# Electronic Supplementary Material (ESI) for CrystEngComm # 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_cdbteNO2bdc _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H13 Cd N7 O7, H2 O ' _chemical_formula_sum 'C14 H15 Cd N7 O8' _chemical_formula_weight 521.73 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 C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.682(3) _cell_length_b 10.4091(13) _cell_length_c 19.858(3) _cell_angle_alpha 90.00 _cell_angle_beta 118.104(3) _cell_angle_gamma 90.00 _cell_volume 3771.1(10) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 8409 _cell_measurement_theta_min 3.1335 _cell_measurement_theta_max 27.4932 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.838 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 1.219 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7503 _exptl_absorpt_correction_T_max 0.8878 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10605 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4281 _reflns_number_gt 3494 _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^)+(0.0509P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4281 _refine_ls_number_parameters 285 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0855 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.130489(13) 0.90254(2) 0.422558(13) 0.02372(10) Uani 1 1 d . . . O1 O 0.09762(14) 1.0696(2) 0.34138(14) 0.0315(6) Uani 1 1 d . . . O2 O 0.14781(16) 1.1740(2) 0.45204(15) 0.0390(6) Uani 1 1 d . . . O3 O 0.13984(14) 1.6646(2) 0.43678(14) 0.0350(6) Uani 1 1 d . . . O4 O 0.10727(15) 1.7540(2) 0.32488(14) 0.0344(6) Uani 1 1 d . . . O5 O 0.0692(3) 1.4791(3) 0.10674(18) 0.0812(13) Uani 1 1 d . . . O6 O 0.02305(17) 1.2929(3) 0.10272(16) 0.0506(8) Uani 1 1 d . . . O7 O 0.24780(15) 0.9351(3) 0.43810(16) 0.0320(6) Uani 1 1 d D . . O8 O 0.20460(17) 1.3270(3) 0.58126(18) 0.0492(8) Uani 1 1 d D . . N1 N 0.21499(15) 0.9702(3) 0.66602(16) 0.0279(6) Uani 1 1 d . . . N2 N 0.19507(19) 0.8462(3) 0.66872(18) 0.0385(8) Uani 1 1 d . . . N3 N 0.17334(17) 0.8994(3) 0.55070(16) 0.0292(7) Uani 1 1 d . . . N4 N 0.11044(16) 1.1148(3) 0.68833(16) 0.0275(6) Uani 1 1 d . . . N5 N 0.10356(17) 1.2036(3) 0.63571(18) 0.0364(7) Uani 1 1 d . . . N6 N -0.00670(16) 1.1233(3) 0.61012(18) 0.0305(7) Uani 1 1 d . . . N7 N 0.0534(2) 1.3907(3) 0.13657(19) 0.0391(8) Uani 1 1 d . . . C1 C 0.23964(19) 1.0566(4) 0.7313(2) 0.0341(8) Uani 1 1 d . . . H1A H 0.2551 1.1382 0.7187 0.041 Uiso 1 1 calc R . . H1B H 0.2823 1.0187 0.7748 0.041 Uiso 1 1 calc R . . C2 C 0.18062(19) 1.0821(4) 0.7537(2) 0.0325(8) Uani 1 1 d . . . H2A H 0.1743 1.0056 0.7788 0.039 Uiso 1 1 calc R . . H2B H 0.1961 1.1529 0.7905 0.039 Uiso 1 1 calc R . . C3 C 0.1705(2) 0.8083(4) 0.5977(2) 0.0389(9) Uani 1 1 d . . . H3A H 0.1524 0.7251 0.5810 0.047 Uiso 1 1 calc R . . C4 C 0.20115(19) 0.9986(4) 0.5961(2) 0.0306(8) Uani 1 1 d . . . H4A H 0.2100 1.0792 0.5806 0.037 Uiso 1 1 calc R . . C5 C 0.0321(2) 1.2054(4) 0.5898(2) 0.0408(9) Uani 1 1 d . . . H5A H 0.0100 1.2591 0.5468 0.049 Uiso 1 1 calc R . . C6 C 0.0450(2) 1.0696(3) 0.6725(2) 0.0299(8) Uani 1 1 d . . . H6A H 0.0365 1.0075 0.7018 0.036 Uiso 1 1 calc R . . C7 C 0.10805(17) 1.2946(3) 0.33668(19) 0.0239(7) Uani 1 1 d . . . C8 C 0.11942(18) 1.4144(3) 0.3712(2) 0.0249(7) Uani 1 1 d . . . H8A H 0.1344 1.4195 0.4237 0.030 Uiso 1 1 calc R . . C9 C 0.10912(17) 1.5276(3) 0.32948(19) 0.0241(7) Uani 1 1 d . . . C10 C 0.08773(18) 1.5203(3) 0.25195(19) 0.0260(7) Uani 1 1 d . . . H10A H 0.0814 1.5951 0.2230 0.031 Uiso 1 1 calc R . . C11 C 0.07597(19) 1.3999(3) 0.2184(2) 0.0265(7) Uani 1 1 d . . . C12 C 0.08530(18) 1.2882(3) 0.2586(2) 0.0276(7) Uani 1 1 d . . . H12A H 0.0764 1.2083 0.2338 0.033 Uiso 1 1 calc R . . C13 C 0.11874(18) 1.1714(3) 0.3811(2) 0.0275(8) Uani 1 1 d . . . C14 C 0.11921(18) 1.6572(3) 0.3662(2) 0.0247(7) Uani 1 1 d . . . H1W H 0.258(2) 1.008(2) 0.429(2) 0.036(11) Uiso 1 1 d D . . H2W H 0.280(3) 0.905(4) 0.475(3) 0.044(14) Uiso 1 1 d . . . H3W H 0.178(2) 1.317(4) 0.601(2) 0.053 Uiso 1 1 d D . . H4W H 0.189(2) 1.281(4) 0.5422(17) 0.053 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.02820(15) 0.01997(14) 0.02104(14) -0.00001(10) 0.01000(11) 0.00055(10) O1 0.0402(14) 0.0170(12) 0.0337(14) 0.0009(10) 0.0143(12) -0.0015(10) O2 0.0541(16) 0.0302(14) 0.0299(14) 0.0044(12) 0.0174(13) 0.0019(13) O3 0.0447(15) 0.0257(13) 0.0239(13) -0.0055(11) 0.0073(12) 0.0048(12) O4 0.0528(16) 0.0190(12) 0.0338(14) -0.0020(11) 0.0225(13) -0.0029(12) O5 0.162(4) 0.047(2) 0.0421(19) 0.0011(16) 0.054(2) -0.019(2) O6 0.0640(19) 0.0519(19) 0.0329(15) -0.0157(14) 0.0205(15) -0.0126(16) O7 0.0275(13) 0.0329(15) 0.0297(14) 0.0059(13) 0.0085(12) -0.0017(12) O8 0.063(2) 0.0473(18) 0.0486(19) -0.0069(15) 0.0360(17) -0.0181(16) N1 0.0275(14) 0.0342(17) 0.0212(14) -0.0024(13) 0.0109(12) 0.0007(13) N2 0.056(2) 0.0357(17) 0.0313(17) 0.0047(15) 0.0268(17) 0.0062(16) N3 0.0355(16) 0.0305(16) 0.0215(14) 0.0011(13) 0.0134(13) 0.0032(13) N4 0.0275(15) 0.0314(16) 0.0236(15) -0.0004(13) 0.0122(13) 0.0011(13) N5 0.0351(17) 0.0387(18) 0.0358(17) 0.0041(15) 0.0170(15) -0.0027(15) N6 0.0264(15) 0.0308(16) 0.0314(17) 0.0039(13) 0.0114(14) 0.0028(13) N7 0.054(2) 0.0338(18) 0.0294(17) -0.0025(15) 0.0193(16) 0.0024(16) C1 0.0268(17) 0.049(2) 0.0233(18) -0.0058(17) 0.0087(15) -0.0023(17) C2 0.0312(18) 0.042(2) 0.0228(17) -0.0063(16) 0.0115(15) -0.0012(17) C3 0.052(2) 0.030(2) 0.037(2) 0.0001(17) 0.023(2) -0.0011(18) C4 0.0341(18) 0.0306(18) 0.0274(18) 0.0002(16) 0.0147(16) 0.0017(16) C5 0.040(2) 0.043(2) 0.039(2) 0.0114(19) 0.0180(19) 0.0048(19) C6 0.0327(18) 0.0285(19) 0.0309(19) 0.0010(16) 0.0169(16) 0.0008(16) C7 0.0224(16) 0.0214(16) 0.0265(17) 0.0005(14) 0.0104(14) 0.0016(14) C8 0.0262(16) 0.0249(17) 0.0216(16) -0.0029(14) 0.0096(14) -0.0032(14) C9 0.0231(16) 0.0201(16) 0.0270(17) -0.0008(14) 0.0101(14) 0.0024(13) C10 0.0283(17) 0.0203(17) 0.0279(18) 0.0060(14) 0.0120(15) 0.0002(14) C11 0.0272(17) 0.0263(17) 0.0246(17) -0.0019(14) 0.0112(15) -0.0019(15) C12 0.0272(16) 0.0223(16) 0.0312(18) -0.0012(15) 0.0120(15) 0.0022(14) C13 0.0280(17) 0.0191(17) 0.036(2) 0.0033(15) 0.0153(16) 0.0018(14) C14 0.0235(16) 0.0194(16) 0.0320(19) -0.0028(15) 0.0137(15) -0.0007(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 Cd1 O1 2.248(2) . ? Cd1 N3 2.266(3) . ? Cd1 O7 2.322(3) . ? Cd1 N6 2.342(3) 5_576 ? Cd1 O4 2.346(2) 1_545 ? Cd1 O3 2.490(3) 1_545 ? O1 C13 1.269(4) . ? O2 C13 1.245(4) . ? O3 C14 1.260(4) . ? O3 Cd1 2.490(3) 1_565 ? O4 C14 1.249(4) . ? O4 Cd1 2.346(2) 1_565 ? O5 N7 1.219(4) . ? O6 N7 1.219(4) . ? O7 H1W 0.834(19) . ? O7 H2W 0.78(5) . ? O8 H3W 0.826(18) . ? O8 H4W 0.834(18) . ? N1 C4 1.313(4) . ? N1 N2 1.364(5) . ? N1 C1 1.458(4) . ? N2 C3 1.315(5) . ? N3 C4 1.312(5) . ? N3 C3 1.351(5) . ? N4 C6 1.323(5) . ? N4 N5 1.351(4) . ? N4 C2 1.460(4) . ? N5 C5 1.322(5) . ? N6 C6 1.321(5) . ? N6 C5 1.357(5) . ? N6 Cd1 2.342(3) 5_576 ? N7 C11 1.467(5) . ? C1 C2 1.507(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9400 . ? C4 H4A 0.9400 . ? C5 H5A 0.9400 . ? C6 H6A 0.9400 . ? C7 C12 1.393(5) . ? C7 C8 1.388(4) . ? C7 C13 1.512(5) . ? C8 C9 1.398(5) . ? C8 H8A 0.9400 . ? C9 C10 1.389(5) . ? C9 C14 1.501(5) . ? C10 C11 1.386(5) . ? C10 H10A 0.9400 . ? C11 C12 1.372(5) . ? C12 H12A 0.9400 . ? 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 N3 129.98(10) . . ? O1 Cd1 O7 85.78(10) . . ? N3 Cd1 O7 91.23(10) . . ? O1 Cd1 N6 88.19(10) . 5_576 ? N3 Cd1 N6 96.18(11) . 5_576 ? O7 Cd1 N6 172.41(10) . 5_576 ? O1 Cd1 O4 92.40(9) . 1_545 ? N3 Cd1 O4 137.58(9) . 1_545 ? O7 Cd1 O4 90.01(10) . 1_545 ? N6 Cd1 O4 85.64(10) 5_576 1_545 ? O1 Cd1 O3 146.31(8) . 1_545 ? N3 Cd1 O3 83.68(9) . 1_545 ? O7 Cd1 O3 96.30(10) . 1_545 ? N6 Cd1 O3 86.19(10) 5_576 1_545 ? O4 Cd1 O3 54.07(8) 1_545 1_545 ? O1 Cd1 C14 119.15(10) . 1_545 ? N3 Cd1 C14 110.87(10) . 1_545 ? O7 Cd1 C14 94.17(10) . 1_545 ? N6 Cd1 C14 84.75(10) 5_576 1_545 ? O4 Cd1 C14 26.86(9) 1_545 1_545 ? O3 Cd1 C14 27.22(9) 1_545 1_545 ? C13 O1 Cd1 107.5(2) . . ? C14 O3 Cd1 88.1(2) . 1_565 ? C14 O4 Cd1 95.0(2) . 1_565 ? Cd1 O7 H1W 118(3) . . ? Cd1 O7 H2W 115(3) . . ? H1W O7 H2W 112(4) . . ? H3W O8 H4W 109(3) . . ? C4 N1 N2 109.6(3) . . ? C4 N1 C1 127.7(3) . . ? N2 N1 C1 122.3(3) . . ? C3 N2 N1 102.3(3) . . ? C4 N3 C3 103.0(3) . . ? C4 N3 Cd1 125.0(2) . . ? C3 N3 Cd1 131.6(3) . . ? C6 N4 N5 109.7(3) . . ? C6 N4 C2 127.2(3) . . ? N5 N4 C2 123.0(3) . . ? C5 N5 N4 102.7(3) . . ? C6 N6 C5 102.4(3) . . ? C6 N6 Cd1 120.5(2) . 5_576 ? C5 N6 Cd1 135.4(2) . 5_576 ? O6 N7 O5 123.3(4) . . ? O6 N7 C11 118.5(3) . . ? O5 N7 C11 118.1(3) . . ? N1 C1 C2 112.2(3) . . ? N1 C1 H1A 109.2 . . ? C2 C1 H1A 109.2 . . ? N1 C1 H1B 109.2 . . ? C2 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? N4 C2 C1 112.5(3) . . ? N4 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? N4 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? N2 C3 N3 114.2(3) . . ? N2 C3 H3A 122.9 . . ? N3 C3 H3A 122.9 . . ? N3 C4 N1 110.9(3) . . ? N3 C4 H4A 124.6 . . ? N1 C4 H4A 124.6 . . ? N5 C5 N6 114.3(3) . . ? N5 C5 H5A 122.8 . . ? N6 C5 H5A 122.8 . . ? N6 C6 N4 110.9(3) . . ? N6 C6 H6A 124.5 . . ? N4 C6 H6A 124.5 . . ? C12 C7 C8 118.8(3) . . ? C12 C7 C13 119.2(3) . . ? C8 C7 C13 122.0(3) . . ? C7 C8 C9 121.5(3) . . ? C7 C8 H8A 119.3 . . ? C9 C8 H8A 119.3 . . ? C10 C9 C8 119.3(3) . . ? C10 C9 C14 119.1(3) . . ? C8 C9 C14 121.5(3) . . ? C11 C10 C9 118.3(3) . . ? C11 C10 H10A 120.8 . . ? C9 C10 H10A 120.8 . . ? C12 C11 C10 122.8(3) . . ? C12 C11 N7 118.3(3) . . ? C10 C11 N7 118.9(3) . . ? C11 C12 C7 119.3(3) . . ? C11 C12 H12A 120.4 . . ? C7 C12 H12A 120.4 . . ? O2 C13 O1 124.3(3) . . ? O2 C13 C7 120.1(3) . . ? O1 C13 C7 115.7(3) . . ? O4 C14 O3 122.7(3) . . ? O4 C14 C9 117.8(3) . . ? O3 C14 C9 119.5(3) . . ? O4 C14 Cd1 58.10(17) . 1_565 ? O3 C14 Cd1 64.68(18) . 1_565 ? C9 C14 Cd1 175.5(2) . 1_565 ? 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 N3 Cd1 O1 C13 11.1(3) . . . . ? O7 Cd1 O1 C13 -77.0(2) . . . . ? N6 Cd1 O1 C13 107.7(2) 5_576 . . . ? O4 Cd1 O1 C13 -166.8(2) 1_545 . . . ? O3 Cd1 O1 C13 -172.0(2) 1_545 . . . ? C14 Cd1 O1 C13 -169.4(2) 1_545 . . . ? C4 N1 N2 C3 0.5(4) . . . . ? C1 N1 N2 C3 174.2(3) . . . . ? O1 Cd1 N3 C4 -17.8(3) . . . . ? O7 Cd1 N3 C4 67.7(3) . . . . ? N6 Cd1 N3 C4 -110.7(3) 5_576 . . . ? O4 Cd1 N3 C4 159.1(3) 1_545 . . . ? O3 Cd1 N3 C4 163.9(3) 1_545 . . . ? C14 Cd1 N3 C4 162.6(3) 1_545 . . . ? O1 Cd1 N3 C3 153.9(3) . . . . ? O7 Cd1 N3 C3 -120.5(3) . . . . ? N6 Cd1 N3 C3 61.1(3) 5_576 . . . ? O4 Cd1 N3 C3 -29.2(4) 1_545 . . . ? O3 Cd1 N3 C3 -24.3(3) 1_545 . . . ? C14 Cd1 N3 C3 -25.6(4) 1_545 . . . ? C6 N4 N5 C5 -0.4(4) . . . . ? C2 N4 N5 C5 -177.7(3) . . . . ? C4 N1 C1 C2 109.0(4) . . . . ? N2 N1 C1 C2 -63.5(4) . . . . ? C6 N4 C2 C1 134.5(4) . . . . ? N5 N4 C2 C1 -48.6(5) . . . . ? N1 C1 C2 N4 -47.6(4) . . . . ? N1 N2 C3 N3 -0.1(4) . . . . ? C4 N3 C3 N2 -0.3(5) . . . . ? Cd1 N3 C3 N2 -173.3(3) . . . . ? C3 N3 C4 N1 0.5(4) . . . . ? Cd1 N3 C4 N1 174.2(2) . . . . ? N2 N1 C4 N3 -0.7(4) . . . . ? C1 N1 C4 N3 -173.9(3) . . . . ? N4 N5 C5 N6 0.0(5) . . . . ? C6 N6 C5 N5 0.5(5) . . . . ? Cd1 N6 C5 N5 165.0(3) 5_576 . . . ? C5 N6 C6 N4 -0.7(4) . . . . ? Cd1 N6 C6 N4 -168.2(2) 5_576 . . . ? N5 N4 C6 N6 0.7(4) . . . . ? C2 N4 C6 N6 177.9(3) . . . . ? C12 C7 C8 C9 -0.5(5) . . . . ? C13 C7 C8 C9 -179.8(3) . . . . ? C7 C8 C9 C10 -0.6(5) . . . . ? C7 C8 C9 C14 178.1(3) . . . . ? C8 C9 C10 C11 1.2(5) . . . . ? C14 C9 C10 C11 -177.6(3) . . . . ? C9 C10 C11 C12 -0.7(5) . . . . ? C9 C10 C11 N7 -179.9(3) . . . . ? O6 N7 C11 C12 21.8(5) . . . . ? O5 N7 C11 C12 -154.8(4) . . . . ? O6 N7 C11 C10 -159.0(4) . . . . ? O5 N7 C11 C10 24.5(6) . . . . ? C10 C11 C12 C7 -0.5(5) . . . . ? N7 C11 C12 C7 178.8(3) . . . . ? C8 C7 C12 C11 1.1(5) . . . . ? C13 C7 C12 C11 -179.7(3) . . . . ? Cd1 O1 C13 O2 -4.3(4) . . . . ? Cd1 O1 C13 C7 174.4(2) . . . . ? C12 C7 C13 O2 170.9(3) . . . . ? C8 C7 C13 O2 -9.9(5) . . . . ? C12 C7 C13 O1 -8.0(5) . . . . ? C8 C7 C13 O1 171.3(3) . . . . ? Cd1 O4 C14 O3 -2.8(4) 1_565 . . . ? Cd1 O4 C14 C9 178.0(2) 1_565 . . . ? Cd1 O3 C14 O4 2.6(3) 1_565 . . . ? Cd1 O3 C14 C9 -178.2(3) 1_565 . . . ? C10 C9 C14 O4 0.5(5) . . . . ? C8 C9 C14 O4 -178.3(3) . . . . ? C10 C9 C14 O3 -178.8(3) . . . . ? C8 C9 C14 O3 2.5(5) . . . . ? 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 O7 H1W O8 0.834(19) 1.93(2) 2.758(4) 172(4) 7_576 O7 H2W O3 0.78(5) 1.90(5) 2.685(4) 177(5) 7_576 O8 H4W O2 0.834(18) 1.93(2) 2.768(4) 176(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 0.759 _refine_diff_density_min -0.731 _refine_diff_density_rms 0.207 _database_code_depnum_ccdc_archive 'CCDC 968325' ####################################################################### # # 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_CdbteIbdc _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H13 Cd I N6 O5, H2 O ' _chemical_formula_sum 'C14 H15 Cd I N6 O6' _chemical_formula_weight 602.62 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.049(4) _cell_length_b 10.4209(17) _cell_length_c 20.232(4) _cell_angle_alpha 90.00 _cell_angle_beta 120.052(4) _cell_angle_gamma 90.00 _cell_volume 3841.3(13) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4214 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.084 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2320 _exptl_absorpt_coefficient_mu 2.789 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4017 _exptl_absorpt_correction_T_max 0.6054 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.63 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9301 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 26.89 _reflns_number_total 4081 _reflns_number_gt 3027 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _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^)+(0.0890P)^2^+2.5800P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4081 _refine_ls_number_parameters 266 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1615 _refine_ls_wR_factor_gt 0.1443 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.065 _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 0.13624(2) 0.42784(5) 0.42109(2) 0.02495(17) Uani 1 1 d . . . I1 I 0.04172(3) -0.07263(6) 0.09874(3) 0.0519(2) Uani 1 1 d . . . O1 O 0.1087(3) 0.2729(5) 0.3300(3) 0.0369(12) Uani 1 1 d . . . O2 O 0.1416(3) 0.1795(5) 0.4392(3) 0.0413(13) Uani 1 1 d . . . O3 O 0.1437(3) -0.3139(6) 0.4432(3) 0.0477(15) Uani 1 1 d . . . O4 O 0.1043(3) -0.4122(5) 0.3341(3) 0.0408(13) Uani 1 1 d . . . O5 O 0.2529(3) 0.4421(5) 0.4377(3) 0.0373(12) Uani 1 1 d D . . H1W H 0.289(3) 0.420(6) 0.484(2) 0.045 Uiso 1 1 d D . . H2W H 0.254(3) 0.527(2) 0.437(4) 0.045 Uiso 1 1 d D . . O6 O 0.3190(4) 0.6638(7) 0.4311(4) 0.0662(19) Uani 1 1 d D . . H3W H 0.339(3) 0.716(2) 0.410(4) 0.079 Uiso 1 1 d D . . H4W H 0.319(3) 0.704(2) 0.4709(17) 0.079 Uiso 1 1 d D . . N1 N 0.2175(3) 0.4969(7) 0.6627(3) 0.0364(15) Uani 1 1 d . . . N2 N 0.2062(4) 0.3675(9) 0.6673(4) 0.055(2) Uani 1 1 d . . . N3 N 0.1832(3) 0.4227(6) 0.5507(3) 0.0302(13) Uani 1 1 d . . . N4 N 0.1042(3) 0.6071(7) 0.6829(3) 0.0355(15) Uani 1 1 d . . . N5 N 0.0885(3) 0.6911(8) 0.6256(4) 0.0507(19) Uani 1 1 d . . . N6 N -0.0142(3) 0.5942(6) 0.6090(3) 0.0343(15) Uani 1 1 d . . . C1 C 0.2363(4) 0.5836(10) 0.7269(4) 0.051(3) Uani 1 1 d . . . H1A H 0.2440 0.6701 0.7133 0.062 Uiso 1 1 calc R . . H1B H 0.2824 0.5552 0.7711 0.062 Uiso 1 1 calc R . . C2 C 0.1781(4) 0.5880(10) 0.7480(4) 0.048(2) Uani 1 1 d . . . H2A H 0.1790 0.5075 0.7735 0.057 Uiso 1 1 calc R . . H2B H 0.1891 0.6579 0.7846 0.057 Uiso 1 1 calc R . . C3 C 0.1848(5) 0.3280(9) 0.5972(4) 0.046(2) Uani 1 1 d . . . H3A H 0.1720 0.2425 0.5812 0.055 Uiso 1 1 calc R . . C4 C 0.2050(4) 0.5260(9) 0.5950(4) 0.0357(18) Uani 1 1 d . . . H4A H 0.2105 0.6083 0.5794 0.043 Uiso 1 1 calc RD . . C5 C 0.0178(5) 0.6782(10) 0.5830(5) 0.054(2) Uani 1 1 d . . . H5A H -0.0095 0.7239 0.5371 0.065 Uiso 1 1 calc R . . C6 C 0.0434(4) 0.5536(8) 0.6727(4) 0.0355(18) Uani 1 1 d . . . H6A H 0.0412 0.4941 0.7064 0.043 Uiso 1 1 calc R . . C7 C 0.1095(3) 0.0474(7) 0.3299(4) 0.0245(15) Uani 1 1 d . . . C8 C 0.1208(3) -0.0685(7) 0.3694(3) 0.0240(14) Uani 1 1 d . . . H8A H 0.1359 -0.0674 0.4217 0.029 Uiso 1 1 calc R . . C9 C 0.1096(3) -0.1850(7) 0.3318(3) 0.0246(15) Uani 1 1 d . . . C10 C 0.0870(3) -0.1860(7) 0.2537(3) 0.0290(16) Uani 1 1 d . . . H10A H 0.0798 -0.2643 0.2278 0.035 Uiso 1 1 calc R . . C11 C 0.0753(4) -0.0708(7) 0.2150(4) 0.0280(15) Uani 1 1 d . . . C12 C 0.0857(4) 0.0438(7) 0.2523(4) 0.0302(16) Uani 1 1 d . . . H12A H 0.0767 0.1210 0.2250 0.036 Uiso 1 1 calc R . . C13 C 0.1202(3) 0.1743(7) 0.3690(3) 0.0249(15) Uani 1 1 d . . . C14 C 0.1191(4) -0.3113(7) 0.3715(4) 0.0310(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.0316(3) 0.0199(3) 0.0208(3) 0.00033(19) 0.01130(19) 0.0004(2) I1 0.0772(4) 0.0475(4) 0.0285(3) 0.0003(2) 0.0245(3) 0.0056(3) O1 0.060(3) 0.013(3) 0.041(3) 0.001(2) 0.028(3) -0.002(2) O2 0.051(3) 0.035(4) 0.026(2) -0.008(2) 0.010(2) 0.010(3) O3 0.081(4) 0.029(4) 0.024(2) 0.005(2) 0.021(3) 0.003(3) O4 0.062(3) 0.018(3) 0.037(3) 0.001(2) 0.020(3) -0.001(3) O5 0.032(2) 0.033(3) 0.040(3) 0.004(2) 0.013(2) 0.000(2) O6 0.106(5) 0.049(5) 0.070(4) -0.010(4) 0.064(4) -0.032(4) N1 0.037(3) 0.039(5) 0.035(3) -0.010(3) 0.019(3) 0.006(3) N2 0.082(5) 0.055(6) 0.032(3) 0.012(4) 0.031(3) 0.013(5) N3 0.040(3) 0.031(4) 0.019(3) -0.001(2) 0.014(2) 0.003(3) N4 0.032(3) 0.048(5) 0.027(3) -0.003(3) 0.016(2) 0.004(3) N5 0.040(3) 0.049(5) 0.062(4) 0.016(4) 0.025(3) -0.007(3) N6 0.030(3) 0.036(4) 0.034(3) 0.008(3) 0.014(2) 0.004(3) C1 0.038(4) 0.076(8) 0.034(4) -0.019(4) 0.014(3) 0.002(4) C2 0.037(4) 0.070(7) 0.030(4) -0.018(4) 0.012(3) -0.001(4) C3 0.078(6) 0.028(5) 0.040(4) -0.002(4) 0.036(4) 0.002(4) C4 0.033(4) 0.045(5) 0.030(4) 0.006(3) 0.017(3) 0.008(3) C5 0.052(5) 0.051(7) 0.047(5) 0.022(4) 0.016(4) 0.009(5) C6 0.043(4) 0.031(5) 0.034(4) 0.006(3) 0.020(3) 0.005(3) C7 0.022(3) 0.023(4) 0.029(3) -0.002(3) 0.014(3) 0.002(3) C8 0.025(3) 0.026(4) 0.018(3) 0.004(3) 0.008(2) 0.003(3) C9 0.030(3) 0.018(4) 0.025(3) -0.005(3) 0.012(3) -0.002(3) C10 0.038(3) 0.025(4) 0.017(3) 0.003(3) 0.009(3) 0.003(3) C11 0.034(3) 0.025(4) 0.026(3) -0.001(3) 0.015(3) -0.007(3) C12 0.032(3) 0.027(5) 0.040(4) 0.010(3) 0.023(3) 0.004(3) C13 0.025(3) 0.024(4) 0.027(3) -0.007(3) 0.013(3) -0.001(3) C14 0.037(3) 0.022(4) 0.031(3) 0.002(3) 0.015(3) 0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O4 2.267(5) 1_565 ? Cd1 N3 2.293(5) . ? Cd1 O1 2.295(5) . ? Cd1 O5 2.310(5) . ? Cd1 N6 2.336(6) 5_566 ? Cd1 O2 2.608(6) . ? I1 C11 2.090(6) . ? O1 C13 1.244(8) . ? O2 C13 1.258(7) . ? O3 C14 1.273(8) . ? O4 C14 1.241(9) . ? O4 Cd1 2.267(5) 1_545 ? O5 H1W 0.89(2) . ? O5 H2W 0.885(19) . ? O6 H3W 0.905(19) . ? O6 H4W 0.903(19) . ? N1 C4 1.296(9) . ? N1 N2 1.380(11) . ? N1 C1 1.464(10) . ? N2 C3 1.322(10) . ? N3 C4 1.326(10) . ? N3 C3 1.352(10) . ? N4 C6 1.315(9) . ? N4 N5 1.355(9) . ? N4 C2 1.463(9) . ? N5 C5 1.300(10) . ? N6 C6 1.321(9) . ? N6 C5 1.362(10) . ? N6 Cd1 2.336(6) 5_566 ? C1 C2 1.487(10) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9400 . ? C4 H4A 0.9400 . ? C5 H5A 0.9400 . ? C6 H6A 0.9400 . ? C7 C12 1.388(9) . ? C7 C8 1.402(9) . ? C7 C13 1.499(9) . ? C8 C9 1.389(9) . ? C8 H8A 0.9400 . ? C9 C10 1.403(8) . ? C9 C14 1.502(10) . ? C10 C11 1.386(9) . ? C10 H10A 0.9400 . ? C11 C12 1.371(10) . ? C12 H12A 0.9400 . ? 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 N3 134.0(2) 1_565 . ? O4 Cd1 O1 92.10(19) 1_565 . ? N3 Cd1 O1 133.8(2) . . ? O4 Cd1 O5 86.9(2) 1_565 . ? N3 Cd1 O5 90.96(19) . . ? O1 Cd1 O5 89.12(18) . . ? O4 Cd1 N6 90.5(2) 1_565 5_566 ? N3 Cd1 N6 94.8(2) . 5_566 ? O1 Cd1 N6 85.4(2) . 5_566 ? O5 Cd1 N6 173.85(19) . 5_566 ? O4 Cd1 O2 144.45(17) 1_565 . ? N3 Cd1 O2 81.53(19) . . ? O1 Cd1 O2 52.46(15) . . ? O5 Cd1 O2 94.31(18) . . ? N6 Cd1 O2 84.5(2) 5_566 . ? C13 O1 Cd1 100.4(4) . . ? C13 O2 Cd1 85.3(4) . . ? C14 O4 Cd1 105.3(4) . 1_545 ? Cd1 O5 H1W 115(5) . . ? Cd1 O5 H2W 95(5) . . ? H1W O5 H2W 105(3) . . ? H3W O6 H4W 110(3) . . ? C4 N1 N2 110.5(6) . . ? C4 N1 C1 128.0(8) . . ? N2 N1 C1 121.5(7) . . ? C3 N2 N1 102.1(6) . . ? C4 N3 C3 104.1(6) . . ? C4 N3 Cd1 123.9(5) . . ? C3 N3 Cd1 131.2(5) . . ? C6 N4 N5 109.7(6) . . ? C6 N4 C2 126.6(7) . . ? N5 N4 C2 123.6(6) . . ? C5 N5 N4 102.1(6) . . ? C6 N6 C5 101.1(6) . . ? C6 N6 Cd1 125.1(5) . 5_566 ? C5 N6 Cd1 130.9(5) . 5_566 ? N1 C1 C2 112.3(7) . . ? N1 C1 H1A 109.2 . . ? C2 C1 H1A 109.2 . . ? N1 C1 H1B 109.2 . . ? C2 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? N4 C2 C1 113.7(6) . . ? N4 C2 H2A 108.8 . . ? C1 C2 H2A 108.8 . . ? N4 C2 H2B 108.8 . . ? C1 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? N2 C3 N3 113.3(8) . . ? N2 C3 H3A 123.4 . . ? N3 C3 H3A 123.4 . . ? N1 C4 N3 110.0(8) . . ? N1 C4 H4A 125.0 . . ? N3 C4 H4A 125.0 . . ? N5 C5 N6 115.7(7) . . ? N5 C5 H5A 122.2 . . ? N6 C5 H5A 122.2 . . ? N4 C6 N6 111.3(7) . . ? N4 C6 H6A 124.3 . . ? N6 C6 H6A 124.3 . . ? C12 C7 C8 118.9(6) . . ? C12 C7 C13 119.6(6) . . ? C8 C7 C13 121.4(6) . . ? C9 C8 C7 120.4(6) . . ? C9 C8 H8A 119.8 . . ? C7 C8 H8A 119.8 . . ? C8 C9 C10 119.5(6) . . ? C8 C9 C14 122.1(6) . . ? C10 C9 C14 118.4(6) . . ? C11 C10 C9 119.6(6) . . ? C11 C10 H10A 120.2 . . ? C9 C10 H10A 120.2 . . ? C12 C11 C10 120.6(6) . . ? C12 C11 I1 119.9(5) . . ? C10 C11 I1 119.5(5) . . ? C11 C12 C7 120.9(6) . . ? C11 C12 H12A 119.5 . . ? C7 C12 H12A 119.5 . . ? O1 C13 O2 121.8(6) . . ? O1 C13 C7 117.6(5) . . ? O2 C13 C7 120.6(6) . . ? O4 C14 O3 120.7(7) . . ? O4 C14 C9 119.4(6) . . ? O3 C14 C9 119.8(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Cd1 O1 C13 -176.7(4) 1_565 . . . ? N3 Cd1 O1 C13 5.9(5) . . . . ? O5 Cd1 O1 C13 96.4(4) . . . . ? N6 Cd1 O1 C13 -86.3(4) 5_566 . . . ? O2 Cd1 O1 C13 0.2(4) . . . . ? O4 Cd1 O2 C13 5.0(5) 1_565 . . . ? N3 Cd1 O2 C13 -176.1(4) . . . . ? O1 Cd1 O2 C13 -0.2(3) . . . . ? O5 Cd1 O2 C13 -85.8(4) . . . . ? N6 Cd1 O2 C13 88.1(4) 5_566 . . . ? C4 N1 N2 C3 -1.6(8) . . . . ? C1 N1 N2 C3 174.9(7) . . . . ? O4 Cd1 N3 C4 -6.6(7) 1_565 . . . ? O1 Cd1 N3 C4 169.8(5) . . . . ? O5 Cd1 N3 C4 80.1(5) . . . . ? N6 Cd1 N3 C4 -102.0(6) 5_566 . . . ? O2 Cd1 N3 C4 174.3(6) . . . . ? O4 Cd1 N3 C3 161.5(6) 1_565 . . . ? O1 Cd1 N3 C3 -22.1(8) . . . . ? O5 Cd1 N3 C3 -111.8(7) . . . . ? N6 Cd1 N3 C3 66.1(7) 5_566 . . . ? O2 Cd1 N3 C3 -17.6(7) . . . . ? C6 N4 N5 C5 -2.0(9) . . . . ? C2 N4 N5 C5 -178.2(7) . . . . ? C4 N1 C1 C2 114.6(9) . . . . ? N2 N1 C1 C2 -61.1(10) . . . . ? C6 N4 C2 C1 142.1(8) . . . . ? N5 N4 C2 C1 -42.3(11) . . . . ? N1 C1 C2 N4 -48.6(11) . . . . ? N1 N2 C3 N3 0.8(9) . . . . ? C4 N3 C3 N2 0.1(10) . . . . ? Cd1 N3 C3 N2 -169.7(5) . . . . ? N2 N1 C4 N3 1.8(8) . . . . ? C1 N1 C4 N3 -174.4(6) . . . . ? C3 N3 C4 N1 -1.2(8) . . . . ? Cd1 N3 C4 N1 169.6(4) . . . . ? N4 N5 C5 N6 1.5(11) . . . . ? C6 N6 C5 N5 -0.4(11) . . . . ? Cd1 N6 C5 N5 160.8(6) 5_566 . . . ? N5 N4 C6 N6 1.9(9) . . . . ? C2 N4 C6 N6 178.0(7) . . . . ? C5 N6 C6 N4 -0.9(9) . . . . ? Cd1 N6 C6 N4 -163.6(5) 5_566 . . . ? C12 C7 C8 C9 1.3(9) . . . . ? C13 C7 C8 C9 179.2(5) . . . . ? C7 C8 C9 C10 0.0(9) . . . . ? C7 C8 C9 C14 -178.3(6) . . . . ? C8 C9 C10 C11 -0.6(9) . . . . ? C14 C9 C10 C11 177.7(6) . . . . ? C9 C10 C11 C12 0.1(10) . . . . ? C9 C10 C11 I1 179.9(4) . . . . ? C10 C11 C12 C7 1.2(10) . . . . ? I1 C11 C12 C7 -178.6(5) . . . . ? C8 C7 C12 C11 -1.8(9) . . . . ? C13 C7 C12 C11 -179.8(6) . . . . ? Cd1 O1 C13 O2 -0.5(7) . . . . ? Cd1 O1 C13 C7 -178.9(4) . . . . ? Cd1 O2 C13 O1 0.4(6) . . . . ? Cd1 O2 C13 C7 178.8(5) . . . . ? C12 C7 C13 O1 -1.7(9) . . . . ? C8 C7 C13 O1 -179.6(6) . . . . ? C12 C7 C13 O2 179.9(6) . . . . ? C8 C7 C13 O2 2.0(9) . . . . ? Cd1 O4 C14 O3 -2.8(8) 1_545 . . . ? Cd1 O4 C14 C9 175.6(5) 1_545 . . . ? C8 C9 C14 O4 175.8(6) . . . . ? C10 C9 C14 O4 -2.5(9) . . . . ? C8 C9 C14 O3 -5.8(10) . . . . ? C10 C9 C14 O3 175.9(6) . . . . ? 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 O5 H1W O2 0.89(2) 1.83(3) 2.682(7) 159(6) 7_556 O5 H2W O6 0.885(19) 2.02(5) 2.735(8) 137(6) . O6 H3W N5 0.905(19) 2.22(3) 3.103(8) 165(4) 7_566 O6 H4W O3 0.903(19) 1.89(3) 2.743(8) 156(5) 7_556 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.89 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.942 _refine_diff_density_min -1.474 _refine_diff_density_rms 0.137 _database_code_depnum_ccdc_archive 'CCDC 968326' ####################################################################### # # 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_CdbteOHbdc _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H10 Cd N3 O6, H2O' _chemical_formula_sum 'C11 H12 Cd N3 O7' _chemical_formula_weight 410.64 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' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6185(4) _cell_length_b 9.5814(14) _cell_length_c 10.5272(16) _cell_angle_alpha 85.45(2) _cell_angle_beta 69.833(14) _cell_angle_gamma 70.509(13) _cell_volume 679.44(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2533 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 25.3 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.007 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 406 _exptl_absorpt_coefficient_mu 1.648 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6376 _exptl_absorpt_correction_T_max 0.7340 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6575 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2464 _reflns_number_gt 2279 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _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^)+(0.0468P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2464 _refine_ls_number_parameters 212 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0277 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0665 _refine_ls_wR_factor_gt 0.0645 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.021 _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 0.04327(3) 0.295056(19) 0.449697(18) 0.02403(10) Uani 1 1 d . . . O1 O 0.1682(3) 0.4525(2) 0.5490(2) 0.0289(5) Uani 1 1 d . . . O2 O -0.0013(3) 0.5676(2) 0.7488(2) 0.0357(5) Uani 1 1 d . . . O3 O 0.7475(3) -0.0290(2) 0.5348(2) 0.0363(5) Uani 1 1 d . . . O4 O 0.6465(3) -0.1780(2) 0.6901(2) 0.0316(5) Uani 1 1 d . . . O5 O 0.1675(4) 0.1720(3) 1.0805(2) 0.0487(6) Uani 1 1 d . . . H5 H 0.0942 0.2523 1.1186 0.073 Uiso 1 1 calc R . . O6 O -0.1431(4) 0.1902(3) 0.3877(3) 0.0540(7) Uani 1 1 d D . . O7 O 0.3148(5) -0.2561(3) 0.8095(3) 0.0550(7) Uani 1 1 d D . . N1 N -0.3774(4) 0.3554(3) 0.8611(2) 0.0293(5) Uani 1 1 d . . . N2 N -0.2593(4) 0.2204(3) 0.8841(3) 0.0385(6) Uani 1 1 d . . . N3 N -0.1495(4) 0.2772(3) 0.6661(2) 0.0293(5) Uani 1 1 d . . . C1 C -0.5390(5) 0.4501(4) 0.9720(3) 0.0344(7) Uani 1 1 d . . . H1A H -0.5926 0.3896 1.0430 0.041 Uiso 1 1 calc R . . H1B H -0.6441 0.5102 0.9394 0.041 Uiso 1 1 calc R . . C2 C -0.1266(5) 0.1781(3) 0.7642(3) 0.0350(7) Uani 1 1 d . . . H2A H -0.0248 0.0876 0.7472 0.042 Uiso 1 1 calc R . . C3 C -0.3097(4) 0.3859(3) 0.7322(3) 0.0310(7) Uani 1 1 d . . . H3A H -0.3670 0.4719 0.6936 0.037 Uiso 1 1 calc R . . C4 C 0.2222(4) 0.3234(3) 0.7423(3) 0.0231(6) Uani 1 1 d . . . C5 C 0.3801(4) 0.2068(3) 0.6634(3) 0.0242(6) Uani 1 1 d . . . H5A H 0.4324 0.2144 0.5702 0.029 Uiso 1 1 calc R . . C6 C 0.4587(4) 0.0786(3) 0.7254(3) 0.0239(6) Uani 1 1 d . . . C7 C 0.3829(4) 0.0698(3) 0.8651(3) 0.0275(6) Uani 1 1 d . . . H7A H 0.4351 -0.0160 0.9061 0.033 Uiso 1 1 calc R . . C8 C 0.2300(4) 0.1879(3) 0.9441(3) 0.0279(6) Uani 1 1 d . . . C9 C 0.1498(4) 0.3145(3) 0.8820(3) 0.0259(6) Uani 1 1 d . . . H9A H 0.0470 0.3937 0.9343 0.031 Uiso 1 1 calc R . . C10 C 0.1251(4) 0.4562(3) 0.6765(3) 0.0251(6) Uani 1 1 d . . . C11 C 0.6277(4) -0.0488(3) 0.6437(3) 0.0250(6) Uani 1 1 d . . . H1W H -0.185(5) 0.210(3) 0.320(3) 0.030 Uiso 1 1 d D . . H2W H -0.197(4) 0.134(3) 0.442(3) 0.030 Uiso 1 1 d D . . H3W H 0.419(4) -0.231(3) 0.769(3) 0.030 Uiso 1 1 d D . . H4W H 0.228(4) -0.190(3) 0.870(3) 0.030 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.02342(14) 0.02016(14) 0.01886(14) -0.00068(9) -0.00285(9) 0.00083(9) O1 0.0337(11) 0.0241(10) 0.0261(11) 0.0032(9) -0.0141(9) -0.0026(9) O2 0.0388(12) 0.0205(10) 0.0352(12) -0.0003(9) -0.0103(10) 0.0040(9) O3 0.0315(12) 0.0264(11) 0.0344(13) -0.0029(10) 0.0021(10) -0.0016(9) O4 0.0293(11) 0.0195(10) 0.0337(12) -0.0003(9) -0.0056(9) 0.0024(8) O5 0.0678(17) 0.0363(12) 0.0171(11) -0.0030(10) -0.0059(11) 0.0065(12) O6 0.079(2) 0.0680(18) 0.0443(16) 0.0285(14) -0.0362(15) -0.0506(16) O7 0.0574(18) 0.073(2) 0.0453(16) 0.0139(14) -0.0184(13) -0.0358(16) N1 0.0302(13) 0.0339(13) 0.0196(12) -0.0057(10) -0.0014(10) -0.0110(11) N2 0.0433(16) 0.0354(14) 0.0270(14) 0.0035(12) -0.0038(12) -0.0097(12) N3 0.0299(13) 0.0324(13) 0.0191(12) -0.0039(10) -0.0012(10) -0.0081(11) C1 0.0281(15) 0.0420(17) 0.0253(16) -0.0104(14) 0.0024(12) -0.0109(14) C2 0.0381(18) 0.0300(16) 0.0281(16) 0.0007(13) -0.0066(14) -0.0047(14) C3 0.0295(16) 0.0341(16) 0.0232(15) -0.0019(13) -0.0055(12) -0.0057(13) C4 0.0236(14) 0.0196(13) 0.0252(14) -0.0018(11) -0.0104(11) -0.0030(11) C5 0.0228(14) 0.0228(13) 0.0227(14) -0.0027(11) -0.0073(11) -0.0019(11) C6 0.0239(14) 0.0195(13) 0.0256(15) -0.0029(11) -0.0103(12) -0.0009(11) C7 0.0338(16) 0.0229(14) 0.0240(15) -0.0008(12) -0.0139(12) -0.0025(12) C8 0.0326(16) 0.0254(14) 0.0213(15) -0.0014(12) -0.0086(12) -0.0038(12) C9 0.0251(14) 0.0216(13) 0.0259(15) -0.0075(12) -0.0076(12) -0.0004(11) C10 0.0222(14) 0.0197(13) 0.0325(17) 0.0011(12) -0.0109(12) -0.0039(11) C11 0.0229(14) 0.0216(14) 0.0257(15) -0.0055(12) -0.0091(12) 0.0009(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O4 2.259(2) 2_656 ? Cd1 O6 2.269(3) . ? Cd1 N3 2.275(2) . ? Cd1 O1 2.416(2) 2_566 ? Cd1 O2 2.438(2) 2_566 ? Cd1 O1 2.483(2) . ? Cd1 O3 2.543(2) 2_656 ? O1 C10 1.267(4) . ? O1 Cd1 2.416(2) 2_566 ? O2 C10 1.258(3) . ? O2 Cd1 2.438(2) 2_566 ? O3 C11 1.242(4) . ? O3 Cd1 2.543(2) 2_656 ? O4 C11 1.275(3) . ? O4 Cd1 2.259(2) 2_656 ? O5 C8 1.362(4) . ? O5 H5 0.8200 . ? O6 H1W 0.864(18) . ? O6 H2W 0.853(18) . ? O7 H3W 0.867(18) . ? O7 H4W 0.863(18) . ? N1 C3 1.322(4) . ? N1 N2 1.365(4) . ? N1 C1 1.461(4) . ? N2 C2 1.306(4) . ? N3 C3 1.318(4) . ? N3 C2 1.363(4) . ? C1 C1 1.525(6) 2_467 ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9300 . ? C3 H3A 0.9300 . ? C4 C9 1.388(4) . ? C4 C5 1.396(4) . ? C4 C10 1.494(4) . ? C5 C6 1.394(4) . ? C5 H5A 0.9300 . ? C6 C7 1.389(4) . ? C6 C11 1.498(4) . ? C7 C8 1.389(4) . ? C7 H7A 0.9300 . ? C8 C9 1.388(4) . ? C9 H9A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cd1 O6 103.14(10) 2_656 . ? O4 Cd1 N3 137.65(8) 2_656 . ? O6 Cd1 N3 85.72(9) . . ? O4 Cd1 O1 129.68(7) 2_656 2_566 ? O6 Cd1 O1 95.54(9) . 2_566 ? N3 Cd1 O1 89.43(8) . 2_566 ? O4 Cd1 O2 84.87(7) 2_656 2_566 ? O6 Cd1 O2 77.76(8) . 2_566 ? N3 Cd1 O2 137.21(8) . 2_566 ? O1 Cd1 O2 53.98(7) 2_566 2_566 ? O4 Cd1 O1 90.50(7) 2_656 . ? O6 Cd1 O1 166.13(10) . . ? N3 Cd1 O1 85.82(8) . . ? O1 Cd1 O1 73.40(8) 2_566 . ? O2 Cd1 O1 101.33(7) 2_566 . ? O4 Cd1 O3 53.88(7) 2_656 2_656 ? O6 Cd1 O3 84.58(9) . 2_656 ? N3 Cd1 O3 86.71(8) . 2_656 ? O1 Cd1 O3 176.13(6) 2_566 2_656 ? O2 Cd1 O3 129.70(7) 2_566 2_656 ? O1 Cd1 O3 105.88(7) . 2_656 ? C10 O1 Cd1 92.61(16) . 2_566 ? C10 O1 Cd1 118.00(18) . . ? Cd1 O1 Cd1 106.60(8) 2_566 . ? C10 O2 Cd1 91.81(17) . 2_566 ? C11 O3 Cd1 85.72(16) . 2_656 ? C11 O4 Cd1 98.07(17) . 2_656 ? C8 O5 H5 109.5 . . ? Cd1 O6 H1W 129(2) . . ? Cd1 O6 H2W 119(2) . . ? H1W O6 H2W 111(3) . . ? H3W O7 H4W 111(3) . . ? C3 N1 N2 109.7(2) . . ? C3 N1 C1 128.6(3) . . ? N2 N1 C1 121.4(2) . . ? C2 N2 N1 102.5(2) . . ? C3 N3 C2 102.7(3) . . ? C3 N3 Cd1 122.8(2) . . ? C2 N3 Cd1 133.7(2) . . ? N1 C1 C1 109.2(3) . 2_467 ? N1 C1 H1A 109.8 . . ? C1 C1 H1A 109.8 2_467 . ? N1 C1 H1B 109.8 . . ? C1 C1 H1B 109.8 2_467 . ? H1A C1 H1B 108.3 . . ? N2 C2 N3 114.5(3) . . ? N2 C2 H2A 122.7 . . ? N3 C2 H2A 122.7 . . ? N3 C3 N1 110.5(3) . . ? N3 C3 H3A 124.7 . . ? N1 C3 H3A 124.7 . . ? C9 C4 C5 120.2(2) . . ? C9 C4 C10 119.6(2) . . ? C5 C4 C10 120.2(3) . . ? C4 C5 C6 119.4(3) . . ? C4 C5 H5A 120.3 . . ? C6 C5 H5A 120.3 . . ? C7 C6 C5 119.8(3) . . ? C7 C6 C11 119.3(2) . . ? C5 C6 C11 120.8(2) . . ? C8 C7 C6 120.7(3) . . ? C8 C7 H7A 119.7 . . ? C6 C7 H7A 119.7 . . ? O5 C8 C7 117.1(3) . . ? O5 C8 C9 123.5(3) . . ? C7 C8 C9 119.4(3) . . ? C4 C9 C8 120.3(2) . . ? C4 C9 H9A 119.8 . . ? C8 C9 H9A 119.8 . . ? O2 C10 O1 121.4(2) . . ? O2 C10 C4 119.5(3) . . ? O1 C10 C4 119.1(2) . . ? O3 C11 O4 121.0(2) . . ? O3 C11 C6 121.0(2) . . ? O4 C11 C6 118.0(2) . . ? 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 O1 C10 -126.16(19) 2_656 . . . ? O6 Cd1 O1 C10 64.2(4) . . . . ? N3 Cd1 O1 C10 11.6(2) . . . . ? O1 Cd1 O1 C10 102.3(2) 2_566 . . . ? O2 Cd1 O1 C10 148.98(19) 2_566 . . . ? O3 Cd1 O1 C10 -73.8(2) 2_656 . . . ? C11 Cd1 O1 C10 -101.1(2) 2_656 . . . ? O4 Cd1 O1 Cd1 131.58(9) 2_656 . . 2_566 ? O6 Cd1 O1 Cd1 -38.1(3) . . . 2_566 ? N3 Cd1 O1 Cd1 -90.66(10) . . . 2_566 ? O1 Cd1 O1 Cd1 0.0 2_566 . . 2_566 ? O2 Cd1 O1 Cd1 46.72(9) 2_566 . . 2_566 ? O3 Cd1 O1 Cd1 -176.03(7) 2_656 . . 2_566 ? C11 Cd1 O1 Cd1 156.59(9) 2_656 . . 2_566 ? C3 N1 N2 C2 -0.4(3) . . . . ? C1 N1 N2 C2 -174.8(3) . . . . ? O4 Cd1 N3 C3 161.8(2) 2_656 . . . ? O6 Cd1 N3 C3 -93.4(2) . . . . ? O1 Cd1 N3 C3 2.2(2) 2_566 . . . ? O2 Cd1 N3 C3 -26.6(3) 2_566 . . . ? O1 Cd1 N3 C3 75.6(2) . . . . ? O3 Cd1 N3 C3 -178.2(2) 2_656 . . . ? C11 Cd1 N3 C3 176.9(2) 2_656 . . . ? O4 Cd1 N3 C2 -6.8(3) 2_656 . . . ? O6 Cd1 N3 C2 98.1(3) . . . . ? O1 Cd1 N3 C2 -166.3(3) 2_566 . . . ? O2 Cd1 N3 C2 164.9(2) 2_566 . . . ? O1 Cd1 N3 C2 -92.9(3) . . . . ? O3 Cd1 N3 C2 13.2(3) 2_656 . . . ? C11 Cd1 N3 C2 8.4(3) 2_656 . . . ? C3 N1 C1 C1 -83.9(4) . . . 2_467 ? N2 N1 C1 C1 89.3(4) . . . 2_467 ? N1 N2 C2 N3 0.9(4) . . . . ? C3 N3 C2 N2 -1.0(4) . . . . ? Cd1 N3 C2 N2 169.2(2) . . . . ? C2 N3 C3 N1 0.7(3) . . . . ? Cd1 N3 C3 N1 -170.91(19) . . . . ? N2 N1 C3 N3 -0.2(3) . . . . ? C1 N1 C3 N3 173.7(3) . . . . ? C9 C4 C5 C6 2.8(4) . . . . ? C10 C4 C5 C6 -174.9(2) . . . . ? C4 C5 C6 C7 -1.7(4) . . . . ? C4 C5 C6 C11 179.8(2) . . . . ? C5 C6 C7 C8 -0.4(4) . . . . ? C11 C6 C7 C8 178.1(3) . . . . ? C6 C7 C8 O5 -178.3(3) . . . . ? C6 C7 C8 C9 1.4(4) . . . . ? C5 C4 C9 C8 -1.8(4) . . . . ? C10 C4 C9 C8 175.9(3) . . . . ? O5 C8 C9 C4 179.4(3) . . . . ? C7 C8 C9 C4 -0.3(4) . . . . ? Cd1 O2 C10 O1 -4.0(3) 2_566 . . . ? Cd1 O2 C10 C4 178.0(2) 2_566 . . . ? Cd1 O1 C10 O2 4.1(3) 2_566 . . . ? Cd1 O1 C10 O2 -106.3(3) . . . . ? Cd1 O1 C10 C4 -177.9(2) 2_566 . . . ? Cd1 O1 C10 C4 71.7(3) . . . . ? C9 C4 C10 O2 10.4(4) . . . . ? C5 C4 C10 O2 -171.8(3) . . . . ? C9 C4 C10 O1 -167.6(3) . . . . ? C5 C4 C10 O1 10.1(4) . . . . ? Cd1 O3 C11 O4 -11.1(3) 2_656 . . . ? Cd1 O3 C11 C6 168.0(2) 2_656 . . . ? Cd1 O4 C11 O3 12.6(3) 2_656 . . . ? Cd1 O4 C11 C6 -166.5(2) 2_656 . . . ? C7 C6 C11 O3 -151.7(3) . . . . ? C5 C6 C11 O3 26.9(4) . . . . ? C7 C6 C11 O4 27.4(4) . . . . ? C5 C6 C11 O4 -154.1(3) . . . . ? C7 C6 C11 Cd1 -26.3(10) . . . 2_656 ? C5 C6 C11 Cd1 152.3(7) . . . 2_656 ? 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 O5 H5 O2 0.82 2.08 2.844(3) 155.8 2_567 O6 H1W O7 0.864(18) 1.887(19) 2.744(4) 171(3) 2_556 O6 H2W O3 0.853(18) 1.86(2) 2.695(3) 164(3) 1_455 O7 H3W O4 0.867(18) 1.863(19) 2.729(3) 177(3) . O7 H4W N2 0.863(18) 2.66(3) 3.137(4) 116(3) 2_557 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.737 _refine_diff_density_min -0.643 _refine_diff_density_rms 0.086 _database_code_depnum_ccdc_archive 'CCDC 968327' ####################################################################### # # 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_CdbteSO3bdc _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H32 Cd N12 O13 S' _chemical_formula_weight 793.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc ' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.2282(16) _cell_length_b 14.3543(16) _cell_length_c 16.899(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.845(3) _cell_angle_gamma 90.00 _cell_volume 3151.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10712 _cell_measurement_theta_min 3.0088 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.840 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5529 _exptl_absorpt_correction_T_max 0.8500 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Nercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 27879 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.35 _reflns_number_total 5716 _reflns_number_gt 5157 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _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^)+(0.0479P)^2^+3.3280P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5716 _refine_ls_number_parameters 461 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.0976 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.074 _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 0.566173(18) 0.717641(17) 0.248778(13) 0.03216(10) Uani 1 1 d . . . S1 S 0.73354(7) 0.98245(6) 0.01667(5) 0.0364(2) Uani 1 1 d . . . O1 O 0.9883(2) 0.78203(16) -0.11380(17) 0.0485(7) Uani 1 1 d . . . O2 O 1.0399(2) 0.86690(17) -0.20886(15) 0.0420(6) Uani 1 1 d . . . HW H 1.052(4) 0.809(4) -0.231(3) 0.073(14) Uiso 1 1 d . . . O3 O 0.94669(19) 1.20562(15) -0.23223(15) 0.0391(6) Uani 1 1 d . . . O4 O 0.84544(19) 1.26247(15) -0.15268(16) 0.0408(6) Uani 1 1 d . . . O5 O 0.7290(3) 1.0628(2) 0.0644(2) 0.0927(13) Uani 1 1 d . . . O6 O 0.7680(3) 0.9037(3) 0.0639(3) 0.1143(17) Uani 1 1 d . . . O7 O 0.6389(3) 0.9667(4) -0.0362(2) 0.125(2) Uani 1 1 d . . . O8 O 0.5636(2) 0.8536(2) 0.17776(16) 0.0524(7) Uani 1 1 d D . . H1W H 0.539(3) 0.850(3) 0.1282(13) 0.063 Uiso 1 1 d D . . H2W H 0.596(3) 0.902(2) 0.195(2) 0.063 Uiso 1 1 d D . . O9 O 0.5511(2) 0.5729(2) 0.30855(16) 0.0527(7) Uani 1 1 d D . . H3W H 0.4908(17) 0.552(3) 0.300(2) 0.063 Uiso 1 1 d D . . H4W H 0.585(3) 0.568(3) 0.3567(15) 0.063 Uiso 1 1 d D . . O10 O 0.8245(2) 1.45591(19) -0.15555(19) 0.0545(7) Uani 1 1 d D . . H5W H 0.840(3) 1.3988(15) -0.158(3) 0.065 Uiso 1 1 d D . . H6W H 0.877(2) 1.487(3) -0.157(3) 0.065 Uiso 1 1 d D . . O11 O 0.6666(2) 1.4831(2) -0.28569(18) 0.0580(7) Uani 1 1 d D . . H7W H 0.721(2) 1.513(3) -0.274(3) 0.070 Uiso 1 1 d D . . O12 O 1.0096(2) 1.56407(19) -0.14748(18) 0.0506(7) Uani 1 1 d D . . H9W H 1.054(3) 1.525(2) -0.155(3) 0.061 Uiso 1 1 d D . . H10W H 1.017(3) 1.610(2) -0.178(2) 0.061 Uiso 1 1 d D . . O13 O 0.4906(2) 0.8531(2) 0.01789(19) 0.0628(8) Uani 1 1 d D . . H11W H 0.543(2) 0.870(3) -0.002(3) 0.075 Uiso 1 1 d D . . H12W H 0.440(2) 0.890(3) 0.009(3) 0.075 Uiso 1 1 d D . . N1 N 0.34256(19) 0.63206(19) 0.03168(16) 0.0310(6) Uani 1 1 d . . . N2 N 0.4267(2) 0.5927(2) 0.00918(17) 0.0418(7) Uani 1 1 d . . . N3 N 0.4672(2) 0.6533(2) 0.13393(16) 0.0353(6) Uani 1 1 d . . . N4 N 0.2986(2) 0.70212(18) -0.13982(16) 0.0298(6) Uani 1 1 d . . . N5 N 0.2968(2) 0.6276(2) -0.18938(18) 0.0440(7) Uani 1 1 d . . . N6 N 0.4183(2) 0.72873(19) -0.20922(17) 0.0359(7) Uani 1 1 d . . . N7 N 0.7842(2) 0.8493(2) 0.45092(16) 0.0359(6) Uani 1 1 d . . . N8 N 0.6961(2) 0.8816(3) 0.4716(2) 0.0614(10) Uani 1 1 d . . . N9 N 0.6611(2) 0.7941(2) 0.35953(17) 0.0435(8) Uani 1 1 d . . . N10 N 0.8345(2) 0.83607(18) 0.63165(15) 0.0302(6) Uani 1 1 d . . . N11 N 0.8305(2) 0.92256(19) 0.66377(17) 0.0364(6) Uani 1 1 d . . . N12 N 0.7167(2) 0.82743(19) 0.70508(16) 0.0339(6) Uani 1 1 d . . . C1 C 0.2431(2) 0.6301(2) -0.02230(19) 0.0334(7) Uani 1 1 d . . . H1A H 0.1893 0.6336 0.0094 0.040 Uiso 1 1 calc R . . H1B H 0.2357 0.5711 -0.0508 0.040 Uiso 1 1 calc R . . C2 C 0.2285(2) 0.7082(2) -0.0829(2) 0.0341(8) Uani 1 1 d . . . H2A H 0.1582 0.7071 -0.1125 0.041 Uiso 1 1 calc R . . H2B H 0.2392 0.7672 -0.0546 0.041 Uiso 1 1 calc R . . C3 C 0.4988(3) 0.6069(3) 0.0729(2) 0.0405(8) Uani 1 1 d . . . H3A H 0.5662 0.5867 0.0760 0.049 Uiso 1 1 calc R . . C4 C 0.3679(2) 0.6673(2) 0.10501(19) 0.0334(7) Uani 1 1 d . . . H4A H 0.3227 0.6976 0.1324 0.040 Uiso 1 1 calc R . . C5 C 0.3696(3) 0.6473(3) -0.2291(2) 0.0417(8) Uani 1 1 d . . . H5A H 0.3867 0.6079 -0.2683 0.050 Uiso 1 1 calc R . . C6 C 0.3705(3) 0.7608(2) -0.1523(2) 0.0368(8) Uani 1 1 d . . . H6A H 0.3857 0.8169 -0.1250 0.044 Uiso 1 1 calc R . . C7 C 0.8833(2) 0.8711(3) 0.5003(2) 0.0365(8) Uani 1 1 d . . . H7A H 0.8853 0.9369 0.5136 0.044 Uiso 1 1 calc R . . H7B H 0.9369 0.8592 0.4695 0.044 Uiso 1 1 calc R . . C8 C 0.9053(2) 0.8154(3) 0.5770(2) 0.0363(8) Uani 1 1 d . . . H8A H 0.9009 0.7496 0.5637 0.044 Uiso 1 1 calc R . . H8B H 0.9751 0.8282 0.6045 0.044 Uiso 1 1 calc R . . C9 C 0.6255(3) 0.8458(4) 0.4153(2) 0.0637(13) Uani 1 1 d . . . H9A H 0.5556 0.8552 0.4137 0.076 Uiso 1 1 calc R . . C10 C 0.7623(3) 0.7985(2) 0.3844(2) 0.0365(8) Uani 1 1 d . . . H10A H 0.8107 0.7701 0.3589 0.044 Uiso 1 1 calc R . . C11 C 0.7590(3) 0.9135(2) 0.7076(2) 0.0348(7) Uani 1 1 d . . . H11A H 0.7392 0.9621 0.7379 0.042 Uiso 1 1 calc R . . C12 C 0.7666(3) 0.7812(2) 0.6566(2) 0.0344(8) Uani 1 1 d . . . H12A H 0.7555 0.7190 0.6421 0.041 Uiso 1 1 calc R . . C13 C 0.9459(2) 0.9426(2) -0.12115(18) 0.0270(7) Uani 1 1 d . . . C14 C 0.9522(2) 1.0294(2) -0.15575(18) 0.0267(7) Uani 1 1 d . . . H14A H 0.9964 1.0382 -0.1919 0.032 Uiso 1 1 calc R . . C15 C 0.8933(2) 1.1036(2) -0.13698(18) 0.0271(7) Uani 1 1 d . . . C16 C 0.8288(2) 1.0901(2) -0.08193(19) 0.0299(7) Uani 1 1 d . . . H16A H 0.7891 1.1392 -0.0688 0.036 Uiso 1 1 calc R . . C17 C 0.8235(3) 1.0037(2) -0.04664(18) 0.0307(7) Uani 1 1 d . . . C18 C 0.8823(2) 0.9308(2) -0.06555(19) 0.0308(7) Uani 1 1 d . . . H18A H 0.8793 0.8732 -0.0408 0.037 Uiso 1 1 calc R . . C19 C 0.9955(2) 0.8567(2) -0.1468(2) 0.0310(7) Uani 1 1 d . . . C20 C 0.8946(2) 1.1984(2) -0.17678(19) 0.0290(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.03316(16) 0.03805(16) 0.02623(15) -0.00145(10) 0.00805(11) 0.00260(10) S1 0.0469(5) 0.0332(4) 0.0352(5) -0.0009(4) 0.0232(4) -0.0053(4) O1 0.0572(16) 0.0305(13) 0.0679(18) 0.0153(12) 0.0379(14) 0.0135(11) O2 0.0603(16) 0.0286(13) 0.0446(14) 0.0014(11) 0.0290(13) 0.0068(12) O3 0.0533(15) 0.0295(12) 0.0409(13) 0.0051(10) 0.0250(12) -0.0027(11) O4 0.0455(14) 0.0249(12) 0.0584(16) 0.0081(11) 0.0258(13) 0.0057(11) O5 0.149(3) 0.0518(19) 0.110(3) -0.0299(18) 0.106(3) -0.029(2) O6 0.134(3) 0.094(3) 0.147(4) 0.082(3) 0.109(3) 0.054(2) O7 0.058(2) 0.274(6) 0.0481(19) -0.024(3) 0.0247(16) -0.068(3) O8 0.0699(19) 0.0478(16) 0.0374(14) 0.0079(13) 0.0047(14) -0.0130(14) O9 0.0623(18) 0.0515(17) 0.0438(15) 0.0116(14) 0.0092(14) -0.0052(15) O10 0.0594(18) 0.0388(15) 0.0715(19) 0.0031(15) 0.0286(16) 0.0049(14) O11 0.0666(19) 0.0594(19) 0.0522(17) 0.0056(15) 0.0218(16) 0.0106(15) O12 0.0581(17) 0.0414(16) 0.0584(18) -0.0004(13) 0.0267(15) 0.0025(13) O13 0.0570(18) 0.077(2) 0.0542(18) 0.0062(16) 0.0099(16) -0.0124(16) N1 0.0275(14) 0.0381(15) 0.0288(14) 0.0001(12) 0.0088(11) -0.0025(12) N2 0.0335(15) 0.0568(19) 0.0361(16) -0.0130(15) 0.0093(13) 0.0040(14) N3 0.0335(15) 0.0427(16) 0.0309(14) -0.0047(13) 0.0090(12) 0.0002(13) N4 0.0307(14) 0.0304(14) 0.0294(14) -0.0007(11) 0.0081(12) -0.0021(11) N5 0.0523(19) 0.0387(17) 0.0453(18) -0.0104(14) 0.0200(15) -0.0112(14) N6 0.0349(15) 0.0403(17) 0.0336(15) -0.0014(13) 0.0093(13) -0.0052(13) N7 0.0323(15) 0.0450(17) 0.0315(15) -0.0056(13) 0.0086(12) 0.0023(13) N8 0.0372(17) 0.101(3) 0.0456(19) -0.033(2) 0.0055(15) 0.0145(18) N9 0.0395(17) 0.060(2) 0.0314(16) -0.0102(14) 0.0068(13) 0.0053(15) N10 0.0309(14) 0.0322(15) 0.0281(14) -0.0020(12) 0.0073(11) -0.0006(12) N11 0.0383(15) 0.0306(15) 0.0420(16) -0.0069(13) 0.0121(13) -0.0057(12) N12 0.0346(15) 0.0349(15) 0.0338(15) -0.0006(13) 0.0108(12) -0.0007(13) C1 0.0288(16) 0.0410(19) 0.0314(17) 0.0002(15) 0.0081(14) -0.0057(14) C2 0.0265(16) 0.0409(19) 0.0358(18) 0.0007(15) 0.0081(14) 0.0013(14) C3 0.0328(18) 0.054(2) 0.0356(19) -0.0070(17) 0.0075(16) 0.0040(16) C4 0.0337(18) 0.0385(19) 0.0299(17) -0.0055(15) 0.0110(14) 0.0009(15) C5 0.048(2) 0.041(2) 0.040(2) -0.0070(16) 0.0157(17) -0.0036(17) C6 0.0385(19) 0.0372(19) 0.0364(19) -0.0069(15) 0.0116(16) -0.0075(16) C7 0.0290(17) 0.048(2) 0.0342(18) -0.0054(16) 0.0103(14) -0.0030(15) C8 0.0270(17) 0.046(2) 0.0369(19) -0.0046(16) 0.0084(15) 0.0048(15) C9 0.035(2) 0.110(4) 0.045(2) -0.030(3) 0.0033(18) 0.014(2) C10 0.0385(19) 0.043(2) 0.0298(18) -0.0053(15) 0.0108(15) 0.0058(16) C11 0.0399(18) 0.0315(18) 0.0344(18) -0.0038(15) 0.0108(15) -0.0012(15) C12 0.0380(18) 0.0297(17) 0.0367(19) -0.0032(14) 0.0107(16) -0.0056(14) C13 0.0305(16) 0.0262(16) 0.0249(15) -0.0005(13) 0.0067(13) -0.0003(13) C14 0.0310(16) 0.0257(16) 0.0249(15) -0.0005(13) 0.0090(13) -0.0003(13) C15 0.0323(16) 0.0244(16) 0.0256(15) 0.0010(13) 0.0083(13) -0.0013(13) C16 0.0359(17) 0.0238(16) 0.0323(17) 0.0010(13) 0.0121(14) 0.0031(13) C17 0.0385(18) 0.0290(17) 0.0271(16) -0.0003(13) 0.0130(14) -0.0010(14) C18 0.0402(18) 0.0232(16) 0.0309(17) 0.0055(13) 0.0120(14) 0.0021(14) C19 0.0330(17) 0.0266(17) 0.0355(18) 0.0018(14) 0.0118(14) 0.0025(14) C20 0.0326(17) 0.0250(16) 0.0297(17) 0.0013(13) 0.0065(14) -0.0042(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 Cd1 O8 2.288(3) . ? Cd1 N3 2.319(3) . ? Cd1 N9 2.324(3) . ? Cd1 N6 2.334(3) 4_576 ? Cd1 O9 2.334(3) . ? Cd1 N12 2.341(3) 4_575 ? S1 O6 1.409(3) . ? S1 O7 1.413(3) . ? S1 O5 1.415(3) . ? S1 C17 1.770(3) . ? O1 C19 1.221(4) . ? O2 C19 1.303(4) . ? O2 HW 0.93(5) . ? O3 C20 1.267(4) . ? O4 C20 1.239(4) . ? O8 H1W 0.840(18) . ? O8 H2W 0.837(18) . ? O9 H3W 0.838(18) . ? O9 H4W 0.853(18) . ? O10 H5W 0.846(19) . ? O10 H6W 0.836(19) . ? O11 H7W 0.835(19) . ? O12 H9W 0.843(19) . ? O12 H10W 0.850(19) . ? O13 H11W 0.864(18) . ? O13 H12W 0.850(18) . ? N1 C4 1.322(4) . ? N1 N2 1.364(4) . ? N1 C1 1.453(4) . ? N2 C3 1.314(4) . ? N3 C4 1.328(4) . ? N3 C3 1.357(4) . ? N4 C6 1.316(4) . ? N4 N5 1.356(4) . ? N4 C2 1.459(4) . ? N5 C5 1.305(5) . ? N6 C6 1.329(4) . ? N6 C5 1.346(4) . ? N6 Cd1 2.334(3) 4_575 ? N7 C10 1.325(4) . ? N7 N8 1.360(4) . ? N7 C7 1.449(4) . ? N8 C9 1.306(5) . ? N9 C10 1.327(5) . ? N9 C9 1.352(5) . ? N10 C12 1.322(4) . ? N10 N11 1.360(4) . ? N10 C8 1.463(4) . ? N11 C11 1.313(4) . ? N12 C12 1.324(4) . ? N12 C11 1.355(4) . ? N12 Cd1 2.341(3) 4_576 ? C1 C2 1.507(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9300 . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.504(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C18 1.384(4) . ? C13 C14 1.386(4) . ? C13 C19 1.497(4) . ? C14 C15 1.391(4) . ? C14 H14A 0.9300 . ? C15 C16 1.389(4) . ? C15 C20 1.520(4) . ? C16 C17 1.384(4) . ? C16 H16A 0.9300 . ? C17 C18 1.377(4) . ? C18 H18A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O8 Cd1 N3 87.15(10) . . ? O8 Cd1 N9 88.40(11) . . ? N3 Cd1 N9 175.29(11) . . ? O8 Cd1 N6 86.99(11) . 4_576 ? N3 Cd1 N6 90.71(10) . 4_576 ? N9 Cd1 N6 87.50(10) . 4_576 ? O8 Cd1 O9 172.66(10) . . ? N3 Cd1 O9 85.81(10) . . ? N9 Cd1 O9 98.57(11) . . ? N6 Cd1 O9 90.99(10) 4_576 . ? O8 Cd1 N12 90.00(10) . 4_575 ? N3 Cd1 N12 90.31(9) . 4_575 ? N9 Cd1 N12 91.24(10) . 4_575 ? N6 Cd1 N12 176.77(10) 4_576 4_575 ? O9 Cd1 N12 92.14(10) . 4_575 ? O6 S1 O7 112.5(3) . . ? O6 S1 O5 112.1(3) . . ? O7 S1 O5 111.3(3) . . ? O6 S1 C17 107.28(18) . . ? O7 S1 C17 105.16(17) . . ? O5 S1 C17 108.04(16) . . ? C19 O2 HW 111(3) . . ? Cd1 O8 H1W 115(3) . . ? Cd1 O8 H2W 125(3) . . ? H1W O8 H2W 118(3) . . ? Cd1 O9 H3W 114(3) . . ? Cd1 O9 H4W 114(3) . . ? H3W O9 H4W 116(3) . . ? H5W O10 H6W 108(5) . . ? H9W O12 H10W 105(4) . . ? H11W O13 H12W 115(3) . . ? C4 N1 N2 110.1(3) . . ? C4 N1 C1 129.5(3) . . ? N2 N1 C1 120.4(3) . . ? C3 N2 N1 102.2(3) . . ? C4 N3 C3 102.7(3) . . ? C4 N3 Cd1 127.7(2) . . ? C3 N3 Cd1 128.7(2) . . ? C6 N4 N5 109.6(3) . . ? C6 N4 C2 129.4(3) . . ? N5 N4 C2 121.0(3) . . ? C5 N5 N4 102.6(3) . . ? C6 N6 C5 102.2(3) . . ? C6 N6 Cd1 130.2(2) . 4_575 ? C5 N6 Cd1 126.8(2) . 4_575 ? C10 N7 N8 110.1(3) . . ? C10 N7 C7 129.6(3) . . ? N8 N7 C7 120.3(3) . . ? C9 N8 N7 102.1(3) . . ? C10 N9 C9 102.4(3) . . ? C10 N9 Cd1 129.6(2) . . ? C9 N9 Cd1 127.9(3) . . ? C12 N10 N11 109.7(3) . . ? C12 N10 C8 129.4(3) . . ? N11 N10 C8 121.0(3) . . ? C11 N11 N10 102.8(3) . . ? C12 N12 C11 103.0(3) . . ? C12 N12 Cd1 127.6(2) . 4_576 ? C11 N12 Cd1 127.8(2) . 4_576 ? N1 C1 C2 113.4(3) . . ? N1 C1 H1A 108.9 . . ? C2 C1 H1A 108.9 . . ? N1 C1 H1B 108.9 . . ? C2 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? N4 C2 C1 112.8(3) . . ? N4 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? N4 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? N2 C3 N3 114.8(3) . . ? N2 C3 H3A 122.6 . . ? N3 C3 H3A 122.6 . . ? N1 C4 N3 110.2(3) . . ? N1 C4 H4A 124.9 . . ? N3 C4 H4A 124.9 . . ? N5 C5 N6 115.1(3) . . ? N5 C5 H5A 122.5 . . ? N6 C5 H5A 122.5 . . ? N4 C6 N6 110.5(3) . . ? N4 C6 H6A 124.8 . . ? N6 C6 H6A 124.8 . . ? N7 C7 C8 112.9(3) . . ? N7 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? N7 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? N10 C8 C7 113.1(3) . . ? N10 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? N10 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.8 . . ? N8 C9 N9 115.4(3) . . ? N8 C9 H9A 122.3 . . ? N9 C9 H9A 122.3 . . ? N7 C10 N9 110.0(3) . . ? N7 C10 H10A 125.0 . . ? N9 C10 H10A 125.0 . . ? N11 C11 N12 114.2(3) . . ? N11 C11 H11A 122.9 . . ? N12 C11 H11A 122.9 . . ? N10 C12 N12 110.3(3) . . ? N10 C12 H12A 124.8 . . ? N12 C12 H12A 124.8 . . ? C18 C13 C14 119.3(3) . . ? C18 C13 C19 116.8(3) . . ? C14 C13 C19 123.6(3) . . ? C13 C14 C15 120.7(3) . . ? C13 C14 H14A 119.6 . . ? C15 C14 H14A 119.6 . . ? C16 C15 C14 119.2(3) . . ? C16 C15 C20 118.7(3) . . ? C14 C15 C20 122.0(3) . . ? C17 C16 C15 120.0(3) . . ? C17 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C18 C17 C16 120.3(3) . . ? C18 C17 S1 118.9(2) . . ? C16 C17 S1 120.6(2) . . ? C17 C18 C13 120.4(3) . . ? C17 C18 H18A 119.8 . . ? C13 C18 H18A 119.8 . . ? O1 C19 O2 123.4(3) . . ? O1 C19 C13 121.0(3) . . ? O2 C19 C13 115.4(3) . . ? O4 C20 O3 125.0(3) . . ? O4 C20 C15 118.0(3) . . ? O3 C20 C15 117.0(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 N2 C3 0.5(4) . . . . ? C1 N1 N2 C3 -178.9(3) . . . . ? O8 Cd1 N3 C4 -74.7(3) . . . . ? N6 Cd1 N3 C4 12.2(3) 4_576 . . . ? O9 Cd1 N3 C4 103.2(3) . . . . ? N12 Cd1 N3 C4 -164.7(3) 4_575 . . . ? O8 Cd1 N3 C3 92.0(3) . . . . ? N6 Cd1 N3 C3 179.0(3) 4_576 . . . ? O9 Cd1 N3 C3 -90.1(3) . . . . ? N12 Cd1 N3 C3 2.0(3) 4_575 . . . ? C6 N4 N5 C5 0.1(4) . . . . ? C2 N4 N5 C5 -179.3(3) . . . . ? C10 N7 N8 C9 1.0(5) . . . . ? C7 N7 N8 C9 -178.2(4) . . . . ? O8 Cd1 N9 C10 -94.3(3) . . . . ? N6 Cd1 N9 C10 178.6(3) 4_576 . . . ? O9 Cd1 N9 C10 88.0(3) . . . . ? N12 Cd1 N9 C10 -4.4(3) 4_575 . . . ? O8 Cd1 N9 C9 85.8(4) . . . . ? N6 Cd1 N9 C9 -1.3(4) 4_576 . . . ? O9 Cd1 N9 C9 -91.9(4) . . . . ? N12 Cd1 N9 C9 175.8(4) 4_575 . . . ? C12 N10 N11 C11 0.5(3) . . . . ? C8 N10 N11 C11 179.4(3) . . . . ? C4 N1 C1 C2 96.2(4) . . . . ? N2 N1 C1 C2 -84.5(4) . . . . ? C6 N4 C2 C1 -118.1(4) . . . . ? N5 N4 C2 C1 61.2(4) . . . . ? N1 C1 C2 N4 65.4(4) . . . . ? N1 N2 C3 N3 -0.7(4) . . . . ? C4 N3 C3 N2 0.7(4) . . . . ? Cd1 N3 C3 N2 -168.6(2) . . . . ? N2 N1 C4 N3 -0.1(4) . . . . ? C1 N1 C4 N3 179.2(3) . . . . ? C3 N3 C4 N1 -0.3(4) . . . . ? Cd1 N3 C4 N1 169.1(2) . . . . ? N4 N5 C5 N6 -0.1(4) . . . . ? C6 N6 C5 N5 0.1(4) . . . . ? Cd1 N6 C5 N5 171.1(2) 4_575 . . . ? N5 N4 C6 N6 0.0(4) . . . . ? C2 N4 C6 N6 179.3(3) . . . . ? C5 N6 C6 N4 -0.1(4) . . . . ? Cd1 N6 C6 N4 -170.6(2) 4_575 . . . ? C10 N7 C7 C8 -103.6(4) . . . . ? N8 N7 C7 C8 75.5(4) . . . . ? C12 N10 C8 C7 115.7(4) . . . . ? N11 N10 C8 C7 -62.9(4) . . . . ? N7 C7 C8 N10 -64.7(4) . . . . ? N7 N8 C9 N9 -0.9(6) . . . . ? C10 N9 C9 N8 0.4(6) . . . . ? Cd1 N9 C9 N8 -179.7(3) . . . . ? N8 N7 C10 N9 -0.9(4) . . . . ? C7 N7 C10 N9 178.3(3) . . . . ? C9 N9 C10 N7 0.3(4) . . . . ? Cd1 N9 C10 N7 -179.6(2) . . . . ? N10 N11 C11 N12 -0.6(4) . . . . ? C12 N12 C11 N11 0.4(4) . . . . ? Cd1 N12 C11 N11 -166.1(2) 4_576 . . . ? N11 N10 C12 N12 -0.4(4) . . . . ? C8 N10 C12 N12 -179.1(3) . . . . ? C11 N12 C12 N10 0.0(4) . . . . ? Cd1 N12 C12 N10 166.6(2) 4_576 . . . ? C18 C13 C14 C15 -1.9(5) . . . . ? C19 C13 C14 C15 171.2(3) . . . . ? C13 C14 C15 C16 1.0(5) . . . . ? C13 C14 C15 C20 -177.1(3) . . . . ? C14 C15 C16 C17 -0.2(5) . . . . ? C20 C15 C16 C17 178.0(3) . . . . ? C15 C16 C17 C18 0.3(5) . . . . ? C15 C16 C17 S1 -174.3(2) . . . . ? O6 S1 C17 C18 24.8(4) . . . . ? O7 S1 C17 C18 -95.2(4) . . . . ? O5 S1 C17 C18 145.8(3) . . . . ? O6 S1 C17 C16 -160.5(3) . . . . ? O7 S1 C17 C16 79.5(4) . . . . ? O5 S1 C17 C16 -39.5(4) . . . . ? C16 C17 C18 C13 -1.2(5) . . . . ? S1 C17 C18 C13 173.5(2) . . . . ? C14 C13 C18 C17 2.0(5) . . . . ? C19 C13 C18 C17 -171.6(3) . . . . ? C18 C13 C19 O1 -7.4(5) . . . . ? C14 C13 C19 O1 179.4(3) . . . . ? C18 C13 C19 O2 168.4(3) . . . . ? C14 C13 C19 O2 -4.8(5) . . . . ? C16 C15 C20 O4 6.8(4) . . . . ? C14 C15 C20 O4 -175.1(3) . . . . ? C16 C15 C20 O3 -173.4(3) . . . . ? C14 C15 C20 O3 4.7(5) . . . . ? 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 O2 HW O3 0.93(5) 1.62(5) 2.539(3) 170(5) 2_744 O8 H1W O13 0.840(18) 1.86(2) 2.693(4) 174(4) . O8 H2W O11 0.837(18) 1.90(2) 2.724(4) 170(4) 4_586 O9 H3W O11 0.838(18) 2.113(19) 2.945(4) 172(4) 3_675 O9 H4W O7 0.853(18) 1.89(2) 2.722(4) 166(4) 4_576 O10 H5W O4 0.846(19) 1.96(2) 2.790(4) 166(4) . O10 H6W O12 0.836(19) 2.05(2) 2.881(4) 173(5) . O11 H7W O10 0.835(19) 2.35(5) 2.761(4) 111(4) . O12 H9W N11 0.843(19) 2.14(2) 2.983(4) 176(4) 2_755 O12 H10W O3 0.850(19) 2.17(2) 3.006(4) 168(4) 2_754 O13 H11W O7 0.864(18) 2.04(3) 2.832(5) 153(4) . O13 H12W O7 0.850(18) 2.39(3) 3.150(7) 150(4) 3_675 O13 H12W O5 0.850(18) 2.43(3) 3.209(6) 152(4) 3_675 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.580 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 968328' ####################################################################### # # 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_Cdbte-1,4-bdc _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 Cd N3 O7' _chemical_formula_weight 412.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5996(10) _cell_length_b 9.7638(14) _cell_length_c 9.8660(17) _cell_angle_alpha 88.150(17) _cell_angle_beta 77.431(15) _cell_angle_gamma 64.293(10) _cell_volume 811.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3132 _cell_measurement_theta_min 3.0312 _cell_measurement_theta_max 25.3491 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.689 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 410 _exptl_absorpt_coefficient_mu 1.381 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4448 _exptl_absorpt_correction_T_max 0.7891 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7857 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2951 _reflns_number_gt 2765 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _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^)+(0.0744P)^2^+1.3229P] 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 0.015(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2951 _refine_ls_number_parameters 224 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1151 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.084 _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 0.04806(3) 0.77333(3) 0.97169(3) 0.02741(18) Uani 1 1 d . . . O1 O 0.1206(5) 0.6954(5) 0.7309(4) 0.0525(10) Uani 1 1 d . . . O2 O -0.0576(4) 0.6355(4) 0.8605(3) 0.0386(8) Uani 1 1 d . . . O3 O -0.1146(4) 1.0159(4) 0.9033(4) 0.0369(8) Uani 1 1 d . . . O4 O -0.2723(4) 1.1992(4) 1.0643(4) 0.0452(9) Uani 1 1 d . . . N1 N -0.3200(5) 0.8785(5) 1.3659(4) 0.0365(9) Uani 1 1 d . . . N2 N -0.3516(5) 0.7803(5) 1.2994(4) 0.0403(10) Uani 1 1 d . . . N3 N -0.1453(5) 0.8079(5) 1.1695(4) 0.0333(9) Uani 1 1 d . . . C1 C -0.4161(6) 0.9480(7) 1.5035(5) 0.0440(12) Uani 1 1 d . . . H1A H -0.3705 1.0055 1.5409 0.053 Uiso 1 1 calc R . . H1B H -0.4156 0.8688 1.5655 0.053 Uiso 1 1 calc R . . C2 C -0.2422(6) 0.7410(6) 1.1825(5) 0.0367(11) Uani 1 1 d . . . H2A H -0.2333 0.6721 1.1144 0.044 Uiso 1 1 calc R . . C3 C -0.1975(6) 0.8943(6) 1.2870(5) 0.0371(11) Uani 1 1 d . . . H3A H -0.1547 0.9568 1.3108 0.045 Uiso 1 1 calc R . . C4 C 0.0123(6) 0.5657(5) 0.6179(5) 0.0329(10) Uani 1 1 d . . . C5 C -0.1225(7) 0.5493(7) 0.6160(5) 0.0439(13) Uani 1 1 d . . . H5A H -0.2064 0.5833 0.6939 0.053 Uiso 1 1 calc R . . C6 C -0.1354(7) 0.4829(7) 0.5001(5) 0.0471(13) Uani 1 1 d . . . H6A H -0.2267 0.4710 0.5014 0.057 Uiso 1 1 calc R . . C7 C 0.0253(6) 0.6362(6) 0.7439(5) 0.0361(11) Uani 1 1 d . . . C8 C -0.3793(5) 1.0457(5) 0.9895(5) 0.0291(9) Uani 1 1 d . . . C9 C -0.3703(5) 0.9450(5) 0.8885(5) 0.0312(10) Uani 1 1 d . . . H9A H -0.2832 0.9080 0.8133 0.037 Uiso 1 1 calc R . . C10 C -0.4878(6) 0.8996(5) 0.8982(5) 0.0314(10) Uani 1 1 d . . . H10A H -0.4798 0.8317 0.8296 0.038 Uiso 1 1 calc R . . C11 C -0.2477(6) 1.0905(5) 0.9843(5) 0.0317(10) Uani 1 1 d . . . O5 O 0.2045(5) 0.5394(5) 1.0370(5) 0.0476(9) Uani 1 1 d D . . H1W H 0.143(6) 0.502(7) 1.084(6) 0.057 Uiso 1 1 d D . . H2W H 0.279(6) 0.529(7) 1.078(6) 0.057 Uiso 1 1 d D . . O6 O 0.4466(9) 0.4828(11) 1.1580(12) 0.072(3) Uani 0.50 1 d P . . O7 O 0.1263(14) 0.9640(16) 0.3927(9) 0.088(4) Uani 0.50 1 d P . . O8 O 0.3945(14) 0.6949(16) 0.3478(15) 0.118(6) Uani 0.50 1 d P . . O9 O 0.4260(16) 0.6952(18) 0.6231(15) 0.118(6) Uani 0.50 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 0.0253(2) 0.0360(3) 0.0248(2) -0.00727(14) -0.00103(14) -0.01837(17) O1 0.070(3) 0.076(3) 0.034(2) -0.0108(18) -0.0075(18) -0.054(2) O2 0.045(2) 0.050(2) 0.0260(18) -0.0091(14) -0.0069(15) -0.0243(17) O3 0.0254(17) 0.047(2) 0.043(2) 0.0068(16) -0.0072(15) -0.0202(15) O4 0.0345(19) 0.047(2) 0.064(3) -0.0096(18) -0.0094(17) -0.0266(17) N1 0.034(2) 0.047(2) 0.025(2) -0.0075(17) 0.0038(16) -0.0186(19) N2 0.040(2) 0.044(2) 0.037(2) -0.0070(18) 0.0038(18) -0.023(2) N3 0.030(2) 0.041(2) 0.027(2) -0.0049(16) 0.0012(16) -0.0167(17) C1 0.040(3) 0.060(3) 0.023(2) -0.013(2) 0.005(2) -0.019(3) C2 0.040(3) 0.039(3) 0.028(2) -0.009(2) 0.003(2) -0.020(2) C3 0.034(3) 0.048(3) 0.031(2) -0.010(2) 0.002(2) -0.022(2) C4 0.038(3) 0.039(2) 0.025(2) -0.0043(19) -0.0082(19) -0.020(2) C5 0.043(3) 0.068(4) 0.026(2) -0.013(2) -0.001(2) -0.032(3) C6 0.042(3) 0.074(4) 0.034(3) -0.013(3) -0.004(2) -0.035(3) C7 0.045(3) 0.036(2) 0.029(3) -0.0034(19) -0.012(2) -0.017(2) C8 0.027(2) 0.031(2) 0.036(2) 0.0037(18) -0.0119(18) -0.0169(18) C9 0.024(2) 0.034(2) 0.035(2) -0.0039(19) -0.0026(18) -0.0141(19) C10 0.031(2) 0.034(2) 0.034(2) -0.0075(18) -0.0086(19) -0.018(2) C11 0.031(2) 0.035(2) 0.038(3) 0.007(2) -0.015(2) -0.020(2) O5 0.044(2) 0.042(2) 0.057(3) 0.0085(18) -0.0134(19) -0.0184(18) O6 0.025(4) 0.069(6) 0.108(8) -0.035(5) -0.027(5) -0.001(4) O7 0.088(8) 0.166(12) 0.034(5) 0.026(6) -0.022(5) -0.075(8) O8 0.086(8) 0.135(11) 0.149(11) -0.082(9) 0.060(8) -0.097(9) O9 0.097(9) 0.141(12) 0.117(11) -0.048(9) 0.061(8) -0.088(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 Cd1 O4 2.235(3) 2_577 ? Cd1 O5 2.289(4) . ? Cd1 N3 2.301(4) . ? Cd1 O1 2.376(4) . ? Cd1 O3 2.377(4) . ? Cd1 O2 2.410(3) . ? Cd1 C7 2.748(5) . ? O1 C7 1.261(6) . ? O2 C7 1.250(6) . ? O3 C11 1.260(6) . ? O4 C11 1.250(6) . ? O4 Cd1 2.235(3) 2_577 ? N1 C3 1.328(6) . ? N1 N2 1.349(6) . ? N1 C1 1.458(6) . ? N2 C2 1.316(6) . ? N3 C3 1.322(6) . ? N3 C2 1.333(6) . ? C1 C1 1.502(11) 2_478 ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9300 . ? C3 H3A 0.9300 . ? C4 C5 1.374(7) . ? C4 C6 1.389(7) 2_566 ? C4 C7 1.495(6) . ? C5 C6 1.387(7) . ? C5 H5A 0.9300 . ? C6 C4 1.389(7) 2_566 ? C6 H6A 0.9300 . ? C8 C9 1.385(7) . ? C8 C10 1.405(7) 2_477 ? C8 C11 1.496(6) . ? C9 C10 1.365(6) . ? C9 H9A 0.9300 . ? C10 C8 1.405(7) 2_477 ? C10 H10A 0.9300 . ? O5 H1W 0.868(19) . ? O5 H2W 0.862(19) . ? 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 O5 82.69(15) 2_577 . ? O4 Cd1 N3 131.83(14) 2_577 . ? O5 Cd1 N3 90.01(15) . . ? O4 Cd1 O1 86.42(14) 2_577 . ? O5 Cd1 O1 94.79(16) . . ? N3 Cd1 O1 141.73(14) . . ? O4 Cd1 O3 97.39(13) 2_577 . ? O5 Cd1 O3 179.85(13) . . ? N3 Cd1 O3 90.04(13) . . ? O1 Cd1 O3 85.09(15) . . ? O4 Cd1 O2 137.33(13) 2_577 . ? O5 Cd1 O2 84.55(14) . . ? N3 Cd1 O2 88.57(13) . . ? O1 Cd1 O2 54.32(13) . . ? O3 Cd1 O2 95.31(13) . . ? O4 Cd1 C7 112.46(15) 2_577 . ? O5 Cd1 C7 90.02(15) . . ? N3 Cd1 C7 115.09(15) . . ? O1 Cd1 C7 27.28(14) . . ? O3 Cd1 C7 89.83(14) . . ? O2 Cd1 C7 27.05(14) . . ? C7 O1 Cd1 93.0(3) . . ? C7 O2 Cd1 91.7(3) . . ? C11 O3 Cd1 116.5(3) . . ? C11 O4 Cd1 107.5(3) . 2_577 ? C3 N1 N2 109.5(4) . . ? C3 N1 C1 130.6(5) . . ? N2 N1 C1 119.9(4) . . ? C2 N2 N1 102.7(4) . . ? C3 N3 C2 103.3(4) . . ? C3 N3 Cd1 133.9(3) . . ? C2 N3 Cd1 122.7(3) . . ? N1 C1 C1 111.0(5) . 2_478 ? N1 C1 H1A 109.4 . . ? C1 C1 H1A 109.4 2_478 . ? N1 C1 H1B 109.4 . . ? C1 C1 H1B 109.4 2_478 . ? H1A C1 H1B 108.0 . . ? N2 C2 N3 114.6(4) . . ? N2 C2 H2A 122.7 . . ? N3 C2 H2A 122.7 . . ? N3 C3 N1 109.9(4) . . ? N3 C3 H3A 125.0 . . ? N1 C3 H3A 125.0 . . ? C5 C4 C6 118.8(4) . 2_566 ? C5 C4 C7 120.7(5) . . ? C6 C4 C7 120.6(5) 2_566 . ? C4 C5 C6 121.2(5) . . ? C4 C5 H5A 119.4 . . ? C6 C5 H5A 119.4 . . ? C5 C6 C4 120.0(5) . 2_566 ? C5 C6 H6A 120.0 . . ? C4 C6 H6A 120.0 2_566 . ? O2 C7 O1 120.9(4) . . ? O2 C7 C4 119.8(5) . . ? O1 C7 C4 119.3(5) . . ? O2 C7 Cd1 61.2(2) . . ? O1 C7 Cd1 59.7(2) . . ? C4 C7 Cd1 178.4(4) . . ? C9 C8 C10 118.5(4) . 2_477 ? C9 C8 C11 121.4(4) . . ? C10 C8 C11 120.0(4) 2_477 . ? C10 C9 C8 120.7(4) . . ? C10 C9 H9A 119.6 . . ? C8 C9 H9A 119.6 . . ? C9 C10 C8 120.7(4) . 2_477 ? C9 C10 H10A 119.6 . . ? C8 C10 H10A 119.6 2_477 . ? O4 C11 O3 121.7(4) . . ? O4 C11 C8 118.4(4) . . ? O3 C11 C8 119.8(4) . . ? Cd1 O5 H1W 108(4) . . ? Cd1 O5 H2W 120(4) . . ? H1W O5 H2W 112(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Cd1 O1 C7 163.1(3) 2_577 . . . ? O5 Cd1 O1 C7 80.7(3) . . . . ? N3 Cd1 O1 C7 -15.4(5) . . . . ? O3 Cd1 O1 C7 -99.2(3) . . . . ? O2 Cd1 O1 C7 0.9(3) . . . . ? O4 Cd1 O2 C7 -27.8(4) 2_577 . . . ? O5 Cd1 O2 C7 -100.8(3) . . . . ? N3 Cd1 O2 C7 169.0(3) . . . . ? O1 Cd1 O2 C7 -0.9(3) . . . . ? O3 Cd1 O2 C7 79.1(3) . . . . ? O4 Cd1 O3 C11 -132.1(3) 2_577 . . . ? N3 Cd1 O3 C11 0.2(3) . . . . ? O1 Cd1 O3 C11 142.1(3) . . . . ? O2 Cd1 O3 C11 88.7(3) . . . . ? C7 Cd1 O3 C11 115.2(3) . . . . ? C3 N1 N2 C2 0.7(6) . . . . ? C1 N1 N2 C2 -179.3(5) . . . . ? O4 Cd1 N3 C3 27.0(6) 2_577 . . . ? O5 Cd1 N3 C3 107.2(5) . . . . ? O1 Cd1 N3 C3 -155.1(4) . . . . ? O3 Cd1 N3 C3 -73.0(5) . . . . ? O2 Cd1 N3 C3 -168.3(5) . . . . ? C7 Cd1 N3 C3 -162.8(5) . . . . ? O4 Cd1 N3 C2 -157.5(4) 2_577 . . . ? O5 Cd1 N3 C2 -77.4(4) . . . . ? O1 Cd1 N3 C2 20.4(5) . . . . ? O3 Cd1 N3 C2 102.5(4) . . . . ? O2 Cd1 N3 C2 7.2(4) . . . . ? C7 Cd1 N3 C2 12.7(4) . . . . ? C3 N1 C1 C1 114.2(7) . . . 2_478 ? N2 N1 C1 C1 -65.8(8) . . . 2_478 ? N1 N2 C2 N3 -0.6(6) . . . . ? C3 N3 C2 N2 0.4(6) . . . . ? Cd1 N3 C2 N2 -176.3(3) . . . . ? C2 N3 C3 N1 0.1(6) . . . . ? Cd1 N3 C3 N1 176.2(3) . . . . ? N2 N1 C3 N3 -0.5(6) . . . . ? C1 N1 C3 N3 179.5(5) . . . . ? C7 C4 C5 C6 -179.5(5) . . . . ? Cd1 O2 C7 O1 1.7(5) . . . . ? Cd1 O2 C7 C4 -178.5(4) . . . . ? Cd1 O1 C7 O2 -1.7(5) . . . . ? Cd1 O1 C7 C4 178.5(4) . . . . ? C5 C4 C7 O2 23.3(8) . . . . ? C6 C4 C7 O2 -157.4(5) 2_566 . . . ? C5 C4 C7 O1 -156.9(5) . . . . ? C6 C4 C7 O1 22.4(8) 2_566 . . . ? O4 Cd1 C7 O2 160.0(3) 2_577 . . . ? O5 Cd1 C7 O2 77.9(3) . . . . ? N3 Cd1 C7 O2 -12.1(3) . . . . ? O1 Cd1 C7 O2 178.3(5) . . . . ? O3 Cd1 C7 O2 -102.1(3) . . . . ? O4 Cd1 C7 O1 -18.4(4) 2_577 . . . ? O5 Cd1 C7 O1 -100.4(3) . . . . ? N3 Cd1 C7 O1 169.5(3) . . . . ? O3 Cd1 C7 O1 79.6(3) . . . . ? O2 Cd1 C7 O1 -178.3(5) . . . . ? C10 C8 C9 C10 -0.2(8) 2_477 . . . ? C11 C8 C9 C10 176.9(4) . . . . ? C8 C9 C10 C8 0.2(8) . . . 2_477 ? Cd1 O4 C11 O3 0.9(5) 2_577 . . . ? Cd1 O4 C11 C8 178.8(3) 2_577 . . . ? Cd1 O3 C11 O4 102.7(5) . . . . ? Cd1 O3 C11 C8 -75.1(5) . . . . ? C9 C8 C11 O4 168.7(4) . . . . ? C10 C8 C11 O4 -14.4(7) 2_477 . . . ? C9 C8 C11 O3 -13.4(7) . . . . ? C10 C8 C11 O3 163.5(4) 2_477 . . . ? 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 O5 H1W O2 0.868(19) 1.87(3) 2.699(5) 160(7) 2_567 O5 H2W O6 0.862(19) 1.82(2) 2.680(9) 174(7) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.735 _refine_diff_density_min -0.874 _refine_diff_density_rms 0.132 _database_code_depnum_ccdc_archive 'CCDC 968329' ####################################################################### # # 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_Cdbtebtec _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H44 Cd2 N12 O21' _chemical_formula_weight 1037.49 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 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 11.014(2) _cell_length_b 10.8512(18) _cell_length_c 17.237(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.171(5) _cell_angle_gamma 90.00 _cell_volume 1978.5(6) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 8333 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.742 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 1.168 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6522 _exptl_absorpt_correction_T_max 0.7207 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.63 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10492 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4489 _reflns_number_gt 3635 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _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^)+(0.0767P)^2^+2.4137P] 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 0.0033(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4489 _refine_ls_number_parameters 290 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1434 _refine_ls_wR_factor_gt 0.1328 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 0.37870(3) 0.18550(3) 0.184434(18) 0.02859(16) Uani 1 1 d . . . O1 O 0.5105(3) 0.0557(4) 0.2916(2) 0.0419(9) Uani 1 1 d . . . O2 O 0.3203(3) 0.1055(3) 0.29859(19) 0.0361(8) Uani 1 1 d . . . O3 O 0.3126(4) -0.1805(3) 0.3273(2) 0.0428(9) Uani 1 1 d . . . O4 O 0.2116(3) -0.1802(3) 0.4212(2) 0.0414(9) Uani 1 1 d . . . O5 O 0.4963(5) 0.3321(4) 0.2691(3) 0.0558(11) Uani 1 1 d D . . H1W H 0.486(7) 0.397(4) 0.239(4) 0.067 Uiso 1 1 d D . . H2W H 0.558(4) 0.324(6) 0.311(3) 0.067 Uiso 1 1 d D . . O6 O 0.5673(6) 0.5488(6) 0.2331(3) 0.0829(16) Uani 1 1 d D . . H3W H 0.633(6) 0.543(9) 0.212(5) 0.099 Uiso 1 1 d D . . O7 O 0.7506(5) 0.2979(6) 0.3700(3) 0.0716(15) Uani 1 1 d D . . H5W H 0.780(7) 0.229(3) 0.357(5) 0.086 Uiso 1 1 d D . . H6W H 0.761(5) 0.360(4) 0.341(4) 0.086 Uiso 1 1 d D . . O8 O 0.4350(6) 0.1501(7) -0.2046(5) 0.099(2) Uani 1 1 d D . . H7W H 0.500(6) 0.185(7) -0.170(5) 0.119 Uiso 1 1 d D . . H8W H 0.458(7) 0.083(5) -0.224(5) 0.119 Uiso 1 1 d D . . O9 O 0.6277(5) 0.3196(5) -0.1370(4) 0.0779(16) Uani 1 1 d D . . H9W H 0.587(6) 0.377(6) -0.172(4) 0.094 Uiso 1 1 d D . . H10W H 0.703(4) 0.307(7) -0.144(5) 0.094 Uiso 1 1 d D . . O10 O 0.7346(5) 0.5414(8) 0.1445(4) 0.079(2) Uani 0.75 1 d P . . O11 O 0.3781(5) 0.5074(6) 0.0087(4) 0.0648(17) Uani 0.75 1 d P . . N1 N 0.1376(4) -0.0653(4) 0.0026(2) 0.0336(9) Uani 1 1 d . . . N2 N 0.1311(4) -0.1331(4) 0.0687(3) 0.0394(10) Uani 1 1 d . . . N3 N 0.2538(4) 0.0349(4) 0.1059(2) 0.0334(9) Uani 1 1 d . . . N4 N 0.2813(4) -0.2037(4) -0.0911(3) 0.0345(9) Uani 1 1 d . . . N5 N 0.3688(4) -0.1943(5) -0.0190(3) 0.0460(12) Uani 1 1 d . . . N6 N 0.4590(4) -0.1745(4) -0.1206(3) 0.0370(10) Uani 1 1 d . . . C1 C 0.0827(5) -0.1119(5) -0.0791(3) 0.0408(12) Uani 1 1 d . . . H1A H 0.0891 -0.0482 -0.1181 0.049 Uiso 1 1 calc R . . H1B H -0.0071 -0.1293 -0.0867 0.049 Uiso 1 1 calc R . . C2 C 0.1477(5) -0.2277(5) -0.0957(3) 0.0421(12) Uani 1 1 d . . . H2A H 0.1431 -0.2911 -0.0561 0.050 Uiso 1 1 calc R . . H2B H 0.1039 -0.2589 -0.1495 0.050 Uiso 1 1 calc R . . C3 C 0.2018(5) -0.0676(5) 0.1287(3) 0.0383(11) Uani 1 1 d . . . H3A H 0.2153 -0.0901 0.1831 0.046 Uiso 1 1 calc R . . C4 C 0.2119(4) 0.0325(5) 0.0259(3) 0.0328(10) Uani 1 1 d . . . H4A H 0.2316 0.0910 -0.0090 0.039 Uiso 1 1 calc R . . C5 C 0.4731(5) -0.1766(6) -0.0399(3) 0.0505(16) Uani 1 1 d . . . H5A H 0.5520 -0.1662 -0.0018 0.061 Uiso 1 1 calc R . . C6 C 0.3354(5) -0.1923(5) -0.1503(3) 0.0399(12) Uani 1 1 d . . . H6A H 0.2924 -0.1963 -0.2056 0.048 Uiso 1 1 calc R . . C7 C 0.4650(4) 0.0253(4) 0.4171(2) 0.0256(9) Uani 1 1 d . . . C8 C 0.4019(4) -0.0673(4) 0.4481(3) 0.0267(9) Uani 1 1 d . . . C9 C 0.4375(4) -0.0911(4) 0.5303(3) 0.0283(9) Uani 1 1 d . . . H9A H 0.3952 -0.1528 0.5510 0.034 Uiso 1 1 calc R . . C10 C 0.4276(4) 0.0618(4) 0.3296(3) 0.0310(10) Uani 1 1 d . . . C11 C 0.3021(4) -0.1473(5) 0.3938(3) 0.0319(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.0259(2) 0.0387(2) 0.0196(2) 0.00305(13) 0.00381(13) 0.00369(14) O1 0.0363(18) 0.066(2) 0.0239(17) 0.0049(17) 0.0098(14) 0.0047(18) O2 0.0305(16) 0.052(2) 0.0227(16) 0.0086(15) 0.0012(13) 0.0037(15) O3 0.049(2) 0.049(2) 0.0254(18) -0.0069(15) 0.0026(16) -0.0121(17) O4 0.0361(19) 0.050(2) 0.036(2) -0.0089(16) 0.0078(16) -0.0141(16) O5 0.048(2) 0.066(3) 0.050(3) -0.020(2) 0.009(2) -0.007(2) O6 0.093(4) 0.089(4) 0.067(3) 0.003(3) 0.024(3) -0.012(4) O7 0.057(3) 0.105(4) 0.054(3) -0.006(3) 0.016(2) -0.009(3) O8 0.095(4) 0.093(5) 0.120(6) -0.035(4) 0.048(4) 0.002(4) O9 0.061(3) 0.089(4) 0.092(4) 0.020(3) 0.035(3) 0.009(3) O10 0.034(3) 0.144(7) 0.061(4) -0.002(4) 0.018(3) -0.001(4) O11 0.044(3) 0.074(4) 0.082(5) 0.007(3) 0.027(3) -0.015(3) N1 0.0289(19) 0.042(2) 0.030(2) -0.0028(18) 0.0090(16) 0.0023(18) N2 0.039(2) 0.044(2) 0.038(2) 0.002(2) 0.0158(19) -0.007(2) N3 0.0284(19) 0.042(2) 0.029(2) -0.0013(17) 0.0061(16) 0.0021(18) N4 0.029(2) 0.047(2) 0.029(2) -0.0055(17) 0.0098(16) -0.0012(18) N5 0.030(2) 0.081(4) 0.028(2) 0.000(2) 0.0092(18) 0.003(2) N6 0.029(2) 0.054(3) 0.028(2) 0.0047(18) 0.0076(17) 0.0040(19) C1 0.028(2) 0.058(3) 0.033(3) -0.014(2) 0.003(2) -0.001(2) C2 0.034(3) 0.052(3) 0.042(3) -0.017(2) 0.014(2) -0.009(2) C3 0.038(3) 0.050(3) 0.027(2) 0.002(2) 0.010(2) -0.002(2) C4 0.029(2) 0.040(3) 0.028(2) -0.0029(19) 0.0054(18) -0.001(2) C5 0.029(3) 0.089(5) 0.033(3) 0.003(3) 0.007(2) 0.004(3) C6 0.034(2) 0.063(4) 0.023(2) -0.004(2) 0.008(2) 0.000(2) C7 0.025(2) 0.034(2) 0.0160(19) 0.0004(16) 0.0028(15) 0.0027(18) C8 0.0231(19) 0.035(2) 0.021(2) -0.0015(18) 0.0030(16) 0.0002(18) C9 0.027(2) 0.033(2) 0.022(2) 0.0036(17) 0.0042(17) -0.0007(19) C10 0.034(2) 0.035(2) 0.021(2) -0.0009(18) 0.0015(18) -0.002(2) C11 0.030(2) 0.033(2) 0.026(2) 0.0029(19) -0.0024(18) -0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O5 2.299(4) . ? Cd1 N3 2.315(4) . ? Cd1 O4 2.328(3) 2 ? Cd1 N6 2.349(4) 3_655 ? Cd1 O2 2.397(3) . ? Cd1 O1 2.452(4) . ? Cd1 O3 2.521(4) 2 ? O1 C10 1.264(6) . ? O2 C10 1.247(5) . ? O3 C11 1.237(6) . ? O3 Cd1 2.521(4) 2_545 ? O4 C11 1.268(6) . ? O4 Cd1 2.328(3) 2_545 ? O5 H1W 0.86(2) . ? O5 H2W 0.84(2) . ? O6 H3W 0.90(2) . ? O7 H5W 0.86(2) . ? O7 H6W 0.86(2) . ? O8 H7W 0.88(2) . ? O8 H8W 0.87(2) . ? O9 H9W 0.89(2) . ? O9 H10W 0.87(2) . ? N1 C4 1.332(6) . ? N1 N2 1.375(6) . ? N1 C1 1.458(6) . ? N2 C3 1.317(7) . ? N3 C4 1.327(6) . ? N3 C3 1.358(7) . ? N4 C6 1.322(7) . ? N4 N5 1.349(6) . ? N4 C2 1.474(6) . ? N5 C5 1.310(7) . ? N6 C6 1.329(7) . ? N6 C5 1.355(7) . ? N6 Cd1 2.349(4) 3_655 ? C1 C2 1.513(8) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9400 . ? C4 H4A 0.9400 . ? C5 H5A 0.9400 . ? C6 H6A 0.9400 . ? C7 C9 1.394(6) 3_656 ? C7 C8 1.409(6) . ? C7 C10 1.501(6) . ? C8 C9 1.385(6) . ? C8 C11 1.506(6) . ? C9 C7 1.394(6) 3_656 ? C9 H9A 0.9400 . ? 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 O5 Cd1 N3 176.15(16) . . ? O5 Cd1 O4 96.08(17) . 2 ? N3 Cd1 O4 85.95(14) . 2 ? O5 Cd1 N6 87.99(17) . 3_655 ? N3 Cd1 N6 95.51(15) . 3_655 ? O4 Cd1 N6 83.12(14) 2 3_655 ? O5 Cd1 O2 87.83(16) . . ? N3 Cd1 O2 88.43(13) . . ? O4 Cd1 O2 135.67(12) 2 . ? N6 Cd1 O2 141.21(13) 3_655 . ? O5 Cd1 O1 78.97(17) . . ? N3 Cd1 O1 99.54(14) . . ? O4 Cd1 O1 169.53(13) 2 . ? N6 Cd1 O1 87.46(13) 3_655 . ? O2 Cd1 O1 53.91(11) . . ? O5 Cd1 O3 87.83(15) . 2 ? N3 Cd1 O3 90.75(13) . 2 ? O4 Cd1 O3 53.93(13) 2 2 ? N6 Cd1 O3 136.05(14) 3_655 2 ? O2 Cd1 O3 82.27(12) . 2 ? O1 Cd1 O3 134.25(12) . 2 ? C10 O1 Cd1 89.9(3) . . ? C10 O2 Cd1 92.9(3) . . ? C11 O3 Cd1 87.2(3) . 2_545 ? C11 O4 Cd1 95.3(3) . 2_545 ? Cd1 O5 H1W 103(5) . . ? Cd1 O5 H2W 130(5) . . ? H1W O5 H2W 123(7) . . ? H5W O7 H6W 114(4) . . ? H7W O8 H8W 111(3) . . ? H9W O9 H10W 109(3) . . ? C4 N1 N2 110.2(4) . . ? C4 N1 C1 128.5(4) . . ? N2 N1 C1 120.7(4) . . ? C3 N2 N1 101.9(4) . . ? C4 N3 C3 103.5(4) . . ? C4 N3 Cd1 126.8(3) . . ? C3 N3 Cd1 129.7(3) . . ? C6 N4 N5 110.1(4) . . ? C6 N4 C2 129.3(4) . . ? N5 N4 C2 120.6(4) . . ? C5 N5 N4 102.3(4) . . ? C6 N6 C5 101.8(4) . . ? C6 N6 Cd1 130.1(3) . 3_655 ? C5 N6 Cd1 126.5(3) . 3_655 ? N1 C1 C2 112.3(4) . . ? N1 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? N1 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.9 . . ? N4 C2 C1 111.2(4) . . ? N4 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? N4 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? N2 C3 N3 114.8(5) . . ? N2 C3 H3A 122.6 . . ? N3 C3 H3A 122.6 . . ? N3 C4 N1 109.6(4) . . ? N3 C4 H4A 125.2 . . ? N1 C4 H4A 125.2 . . ? N5 C5 N6 115.2(5) . . ? N5 C5 H5A 122.4 . . ? N6 C5 H5A 122.4 . . ? N4 C6 N6 110.5(4) . . ? N4 C6 H6A 124.8 . . ? N6 C6 H6A 124.8 . . ? C9 C7 C8 119.4(4) 3_656 . ? C9 C7 C10 117.6(4) 3_656 . ? C8 C7 C10 122.9(4) . . ? C9 C8 C7 119.6(4) . . ? C9 C8 C11 118.5(4) . . ? C7 C8 C11 121.8(4) . . ? C8 C9 C7 121.1(4) . 3_656 ? C8 C9 H9A 119.5 . . ? C7 C9 H9A 119.5 3_656 . ? O2 C10 O1 122.2(4) . . ? O2 C10 C7 119.5(4) . . ? O1 C10 C7 118.1(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Cd1 O1 C10 89.7(3) . . . . ? N3 Cd1 O1 C10 -86.7(3) . . . . ? O4 Cd1 O1 C10 152.3(6) 2 . . . ? N6 Cd1 O1 C10 178.2(3) 3_655 . . . ? O2 Cd1 O1 C10 -5.7(3) . . . . ? O3 Cd1 O1 C10 13.8(4) 2 . . . ? C11 Cd1 O1 C10 21.9(6) 2 . . . ? O5 Cd1 O2 C10 -72.2(3) . . . . ? N3 Cd1 O2 C10 108.8(3) . . . . ? O4 Cd1 O2 C10 -168.6(3) 2 . . . ? N6 Cd1 O2 C10 11.9(4) 3_655 . . . ? O1 Cd1 O2 C10 5.8(3) . . . . ? O3 Cd1 O2 C10 -160.3(3) 2 . . . ? C11 Cd1 O2 C10 -164.9(3) 2 . . . ? C4 N1 N2 C3 1.3(5) . . . . ? C1 N1 N2 C3 173.2(4) . . . . ? O4 Cd1 N3 C4 27.5(4) 2 . . . ? N6 Cd1 N3 C4 -55.1(4) 3_655 . . . ? O2 Cd1 N3 C4 163.5(4) . . . . ? O1 Cd1 N3 C4 -143.5(4) . . . . ? O3 Cd1 N3 C4 81.3(4) 2 . . . ? C11 Cd1 N3 C4 54.9(4) 2 . . . ? C10 Cd1 N3 C4 -170.9(4) . . . . ? O4 Cd1 N3 C3 -149.5(4) 2 . . . ? N6 Cd1 N3 C3 127.8(4) 3_655 . . . ? O2 Cd1 N3 C3 -13.5(4) . . . . ? O1 Cd1 N3 C3 39.5(4) . . . . ? O3 Cd1 N3 C3 -95.7(4) 2 . . . ? C11 Cd1 N3 C3 -122.2(4) 2 . . . ? C10 Cd1 N3 C3 12.0(4) . . . . ? C6 N4 N5 C5 0.4(6) . . . . ? C2 N4 N5 C5 178.4(5) . . . . ? C4 N1 C1 C2 106.0(6) . . . . ? N2 N1 C1 C2 -64.3(6) . . . . ? C6 N4 C2 C1 -104.3(6) . . . . ? N5 N4 C2 C1 78.0(6) . . . . ? N1 C1 C2 N4 -63.2(6) . . . . ? N1 N2 C3 N3 -0.9(6) . . . . ? C4 N3 C3 N2 0.1(6) . . . . ? Cd1 N3 C3 N2 177.6(3) . . . . ? C3 N3 C4 N1 0.8(5) . . . . ? Cd1 N3 C4 N1 -176.9(3) . . . . ? N2 N1 C4 N3 -1.4(5) . . . . ? C1 N1 C4 N3 -172.5(4) . . . . ? N4 N5 C5 N6 -0.3(7) . . . . ? C6 N6 C5 N5 0.1(7) . . . . ? Cd1 N6 C5 N5 -166.8(4) 3_655 . . . ? N5 N4 C6 N6 -0.4(6) . . . . ? C2 N4 C6 N6 -178.2(5) . . . . ? C5 N6 C6 N4 0.2(6) . . . . ? Cd1 N6 C6 N4 166.4(3) 3_655 . . . ? C10 C7 C8 C9 -176.5(4) . . . . ? C9 C7 C8 C11 -175.7(4) 3_656 . . . ? C10 C7 C8 C11 7.6(7) . . . . ? C7 C8 C9 C7 -0.2(7) . . . 3_656 ? C11 C8 C9 C7 175.8(4) . . . 3_656 ? Cd1 O2 C10 O1 -10.7(5) . . . . ? Cd1 O2 C10 C7 163.6(4) . . . . ? Cd1 O1 C10 O2 10.5(5) . . . . ? Cd1 O1 C10 C7 -164.0(4) . . . . ? C9 C7 C10 O2 -114.7(5) 3_656 . . . ? C8 C7 C10 O2 62.1(6) . . . . ? C9 C7 C10 O1 59.9(6) 3_656 . . . ? C8 C7 C10 O1 -123.3(5) . . . . ? C9 C7 C10 Cd1 -29.8(15) 3_656 . . . ? C8 C7 C10 Cd1 146.9(11) . . . . ? O5 Cd1 C10 O2 105.1(3) . . . . ? N3 Cd1 C10 O2 -72.5(3) . . . . ? O4 Cd1 C10 O2 25.5(6) 2 . . . ? N6 Cd1 C10 O2 -171.8(3) 3_655 . . . ? O1 Cd1 C10 O2 -169.8(5) . . . . ? O3 Cd1 C10 O2 20.5(3) 2 . . . ? C11 Cd1 C10 O2 20.1(4) 2 . . . ? O5 Cd1 C10 O1 -85.1(3) . . . . ? N3 Cd1 C10 O1 97.4(3) . . . . ? O4 Cd1 C10 O1 -164.7(4) 2 . . . ? N6 Cd1 C10 O1 -2.0(3) 3_655 . . . ? O2 Cd1 C10 O1 169.8(5) . . . . ? O3 Cd1 C10 O1 -169.6(3) 2 . . . ? C11 Cd1 C10 O1 -170.1(3) 2 . . . ? O5 Cd1 C10 C7 12.1(13) . . . . ? N3 Cd1 C10 C7 -165.4(13) . . . . ? O4 Cd1 C10 C7 -67.4(15) 2 . . . ? N6 Cd1 C10 C7 95.2(13) 3_655 . . . ? O2 Cd1 C10 C7 -93.0(13) . . . . ? O1 Cd1 C10 C7 97.2(14) . . . . ? O3 Cd1 C10 C7 -72.4(13) 2 . . . ? C11 Cd1 C10 C7 -72.8(13) 2 . . . ? Cd1 O3 C11 O4 -4.7(5) 2_545 . . . ? Cd1 O3 C11 C8 173.2(4) 2_545 . . . ? Cd1 O4 C11 O3 5.1(5) 2_545 . . . ? Cd1 O4 C11 C8 -172.9(3) 2_545 . . . ? C9 C8 C11 O3 -139.8(5) . . . . ? C7 C8 C11 O3 36.1(7) . . . . ? C9 C8 C11 O4 38.2(6) . . . . ? C7 C8 C11 O4 -145.9(5) . . . . ? 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 O5 H1W O6 0.86(2) 1.89(5) 2.606(8) 139(7) . O5 H2W O7 0.84(2) 2.10(4) 2.881(8) 153(7) . O6 H3W O10 0.90(2) 1.83(3) 2.703(8) 165(9) . O7 H5W O10 0.86(2) 2.04(4) 2.803(11) 146(6) 2_645 O7 H6W O8 0.86(2) 2.27(5) 2.748(8) 115(4) 4_666 O8 H7W O9 0.88(2) 2.00(5) 2.805(9) 152(10) . O8 H8W O1 0.87(2) 1.99(3) 2.846(7) 168(9) 3_655 O9 H9W O6 0.89(2) 1.91(4) 2.723(8) 150(7) 3_665 O9 H10W O2 0.87(2) 2.07(5) 2.775(6) 137(6) 4_665 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.321 _refine_diff_density_min -0.761 _refine_diff_density_rms 0.123 _database_code_depnum_ccdc_archive 'CCDC 968330' ####################################################################### # # 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_Cdbtreobc _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 Cd N6 O6 ' _chemical_formula_sum 'C20 H16 Cd N6 O6' _chemical_formula_weight 548.79 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 orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_Int_Tables_number 60 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z' 'x, -y, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z' '-x, y, -z-1/2' 'x-1/2, y-1/2, -z-1/2' _cell_length_a 19.6725(14) _cell_length_b 10.3235(7) _cell_length_c 10.5318(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2138.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 8243 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.704 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 1.072 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6737 _exptl_absorpt_correction_T_max 0.8142 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.63 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11456 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2436 _reflns_number_gt 2217 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _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^)+(0.0533P)^2^+1.6560P] 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 2436 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 0.5000 0.61808(3) 0.2500 0.02153(12) Uani 1 2 d S . . O1 O 0.58309(11) 0.4438(2) 0.22783(19) 0.0300(5) Uani 1 1 d . . . O2 O 0.58662(10) 0.5801(2) 0.38767(19) 0.0299(4) Uani 1 1 d . . . O3 O 0.85837(10) 0.2804(2) 0.50713(19) 0.0320(5) Uani 1 1 d . . . N1 N 0.46336(12) 0.7510(2) 0.4066(2) 0.0262(5) Uani 1 1 d . . . N2 N 0.42796(15) 0.8658(3) 0.3937(3) 0.0380(6) Uani 1 1 d . . . N3 N 0.45603(12) 0.8388(2) 0.5935(2) 0.0249(5) Uani 1 1 d . . . C1 C 0.46221(17) 0.8584(3) 0.7310(3) 0.0295(7) Uani 1 1 d . . . H1A H 0.4383 0.7890 0.7761 0.035 Uiso 1 1 calc R . . H1B H 0.4414 0.9411 0.7548 0.035 Uiso 1 1 calc R . . C2 C 0.47950(15) 0.7375(3) 0.5260(3) 0.0250(5) Uani 1 1 d . . . H2A H 0.5039 0.6674 0.5599 0.030 Uiso 1 1 calc R . . C3 C 0.42472(17) 0.9155(3) 0.5072(3) 0.0356(7) Uani 1 1 d . . . H3A H 0.4034 0.9945 0.5267 0.043 Uiso 1 1 calc R . . C4 C 0.67501(14) 0.4241(3) 0.3749(3) 0.0244(6) Uani 1 1 d . . . C5 C 0.70027(15) 0.4598(3) 0.4935(3) 0.0295(6) Uani 1 1 d . . . H5A H 0.6756 0.5180 0.5444 0.035 Uiso 1 1 calc R . . C6 C 0.76156(16) 0.4100(3) 0.5367(3) 0.0313(6) Uani 1 1 d . . . H6A H 0.7786 0.4347 0.6165 0.038 Uiso 1 1 calc R . . C7 C 0.79747(14) 0.3236(3) 0.4614(3) 0.0270(6) Uani 1 1 d . . . C8 C 0.77221(14) 0.2861(3) 0.3440(3) 0.0305(6) Uani 1 1 d . . . H8A H 0.7966 0.2271 0.2936 0.037 Uiso 1 1 calc R . . C9 C 0.71116(15) 0.3354(3) 0.3016(3) 0.0297(6) Uani 1 1 d . . . H9A H 0.6938 0.3090 0.2226 0.036 Uiso 1 1 calc R . . C10 C 0.61163(13) 0.4842(3) 0.3261(3) 0.0234(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.02230(19) 0.02294(18) 0.01936(18) 0.000 -0.00303(10) 0.000 O1 0.0284(11) 0.0309(11) 0.0308(10) -0.0043(8) -0.0068(9) 0.0044(9) O2 0.0256(10) 0.0289(10) 0.0351(11) -0.0061(9) -0.0047(9) 0.0070(8) O3 0.0261(10) 0.0322(11) 0.0376(11) -0.0041(9) -0.0082(9) 0.0075(8) N1 0.0298(12) 0.0255(12) 0.0232(11) -0.0007(9) -0.0019(10) 0.0045(9) N2 0.0483(17) 0.0365(15) 0.0292(14) 0.0016(11) -0.0044(13) 0.0172(12) N3 0.0318(12) 0.0211(11) 0.0218(11) -0.0013(9) 0.0019(10) 0.0031(9) C1 0.0359(19) 0.0329(15) 0.0195(13) -0.0039(11) 0.0017(12) 0.0038(13) C2 0.0299(13) 0.0204(13) 0.0247(13) 0.0032(10) 0.0019(12) 0.0021(11) C3 0.0439(18) 0.0311(15) 0.0319(16) -0.0019(13) -0.0038(14) 0.0164(14) C4 0.0247(13) 0.0228(13) 0.0258(14) 0.0014(11) -0.0005(11) 0.0027(10) C5 0.0290(15) 0.0310(15) 0.0285(15) -0.0047(12) -0.0007(12) 0.0069(12) C6 0.0350(16) 0.0324(15) 0.0266(14) -0.0038(12) -0.0046(13) 0.0070(12) C7 0.0239(14) 0.0255(14) 0.0317(14) 0.0011(11) -0.0041(12) 0.0022(11) C8 0.0308(15) 0.0311(15) 0.0296(15) -0.0065(12) 0.0005(12) 0.0092(12) C9 0.0323(16) 0.0303(15) 0.0266(14) -0.0049(12) -0.0036(13) 0.0057(12) C10 0.0220(12) 0.0216(13) 0.0267(13) 0.0024(11) 0.0027(11) -0.0013(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 N1 2.263(2) . ? Cd1 N1 2.263(2) 7_656 ? Cd1 O2 2.2715(19) 7_656 ? Cd1 O2 2.2715(19) . ? Cd1 O1 2.442(2) 7_656 ? Cd1 O1 2.442(2) . ? Cd1 C10 2.716(3) 7_656 ? Cd1 C10 2.716(3) . ? O1 C10 1.249(3) . ? O2 C10 1.282(3) . ? O3 C7 1.366(3) . ? N1 C2 1.304(4) . ? N1 N2 1.382(3) . ? N2 C3 1.302(4) . ? N3 C2 1.347(4) . ? N3 C3 1.354(4) . ? N3 C1 1.467(3) . ? C1 C1 1.540(7) 7_657 ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 H2A 0.9400 . ? C3 H3A 0.9400 . ? C4 C9 1.392(4) . ? C4 C5 1.394(4) . ? C4 C10 1.485(4) . ? C5 C6 1.388(4) . ? C5 H5A 0.9400 . ? C6 C7 1.387(4) . ? C6 H6A 0.9400 . ? C7 C8 1.388(4) . ? C8 C9 1.379(4) . ? C8 H8A 0.9400 . ? C9 H9A 0.9400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cd1 N1 105.36(12) . 7_656 ? N1 Cd1 O2 109.31(8) . 7_656 ? N1 Cd1 O2 83.02(7) 7_656 7_656 ? N1 Cd1 O2 83.02(8) . . ? N1 Cd1 O2 109.31(8) 7_656 . ? O2 Cd1 O2 160.14(10) 7_656 . ? N1 Cd1 O1 99.43(8) . 7_656 ? N1 Cd1 O1 136.85(7) 7_656 7_656 ? O2 Cd1 O1 55.38(7) 7_656 7_656 ? O2 Cd1 O1 108.31(7) . 7_656 ? N1 Cd1 O1 136.85(7) . . ? N1 Cd1 O1 99.43(8) 7_656 . ? O2 Cd1 O1 108.31(7) 7_656 . ? O2 Cd1 O1 55.38(7) . . ? O1 Cd1 O1 85.09(11) 7_656 . ? N1 Cd1 C10 105.42(8) . 7_656 ? N1 Cd1 C10 110.55(8) 7_656 7_656 ? O2 Cd1 C10 28.01(8) 7_656 7_656 ? O2 Cd1 C10 135.02(8) . 7_656 ? O1 Cd1 C10 27.38(7) 7_656 7_656 ? O1 Cd1 C10 97.94(7) . 7_656 ? N1 Cd1 C10 110.55(8) . . ? N1 Cd1 C10 105.42(8) 7_656 . ? O2 Cd1 C10 135.02(8) 7_656 . ? O2 Cd1 C10 28.01(8) . . ? O1 Cd1 C10 97.94(7) 7_656 . ? O1 Cd1 C10 27.38(7) . . ? C10 Cd1 C10 118.83(11) 7_656 . ? C10 O1 Cd1 88.60(16) . . ? C10 O2 Cd1 95.64(16) . . ? C2 N1 N2 108.0(2) . . ? C2 N1 Cd1 124.08(19) . . ? N2 N1 Cd1 127.54(18) . . ? C3 N2 N1 105.8(2) . . ? C2 N3 C3 104.8(2) . . ? C2 N3 C1 126.9(2) . . ? C3 N3 C1 128.3(2) . . ? N3 C1 C1 109.7(3) . 7_657 ? N3 C1 H1A 109.7 . . ? C1 C1 H1A 109.7 7_657 . ? N3 C1 H1B 109.7 . . ? C1 C1 H1B 109.7 7_657 . ? H1A C1 H1B 108.2 . . ? N1 C2 N3 110.1(2) . . ? N1 C2 H2A 125.0 . . ? N3 C2 H2A 125.0 . . ? N2 C3 N3 111.3(3) . . ? N2 C3 H3A 124.3 . . ? N3 C3 H3A 124.3 . . ? C9 C4 C5 119.2(3) . . ? C9 C4 C10 120.8(2) . . ? C5 C4 C10 119.9(2) . . ? C6 C5 C4 120.4(3) . . ? C6 C5 H5A 119.8 . . ? C4 C5 H5A 119.8 . . ? C7 C6 C5 119.5(3) . . ? C7 C6 H6A 120.2 . . ? C5 C6 H6A 120.2 . . ? O3 C7 C6 117.1(3) . . ? O3 C7 C8 122.5(3) . . ? C6 C7 C8 120.5(3) . . ? C9 C8 C7 119.8(3) . . ? C9 C8 H8A 120.1 . . ? C7 C8 H8A 120.1 . . ? C8 C9 C4 120.6(3) . . ? C8 C9 H9A 119.7 . . ? C4 C9 H9A 119.7 . . ? O1 C10 O2 120.3(2) . . ? O1 C10 C4 121.6(2) . . ? O2 C10 C4 118.1(2) . . ? O1 C10 Cd1 64.02(15) . . ? O2 C10 Cd1 56.35(13) . . ? C4 C10 Cd1 173.79(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cd1 O1 C10 -19.3(2) . . . . ? N1 Cd1 O1 C10 105.40(17) 7_656 . . . ? O2 Cd1 O1 C10 -168.89(16) 7_656 . . . ? O2 Cd1 O1 C10 -1.62(15) . . . . ? O1 Cd1 O1 C10 -117.88(18) 7_656 . . . ? C10 Cd1 O1 C10 -142.11(15) 7_656 . . . ? N1 Cd1 O2 C10 169.48(17) . . . . ? N1 Cd1 O2 C10 -86.64(17) 7_656 . . . ? O2 Cd1 O2 C10 39.58(15) 7_656 . . . ? O1 Cd1 O2 C10 71.82(17) 7_656 . . . ? O1 Cd1 O2 C10 1.58(15) . . . . ? C10 Cd1 O2 C10 64.6(2) 7_656 . . . ? N1 Cd1 N1 C2 -132.6(3) 7_656 . . . ? O2 Cd1 N1 C2 139.5(2) 7_656 . . . ? O2 Cd1 N1 C2 -24.5(2) . . . . ? O1 Cd1 N1 C2 83.0(2) 7_656 . . . ? O1 Cd1 N1 C2 -9.9(3) . . . . ? C10 Cd1 N1 C2 110.4(2) 7_656 . . . ? C10 Cd1 N1 C2 -19.2(3) . . . . ? N1 Cd1 N1 N2 39.2(2) 7_656 . . . ? O2 Cd1 N1 N2 -48.7(2) 7_656 . . . ? O2 Cd1 N1 N2 147.4(2) . . . . ? O1 Cd1 N1 N2 -105.2(2) 7_656 . . . ? O1 Cd1 N1 N2 162.0(2) . . . . ? C10 Cd1 N1 N2 -77.8(2) 7_656 . . . ? C10 Cd1 N1 N2 152.6(2) . . . . ? C2 N1 N2 C3 0.0(4) . . . . ? Cd1 N1 N2 C3 -172.9(2) . . . . ? C2 N3 C1 C1 58.3(3) . . . 7_657 ? C3 N3 C1 C1 -123.3(3) . . . 7_657 ? N2 N1 C2 N3 0.2(3) . . . . ? Cd1 N1 C2 N3 173.42(17) . . . . ? C3 N3 C2 N1 -0.3(3) . . . . ? C1 N3 C2 N1 178.4(3) . . . . ? N1 N2 C3 N3 -0.2(4) . . . . ? C2 N3 C3 N2 0.3(4) . . . . ? C1 N3 C3 N2 -178.4(3) . . . . ? C9 C4 C5 C6 1.5(5) . . . . ? C10 C4 C5 C6 -176.1(3) . . . . ? C4 C5 C6 C7 -0.4(5) . . . . ? C5 C6 C7 O3 178.3(3) . . . . ? C5 C6 C7 C8 -0.6(5) . . . . ? O3 C7 C8 C9 -178.4(3) . . . . ? C6 C7 C8 C9 0.3(5) . . . . ? C7 C8 C9 C4 0.8(5) . . . . ? C5 C4 C9 C8 -1.8(5) . . . . ? C10 C4 C9 C8 175.9(3) . . . . ? Cd1 O1 C10 O2 2.7(3) . . . . ? Cd1 O1 C10 C4 -177.1(2) . . . . ? Cd1 O2 C10 O1 -2.9(3) . . . . ? Cd1 O2 C10 C4 176.8(2) . . . . ? C9 C4 C10 O1 11.1(4) . . . . ? C5 C4 C10 O1 -171.3(3) . . . . ? C9 C4 C10 O2 -168.7(3) . . . . ? C5 C4 C10 O2 8.9(4) . . . . ? O2 Cd1 C10 O1 15.0(2) 7_656 . . . ? O2 Cd1 C10 O1 177.2(3) . . . . ? O1 Cd1 C10 O1 62.8(2) 7_656 . . . ? C10 Cd1 C10 O1 43.97(15) 7_656 . . . ? N1 Cd1 C10 O2 -11.16(18) . . . . ? N1 Cd1 C10 O2 102.23(16) 7_656 . . . ? O2 Cd1 C10 O2 -162.17(12) 7_656 . . . ? O1 Cd1 C10 O2 -114.39(16) 7_656 . . . ? O1 Cd1 C10 O2 -177.2(3) . . . . ? C10 Cd1 C10 O2 -133.20(17) 7_656 . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.661 _refine_diff_density_min -0.674 _refine_diff_density_rms 0.086 _database_code_depnum_ccdc_archive 'CCDC 968331' ####################################################################### # # 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_CdbtreNO2bdc _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 Cd N4 O8, H2 O' _chemical_formula_sum 'C11 H13 Cd N4 O9' _chemical_formula_weight 457.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0884(14) _cell_length_b 9.9983(19) _cell_length_c 10.646(2) _cell_angle_alpha 113.859(3) _cell_angle_beta 95.105(2) _cell_angle_gamma 91.085(2) _cell_volume 782.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2895 _cell_measurement_theta_min 3.1173 _cell_measurement_theta_max 27.4623 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.942 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 454 _exptl_absorpt_coefficient_mu 1.453 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5610 _exptl_absorpt_correction_T_max 0.8450 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4467 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2700 _reflns_number_gt 2271 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0136P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2700 _refine_ls_number_parameters 250 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0241 _refine_ls_R_factor_gt 0.0208 _refine_ls_wR_factor_ref 0.0440 _refine_ls_wR_factor_gt 0.0435 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.996 _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 0.02998(3) 1.08913(2) 0.29399(2) 0.01894(7) Uani 1 1 d . . . O1 O 0.1728(3) 0.89079(19) 0.1817(2) 0.0323(6) Uani 1 1 d . . . O2 O -0.0266(2) 0.82113(19) 0.27518(18) 0.0251(5) Uani 1 1 d . . . O3 O 0.0652(2) 0.33760(19) 0.31172(19) 0.0270(5) Uani 1 1 d . . . O4 O 0.1951(3) 0.1694(2) 0.1547(2) 0.0291(5) Uani 1 1 d . . . O5 O 0.4216(3) 0.2879(2) -0.2038(2) 0.0350(5) Uani 1 1 d . . . O6 O 0.3434(3) 0.4794(2) -0.2328(2) 0.0450(7) Uani 1 1 d . . . O7 O -0.1787(3) 1.0451(3) 0.1172(3) 0.0367(6) Uani 1 1 d D . . H1W H -0.171(4) 0.981(3) 0.048(3) 0.044(12) Uiso 1 1 d D . . H2W H -0.273(4) 1.047(4) 0.131(4) 0.092(18) Uiso 1 1 d D . . O8 O 0.1900(3) 1.1234(3) 0.4946(2) 0.0240(5) Uani 1 1 d D . . H3W H 0.127(4) 1.155(3) 0.551(3) 0.053(13) Uiso 1 1 d D . . H4W H 0.223(4) 1.058(3) 0.499(3) 0.028(11) Uiso 1 1 d D . . O9 O 0.4974(4) 0.0143(4) 0.1656(3) 0.0579(8) Uani 1 1 d . . . H5W H 0.459(5) -0.053(4) 0.173(4) 0.079(18) Uiso 1 1 d . . . H6W H 0.424(6) 0.065(5) 0.149(5) 0.10(2) Uiso 1 1 d . . . N1 N -0.4066(3) 1.3196(2) 0.4577(2) 0.0213(6) Uani 1 1 d . . . N2 N -0.1859(3) 1.1932(2) 0.4218(2) 0.0238(6) Uani 1 1 d . . . N3 N -0.2897(3) 1.1377(2) 0.4873(2) 0.0248(6) Uani 1 1 d . . . N4 N 0.3528(3) 0.4033(3) -0.1670(2) 0.0270(6) Uani 1 1 d . . . C1 C -0.5301(3) 1.4219(3) 0.4521(3) 0.0242(7) Uani 1 1 d . . . H1A H -0.6348 1.3967 0.4792 0.029 Uiso 1 1 calc R . . H1B H -0.5509 1.4143 0.3572 0.029 Uiso 1 1 calc R . . C2 C -0.2600(4) 1.3022(3) 0.4060(3) 0.0255(7) Uani 1 1 d . . . H2A H -0.2161 1.3598 0.3642 0.031 Uiso 1 1 calc R . . C3 C -0.4191(4) 1.2144(3) 0.5067(3) 0.0243(7) Uani 1 1 d . . . H3A H -0.5102 1.1993 0.5494 0.029 Uiso 1 1 calc R . . C4 C 0.1501(3) 0.6412(3) 0.1415(3) 0.0169(6) Uani 1 1 d . . . C5 C 0.1228(3) 0.5427(3) 0.2008(3) 0.0175(6) Uani 1 1 d . . . H5A H 0.0667 0.5719 0.2805 0.021 Uiso 1 1 calc R . . C6 C 0.1773(3) 0.4021(3) 0.1439(3) 0.0173(6) Uani 1 1 d . . . C7 C 0.2571(3) 0.3566(3) 0.0238(3) 0.0189(6) Uani 1 1 d . . . H7A H 0.2960 0.2620 -0.0155 0.023 Uiso 1 1 calc R . . C8 C 0.2774(3) 0.4547(3) -0.0355(3) 0.0181(6) Uani 1 1 d . . . C9 C 0.2277(3) 0.5956(3) 0.0211(3) 0.0197(7) Uani 1 1 d . . . H9A H 0.2459 0.6602 -0.0211 0.024 Uiso 1 1 calc R . . C10 C 0.0935(4) 0.7947(3) 0.2052(3) 0.0209(7) Uani 1 1 d . . . C11 C 0.1442(4) 0.2956(3) 0.2078(3) 0.0216(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.02214(12) 0.01615(12) 0.02149(12) 0.00958(9) 0.00713(9) 0.00534(9) O1 0.0413(14) 0.0151(11) 0.0470(14) 0.0157(10) 0.0211(12) 0.0073(10) O2 0.0258(12) 0.0218(11) 0.0250(11) 0.0052(9) 0.0089(10) 0.0073(9) O3 0.0360(13) 0.0241(11) 0.0275(11) 0.0157(10) 0.0111(10) 0.0039(10) O4 0.0412(14) 0.0162(11) 0.0350(13) 0.0141(10) 0.0106(11) 0.0075(10) O5 0.0369(14) 0.0361(13) 0.0285(12) 0.0072(11) 0.0137(11) 0.0131(11) O6 0.0720(19) 0.0454(14) 0.0316(13) 0.0253(12) 0.0262(13) 0.0173(13) O7 0.0325(16) 0.0440(16) 0.0223(14) 0.0024(13) -0.0003(12) 0.0063(13) O8 0.0271(14) 0.0249(14) 0.0237(12) 0.0126(11) 0.0058(11) 0.0087(11) O9 0.0321(17) 0.072(2) 0.084(2) 0.047(2) 0.0045(16) 0.0040(17) N1 0.0192(14) 0.0216(13) 0.0241(13) 0.0094(11) 0.0069(11) 0.0075(11) N2 0.0229(14) 0.0257(14) 0.0275(14) 0.0141(12) 0.0079(12) 0.0076(11) N3 0.0268(15) 0.0264(14) 0.0253(14) 0.0133(12) 0.0103(12) 0.0066(12) N4 0.0297(16) 0.0282(15) 0.0214(14) 0.0073(12) 0.0083(12) 0.0008(13) C1 0.0215(17) 0.0228(16) 0.0279(17) 0.0095(14) 0.0032(14) 0.0065(13) C2 0.0285(18) 0.0268(17) 0.0268(17) 0.0150(14) 0.0101(15) 0.0081(14) C3 0.0240(18) 0.0233(17) 0.0270(17) 0.0103(14) 0.0082(14) 0.0049(14) C4 0.0154(15) 0.0140(15) 0.0196(15) 0.0054(13) 0.0002(13) -0.0001(12) C5 0.0167(15) 0.0195(15) 0.0168(14) 0.0077(13) 0.0028(13) 0.0017(13) C6 0.0182(15) 0.0156(15) 0.0183(15) 0.0077(13) -0.0012(13) 0.0000(12) C7 0.0201(16) 0.0117(14) 0.0212(15) 0.0032(13) 0.0007(13) 0.0026(12) C8 0.0199(16) 0.0197(16) 0.0128(14) 0.0041(12) 0.0042(12) 0.0010(13) C9 0.0211(16) 0.0204(16) 0.0213(16) 0.0121(13) 0.0043(13) 0.0010(13) C10 0.0258(17) 0.0169(16) 0.0182(15) 0.0058(13) -0.0017(14) 0.0045(14) C11 0.0225(17) 0.0204(17) 0.0221(16) 0.0106(14) -0.0052(14) -0.0045(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 Cd1 O1 2.2605(19) . ? Cd1 O8 2.292(2) . ? Cd1 O7 2.307(3) . ? Cd1 N2 2.308(2) . ? Cd1 O3 2.4233(18) 1_565 ? Cd1 O4 2.4295(18) 1_565 ? Cd1 O2 2.6330(18) . ? O1 C10 1.264(3) . ? O2 C10 1.243(3) . ? O3 C11 1.252(3) . ? O3 Cd1 2.4233(18) 1_545 ? O4 C11 1.251(3) . ? O4 Cd1 2.4295(18) 1_545 ? O5 N4 1.221(3) . ? O6 N4 1.225(3) . ? O7 H1W 0.77(3) . ? O7 H2W 0.79(3) . ? O8 H3W 0.79(3) . ? O8 H4W 0.72(2) . ? O9 H5W 0.77(4) . ? O9 H6W 0.83(5) . ? N1 C2 1.336(3) . ? N1 C3 1.355(3) . ? N1 C1 1.458(3) . ? N2 C2 1.315(4) . ? N2 N3 1.378(3) . ? N3 C3 1.291(4) . ? N4 C8 1.476(3) . ? C1 C1 1.520(5) 2_486 ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 H2A 0.9400 . ? C3 H3A 0.9400 . ? C4 C9 1.388(3) . ? C4 C5 1.392(3) . ? C4 C10 1.504(4) . ? C5 C6 1.386(4) . ? C5 H5A 0.9400 . ? C6 C7 1.395(3) . ? C6 C11 1.508(3) . ? C7 C8 1.378(3) . ? C7 H7A 0.9400 . ? C8 C9 1.374(4) . ? C9 H9A 0.9400 . ? 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 O8 88.88(9) . . ? O1 Cd1 O7 96.49(9) . . ? O8 Cd1 O7 167.14(9) . . ? O1 Cd1 N2 150.14(7) . . ? O8 Cd1 N2 89.19(9) . . ? O7 Cd1 N2 80.33(9) . . ? O1 Cd1 O3 129.76(6) . 1_565 ? O8 Cd1 O3 97.12(7) . 1_565 ? O7 Cd1 O3 88.44(8) . 1_565 ? N2 Cd1 O3 80.03(7) . 1_565 ? O1 Cd1 O4 76.85(6) . 1_565 ? O8 Cd1 O4 108.47(7) . 1_565 ? O7 Cd1 O4 84.18(8) . 1_565 ? N2 Cd1 O4 131.62(7) . 1_565 ? O3 Cd1 O4 53.88(6) 1_565 1_565 ? O1 Cd1 O2 53.00(6) . . ? O8 Cd1 O2 84.44(7) . . ? O7 Cd1 O2 89.46(8) . . ? N2 Cd1 O2 97.17(7) . . ? O3 Cd1 O2 176.74(6) 1_565 . ? O4 Cd1 O2 128.34(6) 1_565 . ? O1 Cd1 C11 103.83(8) . 1_565 ? O8 Cd1 C11 106.98(8) . 1_565 ? O7 Cd1 C11 83.15(8) . 1_565 ? N2 Cd1 C11 105.22(8) . 1_565 ? O3 Cd1 C11 27.08(7) 1_565 1_565 ? O4 Cd1 C11 27.06(7) 1_565 1_565 ? O2 Cd1 C11 154.80(7) . 1_565 ? C10 O1 Cd1 100.18(17) . . ? C10 O2 Cd1 83.32(15) . . ? C11 O3 Cd1 91.19(16) . 1_545 ? C11 O4 Cd1 90.93(16) . 1_545 ? Cd1 O7 H1W 118(3) . . ? Cd1 O7 H2W 121(3) . . ? H1W O7 H2W 108(4) . . ? Cd1 O8 H3W 102(3) . . ? Cd1 O8 H4W 116(3) . . ? H3W O8 H4W 109(3) . . ? H5W O9 H6W 112(4) . . ? C2 N1 C3 104.7(2) . . ? C2 N1 C1 127.1(2) . . ? C3 N1 C1 128.1(2) . . ? C2 N2 N3 106.9(2) . . ? C2 N2 Cd1 120.00(18) . . ? N3 N2 Cd1 130.30(17) . . ? C3 N3 N2 106.6(2) . . ? O5 N4 O6 123.7(2) . . ? O5 N4 C8 118.3(2) . . ? O6 N4 C8 118.0(3) . . ? N1 C1 C1 110.6(3) . 2_486 ? N1 C1 H1A 109.5 . . ? C1 C1 H1A 109.5 2_486 . ? N1 C1 H1B 109.5 . . ? C1 C1 H1B 109.5 2_486 . ? H1A C1 H1B 108.1 . . ? N2 C2 N1 110.5(2) . . ? N2 C2 H2A 124.8 . . ? N1 C2 H2A 124.8 . . ? N3 C3 N1 111.3(2) . . ? N3 C3 H3A 124.3 . . ? N1 C3 H3A 124.3 . . ? C9 C4 C5 119.2(2) . . ? C9 C4 C10 120.1(2) . . ? C5 C4 C10 120.6(2) . . ? C6 C5 C4 120.8(2) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.6 . . ? C5 C6 C7 120.0(2) . . ? C5 C6 C11 120.3(2) . . ? C7 C6 C11 119.7(2) . . ? C8 C7 C6 118.0(3) . . ? C8 C7 H7A 121.0 . . ? C6 C7 H7A 121.0 . . ? C9 C8 C7 122.9(2) . . ? C9 C8 N4 119.3(2) . . ? C7 C8 N4 117.8(2) . . ? C8 C9 C4 119.0(2) . . ? C8 C9 H9A 120.5 . . ? C4 C9 H9A 120.5 . . ? O2 C10 O1 123.5(3) . . ? O2 C10 C4 120.2(2) . . ? O1 C10 C4 116.3(2) . . ? O4 C11 O3 122.8(2) . . ? O4 C11 C6 119.0(2) . . ? O3 C11 C6 118.2(3) . . ? O4 C11 Cd1 62.01(13) . 1_545 ? O3 C11 Cd1 61.73(13) . 1_545 ? C6 C11 Cd1 169.59(19) . 1_545 ? 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 O8 Cd1 O1 C10 84.33(18) . . . . ? O7 Cd1 O1 C10 -83.95(18) . . . . ? N2 Cd1 O1 C10 -2.1(3) . . . . ? O3 Cd1 O1 C10 -177.33(15) 1_565 . . . ? O4 Cd1 O1 C10 -166.40(18) 1_565 . . . ? O2 Cd1 O1 C10 0.45(16) . . . . ? C11 Cd1 O1 C10 -168.46(17) 1_565 . . . ? O1 Cd1 O2 C10 -0.45(16) . . . . ? O8 Cd1 O2 C10 -93.25(17) . . . . ? O7 Cd1 O2 C10 98.09(17) . . . . ? N2 Cd1 O2 C10 178.28(16) . . . . ? O4 Cd1 O2 C10 15.95(19) 1_565 . . . ? C11 Cd1 O2 C10 25.6(3) 1_565 . . . ? O1 Cd1 N2 C2 -146.1(2) . . . . ? O8 Cd1 N2 C2 127.5(2) . . . . ? O7 Cd1 N2 C2 -60.0(2) . . . . ? O3 Cd1 N2 C2 30.2(2) 1_565 . . . ? O4 Cd1 N2 C2 13.3(3) 1_565 . . . ? O2 Cd1 N2 C2 -148.2(2) . . . . ? C11 Cd1 N2 C2 20.1(2) 1_565 . . . ? O1 Cd1 N2 N3 12.4(3) . . . . ? O8 Cd1 N2 N3 -74.0(2) . . . . ? O7 Cd1 N2 N3 98.5(2) . . . . ? O3 Cd1 N2 N3 -171.3(2) 1_565 . . . ? O4 Cd1 N2 N3 171.76(19) 1_565 . . . ? O2 Cd1 N2 N3 10.3(2) . . . . ? C11 Cd1 N2 N3 178.7(2) 1_565 . . . ? C2 N2 N3 C3 0.3(3) . . . . ? Cd1 N2 N3 C3 -160.4(2) . . . . ? C2 N1 C1 C1 -71.7(4) . . . 2_486 ? C3 N1 C1 C1 113.6(3) . . . 2_486 ? N3 N2 C2 N1 -0.2(3) . . . . ? Cd1 N2 C2 N1 162.85(17) . . . . ? C3 N1 C2 N2 0.0(3) . . . . ? C1 N1 C2 N2 -175.7(2) . . . . ? N2 N3 C3 N1 -0.3(3) . . . . ? C2 N1 C3 N3 0.2(3) . . . . ? C1 N1 C3 N3 175.8(2) . . . . ? C9 C4 C5 C6 2.3(4) . . . . ? C10 C4 C5 C6 -178.8(3) . . . . ? C4 C5 C6 C7 -1.5(4) . . . . ? C4 C5 C6 C11 -178.9(2) . . . . ? C5 C6 C7 C8 -0.7(4) . . . . ? C11 C6 C7 C8 176.7(2) . . . . ? C6 C7 C8 C9 2.3(4) . . . . ? C6 C7 C8 N4 -176.4(2) . . . . ? O5 N4 C8 C9 167.7(3) . . . . ? O6 N4 C8 C9 -12.0(4) . . . . ? O5 N4 C8 C7 -13.5(4) . . . . ? O6 N4 C8 C7 166.8(3) . . . . ? C7 C8 C9 C4 -1.5(4) . . . . ? N4 C8 C9 C4 177.1(2) . . . . ? C5 C4 C9 C8 -0.8(4) . . . . ? C10 C4 C9 C8 -179.6(2) . . . . ? Cd1 O2 C10 O1 0.8(3) . . . . ? Cd1 O2 C10 C4 -178.3(2) . . . . ? Cd1 O1 C10 O2 -0.9(3) . . . . ? Cd1 O1 C10 C4 178.20(19) . . . . ? C9 C4 C10 O2 151.9(3) . . . . ? C5 C4 C10 O2 -26.9(4) . . . . ? C9 C4 C10 O1 -27.2(4) . . . . ? C5 C4 C10 O1 153.9(2) . . . . ? Cd1 O4 C11 O3 11.2(3) 1_545 . . . ? Cd1 O4 C11 C6 -168.2(2) 1_545 . . . ? Cd1 O3 C11 O4 -11.3(3) 1_545 . . . ? Cd1 O3 C11 C6 168.2(2) 1_545 . . . ? C5 C6 C11 O4 -179.8(3) . . . . ? C7 C6 C11 O4 2.8(4) . . . . ? C5 C6 C11 O3 0.7(4) . . . . ? C7 C6 C11 O3 -176.6(3) . . . . ? C5 C6 C11 Cd1 87.4(11) . . . 1_545 ? C7 C6 C11 Cd1 -89.9(11) . . . 1_545 ? 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 O7 H1W O4 0.77(3) 2.05(3) 2.809(3) 167(4) 2_565 O7 H2W O9 0.79(3) 1.97(3) 2.750(4) 169(4) 1_465 O8 H3W O2 0.79(3) 2.02(3) 2.751(3) 154(3) 2_576 O8 H4W N3 0.72(2) 2.10(2) 2.821(3) 174(3) 2_576 O9 H5W O1 0.77(4) 2.39(4) 2.928(3) 128(4) 1_545 O9 H6W O4 0.83(5) 2.14(5) 2.938(4) 160(4) . _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.529 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.071 _database_code_depnum_ccdc_archive 'CCDC 968332' ####################################################################### # # 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_CdbtreSO3bdc _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H22 Cd3 N12 O14 S2, 4(H2O)' _chemical_formula_sum 'C28 H30 Cd3 N12 O18 S2' _chemical_formula_weight 1223.96 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.891(3) _cell_length_b 9.658(3) _cell_length_c 13.359(4) _cell_angle_alpha 100.128(4) _cell_angle_beta 90.511(3) _cell_angle_gamma 116.456(4) _cell_volume 1006.1(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3953 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 25.3 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.020 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 602 _exptl_absorpt_coefficient_mu 1.766 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5386 _exptl_absorpt_correction_T_max 0.7190 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9758 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3659 _reflns_number_gt 3258 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _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^)+(0.0380P)^2^+1.4872P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3659 _refine_ls_number_parameters 298 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0350 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0672 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.030 _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 0.95748(3) 0.71777(3) 0.739256(19) 0.02260(10) Uani 1 1 d . . . Cd2 Cd 1.0000 0.5000 0.5000 0.02016(11) Uani 1 2 d S . . S1 S 0.34503(13) 0.15922(12) 0.28326(8) 0.0322(2) Uani 1 1 d . . . O1 O 0.7974(3) 0.5334(3) 0.59907(19) 0.0257(6) Uani 1 1 d . . . O2 O 0.7002(3) 0.4440(3) 0.7380(2) 0.0377(7) Uani 1 1 d . . . O3 O 0.1844(4) -0.0956(3) 0.6894(2) 0.0363(7) Uani 1 1 d . . . O4 O 0.1200(4) -0.2389(3) 0.5309(2) 0.0454(8) Uani 1 1 d . . . O5 O 0.1658(4) 0.1205(3) 0.2693(2) 0.0390(7) Uani 1 1 d . . . O6 O 0.4542(4) 0.3122(4) 0.2637(3) 0.0591(10) Uani 1 1 d . . . O7 O 0.3710(4) 0.0296(4) 0.2289(2) 0.0509(9) Uani 1 1 d . . . O8 O 1.4485(6) 1.0492(6) 0.9175(3) 0.0802(13) Uani 1 1 d D . . H1W H 1.446(6) 1.048(6) 0.8537(18) 0.096 Uiso 1 1 d D . . H2W H 1.454(8) 0.965(4) 0.9207(14) 0.096 Uiso 1 1 d D . . O9 O 1.3399(7) 0.6170(6) 0.0516(3) 0.0792(13) Uani 1 1 d D . . H3W H 1.268(5) 0.609(8) 0.095(2) 0.095 Uiso 1 1 d D . . H4W H 1.398(8) 0.716(3) 0.057(5) 0.095 Uiso 1 1 d D . . N1 N 0.9604(4) 0.7727(4) 0.9097(2) 0.0313(8) Uani 1 1 d . . . N2 N 1.0970(5) 0.8002(6) 0.9735(3) 0.0507(11) Uani 1 1 d . . . N3 N 0.8932(4) 0.7948(4) 1.0648(2) 0.0259(7) Uani 1 1 d . . . N4 N 0.8876(4) 0.5187(4) 1.3481(2) 0.0278(7) Uani 1 1 d . . . N5 N 0.8947(4) 0.4303(4) 1.2561(2) 0.0282(7) Uani 1 1 d . . . N6 N 0.7745(4) 0.5731(4) 1.2248(2) 0.0253(7) Uani 1 1 d . . . C1 C 0.7944(6) 0.7986(5) 1.1517(3) 0.0327(9) Uani 1 1 d . . . H1A H 0.7249 0.8487 1.1387 0.039 Uiso 1 1 calc R . . H1B H 0.8709 0.8619 1.2125 0.039 Uiso 1 1 calc R . . C2 C 0.6825(5) 0.6356(5) 1.1708(3) 0.0310(9) Uani 1 1 d . . . H2A H 0.5934 0.6396 1.2107 0.037 Uiso 1 1 calc R . . H2B H 0.6300 0.5643 1.1059 0.037 Uiso 1 1 calc R . . C3 C 0.8407(5) 0.7709(5) 0.9663(3) 0.0346(10) Uani 1 1 d . . . H3A H 0.7349 0.7553 0.9418 0.042 Uiso 1 1 calc R . . C4 C 1.0518(6) 0.8130(6) 1.0649(3) 0.0464(12) Uani 1 1 d . . . H4A H 1.1208 0.8325 1.1237 0.056 Uiso 1 1 calc R . . C5 C 0.8157(5) 0.6011(5) 1.3253(3) 0.0296(9) Uani 1 1 d . . . H5A H 0.7951 0.6715 1.3732 0.036 Uiso 1 1 calc R . . C6 C 0.8256(5) 0.4648(5) 1.1843(3) 0.0290(9) Uani 1 1 d . . . H6A H 0.8132 0.4211 1.1151 0.035 Uiso 1 1 calc R . . C7 C 0.5467(4) 0.2899(4) 0.5776(3) 0.0222(8) Uani 1 1 d . . . C8 C 0.4458(4) 0.1580(4) 0.6166(3) 0.0233(8) Uani 1 1 d . . . H8A H 0.4665 0.1561 0.6846 0.028 Uiso 1 1 calc R . . C9 C 0.3137(5) 0.0284(4) 0.5548(3) 0.0243(8) Uani 1 1 d . . . C10 C 0.2867(5) 0.0304(4) 0.4530(3) 0.0269(8) Uani 1 1 d . . . H10A H 0.2017 -0.0575 0.4106 0.032 Uiso 1 1 calc R . . C11 C 0.3860(4) 0.1633(4) 0.4138(3) 0.0253(8) Uani 1 1 d . . . C12 C 0.5154(4) 0.2927(4) 0.4760(3) 0.0257(8) Uani 1 1 d . . . H12A H 0.5815 0.3816 0.4498 0.031 Uiso 1 1 calc R . . C13 C 0.6899(4) 0.4285(4) 0.6434(3) 0.0245(8) Uani 1 1 d . . . C14 C 0.1988(4) -0.1144(4) 0.5947(3) 0.0253(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.02508(16) 0.01798(15) 0.01853(15) 0.00287(11) 0.00256(11) 0.00463(12) Cd2 0.0248(2) 0.01509(19) 0.01460(19) 0.00228(14) 0.00180(15) 0.00401(15) S1 0.0278(5) 0.0376(6) 0.0257(5) 0.0083(4) -0.0020(4) 0.0095(5) O1 0.0213(13) 0.0165(12) 0.0270(14) 0.0009(10) 0.0041(11) -0.0010(11) O2 0.0338(16) 0.0394(17) 0.0206(15) 0.0012(12) 0.0027(12) 0.0015(13) O3 0.0362(16) 0.0277(15) 0.0390(17) 0.0121(13) 0.0173(14) 0.0071(13) O4 0.0495(19) 0.0143(14) 0.0485(19) 0.0043(13) -0.0027(15) -0.0056(13) O5 0.0321(16) 0.0366(17) 0.0459(18) 0.0036(14) -0.0091(14) 0.0155(14) O6 0.050(2) 0.056(2) 0.048(2) 0.0305(17) -0.0086(16) -0.0042(17) O7 0.054(2) 0.071(2) 0.0342(18) -0.0072(16) -0.0015(15) 0.0396(19) O8 0.080(3) 0.109(4) 0.061(3) 0.008(3) 0.005(2) 0.055(3) O9 0.124(4) 0.081(3) 0.044(2) 0.007(2) -0.002(2) 0.059(3) N1 0.0356(19) 0.038(2) 0.0185(16) 0.0033(14) 0.0028(15) 0.0154(16) N2 0.037(2) 0.084(3) 0.0211(19) 0.0011(19) -0.0006(17) 0.022(2) N3 0.0349(18) 0.0264(17) 0.0174(16) 0.0032(13) 0.0043(14) 0.0154(15) N4 0.0349(18) 0.0279(17) 0.0199(16) 0.0032(13) 0.0008(14) 0.0143(15) N5 0.0355(19) 0.0292(18) 0.0212(17) 0.0037(14) -0.0002(14) 0.0163(15) N6 0.0259(17) 0.0288(17) 0.0229(17) 0.0093(13) 0.0053(13) 0.0122(14) C1 0.051(3) 0.037(2) 0.026(2) 0.0093(17) 0.0144(19) 0.032(2) C2 0.030(2) 0.046(3) 0.025(2) 0.0097(18) 0.0057(17) 0.024(2) C3 0.035(2) 0.049(3) 0.022(2) 0.0095(18) 0.0004(18) 0.020(2) C4 0.034(2) 0.073(3) 0.027(2) 0.001(2) -0.008(2) 0.023(2) C5 0.039(2) 0.030(2) 0.023(2) 0.0048(16) 0.0030(18) 0.0193(19) C6 0.034(2) 0.033(2) 0.022(2) 0.0034(16) 0.0042(17) 0.0173(19) C7 0.0181(18) 0.0170(17) 0.0254(19) 0.0013(15) 0.0047(15) 0.0036(15) C8 0.0228(19) 0.0243(19) 0.0207(19) 0.0043(15) 0.0058(15) 0.0088(16) C9 0.0225(19) 0.0161(18) 0.030(2) 0.0015(15) 0.0097(16) 0.0063(15) C10 0.0216(19) 0.0191(19) 0.029(2) 0.0026(15) -0.0003(16) 0.0008(16) C11 0.0208(19) 0.025(2) 0.025(2) 0.0056(16) 0.0012(16) 0.0060(16) C12 0.0197(18) 0.0198(19) 0.032(2) 0.0093(16) 0.0018(16) 0.0026(15) C13 0.0198(18) 0.0205(19) 0.028(2) 0.0026(15) 0.0058(16) 0.0054(16) C14 0.0200(19) 0.0169(19) 0.037(2) 0.0068(16) 0.0084(17) 0.0056(16) _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 O3 2.229(3) 1_665 ? Cd1 N1 2.243(3) . ? Cd1 O1 2.286(2) . ? Cd1 O5 2.290(3) 2_666 ? Cd1 N5 2.340(3) 2_767 ? Cd1 O2 2.611(3) . ? Cd2 O4 2.213(3) 2_656 ? Cd2 O4 2.213(3) 1_665 ? Cd2 N4 2.325(3) 1_554 ? Cd2 N4 2.325(3) 2_767 ? Cd2 O1 2.348(2) . ? Cd2 O1 2.348(2) 2_766 ? S1 O6 1.433(3) . ? S1 O7 1.445(3) . ? S1 O5 1.467(3) . ? S1 C11 1.769(4) . ? O1 C13 1.284(4) . ? O2 C13 1.243(4) . ? O3 C14 1.262(5) . ? O3 Cd1 2.229(3) 1_445 ? O4 C14 1.242(5) . ? O4 Cd2 2.213(3) 1_445 ? O5 Cd1 2.290(3) 2_666 ? O8 H1W 0.851(19) . ? O8 H2W 0.850(19) . ? O9 H3W 0.86(2) . ? O9 H4W 0.85(2) . ? N1 C3 1.307(5) . ? N1 N2 1.373(5) . ? N2 C4 1.292(6) . ? N3 C3 1.337(5) . ? N3 C4 1.341(5) . ? N3 C1 1.467(5) . ? N4 C5 1.291(5) . ? N4 N5 1.387(4) . ? N4 Cd2 2.325(3) 1_556 ? N5 C6 1.301(5) . ? N5 Cd1 2.340(3) 2_767 ? N6 C5 1.337(5) . ? N6 C6 1.350(5) . ? N6 C2 1.461(5) . ? C1 C2 1.512(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9300 . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.387(5) . ? C7 C12 1.391(5) . ? C7 C13 1.494(5) . ? C8 C9 1.392(5) . ? C8 H8A 0.9300 . ? C9 C10 1.383(5) . ? C9 C14 1.498(5) . ? C10 C11 1.392(5) . ? C10 H10A 0.9300 . ? C11 C12 1.382(5) . ? C12 H12A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cd1 N1 109.95(12) 1_665 . ? O3 Cd1 O1 109.26(10) 1_665 . ? N1 Cd1 O1 140.79(11) . . ? O3 Cd1 O5 85.85(11) 1_665 2_666 ? N1 Cd1 O5 87.88(11) . 2_666 ? O1 Cd1 O5 94.69(10) . 2_666 ? O3 Cd1 N5 89.08(11) 1_665 2_767 ? N1 Cd1 N5 93.69(11) . 2_767 ? O1 Cd1 N5 87.14(10) . 2_767 ? O5 Cd1 N5 174.93(11) 2_666 2_767 ? O3 Cd1 O2 160.11(9) 1_665 . ? N1 Cd1 O2 88.27(11) . . ? O1 Cd1 O2 53.02(9) . . ? O5 Cd1 O2 103.26(10) 2_666 . ? N5 Cd1 O2 81.62(11) 2_767 . ? O4 Cd2 O4 180.000(1) 2_656 1_665 ? O4 Cd2 N4 95.56(11) 2_656 1_554 ? O4 Cd2 N4 84.44(11) 1_665 1_554 ? O4 Cd2 N4 84.44(11) 2_656 2_767 ? O4 Cd2 N4 95.56(11) 1_665 2_767 ? N4 Cd2 N4 180.000(1) 1_554 2_767 ? O4 Cd2 O1 97.67(10) 2_656 . ? O4 Cd2 O1 82.33(10) 1_665 . ? N4 Cd2 O1 95.11(10) 1_554 . ? N4 Cd2 O1 84.89(10) 2_767 . ? O4 Cd2 O1 82.33(10) 2_656 2_766 ? O4 Cd2 O1 97.67(10) 1_665 2_766 ? N4 Cd2 O1 84.89(10) 1_554 2_766 ? N4 Cd2 O1 95.11(10) 2_767 2_766 ? O1 Cd2 O1 180.0 . 2_766 ? O6 S1 O7 116.0(2) . . ? O6 S1 O5 112.7(2) . . ? O7 S1 O5 109.62(19) . . ? O6 S1 C11 107.57(19) . . ? O7 S1 C11 104.59(19) . . ? O5 S1 C11 105.46(18) . . ? C13 O1 Cd1 99.8(2) . . ? C13 O1 Cd2 124.9(2) . . ? Cd1 O1 Cd2 102.99(10) . . ? C13 O2 Cd1 85.6(2) . . ? C14 O3 Cd1 116.1(2) . 1_445 ? C14 O4 Cd2 146.7(3) . 1_445 ? S1 O5 Cd1 129.79(18) . 2_666 ? H1W O8 H2W 103(2) . . ? H3W O9 H4W 104(7) . . ? C3 N1 N2 107.9(3) . . ? C3 N1 Cd1 130.3(3) . . ? N2 N1 Cd1 121.6(2) . . ? C4 N2 N1 105.7(4) . . ? C3 N3 C4 105.0(3) . . ? C3 N3 C1 126.2(3) . . ? C4 N3 C1 128.8(3) . . ? C5 N4 N5 106.0(3) . . ? C5 N4 Cd2 134.0(3) . 1_556 ? N5 N4 Cd2 120.0(2) . 1_556 ? C6 N5 N4 107.2(3) . . ? C6 N5 Cd1 135.3(3) . 2_767 ? N4 N5 Cd1 117.2(2) . 2_767 ? C5 N6 C6 104.7(3) . . ? C5 N6 C2 128.0(3) . . ? C6 N6 C2 127.2(3) . . ? N3 C1 C2 112.4(3) . . ? N3 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? N3 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? N6 C2 C1 112.9(3) . . ? N6 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? N6 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? N1 C3 N3 109.7(4) . . ? N1 C3 H3A 125.1 . . ? N3 C3 H3A 125.1 . . ? N2 C4 N3 111.7(4) . . ? N2 C4 H4A 124.1 . . ? N3 C4 H4A 124.1 . . ? N4 C5 N6 111.9(3) . . ? N4 C5 H5A 124.0 . . ? N6 C5 H5A 124.0 . . ? N5 C6 N6 110.2(3) . . ? N5 C6 H6A 124.9 . . ? N6 C6 H6A 124.9 . . ? C8 C7 C12 119.7(3) . . ? C8 C7 C13 120.7(3) . . ? C12 C7 C13 119.6(3) . . ? C7 C8 C9 120.5(3) . . ? C7 C8 H8A 119.8 . . ? C9 C8 H8A 119.8 . . ? C10 C9 C8 119.4(3) . . ? C10 C9 C14 118.5(3) . . ? C8 C9 C14 122.1(3) . . ? C9 C10 C11 120.4(3) . . ? C9 C10 H10A 119.8 . . ? C11 C10 H10A 119.8 . . ? C12 C11 C10 120.0(3) . . ? C12 C11 S1 121.7(3) . . ? C10 C11 S1 118.3(3) . . ? C11 C12 C7 120.0(3) . . ? C11 C12 H12A 120.0 . . ? C7 C12 H12A 120.0 . . ? O2 C13 O1 121.5(3) . . ? O2 C13 C7 120.8(3) . . ? O1 C13 C7 117.6(3) . . ? O4 C14 O3 125.8(3) . . ? O4 C14 C9 117.0(3) . . ? O3 C14 C9 117.1(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Cd1 O1 C13 171.4(2) 1_665 . . . ? N1 Cd1 O1 C13 -9.0(3) . . . . ? O5 Cd1 O1 C13 -101.4(2) 2_666 . . . ? N5 Cd1 O1 C13 83.4(2) 2_767 . . . ? O2 Cd1 O1 C13 1.7(2) . . . . ? O3 Cd1 O1 Cd2 41.91(13) 1_665 . . . ? N1 Cd1 O1 Cd2 -138.45(15) . . . . ? O5 Cd1 O1 Cd2 129.15(11) 2_666 . . . ? N5 Cd1 O1 Cd2 -46.11(11) 2_767 . . . ? O2 Cd1 O1 Cd2 -127.77(14) . . . . ? O4 Cd2 O1 C13 19.0(3) 2_656 . . . ? O4 Cd2 O1 C13 -161.0(3) 1_665 . . . ? N4 Cd2 O1 C13 115.3(3) 1_554 . . . ? N4 Cd2 O1 C13 -64.7(3) 2_767 . . . ? O4 Cd2 O1 Cd1 130.96(11) 2_656 . . . ? O4 Cd2 O1 Cd1 -49.04(11) 1_665 . . . ? N4 Cd2 O1 Cd1 -132.72(11) 1_554 . . . ? N4 Cd2 O1 Cd1 47.28(11) 2_767 . . . ? O3 Cd1 O2 C13 -31.5(4) 1_665 . . . ? N1 Cd1 O2 C13 171.5(2) . . . . ? O1 Cd1 O2 C13 -1.7(2) . . . . ? O5 Cd1 O2 C13 84.1(2) 2_666 . . . ? N5 Cd1 O2 C13 -94.5(2) 2_767 . . . ? O6 S1 O5 Cd1 -16.7(3) . . . 2_666 ? O7 S1 O5 Cd1 -147.5(2) . . . 2_666 ? C11 S1 O5 Cd1 100.4(2) . . . 2_666 ? O3 Cd1 N1 C3 133.3(4) 1_665 . . . ? O1 Cd1 N1 C3 -46.4(4) . . . . ? O5 Cd1 N1 C3 48.5(4) 2_666 . . . ? N5 Cd1 N1 C3 -136.4(4) 2_767 . . . ? O2 Cd1 N1 C3 -54.9(4) . . . . ? O3 Cd1 N1 N2 -53.8(3) 1_665 . . . ? O1 Cd1 N1 N2 126.5(3) . . . . ? O5 Cd1 N1 N2 -138.6(3) 2_666 . . . ? N5 Cd1 N1 N2 36.5(3) 2_767 . . . ? O2 Cd1 N1 N2 118.0(3) . . . . ? C3 N1 N2 C4 0.2(5) . . . . ? Cd1 N1 N2 C4 -174.2(3) . . . . ? C5 N4 N5 C6 -0.4(4) . . . . ? Cd2 N4 N5 C6 -179.2(3) 1_556 . . . ? C5 N4 N5 Cd1 173.7(3) . . . 2_767 ? Cd2 N4 N5 Cd1 -5.0(3) 1_556 . . 2_767 ? C3 N3 C1 C2 84.2(5) . . . . ? C4 N3 C1 C2 -95.4(5) . . . . ? C5 N6 C2 C1 82.9(5) . . . . ? C6 N6 C2 C1 -102.5(4) . . . . ? N3 C1 C2 N6 78.8(4) . . . . ? N2 N1 C3 N3 -0.5(5) . . . . ? Cd1 N1 C3 N3 173.1(3) . . . . ? C4 N3 C3 N1 0.7(5) . . . . ? C1 N3 C3 N1 -179.0(3) . . . . ? N1 N2 C4 N3 0.3(6) . . . . ? C3 N3 C4 N2 -0.6(5) . . . . ? C1 N3 C4 N2 179.1(4) . . . . ? N5 N4 C5 N6 0.2(4) . . . . ? Cd2 N4 C5 N6 178.6(3) 1_556 . . . ? C6 N6 C5 N4 0.2(5) . . . . ? C2 N6 C5 N4 175.8(3) . . . . ? N4 N5 C6 N6 0.5(4) . . . . ? Cd1 N5 C6 N6 -172.1(3) 2_767 . . . ? C5 N6 C6 N5 -0.4(4) . . . . ? C2 N6 C6 N5 -176.1(3) . . . . ? C12 C7 C8 C9 0.1(5) . . . . ? C13 C7 C8 C9 -179.3(3) . . . . ? C7 C8 C9 C10 1.8(5) . . . . ? C7 C8 C9 C14 -178.2(3) . . . . ? C8 C9 C10 C11 -2.7(5) . . . . ? C14 C9 C10 C11 177.3(3) . . . . ? C9 C10 C11 C12 1.7(6) . . . . ? C9 C10 C11 S1 -179.7(3) . . . . ? O6 S1 C11 C12 -5.8(4) . . . . ? O7 S1 C11 C12 118.2(3) . . . . ? O5 S1 C11 C12 -126.2(3) . . . . ? O6 S1 C11 C10 175.7(3) . . . . ? O7 S1 C11 C10 -60.4(3) . . . . ? O5 S1 C11 C10 55.2(3) . . . . ? C10 C11 C12 C7 0.2(6) . . . . ? S1 C11 C12 C7 -178.3(3) . . . . ? C8 C7 C12 C11 -1.1(5) . . . . ? C13 C7 C12 C11 178.3(3) . . . . ? Cd1 O2 C13 O1 2.9(3) . . . . ? Cd1 O2 C13 C7 -174.3(3) . . . . ? Cd1 O1 C13 O2 -3.4(4) . . . . ? Cd2 O1 C13 O2 110.1(3) . . . . ? Cd1 O1 C13 C7 173.9(3) . . . . ? Cd2 O1 C13 C7 -72.6(4) . . . . ? C8 C7 C13 O2 -15.5(5) . . . . ? C12 C7 C13 O2 165.1(4) . . . . ? C8 C7 C13 O1 167.1(3) . . . . ? C12 C7 C13 O1 -12.3(5) . . . . ? Cd2 O4 C14 O3 -32.1(8) 1_445 . . . ? Cd2 O4 C14 C9 151.6(4) 1_445 . . . ? Cd1 O3 C14 O4 -15.6(5) 1_445 . . . ? Cd1 O3 C14 C9 160.7(2) 1_445 . . . ? C10 C9 C14 O4 20.9(5) . . . . ? C8 C9 C14 O4 -159.2(4) . . . . ? C10 C9 C14 O3 -155.8(3) . . . . ? C8 C9 C14 O3 24.2(5) . . . . ? 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 O8 H1W O7 0.851(19) 2.30(2) 2.757(5) 114.4(18) 2_766 O8 H2W O8 0.850(19) 2.368(13) 2.843(9) 115.8(11) 2_877 O9 H3W O2 0.86(2) 2.41(2) 2.964(5) 123(2) 2_766 O9 H4W O8 0.85(2) 2.02(2) 2.867(7) 174(7) 2_876 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.046 _refine_diff_density_min -0.598 _refine_diff_density_rms 0.102 ###====== _database_code_depnum_ccdc_archive 'CCDC 968333'