# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Prakash Kanoo' _publ_contact_author_email prakash@jncasr.ac.in loop_ _publ_author_name T.Maji 'Prakash Kanoo' 'Ritesh Haldar' S.Cyriac data_compound1 _database_code_depnum_ccdc_archive 'CCDC 830358' #TrackingRef '5877_web_deposit_cif_file_0_PrakashKanoo_1308291693.compound1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 N4 O8 Zn' _chemical_formula_weight 471.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.741(5) _cell_length_b 14.796(5) _cell_length_c 19.340(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 2501.3(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 32.0 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 1.024 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.85436 _exptl_absorpt_correction_T_max 0.95741 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15504 _diffrn_reflns_av_R_equivalents 0.0772 _diffrn_reflns_av_sigmaI/netI 0.1392 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 31.97 _reflns_number_total 8008 _reflns_number_gt 4083 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 1.4.1' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.1631P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(3) _refine_ls_number_reflns 8008 _refine_ls_number_parameters 264 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1677 _refine_ls_R_factor_gt 0.0860 _refine_ls_wR_factor_ref 0.2689 _refine_ls_wR_factor_gt 0.2200 _refine_ls_goodness_of_fit_ref 0.924 _refine_ls_restrained_S_all 0.924 _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 Zn1 Zn 0.63146(8) 0.95552(5) 0.07330(3) 0.0385(2) Uani 1 1 d . . . O4 O 0.0323(6) 0.9765(4) 0.5297(2) 0.0469(12) Uani 1 1 d . . . N2 N 0.6206(7) 1.0115(4) 0.3874(2) 0.0386(12) Uani 1 1 d . . . N3 N 0.4884(6) 1.0428(4) 0.4217(2) 0.0387(11) Uani 1 1 d . . . O3 O -0.0451(5) 1.0266(4) 0.4272(3) 0.0580(14) Uani 1 1 d . . . O2 O 0.5556(6) 0.9287(4) 0.5850(3) 0.0584(14) Uani 1 1 d . . . O1 O 0.6743(5) 1.0396(4) 0.5275(2) 0.0456(11) Uani 1 1 d . . . N4 N 0.4159(6) 1.3236(4) 0.4314(3) 0.0411(12) Uani 1 1 d . . . N1 N 0.6283(7) 0.9824(4) 0.1745(2) 0.0383(11) Uani 1 1 d . . . C13 C 0.3176(8) 0.9416(5) 0.4833(3) 0.0426(16) Uani 1 1 d . . . C3 C 0.6175(8) 1.0021(4) 0.3175(3) 0.0382(13) Uani 1 1 d . . . C12 C 0.4484(8) 0.9848(4) 0.4790(3) 0.0359(13) Uani 1 1 d . . . C6 C 0.4683(7) 1.1347(4) 0.4267(3) 0.0375(12) Uani 1 1 d . . . C10 C 0.3605(10) 1.1713(5) 0.4706(3) 0.0456(16) Uani 1 1 d . . . H10 H 0.3037 1.1341 0.4996 0.055 Uiso 1 1 calc R . . C4 C 0.7542(8) 0.9791(5) 0.2839(3) 0.0439(17) Uani 1 1 d . . . H4 H 0.8443 0.9712 0.3087 0.053 Uiso 1 1 calc R . . C9 C 0.3372(8) 1.2648(5) 0.4710(3) 0.0484(17) Uani 1 1 d . . . H9 H 0.2627 1.2879 0.5005 0.058 Uiso 1 1 calc R . . C14 C 0.1907(8) 0.9445(5) 0.4345(4) 0.0453(15) Uani 1 1 d . . . H14A H 0.1673 0.8834 0.4198 0.054 Uiso 1 1 calc R . . H14B H 0.2219 0.9784 0.3940 0.054 Uiso 1 1 calc R . . C15 C 0.0481(9) 0.9867(5) 0.4640(3) 0.0471(17) Uani 1 1 d . . . C5 C 0.7514(8) 0.9686(5) 0.2135(3) 0.0462(17) Uani 1 1 d . . . H5 H 0.8412 0.9507 0.1917 0.055 Uiso 1 1 calc R . . C7 C 0.5511(8) 1.1949(5) 0.3857(3) 0.0425(15) Uani 1 1 d . . . H7 H 0.6257 1.1731 0.3558 0.051 Uiso 1 1 calc R . . C8 C 0.5235(8) 1.2843(5) 0.3894(3) 0.0427(15) Uani 1 1 d . . . H8 H 0.5815 1.3221 0.3613 0.051 Uiso 1 1 calc R . . C1 C 0.4974(8) 1.0055(4) 0.2069(3) 0.0371(14) Uani 1 1 d . . . H1 H 0.4101 1.0140 0.1802 0.044 Uiso 1 1 calc R . . C2 C 0.4861(8) 1.0172(4) 0.2773(3) 0.0363(13) Uani 1 1 d . . . H2 H 0.3943 1.0346 0.2977 0.044 Uiso 1 1 calc R . . C11 C 0.5671(8) 0.9818(5) 0.5353(3) 0.0413(15) Uani 1 1 d . . . O3W O 0.0880(16) 1.1183(11) 0.3161(5) 0.187(6) Uani 1 1 d . . . O2W O 0.1333(11) 1.0209(13) 0.1987(6) 0.231(10) Uani 1 1 d . . . O1W O 0.157(3) 0.824(3) 0.2097(17) 0.418(19) Uani 1 1 d . . . O5 O -0.007(3) 0.7508(18) 0.6797(17) 0.359(15) Uiso 1 1 d D . . H5A H 0.0375 0.7679 0.7146 0.538 Uiso 1 1 calc R . . C16 C 0.205(4) 0.731(2) 0.5684(18) 0.32(2) Uiso 1 1 d D . . H16A H 0.1563 0.7337 0.5239 0.480 Uiso 1 1 calc R . . H16B H 0.2428 0.6715 0.5766 0.480 Uiso 1 1 calc R . . H16C H 0.2883 0.7736 0.5695 0.480 Uiso 1 1 calc R . . C17 C 0.088(5) 0.756(3) 0.625(2) 0.33(2) Uiso 1 1 d D . . H17A H 0.1423 0.8095 0.6411 0.394 Uiso 1 1 calc R . . H17B H 0.0124 0.7813 0.5934 0.394 Uiso 1 1 calc R . . H14 H 0.705(7) 1.001(4) 0.405(3) 0.017(14) Uiso 1 1 d . . . H13 H 0.311(10) 0.926(5) 0.533(5) 0.06(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0367(4) 0.0579(4) 0.0210(3) -0.0026(3) 0.0009(3) -0.0015(3) O4 0.043(3) 0.072(3) 0.025(2) 0.0040(19) 0.0006(19) 0.007(2) N2 0.028(3) 0.067(4) 0.022(2) -0.0059(19) -0.007(2) 0.008(3) N3 0.033(2) 0.062(3) 0.0203(19) -0.007(3) 0.0014(19) 0.006(2) O3 0.039(2) 0.105(4) 0.031(2) -0.002(3) -0.002(2) -0.003(3) O2 0.051(3) 0.083(4) 0.041(3) 0.025(2) -0.009(2) -0.013(3) O1 0.035(2) 0.077(3) 0.0253(19) 0.007(2) -0.0023(16) -0.006(2) N4 0.047(3) 0.055(3) 0.021(2) 0.002(2) 0.006(2) 0.004(2) N1 0.036(3) 0.055(3) 0.023(2) -0.0040(18) -0.003(2) 0.006(3) C13 0.051(4) 0.044(4) 0.033(3) -0.007(2) 0.002(3) 0.005(3) C3 0.041(3) 0.050(3) 0.024(3) -0.007(2) 0.000(3) 0.007(3) C12 0.038(3) 0.043(3) 0.027(3) -0.003(2) 0.001(3) 0.004(3) C6 0.036(3) 0.055(4) 0.022(2) -0.002(3) -0.003(3) 0.000(3) C10 0.058(4) 0.052(4) 0.027(3) 0.002(2) 0.017(3) 0.007(4) C4 0.035(3) 0.071(5) 0.026(3) -0.006(3) -0.007(3) 0.006(3) C9 0.043(4) 0.069(4) 0.034(3) 0.005(3) 0.017(3) 0.009(3) C14 0.040(3) 0.057(4) 0.039(3) -0.010(3) 0.005(3) -0.005(3) C15 0.046(4) 0.063(5) 0.033(3) -0.011(3) 0.005(3) -0.009(3) C5 0.036(3) 0.075(5) 0.029(3) -0.008(3) 0.005(3) 0.010(3) C7 0.042(4) 0.061(4) 0.024(3) -0.001(2) 0.010(3) 0.007(3) C8 0.043(4) 0.062(4) 0.022(3) 0.001(2) 0.008(3) 0.003(3) C1 0.036(3) 0.049(4) 0.025(3) -0.005(2) 0.004(2) 0.001(3) C2 0.034(3) 0.046(4) 0.029(3) -0.004(2) 0.002(2) 0.000(3) C11 0.041(4) 0.051(4) 0.032(3) 0.001(2) -0.004(3) 0.005(3) O3W 0.169(11) 0.308(17) 0.084(6) 0.049(8) 0.013(7) -0.105(12) O2W 0.061(5) 0.54(3) 0.091(7) 0.036(12) -0.021(5) 0.030(12) O1W 0.165(19) 0.69(5) 0.40(4) -0.12(4) 0.11(2) 0.04(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 Zn1 O1 1.917(4) 2_674 ? Zn1 O4 1.942(5) 2_574 ? Zn1 N4 1.998(5) 4_645 ? Zn1 N1 1.997(5) . ? O4 C15 1.287(8) . ? O4 Zn1 1.942(5) 2_575 ? N2 C3 1.358(7) . ? N2 N3 1.411(7) . ? N2 H14 0.83(6) . ? N3 C6 1.375(8) . ? N3 C12 1.446(8) . ? O3 C15 1.232(9) . ? O2 C11 1.246(8) . ? O1 C11 1.278(9) . ? O1 Zn1 1.917(4) 2_675 ? N4 C9 1.348(9) . ? N4 C8 1.372(8) . ? N4 Zn1 1.998(5) 4_655 ? N1 C5 1.330(9) . ? N1 C1 1.349(9) . ? C13 C12 1.313(10) . ? C13 C14 1.456(10) . ? C13 H13 0.99(9) . ? C3 C4 1.402(10) . ? C3 C2 1.405(10) . ? C12 C11 1.503(9) . ? C6 C10 1.379(9) . ? C6 C7 1.393(9) . ? C10 C9 1.399(10) . ? C10 H10 0.9300 . ? C4 C5 1.370(9) . ? C4 H4 0.9300 . ? C9 H9 0.9300 . ? C14 C15 1.507(10) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C5 H5 0.9300 . ? C7 C8 1.347(10) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C1 C2 1.377(8) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? O5 C17 1.3501(11) . ? O5 H5A 0.8200 . ? C16 C17 1.5401(11) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? 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 Zn1 O4 115.7(2) 2_674 2_574 ? O1 Zn1 N4 101.5(2) 2_674 4_645 ? O4 Zn1 N4 109.5(2) 2_574 4_645 ? O1 Zn1 N1 117.3(2) 2_674 . ? O4 Zn1 N1 108.2(2) 2_574 . ? N4 Zn1 N1 103.6(2) 4_645 . ? C15 O4 Zn1 116.5(5) . 2_575 ? C3 N2 N3 119.0(5) . . ? C3 N2 H14 114(4) . . ? N3 N2 H14 127(4) . . ? C6 N3 N2 117.6(5) . . ? C6 N3 C12 120.2(5) . . ? N2 N3 C12 111.3(5) . . ? C11 O1 Zn1 128.3(4) . 2_675 ? C9 N4 C8 114.4(6) . . ? C9 N4 Zn1 123.4(4) . 4_655 ? C8 N4 Zn1 122.0(4) . 4_655 ? C5 N1 C1 117.5(5) . . ? C5 N1 Zn1 121.0(4) . . ? C1 N1 Zn1 121.2(4) . . ? C12 C13 C14 127.5(7) . . ? C12 C13 H13 103(5) . . ? C14 C13 H13 126(5) . . ? N2 C3 C4 118.0(6) . . ? N2 C3 C2 123.4(6) . . ? C4 C3 C2 118.6(5) . . ? C13 C12 N3 123.2(6) . . ? C13 C12 C11 122.8(6) . . ? N3 C12 C11 113.9(6) . . ? C10 C6 N3 121.2(6) . . ? C10 C6 C7 117.0(6) . . ? N3 C6 C7 121.7(6) . . ? C6 C10 C9 119.4(6) . . ? C6 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C5 C4 C3 118.2(6) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? N4 C9 C10 124.1(6) . . ? N4 C9 H9 118.0 . . ? C10 C9 H9 118.0 . . ? C13 C14 C15 113.4(6) . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14B 108.9 . . ? C15 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? O3 C15 O4 123.8(7) . . ? O3 C15 C14 121.8(6) . . ? O4 C15 C14 114.4(7) . . ? N1 C5 C4 124.1(6) . . ? N1 C5 H5 117.9 . . ? C4 C5 H5 117.9 . . ? C8 C7 C6 120.3(6) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 N4 124.8(6) . . ? C7 C8 H8 117.6 . . ? N4 C8 H8 117.6 . . ? N1 C1 C2 123.5(6) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C1 C2 C3 118.0(6) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? O2 C11 O1 124.9(6) . . ? O2 C11 C12 121.4(6) . . ? O1 C11 C12 113.6(6) . . ? C17 O5 H5A 109.5 . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O5 C17 C16 162(5) . . ? O5 C17 H17A 95.6 . . ? C16 C17 H17A 95.6 . . ? O5 C17 H17B 95.6 . . ? C16 C17 H17B 95.6 . . ? H17A C17 H17B 103.3 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 31.97 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.043 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.163 # Attachment '5878_web_deposit_cif_file_1_PrakashKanoo_1308291693.compound2.cif' data_compound2 _database_code_depnum_ccdc_archive 'CCDC 830359' #TrackingRef '5878_web_deposit_cif_file_1_PrakashKanoo_1308291693.compound2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H34 Cd2 N8 O17' _chemical_formula_weight 1051.49 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.4628(7) _cell_length_b 9.8868(3) _cell_length_c 20.2318(6) _cell_angle_alpha 90.00 _cell_angle_beta 123.974(3) _cell_angle_gamma 90.00 _cell_volume 4223.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 22.1 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2104 _exptl_absorpt_coefficient_mu 1.087 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.75642 _exptl_absorpt_correction_T_max 0.93241 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21220 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 22.12 _reflns_number_total 2633 _reflns_number_gt 2342 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 1.4.1' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0420P)^2^+36.8881P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2633 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 C1 C 0.7299(3) 0.1411(6) 0.2089(4) 0.0343(15) Uani 1 1 d . . . H1 H 0.7142 0.0752 0.2262 0.041 Uiso 1 1 calc R . . C2 C 0.7943(3) 0.1634(6) 0.2537(4) 0.0325(15) Uani 1 1 d . . . H2 H 0.8208 0.1142 0.3001 0.039 Uiso 1 1 calc R . . C3 C 0.8195(3) 0.2613(6) 0.2286(3) 0.0264(14) Uani 1 1 d . . . C4 C 0.7764(3) 0.3330(6) 0.1595(4) 0.0343(15) Uani 1 1 d . . . H4 H 0.7906 0.3991 0.1404 0.041 Uiso 1 1 calc R . . C5 C 0.7134(3) 0.3057(7) 0.1203(4) 0.0393(16) Uani 1 1 d . . . H5 H 0.6856 0.3574 0.0756 0.047 Uiso 1 1 calc R . . C6 C 0.9127(3) 0.3689(6) 0.1822(3) 0.0269(14) Uani 1 1 d . . . C7 C 0.9281(3) 0.4821(6) 0.1546(3) 0.0309(14) Uani 1 1 d . . . H7 H 0.9354 0.5658 0.1792 0.037 Uiso 1 1 calc R . . C8 C 0.9323(3) 0.4658(6) 0.0894(3) 0.0321(15) Uani 1 1 d . . . H8 H 0.9426 0.5415 0.0716 0.038 Uiso 1 1 calc R . . C9 C 0.9105(3) 0.2415(6) 0.0807(4) 0.0340(15) Uani 1 1 d . . . H9 H 0.9054 0.1585 0.0561 0.041 Uiso 1 1 calc R . . C10 C 0.9054(3) 0.2447(6) 0.1444(3) 0.0292(14) Uani 1 1 d . . . H10 H 0.8973 0.1660 0.1624 0.035 Uiso 1 1 calc R . . C11 C 0.9326(3) 0.3680(6) 0.4049(3) 0.0225(13) Uani 1 1 d . . . C12 C 0.9247(3) 0.2515(6) 0.3521(3) 0.0238(13) Uani 1 1 d . . . C13 C 0.9533(3) 0.1347(6) 0.3814(4) 0.0281(14) Uani 1 1 d . . . C14 C 0.9469(3) 0.0081(6) 0.3377(3) 0.0321(14) Uani 1 1 d . . . H14A H 0.9850 -0.0053 0.3386 0.039 Uiso 1 1 calc R . . H14B H 0.9116 0.0174 0.2825 0.039 Uiso 1 1 calc R . . C15 C 0.9361(3) -0.1148(6) 0.3735(3) 0.0288(14) Uani 1 1 d . . . C16 C 0.7294(8) -0.254(2) 0.0941(9) 0.188(8) Uani 1 1 d . . . H16A H 0.6976 -0.2658 0.1053 0.282 Uiso 1 1 calc R . . H16B H 0.7703 -0.2736 0.1413 0.282 Uiso 1 1 calc R . . H16C H 0.7211 -0.3153 0.0524 0.282 Uiso 1 1 calc R . . C17 C 0.7277(12) -0.088(3) 0.0640(15) 0.35(3) Uani 1 1 d . . . H17A H 0.6873 -0.0723 0.0142 0.424 Uiso 1 1 calc R . . H17B H 0.7304 -0.0274 0.1035 0.424 Uiso 1 1 calc R . . N1 N 0.6887(2) 0.2083(5) 0.1421(3) 0.0319(12) Uani 1 1 d . . . N2 N 0.8847(2) 0.2775(5) 0.2683(3) 0.0269(11) Uani 1 1 d . . . N3 N 0.9059(2) 0.3868(5) 0.2444(3) 0.0297(12) Uani 1 1 d . . . N4 N 0.9227(2) 0.3512(5) 0.0510(3) 0.0277(11) Uani 1 1 d . . . O1 O 0.90184(17) 0.4731(4) 0.3692(2) 0.0270(9) Uani 1 1 d . . . O2 O 0.96753(17) 0.3544(4) 0.4796(2) 0.0293(9) Uani 1 1 d . . . O1W O 0.8959(5) -0.1053(9) 0.1320(6) 0.141(4) Uani 1 1 d . . . O3 O 0.9359(2) -0.2298(4) 0.3472(2) 0.0357(10) Uani 1 1 d . . . O2W O 0.8498(7) -0.3100(12) 0.1902(8) 0.208(5) Uani 1 1 d . . . O4 O 0.92828(18) -0.0982(4) 0.4295(2) 0.0308(10) Uani 1 1 d . . . O3W O 1.0000 -0.2233(12) 0.2500 0.272(13) Uani 1 2 d S . . O5 O 0.772(2) -0.057(5) 0.054(3) 0.68(4) Uani 1 1 d . . . H5A H 0.8068 -0.0705 0.0960 1.020 Uiso 1 1 calc R . . O4W O 0.5967(3) -0.3912(6) -0.0021(3) 0.092(2) Uani 1 1 d . . . Cd1 Cd 0.579629(18) 0.16064(4) 0.06164(2) 0.02291(18) Uani 1 1 d . . . H13 H 0.982(3) 0.130(6) 0.441(4) 0.041(17) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.026(4) 0.042(4) 0.029(4) 0.003(3) 0.013(3) -0.009(3) C2 0.033(4) 0.033(4) 0.029(3) 0.002(3) 0.015(3) -0.003(3) C3 0.028(4) 0.030(3) 0.021(3) -0.004(3) 0.014(3) -0.003(3) C4 0.030(4) 0.035(4) 0.035(4) 0.010(3) 0.016(3) 0.000(3) C5 0.030(4) 0.044(4) 0.034(4) 0.010(3) 0.012(3) 0.001(3) C6 0.018(3) 0.035(4) 0.023(3) 0.002(3) 0.009(3) -0.001(3) C7 0.031(3) 0.032(4) 0.028(3) 0.000(3) 0.016(3) -0.001(3) C8 0.033(4) 0.034(4) 0.034(3) 0.002(3) 0.022(3) -0.004(3) C9 0.033(4) 0.035(4) 0.032(4) -0.003(3) 0.017(3) -0.001(3) C10 0.034(4) 0.029(3) 0.029(3) -0.002(3) 0.020(3) -0.006(3) C11 0.020(3) 0.027(3) 0.026(4) 0.000(3) 0.016(3) -0.003(3) C12 0.023(3) 0.026(3) 0.023(3) 0.003(3) 0.013(3) 0.000(3) C13 0.027(3) 0.032(4) 0.025(4) 0.000(3) 0.015(3) -0.002(3) C14 0.035(4) 0.030(3) 0.025(3) 0.003(3) 0.012(3) 0.004(3) C15 0.022(3) 0.031(4) 0.023(3) 0.006(3) 0.006(3) 0.004(3) C16 0.186(17) 0.29(2) 0.123(12) 0.059(15) 0.106(13) 0.059(17) C17 0.23(3) 0.28(3) 0.24(2) -0.15(2) -0.06(2) 0.20(3) N1 0.023(3) 0.037(3) 0.030(3) 0.005(2) 0.012(2) -0.003(2) N2 0.026(3) 0.032(3) 0.022(3) 0.000(2) 0.013(2) -0.004(2) N3 0.032(3) 0.034(3) 0.028(3) 0.001(2) 0.020(2) -0.008(2) N4 0.025(3) 0.034(3) 0.025(3) 0.002(2) 0.015(2) -0.001(2) O1 0.027(2) 0.026(2) 0.025(2) 0.0002(19) 0.0126(18) 0.0037(19) O2 0.023(2) 0.043(3) 0.019(2) -0.0011(18) 0.0099(19) 0.0061(18) O1W 0.191(9) 0.124(7) 0.177(8) -0.074(6) 0.146(8) -0.079(6) O3 0.049(3) 0.023(2) 0.037(2) 0.001(2) 0.026(2) 0.003(2) O2W 0.262(15) 0.162(10) 0.226(13) -0.058(9) 0.152(12) -0.025(10) O4 0.034(2) 0.030(2) 0.025(2) 0.0001(18) 0.014(2) -0.0001(19) O3W 0.51(3) 0.055(7) 0.109(10) 0.000 0.087(16) 0.000 O5 0.67(8) 0.84(9) 0.64(6) -0.26(6) 0.43(6) -0.38(7) O4W 0.137(6) 0.072(4) 0.064(4) -0.006(3) 0.054(4) -0.039(4) Cd1 0.0218(3) 0.0273(3) 0.0186(3) 0.00023(18) 0.0106(2) -0.00236(18) _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 1.336(7) . ? C1 C2 1.377(9) . ? C1 H1 0.9300 . ? C2 C3 1.404(8) . ? C2 H2 0.9300 . ? C3 N2 1.393(7) . ? C3 C4 1.394(8) . ? C4 C5 1.361(9) . ? C4 H4 0.9300 . ? C5 N1 1.353(8) . ? C5 H5 0.9300 . ? C6 N3 1.373(7) . ? C6 C7 1.401(8) . ? C6 C10 1.402(8) . ? C7 C8 1.389(8) . ? C7 H7 0.9300 . ? C8 N4 1.317(7) . ? C8 H8 0.9300 . ? C9 N4 1.357(8) . ? C9 C10 1.366(8) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 O1 1.258(6) . ? C11 O2 1.261(7) . ? C11 C12 1.506(8) . ? C12 C13 1.316(8) . ? C12 N2 1.432(7) . ? C13 C14 1.489(8) . ? C13 H13 1.00(6) . ? C14 C15 1.516(8) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 O3 1.254(7) . ? C15 O4 1.267(7) . ? C15 Cd1 2.720(6) 4_645 ? C16 C17 1.75(4) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O5 1.29(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? N1 Cd1 2.351(5) . ? N2 N3 1.410(6) . ? N4 Cd1 2.250(5) 7_655 ? O1 Cd1 2.209(4) 4_655 ? O2 Cd1 2.373(4) 8_556 ? O3 Cd1 2.355(4) 4_645 ? O4 Cd1 2.408(4) 4_645 ? O5 H5A 0.8200 . ? Cd1 O1 2.209(4) 4_645 ? Cd1 N4 2.250(5) 7_655 ? Cd1 O3 2.355(4) 4_655 ? Cd1 O2 2.373(4) 8_455 ? Cd1 O4 2.408(4) 4_655 ? Cd1 C15 2.720(6) 4_655 ? 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 C2 124.1(6) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C1 C2 C3 119.2(6) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? N2 C3 C4 122.4(5) . . ? N2 C3 C2 120.6(5) . . ? C4 C3 C2 116.8(5) . . ? C5 C4 C3 119.6(6) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? N1 C5 C4 124.3(6) . . ? N1 C5 H5 117.9 . . ? C4 C5 H5 117.9 . . ? N3 C6 C7 117.9(5) . . ? N3 C6 C10 124.5(5) . . ? C7 C6 C10 117.6(5) . . ? C8 C7 C6 118.2(6) . . ? C8 C7 H7 120.9 . . ? C6 C7 H7 120.9 . . ? N4 C8 C7 124.9(6) . . ? N4 C8 H8 117.6 . . ? C7 C8 H8 117.6 . . ? N4 C9 C10 124.4(6) . . ? N4 C9 H9 117.8 . . ? C10 C9 H9 117.8 . . ? C9 C10 C6 118.8(5) . . ? C9 C10 H10 120.6 . . ? C6 C10 H10 120.6 . . ? O1 C11 O2 124.9(5) . . ? O1 C11 C12 115.6(5) . . ? O2 C11 C12 119.6(5) . . ? C13 C12 N2 122.7(5) . . ? C13 C12 C11 122.0(5) . . ? N2 C12 C11 115.3(5) . . ? C12 C13 C14 128.4(6) . . ? C12 C13 H13 116(3) . . ? C14 C13 H13 116(3) . . ? C13 C14 C15 112.3(5) . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? O3 C15 O4 122.1(5) . . ? O3 C15 C14 118.9(5) . . ? O4 C15 C14 119.0(5) . . ? O3 C15 Cd1 59.9(3) . 4_645 ? O4 C15 Cd1 62.3(3) . 4_645 ? C14 C15 Cd1 178.0(4) . 4_645 ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O5 C17 C16 115(3) . . ? O5 C17 H17A 108.5 . . ? C16 C17 H17A 108.5 . . ? O5 C17 H17B 108.5 . . ? C16 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C1 N1 C5 115.9(5) . . ? C1 N1 Cd1 123.9(4) . . ? C5 N1 Cd1 120.2(4) . . ? C3 N2 N3 116.9(4) . . ? C3 N2 C12 119.5(4) . . ? N3 N2 C12 112.9(4) . . ? C6 N3 N2 118.9(5) . . ? C8 N4 C9 116.1(5) . . ? C8 N4 Cd1 122.2(4) . 7_655 ? C9 N4 Cd1 121.6(4) . 7_655 ? C11 O1 Cd1 119.1(3) . 4_655 ? C11 O2 Cd1 127.7(3) . 8_556 ? C15 O3 Cd1 92.7(3) . 4_645 ? C15 O4 Cd1 90.0(3) . 4_645 ? C17 O5 H5A 109.5 . . ? O1 Cd1 N4 118.23(16) 4_645 7_655 ? O1 Cd1 N1 88.75(15) 4_645 . ? N4 Cd1 N1 93.65(17) 7_655 . ? O1 Cd1 O3 87.72(14) 4_645 4_655 ? N4 Cd1 O3 153.71(16) 7_655 4_655 ? N1 Cd1 O3 90.90(16) . 4_655 ? O1 Cd1 O2 97.94(13) 4_645 8_455 ? N4 Cd1 O2 87.02(15) 7_655 8_455 ? N1 Cd1 O2 172.03(16) . 8_455 ? O3 Cd1 O2 85.07(14) 4_655 8_455 ? O1 Cd1 O4 141.40(13) 4_645 4_655 ? N4 Cd1 O4 99.83(15) 7_655 4_655 ? N1 Cd1 O4 82.28(15) . 4_655 ? O3 Cd1 O4 55.17(13) 4_655 4_655 ? O2 Cd1 O4 89.77(13) 8_455 4_655 ? O1 Cd1 C15 114.62(16) 4_645 4_655 ? N4 Cd1 C15 127.14(18) 7_655 4_655 ? N1 Cd1 C15 86.43(17) . 4_655 ? O3 Cd1 C15 27.42(16) 4_655 4_655 ? O2 Cd1 C15 86.83(15) 8_455 4_655 ? O4 Cd1 C15 27.76(15) 4_655 4_655 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 22.12 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.857 _refine_diff_density_min -0.680 _refine_diff_density_rms 0.100