# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Inorg.Chem.Commun. _journal_coden_cambridge 1295 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ; Department of Chemistry, Faculty of Arts and Sciences, Eskisehir Osmangazi University, 26040 Eskisehir, Turkey ; _publ_contact_author_email yesilel@ogu.edu.tr _publ_contact_author_fax '+90 2222397850' _publ_contact_author_phone '+90 222 2393750' _publ_contact_author_name 'Dr Okan Zafer Yesilel' loop_ _publ_author_name 'Yesilel Okan Zafer' 'Buyukgungor Orhan' 'Erer Hakan' data_okan28 _database_code_depnum_ccdc_archive 'CCDC 689384' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Cd N4 O4' _chemical_formula_weight 388.66 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 'P 21/c' 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 9.5891(5) _cell_length_b 16.8764(8) _cell_length_c 8.6411(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.031(4) _cell_angle_gamma 90.00 _cell_volume 1329.71(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 19294 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.06 _exptl_crystal_description prism _exptl_crystal_colour 'light brown' _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.207 _exptl_crystal_size_min 0.130 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.941 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 1.665 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.6665 _exptl_absorpt_correction_T_max 0.8146 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10664 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2620 _reflns_number_gt 2398 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0322P)^2^+0.7040P] 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 2620 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0244 _refine_ls_R_factor_gt 0.0212 _refine_ls_wR_factor_ref 0.0574 _refine_ls_wR_factor_gt 0.0560 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0120(2) 0.12445(13) 0.5645(3) 0.0265(4) Uani 1 1 d . . . C2 C 0.0524(2) 0.07739(13) 0.8290(3) 0.0281(5) Uani 1 1 d . . . C3 C -0.1513(2) 0.02428(14) 0.6033(3) 0.0313(5) Uani 1 1 d . . . C4 C -0.1054(2) 0.07714(14) 0.4988(3) 0.0307(5) Uani 1 1 d . . . H4 H -0.1553 0.0789 0.3878 0.037 Uiso 1 1 calc R . . C5 C 0.0699(2) 0.17645(13) 0.4549(3) 0.0288(5) Uani 1 1 d . . . C6 C 0.4875(3) 0.10467(16) 0.8810(4) 0.0451(6) Uani 1 1 d . . . H6 H 0.4073 0.0729 0.8292 0.054 Uiso 1 1 calc R . . C7 C 0.6253(3) 0.07186(18) 0.9243(4) 0.0541(8) Uani 1 1 d . . . H7 H 0.6379 0.0188 0.9024 0.065 Uiso 1 1 calc R . . C8 C 0.7431(3) 0.1180(2) 0.9996(4) 0.0547(8) Uani 1 1 d . . . H8 H 0.8373 0.0968 1.0308 0.066 Uiso 1 1 calc R . . C9 C 0.7214(3) 0.19606(19) 1.0290(4) 0.0477(7) Uani 1 1 d . . . H9 H 0.8009 0.2284 1.0798 0.057 Uiso 1 1 calc R . . C10 C 0.5802(3) 0.22672(15) 0.9828(3) 0.0356(5) Uani 1 1 d . . . C11 C 0.5527(3) 0.31254(15) 1.0099(3) 0.0406(6) Uani 1 1 d . . . H11A H 0.6421 0.3357 1.0811 0.049 Uiso 1 1 calc R . . H11B H 0.4786 0.3159 1.0647 0.049 Uiso 1 1 calc R . . C12 C 0.5021(3) 0.36091(15) 0.8529(3) 0.0400(6) Uani 1 1 d . . . H12A H 0.5228 0.4165 0.8778 0.048 Uiso 1 1 calc R . . H12B H 0.5561 0.3443 0.7803 0.048 Uiso 1 1 calc R . . N1 N 0.0891(2) 0.12758(11) 0.7255(2) 0.0279(4) Uani 1 1 d . . . N2 N -0.0653(2) 0.02737(11) 0.7648(2) 0.0314(4) Uani 1 1 d . . . H2 H -0.0871 -0.0048 0.8310 0.038 Uiso 1 1 calc R . . N3 N 0.4641(2) 0.18091(12) 0.9106(3) 0.0350(5) Uani 1 1 d . . . N4 N 0.3444(2) 0.35043(12) 0.7716(3) 0.0347(4) Uani 1 1 d . . . H4A H 0.3283 0.3577 0.6643 0.042 Uiso 1 1 calc R . . H4B H 0.2975 0.3898 0.8055 0.042 Uiso 1 1 calc R . . O1 O 0.1765(2) 0.22242(10) 0.5249(2) 0.0365(4) Uani 1 1 d . . . O2 O 0.0185(2) 0.17181(11) 0.3062(2) 0.0407(4) Uani 1 1 d . . . O3 O 0.12089(19) 0.07439(10) 0.9763(2) 0.0375(4) Uani 1 1 d . . . O4 O -0.25629(19) -0.02143(11) 0.5589(2) 0.0451(5) Uani 1 1 d . . . Cd1 Cd 0.233415(17) 0.233945(10) 0.802337(19) 0.02792(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0292(10) 0.0226(10) 0.0301(11) -0.0007(9) 0.0126(9) 0.0000(8) C2 0.0331(11) 0.0223(10) 0.0318(12) -0.0003(9) 0.0144(9) -0.0013(9) C3 0.0294(11) 0.0269(11) 0.0386(13) 0.0005(10) 0.0119(10) -0.0007(9) C4 0.0310(11) 0.0299(12) 0.0305(11) 0.0012(9) 0.0086(9) -0.0021(9) C5 0.0314(11) 0.0267(11) 0.0297(12) 0.0007(9) 0.0118(9) 0.0006(9) C6 0.0456(15) 0.0324(14) 0.0588(18) 0.0029(12) 0.0181(13) 0.0025(11) C7 0.0596(18) 0.0373(15) 0.068(2) 0.0093(14) 0.0231(15) 0.0191(13) C8 0.0426(15) 0.0609(19) 0.0601(19) 0.0117(15) 0.0152(14) 0.0195(14) C9 0.0328(13) 0.0561(17) 0.0496(16) 0.0040(14) 0.0060(11) 0.0048(12) C10 0.0339(12) 0.0404(14) 0.0307(12) 0.0015(10) 0.0075(10) 0.0015(10) C11 0.0364(13) 0.0393(14) 0.0407(14) -0.0106(11) 0.0042(11) -0.0018(10) C12 0.0379(13) 0.0315(13) 0.0526(16) -0.0025(11) 0.0170(12) -0.0064(10) N1 0.0322(9) 0.0234(9) 0.0294(10) -0.0012(8) 0.0112(8) -0.0059(7) N2 0.0341(10) 0.0275(10) 0.0347(11) 0.0045(8) 0.0138(8) -0.0053(8) N3 0.0334(10) 0.0304(11) 0.0414(11) 0.0023(9) 0.0122(9) 0.0041(8) N4 0.0416(11) 0.0247(10) 0.0368(11) -0.0007(8) 0.0108(9) 0.0005(8) O1 0.0507(10) 0.0349(9) 0.0285(8) -0.0028(7) 0.0190(8) -0.0155(8) O2 0.0438(10) 0.0483(11) 0.0281(9) 0.0062(8) 0.0086(7) -0.0088(8) O3 0.0457(9) 0.0368(9) 0.0289(9) 0.0054(7) 0.0098(7) -0.0084(8) O4 0.0376(10) 0.0422(10) 0.0498(11) 0.0070(9) 0.0052(8) -0.0157(8) Cd1 0.02935(11) 0.02697(11) 0.02961(11) -0.00461(6) 0.01230(7) -0.00204(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C4 1.353(3) . ? C1 N1 1.360(3) . ? C1 C5 1.517(3) . ? C2 O3 1.240(3) . ? C2 N1 1.355(3) . ? C2 N2 1.381(3) . ? C3 O4 1.232(3) . ? C3 N2 1.384(3) . ? C3 C4 1.433(3) . ? C4 H4 0.9300 . ? C5 O2 1.228(3) . ? C5 O1 1.276(3) . ? C6 N3 1.344(3) . ? C6 C7 1.374(4) . ? C6 H6 0.9300 . ? C7 C8 1.361(5) . ? C7 H7 0.9300 . ? C8 C9 1.370(5) . ? C8 H8 0.9300 . ? C9 C10 1.388(4) . ? C9 H9 0.9300 . ? C10 N3 1.340(3) . ? C10 C11 1.503(4) . ? C11 C12 1.528(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N4 1.468(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? N1 Cd1 2.2379(18) . y N2 H2 0.8600 . ? N3 Cd1 2.300(2) . y N4 Cd1 2.290(2) . y N4 H4A 0.9000 . ? N4 H4B 0.9000 . ? O1 Cd1 2.2781(17) 4_565 y O1 Cd1 2.2960(17) . y O2 Cd1 2.6115(18) 4_565 y Cd1 O1 2.2781(17) 4_566 y Cd1 O2 2.6115(18) 4_566 y 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 C4 C1 N1 124.8(2) . . ? C4 C1 C5 119.8(2) . . ? N1 C1 C5 115.34(19) . . ? O3 C2 N1 122.7(2) . . ? O3 C2 N2 119.7(2) . . ? N1 C2 N2 117.7(2) . . ? O4 C3 N2 120.8(2) . . ? O4 C3 C4 125.1(2) . . ? N2 C3 C4 114.1(2) . . ? C1 C4 C3 118.8(2) . . ? C1 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? O2 C5 O1 122.5(2) . . ? O2 C5 C1 120.7(2) . . ? O1 C5 C1 116.7(2) . . ? N3 C6 C7 122.5(3) . . ? N3 C6 H6 118.8 . . ? C7 C6 H6 118.8 . . ? C8 C7 C6 119.1(3) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C7 C8 C9 119.2(3) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C8 C9 C10 119.8(3) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? N3 C10 C9 121.0(2) . . ? N3 C10 C11 117.9(2) . . ? C9 C10 C11 121.1(2) . . ? C10 C11 C12 113.5(2) . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? N4 C12 C11 110.9(2) . . ? N4 C12 H12A 109.5 . . ? C11 C12 H12A 109.5 . . ? N4 C12 H12B 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 108.0 . . ? C2 N1 C1 118.73(18) . . ? C2 N1 Cd1 124.68(15) . . ? C1 N1 Cd1 115.16(14) . . ? C2 N2 C3 125.9(2) . . ? C2 N2 H2 117.1 . . ? C3 N2 H2 117.1 . . ? C10 N3 C6 118.5(2) . . ? C10 N3 Cd1 121.38(16) . . ? C6 N3 Cd1 119.42(18) . . ? C12 N4 Cd1 119.66(15) . . ? C12 N4 H4A 107.4 . . ? Cd1 N4 H4A 107.4 . . ? C12 N4 H4B 107.4 . . ? Cd1 N4 H4B 107.4 . . ? H4A N4 H4B 106.9 . . ? C5 O1 Cd1 99.33(14) . 4_565 ? C5 O1 Cd1 116.30(14) . . ? Cd1 O1 Cd1 144.34(8) 4_565 . ? C5 O2 Cd1 84.93(14) . 4_565 ? N1 Cd1 O1 102.83(7) . 4_566 y N1 Cd1 N4 157.08(7) . . y O1 Cd1 N4 93.55(7) 4_566 . y N1 Cd1 O1 72.37(6) . . y O1 Cd1 O1 150.14(8) 4_566 . y N4 Cd1 O1 85.43(7) . . y N1 Cd1 N3 103.71(7) . . y O1 Cd1 N3 103.53(7) 4_566 . y N4 Cd1 N3 87.61(7) . . y O1 Cd1 N3 106.24(7) . . y N1 Cd1 O2 94.27(7) . 4_566 y O1 Cd1 O2 52.85(6) 4_566 4_566 y N4 Cd1 O2 82.84(7) . 4_566 y O1 Cd1 O2 97.55(6) . 4_566 y N3 Cd1 O2 153.55(7) . 4_566 y 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 C1 C4 C3 -1.9(3) . . . . ? C5 C1 C4 C3 175.4(2) . . . . ? O4 C3 C4 C1 179.7(2) . . . . ? N2 C3 C4 C1 -0.9(3) . . . . ? C4 C1 C5 O2 -5.5(3) . . . . ? N1 C1 C5 O2 172.1(2) . . . . ? C4 C1 C5 O1 176.8(2) . . . . ? N1 C1 C5 O1 -5.6(3) . . . . ? N3 C6 C7 C8 -0.2(5) . . . . ? C6 C7 C8 C9 -0.6(5) . . . . ? C7 C8 C9 C10 0.4(5) . . . . ? C8 C9 C10 N3 0.5(5) . . . . ? C8 C9 C10 C11 -178.7(3) . . . . ? N3 C10 C11 C12 -69.7(3) . . . . ? C9 C10 C11 C12 109.5(3) . . . . ? C10 C11 C12 N4 81.4(3) . . . . ? O3 C2 N1 C1 177.1(2) . . . . ? N2 C2 N1 C1 -2.0(3) . . . . ? O3 C2 N1 Cd1 -17.3(3) . . . . ? N2 C2 N1 Cd1 163.62(15) . . . . ? C4 C1 N1 C2 3.5(3) . . . . ? C5 C1 N1 C2 -173.93(19) . . . . ? C4 C1 N1 Cd1 -163.49(18) . . . . ? C5 C1 N1 Cd1 19.1(2) . . . . ? O3 C2 N2 C3 180.0(2) . . . . ? N1 C2 N2 C3 -0.8(3) . . . . ? O4 C3 N2 C2 -178.3(2) . . . . ? C4 C3 N2 C2 2.3(3) . . . . ? C9 C10 N3 C6 -1.3(4) . . . . ? C11 C10 N3 C6 177.9(2) . . . . ? C9 C10 N3 Cd1 -171.7(2) . . . . ? C11 C10 N3 Cd1 7.6(3) . . . . ? C7 C6 N3 C10 1.1(4) . . . . ? C7 C6 N3 Cd1 171.7(2) . . . . ? C11 C12 N4 Cd1 -29.3(3) . . . . ? O2 C5 O1 Cd1 -6.5(3) . . . 4_565 ? C1 C5 O1 Cd1 171.19(16) . . . 4_565 ? O2 C5 O1 Cd1 171.87(18) . . . . ? C1 C5 O1 Cd1 -10.5(3) . . . . ? O1 C5 O2 Cd1 5.6(2) . . . 4_565 ? C1 C5 O2 Cd1 -171.98(19) . . . 4_565 ? C2 N1 Cd1 O1 -34.54(19) . . . 4_566 ? C1 N1 Cd1 O1 131.58(15) . . . 4_566 ? C2 N1 Cd1 N4 -169.09(18) . . . . ? C1 N1 Cd1 N4 -3.0(3) . . . . ? C2 N1 Cd1 O1 176.04(19) . . . . ? C1 N1 Cd1 O1 -17.84(15) . . . . ? C2 N1 Cd1 N3 73.07(19) . . . . ? C1 N1 Cd1 N3 -120.81(16) . . . . ? C2 N1 Cd1 O2 -87.38(18) . . . 4_566 ? C1 N1 Cd1 O2 78.74(16) . . . 4_566 ? C12 N4 Cd1 N1 -133.7(2) . . . . ? C12 N4 Cd1 O1 90.46(19) . . . 4_566 ? C12 N4 Cd1 O1 -119.46(19) . . . . ? C12 N4 Cd1 N3 -12.96(19) . . . . ? C12 N4 Cd1 O2 142.32(19) . . . 4_566 ? C5 O1 Cd1 N1 15.18(16) . . . . ? Cd1 O1 Cd1 N1 -167.60(18) 4_565 . . . ? C5 O1 Cd1 O1 -69.90(13) . . . 4_566 ? Cd1 O1 Cd1 O1 107.3(2) 4_565 . . 4_566 ? C5 O1 Cd1 N4 -159.07(18) . . . . ? Cd1 O1 Cd1 N4 18.16(16) 4_565 . . . ? C5 O1 Cd1 N3 114.76(17) . . . . ? Cd1 O1 Cd1 N3 -68.02(17) 4_565 . . . ? C5 O1 Cd1 O2 -76.92(17) . . . 4_566 ? Cd1 O1 Cd1 O2 100.30(16) 4_565 . . 4_566 ? C10 N3 Cd1 N1 -174.44(19) . . . . ? C6 N3 Cd1 N1 15.2(2) . . . . ? C10 N3 Cd1 O1 -67.4(2) . . . 4_566 ? C6 N3 Cd1 O1 122.3(2) . . . 4_566 ? C10 N3 Cd1 N4 25.7(2) . . . . ? C6 N3 Cd1 N4 -144.6(2) . . . . ? C10 N3 Cd1 O1 110.3(2) . . . . ? C6 N3 Cd1 O1 -60.1(2) . . . . ? C10 N3 Cd1 O2 -43.0(3) . . . 4_566 ? C6 N3 Cd1 O2 146.73(19) . . . 4_566 ? 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 N2 H2 O3 0.86 2.14 2.997(3) 171.6 3_557 N4 H4A O3 0.90 2.43 3.054(3) 126.6 4_565 N4 H4B O4 0.90 2.02 2.881(3) 161.0 2_556 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.592 _refine_diff_density_min -0.739 _refine_diff_density_rms 0.065 data_okan29 _database_code_depnum_ccdc_archive 'CCDC 689385' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H22 Cd N4 O6' _chemical_formula_weight 418.73 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 'P 21/c' 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 10.6762(3) _cell_length_b 14.9236(5) _cell_length_c 10.2986(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.463(2) _cell_angle_gamma 90.00 _cell_volume 1633.40(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 43337 _cell_measurement_theta_min 1.36 _cell_measurement_theta_max 28.07 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.340 _exptl_crystal_size_mid 0.287 _exptl_crystal_size_min 0.190 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.703 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 1.370 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.3607 _exptl_absorpt_correction_T_max 0.7568 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28229 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3225 _reflns_number_gt 2966 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0361P)^2^+0.7871P] 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 0.0071(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3225 _refine_ls_number_parameters 240 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0264 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0622 _refine_ls_wR_factor_gt 0.0608 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.065 _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 C1 C 0.8498(2) 0.56916(14) 0.5428(2) 0.0324(4) Uani 1 1 d . . . C2 C 0.8859(2) 0.46435(15) 0.7087(2) 0.0412(5) Uani 1 1 d . . . C3 C 0.8505(2) 0.41460(15) 0.4824(2) 0.0388(5) Uani 1 1 d . . . C4 C 0.8396(2) 0.50624(15) 0.4472(2) 0.0376(5) Uani 1 1 d . . . H4 H 0.8256 0.5230 0.3600 0.045 Uiso 1 1 calc R . . C5 C 0.8380(2) 0.66814(13) 0.5100(2) 0.0351(5) Uani 1 1 d . B . C6 C 0.7233(4) 0.5698(2) 1.0351(3) 0.0734(9) Uani 1 1 d . . . H6A H 0.7240 0.5670 1.1293 0.088 Uiso 1 1 calc R A 1 H6B H 0.7021 0.5105 1.0013 0.088 Uiso 1 1 calc R A 1 C7A C 0.6120(6) 0.6392(5) 0.9793(6) 0.0602(19) Uani 0.447(5) 1 d P B 1 H7A1 H 0.5302 0.6181 0.9998 0.072 Uiso 0.447(5) 1 calc PR B 1 H7A2 H 0.6265 0.6985 1.0162 0.072 Uiso 0.447(5) 1 calc PR B 1 C8A C 0.5402(10) 0.5783(9) 0.7699(10) 0.101(3) Uani 0.447(5) 1 d P B 1 H8A1 H 0.4589 0.5831 0.8040 0.121 Uiso 0.447(5) 1 calc PR B 1 H8A2 H 0.5727 0.5189 0.7917 0.121 Uiso 0.447(5) 1 calc PR B 1 C9A C 0.5205(10) 0.5854(8) 0.6262(10) 0.101(3) Uani 0.447(5) 1 d P B 1 H9A1 H 0.4634 0.5394 0.5927 0.152 Uiso 0.447(5) 1 calc PR B 1 H9A2 H 0.5996 0.5783 0.5901 0.152 Uiso 0.447(5) 1 calc PR B 1 H9A3 H 0.4858 0.6431 0.6025 0.152 Uiso 0.447(5) 1 calc PR B 1 C10A C 0.5537(12) 0.7367(9) 0.8064(17) 0.098(3) Uani 0.447(5) 1 d PD B 1 H10A H 0.6064 0.7801 0.8558 0.117 Uiso 0.447(5) 1 calc PR B 1 H10B H 0.5600 0.7499 0.7151 0.117 Uiso 0.447(5) 1 calc PR B 1 C11A C 0.4175(8) 0.7581(8) 0.8324(10) 0.098(3) Uani 0.447(5) 1 d P B 1 H11A H 0.3987 0.8193 0.8090 0.147 Uiso 0.447(5) 1 calc PR B 1 H11B H 0.4078 0.7494 0.9232 0.147 Uiso 0.447(5) 1 calc PR B 1 H11C H 0.3610 0.7191 0.7811 0.147 Uiso 0.447(5) 1 calc PR B 1 C7B C 0.6440(6) 0.5530(4) 0.9197(6) 0.0661(16) Uani 0.553(5) 1 d P B 2 H7B1 H 0.5641 0.5299 0.9426 0.079 Uiso 0.553(5) 1 calc PR B 2 H7B2 H 0.6822 0.5075 0.8690 0.079 Uiso 0.553(5) 1 calc PR B 2 C8B C 0.5762(6) 0.6012(6) 0.7005(9) 0.0870(17) Uani 0.553(5) 1 d P B 2 H8B1 H 0.5792 0.6478 0.6352 0.104 Uiso 0.553(5) 1 calc PR B 2 H8B2 H 0.6341 0.5543 0.6801 0.104 Uiso 0.553(5) 1 calc PR B 2 C9B C 0.4436(6) 0.5626(6) 0.6919(7) 0.0870(17) Uani 0.553(5) 1 d P B 2 H9B1 H 0.4214 0.5398 0.6056 0.130 Uiso 0.553(5) 1 calc PR B 2 H9B2 H 0.3853 0.6088 0.7107 0.130 Uiso 0.553(5) 1 calc PR B 2 H9B3 H 0.4404 0.5150 0.7541 0.130 Uiso 0.553(5) 1 calc PR B 2 C10B C 0.5573(6) 0.7005(5) 0.8897(7) 0.0686(17) Uani 0.553(5) 1 d P B 2 H10C H 0.6041 0.7188 0.9708 0.082 Uiso 0.553(5) 1 calc PR B 2 H10D H 0.4777 0.6756 0.9103 0.082 Uiso 0.553(5) 1 calc PR B 2 C11B C 0.5336(9) 0.7808(7) 0.8026(9) 0.084(2) Uani 0.553(5) 1 d P B 2 H11D H 0.4877 0.8251 0.8463 0.127 Uiso 0.553(5) 1 calc PR B 2 H11E H 0.4854 0.7630 0.7234 0.127 Uiso 0.553(5) 1 calc PR B 2 H11F H 0.6124 0.8055 0.7825 0.127 Uiso 0.553(5) 1 calc PR B 2 N1 N 0.87043(19) 0.55065(12) 0.67189(18) 0.0379(4) Uani 1 1 d . . . N2 N 0.87362(19) 0.39920(12) 0.61392(18) 0.0389(4) Uani 1 1 d . . . H2 H 0.8810 0.3443 0.6391 0.047 Uiso 1 1 calc R . . N3 N 0.8487(3) 0.59160(17) 1.0038(2) 0.0628(6) Uani 1 1 d . . . H3A H 0.8928 0.5407 0.9975 0.075 Uiso 1 1 calc R . . H3B H 0.8876 0.6245 1.0688 0.075 Uiso 1 1 calc R . . N4 N 0.6201(3) 0.6403(2) 0.8338(3) 0.0696(8) Uani 1 1 d D . . O1 O 0.82751(18) 0.72200(11) 0.60179(16) 0.0469(4) Uani 1 1 d . . . O2 O 0.83855(18) 0.68863(11) 0.39227(16) 0.0440(4) Uani 1 1 d . . . O3 O 0.9092(2) 0.44135(12) 0.82447(17) 0.0642(6) Uani 1 1 d . . . O4 O 0.8409(2) 0.34964(12) 0.40623(18) 0.0564(5) Uani 1 1 d . . . O5 O 1.06652(19) 0.70161(14) 0.81954(19) 0.0520(4) Uani 1 1 d D . . H5A H 1.113(3) 0.678(2) 0.883(2) 0.078 Uiso 1 1 d D . . H5B H 1.089(3) 0.679(2) 0.751(2) 0.078 Uiso 1 1 d D . . O6 O 1.2243(3) 0.67393(14) 1.0378(2) 0.0730(7) Uani 1 1 d D . . H6C H 1.210(4) 0.7271(14) 1.062(4) 0.109 Uiso 1 1 d D . . H6D H 1.182(4) 0.637(2) 1.080(4) 0.109 Uiso 1 1 d D . . Cd1 Cd 0.846734(17) 0.668968(10) 0.813927(15) 0.04008(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0400(11) 0.0279(10) 0.0300(10) 0.0009(8) 0.0064(8) 0.0000(8) C2 0.0621(14) 0.0276(11) 0.0338(11) 0.0000(9) 0.0029(10) 0.0000(10) C3 0.0516(13) 0.0315(11) 0.0344(11) -0.0033(9) 0.0098(9) -0.0014(9) C4 0.0515(12) 0.0315(11) 0.0300(10) 0.0011(9) 0.0043(9) -0.0007(9) C5 0.0432(11) 0.0284(11) 0.0339(11) 0.0049(8) 0.0052(9) 0.0013(8) C6 0.116(3) 0.0571(18) 0.0505(17) 0.0112(14) 0.0242(17) -0.0179(18) C7A 0.062(4) 0.073(4) 0.049(4) -0.002(3) 0.021(3) -0.017(3) C8A 0.085(4) 0.135(7) 0.087(5) -0.036(4) 0.022(4) -0.051(4) C9A 0.085(4) 0.135(7) 0.087(5) -0.036(4) 0.022(4) -0.051(4) C10A 0.060(4) 0.131(8) 0.102(6) 0.003(6) 0.007(4) 0.016(4) C11A 0.060(4) 0.131(8) 0.102(6) 0.003(6) 0.007(4) 0.016(4) C7B 0.073(4) 0.051(3) 0.077(4) 0.010(3) 0.021(3) -0.026(3) C8B 0.053(3) 0.120(5) 0.086(4) -0.023(3) 0.000(2) -0.028(3) C9B 0.053(3) 0.120(5) 0.086(4) -0.023(3) 0.000(2) -0.028(3) C10B 0.066(4) 0.081(4) 0.061(4) 0.005(3) 0.017(3) 0.002(3) C11B 0.068(5) 0.106(7) 0.078(5) 0.013(5) 0.004(3) 0.016(4) N1 0.0624(12) 0.0241(9) 0.0270(9) 0.0000(7) 0.0042(8) 0.0008(8) N2 0.0612(12) 0.0223(8) 0.0338(9) 0.0014(7) 0.0076(8) 0.0004(8) N3 0.0974(19) 0.0482(13) 0.0415(12) 0.0074(10) -0.0002(12) -0.0110(13) N4 0.0681(16) 0.092(2) 0.0479(14) 0.0053(14) 0.0037(12) -0.0348(15) O1 0.0781(12) 0.0267(8) 0.0369(9) 0.0020(7) 0.0102(8) 0.0063(8) O2 0.0687(11) 0.0295(8) 0.0346(8) 0.0069(6) 0.0090(7) 0.0033(7) O3 0.1238(18) 0.0347(10) 0.0318(9) 0.0063(7) -0.0048(9) 0.0026(10) O4 0.0988(15) 0.0325(9) 0.0397(10) -0.0105(7) 0.0152(9) -0.0038(9) O5 0.0622(12) 0.0531(11) 0.0415(10) -0.0109(9) 0.0097(8) -0.0030(9) O6 0.1094(19) 0.0497(13) 0.0597(14) 0.0038(10) 0.0075(13) 0.0054(12) Cd1 0.05986(13) 0.02872(12) 0.03259(12) -0.00401(6) 0.00930(8) -0.00315(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.355(3) . ? C1 C4 1.358(3) . ? C1 C5 1.518(3) . ? C2 O3 1.243(3) . ? C2 N1 1.348(3) . ? C2 N2 1.375(3) . ? C3 O4 1.245(3) . ? C3 N2 1.372(3) . ? C3 C4 1.417(3) . ? C4 H4 0.9300 . ? C5 O2 1.251(3) . ? C5 O1 1.254(3) . ? C6 C7B 1.414(7) . ? C6 N3 1.444(4) . ? C6 C7A 1.638(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7A N4 1.509(7) . ? C7A H7A1 0.9700 . ? C7A H7A2 0.9700 . ? C8A N4 1.382(9) . ? C8A C9A 1.478(15) . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C9A H9A1 0.9600 . ? C9A H9A2 0.9600 . ? C9A H9A3 0.9600 . ? C10A C11A 1.537(15) . ? C10A N4 1.616(12) . ? C10A H10A 0.9700 . ? C10A H10B 0.9700 . ? C11A H11A 0.9600 . ? C11A H11B 0.9600 . ? C11A H11C 0.9600 . ? C7B N4 1.582(6) . ? C7B H7B1 0.9700 . ? C7B H7B2 0.9700 . ? C8B C9B 1.523(9) . ? C8B N4 1.524(9) . ? C8B H8B1 0.9700 . ? C8B H8B2 0.9700 . ? C9B H9B1 0.9600 . ? C9B H9B2 0.9600 . ? C9B H9B3 0.9600 . ? C10B N4 1.289(7) . ? C10B C11B 1.503(11) . ? C10B H10C 0.9700 . ? C10B H10D 0.9700 . ? C11B H11D 0.9600 . ? C11B H11E 0.9600 . ? C11B H11F 0.9600 . ? N1 Cd1 2.3220(18) . ? N2 H2 0.8600 . ? N3 Cd1 2.269(2) . y N3 H3A 0.9000 . ? N3 H3B 0.9000 . ? N4 Cd1 2.485(3) . y O1 Cd1 2.3143(16) . y O2 Cd1 2.2778(16) 4_575 y O5 Cd1 2.392(2) . y O5 H5A 0.855(18) . ? O5 H5B 0.843(18) . ? O6 H6C 0.852(19) . ? O6 H6D 0.851(19) . ? Cd1 O2 2.2778(16) 4_576 y loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C4 124.4(2) . . ? N1 C1 C5 114.79(18) . . ? C4 C1 C5 120.8(2) . . ? O3 C2 N1 122.8(2) . . ? O3 C2 N2 118.8(2) . . ? N1 C2 N2 118.4(2) . . ? O4 C3 N2 119.2(2) . . ? O4 C3 C4 126.1(2) . . ? N2 C3 C4 114.66(19) . . ? C1 C4 C3 118.8(2) . . ? C1 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? O2 C5 O1 125.67(19) . . ? O2 C5 C1 116.48(19) . . ? O1 C5 C1 117.84(19) . . ? C7B C6 N3 110.2(3) . . ? C7B C6 C7A 57.4(4) . . ? N3 C6 C7A 115.9(3) . . ? C7B C6 H6A 141.2 . . ? N3 C6 H6A 108.3 . . ? C7A C6 H6A 108.3 . . ? C7B C6 H6B 55.7 . . ? N3 C6 H6B 108.3 . . ? C7A C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? N4 C7A C6 104.3(4) . . ? N4 C7A H7A1 110.9 . . ? C6 C7A H7A1 110.9 . . ? N4 C7A H7A2 110.9 . . ? C6 C7A H7A2 110.9 . . ? H7A1 C7A H7A2 108.9 . . ? N4 C8A C9A 116.9(10) . . ? N4 C8A H8A1 108.1 . . ? C9A C8A H8A1 108.1 . . ? N4 C8A H8A2 108.1 . . ? C9A C8A H8A2 108.1 . . ? H8A1 C8A H8A2 107.3 . . ? C8A C9A H9A1 109.5 . . ? C8A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C8A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? C11A C10A N4 124.1(11) . . ? C11A C10A H10A 106.3 . . ? N4 C10A H10A 106.3 . . ? C11A C10A H10B 106.3 . . ? N4 C10A H10B 106.3 . . ? H10A C10A H10B 106.4 . . ? C10A C11A H11A 109.5 . . ? C10A C11A H11B 109.5 . . ? H11A C11A H11B 109.5 . . ? C10A C11A H11C 109.5 . . ? H11A C11A H11C 109.5 . . ? H11B C11A H11C 109.5 . . ? C6 C7B N4 112.1(4) . . ? C6 C7B H7B1 109.2 . . ? N4 C7B H7B1 109.2 . . ? C6 C7B H7B2 109.2 . . ? N4 C7B H7B2 109.2 . . ? H7B1 C7B H7B2 107.9 . . ? C9B C8B N4 113.7(6) . . ? C9B C8B H8B1 108.8 . . ? N4 C8B H8B1 108.8 . . ? C9B C8B H8B2 108.8 . . ? N4 C8B H8B2 108.8 . . ? H8B1 C8B H8B2 107.7 . . ? C8B C9B H9B1 109.5 . . ? C8B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C8B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? N4 C10B C11B 110.8(6) . . ? N4 C10B H10C 109.5 . . ? C11B C10B H10C 109.5 . . ? N4 C10B H10D 109.5 . . ? C11B C10B H10D 109.5 . . ? H10C C10B H10D 108.1 . . ? C10B C11B H11D 109.5 . . ? C10B C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? C10B C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? C2 N1 C1 118.32(18) . . ? C2 N1 Cd1 124.56(14) . . ? C1 N1 Cd1 116.47(14) . . ? C3 N2 C2 125.29(19) . . ? C3 N2 H2 117.4 . . ? C2 N2 H2 117.4 . . ? C6 N3 Cd1 112.0(2) . . ? C6 N3 H3A 109.2 . . ? Cd1 N3 H3A 109.2 . . ? C6 N3 H3B 109.2 . . ? Cd1 N3 H3B 109.2 . . ? H3A N3 H3B 107.9 . . ? C10B N4 C8A 110.9(6) . . ? C10B N4 C7A 58.9(4) . . ? C8A N4 C7A 112.0(6) . . ? C10B N4 C8B 122.7(5) . . ? C8A N4 C8B 36.1(5) . . ? C7A N4 C8B 148.1(5) . . ? C10B N4 C7B 112.8(4) . . ? C8A N4 C7B 77.0(6) . . ? C7A N4 C7B 57.1(4) . . ? C8B N4 C7B 102.0(5) . . ? C10B N4 C10A 38.7(6) . . ? C8A N4 C10A 105.8(8) . . ? C7A N4 C10A 96.8(7) . . ? C8B N4 C10A 95.2(7) . . ? C7B N4 C10A 151.1(7) . . ? C10B N4 Cd1 117.9(4) . . ? C8A N4 Cd1 129.6(5) . . ? C7A N4 Cd1 103.4(3) . . ? C8B N4 Cd1 102.1(3) . . ? C7B N4 Cd1 94.7(2) . . ? C10A N4 Cd1 104.3(5) . . ? C5 O1 Cd1 119.10(14) . . ? C5 O2 Cd1 125.11(14) . 4_575 ? Cd1 O5 H5A 115(3) . . ? Cd1 O5 H5B 105(3) . . ? H5A O5 H5B 107(3) . . ? H6C O6 H6D 109(3) . . ? N3 Cd1 O2 99.61(8) . 4_576 y N3 Cd1 O1 168.57(8) . . y O2 Cd1 O1 90.71(6) 4_576 . y N3 Cd1 N1 99.40(8) . . y O2 Cd1 N1 160.52(6) 4_576 . y O1 Cd1 N1 70.76(6) . . y N3 Cd1 O5 98.88(9) . . y O2 Cd1 O5 82.65(7) 4_576 . y O1 Cd1 O5 87.24(7) . . y N1 Cd1 O5 90.26(7) . . y N3 Cd1 N4 76.72(10) . . y O2 Cd1 N4 93.50(9) 4_576 . y O1 Cd1 N4 97.89(8) . . y N1 Cd1 N4 94.95(9) . . y O5 Cd1 N4 173.65(7) . . y 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 C1 C4 C3 0.2(4) . . . . ? C5 C1 C4 C3 -179.7(2) . . . . ? O4 C3 C4 C1 178.6(2) . . . . ? N2 C3 C4 C1 -1.3(3) . . . . ? N1 C1 C5 O2 169.3(2) . . . . ? C4 C1 C5 O2 -10.9(3) . . . . ? N1 C1 C5 O1 -11.4(3) . . . . ? C4 C1 C5 O1 168.5(2) . . . . ? C7B C6 C7A N4 -41.3(4) . . . . ? N3 C6 C7A N4 57.1(5) . . . . ? N3 C6 C7B N4 -67.3(5) . . . . ? C7A C6 C7B N4 41.2(4) . . . . ? O3 C2 N1 C1 177.6(3) . . . . ? N2 C2 N1 C1 -3.2(3) . . . . ? O3 C2 N1 Cd1 -12.0(4) . . . . ? N2 C2 N1 Cd1 167.17(16) . . . . ? C4 C1 N1 C2 2.2(4) . . . . ? C5 C1 N1 C2 -178.0(2) . . . . ? C4 C1 N1 Cd1 -169.00(18) . . . . ? C5 C1 N1 Cd1 10.9(2) . . . . ? O4 C3 N2 C2 -179.7(2) . . . . ? C4 C3 N2 C2 0.1(3) . . . . ? O3 C2 N2 C3 -178.6(2) . . . . ? N1 C2 N2 C3 2.2(4) . . . . ? C7B C6 N3 Cd1 34.3(4) . . . . ? C7A C6 N3 Cd1 -28.4(4) . . . . ? C11B C10B N4 C8A -94.0(8) . . . . ? C11B C10B N4 C7A 162.2(8) . . . . ? C11B C10B N4 C8B -55.5(8) . . . . ? C11B C10B N4 C7B -178.2(5) . . . . ? C11B C10B N4 C10A -4.6(11) . . . . ? C11B C10B N4 Cd1 73.0(7) . . . . ? C9A C8A N4 C10B 104.3(10) . . . . ? C9A C8A N4 C7A 168.0(9) . . . . ? C9A C8A N4 C8B -13.1(8) . . . . ? C9A C8A N4 C7B -146.0(11) . . . . ? C9A C8A N4 C10A 63.8(12) . . . . ? C9A C8A N4 Cd1 -60.7(13) . . . . ? C6 C7A N4 C10B -165.3(6) . . . . ? C6 C7A N4 C8A 92.9(7) . . . . ? C6 C7A N4 C8B 91.7(10) . . . . ? C6 C7A N4 C7B 36.3(4) . . . . ? C6 C7A N4 C10A -157.0(6) . . . . ? C6 C7A N4 Cd1 -50.6(4) . . . . ? C9B C8B N4 C10B -54.5(9) . . . . ? C9B C8B N4 C8A 26.1(11) . . . . ? C9B C8B N4 C7A 28.0(14) . . . . ? C9B C8B N4 C7B 72.9(7) . . . . ? C9B C8B N4 C10A -83.7(9) . . . . ? C9B C8B N4 Cd1 170.5(6) . . . . ? C6 C7B N4 C10B -65.8(6) . . . . ? C6 C7B N4 C8A -173.2(6) . . . . ? C6 C7B N4 C7A -45.8(5) . . . . ? C6 C7B N4 C8B 160.6(5) . . . . ? C6 C7B N4 C10A -74.0(13) . . . . ? C6 C7B N4 Cd1 57.1(4) . . . . ? C11A C10A N4 C10B -51.1(12) . . . . ? C11A C10A N4 C8A 52.8(15) . . . . ? C11A C10A N4 C7A -62.4(13) . . . . ? C11A C10A N4 C8B 87.9(13) . . . . ? C11A C10A N4 C7B -39(2) . . . . ? C11A C10A N4 Cd1 -168.1(11) . . . . ? O2 C5 O1 Cd1 -174.67(18) . . . . ? C1 C5 O1 Cd1 6.1(3) . . . . ? O1 C5 O2 Cd1 8.6(4) . . . 4_575 ? C1 C5 O2 Cd1 -172.10(14) . . . 4_575 ? C6 N3 Cd1 O2 90.0(2) . . . 4_576 ? C6 N3 Cd1 O1 -64.2(5) . . . . ? C6 N3 Cd1 N1 -94.2(2) . . . . ? C6 N3 Cd1 O5 174.0(2) . . . . ? C6 N3 Cd1 N4 -1.3(2) . . . . ? C5 O1 Cd1 N3 -31.8(5) . . . . ? C5 O1 Cd1 O2 173.53(18) . . . 4_576 ? C5 O1 Cd1 N1 -0.32(17) . . . . ? C5 O1 Cd1 O5 90.92(18) . . . . ? C5 O1 Cd1 N4 -92.84(19) . . . . ? C2 N1 Cd1 N3 -2.7(2) . . . . ? C1 N1 Cd1 N3 167.90(17) . . . . ? C2 N1 Cd1 O2 164.6(2) . . . 4_576 ? C1 N1 Cd1 O2 -24.8(3) . . . 4_576 ? C2 N1 Cd1 O1 -176.6(2) . . . . ? C1 N1 Cd1 O1 -6.07(16) . . . . ? C2 N1 Cd1 O5 96.4(2) . . . . ? C1 N1 Cd1 O5 -93.05(17) . . . . ? C2 N1 Cd1 N4 -80.0(2) . . . . ? C1 N1 Cd1 N4 90.58(17) . . . . ? C10B N4 Cd1 N3 92.7(4) . . . . ? C8A N4 Cd1 N3 -103.2(8) . . . . ? C7A N4 Cd1 N3 31.0(3) . . . . ? C8B N4 Cd1 N3 -129.6(4) . . . . ? C7B N4 Cd1 N3 -26.2(3) . . . . ? C10A N4 Cd1 N3 131.7(7) . . . . ? C10B N4 Cd1 O2 -6.4(4) . . . 4_576 ? C8A N4 Cd1 O2 157.7(8) . . . 4_576 ? C7A N4 Cd1 O2 -68.0(3) . . . 4_576 ? C8B N4 Cd1 O2 131.3(4) . . . 4_576 ? C7B N4 Cd1 O2 -125.3(3) . . . 4_576 ? C10A N4 Cd1 O2 32.7(6) . . . 4_576 ? C10B N4 Cd1 O1 -97.6(4) . . . . ? C8A N4 Cd1 O1 66.5(8) . . . . ? C7A N4 Cd1 O1 -159.2(3) . . . . ? C8B N4 Cd1 O1 40.1(4) . . . . ? C7B N4 Cd1 O1 143.5(3) . . . . ? C10A N4 Cd1 O1 -58.5(6) . . . . ? C10B N4 Cd1 N1 -168.8(4) . . . . ? C8A N4 Cd1 N1 -4.7(8) . . . . ? C7A N4 Cd1 N1 129.5(3) . . . . ? C8B N4 Cd1 N1 -31.1(4) . . . . ? C7B N4 Cd1 N1 72.3(3) . . . . ? C10A N4 Cd1 N1 -129.8(6) . . . . ? C10B N4 Cd1 O5 46.1(10) . . . . ? C8A N4 Cd1 O5 -149.8(10) . . . . ? C7A N4 Cd1 O5 -15.6(10) . . . . ? C8B N4 Cd1 O5 -176.2(8) . . . . ? C7B N4 Cd1 O5 -72.8(9) . . . . ? C10A N4 Cd1 O5 85.1(10) . . . . ? 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 N2 H2 O5 0.86 2.23 3.081(3) 168.4 2_746 N3 H3A O3 0.90 2.34 3.014(3) 132.0 . N3 H3B O1 0.90 2.41 2.975(3) 120.9 4_576 N3 H3B O3 0.90 2.53 3.030(4) 115.2 3_767 O5 H5A O6 0.855(18) 1.90(2) 2.709(3) 158(3) . O5 H5B O4 0.843(18) 1.89(2) 2.721(3) 168(4) 3_766 O6 H6C O4 0.852(19) 1.94(2) 2.788(3) 171(5) 2_756 O6 H6D O3 0.851(19) 1.868(19) 2.718(3) 178(4) 3_767 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.426 _refine_diff_density_min -0.625 _refine_diff_density_rms 0.058 data_okan42 _database_code_depnum_ccdc_archive 'CCDC 697764' _audit_update_record ; 2009-09-17 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H22 Cd2 N6 O14' _chemical_formula_weight 675.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.5073(5) _cell_length_b 9.4505(8) _cell_length_c 9.5670(9) _cell_angle_alpha 65.998(7) _cell_angle_beta 85.229(7) _cell_angle_gamma 72.619(7) _cell_volume 512.43(8) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10809 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.33 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.800 _exptl_crystal_size_mid 0.497 _exptl_crystal_size_min 0.270 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 2.159 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.2391 _exptl_absorpt_correction_T_max 0.5993 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4986 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 26.49 _reflns_number_total 2096 _reflns_number_gt 2048 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0268P)^2^+0.2152P] 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 2096 _refine_ls_number_parameters 164 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0222 _refine_ls_R_factor_gt 0.0213 _refine_ls_wR_factor_ref 0.0533 _refine_ls_wR_factor_gt 0.0528 _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_restrained_S_all 1.130 _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 C1 C 0.7948(4) 0.1979(3) 0.2296(3) 0.0275(4) Uani 1 1 d . . . C2 C 0.8194(3) 0.3834(3) -0.0345(3) 0.0271(4) Uani 1 1 d . . . C3 C 0.7470(3) 0.5115(3) 0.0166(3) 0.0265(4) Uani 1 1 d . . . H3 H 0.7306 0.6182 -0.0514 0.032 Uiso 1 1 calc R . . C4 C 0.7025(3) 0.4753(3) 0.1658(2) 0.0241(4) Uani 1 1 d . . . C5 C 0.3820(4) 0.3908(3) 0.7766(3) 0.0275(4) Uani 1 1 d . . . N1 N 0.7237(3) 0.3233(2) 0.2728(2) 0.0264(4) Uani 1 1 d . . . N2 N 0.8438(3) 0.2325(3) 0.0781(2) 0.0307(4) Uani 1 1 d . . . H2 H 0.8941 0.1517 0.0525 0.037 Uiso 1 1 calc R . . O1 O 0.8159(3) 0.0564(2) 0.3195(2) 0.0397(4) Uani 1 1 d . . . O2 O 0.8592(3) 0.3991(2) -0.16834(19) 0.0380(4) Uani 1 1 d . . . O3 O 0.4247(3) 0.4351(2) 0.6373(2) 0.0371(4) Uani 1 1 d . . . O4 O 0.4088(3) 0.2500(2) 0.8684(2) 0.0437(4) Uani 1 1 d . . . Cd1 Cd 0.59844(2) 0.282893(18) 0.507487(16) 0.02724(7) Uani 1 1 d . . . H5A H 0.153(4) 0.306(4) 0.474(3) 0.041 Uiso 1 1 d D . . H5B H 0.219(5) 0.401(3) 0.336(3) 0.041 Uiso 1 1 d D . . H6A H 0.909(5) 0.272(4) 0.705(3) 0.041 Uiso 1 1 d D . . H6B H 1.008(5) 0.147(2) 0.662(3) 0.041 Uiso 1 1 d D . . N3 N 0.6243(4) 0.0228(3) 0.6531(3) 0.0414(5) Uani 1 1 d . . . H3A H 0.4934 0.0092 0.6646 0.062 Uiso 1 1 calc R . . H3B H 0.6838 -0.0050 0.7445 0.062 Uiso 1 1 calc R . . H3C H 0.7059 -0.0392 0.6081 0.062 Uiso 1 1 calc R . . H7A H 0.658(4) 1.071(3) 0.943(4) 0.062 Uiso 1 1 d D . . H7B H 0.753(6) 0.909(3) 1.038(3) 0.062 Uiso 1 1 d D . . O5 O 0.2540(3) 0.3112(3) 0.4139(2) 0.0401(4) Uani 1 1 d D . . O6 O 0.9298(3) 0.2447(2) 0.6315(2) 0.0329(4) Uani 1 1 d D . . O7 O 0.7747(3) 0.9950(3) 0.9692(3) 0.0531(5) Uani 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 C1 0.0322(10) 0.0239(11) 0.0253(11) -0.0102(9) 0.0035(8) -0.0066(8) C2 0.0283(10) 0.0285(12) 0.0244(11) -0.0106(9) 0.0007(8) -0.0080(8) C3 0.0288(10) 0.0246(11) 0.0252(10) -0.0085(9) 0.0027(8) -0.0089(8) C4 0.0239(9) 0.0232(11) 0.0257(10) -0.0107(9) 0.0018(7) -0.0064(8) C5 0.0298(10) 0.0223(11) 0.0298(11) -0.0110(9) 0.0056(8) -0.0072(8) N1 0.0328(9) 0.0216(9) 0.0230(9) -0.0093(7) 0.0052(7) -0.0060(7) N2 0.0420(11) 0.0254(10) 0.0257(9) -0.0144(8) 0.0053(7) -0.0065(8) O1 0.0601(11) 0.0214(9) 0.0313(9) -0.0089(7) 0.0103(8) -0.0078(8) O2 0.0566(11) 0.0357(10) 0.0235(8) -0.0145(8) 0.0057(7) -0.0131(8) O3 0.0563(11) 0.0252(9) 0.0296(9) -0.0147(8) 0.0109(7) -0.0087(8) O4 0.0595(12) 0.0202(9) 0.0434(11) -0.0099(8) 0.0126(9) -0.0074(8) Cd1 0.03647(11) 0.02158(11) 0.02366(11) -0.01022(8) 0.00590(6) -0.00804(7) N3 0.0549(13) 0.0267(12) 0.0391(13) -0.0084(10) -0.0039(10) -0.0121(10) O5 0.0391(9) 0.0393(11) 0.0342(10) -0.0070(8) 0.0035(7) -0.0122(8) O6 0.0383(9) 0.0294(9) 0.0298(9) -0.0137(8) 0.0019(7) -0.0059(7) O7 0.0425(11) 0.0379(12) 0.0756(16) -0.0209(11) 0.0061(10) -0.0106(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 C1 O1 1.233(3) . ? C1 N1 1.352(3) . ? C1 N2 1.382(3) . ? C2 O2 1.242(3) . ? C2 N2 1.365(3) . ? C2 C3 1.425(3) . ? C3 C4 1.353(3) . ? C3 H3 0.9300 . ? C4 N1 1.356(3) . ? C4 C5 1.520(3) 2_666 ? C5 O4 1.228(3) . ? C5 O3 1.258(3) . ? C5 C4 1.520(3) 2_666 ? N1 Cd1 2.2441(18) . ? N2 H2 0.8600 . ? O3 Cd1 2.2668(16) . ? O3 Cd1 2.4156(19) 2_666 ? Cd1 N3 2.240(2) . ? Cd1 O5 2.3824(19) . ? Cd1 O6 2.4081(18) . ? Cd1 O3 2.4156(19) 2_666 ? N3 H3A 0.8900 . ? N3 H3B 0.8900 . ? N3 H3C 0.8900 . ? O5 H5A 0.838(17) . ? O5 H5B 0.852(17) . ? O6 H6A 0.825(17) . ? O6 H6B 0.850(17) . ? O7 H7A 0.845(18) . ? O7 H7B 0.852(18) . ? 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 C1 N1 122.6(2) . . ? O1 C1 N2 119.7(2) . . ? N1 C1 N2 117.7(2) . . ? O2 C2 N2 119.7(2) . . ? O2 C2 C3 125.9(2) . . ? N2 C2 C3 114.46(19) . . ? C4 C3 C2 118.9(2) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 N1 124.4(2) . . ? C3 C4 C5 120.4(2) . 2_666 ? N1 C4 C5 115.17(19) . 2_666 ? O4 C5 O3 125.5(2) . . ? O4 C5 C4 118.4(2) . 2_666 ? O3 C5 C4 116.1(2) . 2_666 ? C1 N1 C4 118.62(19) . . ? C1 N1 Cd1 120.06(16) . . ? C4 N1 Cd1 120.72(14) . . ? C2 N2 C1 125.79(19) . . ? C2 N2 H2 117.1 . . ? C1 N2 H2 117.1 . . ? C5 O3 Cd1 129.21(16) . . ? C5 O3 Cd1 118.01(15) . 2_666 ? Cd1 O3 Cd1 111.08(7) . 2_666 ? N3 Cd1 N1 113.26(8) . . ? N3 Cd1 O3 108.78(9) . . ? N1 Cd1 O3 137.74(7) . . ? N3 Cd1 O5 88.37(8) . . ? N1 Cd1 O5 89.26(7) . . ? O3 Cd1 O5 87.69(7) . . ? N3 Cd1 O6 88.13(8) . . ? N1 Cd1 O6 97.37(7) . . ? O3 Cd1 O6 88.04(7) . . ? O5 Cd1 O6 173.30(6) . . ? N3 Cd1 O3 176.91(7) . 2_666 ? N1 Cd1 O3 69.23(6) . 2_666 ? O3 Cd1 O3 68.92(7) . 2_666 ? O5 Cd1 O3 93.55(7) . 2_666 ? O6 Cd1 O3 89.71(7) . 2_666 ? Cd1 N3 H3A 109.5 . . ? Cd1 N3 H3B 109.5 . . ? H3A N3 H3B 109.5 . . ? Cd1 N3 H3C 109.5 . . ? H3A N3 H3C 109.5 . . ? H3B N3 H3C 109.5 . . ? Cd1 O5 H5A 118(2) . . ? Cd1 O5 H5B 107(2) . . ? H5A O5 H5B 109(2) . . ? Cd1 O6 H6A 112(2) . . ? Cd1 O6 H6B 111(2) . . ? H6A O6 H6B 109(2) . . ? H7A O7 H7B 110(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 O2 C2 C3 C4 177.5(2) . . . . ? N2 C2 C3 C4 -2.3(3) . . . . ? C2 C3 C4 N1 0.6(3) . . . . ? C2 C3 C4 C5 -177.99(19) . . . 2_666 ? O1 C1 N1 C4 -179.1(2) . . . . ? N2 C1 N1 C4 0.6(3) . . . . ? O1 C1 N1 Cd1 -8.0(3) . . . . ? N2 C1 N1 Cd1 171.76(15) . . . . ? C3 C4 N1 C1 0.3(3) . . . . ? C5 C4 N1 C1 178.9(2) 2_666 . . . ? C3 C4 N1 Cd1 -170.80(16) . . . . ? C5 C4 N1 Cd1 7.8(2) 2_666 . . . ? O2 C2 N2 C1 -176.4(2) . . . . ? C3 C2 N2 C1 3.4(3) . . . . ? O1 C1 N2 C2 177.1(2) . . . . ? N1 C1 N2 C2 -2.6(3) . . . . ? O4 C5 O3 Cd1 -8.0(4) . . . . ? C4 C5 O3 Cd1 169.84(15) 2_666 . . . ? O4 C5 O3 Cd1 -171.7(2) . . . 2_666 ? C4 C5 O3 Cd1 6.1(3) 2_666 . . 2_666 ? C1 N1 Cd1 N3 3.2(2) . . . . ? C4 N1 Cd1 N3 174.13(16) . . . . ? C1 N1 Cd1 O3 -170.49(16) . . . . ? C4 N1 Cd1 O3 0.5(2) . . . . ? C1 N1 Cd1 O5 -84.75(18) . . . . ? C4 N1 Cd1 O5 86.22(17) . . . . ? C1 N1 Cd1 O6 94.29(17) . . . . ? C4 N1 Cd1 O6 -94.74(16) . . . . ? C1 N1 Cd1 O3 -178.83(19) . . . 2_666 ? C4 N1 Cd1 O3 -7.86(15) . . . 2_666 ? C5 O3 Cd1 N3 13.2(2) . . . . ? Cd1 O3 Cd1 N3 177.80(8) 2_666 . . . ? C5 O3 Cd1 N1 -172.95(18) . . . . ? Cd1 O3 Cd1 N1 -8.35(15) 2_666 . . . ? C5 O3 Cd1 O5 100.7(2) . . . . ? Cd1 O3 Cd1 O5 -94.71(9) 2_666 . . . ? C5 O3 Cd1 O6 -74.1(2) . . . . ? Cd1 O3 Cd1 O6 90.45(9) 2_666 . . . ? C5 O3 Cd1 O3 -164.6(3) . . . 2_666 ? Cd1 O3 Cd1 O3 0.0 2_666 . . 2_666 ? 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 N2 H2 O7 0.86 2.23 2.899(3) 134.3 2_766 N2 H2 O7 0.86 2.28 2.985(3) 139.7 1_544 N3 H3A O1 0.89 2.25 3.135(3) 171.0 2_656 N3 H3B O7 0.89 2.28 3.141(4) 163.7 1_545 N3 H3C O5 0.89 2.60 3.327(3) 139.7 2_656 N3 H3C O1 0.89 2.64 3.255(3) 126.8 . O5 H5A O6 0.838(17) 2.035(18) 2.860(3) 168(3) 1_455 O5 H5B O2 0.852(17) 1.870(18) 2.722(3) 178(3) 2_665 O6 H6A O2 0.825(17) 1.982(18) 2.781(2) 163(3) 1_556 O6 H6B O1 0.850(17) 1.863(17) 2.699(3) 167(3) 2_756 O7 H7A O4 0.845(18) 1.891(18) 2.733(3) 175(4) 1_565 O7 H7B O4 0.852(18) 1.97(2) 2.760(3) 154(4) 2_667 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.540 _refine_diff_density_min -0.646 _refine_diff_density_rms 0.102