17 120.1(9) . . ? O4 C16 C17 117.5(8) . . ? C17 C19 C18 120.1(8) . 2_765 ? C17 C19 H19A 119.9 . . ? C18 C19 H19A 119.9 2_765 . ? O2W O1W O3W 138.8(17) 1_445 2_646 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Cd1 O2 C2 -85.8(4) . . . . ? N1 Cd1 O2 C2 67.7(4) 2_756 . . . ? N3 Cd1 O2 C2 163.4(4) . . . . ? O1 Cd1 O2 C2 3.3(3) . . . . ? O3 Cd1 O2 C2 -99.2(4) . . . . ? C11 N4 N3 C10 -1.1(6) . . . . ? C11 N4 N3 Cd1 173.3(3) . . . . ? O4 Cd1 N3 C10 95.4(5) . . . . ? N1 Cd1 N3 C10 -38.3(5) 2_756 . . . ? O2 Cd1 N3 C10 -171.9(5) . . . . ? O1 Cd1 N3 C10 -150.2(5) . . . . ? O3 Cd1 N3 C10 42.1(5) . . . . ? C2 Cd1 N3 C10 -164.0(5) . . . . ? O4 Cd1 N3 N4 -76.7(4) . . . . ? N1 Cd1 N3 N4 149.5(3) 2_756 . . . ? O2 Cd1 N3 N4 15.9(3) . . . . ? O1 Cd1 N3 N4 37.7(4) . . . . ? O3 Cd1 N3 N4 -130.0(4) . . . . ? C2 Cd1 N3 N4 23.8(4) . . . . ? O4 Cd1 O1 C2 91.8(4) . . . . ? N1 Cd1 O1 C2 -142.4(3) 2_756 . . . ? N3 Cd1 O1 C2 -30.1(4) . . . . ? O2 Cd1 O1 C2 -3.3(3) . . . . ? O3 Cd1 O1 C2 135.0(4) . . . . ? N3 N4 C11 C9 1.5(6) . . . . ? N3 N4 C11 C13 -177.5(5) . . . . ? C5 N2 N1 C4 0.0(6) . . . . ? C5 N2 N1 Cd1 151.3(3) . . . 2_756 ? N4 N3 C10 C9 0.3(5) . . . . ? Cd1 N3 C10 C9 -172.5(4) . . . . ? N4 N3 C10 C1 177.7(5) . . . . ? Cd1 N3 C10 C1 5.0(8) . . . . ? N4 C11 C9 C10 -1.2(5) . . . . ? C13 C11 C9 C10 177.6(6) . . . . ? N4 C11 C9 C6 179.5(5) . . . . ? C13 C11 C9 C6 -1.7(9) . . . . ? N3 C10 C9 C11 0.5(6) . . . . ? C1 C10 C9 C11 -176.7(5) . . . . ? N3 C10 C9 C6 179.9(5) . . . . ? C1 C10 C9 C6 2.6(9) . . . . ? C3 C8 C7 C3 -0.6(9) 2 . . . ? C2 C8 C7 C3 -176.8(5) . . . . ? C11 C9 C6 C12 -108.6(6) . . . . ? C10 C9 C6 C12 72.2(7) . . . . ? C5 C12 C6 C9 62.8(7) . . . . ? C4 C12 C6 C9 -115.9(6) . . . . ? N1 N2 C5 C12 -0.9(5) . . . . ? N1 N2 C5 C14 -179.9(5) . . . . ? C4 C12 C5 N2 1.3(5) . . . . ? C6 C12 C5 N2 -177.6(4) . . . . ? C4 C12 C5 C14 -179.9(6) . . . . ? C6 C12 C5 C14 1.2(9) . . . . ? N2 N1 C4 C12 0.9(6) . . . . ? Cd1 N1 C4 C12 -148.2(4) 2_756 . . . ? N2 N1 C4 C15 -179.9(6) . . . . ? Cd1 N1 C4 C15 31.1(8) 2_756 . . . ? C5 C12 C4 N1 -1.4(6) . . . . ? C6 C12 C4 N1 177.5(4) . . . . ? C5 C12 C4 C15 179.5(7) . . . . ? C6 C12 C4 C15 -1.6(10) . . . . ? C8 C7 C3 C8 0.6(9) . . . 2 ? Cd1 O1 C2 O2 5.7(5) . . . . ? Cd1 O1 C2 C8 -171.5(4) . . . . ? Cd1 O2 C2 O1 -6.1(6) . . . . ? Cd1 O2 C2 C8 171.2(4) . . . . ? C7 C8 C2 O1 -175.7(5) . . . . ? C3 C8 C2 O1 8.2(8) 2 . . . ? C7 C8 C2 O2 7.0(8) . . . . ? C3 C8 C2 O2 -169.1(5) 2 . . . ? C7 C8 C2 Cd1 64(3) . . . . ? C3 C8 C2 Cd1 -112(2) 2 . . . ? O4 Cd1 C2 O1 -89.6(4) . . . . ? N1 Cd1 C2 O1 44.0(4) 2_756 . . . ? N3 Cd1 C2 O1 156.9(3) . . . . ? O2 Cd1 C2 O1 174.2(6) . . . . ? O3 Cd1 C2 O1 -66.9(5) . . . . ? O4 Cd1 C2 O2 96.3(4) . . . . ? N1 Cd1 C2 O2 -130.2(3) 2_756 . . . ? N3 Cd1 C2 O2 -17.2(4) . . . . ? O1 Cd1 C2 O2 -174.2(6) . . . . ? O3 Cd1 C2 O2 118.9(4) . . . . ? O4 Cd1 C2 C8 34(3) . . . . ? N1 Cd1 C2 C8 168(2) 2_756 . . . ? N3 Cd1 C2 C8 -79(3) . . . . ? O2 Cd1 C2 C8 -62(2) . . . . ? O1 Cd1 C2 C8 124(3) . . . . ? O3 Cd1 C2 C8 57(3) . . . . ? N1 Cd1 O4 C16 33.4(5) 2_756 . . . ? N3 Cd1 O4 C16 -86.7(4) . . . . ? O2 Cd1 O4 C16 -169.5(4) . . . . ? O1 Cd1 O4 C16 136.2(4) . . . . ? O3 Cd1 O4 C16 1.1(4) . . . . ? C2 Cd1 O4 C16 163.3(4) . . . . ? O4 Cd1 O3 C16 -1.1(4) . . . . ? N1 Cd1 O3 C16 -154.6(4) 2_756 . . . ? N3 Cd1 O3 C16 107.3(4) . . . . ? O2 Cd1 O3 C16 15.9(5) . . . . ? O1 Cd1 O3 C16 -61.5(4) . . . . ? C2 Cd1 O3 C16 -30.4(5) . . . . ? C19 C17 C18 C19 -0.5(10) . . . 2_765 ? C16 C17 C18 C19 -179.7(5) . . . 2_765 ? Cd1 O3 C16 O4 1.8(6) . . . . ? Cd1 O3 C16 C17 -176.8(5) . . . . ? Cd1 O4 C16 O3 -2.3(7) . . . . ? Cd1 O4 C16 C17 176.4(4) . . . . ? C19 C17 C16 O3 176.8(6) . . . . ? C18 C17 C16 O3 -4.0(9) . . . . ? C19 C17 C16 O4 -1.8(9) . . . . ? C18 C17 C16 O4 177.4(5) . . . . ? C18 C17 C19 C18 0.5(10) . . . 2_765 ? C16 C17 C19 C18 179.7(5) . . . 2_765 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.34 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.850 _refine_diff_density_min -1.192 _refine_diff_density_rms 0.104 _database_code_depnum_ccdc_archive 'CCDC 877570' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H22 Co N4 O6' _chemical_formula_weight 461.34 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 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 12.3835(11) _cell_length_b 10.2910(6) _cell_length_c 16.6384(13) _cell_angle_alpha 90.00 _cell_angle_beta 99.875(4) _cell_angle_gamma 90.00 _cell_volume 2089.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5057 _cell_measurement_theta_min 2.2453 _cell_measurement_theta_max 27.4835 _exptl_crystal_description rod _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 956 _exptl_absorpt_coefficient_mu 0.865 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8461 _exptl_absorpt_correction_T_max 0.8740 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SCXmini CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15995 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 27.46 _reflns_number_total 4724 _reflns_number_gt 4191 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0803P)^2^+2.9262P] 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 SHELXL _refine_ls_extinction_coef 0.0101(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4724 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1681 _refine_ls_wR_factor_gt 0.1578 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 Co1 Co 0.33881(3) 0.98767(4) 0.19606(2) 0.02887(17) Uani 1 1 d . . . N4 N 0.7406(2) 0.7344(3) 0.59671(16) 0.0386(6) Uani 1 1 d . . . H4A H 0.7321 0.7690 0.6423 0.046 Uiso 1 1 calc R . . C3 C 0.4937(3) 0.7130(3) 0.3633(2) 0.0375(7) Uani 1 1 d . . . C14 C 0.0954(3) 0.9721(3) 0.3282(2) 0.0330(7) Uani 1 1 d . . . C10 C 0.7882(2) 0.6009(3) 0.51073(18) 0.0333(7) Uani 1 1 d . . . C9 C 0.7037(3) 0.7872(4) 0.5239(2) 0.0415(8) Uani 1 1 d . . . C8 C 0.8383(4) 0.4855(4) 0.4779(2) 0.0555(11) Uani 1 1 d . . . H8A H 0.8718 0.4314 0.5223 0.083 Uiso 1 1 calc R . . H8B H 0.8929 0.5135 0.4471 0.083 Uiso 1 1 calc R . . H8C H 0.7826 0.4372 0.4432 0.083 Uiso 1 1 calc R . . N2 N 0.4125(2) 0.7848(3) 0.32209(17) 0.0361(6) Uani 1 1 d . . . H2A H 0.3445 0.7740 0.3252 0.043 Uiso 1 1 calc R . . C17 C -0.0494(3) 1.0856(4) 0.3790(3) 0.0532(10) Uani 1 1 d . . . H17A H -0.0872 1.1621 0.3849 0.064 Uiso 1 1 calc R . . N1 N 0.4490(2) 0.8763(3) 0.27504(15) 0.0324(6) Uani 1 1 d . . . C13 C -0.0253(3) 0.8583(4) 0.4030(2) 0.0441(8) Uani 1 1 d . . . H13A H -0.0467 0.7820 0.4258 0.053 Uiso 1 1 calc R . . C12 C 0.0629(3) 0.8561(3) 0.36082(19) 0.0330(7) Uani 1 1 d . . . C2 C 0.5902(2) 0.7609(3) 0.34342(18) 0.0346(7) Uani 1 1 d . . . C16 C 0.0388(3) 1.0861(4) 0.3377(2) 0.0428(8) Uani 1 1 d . . . H16A H 0.0602 1.1633 0.3161 0.051 Uiso 1 1 calc R . . C1 C 0.5588(3) 0.8624(3) 0.28847(19) 0.0344(7) Uani 1 1 d . . . C7 C 0.7314(2) 0.7027(3) 0.46590(18) 0.0341(7) Uani 1 1 d . . . N3 N 0.7930(2) 0.6203(3) 0.59061(15) 0.0346(6) Uani 1 1 d . . . C15 C -0.0806(3) 0.9713(4) 0.4113(3) 0.0523(10) Uani 1 1 d . . . H15A H -0.1397 0.9709 0.4391 0.063 Uiso 1 1 calc R . . C5 C 0.6318(3) 0.9470(5) 0.2475(3) 0.0569(11) Uani 1 1 d . . . H5A H 0.5880 1.0094 0.2134 0.085 Uiso 1 1 calc R . . H5B H 0.6711 0.8942 0.2147 0.085 Uiso 1 1 calc R . . H5C H 0.6829 0.9917 0.2881 0.085 Uiso 1 1 calc R . . C6 C 0.7041(3) 0.7124(4) 0.3741(2) 0.0431(8) Uani 1 1 d . . . H6A H 0.7562 0.7703 0.3552 0.052 Uiso 1 1 calc R . . H6B H 0.7124 0.6272 0.3509 0.052 Uiso 1 1 calc R . . C4 C 0.4731(3) 0.6044(4) 0.4179(3) 0.0588(11) Uani 1 1 d . . . H4B H 0.3958 0.5974 0.4181 0.088 Uiso 1 1 calc R . . H4C H 0.5107 0.6213 0.4723 0.088 Uiso 1 1 calc R . . H4D H 0.4995 0.5245 0.3986 0.088 Uiso 1 1 calc R . . C11 C 0.6437(4) 0.9133(4) 0.5181(3) 0.0652(13) Uani 1 1 d . . . H11A H 0.6397 0.9442 0.5719 0.098 Uiso 1 1 calc R . . H11B H 0.5710 0.9012 0.4881 0.098 Uiso 1 1 calc R . . H11C H 0.6819 0.9757 0.4905 0.098 Uiso 1 1 calc R . . O4 O 0.20305(19) 0.8713(2) 0.24092(14) 0.0378(5) Uani 1 1 d . . . O3 O 0.0642(2) 0.6361(2) 0.32172(16) 0.0422(6) Uani 1 1 d . . . O2 O 0.2401(2) 1.0734(2) 0.27164(15) 0.0404(6) Uani 1 1 d . . . O1 O 0.21993(19) 0.7172(3) 0.38675(16) 0.0464(6) Uani 1 1 d . . . C19 C 0.1841(3) 0.9723(3) 0.27790(19) 0.0326(7) Uani 1 1 d . . . C18 C 0.1223(3) 0.7298(3) 0.35576(19) 0.0337(7) Uani 1 1 d . . . O1W O 0.2852(8) 0.8039(10) 0.5607(7) 0.280(6) Uani 1 1 d . . . H1WC H 0.2753 0.7744 0.5123 0.336 Uiso 1 1 d R . . H1WD H 0.3484 0.7808 0.5849 0.336 Uiso 1 1 d R . . O2WA O 0.4898(8) 0.7524(9) 0.6554(6) 0.189(4) Uiso 0.85 1 d P . . O2WB O 0.396(4) 0.688(4) 0.684(3) 0.142(14) Uiso 0.15 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0305(3) 0.0293(3) 0.0251(2) 0.00026(15) -0.00014(16) 0.00016(15) N4 0.0508(16) 0.0340(15) 0.0292(13) 0.0005(11) 0.0017(12) 0.0101(12) C3 0.0334(15) 0.0407(19) 0.0358(16) 0.0128(14) -0.0014(12) 0.0015(13) C14 0.0357(16) 0.0293(16) 0.0341(16) -0.0033(12) 0.0064(12) 0.0012(12) C10 0.0324(15) 0.0383(18) 0.0274(14) 0.0030(13) 0.0005(11) 0.0033(12) C9 0.0439(18) 0.040(2) 0.0387(18) 0.0063(15) 0.0029(14) 0.0071(14) C8 0.074(3) 0.059(3) 0.0346(19) 0.0066(17) 0.0125(19) 0.026(2) N2 0.0303(13) 0.0386(16) 0.0372(14) 0.0097(12) -0.0007(10) -0.0028(11) C17 0.053(2) 0.040(2) 0.073(3) -0.0049(19) 0.026(2) 0.0087(17) N1 0.0316(13) 0.0333(14) 0.0301(12) 0.0066(11) -0.0010(10) -0.0002(10) C13 0.0418(18) 0.039(2) 0.054(2) -0.0008(16) 0.0154(16) -0.0041(15) C12 0.0332(15) 0.0315(17) 0.0334(15) -0.0051(13) 0.0037(12) -0.0007(12) C2 0.0303(15) 0.0442(19) 0.0261(14) 0.0055(13) -0.0037(11) 0.0020(13) C16 0.049(2) 0.0311(18) 0.050(2) 0.0027(15) 0.0132(16) 0.0031(15) C1 0.0322(15) 0.0393(18) 0.0304(15) 0.0060(13) 0.0014(12) -0.0022(13) C7 0.0297(14) 0.0428(19) 0.0274(14) 0.0050(13) -0.0017(11) 0.0020(12) N3 0.0384(14) 0.0361(15) 0.0275(12) 0.0033(11) 0.0006(10) 0.0052(11) C15 0.046(2) 0.049(2) 0.069(3) -0.003(2) 0.030(2) 0.0036(17) C5 0.0365(19) 0.072(3) 0.063(2) 0.037(2) 0.0113(17) 0.0040(18) C6 0.0338(16) 0.065(2) 0.0291(15) 0.0114(16) 0.0010(12) 0.0093(16) C4 0.046(2) 0.061(3) 0.066(3) 0.034(2) 0.0010(18) -0.0021(18) C11 0.093(3) 0.054(3) 0.047(2) 0.010(2) 0.005(2) 0.032(2) O4 0.0410(12) 0.0369(13) 0.0367(12) -0.0064(10) 0.0101(10) 0.0000(10) O3 0.0427(13) 0.0304(13) 0.0534(15) -0.0052(11) 0.0078(11) -0.0018(10) O2 0.0465(13) 0.0322(13) 0.0453(13) -0.0006(10) 0.0161(11) -0.0024(10) O1 0.0334(12) 0.0533(16) 0.0521(15) 0.0133(12) 0.0061(11) 0.0029(11) C19 0.0358(16) 0.0310(17) 0.0294(15) 0.0017(12) 0.0015(12) 0.0016(12) C18 0.0351(15) 0.0342(17) 0.0325(15) 0.0042(13) 0.0076(12) -0.0002(12) O1W 0.221(9) 0.284(12) 0.310(12) -0.120(11) -0.027(9) 0.028(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O3 1.996(2) 2 ? Co1 N1 2.071(3) . ? Co1 N3 2.072(3) 4_575 ? Co1 O2 2.093(2) . ? Co1 O4 2.291(2) . ? N4 C9 1.335(4) . ? N4 N3 1.353(4) . ? C3 N2 1.339(4) . ? C3 C2 1.384(5) . ? C3 C4 1.490(5) . ? C14 C16 1.389(5) . ? C14 C12 1.398(5) . ? C14 C19 1.491(5) . ? C10 N3 1.335(4) . ? C10 C7 1.403(4) . ? C10 C8 1.486(5) . ? C9 C7 1.385(5) . ? C9 C11 1.489(5) . ? N2 N1 1.351(4) . ? C17 C15 1.376(6) . ? C17 C16 1.386(5) . ? N1 C1 1.346(4) . ? C13 C15 1.369(5) . ? C13 C12 1.396(5) . ? C12 C18 1.503(4) . ? C2 C1 1.399(4) . ? C2 C6 1.501(4) . ? C1 C5 1.501(5) . ? C7 C6 1.509(4) . ? N3 Co1 2.072(3) 4_676 ? O4 C19 1.250(4) . ? O3 C18 1.276(4) . ? O3 Co1 1.996(2) 2_545 ? O2 C19 1.265(4) . ? O1 C18 1.238(4) . ? O2WA O2WB 1.49(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 O3 Co1 N1 99.78(10) 2 . ? O3 Co1 N3 111.68(11) 2 4_575 ? N1 Co1 N3 107.19(11) . 4_575 ? O3 Co1 O2 101.22(10) 2 . ? N1 Co1 O2 103.96(10) . . ? N3 Co1 O2 129.15(10) 4_575 . ? O3 Co1 O4 160.39(10) 2 . ? N1 Co1 O4 86.83(9) . . ? N3 Co1 O4 83.44(9) 4_575 . ? O2 Co1 O4 59.18(9) . . ? C9 N4 N3 112.3(3) . . ? N2 C3 C2 106.5(3) . . ? N2 C3 C4 122.3(3) . . ? C2 C3 C4 131.2(3) . . ? C16 C14 C12 119.5(3) . . ? C16 C14 C19 119.8(3) . . ? C12 C14 C19 120.5(3) . . ? N3 C10 C7 110.5(3) . . ? N3 C10 C8 122.4(3) . . ? C7 C10 C8 127.1(3) . . ? N4 C9 C7 106.8(3) . . ? N4 C9 C11 120.1(3) . . ? C7 C9 C11 133.0(3) . . ? C3 N2 N1 112.6(3) . . ? C15 C17 C16 119.6(3) . . ? C1 N1 N2 105.0(2) . . ? C1 N1 Co1 134.5(2) . . ? N2 N1 Co1 120.25(19) . . ? C15 C13 C12 120.9(3) . . ? C14 C12 C13 118.9(3) . . ? C14 C12 C18 122.7(3) . . ? C13 C12 C18 118.3(3) . . ? C3 C2 C1 105.5(3) . . ? C3 C2 C6 126.8(3) . . ? C1 C2 C6 127.7(3) . . ? C17 C16 C14 120.6(3) . . ? N1 C1 C2 110.3(3) . . ? N1 C1 C5 122.2(3) . . ? C2 C1 C5 127.5(3) . . ? C9 C7 C10 105.1(3) . . ? C9 C7 C6 128.6(3) . . ? C10 C7 C6 126.3(3) . . ? C10 N3 N4 105.3(3) . . ? C10 N3 Co1 136.2(2) . 4_676 ? N4 N3 Co1 117.8(2) . 4_676 ? C13 C15 C17 120.5(3) . . ? C2 C6 C7 113.6(3) . . ? C19 O4 Co1 86.35(19) . . ? C18 O3 Co1 109.7(2) . 2_545 ? C19 O2 Co1 95.0(2) . . ? O4 C19 O2 119.4(3) . . ? O4 C19 C14 119.6(3) . . ? O2 C19 C14 121.0(3) . . ? O1 C18 O3 122.8(3) . . ? O1 C18 C12 121.3(3) . . ? O3 C18 C12 115.8(3) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.873 _refine_diff_density_min -0.598 _refine_diff_density_rms 0.087 _database_code_depnum_ccdc_archive 'CCDC 877571' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H20 Co N4 O4' _chemical_formula_weight 427.32 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 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 8.8940(11) _cell_length_b 14.231(2) _cell_length_c 15.1546(18) _cell_angle_alpha 90.00 _cell_angle_beta 98.410(9) _cell_angle_gamma 90.00 _cell_volume 1897.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1849 _cell_measurement_theta_min 2.3147 _cell_measurement_theta_max 27.4487 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 884 _exptl_absorpt_coefficient_mu 0.938 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8346 _exptl_absorpt_correction_T_max 0.8644 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SCXmini CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14576 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4349 _reflns_number_gt 3555 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0673P)^2^+1.1400P] 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 SHELXL _refine_ls_extinction_coef 0.0048(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4349 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1312 _refine_ls_wR_factor_gt 0.1215 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 Co1 Co 0.15989(4) 0.25151(2) 0.76987(2) 0.03488(14) Uani 1 1 d . . . N4 N 0.5132(2) 0.43982(14) 1.24219(13) 0.0362(5) Uani 1 1 d . . . H4A H 0.5896 0.4666 1.2736 0.043 Uiso 1 1 calc R . . C19 C 0.1490(2) 0.41539(17) 0.99588(15) 0.0324(5) Uani 1 1 d . . . N3 N 0.4937(2) 0.34572(15) 1.23580(14) 0.0370(5) Uani 1 1 d . . . N2 N 0.1093(2) 0.35200(15) 0.85797(14) 0.0387(5) Uani 1 1 d . . . N1 N 0.1867(2) 0.43425(15) 0.85714(14) 0.0382(5) Uani 1 1 d . . . H1A H 0.2162 0.4578 0.8103 0.046 Uiso 1 1 calc R . . O2 O 0.1511(2) 0.30166(14) 0.64911(12) 0.0505(5) Uani 1 1 d . . . O1 O 0.2779(3) 0.43253(17) 0.68498(13) 0.0640(7) Uani 1 1 d . . . C18 C 0.3626(3) 0.33283(18) 1.18114(16) 0.0351(5) Uani 1 1 d . . . C17 C 0.0869(3) 0.34047(18) 0.94302(16) 0.0364(5) Uani 1 1 d . . . O4 O -0.1702(2) 0.29533(17) 0.35276(13) 0.0584(6) Uani 1 1 d . . . C16 C 0.0433(3) 0.39383(18) 0.38443(16) 0.0370(5) Uani 1 1 d . . . C15 C 0.3978(3) 0.48652(17) 1.19310(15) 0.0347(5) Uani 1 1 d . . . C14 C 0.2078(3) 0.37929(19) 0.62925(16) 0.0388(6) Uani 1 1 d . . . C13 C 0.2788(3) 0.4731(2) 0.50147(17) 0.0423(6) Uani 1 1 d . . . H13A H 0.3566 0.5005 0.5408 0.051 Uiso 1 1 calc R . . C12 C 0.1857(3) 0.40572(17) 0.53256(16) 0.0340(5) Uani 1 1 d . . . C11 C 0.2118(3) 0.47435(17) 0.93797(15) 0.0340(5) Uani 1 1 d . . . C10 C 0.2981(3) 0.41958(17) 1.15239(14) 0.0316(5) Uani 1 1 d . . . C9 C 0.0692(3) 0.36545(18) 0.47331(15) 0.0354(5) Uani 1 1 d . . . H9A H 0.0082 0.3193 0.4932 0.042 Uiso 1 1 calc R . . C8 C -0.0871(3) 0.3546(2) 0.32097(18) 0.0456(6) Uani 1 1 d . . . C7 C 0.1381(3) 0.4605(2) 0.35458(18) 0.0470(7) Uani 1 1 d . . . H7A H 0.1222 0.4791 0.2951 0.056 Uiso 1 1 calc R . . C6 C 0.1483(3) 0.43421(19) 1.09345(15) 0.0366(5) Uani 1 1 d . . . H6A H 0.0732 0.3937 1.1143 0.044 Uiso 1 1 calc R . . H6B H 0.1162 0.4986 1.1002 0.044 Uiso 1 1 calc R . . C5 C 0.2566(3) 0.4996(2) 0.41307(19) 0.0490(7) Uani 1 1 d . . . H5A H 0.3208 0.5435 0.3926 0.059 Uiso 1 1 calc R . . O3 O -0.1119(3) 0.3801(2) 0.24342(16) 0.0908(10) Uani 1 1 d . . . C4 C 0.3947(4) 0.59154(19) 1.1912(2) 0.0523(7) Uani 1 1 d . . . H4B H 0.4838 0.6155 1.2276 0.078 Uiso 1 1 calc R . . H4C H 0.3057 0.6136 1.2137 0.078 Uiso 1 1 calc R . . H4D H 0.3927 0.6129 1.1309 0.078 Uiso 1 1 calc R . . C3 C 0.2921(3) 0.5667(2) 0.95223(19) 0.0469(6) Uani 1 1 d . . . H3A H 0.3213 0.5878 0.8970 0.070 Uiso 1 1 calc R . . H3B H 0.3810 0.5595 0.9959 0.070 Uiso 1 1 calc R . . H3C H 0.2253 0.6121 0.9729 0.070 Uiso 1 1 calc R . . C2 C 0.3017(4) 0.2369(2) 1.1584(3) 0.0567(8) Uani 1 1 d . . . H2A H 0.3706 0.1909 1.1875 0.085 Uiso 1 1 calc R . . H2B H 0.2910 0.2280 1.0950 0.085 Uiso 1 1 calc R . . H2C H 0.2044 0.2302 1.1779 0.085 Uiso 1 1 calc R . . C1 C 0.0039(4) 0.2542(2) 0.9677(2) 0.0510(7) Uani 1 1 d . . . H1B H -0.0234 0.2159 0.9157 0.076 Uiso 1 1 calc R . . H1C H -0.0864 0.2728 0.9910 0.076 Uiso 1 1 calc R . . H1D H 0.0686 0.2190 1.0121 0.076 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0414(2) 0.0345(2) 0.0246(2) -0.00182(12) -0.00902(14) -0.00084(13) N4 0.0391(11) 0.0337(11) 0.0327(10) -0.0032(8) -0.0050(8) 0.0000(8) C19 0.0272(11) 0.0389(13) 0.0290(11) 0.0007(9) -0.0033(9) 0.0063(9) N3 0.0403(11) 0.0348(11) 0.0327(11) 0.0024(9) -0.0060(8) -0.0005(9) N2 0.0460(12) 0.0357(11) 0.0324(11) -0.0012(9) -0.0016(9) 0.0004(9) N1 0.0488(12) 0.0368(11) 0.0275(10) 0.0003(8) 0.0006(8) -0.0020(9) O2 0.0737(13) 0.0430(11) 0.0304(9) 0.0040(8) -0.0068(9) -0.0124(10) O1 0.0822(15) 0.0746(15) 0.0311(10) -0.0062(10) -0.0051(10) -0.0417(12) C18 0.0339(12) 0.0374(13) 0.0321(12) 0.0039(10) -0.0017(9) -0.0011(10) C17 0.0370(12) 0.0361(13) 0.0340(13) 0.0014(10) -0.0022(9) 0.0038(10) O4 0.0594(13) 0.0686(15) 0.0410(11) 0.0066(10) -0.0135(9) -0.0244(11) C16 0.0375(12) 0.0417(14) 0.0297(12) 0.0008(10) -0.0024(9) -0.0003(10) C15 0.0409(13) 0.0368(13) 0.0251(11) -0.0024(9) 0.0010(9) 0.0045(10) C14 0.0418(13) 0.0435(14) 0.0280(12) -0.0018(10) -0.0057(10) -0.0035(11) C13 0.0407(13) 0.0478(15) 0.0362(13) -0.0021(12) -0.0015(10) -0.0107(11) C12 0.0378(12) 0.0350(12) 0.0273(11) -0.0010(10) -0.0011(9) -0.0007(10) C11 0.0360(12) 0.0363(13) 0.0274(11) 0.0001(10) -0.0025(9) 0.0037(9) C10 0.0313(11) 0.0388(13) 0.0243(11) 0.0014(9) 0.0033(8) 0.0033(9) C9 0.0387(12) 0.0369(13) 0.0284(12) 0.0027(10) -0.0021(9) -0.0033(10) C8 0.0484(15) 0.0492(16) 0.0348(14) 0.0005(12) -0.0092(11) -0.0025(12) C7 0.0499(15) 0.0594(18) 0.0311(13) 0.0079(12) 0.0040(11) -0.0029(13) C6 0.0318(12) 0.0487(15) 0.0284(12) -0.0007(10) 0.0010(9) 0.0051(10) C5 0.0483(15) 0.0542(17) 0.0448(15) 0.0082(13) 0.0076(12) -0.0117(13) O3 0.0943(19) 0.128(3) 0.0403(12) 0.0221(15) -0.0230(12) -0.0374(18) C4 0.0650(18) 0.0364(15) 0.0496(17) -0.0083(12) -0.0115(14) 0.0087(13) C3 0.0582(17) 0.0446(15) 0.0359(14) -0.0031(12) 0.0006(12) -0.0070(13) C2 0.0506(17) 0.0408(16) 0.071(2) 0.0113(14) -0.0150(15) -0.0100(12) C1 0.0579(18) 0.0482(17) 0.0451(16) 0.0025(12) 0.0019(14) -0.0100(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O4 1.9368(19) 4_666 ? Co1 O2 1.9552(18) . ? Co1 N3 2.035(2) 4_565 ? Co1 N2 2.051(2) . ? N4 C15 1.351(3) . ? N4 N3 1.352(3) . ? C19 C11 1.389(3) . ? C19 C17 1.398(3) . ? C19 C6 1.503(3) . ? N3 C18 1.341(3) . ? N3 Co1 2.035(2) 4_666 ? N2 C17 1.343(3) . ? N2 N1 1.359(3) . ? N1 C11 1.340(3) . ? O2 C14 1.269(3) . ? O1 C14 1.234(3) . ? C18 C10 1.404(3) . ? C18 C2 1.490(4) . ? C17 C1 1.508(4) . ? O4 C8 1.263(3) . ? O4 Co1 1.9368(19) 4_565 ? C16 C7 1.388(4) . ? C16 C9 1.393(3) . ? C16 C8 1.502(3) . ? C15 C10 1.384(3) . ? C15 C4 1.495(4) . ? C14 C12 1.498(3) . ? C13 C5 1.378(4) . ? C13 C12 1.393(4) . ? C12 C9 1.391(3) . ? C11 C3 1.496(4) . ? C10 C6 1.506(3) . ? C8 O3 1.219(3) . ? C7 C5 1.390(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 O4 Co1 O2 130.79(10) 4_666 . ? O4 Co1 N3 113.54(10) 4_666 4_565 ? O2 Co1 N3 94.74(8) . 4_565 ? O4 Co1 N2 92.43(9) 4_666 . ? O2 Co1 N2 111.86(9) . . ? N3 Co1 N2 114.77(9) 4_565 . ? C15 N4 N3 111.6(2) . . ? C11 C19 C17 105.1(2) . . ? C11 C19 C6 125.0(2) . . ? C17 C19 C6 129.9(2) . . ? C18 N3 N4 105.71(19) . . ? C18 N3 Co1 126.69(17) . 4_666 ? N4 N3 Co1 125.06(15) . 4_666 ? C17 N2 N1 105.1(2) . . ? C17 N2 Co1 128.11(18) . . ? N1 N2 Co1 115.78(16) . . ? C11 N1 N2 112.0(2) . . ? C14 O2 Co1 125.24(16) . . ? N3 C18 C10 110.5(2) . . ? N3 C18 C2 121.5(2) . . ? C10 C18 C2 128.0(2) . . ? N2 C17 C19 110.8(2) . . ? N2 C17 C1 119.0(2) . . ? C19 C17 C1 130.2(2) . . ? C8 O4 Co1 115.30(17) . 4_565 ? C7 C16 C9 119.4(2) . . ? C7 C16 C8 119.6(2) . . ? C9 C16 C8 121.0(2) . . ? N4 C15 C10 107.0(2) . . ? N4 C15 C4 120.9(2) . . ? C10 C15 C4 132.1(2) . . ? O1 C14 O2 123.4(2) . . ? O1 C14 C12 119.8(2) . . ? O2 C14 C12 116.8(2) . . ? C5 C13 C12 120.6(2) . . ? C9 C12 C13 119.2(2) . . ? C9 C12 C14 120.5(2) . . ? C13 C12 C14 120.3(2) . . ? N1 C11 C19 107.0(2) . . ? N1 C11 C3 121.2(2) . . ? C19 C11 C3 131.8(2) . . ? C15 C10 C18 105.1(2) . . ? C15 C10 C6 128.5(2) . . ? C18 C10 C6 126.3(2) . . ? C12 C9 C16 120.5(2) . . ? O3 C8 O4 122.2(3) . . ? O3 C8 C16 121.4(3) . . ? O4 C8 C16 116.4(2) . . ? C5 C7 C16 120.4(2) . . ? C19 C6 C10 115.37(19) . . ? C13 C5 C7 119.9(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O1 0.86 2.08 2.843(3) 146.9 . N4 H4A O1 0.86 1.90 2.715(3) 156.6 3_667 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.483 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 877572' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 Co N4 O6' _chemical_formula_weight 471.33 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 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 8.5843(6) _cell_length_b 16.1917(13) _cell_length_c 15.2083(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.796(5) _cell_angle_gamma 90.00 _cell_volume 2113.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5790 _cell_measurement_theta_min 2.3727 _cell_measurement_theta_max 27.4758 _exptl_crystal_description lamellar _exptl_crystal_colour purple _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 972 _exptl_absorpt_coefficient_mu 0.856 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8542 _exptl_absorpt_correction_T_max 0.9042 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SCXmini CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13339 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_unetI/netI 0.0289 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3675 _reflns_number_gt 3485 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0665P)^2^+1.7482P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0036(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3675 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1212 _refine_ls_wR_factor_gt 0.1167 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co -0.00798(4) 0.10525(2) 0.21626(2) 0.02755(16) Uani 1 1 d . . . O1 O 0.2126(3) 0.25706(14) 0.22873(13) 0.0485(6) Uani 1 1 d . . . N1 N -0.1786(2) 0.53334(14) 0.22719(15) 0.0345(5) Uani 1 1 d . . . H1A H -0.1265 0.5609 0.2660 0.041 Uiso 1 1 calc R . . O2 O -0.1309(3) 0.27547(13) 0.58878(13) 0.0437(5) Uani 1 1 d . . . N2 N -0.0143(3) 0.19415(14) 0.05227(14) 0.0320(5) Uani 1 1 d . . . H2A H 0.0458 0.1566 0.0316 0.038 Uiso 1 1 calc R . . N3 N -0.3368(2) 0.53518(14) 0.21883(15) 0.0321(5) Uani 1 1 d . . . O3 O -0.0218(2) 0.38333(13) 0.65652(13) 0.0420(5) Uani 1 1 d . . . N4 N -0.0893(3) 0.18828(14) 0.13004(14) 0.0313(5) Uani 1 1 d . . . O4 O 0.0732(2) 0.17217(12) 0.31292(13) 0.0408(5) Uani 1 1 d . . . O5 O 0.3301(3) 0.56270(13) 0.47579(14) 0.0476(6) Uani 1 1 d . . . O6 O 0.3821(2) 0.52232(12) 0.33891(13) 0.0426(5) Uani 1 1 d . . . C20 C 0.1459(3) 0.23967(17) 0.29750(17) 0.0318(6) Uani 1 1 d . . . C19 C -0.2338(3) 0.45049(16) 0.11733(17) 0.0299(6) Uani 1 1 d . . . C18 C -0.1704(3) 0.25901(16) 0.13864(17) 0.0304(6) Uani 1 1 d . . . C17 C 0.2299(3) 0.43518(16) 0.42546(16) 0.0291(5) Uani 1 1 d . . . C16 C 0.1423(3) 0.30306(16) 0.36943(16) 0.0275(5) Uani 1 1 d . . . C15 C 0.2296(3) 0.37510(16) 0.36060(17) 0.0295(5) Uani 1 1 d . . . H15A H 0.2885 0.3830 0.3104 0.035 Uiso 1 1 calc R . . C14 C 0.1427(3) 0.42266(17) 0.50133(17) 0.0295(5) Uani 1 1 d . . . H14A H 0.1437 0.4621 0.5458 0.035 Uiso 1 1 calc R . . C13 C -0.1470(3) 0.30939(16) 0.06448(17) 0.0297(6) Uani 1 1 d . . . C12 C 0.0530(3) 0.29233(16) 0.44455(16) 0.0288(5) Uani 1 1 d . . . H12A H -0.0081 0.2452 0.4505 0.035 Uiso 1 1 calc R . . C11 C -0.1140(3) 0.48324(17) 0.16738(18) 0.0330(6) Uani 1 1 d . . . C10 C -0.0358(3) 0.33923(17) 0.59234(17) 0.0320(6) Uani 1 1 d . . . C9 C -0.2206(4) 0.39066(17) 0.0423(2) 0.0421(7) Uani 1 1 d . . . H9A H -0.1605 0.4166 -0.0037 0.051 Uiso 1 1 calc R . . H9B H -0.3242 0.3804 0.0185 0.051 Uiso 1 1 calc R . . C8 C 0.3209(3) 0.51371(17) 0.41449(18) 0.0332(6) Uani 1 1 d . . . C7 C -0.0456(3) 0.26588(17) 0.01185(17) 0.0333(6) Uani 1 1 d . . . C6 C -0.2639(4) 0.27384(19) 0.2193(2) 0.0443(7) Uani 1 1 d . . . H6A H -0.2556 0.2268 0.2576 0.066 Uiso 1 1 calc R . . H6B H -0.3712 0.2822 0.2029 0.066 Uiso 1 1 calc R . . H6C H -0.2252 0.3220 0.2493 0.066 Uiso 1 1 calc R . . C5 C 0.0547(3) 0.35118(16) 0.51001(16) 0.0284(5) Uani 1 1 d . . . C4 C -0.3703(3) 0.48423(16) 0.15151(17) 0.0311(6) Uani 1 1 d . . . C3 C -0.5350(3) 0.4684(2) 0.1251(2) 0.0463(7) Uani 1 1 d . . . H3A H -0.6027 0.5010 0.1609 0.069 Uiso 1 1 calc R . . H3B H -0.5584 0.4109 0.1329 0.069 Uiso 1 1 calc R . . H3C H -0.5503 0.4831 0.0644 0.069 Uiso 1 1 calc R . . C2 C 0.0273(4) 0.2861(2) -0.0742(2) 0.0504(8) Uani 1 1 d . . . H2B H 0.0923 0.2411 -0.0921 0.076 Uiso 1 1 calc R . . H2C H 0.0892 0.3352 -0.0680 0.076 Uiso 1 1 calc R . . H2D H -0.0529 0.2951 -0.1178 0.076 Uiso 1 1 calc R . . C1 C 0.0580(3) 0.4697(2) 0.1648(2) 0.0527(8) Uani 1 1 d . . . H1B H 0.1081 0.5026 0.2094 0.079 Uiso 1 1 calc R . . H1C H 0.0960 0.4854 0.1081 0.079 Uiso 1 1 calc R . . H1D H 0.0804 0.4124 0.1752 0.079 Uiso 1 1 calc R . . H2E H -0.190(6) 0.281(3) 0.638(4) 0.108(17) Uiso 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 Co1 0.0332(2) 0.0216(2) 0.0281(2) -0.00120(13) 0.00841(15) -0.00005(12) O1 0.0569(13) 0.0506(13) 0.0384(11) -0.0123(10) 0.0233(10) -0.0080(10) N1 0.0290(11) 0.0329(13) 0.0415(13) -0.0044(10) -0.0004(9) -0.0023(9) O2 0.0545(12) 0.0425(12) 0.0346(10) -0.0072(9) 0.0209(9) -0.0209(10) N2 0.0368(11) 0.0288(12) 0.0306(11) -0.0025(9) 0.0077(9) 0.0097(9) N3 0.0287(11) 0.0287(12) 0.0389(12) -0.0057(10) 0.0036(9) 0.0024(9) O3 0.0465(11) 0.0497(13) 0.0301(10) -0.0135(9) 0.0101(8) -0.0106(9) N4 0.0344(11) 0.0282(12) 0.0314(11) 0.0005(9) 0.0058(9) 0.0038(9) O4 0.0589(13) 0.0289(11) 0.0348(10) -0.0055(8) 0.0049(9) -0.0086(9) O5 0.0634(14) 0.0341(12) 0.0457(12) -0.0081(10) 0.0164(10) -0.0241(10) O6 0.0550(12) 0.0357(11) 0.0374(11) 0.0007(9) 0.0143(9) -0.0159(9) C20 0.0354(13) 0.0289(14) 0.0314(13) -0.0033(11) 0.0063(11) 0.0004(11) C19 0.0345(13) 0.0237(13) 0.0317(13) 0.0013(11) 0.0037(10) 0.0086(10) C18 0.0316(13) 0.0279(14) 0.0318(13) -0.0022(11) 0.0036(10) 0.0037(10) C17 0.0310(12) 0.0256(14) 0.0307(13) 0.0034(11) 0.0042(10) -0.0053(10) C16 0.0330(13) 0.0254(13) 0.0241(12) -0.0013(10) 0.0043(10) -0.0026(10) C15 0.0315(12) 0.0311(14) 0.0261(13) 0.0009(11) 0.0076(10) -0.0033(11) C14 0.0335(13) 0.0260(13) 0.0292(13) -0.0037(11) 0.0042(10) -0.0044(10) C13 0.0334(13) 0.0264(14) 0.0294(13) -0.0037(10) 0.0018(10) 0.0068(10) C12 0.0292(12) 0.0279(14) 0.0293(13) 0.0001(11) 0.0042(10) -0.0064(10) C11 0.0306(13) 0.0290(14) 0.0397(14) 0.0039(12) 0.0060(11) 0.0056(10) C10 0.0336(13) 0.0333(15) 0.0293(13) -0.0007(11) 0.0057(10) -0.0058(11) C9 0.0598(19) 0.0343(17) 0.0322(15) -0.0001(12) 0.0008(13) 0.0206(13) C8 0.0348(13) 0.0263(14) 0.0386(15) 0.0047(12) 0.0070(11) -0.0067(11) C7 0.0385(14) 0.0298(15) 0.0318(14) -0.0002(11) 0.0039(11) 0.0051(11) C6 0.0516(17) 0.0366(17) 0.0451(17) 0.0012(13) 0.0156(14) 0.0098(13) C5 0.0286(12) 0.0298(14) 0.0269(12) 0.0001(11) 0.0058(10) -0.0041(10) C4 0.0338(13) 0.0251(14) 0.0345(14) -0.0014(11) 0.0013(11) 0.0025(10) C3 0.0326(14) 0.052(2) 0.0539(18) -0.0106(15) -0.0031(13) 0.0050(13) C2 0.065(2) 0.0455(19) 0.0407(17) 0.0062(14) 0.0175(15) 0.0100(15) C1 0.0307(15) 0.066(2) 0.062(2) 0.0034(17) 0.0046(14) 0.0117(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 Co1 O6 1.9233(19) 2_545 ? Co1 O4 1.9475(19) . ? Co1 N4 1.997(2) . ? Co1 N3 2.018(2) 2_445 ? O1 C20 1.232(3) . ? N1 C11 1.344(3) . ? N1 N3 1.363(3) . ? O2 C10 1.317(3) . ? N2 C7 1.340(4) . ? N2 N4 1.358(3) . ? N3 C4 1.343(3) . ? N3 Co1 2.018(2) 2_455 ? O3 C10 1.214(3) . ? N4 C18 1.348(3) . ? O4 C20 1.282(3) . ? O5 C8 1.226(3) . ? O6 C8 1.278(3) . ? O6 Co1 1.9233(19) 2 ? C20 C16 1.501(4) . ? C19 C11 1.378(4) . ? C19 C4 1.399(3) . ? C19 C9 1.503(4) . ? C18 C13 1.409(4) . ? C18 C6 1.495(4) . ? C17 C15 1.385(4) . ? C17 C14 1.399(3) . ? C17 C8 1.503(3) . ? C16 C15 1.394(4) . ? C16 C12 1.396(3) . ? C14 C5 1.389(4) . ? C13 C7 1.383(4) . ? C13 C9 1.497(4) . ? C12 C5 1.378(4) . ? C11 C1 1.493(4) . ? C10 C5 1.496(3) . ? C7 C2 1.495(4) . ? C4 C3 1.487(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 O6 Co1 O4 121.36(9) 2_545 . ? O6 Co1 N4 112.14(9) 2_545 . ? O4 Co1 N4 103.84(9) . . ? O6 Co1 N3 101.50(9) 2_545 2_445 ? O4 Co1 N3 100.10(9) . 2_445 ? N4 Co1 N3 118.20(9) . 2_445 ? C11 N1 N3 111.7(2) . . ? C7 N2 N4 111.5(2) . . ? C4 N3 N1 105.1(2) . . ? C4 N3 Co1 125.64(17) . 2_455 ? N1 N3 Co1 129.09(17) . 2_455 ? C18 N4 N2 106.1(2) . . ? C18 N4 Co1 133.22(18) . . ? N2 N4 Co1 116.96(16) . . ? C20 O4 Co1 120.43(17) . . ? C8 O6 Co1 135.14(18) . 2 ? O1 C20 O4 125.7(3) . . ? O1 C20 C16 118.5(2) . . ? O4 C20 C16 115.8(2) . . ? C11 C19 C4 105.5(2) . . ? C11 C19 C9 127.2(2) . . ? C4 C19 C9 127.3(3) . . ? N4 C18 C13 109.5(2) . . ? N4 C18 C6 120.0(2) . . ? C13 C18 C6 130.4(2) . . ? C15 C17 C14 119.3(2) . . ? C15 C17 C8 120.7(2) . . ? C14 C17 C8 119.9(2) . . ? C15 C16 C12 119.0(2) . . ? C15 C16 C20 119.0(2) . . ? C12 C16 C20 121.9(2) . . ? C16 C15 C17 121.0(2) . . ? C5 C14 C17 119.8(2) . . ? C7 C13 C18 105.5(2) . . ? C7 C13 C9 125.8(2) . . ? C18 C13 C9 128.7(2) . . ? C5 C12 C16 120.3(2) . . ? N1 C11 C19 107.1(2) . . ? N1 C11 C1 121.6(3) . . ? C19 C11 C1 131.3(3) . . ? O3 C10 O2 123.3(2) . . ? O3 C10 C5 123.4(2) . . ? O2 C10 C5 113.3(2) . . ? C19 C9 C13 115.6(2) . . ? O5 C8 O6 126.2(2) . . ? O5 C8 C17 119.4(2) . . ? O6 C8 C17 114.4(2) . . ? N2 C7 C13 107.5(2) . . ? N2 C7 C2 120.5(2) . . ? C13 C7 C2 132.0(3) . . ? C12 C5 C14 120.5(2) . . ? C12 C5 C10 121.0(2) . . ? C14 C5 C10 118.5(2) . . ? N3 C4 C19 110.6(2) . . ? N3 C4 C3 120.3(2) . . ? C19 C4 C3 129.1(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O3 0.86 1.95 2.797(3) 170.5 3_566 N2 H2A O5 0.86 1.86 2.689(3) 161.2 2_545 O2 H2E O1 0.92(5) 1.73(5) 2.586(3) 153(5) 4_566 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.504 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 877573'