# 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 N3 O7 Zn' _chemical_formula_weight 415.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7536(12) _cell_length_b 11.3569(17) _cell_length_c 15.934(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.790(11) _cell_angle_gamma 90.00 _cell_volume 1680.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 4.63 _cell_measurement_theta_max 12.43 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.643 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 1.506 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4754 _exptl_absorpt_correction_T_max 0.5217 _exptl_absorpt_process_details '(XSCANS; Siemens, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3871 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2937 _reflns_number_gt 2478 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Siemens, 1995)' _computing_cell_refinement 'XSCANS (Siemens, 1995)' _computing_data_reduction 'SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0226P)^2^+1.8576P] 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 2937 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0800 _refine_ls_wR_factor_gt 0.0747 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 Zn Zn 0.82586(3) 0.06257(3) 0.08397(2) 0.03212(12) Uani 1 1 d . . . O1 O 1.2308(2) 0.2862(2) 0.00115(18) 0.0557(7) Uani 1 1 d . . . O2 O 0.6640(2) 0.1215(2) 0.12729(14) 0.0420(5) Uani 1 1 d . . . O3 O 0.8578(2) 0.2059(2) 0.21506(16) 0.0483(6) Uani 1 1 d . . . O4 O 0.4579(2) 0.55751(19) 0.39450(15) 0.0434(5) Uani 1 1 d . . . O5 O 0.2523(2) 0.4710(2) 0.32530(13) 0.0400(5) Uani 1 1 d . . . O6 O 0.7167(2) -0.0464(2) -0.01607(15) 0.0398(5) Uani 1 1 d . . . N1 N 0.8154(2) 0.2056(2) -0.00401(15) 0.0320(5) Uani 1 1 d . . . N2 N 1.0537(2) 0.4096(2) -0.07440(16) 0.0375(6) Uani 1 1 d . . . H2A H 1.0381 0.4753 -0.1025 0.045 Uiso 1 1 calc R . . N3 N 0.6079(2) 0.4206(2) 0.32193(15) 0.0324(5) Uani 1 1 d . . . C1 C 0.6882(3) 0.2354(3) -0.0620(2) 0.0376(7) Uani 1 1 d . . . H1A H 0.6055 0.1965 -0.0596 0.045 Uiso 1 1 calc R . . C2 C 0.6759(3) 0.3209(3) -0.1244(2) 0.0403(7) Uani 1 1 d . . . H2B H 0.5865 0.3399 -0.1636 0.048 Uiso 1 1 calc R . . C3 C 0.7980(3) 0.3782(3) -0.1281(2) 0.0395(7) Uani 1 1 d . . . H3B H 0.7917 0.4364 -0.1702 0.047 Uiso 1 1 calc R . . C4 C 0.9314(3) 0.3490(2) -0.06884(18) 0.0310(6) Uani 1 1 d . . . C5 C 0.9347(3) 0.2616(3) -0.00735(18) 0.0326(6) Uani 1 1 d . . . H5A H 1.0227 0.2411 0.0329 0.039 Uiso 1 1 calc R . . C6 C 1.1931(3) 0.3769(3) -0.0409(2) 0.0368(7) Uani 1 1 d . . . C7 C 1.3004(3) 0.4602(3) -0.0602(2) 0.0413(7) Uani 1 1 d . . . H7A H 1.2636 0.5400 -0.0631 0.050 Uiso 1 1 calc R . . H7B H 1.3101 0.4412 -0.1175 0.050 Uiso 1 1 calc R . . C8 C 1.4478(3) 0.4550(3) 0.0084(2) 0.0372(7) Uani 1 1 d . . . H8A H 1.4875 0.3767 0.0085 0.045 Uiso 1 1 calc R . . H8B H 1.4374 0.4690 0.0662 0.045 Uiso 1 1 calc R . . C9 C 0.7250(3) 0.1924(3) 0.18806(19) 0.0340(6) Uani 1 1 d . . . C10 C 0.6300(3) 0.2646(3) 0.22640(18) 0.0324(6) Uani 1 1 d . . . C11 C 0.4827(3) 0.2478(3) 0.20077(19) 0.0388(7) Uani 1 1 d . . . H11A H 0.4403 0.1896 0.1600 0.047 Uiso 1 1 calc R . . C12 C 0.3987(3) 0.3183(3) 0.23620(19) 0.0369(7) Uani 1 1 d . . . H12A H 0.2993 0.3085 0.2194 0.044 Uiso 1 1 calc R . . C13 C 0.4648(3) 0.4030(3) 0.29663(17) 0.0304(6) Uani 1 1 d . . . C14 C 0.6879(3) 0.3524(3) 0.28718(19) 0.0350(6) Uani 1 1 d . . . H14A H 0.7870 0.3644 0.3045 0.042 Uiso 1 1 calc R . . C15 C 0.3842(3) 0.4836(3) 0.34136(18) 0.0312(6) Uani 1 1 d . . . O7 O 1.0136(4) 0.3992(3) 0.1920(2) 0.0852(12) Uani 1 1 d . . . H7OB H 0.965(5) 0.339(4) 0.202(3) 0.080(14) Uiso 1 1 d . . . H7OA H 1.072(6) 0.417(4) 0.237(3) 0.095(18) Uiso 1 1 d . . . H6OB H 0.728(4) -0.029(3) -0.060(2) 0.050(11) Uiso 1 1 d . . . H6OA H 0.734(5) -0.124(4) -0.007(3) 0.097(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 Zn 0.02839(18) 0.03350(19) 0.03715(19) 0.00455(15) 0.01397(13) 0.00189(15) O1 0.0338(12) 0.0424(13) 0.0870(18) 0.0236(13) 0.0127(12) 0.0008(10) O2 0.0398(12) 0.0465(13) 0.0425(12) -0.0126(10) 0.0166(10) 0.0003(10) O3 0.0330(12) 0.0484(13) 0.0667(15) -0.0099(12) 0.0203(11) 0.0000(10) O4 0.0329(11) 0.0473(13) 0.0545(13) -0.0183(11) 0.0199(10) -0.0067(10) O5 0.0259(10) 0.0544(13) 0.0397(11) -0.0051(10) 0.0101(9) -0.0018(9) O6 0.0502(13) 0.0367(13) 0.0358(12) 0.0001(10) 0.0179(10) -0.0028(10) N1 0.0289(12) 0.0314(13) 0.0362(13) 0.0014(10) 0.0108(10) -0.0008(10) N2 0.0307(13) 0.0359(14) 0.0443(14) 0.0117(11) 0.0094(11) -0.0032(10) N3 0.0306(12) 0.0345(13) 0.0330(12) -0.0053(10) 0.0111(10) -0.0039(10) C1 0.0277(15) 0.0362(16) 0.0494(18) -0.0021(14) 0.0123(14) -0.0025(13) C2 0.0279(15) 0.0428(18) 0.0441(17) 0.0019(14) 0.0022(13) 0.0011(13) C3 0.0372(16) 0.0402(17) 0.0379(16) 0.0088(14) 0.0069(13) 0.0006(14) C4 0.0269(14) 0.0301(15) 0.0345(15) -0.0009(12) 0.0073(12) -0.0021(11) C5 0.0285(14) 0.0333(15) 0.0353(15) 0.0016(12) 0.0085(12) -0.0014(12) C6 0.0316(16) 0.0319(16) 0.0464(17) -0.0021(14) 0.0112(13) -0.0026(13) C7 0.0342(16) 0.0433(18) 0.0450(17) 0.0067(14) 0.0101(14) -0.0068(14) C8 0.0294(15) 0.0383(17) 0.0447(17) 0.0017(14) 0.0127(13) -0.0029(13) C9 0.0390(16) 0.0314(15) 0.0362(15) 0.0015(13) 0.0181(13) 0.0008(13) C10 0.0332(15) 0.0346(15) 0.0304(14) -0.0003(12) 0.0114(12) 0.0021(12) C11 0.0366(16) 0.0437(17) 0.0356(16) -0.0111(14) 0.0104(13) -0.0058(14) C12 0.0274(14) 0.0476(18) 0.0347(15) -0.0052(14) 0.0078(12) -0.0018(13) C13 0.0298(14) 0.0361(15) 0.0265(13) 0.0029(12) 0.0105(11) -0.0001(12) C14 0.0294(15) 0.0392(16) 0.0384(16) -0.0025(13) 0.0136(12) 0.0001(13) C15 0.0335(15) 0.0339(15) 0.0281(14) 0.0029(12) 0.0121(12) -0.0003(13) O7 0.074(2) 0.079(2) 0.072(2) 0.0355(17) -0.0244(17) -0.0409(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 Zn O2 2.021(2) . ? Zn O4 2.032(2) 2_645 ? Zn O6 2.042(2) . ? Zn N1 2.128(2) . ? Zn N3 2.162(2) 2_645 ? O1 C6 1.223(4) . ? O2 C9 1.260(4) . ? O3 C9 1.243(4) . ? O4 C15 1.252(3) . ? O4 Zn 2.032(2) 2_655 ? O5 C15 1.240(3) . ? O6 H6OB 0.77(4) . ? O6 H6OA 0.90(5) . ? N1 C5 1.342(4) . ? N1 C1 1.344(4) . ? N2 C6 1.352(4) . ? N2 C4 1.403(3) . ? N2 H2A 0.8600 . ? N3 C14 1.334(4) . ? N3 C13 1.344(4) . ? N3 Zn 2.162(2) 2_655 ? C1 C2 1.369(4) . ? C1 H1A 0.9300 . ? C2 C3 1.374(4) . ? C2 H2B 0.9300 . ? C3 C4 1.394(4) . ? C3 H3B 0.9300 . ? C4 C5 1.388(4) . ? C5 H5A 0.9300 . ? C6 C7 1.511(4) . ? C7 C8 1.519(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C8 1.524(5) 3_865 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.501(4) . ? C10 C11 1.382(4) . ? C10 C14 1.385(4) . ? C11 C12 1.383(4) . ? C11 H11A 0.9300 . ? C12 C13 1.374(4) . ? C12 H12A 0.9300 . ? C13 C15 1.519(4) . ? C14 H14A 0.9300 . ? O7 H7OB 0.87(5) . ? O7 H7OA 0.79(5) . ? 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 O2 Zn O4 146.20(9) . 2_645 ? O2 Zn O6 101.05(9) . . ? O4 Zn O6 112.43(9) 2_645 . ? O2 Zn N1 95.00(9) . . ? O4 Zn N1 88.35(8) 2_645 . ? O6 Zn N1 92.27(10) . . ? O2 Zn N3 96.27(9) . 2_645 ? O4 Zn N3 77.69(8) 2_645 2_645 ? O6 Zn N3 93.65(10) . 2_645 ? N1 Zn N3 166.02(9) . 2_645 ? C9 O2 Zn 103.81(18) . . ? C15 O4 Zn 119.03(18) . 2_655 ? Zn O6 H6OB 112(3) . . ? Zn O6 H6OA 116(3) . . ? H6OB O6 H6OA 109(4) . . ? C5 N1 C1 118.9(2) . . ? C5 N1 Zn 121.35(19) . . ? C1 N1 Zn 119.54(19) . . ? C6 N2 C4 127.8(2) . . ? C6 N2 H2A 116.1 . . ? C4 N2 H2A 116.1 . . ? C14 N3 C13 118.4(2) . . ? C14 N3 Zn 129.16(19) . 2_655 ? C13 N3 Zn 112.48(18) . 2_655 ? N1 C1 C2 122.3(3) . . ? N1 C1 H1A 118.8 . . ? C2 C1 H1A 118.8 . . ? C1 C2 C3 118.9(3) . . ? C1 C2 H2B 120.6 . . ? C3 C2 H2B 120.6 . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3B 120.0 . . ? C4 C3 H3B 120.0 . . ? C5 C4 C3 117.7(3) . . ? C5 C4 N2 123.9(2) . . ? C3 C4 N2 118.4(3) . . ? N1 C5 C4 122.2(3) . . ? N1 C5 H5A 118.9 . . ? C4 C5 H5A 118.9 . . ? O1 C6 N2 123.0(3) . . ? O1 C6 C7 121.9(3) . . ? N2 C6 C7 115.0(3) . . ? C6 C7 C8 113.0(3) . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 C8 112.6(3) . 3_865 ? C7 C8 H8A 109.1 . . ? C8 C8 H8A 109.1 3_865 . ? C7 C8 H8B 109.1 . . ? C8 C8 H8B 109.1 3_865 . ? H8A C8 H8B 107.8 . . ? O3 C9 O2 122.9(3) . . ? O3 C9 C10 120.0(3) . . ? O2 C9 C10 117.1(3) . . ? C11 C10 C14 118.1(3) . . ? C11 C10 C9 121.4(3) . . ? C14 C10 C9 120.5(3) . . ? C10 C11 C12 119.4(3) . . ? C10 C11 H11A 120.3 . . ? C12 C11 H11A 120.3 . . ? C13 C12 C11 118.8(3) . . ? C13 C12 H12A 120.6 . . ? C11 C12 H12A 120.6 . . ? N3 C13 C12 122.4(3) . . ? N3 C13 C15 114.1(2) . . ? C12 C13 C15 123.5(3) . . ? N3 C14 C10 122.8(3) . . ? N3 C14 H14A 118.6 . . ? C10 C14 H14A 118.6 . . ? O5 C15 O4 124.2(3) . . ? O5 C15 C13 119.1(3) . . ? O4 C15 C13 116.7(2) . . ? H7OB O7 H7OA 108(4) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.278 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 949402' ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 N3 O5 Zn' _chemical_formula_weight 379.65 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 16.031(3) _cell_length_b 7.3539(8) _cell_length_c 13.9631(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.457(7) _cell_angle_gamma 90.00 _cell_volume 1552.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 31 _cell_measurement_theta_min 7.92 _cell_measurement_theta_max 12.47 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.625 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 1.614 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7898 _exptl_absorpt_correction_T_max 0.9959 _exptl_absorpt_process_details '(XSCANS; Siemens, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3582 _diffrn_reflns_av_R_equivalents 0.0182 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2721 _reflns_number_gt 2311 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Siemens, 1995)' _computing_cell_refinement 'XSCANS (Siemens, 1995)' _computing_data_reduction 'SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0311P)^2^+1.0524P] 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 2721 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0685 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 Zn Zn 0.387918(16) 0.49579(3) 0.233721(18) 0.02526(10) Uani 1 1 d . . . O1 O 0.0113(12) -0.077(3) 0.1282(12) 0.078(4) Uani 0.50 1 d P . . O1' O 0.0291(12) -0.121(3) 0.1680(12) 0.085(5) Uani 0.50 1 d P . . O2 O 0.46717(11) 0.2384(2) 0.23428(12) 0.0326(4) Uani 1 1 d . . . O3 O 0.53272(10) 0.0936(2) 0.13772(12) 0.0316(4) Uani 1 1 d . . . O4 O 0.31991(11) 0.7317(2) 0.16603(12) 0.0343(4) Uani 1 1 d . . . O5 O 0.26832(13) 0.8727(3) 0.01667(14) 0.0480(5) Uani 1 1 d . . . N1 N 0.28057(12) 0.3649(3) 0.24617(14) 0.0275(4) Uani 1 1 d . . . N2 N 0.14432(14) -0.0146(3) 0.1201(2) 0.0471(6) Uani 1 1 d . . . H2A H 0.1763 -0.0379 0.0829 0.057 Uiso 1 1 calc R . . N3 N 0.39028(12) 0.4699(2) 0.09104(14) 0.0244(4) Uani 1 1 d . . . C1 C 0.24017(17) 0.4207(4) 0.3108(2) 0.0397(6) Uani 1 1 d . . . H1A H 0.2646 0.5160 0.3550 0.048 Uiso 1 1 calc R . . C2 C 0.16343(19) 0.3404(4) 0.3133(2) 0.0529(8) Uani 1 1 d . . . H2B H 0.1359 0.3840 0.3577 0.063 Uiso 1 1 calc R . . C3 C 0.12731(18) 0.1967(4) 0.2508(2) 0.0524(8) Uani 1 1 d . . . H3A H 0.0754 0.1420 0.2522 0.063 Uiso 1 1 calc R . . C4 C 0.17013(15) 0.1340(3) 0.1847(2) 0.0364(6) Uani 1 1 d . . . C5 C 0.24608(15) 0.2242(3) 0.18479(18) 0.0302(5) Uani 1 1 d . . . H5A H 0.2744 0.1853 0.1402 0.036 Uiso 1 1 calc R . . C6 C 0.0748(2) -0.1272(4) 0.1086(3) 0.0638(10) Uani 1 1 d . . . C7 C 0.0725(2) -0.2876(5) 0.0405(3) 0.0741(12) Uani 1 1 d . . . H7A H 0.0650 -0.2435 -0.0273 0.089 Uiso 1 1 calc R . . H7B H 0.1288 -0.3503 0.0652 0.089 Uiso 1 1 calc R . . C8 C 0.00014(19) -0.4201(4) 0.0347(3) 0.0547(8) Uani 1 1 d . . . H8A H -0.0564 -0.3582 0.0097 0.066 Uiso 1 1 calc R . . H8B H 0.0075 -0.4652 0.1023 0.066 Uiso 1 1 calc R . . C9 C 0.47991(14) 0.2104(3) 0.15235(17) 0.0266(5) Uani 1 1 d . . . C10 C 0.43106(14) 0.3318(3) 0.06355(16) 0.0243(5) Uani 1 1 d . . . C11 C 0.43108(15) 0.3147(3) -0.03511(17) 0.0288(5) Uani 1 1 d . . . H11A H 0.4593 0.2179 -0.0543 0.035 Uiso 1 1 calc R . . C12 C 0.38743(16) 0.4474(3) -0.10444(17) 0.0326(5) Uani 1 1 d . . . H12A H 0.3867 0.4406 -0.1712 0.039 Uiso 1 1 calc R . . C13 C 0.34511(15) 0.5894(3) -0.07485(17) 0.0322(5) Uani 1 1 d . . . H13A H 0.3150 0.6774 -0.1214 0.039 Uiso 1 1 calc R . . C14 C 0.34827(14) 0.5984(3) 0.02552(17) 0.0261(5) Uani 1 1 d . . . C15 C 0.30907(15) 0.7488(3) 0.07262(18) 0.0317(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 Zn 0.02787(15) 0.02489(16) 0.02456(15) -0.00254(10) 0.01078(11) -0.00415(11) O1 0.045(4) 0.081(9) 0.129(11) -0.054(7) 0.054(7) -0.029(5) O1' 0.082(10) 0.071(8) 0.137(12) -0.062(8) 0.083(9) -0.054(7) O2 0.0367(9) 0.0338(9) 0.0307(8) 0.0068(7) 0.0159(7) 0.0075(7) O3 0.0371(9) 0.0283(9) 0.0287(8) 0.0006(7) 0.0099(7) 0.0103(7) O4 0.0423(9) 0.0293(9) 0.0353(9) 0.0007(7) 0.0184(7) 0.0105(8) O5 0.0647(12) 0.0390(11) 0.0489(11) 0.0160(9) 0.0303(10) 0.0272(10) N1 0.0278(9) 0.0260(10) 0.0313(10) -0.0045(8) 0.0130(8) -0.0040(8) N2 0.0360(12) 0.0403(13) 0.0743(17) -0.0284(12) 0.0307(12) -0.0157(10) N3 0.0251(9) 0.0231(10) 0.0258(9) -0.0003(7) 0.0096(8) 0.0015(7) C1 0.0433(14) 0.0350(14) 0.0482(15) -0.0175(12) 0.0249(12) -0.0099(12) C2 0.0524(16) 0.0536(18) 0.070(2) -0.0293(16) 0.0434(16) -0.0162(14) C3 0.0435(16) 0.0497(18) 0.080(2) -0.0266(16) 0.0415(16) -0.0199(14) C4 0.0285(12) 0.0321(13) 0.0521(15) -0.0131(12) 0.0181(11) -0.0074(11) C5 0.0279(12) 0.0298(12) 0.0352(12) -0.0075(10) 0.0135(10) -0.0023(10) C6 0.0447(17) 0.055(2) 0.105(3) -0.0440(19) 0.0417(18) -0.0268(15) C7 0.061(2) 0.053(2) 0.124(3) -0.052(2) 0.054(2) -0.0331(17) C8 0.0435(15) 0.0395(16) 0.083(2) -0.0277(17) 0.0241(15) -0.0165(13) C9 0.0260(11) 0.0217(11) 0.0314(12) -0.0006(9) 0.0086(9) -0.0007(9) C10 0.0234(10) 0.0216(11) 0.0274(11) -0.0007(9) 0.0078(9) 0.0019(9) C11 0.0306(11) 0.0269(12) 0.0295(12) -0.0055(9) 0.0108(9) 0.0025(10) C12 0.0373(13) 0.0364(13) 0.0235(11) -0.0037(10) 0.0095(10) -0.0007(11) C13 0.0347(12) 0.0321(13) 0.0296(12) 0.0065(10) 0.0103(10) 0.0046(11) C14 0.0257(11) 0.0231(12) 0.0299(11) 0.0029(9) 0.0098(9) 0.0031(9) C15 0.0311(12) 0.0274(12) 0.0404(13) 0.0024(11) 0.0170(10) 0.0045(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 Zn O3 1.9590(15) 2_655 ? Zn N3 2.0142(18) . ? Zn N1 2.0293(18) . ? Zn O4 2.0989(16) . ? Zn O2 2.2780(16) . ? O1 O1' 0.62(3) . ? O1 C6 1.197(19) . ? O1' C6 1.277(19) . ? O2 C9 1.244(3) . ? O3 C9 1.269(3) . ? O3 Zn 1.9590(15) 2_645 ? O4 C15 1.263(3) . ? O5 C15 1.236(3) . ? N1 C1 1.338(3) . ? N1 C5 1.339(3) . ? N2 C6 1.355(3) . ? N2 C4 1.389(3) . ? N2 H2A 0.8600 . ? N3 C14 1.331(3) . ? N3 C10 1.332(3) . ? C1 C2 1.375(4) . ? C1 H1A 0.9300 . ? C2 C3 1.371(4) . ? C2 H2B 0.9300 . ? C3 C4 1.399(4) . ? C3 H3A 0.9300 . ? C4 C5 1.386(3) . ? C5 H5A 0.9300 . ? C6 C7 1.508(4) . ? C7 C8 1.496(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C8 1.523(5) 3_545 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.517(3) . ? C10 C11 1.383(3) . ? C11 C12 1.388(3) . ? C11 H11A 0.9300 . ? C12 C13 1.381(3) . ? C12 H12A 0.9300 . ? C13 C14 1.387(3) . ? C13 H13A 0.9300 . ? C14 C15 1.526(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn N3 136.11(7) 2_655 . ? O3 Zn N1 113.97(7) 2_655 . ? N3 Zn N1 109.62(7) . . ? O3 Zn O4 100.98(7) 2_655 . ? N3 Zn O4 79.09(7) . . ? N1 Zn O4 95.89(7) . . ? O3 Zn O2 96.36(7) 2_655 . ? N3 Zn O2 74.38(6) . . ? N1 Zn O2 95.37(7) . . ? O4 Zn O2 153.34(6) . . ? O1' O1 C6 83(4) . . ? O1 O1' C6 68(3) . . ? C9 O2 Zn 113.38(14) . . ? C9 O3 Zn 111.43(14) . 2_645 ? C15 O4 Zn 114.80(14) . . ? C1 N1 C5 118.6(2) . . ? C1 N1 Zn 121.80(16) . . ? C5 N1 Zn 119.51(15) . . ? C6 N2 C4 127.8(2) . . ? C6 N2 H2A 116.1 . . ? C4 N2 H2A 116.1 . . ? C14 N3 C10 121.84(19) . . ? C14 N3 Zn 116.16(15) . . ? C10 N3 Zn 122.00(15) . . ? N1 C1 C2 121.6(2) . . ? N1 C1 H1A 119.2 . . ? C2 C1 H1A 119.2 . . ? C3 C2 C1 120.4(2) . . ? C3 C2 H2B 119.8 . . ? C1 C2 H2B 119.8 . . ? C2 C3 C4 118.6(2) . . ? C2 C3 H3A 120.7 . . ? C4 C3 H3A 120.7 . . ? C5 C4 N2 116.7(2) . . ? C5 C4 C3 117.7(2) . . ? N2 C4 C3 125.6(2) . . ? N1 C5 C4 123.1(2) . . ? N1 C5 H5A 118.5 . . ? C4 C5 H5A 118.5 . . ? O1 C6 O1' 28.9(13) . . ? O1 C6 N2 120.8(10) . . ? O1' C6 N2 121.9(9) . . ? O1 C6 C7 122.8(10) . . ? O1' C6 C7 122.7(9) . . ? N2 C6 C7 113.5(3) . . ? C8 C7 C6 113.5(3) . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? C6 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C8 112.0(3) . 3_545 ? C7 C8 H8A 109.2 . . ? C8 C8 H8A 109.2 3_545 . ? C7 C8 H8B 109.2 . . ? C8 C8 H8B 109.2 3_545 . ? H8A C8 H8B 107.9 . . ? O2 C9 O3 125.7(2) . . ? O2 C9 C10 117.10(19) . . ? O3 C9 C10 117.19(19) . . ? N3 C10 C11 121.3(2) . . ? N3 C10 C9 112.50(18) . . ? C11 C10 C9 126.1(2) . . ? C10 C11 C12 117.6(2) . . ? C10 C11 H11A 121.2 . . ? C12 C11 H11A 121.2 . . ? C13 C12 C11 120.4(2) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C12 C13 C14 118.8(2) . . ? C12 C13 H13A 120.6 . . ? C14 C13 H13A 120.6 . . ? N3 C14 C13 120.0(2) . . ? N3 C14 C15 113.90(19) . . ? C13 C14 C15 126.0(2) . . ? O5 C15 O4 126.0(2) . . ? O5 C15 C14 118.0(2) . . ? O4 C15 C14 116.0(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.237 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 949403' ####################################################################### # # 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_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H22 N3 O10 Zn' _chemical_formula_weight 469.73 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.0604(13) _cell_length_b 9.1735(10) _cell_length_c 17.818(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.645(12) _cell_angle_gamma 90.00 _cell_volume 1937.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 27 _cell_measurement_theta_min 5.16 _cell_measurement_theta_max 12.50 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.610 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 972 _exptl_absorpt_coefficient_mu 1.328 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7767 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details '(XSCANS; Siemens, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4429 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3393 _reflns_number_gt 2893 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0402P)^2^+2.4522P] 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 3393 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0885 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 Zn Zn 1.01541(3) 0.12781(3) 1.199606(17) 0.02128(12) Uani 1 1 d . . . O1 O 0.9981(2) -0.2305(3) 1.41464(15) 0.0490(7) Uani 1 1 d . . . O2 O 1.02445(16) 0.90289(19) 1.19872(11) 0.0244(4) Uani 1 1 d . . . O3 O 1.20199(17) 0.8483(2) 1.18799(13) 0.0301(5) Uani 1 1 d . . . O4 O 1.0645(2) 0.7467(2) 1.03103(12) 0.0372(5) Uani 1 1 d . . . O5 O 1.1704(2) 0.5521(2) 1.02328(12) 0.0382(5) Uani 1 1 d . . . O6 O 0.89620(19) 0.1268(3) 1.09955(12) 0.0303(5) Uani 1 1 d . . . O7 O 1.1354(2) 0.1376(3) 1.30413(14) 0.0333(5) Uani 1 1 d . . . O8 O 1.1626(2) 0.1223(3) 1.13704(13) 0.0329(5) Uani 1 1 d . . . N1 N 0.8885(2) 0.1112(3) 1.26992(14) 0.0265(5) Uani 1 1 d . . . N2 N 0.8382(2) -0.1175(3) 1.43191(15) 0.0336(6) Uani 1 1 d . . . H2A H 0.7858 -0.1194 1.4587 0.040 Uiso 1 1 calc R . . N3 N 1.02720(19) 0.3593(2) 1.19505(12) 0.0222(5) Uani 1 1 d . . . C1 C 0.8053(3) 0.2063(4) 1.26720(19) 0.0346(7) Uani 1 1 d . . . H1A H 0.7951 0.2767 1.2290 0.042 Uiso 1 1 calc R . . C2 C 0.7332(3) 0.2048(4) 1.3188(2) 0.0423(8) Uani 1 1 d . . . H2B H 0.6774 0.2754 1.3168 0.051 Uiso 1 1 calc R . . C3 C 0.7452(3) 0.0968(4) 1.37375(19) 0.0389(8) Uani 1 1 d . . . H3A H 0.6963 0.0929 1.4084 0.047 Uiso 1 1 calc R . . C4 C 0.8304(2) -0.0058(3) 1.37698(17) 0.0274(6) Uani 1 1 d . . . C5 C 0.9009(3) 0.0062(3) 1.32373(17) 0.0296(7) Uani 1 1 d . . . H5A H 0.9591 -0.0609 1.3253 0.036 Uiso 1 1 calc R . . C6 C 0.9182(3) -0.2224(3) 1.44777(17) 0.0329(7) Uani 1 1 d . . . C7 C 0.9030(4) -0.3307(4) 1.5093(2) 0.0500(10) Uani 1 1 d . . . H7B H 0.8326 -0.3825 1.4929 0.060 Uiso 1 1 calc R . . H7C H 0.8968 -0.2773 1.5554 0.060 Uiso 1 1 calc R . . C8 C 0.9985(4) -0.4424(5) 1.5287(2) 0.0629(12) Uani 1 1 d . . . H8B H 1.0699 -0.3907 1.5364 0.075 Uiso 1 1 calc R . . H8C H 0.9924 -0.4887 1.5767 0.075 Uiso 1 1 calc R . . C9 C 1.0247(3) 0.4439(3) 1.25603(15) 0.0251(6) Uani 1 1 d . . . H9A H 1.0081 0.4012 1.3000 0.030 Uiso 1 1 calc R . . C10 C 1.0459(2) 0.5918(3) 1.25644(15) 0.0246(6) Uani 1 1 d . . . H10A H 1.0417 0.6475 1.2995 0.030 Uiso 1 1 calc R . . C11 C 1.0736(2) 0.6568(3) 1.19160(15) 0.0181(5) Uani 1 1 d . . . C12 C 1.0774(2) 0.5692(3) 1.12821(14) 0.0182(5) Uani 1 1 d . . . C13 C 1.0520(2) 0.4222(3) 1.13274(15) 0.0205(6) Uani 1 1 d . . . H13A H 1.0522 0.3644 1.0899 0.025 Uiso 1 1 calc R . . C14 C 1.1030(2) 0.8166(3) 1.19238(14) 0.0188(5) Uani 1 1 d . . . C15 C 1.1069(2) 0.6284(3) 1.05505(15) 0.0233(6) Uani 1 1 d . . . O9 O 0.8552(3) -0.1341(3) 1.03034(18) 0.0503(7) Uani 1 1 d . . . O10 O 1.3016(2) 0.3640(3) 1.11987(15) 0.0423(6) Uani 1 1 d . . . H6B H 0.889(3) 0.041(5) 1.079(2) 0.053(12) Uiso 1 1 d . . . H6C H 0.907(3) 0.169(5) 1.065(2) 0.049(12) Uiso 1 1 d . . . H7D H 1.153(3) 0.070(5) 1.315(2) 0.034(12) Uiso 1 1 d . . . H7E H 1.185(3) 0.191(4) 1.308(2) 0.032(10) Uiso 1 1 d . . . H8D H 1.194(4) 0.050(5) 1.155(2) 0.058(13) Uiso 1 1 d . . . H8E H 1.211(3) 0.183(5) 1.141(2) 0.043(12) Uiso 1 1 d . . . H9D H 0.930(5) -0.163(6) 1.034(3) 0.089(18) Uiso 1 1 d . . . H9E H 0.844(4) -0.122(5) 0.986(3) 0.067(16) Uiso 1 1 d . . . H10B H 1.262(4) 0.397(5) 1.085(3) 0.058(14) Uiso 1 1 d . . . H10C H 1.344(4) 0.319(6) 1.092(3) 0.076(15) 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 Zn 0.02878(19) 0.01231(17) 0.02476(18) 0.00179(12) 0.01024(13) -0.00017(13) O1 0.0499(15) 0.0461(15) 0.0605(16) 0.0241(12) 0.0349(13) 0.0164(12) O2 0.0299(11) 0.0107(9) 0.0354(11) -0.0005(8) 0.0136(8) 0.0001(8) O3 0.0262(11) 0.0149(10) 0.0510(13) 0.0022(9) 0.0117(9) 0.0000(8) O4 0.0617(15) 0.0233(11) 0.0298(11) 0.0109(9) 0.0165(10) 0.0083(11) O5 0.0583(15) 0.0299(12) 0.0347(12) 0.0033(10) 0.0304(11) 0.0077(11) O6 0.0403(12) 0.0267(12) 0.0234(10) 0.0038(10) 0.0045(9) -0.0043(10) O7 0.0345(13) 0.0221(13) 0.0407(13) 0.0078(11) -0.0004(10) -0.0069(12) O8 0.0367(12) 0.0181(11) 0.0455(13) 0.0047(10) 0.0119(10) 0.0004(11) N1 0.0304(13) 0.0231(12) 0.0291(12) 0.0041(10) 0.0138(10) 0.0024(10) N2 0.0412(15) 0.0309(14) 0.0354(14) 0.0105(11) 0.0249(12) 0.0063(12) N3 0.0320(13) 0.0128(11) 0.0237(11) 0.0002(9) 0.0099(10) -0.0027(10) C1 0.0354(17) 0.0304(17) 0.0404(17) 0.0122(14) 0.0133(14) 0.0081(14) C2 0.0369(18) 0.0371(19) 0.058(2) 0.0150(16) 0.0215(16) 0.0151(15) C3 0.0388(18) 0.0406(19) 0.0440(18) 0.0071(15) 0.0255(15) 0.0076(15) C4 0.0291(15) 0.0265(15) 0.0290(15) 0.0025(12) 0.0119(12) -0.0021(12) C5 0.0333(16) 0.0267(16) 0.0325(16) 0.0077(12) 0.0157(13) 0.0074(13) C6 0.0397(18) 0.0307(16) 0.0327(16) 0.0030(13) 0.0186(14) 0.0028(14) C7 0.074(3) 0.040(2) 0.045(2) 0.0200(17) 0.0367(19) 0.0196(19) C8 0.099(3) 0.050(2) 0.046(2) 0.0169(19) 0.029(2) 0.019(2) C9 0.0409(16) 0.0159(13) 0.0219(13) 0.0036(11) 0.0150(12) -0.0014(13) C10 0.0390(16) 0.0158(14) 0.0220(13) -0.0028(11) 0.0135(12) -0.0002(12) C11 0.0213(13) 0.0103(12) 0.0235(13) 0.0003(10) 0.0068(10) 0.0025(10) C12 0.0229(13) 0.0130(12) 0.0200(13) 0.0021(10) 0.0076(10) 0.0016(11) C13 0.0284(14) 0.0134(12) 0.0201(13) 0.0000(10) 0.0057(11) 0.0015(11) C14 0.0263(15) 0.0106(12) 0.0199(12) 0.0002(10) 0.0054(11) -0.0008(11) C15 0.0335(15) 0.0169(13) 0.0211(13) -0.0001(11) 0.0094(11) -0.0059(12) O9 0.0623(19) 0.0437(15) 0.0442(16) -0.0058(13) 0.0083(13) -0.0008(14) O10 0.0432(14) 0.0412(14) 0.0441(14) 0.0019(12) 0.0125(13) 0.0044(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn O2 2.0664(19) 1_545 ? Zn O6 2.073(2) . ? Zn N3 2.131(2) . ? Zn O7 2.139(2) . ? Zn N1 2.155(2) . ? Zn O8 2.265(2) . ? O1 C6 1.221(4) . ? O2 C14 1.255(3) . ? O2 Zn 2.0664(18) 1_565 ? O3 C14 1.245(3) . ? O4 C15 1.242(3) . ? O5 C15 1.247(3) . ? O6 H6B 0.87(5) . ? O6 H6C 0.76(4) . ? O7 H7D 0.67(4) . ? O7 H7E 0.76(4) . ? O8 H8D 0.80(5) . ? O8 H8E 0.80(4) . ? N1 C1 1.324(4) . ? N1 C5 1.348(4) . ? N2 C6 1.355(4) . ? N2 C4 1.408(4) . ? N2 H2A 0.8600 . ? N3 C13 1.333(3) . ? N3 C9 1.340(4) . ? C1 C2 1.378(4) . ? C1 H1A 0.9300 . ? C2 C3 1.381(5) . ? C2 H2B 0.9300 . ? C3 C4 1.387(4) . ? C3 H3A 0.9300 . ? C4 C5 1.391(4) . ? C5 H5A 0.9300 . ? C6 C7 1.516(4) . ? C7 C8 1.533(6) . ? C7 H7B 0.9700 . ? C7 H7C 0.9700 . ? C8 C8 1.475(8) 3_748 ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 C10 1.380(4) . ? C9 H9A 0.9300 . ? C10 C11 1.394(4) . ? C10 H10A 0.9300 . ? C11 C12 1.394(4) . ? C11 C14 1.508(3) . ? C12 C13 1.389(4) . ? C12 C15 1.514(3) . ? C13 H13A 0.9300 . ? O9 H9D 0.93(6) . ? O9 H9E 0.78(5) . ? O10 H10B 0.78(5) . ? O10 H10C 0.88(5) . ? 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 O2 Zn O6 91.04(9) 1_545 . ? O2 Zn N3 172.23(8) 1_545 . ? O6 Zn N3 90.70(9) . . ? O2 Zn O7 91.18(9) 1_545 . ? O6 Zn O7 177.51(10) . . ? N3 Zn O7 87.25(10) . . ? O2 Zn N1 88.74(8) 1_545 . ? O6 Zn N1 92.61(9) . . ? N3 Zn N1 98.75(9) . . ? O7 Zn N1 86.31(10) . . ? O2 Zn O8 85.79(8) 1_545 . ? O6 Zn O8 93.37(9) . . ? N3 Zn O8 86.55(9) . . ? O7 Zn O8 87.92(9) . . ? N1 Zn O8 171.96(9) . . ? C14 O2 Zn 132.21(17) . 1_565 ? Zn O6 H6B 111(3) . . ? Zn O6 H6C 120(3) . . ? H6B O6 H6C 98(4) . . ? Zn O7 H7D 109(3) . . ? Zn O7 H7E 120(3) . . ? H7D O7 H7E 112(4) . . ? Zn O8 H8D 100(3) . . ? Zn O8 H8E 124(3) . . ? H8D O8 H8E 105(4) . . ? C1 N1 C5 118.7(3) . . ? C1 N1 Zn 123.2(2) . . ? C5 N1 Zn 117.84(19) . . ? C6 N2 C4 128.0(2) . . ? C6 N2 H2A 116.0 . . ? C4 N2 H2A 116.0 . . ? C13 N3 C9 117.8(2) . . ? C13 N3 Zn 119.35(18) . . ? C9 N3 Zn 122.34(18) . . ? N1 C1 C2 122.5(3) . . ? N1 C1 H1A 118.8 . . ? C2 C1 H1A 118.8 . . ? C1 C2 C3 119.0(3) . . ? C1 C2 H2B 120.5 . . ? C3 C2 H2B 120.5 . . ? C2 C3 C4 119.7(3) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? C3 C4 C5 117.4(3) . . ? C3 C4 N2 118.5(3) . . ? C5 C4 N2 124.1(3) . . ? N1 C5 C4 122.8(3) . . ? N1 C5 H5A 118.6 . . ? C4 C5 H5A 118.6 . . ? O1 C6 N2 122.5(3) . . ? O1 C6 C7 121.4(3) . . ? N2 C6 C7 116.1(3) . . ? C6 C7 C8 114.5(3) . . ? C6 C7 H7B 108.6 . . ? C8 C7 H7B 108.6 . . ? C6 C7 H7C 108.6 . . ? C8 C7 H7C 108.6 . . ? H7B C7 H7C 107.6 . . ? C8 C8 C7 115.8(5) 3_748 . ? C8 C8 H8B 108.3 3_748 . ? C7 C8 H8B 108.3 . . ? C8 C8 H8C 108.3 3_748 . ? C7 C8 H8C 108.3 . . ? H8B C8 H8C 107.4 . . ? N3 C9 C10 122.8(2) . . ? N3 C9 H9A 118.6 . . ? C10 C9 H9A 118.6 . . ? C9 C10 C11 119.2(2) . . ? C9 C10 H10A 120.4 . . ? C11 C10 H10A 120.4 . . ? C12 C11 C10 118.3(2) . . ? C12 C11 C14 121.7(2) . . ? C10 C11 C14 120.0(2) . . ? C13 C12 C11 118.1(2) . . ? C13 C12 C15 119.2(2) . . ? C11 C12 C15 122.7(2) . . ? N3 C13 C12 123.7(2) . . ? N3 C13 H13A 118.1 . . ? C12 C13 H13A 118.1 . . ? O3 C14 O2 127.3(2) . . ? O3 C14 C11 116.9(2) . . ? O2 C14 C11 115.7(2) . . ? O4 C15 O5 125.6(3) . . ? O4 C15 C12 117.5(2) . . ? O5 C15 C12 116.8(2) . . ? H9D O9 H9E 96(5) . . ? H10B O10 H10C 93(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.845 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.069 _database_code_depnum_ccdc_archive 'CCDC 949404' ####################################################################### # # 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_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 Cd N5 O11' _chemical_formula_weight 665.93 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 10.5240(4) _cell_length_b 11.2622(5) _cell_length_c 12.3561(5) _cell_angle_alpha 72.554(2) _cell_angle_beta 74.971(2) _cell_angle_gamma 83.246(2) _cell_volume 1348.07(10) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9994 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 28.30 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.641 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.878 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6105 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23956 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.33 _reflns_number_total 6656 _reflns_number_gt 6074 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2010)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0365P)^2^+0.4850P] 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 6656 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0277 _refine_ls_R_factor_gt 0.0238 _refine_ls_wR_factor_ref 0.0652 _refine_ls_wR_factor_gt 0.0624 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 Cd Cd 1.492000(10) 0.095630(10) 0.336760(9) 0.03011(3) Uani 1 1 d . . . N1 N 1.28033(14) 0.16905(13) 0.42100(12) 0.0370(3) Uani 1 1 d . A . N2 N 1.15413(14) 0.37880(14) 0.60113(13) 0.0408(3) Uani 1 1 d . . . H2A H 1.2313 0.3940 0.6038 0.049 Uiso 1 1 calc R . . N3 N 0.85056(14) 0.83350(14) 1.06645(13) 0.0399(3) Uani 1 1 d . . . H3B H 0.7773 0.8315 1.0486 0.048 Uiso 1 1 calc R . . N4 N 0.70517(13) 1.01652(13) 1.26827(11) 0.0333(3) Uani 1 1 d . . . N5 N 1.39330(12) -0.04377(12) 0.27814(11) 0.0313(3) Uani 1 1 d . A . O1 O 0.93611(13) 0.42621(14) 0.66308(13) 0.0554(4) Uani 1 1 d . . . O2 O 1.06501(13) 0.76618(14) 1.02882(13) 0.0547(3) Uani 1 1 d . . . O3 O 1.4854(5) 0.1738(5) 0.1321(4) 0.0444(11) Uani 0.50 1 d P A 1 O3' O 1.4625(6) 0.1783(6) 0.1372(5) 0.0550(14) Uani 0.50 1 d P A 2 O4 O 1.39075(13) 0.15160(14) -0.00468(11) 0.0485(3) Uani 1 1 d . A . O5 O 1.44122(11) -0.10244(10) 0.49110(9) 0.0347(2) Uani 1 1 d . . . O6 O 1.33732(17) -0.28000(15) 0.54493(13) 0.0663(4) Uani 1 1 d . A . O7 O 1.55693(17) 0.29806(13) 0.27598(12) 0.0589(4) Uani 1 1 d . A . H7E H 1.6102 0.3117 0.2092 0.071 Uiso 1 1 d R . . H7C H 1.5942 0.3097 0.3251 0.071 Uiso 1 1 d R . . O8 O 1.3993(4) 0.4356(5) 0.6059(5) 0.0692(12) Uani 0.50 1 d P B 1 O8' O 1.4243(5) 0.4122(8) 0.6256(7) 0.096(2) Uani 0.50 1 d P C 2 O9 O 1.3129(5) 0.6506(6) 0.9640(5) 0.0835(16) Uani 0.50 1 d P D 1 O9' O 1.3357(7) 0.6264(7) 0.9973(6) 0.106(2) Uani 0.50 1 d P E 2 O10 O 1.4003(3) 0.3981(2) 0.8477(2) 0.1258(10) Uani 1 1 d . . . H10C H 1.4871 0.3630 0.8602 0.151 Uiso 1 1 d R . . H10D H 1.3409 0.3321 0.8939 0.151 Uiso 1 1 d R . . O11 O 1.3347(3) -0.5213(3) 0.2306(4) 0.1082(12) Uani 0.70 1 d P F 1 O11' O 1.3937(11) -0.5475(10) 0.1274(12) 0.154(4) Uani 0.30 1 d P G 2 C1 C 1.16916(18) 0.13583(17) 0.40591(16) 0.0428(4) Uani 1 1 d . . . H1A H 1.1750 0.0797 0.3626 0.051 Uiso 1 1 calc R A . C2 C 1.04738(18) 0.18164(19) 0.45202(18) 0.0480(4) Uani 1 1 d . A . H2B H 0.9725 0.1567 0.4396 0.058 Uiso 1 1 calc R . . C3 C 1.03541(17) 0.26501(18) 0.51714(16) 0.0433(4) Uani 1 1 d . . . H3A H 0.9533 0.2975 0.5480 0.052 Uiso 1 1 calc R A . C4 C 1.14946(16) 0.29881(15) 0.53511(14) 0.0353(3) Uani 1 1 d . A . C5 C 1.26936(16) 0.24826(16) 0.48464(14) 0.0364(3) Uani 1 1 d . . . H5A H 1.3460 0.2710 0.4960 0.044 Uiso 1 1 calc R A . C6 C 1.05051(17) 0.43559(16) 0.66180(14) 0.0382(4) Uani 1 1 d . . . C7 C 1.09371(17) 0.51348(17) 0.72562(16) 0.0414(4) Uani 1 1 d . . . H7A H 1.1432 0.5820 0.6686 0.050 Uiso 1 1 calc R . . H7B H 1.1523 0.4626 0.7721 0.050 Uiso 1 1 calc R . . C8 C 0.98089(18) 0.56599(17) 0.80481(15) 0.0405(4) Uani 1 1 d . . . H8A H 0.9309 0.4980 0.8622 0.049 Uiso 1 1 calc R . . H8B H 0.9225 0.6180 0.7588 0.049 Uiso 1 1 calc R . . C9 C 1.02947(18) 0.64244(17) 0.86723(16) 0.0423(4) Uani 1 1 d . . . H9A H 1.0829 0.5892 0.9175 0.051 Uiso 1 1 calc R . . H9B H 1.0843 0.7071 0.8101 0.051 Uiso 1 1 calc R . . C10 C 0.91599(18) 0.70179(18) 0.93981(16) 0.0455(4) Uani 1 1 d . . . H10A H 0.8679 0.7603 0.8877 0.055 Uiso 1 1 calc R . . H10B H 0.8565 0.6373 0.9903 0.055 Uiso 1 1 calc R . . C11 C 0.95435(17) 0.76953(16) 1.01462(15) 0.0384(4) Uani 1 1 d . . . C12 C 0.84675(15) 0.90191(15) 1.14468(13) 0.0315(3) Uani 1 1 d . . . C13 C 0.95560(16) 0.92848(17) 1.17547(15) 0.0401(4) Uani 1 1 d . . . H13A H 1.0397 0.8994 1.1450 0.048 Uiso 1 1 calc R . . C14 C 0.93533(17) 0.99944(18) 1.25271(16) 0.0439(4) Uani 1 1 d . . . H14A H 1.0066 1.0183 1.2752 0.053 Uiso 1 1 calc R . . C15 C 0.81091(17) 1.04234(16) 1.29651(14) 0.0384(4) Uani 1 1 d . . . H15A H 0.7998 1.0910 1.3475 0.046 Uiso 1 1 calc R . . C16 C 0.72391(15) 0.94756(16) 1.19422(14) 0.0335(3) Uani 1 1 d . . . H16A H 0.6506 0.9289 1.1746 0.040 Uiso 1 1 calc R . . C17 C 1.38165(16) -0.18241(16) 0.47246(14) 0.0363(3) Uani 1 1 d . . . C18 C 1.35894(15) -0.15507(15) 0.35100(14) 0.0330(3) Uani 1 1 d . A . C19 C 1.30400(16) -0.24118(17) 0.31807(16) 0.0408(4) Uani 1 1 d . . . H19A H 1.2825 -0.3192 0.3696 0.049 Uiso 1 1 calc R A . C20 C 1.28197(17) -0.20843(18) 0.20717(17) 0.0455(4) Uani 1 1 d . A . H20A H 1.2448 -0.2641 0.1831 0.055 Uiso 1 1 calc R . . C21 C 1.31562(16) -0.09263(18) 0.13276(15) 0.0419(4) Uani 1 1 d . . . H21A H 1.3006 -0.0689 0.0581 0.050 Uiso 1 1 calc R A . C22 C 1.37229(14) -0.01154(16) 0.17019(14) 0.0338(3) Uani 1 1 d . A . C23 C 1.41580(16) 0.11655(17) 0.09346(14) 0.0376(4) 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 Cd 0.03097(6) 0.03416(6) 0.02880(5) -0.01680(4) -0.00458(4) 0.00003(4) N1 0.0361(7) 0.0421(7) 0.0393(7) -0.0229(6) -0.0097(5) 0.0053(6) N2 0.0344(7) 0.0487(8) 0.0479(8) -0.0317(7) -0.0056(6) 0.0030(6) N3 0.0327(6) 0.0543(8) 0.0450(7) -0.0334(6) -0.0117(6) 0.0083(6) N4 0.0329(6) 0.0402(7) 0.0304(6) -0.0180(5) -0.0056(5) 0.0016(5) N5 0.0282(6) 0.0400(7) 0.0307(6) -0.0196(5) -0.0049(5) -0.0002(5) O1 0.0384(7) 0.0686(8) 0.0700(9) -0.0456(7) -0.0017(6) -0.0003(6) O2 0.0391(6) 0.0721(9) 0.0675(8) -0.0456(7) -0.0153(6) 0.0155(6) O3 0.0460(16) 0.053(2) 0.0387(18) -0.0108(16) -0.0133(14) -0.0172(15) O3' 0.086(3) 0.049(2) 0.040(2) -0.0094(19) -0.031(2) -0.011(2) O4 0.0449(7) 0.0685(9) 0.0354(6) -0.0138(6) -0.0163(5) -0.0024(6) O5 0.0426(6) 0.0364(6) 0.0303(5) -0.0145(4) -0.0089(4) -0.0068(5) O6 0.0993(11) 0.0600(9) 0.0457(7) -0.0057(7) -0.0211(8) -0.0422(8) O7 0.0928(11) 0.0445(7) 0.0427(7) -0.0109(6) -0.0155(7) -0.0207(7) O8 0.0329(17) 0.110(3) 0.091(2) -0.062(2) -0.0251(17) 0.0078(18) O8' 0.042(2) 0.136(5) 0.136(5) -0.066(4) -0.044(2) 0.019(2) O9 0.057(2) 0.118(4) 0.074(3) -0.042(3) 0.000(2) 0.008(2) O9' 0.126(5) 0.111(4) 0.070(3) -0.006(3) -0.013(3) -0.035(4) O10 0.146(2) 0.0957(17) 0.130(2) 0.0228(15) -0.0703(17) -0.0412(15) O11 0.0746(19) 0.077(2) 0.155(3) -0.018(2) -0.019(2) 0.0074(15) O11' 0.147(8) 0.117(7) 0.220(12) -0.041(8) -0.108(8) 0.046(6) C1 0.0441(9) 0.0488(9) 0.0466(9) -0.0295(8) -0.0134(7) 0.0041(7) C2 0.0377(8) 0.0607(11) 0.0589(10) -0.0348(9) -0.0149(8) 0.0014(8) C3 0.0344(8) 0.0524(10) 0.0492(9) -0.0285(8) -0.0069(7) 0.0054(7) C4 0.0393(8) 0.0366(8) 0.0330(7) -0.0179(6) -0.0059(6) 0.0026(6) C5 0.0331(7) 0.0414(8) 0.0402(8) -0.0220(7) -0.0078(6) 0.0025(6) C6 0.0428(8) 0.0362(8) 0.0356(8) -0.0183(7) -0.0008(7) 0.0002(7) C7 0.0416(8) 0.0449(9) 0.0421(8) -0.0267(7) -0.0014(7) 0.0002(7) C8 0.0437(9) 0.0417(8) 0.0381(8) -0.0227(7) -0.0012(7) 0.0017(7) C9 0.0435(9) 0.0434(9) 0.0435(9) -0.0266(7) -0.0012(7) 0.0026(7) C10 0.0429(9) 0.0545(10) 0.0488(9) -0.0353(8) -0.0078(7) 0.0080(8) C11 0.0398(8) 0.0417(9) 0.0372(8) -0.0212(7) -0.0070(7) 0.0069(7) C12 0.0321(7) 0.0358(7) 0.0297(7) -0.0159(6) -0.0073(6) 0.0034(6) C13 0.0297(7) 0.0511(9) 0.0464(9) -0.0254(8) -0.0094(6) 0.0039(7) C14 0.0344(8) 0.0580(10) 0.0519(10) -0.0303(8) -0.0142(7) -0.0022(7) C15 0.0402(8) 0.0458(9) 0.0372(8) -0.0244(7) -0.0079(6) -0.0028(7) C16 0.0297(7) 0.0432(8) 0.0341(7) -0.0208(7) -0.0089(6) 0.0024(6) C17 0.0386(8) 0.0402(8) 0.0342(7) -0.0171(7) -0.0057(6) -0.0066(7) C18 0.0282(7) 0.0417(8) 0.0352(7) -0.0217(6) -0.0057(6) -0.0002(6) C19 0.0373(8) 0.0462(9) 0.0461(9) -0.0239(8) -0.0078(7) -0.0056(7) C20 0.0410(8) 0.0573(10) 0.0527(9) -0.0327(8) -0.0149(7) -0.0047(8) C21 0.0353(8) 0.0619(11) 0.0388(8) -0.0274(8) -0.0124(6) 0.0012(7) C22 0.0250(6) 0.0485(9) 0.0343(7) -0.0237(7) -0.0066(5) 0.0038(6) C23 0.0334(7) 0.0500(9) 0.0328(7) -0.0176(7) -0.0089(6) 0.0035(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 Cd O7 2.3026(14) . ? Cd N5 2.3503(13) . ? Cd N4 2.3538(13) 1_644 ? Cd N1 2.3685(13) . ? Cd O5 2.4310(11) 2_856 ? Cd O3 2.433(5) . ? Cd O3' 2.448(6) . ? Cd O5 2.4697(11) . ? N1 C5 1.333(2) . ? N1 C1 1.342(2) . ? N2 C6 1.364(2) . ? N2 C4 1.397(2) . ? N2 H2A 0.8600 . ? N3 C11 1.361(2) . ? N3 C12 1.396(2) . ? N3 H3B 0.8600 . ? N4 C16 1.333(2) . ? N4 C15 1.335(2) . ? N4 Cd 2.3538(13) 1_466 ? N5 C18 1.332(2) . ? N5 C22 1.343(2) . ? O1 C6 1.217(2) . ? O2 C11 1.217(2) . ? O3 C23 1.287(7) . ? O3' C23 1.209(7) . ? O4 C23 1.245(2) . ? O5 C17 1.261(2) . ? O5 Cd 2.4310(11) 2_856 ? O6 C17 1.241(2) . ? O7 H7E 0.8499 . ? O7 H7C 0.8506 . ? O10 H10C 0.9830 . ? O10 H10D 0.9687 . ? C1 C2 1.369(3) . ? C1 H1A 0.9300 . ? C2 C3 1.385(3) . ? C2 H2B 0.9300 . ? C3 C4 1.390(2) . ? C3 H3A 0.9300 . ? C4 C5 1.393(2) . ? C5 H5A 0.9300 . ? C6 C7 1.514(2) . ? C7 C8 1.515(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.518(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.514(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.513(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C13 1.386(2) . ? C12 C16 1.390(2) . ? C13 C14 1.381(2) . ? C13 H13A 0.9300 . ? C14 C15 1.372(2) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 C18 1.515(2) . ? C18 C19 1.390(2) . ? C19 C20 1.382(3) . ? C19 H19A 0.9300 . ? C20 C21 1.376(3) . ? C20 H20A 0.9300 . ? C21 C22 1.389(2) . ? C21 H21A 0.9300 . ? C22 C23 1.516(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 Cd N5 141.19(5) . . ? O7 Cd N4 93.15(5) . 1_644 ? N5 Cd N4 92.34(4) . 1_644 ? O7 Cd N1 87.96(5) . . ? N5 Cd N1 89.58(5) . . ? N4 Cd N1 175.40(5) 1_644 . ? O7 Cd O5 80.45(5) . 2_856 ? N5 Cd O5 138.10(4) . 2_856 ? N4 Cd O5 88.49(4) 1_644 2_856 ? N1 Cd O5 87.29(4) . 2_856 ? O7 Cd O3 73.93(15) . . ? N5 Cd O3 68.24(14) . . ? N4 Cd O3 85.63(12) 1_644 . ? N1 Cd O3 98.97(12) . . ? O5 Cd O3 153.32(14) 2_856 . ? O7 Cd O3' 74.76(16) . . ? N5 Cd O3' 66.76(16) . . ? N4 Cd O3' 91.04(15) 1_644 . ? N1 Cd O3' 93.56(15) . . ? O5 Cd O3' 155.14(16) 2_856 . ? O3 Cd O3' 5.5(2) . . ? O7 Cd O5 150.67(5) . . ? N5 Cd O5 67.51(4) . . ? N4 Cd O5 90.73(4) 1_644 . ? N1 Cd O5 86.14(4) . . ? O5 Cd O5 70.60(4) 2_856 . ? O3 Cd O5 135.38(14) . . ? O3' Cd O5 134.27(15) . . ? C5 N1 C1 117.79(14) . . ? C5 N1 Cd 119.53(11) . . ? C1 N1 Cd 122.67(11) . . ? C6 N2 C4 127.51(15) . . ? C6 N2 H2A 116.2 . . ? C4 N2 H2A 116.2 . . ? C11 N3 C12 128.87(15) . . ? C11 N3 H3B 115.6 . . ? C12 N3 H3B 115.6 . . ? C16 N4 C15 117.72(13) . . ? C16 N4 Cd 119.59(11) . 1_466 ? C15 N4 Cd 122.62(10) . 1_466 ? C18 N5 C22 119.70(14) . . ? C18 N5 Cd 120.43(10) . . ? C22 N5 Cd 119.87(11) . . ? C23 O3 Cd 118.0(3) . . ? C23 O3' Cd 121.1(4) . . ? C17 O5 Cd 131.91(11) . 2_856 ? C17 O5 Cd 118.53(10) . . ? Cd O5 Cd 109.40(4) 2_856 . ? Cd O7 H7E 109.8 . . ? Cd O7 H7C 109.2 . . ? H7E O7 H7C 109.8 . . ? H10C O10 H10D 104.0 . . ? N1 C1 C2 122.29(16) . . ? N1 C1 H1A 118.9 . . ? C2 C1 H1A 118.9 . . ? C1 C2 C3 120.20(17) . . ? C1 C2 H2B 119.9 . . ? C3 C2 H2B 119.9 . . ? C2 C3 C4 118.20(16) . . ? C2 C3 H3A 120.9 . . ? C4 C3 H3A 120.9 . . ? C3 C4 C5 117.87(15) . . ? C3 C4 N2 125.32(15) . . ? C5 C4 N2 116.81(15) . . ? N1 C5 C4 123.64(16) . . ? N1 C5 H5A 118.2 . . ? C4 C5 H5A 118.2 . . ? O1 C6 N2 123.72(16) . . ? O1 C6 C7 123.72(15) . . ? N2 C6 C7 112.55(15) . . ? C6 C7 C8 113.90(15) . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C9 111.79(15) . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? C10 C9 C8 111.49(16) . . ? C10 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? C10 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C9 115.31(16) . . ? C11 C10 H10A 108.4 . . ? C9 C10 H10A 108.4 . . ? C11 C10 H10B 108.4 . . ? C9 C10 H10B 108.4 . . ? H10A C10 H10B 107.5 . . ? O2 C11 N3 123.31(16) . . ? O2 C11 C10 124.16(15) . . ? N3 C11 C10 112.52(15) . . ? C13 C12 C16 117.93(14) . . ? C13 C12 N3 125.09(14) . . ? C16 C12 N3 116.97(14) . . ? C14 C13 C12 117.95(15) . . ? C14 C13 H13A 121.0 . . ? C12 C13 H13A 121.0 . . ? C15 C14 C13 120.48(16) . . ? C15 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? N4 C15 C14 122.12(15) . . ? N4 C15 H15A 118.9 . . ? C14 C15 H15A 118.9 . . ? N4 C16 C12 123.78(15) . . ? N4 C16 H16A 118.1 . . ? C12 C16 H16A 118.1 . . ? O6 C17 O5 126.14(16) . . ? O6 C17 C18 116.98(15) . . ? O5 C17 C18 116.86(14) . . ? N5 C18 C19 121.95(15) . . ? N5 C18 C17 116.38(14) . . ? C19 C18 C17 121.67(15) . . ? C20 C19 C18 118.58(17) . . ? C20 C19 H19A 120.7 . . ? C18 C19 H19A 120.7 . . ? C21 C20 C19 119.31(16) . . ? C21 C20 H20A 120.3 . . ? C19 C20 H20A 120.3 . . ? C20 C21 C22 119.34(16) . . ? C20 C21 H21A 120.3 . . ? C22 C21 H21A 120.3 . . ? N5 C22 C21 121.10(16) . . ? N5 C22 C23 115.76(14) . . ? C21 C22 C23 123.14(15) . . ? O3' C23 O4 126.2(3) . . ? O3' C23 O3 10.2(5) . . ? O4 C23 O3 126.1(3) . . ? O3' C23 C22 116.4(3) . . ? O4 C23 C22 117.07(16) . . ? O3 C23 C22 116.5(3) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.382 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.059 _database_code_depnum_ccdc_archive 'CCDC 949405' ####################################################################### # # 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_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H22 N4 O8 Zn' _chemical_formula_weight 571.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.6305(17) _cell_length_b 15.905(3) _cell_length_c 13.6118(15) _cell_angle_alpha 90.00 _cell_angle_beta 95.368(14) _cell_angle_gamma 90.00 _cell_volume 2506.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 5.21 _cell_measurement_theta_max 12.46 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 1.037 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9097 _exptl_absorpt_correction_T_max 0.9793 _exptl_absorpt_process_details '(XSCANS; Siemens, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5449 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4369 _reflns_number_gt 3574 _reflns_threshold_expression >2sigma(I) _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. ; _computing_data_collection 'XSCANS (Siemens, 1995)' _computing_cell_refinement 'XSCANS (Siemens, 1995)' _computing_data_reduction 'SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0255P)^2^+1.3178P] 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 4369 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0739 _refine_ls_wR_factor_gt 0.0684 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 Zn Zn 0.77024(2) 0.782489(17) -0.080590(17) 0.02656(9) Uani 1 1 d . . . O1 O 1.09500(16) 1.01821(15) 0.29748(14) 0.0582(6) Uani 1 1 d . . . O2 O 0.82734(15) 0.48144(13) 0.26252(12) 0.0458(5) Uani 1 1 d . . . O3 O 0.60513(14) 0.79095(12) -0.07408(11) 0.0383(4) Uani 1 1 d . . . O4 O 0.64221(15) 0.78366(13) 0.08695(11) 0.0442(5) Uani 1 1 d . . . O5 O 0.23547(18) 0.73166(16) -0.23612(13) 0.0649(7) Uani 1 1 d . . . H5B H 0.1902 0.7235 -0.2851 0.078 Uiso 1 1 calc R . . O6 O 0.08507(15) 0.69300(13) -0.15708(13) 0.0473(5) Uani 1 1 d . . . O7 O 0.15933(17) 0.66074(16) 0.21385(14) 0.0616(6) Uani 1 1 d . . . O8 O 0.31275(14) 0.72549(12) 0.28692(11) 0.0382(4) Uani 1 1 d . . . N1 N 0.88633(16) 0.85876(12) -0.00329(14) 0.0299(4) Uani 1 1 d . . . N2 N 0.92084(18) 0.97620(14) 0.22641(14) 0.0384(5) Uani 1 1 d . . . H2A H 0.8483 0.9759 0.2341 0.046 Uiso 1 1 calc R . . N3 N 0.81958(17) 0.66584(13) -0.02575(13) 0.0319(5) Uani 1 1 d . . . N4 N 0.95666(17) 0.56626(13) 0.19842(14) 0.0361(5) Uani 1 1 d . . . H4A H 1.0192 0.5946 0.2114 0.043 Uiso 1 1 calc R . . C1 C 0.8676(2) 0.89644(15) 0.08169(16) 0.0299(5) Uani 1 1 d . . . H1A H 0.7935 0.8950 0.1021 0.036 Uiso 1 1 calc R . . C2 C 0.9536(2) 0.93749(16) 0.14069(17) 0.0333(5) Uani 1 1 d . . . C3 C 1.0648(2) 0.93802(17) 0.11080(19) 0.0406(6) Uani 1 1 d . . . H3A H 1.1253 0.9638 0.1489 0.049 Uiso 1 1 calc R . . C4 C 1.0826(2) 0.89903(17) 0.0227(2) 0.0405(6) Uani 1 1 d . . . H4B H 1.1560 0.8991 0.0008 0.049 Uiso 1 1 calc R . . C5 C 0.9937(2) 0.86032(16) -0.03267(18) 0.0377(6) Uani 1 1 d . . . H5A H 1.0077 0.8346 -0.0917 0.045 Uiso 1 1 calc R . . C6 C 0.9913(2) 1.01430(17) 0.29885(17) 0.0360(6) Uani 1 1 d . . . C7 C 0.9282(2) 1.05257(18) 0.38031(17) 0.0393(6) Uani 1 1 d . . . H7A H 0.8542 1.0248 0.3820 0.047 Uiso 1 1 calc R . . H7B H 0.9136 1.1115 0.3658 0.047 Uiso 1 1 calc R . . C8 C 0.9958(2) 1.04495(16) 0.48138(17) 0.0372(6) Uani 1 1 d . . . H8A H 1.0731 1.0669 0.4776 0.045 Uiso 1 1 calc R . . H8B H 0.9587 1.0791 0.5283 0.045 Uiso 1 1 calc R . . C9 C 0.8702(2) 0.65365(16) 0.06585(17) 0.0316(5) Uani 1 1 d . . . H9A H 0.8876 0.7002 0.1058 0.038 Uiso 1 1 calc R . . C10 C 0.89729(19) 0.57465(15) 0.10297(16) 0.0302(5) Uani 1 1 d . . . C11 C 0.8699(2) 0.50537(16) 0.04430(18) 0.0356(6) Uani 1 1 d . . . H11A H 0.8871 0.4515 0.0677 0.043 Uiso 1 1 calc R . . C12 C 0.8167(2) 0.51727(16) -0.04941(18) 0.0387(6) Uani 1 1 d . . . H12A H 0.7965 0.4715 -0.0899 0.046 Uiso 1 1 calc R . . C13 C 0.7938(2) 0.59804(16) -0.08214(17) 0.0359(6) Uani 1 1 d . . . H13A H 0.7592 0.6059 -0.1459 0.043 Uiso 1 1 calc R . . C14 C 0.9213(2) 0.51672(16) 0.26993(17) 0.0334(6) Uani 1 1 d . . . C15 C 1.0076(2) 0.50590(19) 0.35878(17) 0.0410(6) Uani 1 1 d . . . H15A H 1.0640 0.5509 0.3593 0.049 Uiso 1 1 calc R . . H15B H 1.0483 0.4532 0.3524 0.049 Uiso 1 1 calc R . . C16 C 0.9549(2) 0.50608(17) 0.45630(17) 0.0387(6) Uani 1 1 d . . . H16A H 0.8981 0.4614 0.4561 0.058 Uiso 1 1 calc R . . H16B H 0.9154 0.5591 0.4637 0.058 Uiso 1 1 calc R . . C17 C 0.5740(2) 0.78007(15) 0.01221(15) 0.0277(5) Uani 1 1 d . . . C18 C 0.44972(19) 0.75984(14) 0.01823(15) 0.0246(5) Uani 1 1 d . . . C19 C 0.3773(2) 0.74951(15) -0.06788(16) 0.0284(5) Uani 1 1 d . . . H19A H 0.4052 0.7596 -0.1286 0.034 Uiso 1 1 calc R . . C20 C 0.2640(2) 0.72441(15) -0.06414(15) 0.0283(5) Uani 1 1 d . . . C21 C 0.1844(2) 0.71437(16) -0.15609(17) 0.0338(5) Uani 1 1 d . . . C22 C 0.2227(2) 0.70809(15) 0.02676(16) 0.0286(5) Uani 1 1 d . . . H22A H 0.1471 0.6897 0.0294 0.034 Uiso 1 1 calc R . . C23 C 0.29423(19) 0.71920(14) 0.11371(15) 0.0247(5) Uani 1 1 d . . . C24 C 0.2494(2) 0.69972(15) 0.21153(16) 0.0306(5) Uani 1 1 d . . . C25 C 0.40704(19) 0.74638(14) 0.10933(15) 0.0256(5) Uani 1 1 d . . . H25A H 0.4543 0.7556 0.1673 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn 0.02825(14) 0.03410(15) 0.01745(13) 0.00050(11) 0.00280(9) -0.00083(12) O1 0.0344(11) 0.0968(17) 0.0424(11) -0.0204(11) -0.0009(8) -0.0104(11) O2 0.0346(10) 0.0662(13) 0.0357(10) 0.0108(9) -0.0019(8) -0.0149(10) O3 0.0284(9) 0.0650(12) 0.0221(8) 0.0086(8) 0.0062(7) -0.0006(9) O4 0.0309(9) 0.0788(13) 0.0223(8) 0.0008(9) -0.0004(7) -0.0153(10) O5 0.0525(12) 0.120(2) 0.0206(9) 0.0048(11) -0.0067(8) -0.0233(13) O6 0.0311(10) 0.0747(14) 0.0345(10) -0.0071(9) -0.0048(8) -0.0007(9) O7 0.0521(12) 0.0996(17) 0.0353(10) -0.0146(11) 0.0159(9) -0.0471(13) O8 0.0342(9) 0.0628(12) 0.0182(8) -0.0039(8) 0.0052(7) -0.0134(9) N1 0.0307(11) 0.0302(11) 0.0292(10) -0.0024(8) 0.0038(8) -0.0004(9) N2 0.0276(11) 0.0545(14) 0.0331(11) -0.0124(10) 0.0028(9) -0.0031(10) N3 0.0364(11) 0.0357(11) 0.0229(10) 0.0013(9) -0.0007(8) -0.0014(9) N4 0.0317(11) 0.0453(13) 0.0292(10) 0.0110(9) -0.0081(9) -0.0126(10) C1 0.0247(12) 0.0360(13) 0.0294(12) -0.0013(10) 0.0045(10) -0.0007(10) C2 0.0314(13) 0.0373(14) 0.0310(12) -0.0019(11) 0.0022(10) -0.0005(11) C3 0.0301(13) 0.0471(16) 0.0440(15) -0.0065(13) 0.0004(11) -0.0040(12) C4 0.0256(13) 0.0466(16) 0.0507(16) -0.0056(13) 0.0107(11) 0.0012(12) C5 0.0367(14) 0.0400(15) 0.0378(14) -0.0062(12) 0.0111(11) 0.0012(12) C6 0.0344(15) 0.0427(15) 0.0298(12) -0.0011(11) -0.0026(10) -0.0042(12) C7 0.0390(14) 0.0457(15) 0.0326(13) -0.0060(12) 0.0006(11) 0.0018(12) C8 0.0439(15) 0.0381(14) 0.0292(13) -0.0089(11) 0.0011(11) -0.0045(12) C9 0.0349(13) 0.0336(13) 0.0253(11) 0.0004(10) -0.0027(10) -0.0063(11) C10 0.0252(12) 0.0390(14) 0.0259(12) 0.0055(10) -0.0007(9) -0.0069(10) C11 0.0362(14) 0.0317(13) 0.0383(13) 0.0055(11) 0.0013(11) -0.0020(11) C12 0.0468(16) 0.0345(14) 0.0337(13) -0.0046(11) -0.0027(11) -0.0041(12) C13 0.0427(15) 0.0396(14) 0.0240(11) -0.0019(11) -0.0040(11) -0.0019(12) C14 0.0303(13) 0.0417(14) 0.0275(12) 0.0042(11) -0.0009(10) -0.0027(11) C15 0.0365(14) 0.0535(17) 0.0313(13) 0.0090(12) -0.0057(11) -0.0052(13) C16 0.0444(15) 0.0414(15) 0.0286(12) 0.0064(11) -0.0052(11) -0.0048(12) C17 0.0305(12) 0.0315(12) 0.0215(11) 0.0031(10) 0.0051(9) 0.0003(10) C18 0.0266(12) 0.0271(12) 0.0202(10) 0.0012(9) 0.0033(9) -0.0005(9) C19 0.0338(13) 0.0360(12) 0.0154(10) 0.0028(9) 0.0022(9) -0.0009(11) C20 0.0292(12) 0.0324(12) 0.0225(11) -0.0013(10) -0.0016(9) 0.0018(11) C21 0.0336(14) 0.0432(14) 0.0233(11) -0.0049(11) -0.0038(10) 0.0034(12) C22 0.0251(11) 0.0366(13) 0.0240(11) -0.0049(10) 0.0018(9) -0.0024(10) C23 0.0244(11) 0.0285(11) 0.0215(10) -0.0011(10) 0.0039(9) -0.0012(10) C24 0.0305(12) 0.0379(14) 0.0240(11) -0.0043(10) 0.0062(10) -0.0056(11) C25 0.0291(12) 0.0299(11) 0.0174(10) -0.0015(9) 0.0002(9) -0.0014(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 Zn O8 1.9183(15) 4_675 ? Zn O3 1.9353(16) . ? Zn N1 2.0337(19) . ? Zn N3 2.061(2) . ? O1 C6 1.210(3) . ? O2 C14 1.224(3) . ? O3 C17 1.273(3) . ? O4 C17 1.232(3) . ? O5 C21 1.318(3) . ? O5 H5B 0.8200 . ? O6 C21 1.203(3) . ? O7 C24 1.220(3) . ? O8 C24 1.274(3) . ? O8 Zn 1.9183(15) 4_576 ? N1 C1 1.338(3) . ? N1 C5 1.347(3) . ? N2 C6 1.364(3) . ? N2 C2 1.403(3) . ? N2 H2A 0.8600 . ? N3 C13 1.341(3) . ? N3 C9 1.342(3) . ? N4 C14 1.346(3) . ? N4 C10 1.419(3) . ? N4 H4A 0.8600 . ? C1 C2 1.386(3) . ? C1 H1A 0.9300 . ? C2 C3 1.391(3) . ? C3 C4 1.383(4) . ? C3 H3A 0.9300 . ? C4 C5 1.367(4) . ? C4 H4B 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.513(3) . ? C7 C8 1.524(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C8 1.517(5) 3_776 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.380(3) . ? C9 H9A 0.9300 . ? C10 C11 1.380(3) . ? C11 C12 1.378(3) . ? C11 H11A 0.9300 . ? C12 C13 1.377(4) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 C15 1.508(3) . ? C15 C16 1.513(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C16 1.522(5) 3_766 ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.490(3) . ? C18 C19 1.388(3) . ? C18 C25 1.395(3) . ? C19 C20 1.383(3) . ? C19 H19A 0.9300 . ? C20 C22 1.393(3) . ? C20 C21 1.494(3) . ? C22 C23 1.393(3) . ? C22 H22A 0.9300 . ? C23 C25 1.388(3) . ? C23 C24 1.507(3) . ? C25 H25A 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 Zn O3 113.06(7) 4_675 . ? O8 Zn N1 107.99(8) 4_675 . ? O3 Zn N1 123.26(8) . . ? O8 Zn N3 101.16(8) 4_675 . ? O3 Zn N3 106.85(8) . . ? N1 Zn N3 101.57(8) . . ? C17 O3 Zn 113.71(14) . . ? C21 O5 H5B 109.5 . . ? C24 O8 Zn 123.75(15) . 4_576 ? C1 N1 C5 118.6(2) . . ? C1 N1 Zn 124.10(16) . . ? C5 N1 Zn 116.53(16) . . ? C6 N2 C2 127.2(2) . . ? C6 N2 H2A 116.4 . . ? C2 N2 H2A 116.4 . . ? C13 N3 C9 118.1(2) . . ? C13 N3 Zn 118.47(15) . . ? C9 N3 Zn 123.33(17) . . ? C14 N4 C10 124.1(2) . . ? C14 N4 H4A 117.9 . . ? C10 N4 H4A 117.9 . . ? N1 C1 C2 123.0(2) . . ? N1 C1 H1A 118.5 . . ? C2 C1 H1A 118.5 . . ? C1 C2 C3 118.2(2) . . ? C1 C2 N2 116.8(2) . . ? C3 C2 N2 124.9(2) . . ? C4 C3 C2 118.0(2) . . ? C4 C3 H3A 121.0 . . ? C2 C3 H3A 121.0 . . ? C5 C4 C3 120.9(2) . . ? C5 C4 H4B 119.6 . . ? C3 C4 H4B 119.6 . . ? N1 C5 C4 121.3(2) . . ? N1 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? O1 C6 N2 123.0(2) . . ? O1 C6 C7 122.9(2) . . ? N2 C6 C7 114.1(2) . . ? C6 C7 C8 112.6(2) . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C8 C8 C7 112.8(3) 3_776 . ? C8 C8 H8A 109.0 3_776 . ? C7 C8 H8A 109.0 . . ? C8 C8 H8B 109.0 3_776 . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? N3 C9 C10 122.5(2) . . ? N3 C9 H9A 118.8 . . ? C10 C9 H9A 118.8 . . ? C9 C10 C11 118.9(2) . . ? C9 C10 N4 119.7(2) . . ? C11 C10 N4 121.4(2) . . ? C12 C11 C10 119.0(2) . . ? C12 C11 H11A 120.5 . . ? C10 C11 H11A 120.5 . . ? C13 C12 C11 118.9(2) . . ? C13 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? N3 C13 C12 122.6(2) . . ? N3 C13 H13A 118.7 . . ? C12 C13 H13A 118.7 . . ? O2 C14 N4 122.7(2) . . ? O2 C14 C15 122.4(2) . . ? N4 C14 C15 114.9(2) . . ? C14 C15 C16 114.2(2) . . ? C14 C15 H15A 108.7 . . ? C16 C15 H15A 108.7 . . ? C14 C15 H15B 108.7 . . ? C16 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C15 C16 C16 112.3(3) . 3_766 ? C15 C16 H16A 109.1 . . ? C16 C16 H16A 109.1 3_766 . ? C15 C16 H16B 109.1 . . ? C16 C16 H16B 109.1 3_766 . ? H16A C16 H16B 107.9 . . ? O4 C17 O3 122.6(2) . . ? O4 C17 C18 121.18(19) . . ? O3 C17 C18 116.19(19) . . ? C19 C18 C25 119.6(2) . . ? C19 C18 C17 119.62(19) . . ? C25 C18 C17 120.65(19) . . ? C20 C19 C18 120.6(2) . . ? C20 C19 H19A 119.7 . . ? C18 C19 H19A 119.7 . . ? C19 C20 C22 119.7(2) . . ? C19 C20 C21 121.2(2) . . ? C22 C20 C21 119.1(2) . . ? O6 C21 O5 123.8(2) . . ? O6 C21 C20 124.0(2) . . ? O5 C21 C20 112.2(2) . . ? C20 C22 C23 120.2(2) . . ? C20 C22 H22A 119.9 . . ? C23 C22 H22A 119.9 . . ? C25 C23 C22 119.7(2) . . ? C25 C23 C24 120.58(19) . . ? C22 C23 C24 119.7(2) . . ? O7 C24 O8 125.2(2) . . ? O7 C24 C23 119.8(2) . . ? O8 C24 C23 115.1(2) . . ? C23 C25 C18 120.2(2) . . ? C23 C25 H25A 119.9 . . ? C18 C25 H25A 119.9 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.262 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 949406' ####################################################################### # # 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_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H26 Cd N4 O10' _chemical_formula_weight 654.90 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.3111(2) _cell_length_b 13.8834(3) _cell_length_c 16.8506(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.992(1) _cell_angle_gamma 90.00 _cell_volume 2606.02(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5704 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 23.52 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.904 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8716 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25430 _diffrn_reflns_av_R_equivalents 0.0785 _diffrn_reflns_av_sigmaI/netI 0.1447 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.31 _reflns_number_total 11215 _reflns_number_gt 6813 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2010)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0101P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(2) _refine_ls_number_reflns 11215 _refine_ls_number_parameters 721 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1255 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.0806 _refine_ls_wR_factor_gt 0.0658 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _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 -0.48022(4) 0.71067(4) 0.25313(3) 0.03047(14) Uani 1 1 d . . . Cd2 Cd 0.01613(4) 0.58392(3) 0.28183(3) 0.02811(13) Uani 1 1 d . . . O1 O 0.0099(4) 0.8693(4) 0.5734(3) 0.0552(17) Uani 1 1 d . . . O2 O 0.5076(5) 1.0426(5) 0.3509(3) 0.087(3) Uani 1 1 d . . . O3 O -0.4964(5) 0.4779(5) -0.0530(3) 0.060(2) Uani 1 1 d . . . O4 O -1.0199(5) 0.2750(4) 0.1046(3) 0.0542(18) Uani 1 1 d . . . O5 O -0.3929(5) 0.8513(4) 0.2296(3) 0.0455(15) Uani 1 1 d . . . O6 O -0.2782(5) 0.7343(4) 0.1993(3) 0.0441(15) Uani 1 1 d . . . O7 O -0.0353(4) 0.7382(3) 0.2998(3) 0.0292(13) Uani 1 1 d . . . O8 O 0.0128(4) 0.7311(3) 0.1797(3) 0.0354(14) Uani 1 1 d . . . O9 O 0.1797(5) 0.8728(4) 0.2696(3) 0.0444(16) Uani 1 1 d . . . O10 O 0.1907(4) 0.9862(4) 0.1790(3) 0.0511(16) Uani 1 1 d . . . H10C H 0.2642 0.9907 0.1873 0.061 Uiso 1 1 d R . . O11 O -0.4898(4) 0.5532(4) 0.2312(3) 0.0343(15) Uani 1 1 d . . . O12 O -0.5309(4) 0.5377(3) 0.3554(3) 0.0385(14) Uani 1 1 d . . . O13 O -0.7740(4) 0.5530(4) 0.2447(3) 0.0336(14) Uani 1 1 d . . . O14 O -0.8880(4) 0.4397(4) 0.2812(3) 0.0426(14) Uani 1 1 d . . . H14C H -0.9231 0.4011 0.2455 0.051 Uiso 1 1 d R . . O15 O -0.3074(5) 0.2801(4) 0.2381(3) 0.0555(17) Uani 1 1 d . . . O16 O -0.3207(5) 0.4078(4) 0.3146(4) 0.0558(18) Uani 1 1 d . . . O17 O -0.6547(4) 0.7286(4) 0.3039(2) 0.0406(14) Uani 1 1 d . . . H17C H -0.6945 0.6764 0.2972 0.049 Uiso 1 1 d R . . H17D H -0.6956 0.7744 0.2793 0.049 Uiso 1 1 d R . . O18 O -0.1267(4) 0.5212(4) 0.3511(3) 0.0457(15) Uani 1 1 d . . . H18C H -0.1908 0.5464 0.3259 0.055 Uiso 1 1 d R . . H18D H -0.1367 0.4619 0.3395 0.069 Uiso 1 1 d R . . O19 O 0.4124(5) 0.9787(4) 0.2065(3) 0.071(2) Uani 1 1 d . . . H19C H 0.4436 0.9451 0.1733 0.085 Uiso 1 1 d R . . H19D H 0.4670 1.0047 0.2408 0.085 Uiso 1 1 d R . . O20 O -0.0744(5) 0.2897(4) 0.2602(3) 0.0560(17) Uani 1 1 d . . . H20C H -0.1414 0.2979 0.2292 0.067 Uiso 1 1 d R . . H20D H -0.0732 0.3201 0.3041 0.067 Uiso 1 1 d R . . N1 N -0.3787(5) 0.7429(4) 0.3853(3) 0.0310(17) Uani 1 1 d . . . N2 N -0.0656(5) 0.8069(5) 0.4523(4) 0.0363(18) Uani 1 1 d . . . H2A H -0.0460 0.7897 0.4073 0.044 Uiso 1 1 calc R . . N3 N 0.5674(5) 1.0615(5) 0.4825(3) 0.046(2) Uani 1 1 d . . . H3A H 0.5426 1.0632 0.5279 0.056 Uiso 1 1 calc R . . N4 N 0.8789(5) 1.0910(5) 0.5770(3) 0.0332(15) Uani 1 1 d . . . N5 N -0.1103(5) 0.5407(4) 0.1612(3) 0.0296(16) Uani 1 1 d . . . N6 N -0.4259(5) 0.5055(4) 0.0794(3) 0.0306(16) Uani 1 1 d . . . H6A H -0.4478 0.5110 0.1255 0.037 Uiso 1 1 calc R . . N7 N -1.0877(5) 0.2600(4) -0.0298(3) 0.0308(16) Uani 1 1 d . . . H7A H -1.0636 0.2592 -0.0755 0.037 Uiso 1 1 calc R . . N8 N -1.3997(5) 0.2287(5) -0.1206(3) 0.0310(17) Uani 1 1 d . . . C1 C -0.4296(7) 0.7719(6) 0.4486(5) 0.038(2) Uani 1 1 d . . . H1A H -0.5121 0.7652 0.4457 0.046 Uiso 1 1 calc R . . C2 C -0.3628(6) 0.8109(6) 0.5168(4) 0.044(2) Uani 1 1 d . . . H2B H -0.4004 0.8288 0.5595 0.053 Uiso 1 1 calc R . . C3 C -0.2398(6) 0.8242(6) 0.5231(4) 0.041(2) Uani 1 1 d . . . H3B H -0.1942 0.8511 0.5689 0.050 Uiso 1 1 calc R . . C4 C -0.1877(7) 0.7956(6) 0.4580(5) 0.034(2) Uani 1 1 d . . . C5 C -0.2599(7) 0.7540(5) 0.3927(4) 0.035(2) Uani 1 1 d . . . H5A H -0.2234 0.7322 0.3507 0.042 Uiso 1 1 calc R . . C6 C 0.0233(6) 0.8406(6) 0.5076(5) 0.038(2) Uani 1 1 d . . . C7 C 0.1465(6) 0.8408(6) 0.4823(5) 0.045(2) Uani 1 1 d . . . H7B H 0.2046 0.8125 0.5250 0.054 Uiso 1 1 calc R . . H7C H 0.1433 0.8010 0.4346 0.054 Uiso 1 1 calc R . . C8 C 0.1877(6) 0.9402(6) 0.4644(5) 0.045(2) Uani 1 1 d . . . H8B H 0.1768 0.9828 0.5083 0.054 Uiso 1 1 calc R . . H8C H 0.1373 0.9639 0.4158 0.054 Uiso 1 1 calc R . . C9 C 0.3177(7) 0.9449(6) 0.4533(5) 0.050(2) Uani 1 1 d . . . H9A H 0.3685 0.9218 0.5019 0.060 Uiso 1 1 calc R . . H9B H 0.3289 0.9024 0.4095 0.060 Uiso 1 1 calc R . . C10 C 0.3564(6) 1.0451(6) 0.4351(5) 0.051(2) Uani 1 1 d . . . H10A H 0.3515 1.0864 0.4809 0.062 Uiso 1 1 calc R . . H10B H 0.3015 1.0702 0.3891 0.062 Uiso 1 1 calc R . . C11 C 0.4835(7) 1.0483(6) 0.4172(5) 0.051(3) Uani 1 1 d . . . C12 C 0.6915(6) 1.0727(6) 0.4857(4) 0.0323(18) Uani 1 1 d . . . C13 C 0.7502(6) 1.0779(7) 0.4209(4) 0.053(2) Uani 1 1 d . . . H13A H 0.7079 1.0733 0.3686 0.064 Uiso 1 1 calc R . . C14 C 0.8722(6) 1.0901(7) 0.4350(4) 0.057(2) Uani 1 1 d . . . H14A H 0.9132 1.0947 0.3918 0.069 Uiso 1 1 calc R . . C15 C 0.9345(6) 1.0954(6) 0.5126(4) 0.040(2) Uani 1 1 d . . . H15A H 1.0175 1.1023 0.5208 0.048 Uiso 1 1 calc R . . C16 C 0.7607(6) 1.0780(6) 0.5615(4) 0.0339(19) Uani 1 1 d . . . H16A H 0.7214 1.0721 0.6053 0.041 Uiso 1 1 calc R . . C17 C -0.0592(6) 0.5339(5) 0.0954(4) 0.034(2) Uani 1 1 d . . . H17B H 0.0237 0.5395 0.1006 0.041 Uiso 1 1 calc R . . C18 C -0.1261(7) 0.5187(6) 0.0207(5) 0.042(2) Uani 1 1 d . . . H18B H -0.0885 0.5158 -0.0241 0.050 Uiso 1 1 calc R . . C19 C -0.2485(7) 0.5077(6) 0.0113(4) 0.035(2) Uani 1 1 d . . . H19A H -0.2943 0.4971 -0.0394 0.043 Uiso 1 1 calc R . . C20 C -0.3013(6) 0.5125(5) 0.0781(4) 0.0257(19) Uani 1 1 d . . . C21 C -0.2262(6) 0.5310(5) 0.1517(4) 0.032(2) Uani 1 1 d . . . H21A H -0.2619 0.5367 0.1972 0.038 Uiso 1 1 calc R . . C22 C -0.5144(7) 0.4909(6) 0.0146(5) 0.036(2) Uani 1 1 d . . . C23 C -0.6396(6) 0.4841(6) 0.0362(4) 0.040(2) Uani 1 1 d . . . H23A H -0.6355 0.5009 0.0925 0.049 Uiso 1 1 calc R . . H23B H -0.6920 0.5300 0.0041 0.049 Uiso 1 1 calc R . . C24 C -0.6915(6) 0.3845(5) 0.0217(5) 0.035(2) Uani 1 1 d . . . H24A H -0.6468 0.3405 0.0605 0.042 Uiso 1 1 calc R . . H24B H -0.6821 0.3633 -0.0317 0.042 Uiso 1 1 calc R . . C25 C -0.8258(6) 0.3797(6) 0.0288(5) 0.036(2) Uani 1 1 d . . . H25A H -0.8360 0.4031 0.0814 0.043 Uiso 1 1 calc R . . H25B H -0.8714 0.4214 -0.0115 0.043 Uiso 1 1 calc R . . C26 C -0.8745(6) 0.2778(5) 0.0174(4) 0.035(2) Uani 1 1 d . . . H26A H -0.8219 0.2346 0.0525 0.041 Uiso 1 1 calc R . . H26B H -0.8744 0.2578 -0.0378 0.041 Uiso 1 1 calc R . . C27 C -1.0009(7) 0.2691(6) 0.0355(5) 0.037(2) Uani 1 1 d . . . C28 C -1.2118(7) 0.2516(5) -0.0331(4) 0.026(2) Uani 1 1 d . . . C29 C -1.2702(7) 0.2621(5) 0.0314(4) 0.035(2) Uani 1 1 d . . . H29A H -1.2275 0.2756 0.0825 0.042 Uiso 1 1 calc R . . C30 C -1.3925(7) 0.2524(5) 0.0190(5) 0.038(2) Uani 1 1 d . . . H30A H -1.4331 0.2575 0.0623 0.045 Uiso 1 1 calc R . . C31 C -1.4556(7) 0.2350(6) -0.0570(4) 0.040(2) Uani 1 1 d . . . H31A H -1.5385 0.2274 -0.0643 0.048 Uiso 1 1 calc R . . C32 C -1.2789(6) 0.2342(5) -0.1078(4) 0.034(2) Uani 1 1 d . . . H32A H -1.2394 0.2260 -0.1514 0.040 Uiso 1 1 calc R . . C33 C -0.5283(6) 0.5074(6) 0.2862(4) 0.0281(19) Uani 1 1 d . . . C34 C -0.5773(6) 0.4077(5) 0.2644(4) 0.0198(16) Uani 1 1 d . . . C35 C -0.7001(6) 0.3899(5) 0.2528(4) 0.0219(17) Uani 1 1 d . . . C36 C -0.7921(7) 0.4672(6) 0.2602(4) 0.0298(19) Uani 1 1 d . . . C37 C -0.7435(7) 0.2976(6) 0.2327(4) 0.036(2) Uani 1 1 d . . . H37A H -0.8257 0.2863 0.2257 0.043 Uiso 1 1 calc R . . C38 C -0.6681(6) 0.2229(6) 0.2231(4) 0.042(2) Uani 1 1 d . . . H38A H -0.6989 0.1618 0.2094 0.050 Uiso 1 1 calc R . . C39 C -0.5459(6) 0.2392(6) 0.2340(4) 0.040(2) Uani 1 1 d . . . H39A H -0.4938 0.1892 0.2271 0.048 Uiso 1 1 calc R . . C40 C -0.5011(6) 0.3303(6) 0.2551(4) 0.0279(19) Uani 1 1 d . . . C41 C -0.3675(7) 0.3444(6) 0.2720(5) 0.037(2) Uani 1 1 d . . . C42 C -0.2963(7) 0.8209(6) 0.2106(4) 0.0301(19) Uani 1 1 d . . . C43 C -0.2024(7) 0.8949(6) 0.2044(4) 0.0288(19) Uani 1 1 d . . . C44 C -0.2415(7) 0.9898(6) 0.1883(5) 0.043(2) Uani 1 1 d . . . H44A H -0.3228 1.0040 0.1830 0.052 Uiso 1 1 calc R . . C45 C -0.1607(7) 1.0627(6) 0.1803(4) 0.043(2) Uani 1 1 d . . . H45A H -0.1881 1.1252 0.1689 0.052 Uiso 1 1 calc R . . C46 C -0.0411(7) 1.0427(6) 0.1890(4) 0.039(2) Uani 1 1 d . . . H46A H 0.0129 1.0915 0.1830 0.047 Uiso 1 1 calc R . . C47 C 0.0006(6) 0.9488(6) 0.2071(4) 0.0266(18) Uani 1 1 d . . . C48 C 0.1321(7) 0.9316(6) 0.2215(4) 0.032(2) Uani 1 1 d . . . C49 C -0.0780(7) 0.8746(5) 0.2136(4) 0.0263(19) Uani 1 1 d . . . C50 C -0.0308(6) 0.7741(5) 0.2327(4) 0.0250(19) 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 0.0236(3) 0.0343(4) 0.0324(3) -0.0020(3) 0.0018(3) -0.0033(3) Cd2 0.0226(3) 0.0281(3) 0.0322(3) 0.0005(3) 0.0008(2) 0.0010(3) O1 0.043(3) 0.087(5) 0.038(3) -0.029(3) 0.012(3) -0.014(3) O2 0.051(4) 0.172(8) 0.036(3) 0.001(4) 0.002(3) -0.036(4) O3 0.045(4) 0.111(6) 0.025(3) -0.018(3) 0.007(3) -0.020(4) O4 0.036(3) 0.102(5) 0.021(3) -0.010(3) -0.005(3) -0.019(3) O5 0.031(3) 0.039(4) 0.067(4) 0.003(3) 0.010(3) 0.002(3) O6 0.047(3) 0.033(4) 0.053(3) -0.007(3) 0.008(3) -0.005(3) O7 0.040(3) 0.024(3) 0.025(3) 0.008(2) 0.011(2) 0.005(2) O8 0.044(3) 0.028(4) 0.039(3) -0.004(3) 0.021(2) 0.003(3) O9 0.029(3) 0.039(4) 0.062(4) 0.014(3) 0.000(3) 0.002(3) O10 0.025(3) 0.067(4) 0.061(4) 0.016(3) 0.005(3) -0.005(3) O11 0.038(3) 0.032(4) 0.036(3) -0.003(2) 0.014(3) -0.008(3) O12 0.040(3) 0.054(4) 0.023(3) -0.016(2) 0.011(2) -0.007(3) O13 0.034(3) 0.027(4) 0.040(3) 0.004(2) 0.007(2) 0.006(3) O14 0.020(3) 0.044(4) 0.064(4) -0.006(3) 0.011(3) 0.003(3) O15 0.028(3) 0.061(4) 0.079(4) -0.028(3) 0.013(3) 0.007(3) O16 0.029(4) 0.054(5) 0.082(5) -0.029(4) 0.006(3) -0.008(3) O17 0.033(3) 0.045(4) 0.043(3) 0.002(3) 0.005(2) 0.004(3) O18 0.040(3) 0.054(4) 0.040(3) 0.007(3) -0.003(3) -0.012(3) O19 0.033(4) 0.108(6) 0.071(4) -0.025(4) 0.005(3) 0.005(4) O20 0.036(3) 0.072(5) 0.059(4) -0.027(3) 0.008(3) -0.003(3) N1 0.014(3) 0.042(5) 0.036(4) -0.001(3) 0.002(3) -0.002(3) N2 0.025(4) 0.056(5) 0.028(4) -0.015(3) 0.004(3) -0.005(3) N3 0.027(3) 0.081(6) 0.029(4) -0.006(4) 0.001(3) -0.002(4) N4 0.033(4) 0.028(4) 0.038(4) 0.005(4) 0.005(3) -0.002(3) N5 0.028(4) 0.035(4) 0.026(4) 0.000(3) 0.005(3) 0.000(3) N6 0.022(3) 0.047(4) 0.024(3) -0.003(3) 0.007(3) -0.008(3) N7 0.021(3) 0.051(5) 0.021(3) -0.004(3) 0.005(3) -0.009(3) N8 0.027(4) 0.034(5) 0.028(3) -0.010(3) -0.007(3) -0.003(3) C1 0.028(4) 0.044(6) 0.044(5) 0.003(4) 0.010(4) 0.004(4) C2 0.030(4) 0.070(7) 0.035(5) -0.023(5) 0.010(4) 0.007(4) C3 0.035(5) 0.052(6) 0.037(5) -0.014(4) 0.006(4) -0.004(4) C4 0.033(4) 0.035(5) 0.033(5) -0.003(4) 0.002(4) -0.005(4) C5 0.036(5) 0.042(6) 0.026(5) -0.011(4) 0.002(4) -0.003(4) C6 0.025(5) 0.039(5) 0.050(6) 0.000(4) 0.010(5) -0.004(4) C7 0.025(4) 0.055(6) 0.056(6) -0.017(5) 0.013(4) -0.006(4) C8 0.025(4) 0.054(6) 0.057(6) -0.017(5) 0.010(4) -0.013(4) C9 0.038(5) 0.056(7) 0.056(6) -0.015(5) 0.009(5) -0.004(5) C10 0.041(5) 0.046(6) 0.065(6) 0.011(4) 0.001(4) 0.002(4) C11 0.032(5) 0.074(8) 0.043(5) 0.002(5) -0.004(4) -0.018(4) C12 0.027(4) 0.043(5) 0.024(4) 0.001(4) -0.004(3) 0.001(4) C13 0.035(4) 0.100(7) 0.026(4) -0.001(6) 0.008(3) 0.002(6) C14 0.035(4) 0.106(8) 0.033(4) 0.016(6) 0.013(4) -0.004(6) C15 0.027(4) 0.048(6) 0.044(5) 0.002(5) 0.004(4) 0.003(4) C16 0.032(4) 0.041(5) 0.032(4) 0.001(5) 0.014(3) 0.009(5) C17 0.012(4) 0.044(6) 0.047(5) -0.004(4) 0.007(4) -0.006(4) C18 0.041(5) 0.067(7) 0.023(5) -0.009(4) 0.018(4) -0.004(5) C19 0.034(5) 0.045(6) 0.027(5) -0.015(4) 0.002(4) 0.001(4) C20 0.021(4) 0.028(5) 0.028(4) 0.005(4) 0.004(4) 0.006(4) C21 0.026(4) 0.037(5) 0.034(5) 0.001(4) 0.008(4) 0.003(4) C22 0.024(4) 0.042(6) 0.040(5) -0.010(4) -0.001(4) -0.009(4) C23 0.016(4) 0.056(6) 0.047(5) -0.006(4) -0.001(4) -0.010(4) C24 0.020(4) 0.043(6) 0.043(5) -0.002(4) 0.008(4) 0.002(4) C25 0.020(4) 0.051(6) 0.037(5) -0.006(4) 0.004(4) -0.005(4) C26 0.026(4) 0.042(6) 0.034(5) -0.012(4) 0.003(4) -0.004(4) C27 0.026(5) 0.045(6) 0.038(5) -0.007(4) 0.002(4) -0.008(4) C28 0.022(4) 0.028(5) 0.027(4) 0.004(4) 0.001(4) -0.004(3) C29 0.034(5) 0.044(6) 0.025(4) 0.002(4) 0.002(4) -0.005(4) C30 0.023(4) 0.051(6) 0.040(5) -0.010(4) 0.008(4) -0.005(4) C31 0.025(4) 0.050(7) 0.046(5) -0.006(4) 0.011(4) 0.003(4) C32 0.024(4) 0.047(6) 0.028(4) -0.003(4) 0.000(3) -0.006(4) C33 0.014(4) 0.027(5) 0.043(5) 0.004(4) 0.006(4) 0.003(4) C34 0.016(4) 0.024(5) 0.019(4) 0.006(3) 0.002(3) 0.000(3) C35 0.021(4) 0.023(5) 0.020(4) 0.005(3) 0.000(3) -0.002(3) C36 0.027(4) 0.040(6) 0.020(4) 0.000(4) -0.001(3) 0.005(4) C37 0.023(4) 0.035(5) 0.046(5) -0.005(4) -0.003(4) -0.008(4) C38 0.021(4) 0.022(5) 0.080(6) -0.007(5) 0.003(4) -0.001(4) C39 0.029(5) 0.032(6) 0.058(5) -0.001(4) 0.005(4) 0.012(4) C40 0.019(4) 0.026(5) 0.037(5) 0.008(4) 0.002(4) -0.007(4) C41 0.029(5) 0.042(6) 0.039(5) 0.004(4) 0.003(4) 0.000(4) C42 0.033(5) 0.027(5) 0.027(4) 0.000(4) -0.004(4) 0.006(4) C43 0.024(4) 0.032(5) 0.030(4) 0.004(4) 0.000(4) 0.002(4) C44 0.021(4) 0.041(6) 0.063(6) 0.006(5) -0.002(4) -0.001(4) C45 0.044(5) 0.025(6) 0.058(5) 0.012(4) 0.001(4) 0.001(4) C46 0.033(5) 0.030(5) 0.051(5) 0.014(4) -0.003(4) -0.012(4) C47 0.024(4) 0.031(5) 0.023(4) -0.003(3) 0.000(3) 0.000(4) C48 0.043(5) 0.023(5) 0.032(5) -0.004(4) 0.011(4) -0.002(4) C49 0.032(4) 0.034(5) 0.011(4) 0.001(3) -0.004(3) -0.005(4) C50 0.014(4) 0.021(5) 0.036(5) 0.010(4) -0.005(3) -0.008(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 O11 2.217(5) . ? Cd1 O5 2.254(5) . ? Cd1 O17 2.297(4) . ? Cd1 N1 2.365(6) . ? Cd1 N8 2.416(5) 2_355 ? Cd1 O6 2.621(5) . ? Cd2 O7 2.254(4) . ? Cd2 O14 2.278(5) 1_655 ? Cd2 O18 2.320(5) . ? Cd2 N5 2.351(6) . ? Cd2 N4 2.469(5) 2_646 ? Cd2 O13 2.593(5) 1_655 ? O1 C6 1.213(9) . ? O2 C11 1.198(9) . ? O3 C22 1.205(8) . ? O4 C27 1.222(8) . ? O5 C42 1.263(8) . ? O6 C42 1.239(8) . ? O7 C50 1.245(8) . ? O8 C50 1.244(8) . ? O9 C48 1.209(8) . ? O10 C48 1.301(8) . ? O10 H10C 0.8210 . ? O11 C33 1.263(8) . ? O12 C33 1.243(8) . ? O13 C36 1.244(8) . ? O13 Cd2 2.593(5) 1_455 ? O14 C36 1.257(8) . ? O14 Cd2 2.278(5) 1_455 ? O14 H14C 0.8500 . ? O15 C41 1.312(9) . ? O16 C41 1.199(9) . ? O17 H17C 0.8500 . ? O17 H17D 0.8501 . ? O18 H18C 0.8500 . ? O18 H18D 0.8500 . ? O19 H19C 0.8500 . ? O19 H19D 0.8499 . ? O20 H20C 0.8500 . ? O20 H20D 0.8498 . ? N1 C5 1.336(8) . ? N1 C1 1.358(9) . ? N2 C6 1.331(9) . ? N2 C4 1.409(9) . ? N2 H2A 0.8600 . ? N3 C11 1.335(8) . ? N3 C12 1.404(8) . ? N3 H3A 0.8600 . ? N4 C16 1.329(8) . ? N4 C15 1.348(8) . ? N4 Cd2 2.469(5) 2_656 ? N5 C21 1.300(8) . ? N5 C17 1.340(8) . ? N6 C22 1.362(8) . ? N6 C20 1.418(8) . ? N6 H6A 0.8600 . ? N7 C27 1.348(9) . ? N7 C28 1.400(9) . ? N7 H7A 0.8600 . ? N8 C31 1.339(8) . ? N8 C32 1.348(8) . ? N8 Cd1 2.416(5) 2_345 ? C1 C2 1.373(9) . ? C1 H1A 0.9300 . ? C2 C3 1.388(9) . ? C2 H2B 0.9300 . ? C3 C4 1.391(9) . ? C3 H3B 0.9300 . ? C4 C5 1.378(9) . ? C5 H5A 0.9300 . ? C6 C7 1.526(9) . ? C7 C8 1.504(11) . ? C7 H7B 0.9700 . ? C7 H7C 0.9700 . ? C8 C9 1.516(9) . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 C10 1.506(10) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.520(10) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C13 1.374(8) . ? C12 C16 1.380(8) . ? C13 C14 1.370(9) . ? C13 H13A 0.9300 . ? C14 C15 1.375(8) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 C18 1.367(9) . ? C17 H17B 0.9300 . ? C18 C19 1.375(10) . ? C18 H18B 0.9300 . ? C19 C20 1.363(9) . ? C19 H19A 0.9300 . ? C20 C21 1.400(9) . ? C21 H21A 0.9300 . ? C22 C23 1.524(10) . ? C23 C24 1.505(10) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.545(8) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.518(9) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.519(10) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C28 C32 1.374(9) . ? C28 C29 1.375(10) . ? C29 C30 1.369(10) . ? C29 H29A 0.9300 . ? C30 C31 1.376(9) . ? C30 H30A 0.9300 . ? C31 H31A 0.9300 . ? C32 H32A 0.9300 . ? C33 C34 1.513(10) . ? C34 C35 1.391(9) . ? C34 C40 1.404(10) . ? C35 C37 1.393(9) . ? C35 C36 1.515(10) . ? C37 C38 1.370(10) . ? C37 H37A 0.9300 . ? C38 C39 1.381(9) . ? C38 H38A 0.9300 . ? C39 C40 1.386(10) . ? C39 H39A 0.9300 . ? C40 C41 1.501(9) . ? C42 C43 1.495(10) . ? C43 C44 1.400(10) . ? C43 C49 1.418(10) . ? C44 C45 1.386(10) . ? C44 H44A 0.9300 . ? C45 C46 1.364(9) . ? C45 H45A 0.9300 . ? C46 C47 1.402(10) . ? C46 H46A 0.9300 . ? C47 C49 1.378(10) . ? C47 C48 1.484(10) . ? C49 C50 1.509(10) . ? 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 O11 Cd1 O5 146.62(19) . . ? O11 Cd1 O17 98.57(18) . . ? O5 Cd1 O17 113.74(18) . . ? O11 Cd1 N1 110.19(19) . . ? O5 Cd1 N1 81.15(19) . . ? O17 Cd1 N1 86.40(17) . . ? O11 Cd1 N8 86.9(2) . 2_355 ? O5 Cd1 N8 86.6(2) . 2_355 ? O17 Cd1 N8 87.20(18) . 2_355 ? N1 Cd1 N8 162.5(2) . 2_355 ? O11 Cd1 O6 94.93(17) . . ? O5 Cd1 O6 52.83(17) . . ? O17 Cd1 O6 166.48(18) . . ? N1 Cd1 O6 89.54(17) . . ? N8 Cd1 O6 92.95(18) 2_355 . ? O7 Cd2 O14 165.97(17) . 1_655 ? O7 Cd2 O18 94.05(18) . . ? O14 Cd2 O18 92.64(17) 1_655 . ? O7 Cd2 N5 103.07(18) . . ? O14 Cd2 N5 89.45(19) 1_655 . ? O18 Cd2 N5 88.12(18) . . ? O7 Cd2 N4 85.7(2) . 2_646 ? O14 Cd2 N4 83.7(2) 1_655 2_646 ? O18 Cd2 N4 77.91(18) . 2_646 ? N5 Cd2 N4 164.1(2) . 2_646 ? O7 Cd2 O13 117.26(16) . 1_655 ? O14 Cd2 O13 52.92(16) 1_655 1_655 ? O18 Cd2 O13 143.66(17) . 1_655 ? N5 Cd2 O13 101.19(18) . 1_655 ? N4 Cd2 O13 86.09(17) 2_646 1_655 ? C42 O5 Cd1 100.3(5) . . ? C42 O6 Cd1 83.7(5) . . ? C50 O7 Cd2 101.9(4) . . ? C48 O10 H10C 123.3 . . ? C33 O11 Cd1 112.8(5) . . ? C36 O13 Cd2 85.2(4) . 1_455 ? C36 O14 Cd2 99.7(5) . 1_455 ? C36 O14 H14C 108.2 . . ? Cd2 O14 H14C 113.1 1_455 . ? Cd1 O17 H17C 109.1 . . ? Cd1 O17 H17D 109.2 . . ? H17C O17 H17D 110.1 . . ? Cd2 O18 H18C 101.7 . . ? Cd2 O18 H18D 108.9 . . ? H18C O18 H18D 102.5 . . ? H19C O19 H19D 110.3 . . ? H20C O20 H20D 110.2 . . ? C5 N1 C1 116.6(6) . . ? C5 N1 Cd1 115.2(5) . . ? C1 N1 Cd1 126.4(5) . . ? C6 N2 C4 128.5(7) . . ? C6 N2 H2A 115.8 . . ? C4 N2 H2A 115.8 . . ? C11 N3 C12 127.6(6) . . ? C11 N3 H3A 116.2 . . ? C12 N3 H3A 116.2 . . ? C16 N4 C15 116.2(6) . . ? C16 N4 Cd2 118.9(5) . 2_656 ? C15 N4 Cd2 124.4(5) . 2_656 ? C21 N5 C17 117.5(6) . . ? C21 N5 Cd2 125.6(5) . . ? C17 N5 Cd2 116.6(5) . . ? C22 N6 C20 126.4(6) . . ? C22 N6 H6A 116.8 . . ? C20 N6 H6A 116.8 . . ? C27 N7 C28 128.5(6) . . ? C27 N7 H7A 115.7 . . ? C28 N7 H7A 115.7 . . ? C31 N8 C32 118.3(6) . . ? C31 N8 Cd1 118.6(5) . 2_345 ? C32 N8 Cd1 123.1(5) . 2_345 ? N1 C1 C2 121.8(7) . . ? N1 C1 H1A 119.1 . . ? C2 C1 H1A 119.1 . . ? C1 C2 C3 121.0(7) . . ? C1 C2 H2B 119.5 . . ? C3 C2 H2B 119.5 . . ? C2 C3 C4 117.3(7) . . ? C2 C3 H3B 121.4 . . ? C4 C3 H3B 121.4 . . ? C5 C4 C3 118.4(7) . . ? C5 C4 N2 116.5(7) . . ? C3 C4 N2 125.2(7) . . ? N1 C5 C4 124.8(7) . . ? N1 C5 H5A 117.6 . . ? C4 C5 H5A 117.6 . . ? O1 C6 N2 123.8(7) . . ? O1 C6 C7 121.3(7) . . ? N2 C6 C7 114.8(7) . . ? C8 C7 C6 112.7(7) . . ? C8 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? C8 C7 H7C 109.0 . . ? C6 C7 H7C 109.0 . . ? H7B C7 H7C 107.8 . . ? C7 C8 C9 113.9(7) . . ? C7 C8 H8B 108.8 . . ? C9 C8 H8B 108.8 . . ? C7 C8 H8C 108.8 . . ? C9 C8 H8C 108.8 . . ? H8B C8 H8C 107.7 . . ? C10 C9 C8 112.7(7) . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C9 C10 C11 112.7(7) . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? O2 C11 N3 122.2(8) . . ? O2 C11 C10 124.0(8) . . ? N3 C11 C10 113.7(7) . . ? C13 C12 C16 117.2(6) . . ? C13 C12 N3 126.4(6) . . ? C16 C12 N3 116.4(6) . . ? C14 C13 C12 118.7(6) . . ? C14 C13 H13A 120.6 . . ? C12 C13 H13A 120.6 . . ? C13 C14 C15 120.4(6) . . ? C13 C14 H14A 119.8 . . ? C15 C14 H14A 119.8 . . ? N4 C15 C14 122.0(7) . . ? N4 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? N4 C16 C12 125.4(6) . . ? N4 C16 H16A 117.3 . . ? C12 C16 H16A 117.3 . . ? N5 C17 C18 121.5(7) . . ? N5 C17 H17B 119.2 . . ? C18 C17 H17B 119.2 . . ? C17 C18 C19 120.6(7) . . ? C17 C18 H18B 119.7 . . ? C19 C18 H18B 119.7 . . ? C20 C19 C18 118.4(7) . . ? C20 C19 H19A 120.8 . . ? C18 C19 H19A 120.8 . . ? C19 C20 C21 117.1(7) . . ? C19 C20 N6 126.0(7) . . ? C21 C20 N6 116.8(6) . . ? N5 C21 C20 124.9(7) . . ? N5 C21 H21A 117.6 . . ? C20 C21 H21A 117.6 . . ? O3 C22 N6 123.9(7) . . ? O3 C22 C23 122.2(7) . . ? N6 C22 C23 113.7(7) . . ? C24 C23 C22 111.8(6) . . ? C24 C23 H23A 109.3 . . ? C22 C23 H23A 109.3 . . ? C24 C23 H23B 109.3 . . ? C22 C23 H23B 109.3 . . ? H23A C23 H23B 107.9 . . ? C23 C24 C25 112.9(6) . . ? C23 C24 H24A 109.0 . . ? C25 C24 H24A 109.0 . . ? C23 C24 H24B 109.0 . . ? C25 C24 H24B 109.0 . . ? H24A C24 H24B 107.8 . . ? C26 C25 C24 111.7(6) . . ? C26 C25 H25A 109.3 . . ? C24 C25 H25A 109.3 . . ? C26 C25 H25B 109.3 . . ? C24 C25 H25B 109.3 . . ? H25A C25 H25B 107.9 . . ? C25 C26 C27 112.4(6) . . ? C25 C26 H26A 109.1 . . ? C27 C26 H26A 109.1 . . ? C25 C26 H26B 109.1 . . ? C27 C26 H26B 109.1 . . ? H26A C26 H26B 107.9 . . ? O4 C27 N7 124.1(7) . . ? O4 C27 C26 120.9(7) . . ? N7 C27 C26 114.9(7) . . ? C32 C28 C29 118.5(7) . . ? C32 C28 N7 116.3(7) . . ? C29 C28 N7 125.2(7) . . ? C30 C29 C28 118.7(7) . . ? C30 C29 H29A 120.6 . . ? C28 C29 H29A 120.6 . . ? C29 C30 C31 120.4(7) . . ? C29 C30 H30A 119.8 . . ? C31 C30 H30A 119.8 . . ? N8 C31 C30 121.1(7) . . ? N8 C31 H31A 119.5 . . ? C30 C31 H31A 119.5 . . ? N8 C32 C28 122.7(7) . . ? N8 C32 H32A 118.6 . . ? C28 C32 H32A 118.6 . . ? O12 C33 O11 125.8(8) . . ? O12 C33 C34 118.0(6) . . ? O11 C33 C34 116.2(7) . . ? C35 C34 C40 117.8(7) . . ? C35 C34 C33 120.8(6) . . ? C40 C34 C33 121.4(6) . . ? C34 C35 C37 119.9(7) . . ? C34 C35 C36 123.1(7) . . ? C37 C35 C36 117.0(7) . . ? O13 C36 O14 122.1(7) . . ? O13 C36 C35 121.4(7) . . ? O14 C36 C35 116.5(7) . . ? C38 C37 C35 121.6(7) . . ? C38 C37 H37A 119.2 . . ? C35 C37 H37A 119.2 . . ? C37 C38 C39 119.3(8) . . ? C37 C38 H38A 120.3 . . ? C39 C38 H38A 120.3 . . ? C38 C39 C40 119.8(7) . . ? C38 C39 H39A 120.1 . . ? C40 C39 H39A 120.1 . . ? C39 C40 C34 121.6(6) . . ? C39 C40 C41 118.6(7) . . ? C34 C40 C41 119.8(7) . . ? O16 C41 O15 123.5(8) . . ? O16 C41 C40 122.3(8) . . ? O15 C41 C40 114.2(7) . . ? O6 C42 O5 122.5(8) . . ? O6 C42 C43 121.2(7) . . ? O5 C42 C43 116.3(7) . . ? C44 C43 C49 118.8(7) . . ? C44 C43 C42 117.2(7) . . ? C49 C43 C42 124.0(7) . . ? C45 C44 C43 121.0(7) . . ? C45 C44 H44A 119.5 . . ? C43 C44 H44A 119.5 . . ? C46 C45 C44 119.9(8) . . ? C46 C45 H45A 120.0 . . ? C44 C45 H45A 120.0 . . ? C45 C46 C47 120.2(7) . . ? C45 C46 H46A 119.9 . . ? C47 C46 H46A 119.9 . . ? C49 C47 C46 121.0(7) . . ? C49 C47 C48 120.6(7) . . ? C46 C47 C48 118.4(7) . . ? O9 C48 O10 123.5(8) . . ? O9 C48 C47 122.4(7) . . ? O10 C48 C47 114.1(7) . . ? C47 C49 C43 119.0(7) . . ? C47 C49 C50 119.9(7) . . ? C43 C49 C50 121.1(7) . . ? O8 C50 O7 123.0(7) . . ? O8 C50 C49 117.4(7) . . ? O7 C50 C49 119.6(7) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.619 _refine_diff_density_min -0.717 _refine_diff_density_rms 0.118 _database_code_depnum_ccdc_archive 'CCDC 949407' ####################################################################### # # 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_7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 Cd N2 O9' _chemical_formula_weight 505.73 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 P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 11.52730(10) _cell_length_b 9.04880(10) _cell_length_c 18.0697(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.7070(10) _cell_angle_gamma 90.00 _cell_volume 1867.79(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9902 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 28.37 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.798 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1012 _exptl_absorpt_coefficient_mu 1.225 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6457 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17040 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.37 _reflns_number_total 4663 _reflns_number_gt 4033 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2010)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0307P)^2^+1.0869P] 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 4663 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0634 _refine_ls_wR_factor_gt 0.0602 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 Cd Cd 1.333790(12) 1.343790(14) -0.095020(7) 0.02453(4) Uani 1 1 d . . . O11 O 1.0944(6) 1.1651(6) 0.1055(4) 0.0509(15) Uiso 0.40 1 d P B . O12 O 1.0930(4) 1.0975(6) 0.0928(3) 0.0535(13) Uani 0.40 1 d P B . O13 O 1.0924(7) 1.2436(14) 0.1168(5) 0.054(3) Uani 0.20 1 d P B . O2 O 1.35427(13) 1.38186(15) 0.03182(7) 0.0310(3) Uani 1 1 d . . . O3 O 1.35975(14) 1.14641(14) 0.00217(8) 0.0348(3) Uani 1 1 d . . . O4 O 1.34975(18) 0.77620(16) 0.21015(8) 0.0512(5) Uani 1 1 d . . . O5 O 1.34054(16) 0.85912(14) 0.32538(8) 0.0383(4) Uani 1 1 d . . . O6 O 1.34744(14) 1.38430(15) 0.38005(7) 0.0354(3) Uani 1 1 d . . . O7 O 1.31762(14) 1.54271(14) 0.28796(7) 0.0363(3) Uani 1 1 d . . . N1 N 1.13100(17) 1.3395(2) -0.09550(11) 0.0447(5) Uani 1 1 d . B . N2 N 0.92792(17) 1.1996(3) 0.02856(12) 0.0596(6) Uani 1 1 d . . . H2A H 0.8533 1.1880 0.0241 0.071 Uiso 1 1 calc R . . C1 C 1.0585(3) 1.4186(5) -0.14195(19) 0.0946(13) Uani 1 1 d . . . H1A H 1.0839 1.4529 -0.1855 0.113 Uiso 1 1 calc R A 1 C2 C 0.9414(4) 1.4547(7) -0.1285(3) 0.0499(13) Uani 0.50 1 d P B 1 H2C H 0.8980 1.5278 -0.1558 0.060 Uiso 0.50 1 calc PR B 1 C3 C 0.8970(8) 1.3774(10) -0.0742(6) 0.063(2) Uani 0.50 1 d P B 1 H3A H 0.8204 1.3926 -0.0651 0.076 Uiso 0.50 1 calc PR B 1 C2' C 0.9397(8) 1.3725(10) -0.1494(6) 0.098(3) Uiso 0.50 1 d P B 2 H2D H 0.8920 1.3797 -0.1950 0.117 Uiso 0.50 1 calc PR B 2 C3' C 0.8971(7) 1.3177(12) -0.0882(5) 0.086(4) Uani 0.50 1 d P B 2 H3C H 0.8168 1.3134 -0.0868 0.104 Uiso 0.50 1 calc PR B 2 C4 C 0.9716(2) 1.2703(4) -0.03057(13) 0.0521(7) Uani 1 1 d . . . C5 C 1.0878(2) 1.2678(3) -0.04071(13) 0.0491(6) Uani 1 1 d . B . H5A H 1.1393 1.2129 -0.0074 0.059 Uiso 1 1 calc R . . C6 C 0.9893(3) 1.1474(5) 0.09182(18) 0.0815(12) Uani 1 1 d . . . C7 C 0.9149(3) 1.0904(6) 0.14873(18) 0.0943(13) Uani 1 1 d . B . H7A H 0.8650 1.1704 0.1613 0.113 Uiso 0.50 1 calc PR C 1 H7B H 0.8643 1.0132 0.1254 0.113 Uiso 0.50 1 calc PR C 1 C8 C 0.9788(5) 1.0311(7) 0.2189(3) 0.0610(15) Uani 0.50 1 d P . 1 H8A H 0.9317 0.9429 0.2213 0.073 Uiso 0.50 1 calc PR . 1 H8B H 1.0468 0.9958 0.1979 0.073 Uiso 0.50 1 calc PR . 1 C8' C 0.9767(7) 1.1598(8) 0.2362(4) 0.083(3) Uani 0.50 1 d P . 2 H8C H 0.9695 1.2650 0.2264 0.099 Uiso 0.50 1 calc PR . 2 H8D H 0.9139 1.1381 0.2653 0.099 Uiso 0.50 1 calc PR . 2 C9 C 1.35894(16) 1.2467(2) 0.05003(9) 0.0240(4) Uani 1 1 d . . . C10 C 1.35805(15) 1.2093(2) 0.13068(9) 0.0214(4) Uani 1 1 d . . . C11 C 1.35659(16) 1.0629(2) 0.15465(9) 0.0239(4) Uani 1 1 d . . . H11A H 1.3588 0.9861 0.1207 0.029 Uiso 1 1 calc R . . C12 C 1.35187(15) 1.03259(19) 0.22958(9) 0.0217(3) Uani 1 1 d . . . C13 C 1.34990(16) 1.14681(18) 0.28038(9) 0.0221(4) Uani 1 1 d . . . H13A H 1.3500 1.1255 0.3307 0.026 Uiso 1 1 calc R . . C14 C 1.34772(16) 1.29177(19) 0.25699(9) 0.0212(3) Uani 1 1 d . . . C15 C 1.35141(16) 1.32289(19) 0.18179(10) 0.0225(4) Uani 1 1 d . . . H15A H 1.3494 1.4206 0.1656 0.027 Uiso 1 1 calc R . . C16 C 1.34701(17) 0.8802(2) 0.25938(10) 0.0255(4) Uani 1 1 d . . . C17 C 1.33827(16) 1.4118(2) 0.31207(10) 0.0252(4) Uani 1 1 d . . . O8 O 1.53274(14) 1.36605(18) -0.08896(9) 0.0364(4) Uani 1 1 d . . . O9 O 1.33003(15) 1.16758(18) 0.49085(9) 0.0383(4) Uani 1 1 d . . . H4C H 1.347(2) 0.698(3) 0.2286(15) 0.045(7) Uiso 1 1 d . . . H5C H 1.571(2) 1.305(3) -0.0667(16) 0.053(9) Uiso 1 1 d . . . H5D H 1.559(2) 1.435(3) -0.0728(16) 0.057(9) Uiso 1 1 d . . . H9C H 1.349(2) 1.208(3) 0.4604(16) 0.051(8) Uiso 1 1 d . . . H9D H 1.352(2) 1.085(3) 0.4899(16) 0.061 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 Cd 0.04099(8) 0.01997(7) 0.01341(6) 0.00106(5) 0.00654(5) -0.00169(5) O12 0.036(2) 0.064(3) 0.061(3) 0.018(3) 0.0055(19) 0.001(2) O13 0.023(4) 0.099(9) 0.039(5) 0.001(5) -0.002(3) -0.013(5) O2 0.0551(9) 0.0220(6) 0.0163(6) 0.0040(5) 0.0062(6) -0.0038(6) O3 0.0636(9) 0.0262(7) 0.0160(6) -0.0021(5) 0.0105(6) -0.0007(6) O4 0.1188(15) 0.0155(7) 0.0233(7) 0.0011(6) 0.0240(8) 0.0016(8) O5 0.0780(11) 0.0192(7) 0.0198(7) 0.0025(5) 0.0144(7) 0.0027(7) O6 0.0692(10) 0.0231(7) 0.0151(6) -0.0011(5) 0.0099(6) -0.0012(7) O7 0.0728(10) 0.0153(6) 0.0218(7) -0.0001(5) 0.0104(6) 0.0038(6) N1 0.0394(10) 0.0623(14) 0.0328(10) 0.0084(9) 0.0065(8) -0.0021(9) N2 0.0318(10) 0.1046(18) 0.0427(12) 0.0182(12) 0.0065(8) -0.0068(11) C1 0.0471(16) 0.171(4) 0.065(2) 0.062(2) 0.0054(14) 0.001(2) C2 0.036(2) 0.063(3) 0.050(3) 0.023(3) 0.000(2) 0.012(2) C3 0.041(3) 0.078(5) 0.069(5) 0.007(4) 0.006(3) 0.014(3) C3' 0.032(3) 0.163(11) 0.065(5) 0.053(6) 0.006(3) 0.002(5) C4 0.0361(12) 0.084(2) 0.0363(13) 0.0064(13) 0.0042(9) -0.0069(13) C5 0.0380(12) 0.0712(17) 0.0388(13) 0.0114(12) 0.0075(9) 0.0005(12) C6 0.0411(14) 0.156(4) 0.0474(17) 0.0322(19) 0.0060(12) -0.0043(18) C7 0.071(2) 0.163(4) 0.0503(18) 0.032(2) 0.0138(15) -0.021(2) C8 0.066(3) 0.074(4) 0.043(3) 0.007(3) 0.010(2) -0.016(3) C8' 0.077(6) 0.119(6) 0.048(5) 0.025(4) -0.002(4) -0.023(4) C9 0.0335(9) 0.0252(9) 0.0140(8) 0.0009(7) 0.0053(7) -0.0024(7) C10 0.0296(9) 0.0204(8) 0.0145(8) 0.0020(6) 0.0045(6) -0.0010(7) C11 0.0365(10) 0.0200(8) 0.0160(8) -0.0011(6) 0.0063(7) 0.0008(7) C12 0.0320(9) 0.0171(8) 0.0166(8) 0.0008(6) 0.0055(6) 0.0015(7) C13 0.0321(9) 0.0211(9) 0.0134(8) 0.0013(6) 0.0044(6) 0.0003(7) C14 0.0310(9) 0.0176(8) 0.0156(8) -0.0013(6) 0.0048(6) -0.0015(7) C15 0.0335(9) 0.0177(8) 0.0166(8) 0.0018(6) 0.0044(7) -0.0004(7) C16 0.0394(10) 0.0199(9) 0.0180(8) 0.0009(7) 0.0071(7) 0.0021(7) C17 0.0361(10) 0.0217(9) 0.0188(8) -0.0023(7) 0.0071(7) -0.0027(8) O8 0.0430(8) 0.0281(8) 0.0386(9) -0.0034(7) 0.0073(7) -0.0020(7) O9 0.0502(9) 0.0320(8) 0.0340(9) 0.0053(7) 0.0104(7) 0.0029(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 Cd O8 2.2901(16) . ? Cd O2 2.2983(13) . ? Cd O7 2.3356(13) 4_585 ? Cd N1 2.3368(19) . ? Cd O5 2.3401(13) 4_575 ? Cd O3 2.4946(14) . ? Cd O6 2.5101(14) 4_585 ? Cd C9 2.7426(17) . ? O11 O12 0.654(7) . ? O11 O13 0.740(12) . ? O11 C6 1.215(7) . ? O12 C6 1.277(6) . ? O12 O13 1.392(13) . ? O13 C6 1.493(10) . ? O2 C9 1.266(2) . ? O3 C9 1.254(2) . ? O4 C16 1.298(2) . ? O4 H4C 0.78(3) . ? O5 C16 1.220(2) . ? O5 Cd 2.3401(13) 4_576 ? O6 C17 1.244(2) . ? O6 Cd 2.5101(14) 4_586 ? O7 C17 1.273(2) . ? O7 Cd 2.3356(13) 4_586 ? N1 C1 1.315(4) . ? N1 C5 1.334(3) . ? N2 C6 1.346(4) . ? N2 C4 1.396(3) . ? N2 H2A 0.8600 . ? C1 C2' 1.421(10) . ? C1 C2 1.441(6) . ? C1 H1A 0.9300 . ? C2 C3 1.359(12) . ? C2 H2C 0.9300 . ? C3 C4 1.455(10) . ? C3 H3A 0.9300 . ? C2' C3' 1.362(13) . ? C2' H2D 0.9300 . ? C3' C4 1.329(9) . ? C3' H3C 0.9300 . ? C4 C5 1.377(3) . ? C5 H5A 0.9300 . ? C6 C7 1.515(4) . ? C7 C8 1.478(6) . ? C7 C8' 1.759(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C8 1.166(10) 2_755 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8' C8' 0.683(12) 2_755 ? C8' H8C 0.9700 . ? C8' H8D 0.9700 . ? C9 C10 1.497(2) . ? C10 C15 1.391(2) . ? C10 C11 1.394(2) . ? C11 C12 1.390(2) . ? C11 H11A 0.9300 . ? C12 C13 1.385(2) . ? C12 C16 1.484(2) . ? C13 C14 1.377(2) . ? C13 H13A 0.9300 . ? C14 C15 1.394(2) . ? C14 C17 1.487(2) . ? C15 H15A 0.9300 . ? O8 H5C 0.78(3) . ? O8 H5D 0.74(3) . ? O9 H9C 0.72(3) . ? O9 H9D 0.79(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O8 Cd O2 88.33(6) . . ? O8 Cd O7 87.85(6) . 4_585 ? O2 Cd O7 145.28(5) . 4_585 ? O8 Cd N1 175.20(7) . . ? O2 Cd N1 88.58(6) . . ? O7 Cd N1 92.62(6) 4_585 . ? O8 Cd O5 89.01(6) . 4_575 ? O2 Cd O5 136.31(5) . 4_575 ? O7 Cd O5 78.10(5) 4_585 4_575 ? N1 Cd O5 95.75(7) . 4_575 ? O8 Cd O3 90.26(6) . . ? O2 Cd O3 54.46(4) . . ? O7 Cd O3 160.00(5) 4_585 . ? N1 Cd O3 90.92(6) . . ? O5 Cd O3 81.96(5) 4_575 . ? O8 Cd O6 80.55(6) . 4_585 ? O2 Cd O6 91.81(4) . 4_585 ? O7 Cd O6 53.54(4) 4_585 4_585 ? N1 Cd O6 95.88(6) . 4_585 ? O5 Cd O6 130.60(4) 4_575 4_585 ? O3 Cd O6 145.46(4) . 4_585 ? O8 Cd C9 90.32(6) . . ? O2 Cd C9 27.31(5) . . ? O7 Cd C9 172.50(5) 4_585 . ? N1 Cd C9 88.61(6) . . ? O5 Cd C9 109.15(5) 4_575 . ? O3 Cd C9 27.19(5) . . ? O6 Cd C9 118.97(5) 4_585 . ? O12 O11 O13 174.7(17) . . ? O12 O11 C6 80.1(8) . . ? O13 O11 C6 96.6(10) . . ? O11 O12 C6 69.6(8) . . ? O11 O12 O13 2.8(9) . . ? C6 O12 O13 67.9(4) . . ? O11 O13 O12 2.5(8) . . ? O11 O13 C6 53.9(8) . . ? O12 O13 C6 52.4(4) . . ? C9 O2 Cd 96.29(11) . . ? C9 O3 Cd 87.48(10) . . ? C16 O4 H4C 110.8(19) . . ? C16 O5 Cd 137.29(12) . 4_576 ? C17 O6 Cd 88.95(11) . 4_586 ? C17 O7 Cd 96.35(11) . 4_586 ? C1 N1 C5 118.0(2) . . ? C1 N1 Cd 122.91(18) . . ? C5 N1 Cd 118.54(15) . . ? C6 N2 C4 127.5(2) . . ? C6 N2 H2A 116.3 . . ? C4 N2 H2A 116.3 . . ? N1 C1 C2' 115.0(5) . . ? N1 C1 C2 123.1(3) . . ? C2' C1 C2 33.8(4) . . ? N1 C1 H1A 118.5 . . ? C2' C1 H1A 115.3 . . ? C2 C1 H1A 118.5 . . ? C3 C2 C1 117.2(5) . . ? C3 C2 H2C 121.4 . . ? C1 C2 H2C 121.4 . . ? C2 C3 C4 118.8(7) . . ? C2 C3 H3A 120.6 . . ? C4 C3 H3A 120.6 . . ? C3' C2' C1 118.6(8) . . ? C3' C2' H2D 120.7 . . ? C1 C2' H2D 120.7 . . ? C4 C3' C2' 119.2(8) . . ? C4 C3' H3C 120.4 . . ? C2' C3' H3C 120.4 . . ? C3' C4 C5 116.1(4) . . ? C3' C4 N2 119.1(4) . . ? C5 C4 N2 123.5(2) . . ? C3' C4 C3 24.2(6) . . ? C5 C4 C3 117.0(5) . . ? N2 C4 C3 118.2(4) . . ? N1 C5 C4 123.9(2) . . ? N1 C5 H5A 118.1 . . ? C4 C5 H5A 118.1 . . ? O11 C6 O12 30.3(3) . . ? O11 C6 N2 121.5(4) . . ? O12 C6 N2 121.4(3) . . ? O11 C6 O13 29.5(4) . . ? O12 C6 O13 59.7(5) . . ? N2 C6 O13 111.0(5) . . ? O11 C6 C7 123.1(4) . . ? O12 C6 C7 119.0(4) . . ? N2 C6 C7 114.5(3) . . ? O13 C6 C7 119.6(4) . . ? C8 C7 C6 116.3(3) . . ? C8 C7 C8' 42.7(3) . . ? C6 C7 C8' 106.9(4) . . ? C8 C7 H7A 108.2 . . ? C6 C7 H7A 108.2 . . ? C8' C7 H7A 72.8 . . ? C8 C7 H7B 108.2 . . ? C6 C7 H7B 108.2 . . ? C8' C7 H7B 142.7 . . ? H7A C7 H7B 107.4 . . ? C8 C8 C7 157.5(4) 2_755 . ? C8 C8 H8A 96.9 2_755 . ? C7 C8 H8A 96.9 . . ? C8 C8 H8B 96.9 2_755 . ? C7 C8 H8B 96.9 . . ? H8A C8 H8B 103.5 . . ? C8' C8' C7 147.3(14) 2_755 . ? C8' C8' H8C 100.0 2_755 . ? C7 C8' H8C 100.0 . . ? C8' C8' H8D 100.0 2_755 . ? C7 C8' H8D 100.0 . . ? H8C C8' H8D 104.2 . . ? O3 C9 O2 121.58(16) . . ? O3 C9 C10 120.61(16) . . ? O2 C9 C10 117.75(16) . . ? O3 C9 Cd 65.32(9) . . ? O2 C9 Cd 56.41(9) . . ? C10 C9 Cd 171.41(13) . . ? C15 C10 C11 119.45(15) . . ? C15 C10 C9 119.18(16) . . ? C11 C10 C9 121.25(16) . . ? C12 C11 C10 119.61(16) . . ? C12 C11 H11A 120.2 . . ? C10 C11 H11A 120.2 . . ? C13 C12 C11 120.31(16) . . ? C13 C12 C16 116.64(15) . . ? C11 C12 C16 123.05(16) . . ? C14 C13 C12 120.58(16) . . ? C14 C13 H13A 119.7 . . ? C12 C13 H13A 119.7 . . ? C13 C14 C15 119.33(16) . . ? C13 C14 C17 119.36(16) . . ? C15 C14 C17 121.28(16) . . ? C10 C15 C14 120.64(16) . . ? C10 C15 H15A 119.7 . . ? C14 C15 H15A 119.7 . . ? O5 C16 O4 124.56(18) . . ? O5 C16 C12 120.66(16) . . ? O4 C16 C12 114.79(16) . . ? O6 C17 O7 120.77(17) . . ? O6 C17 C14 120.68(17) . . ? O7 C17 C14 118.53(16) . . ? Cd O8 H5C 116(2) . . ? Cd O8 H5D 117(2) . . ? H5C O8 H5D 103(3) . . ? H9C O9 H9D 109(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.641 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 949408' ####################################################################### # # 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_8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H20 N2 O11 Zn1.50' _chemical_formula_weight 526.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.0834(9) _cell_length_b 20.891(2) _cell_length_c 16.210(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.148(12) _cell_angle_gamma 90.00 _cell_volume 2054.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.62 _cell_measurement_theta_max 12.43 _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 1.702 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1076 _exptl_absorpt_coefficient_mu 1.829 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7693 _exptl_absorpt_correction_T_max 0.8872 _exptl_absorpt_process_details '(XSCANS; Siemens, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 4924 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0646 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3594 _reflns_number_gt 2648 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Siemens, 1995)' _computing_cell_refinement 'XSCANS (Siemens, 1995)' _computing_data_reduction 'SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0522P)^2^+0.8548P] 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 3594 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.0950 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.10219(7) 0.23416(2) 0.91652(3) 0.02585(16) Uani 1 1 d . . . Zn2 Zn 0.0000 0.0000 1.0000 0.0409(2) Uani 1 2 d S . . O1 O -0.6838(6) 0.48135(19) 0.8205(3) 0.0720(12) Uani 1 1 d . . . O2 O -0.0097(4) 0.14700(13) 0.93496(16) 0.0295(7) Uani 1 1 d . . . O3 O -0.1416(5) 0.05133(14) 0.89904(17) 0.0398(8) Uani 1 1 d . . . O4 O -0.6834(5) 0.22364(14) 0.83243(17) 0.0341(7) Uani 1 1 d . . . O5 O -0.5058(5) 0.15408(16) 0.91643(17) 0.0425(8) Uani 1 1 d . . . O6 O -0.2017(6) 0.20615(18) 0.50325(17) 0.0495(9) Uani 1 1 d . . . O7 O -0.5102(8) 0.24137(19) 0.5419(2) 0.0683(12) Uani 1 1 d . . . O8 O 0.3045(6) 0.05250(17) 1.0095(2) 0.0633(11) Uani 1 1 d . . . H8D H 0.4031 0.0659 1.0430 0.076 Uiso 1 1 d R . . H8C H 0.3615 0.0786 0.9673 0.076 Uiso 1 1 d R . . O9 O -0.1296(7) 0.05785(17) 1.0873(2) 0.0624(10) Uani 1 1 d . . . N1 N -0.1030(5) 0.29746(16) 0.85181(19) 0.0277(8) Uani 1 1 d . . . N2 N -0.5857(6) 0.39129(19) 0.8911(2) 0.0439(10) Uani 1 1 d . . . H2A H -0.6189 0.3680 0.9321 0.053 Uiso 1 1 calc R . . C1 C -0.0611(7) 0.3162(2) 0.7751(3) 0.0369(11) Uani 1 1 d . . . H1A H 0.0570 0.2980 0.7502 0.044 Uiso 1 1 calc R . . C2 C -0.1882(8) 0.3613(2) 0.7328(3) 0.0454(12) Uani 1 1 d . . . H2B H -0.1545 0.3738 0.6801 0.054 Uiso 1 1 calc R . . C3 C -0.3658(8) 0.3883(2) 0.7681(3) 0.0457(12) Uani 1 1 d . . . H3A H -0.4533 0.4188 0.7398 0.055 Uiso 1 1 calc R . . C4 C -0.4104(7) 0.3687(2) 0.8471(3) 0.0335(10) Uani 1 1 d . . . C5 C -0.2750(6) 0.32303(19) 0.8862(2) 0.0281(9) Uani 1 1 d . . . H5A H -0.3054 0.3096 0.9389 0.034 Uiso 1 1 calc R . . C6 C -0.7092(8) 0.4447(2) 0.8777(3) 0.0470(12) Uani 1 1 d . . . C7 C -0.8797(9) 0.4547(3) 0.9403(4) 0.0603(15) Uani 1 1 d . . . C8 C -1.0361(17) 0.5039(6) 0.9199(7) 0.064(3) Uani 0.50 1 d P . . C8' C -0.7937(15) 0.4848(6) 1.0121(7) 0.053(3) Uani 0.50 1 d P . . C9 C -0.1112(6) 0.10949(19) 0.8848(2) 0.0248(9) Uani 1 1 d . . . C10 C -0.1855(6) 0.13423(18) 0.7996(2) 0.0234(9) Uani 1 1 d . . . C11 C -0.3799(6) 0.16943(18) 0.7835(2) 0.0210(8) Uani 1 1 d . . . C12 C -0.5319(6) 0.1825(2) 0.8496(2) 0.0272(9) Uani 1 1 d . . . C13 C -0.4262(7) 0.19342(19) 0.7037(2) 0.0261(9) Uani 1 1 d . . . H13A H -0.5550 0.2167 0.6920 0.031 Uiso 1 1 calc R . . C14 C -0.2840(7) 0.18334(19) 0.6412(2) 0.0267(9) Uani 1 1 d . . . C15 C -0.3359(8) 0.2121(2) 0.5582(2) 0.0360(11) Uani 1 1 d . . . C16 C -0.0927(7) 0.1482(2) 0.6591(2) 0.0365(11) Uani 1 1 d . . . H16A H 0.0039 0.1413 0.6180 0.044 Uiso 1 1 calc R . . C17 C -0.0452(7) 0.1235(2) 0.7368(2) 0.0337(10) Uani 1 1 d . . . H17A H 0.0820 0.0993 0.7477 0.040 Uiso 1 1 calc R . . O10 O -0.460(3) 0.0016(10) 1.1666(14) 0.065(5) Uani 0.50 1 d P A 1 O10' O -0.406(3) -0.0165(10) 1.1799(13) 0.059(4) Uani 0.50 1 d P B 2 O11 O -0.3424(6) 0.17545(17) 1.0850(2) 0.0573(9) Uani 1 1 d . . . H6C H -0.4199 0.1727 1.0415 0.086 Uiso 1 1 d R . . H6D H -0.2470 0.1984 1.0813 0.086 Uiso 1 1 d R . . H9C H -0.2594 0.0390 1.0945 0.086 Uiso 1 1 d R . . H9D H -0.1890 0.0933 1.0762 0.086 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0248(3) 0.0312(3) 0.0215(2) -0.0036(2) 0.00138(18) 0.0030(2) Zn2 0.0422(5) 0.0398(4) 0.0383(4) 0.0149(3) -0.0129(3) -0.0024(4) O1 0.066(3) 0.061(3) 0.091(3) 0.023(2) 0.026(2) 0.031(2) O2 0.0318(16) 0.0338(16) 0.0223(14) 0.0032(12) -0.0038(12) -0.0004(13) O3 0.0524(19) 0.0299(17) 0.0345(16) 0.0103(14) -0.0142(14) -0.0020(15) O4 0.0312(16) 0.0416(18) 0.0307(15) 0.0004(13) 0.0095(13) 0.0121(15) O5 0.0320(17) 0.071(2) 0.0255(16) 0.0170(15) 0.0071(13) 0.0097(16) O6 0.057(2) 0.073(2) 0.0196(15) 0.0051(15) 0.0088(15) -0.0167(19) O7 0.104(3) 0.074(3) 0.0255(17) 0.0058(17) -0.0024(19) 0.051(3) O8 0.059(2) 0.065(2) 0.060(2) 0.0256(19) -0.0306(18) -0.025(2) O9 0.081(3) 0.047(2) 0.058(2) 0.0047(18) -0.012(2) 0.006(2) N1 0.0259(18) 0.0324(19) 0.0251(17) -0.0022(15) 0.0034(15) 0.0034(16) N2 0.035(2) 0.048(2) 0.050(2) 0.0049(19) 0.0109(19) 0.0102(19) C1 0.035(2) 0.047(3) 0.029(2) 0.001(2) 0.0100(19) 0.006(2) C2 0.052(3) 0.058(3) 0.027(2) 0.007(2) 0.011(2) 0.017(3) C3 0.049(3) 0.045(3) 0.043(3) 0.010(2) 0.003(2) 0.018(2) C4 0.023(2) 0.038(3) 0.039(3) 0.000(2) 0.0042(19) 0.005(2) C5 0.025(2) 0.033(2) 0.026(2) -0.0004(18) 0.0021(17) -0.0019(19) C6 0.031(3) 0.041(3) 0.069(3) 0.003(3) 0.005(2) 0.009(2) C7 0.046(3) 0.057(4) 0.080(4) -0.004(3) 0.020(3) 0.019(3) C8 0.043(6) 0.089(9) 0.060(7) 0.006(6) 0.012(5) 0.034(6) C8' 0.025(5) 0.073(8) 0.062(7) -0.016(6) 0.002(5) 0.008(5) C9 0.023(2) 0.029(2) 0.023(2) 0.0059(17) 0.0021(16) 0.0050(18) C10 0.025(2) 0.024(2) 0.0202(19) 0.0019(16) -0.0025(16) 0.0021(17) C11 0.022(2) 0.025(2) 0.0153(18) 0.0008(15) 0.0012(15) 0.0003(17) C12 0.024(2) 0.035(2) 0.022(2) 0.0004(18) 0.0001(17) -0.004(2) C13 0.024(2) 0.031(2) 0.023(2) 0.0019(17) -0.0037(16) 0.0038(18) C14 0.033(2) 0.030(2) 0.0164(19) -0.0004(16) 0.0018(17) -0.0005(19) C15 0.058(3) 0.030(2) 0.019(2) -0.0028(18) 0.001(2) -0.006(2) C16 0.035(3) 0.051(3) 0.024(2) 0.000(2) 0.0083(19) 0.007(2) C17 0.030(2) 0.041(3) 0.030(2) 0.002(2) 0.0021(18) 0.011(2) O10 0.061(10) 0.077(12) 0.054(7) 0.000(7) -0.024(6) 0.001(7) O10' 0.041(8) 0.068(10) 0.065(9) 0.011(6) -0.001(7) -0.005(7) O11 0.065(2) 0.063(2) 0.045(2) 0.0050(18) 0.0103(17) -0.005(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 Zn1 O4 1.966(3) 1_655 ? Zn1 O2 1.974(3) . ? Zn1 N1 2.054(3) . ? Zn1 O6 2.171(3) 4_666 ? Zn1 O7 2.249(4) 4_666 ? Zn1 C15 2.560(4) 4_666 ? Zn2 O9 2.061(4) 3_557 ? Zn2 O9 2.061(4) . ? Zn2 O3 2.090(3) 3_557 ? Zn2 O3 2.090(3) . ? Zn2 O8 2.149(3) 3_557 ? Zn2 O8 2.149(3) . ? O1 C6 1.221(6) . ? O2 C9 1.258(5) . ? O3 C9 1.253(5) . ? O4 C12 1.276(5) . ? O4 Zn1 1.966(3) 1_455 ? O5 C12 1.236(5) . ? O6 C15 1.257(5) . ? O6 Zn1 2.171(3) 4_565 ? O7 C15 1.236(6) . ? O7 Zn1 2.249(4) 4_565 ? O8 H8D 0.8287 . ? O8 H8C 0.9594 . ? O9 H9C 0.8969 . ? O9 H9D 0.8389 . ? N1 C5 1.333(5) . ? N1 C1 1.345(5) . ? N2 C6 1.354(6) . ? N2 C4 1.407(5) . ? N2 H2A 0.8600 . ? C1 C2 1.372(6) . ? C1 H1A 0.9300 . ? C2 C3 1.379(6) . ? C2 H2B 0.9300 . ? C3 C4 1.389(6) . ? C3 H3A 0.9300 . ? C4 C5 1.385(6) . ? C5 H5A 0.9300 . ? C6 C7 1.518(7) . ? C7 C8' 1.390(11) . ? C7 C8 1.423(12) . ? C8 C8' 1.583(14) 3_367 ? C8' C8 1.583(14) 3_367 ? C9 C10 1.513(5) . ? C10 C17 1.393(5) . ? C10 C11 1.401(5) . ? C11 C13 1.396(5) . ? C11 C12 1.490(5) . ? C13 C14 1.395(5) . ? C13 H13A 0.9300 . ? C14 C16 1.389(6) . ? C14 C15 1.487(5) . ? C15 Zn1 2.560(4) 4_565 ? C16 C17 1.373(6) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? O11 H6C 0.8207 . ? O11 H6D 0.7588 . ? 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 Zn1 O2 104.79(12) 1_655 . ? O4 Zn1 N1 97.30(12) 1_655 . ? O2 Zn1 N1 117.88(13) . . ? O4 Zn1 O6 98.76(12) 1_655 4_666 ? O2 Zn1 O6 127.66(12) . 4_666 ? N1 Zn1 O6 104.25(13) . 4_666 ? O4 Zn1 O7 155.79(14) 1_655 4_666 ? O2 Zn1 O7 86.68(12) . 4_666 ? N1 Zn1 O7 95.85(15) . 4_666 ? O6 Zn1 O7 58.19(13) 4_666 4_666 ? O4 Zn1 C15 127.52(15) 1_655 4_666 ? O2 Zn1 C15 107.39(13) . 4_666 ? N1 Zn1 C15 102.72(13) . 4_666 ? O6 Zn1 C15 29.36(14) 4_666 4_666 ? O7 Zn1 C15 28.88(14) 4_666 4_666 ? O9 Zn2 O9 179.999(2) 3_557 . ? O9 Zn2 O3 94.62(13) 3_557 3_557 ? O9 Zn2 O3 85.38(13) . 3_557 ? O9 Zn2 O3 85.38(13) 3_557 . ? O9 Zn2 O3 94.62(13) . . ? O3 Zn2 O3 179.999(1) 3_557 . ? O9 Zn2 O8 91.28(16) 3_557 3_557 ? O9 Zn2 O8 88.72(16) . 3_557 ? O3 Zn2 O8 95.65(12) 3_557 3_557 ? O3 Zn2 O8 84.35(12) . 3_557 ? O9 Zn2 O8 88.72(16) 3_557 . ? O9 Zn2 O8 91.28(16) . . ? O3 Zn2 O8 84.35(12) 3_557 . ? O3 Zn2 O8 95.65(12) . . ? O8 Zn2 O8 180.0 3_557 . ? C9 O2 Zn1 129.4(2) . . ? C9 O3 Zn2 125.7(3) . . ? C12 O4 Zn1 115.4(2) . 1_455 ? C15 O6 Zn1 92.7(3) . 4_565 ? C15 O7 Zn1 89.6(3) . 4_565 ? Zn2 O8 H8D 143.1 . . ? Zn2 O8 H8C 126.4 . . ? H8D O8 H8C 89.6 . . ? Zn2 O9 H9C 102.4 . . ? Zn2 O9 H9D 123.4 . . ? H9C O9 H9D 92.7 . . ? C5 N1 C1 118.5(4) . . ? C5 N1 Zn1 120.7(3) . . ? C1 N1 Zn1 120.7(3) . . ? C6 N2 C4 128.8(4) . . ? C6 N2 H2A 115.6 . . ? C4 N2 H2A 115.6 . . ? N1 C1 C2 121.6(4) . . ? N1 C1 H1A 119.2 . . ? C2 C1 H1A 119.2 . . ? C1 C2 C3 120.2(4) . . ? C1 C2 H2B 119.9 . . ? C3 C2 H2B 119.9 . . ? C2 C3 C4 118.3(4) . . ? C2 C3 H3A 120.8 . . ? C4 C3 H3A 120.8 . . ? C5 C4 C3 118.4(4) . . ? C5 C4 N2 116.5(4) . . ? C3 C4 N2 125.1(4) . . ? N1 C5 C4 122.9(4) . . ? N1 C5 H5A 118.6 . . ? C4 C5 H5A 118.6 . . ? O1 C6 N2 122.7(5) . . ? O1 C6 C7 123.5(4) . . ? N2 C6 C7 113.9(5) . . ? C8' C7 C8 94.2(7) . . ? C8' C7 C6 112.9(6) . . ? C8 C7 C6 115.0(6) . . ? C7 C8 C8' 114.0(9) . 3_367 ? C7 C8' C8 115.1(8) . 3_367 ? O3 C9 O2 123.8(3) . . ? O3 C9 C10 117.5(4) . . ? O2 C9 C10 118.5(3) . . ? C17 C10 C11 120.1(3) . . ? C17 C10 C9 117.0(3) . . ? C11 C10 C9 122.8(3) . . ? C13 C11 C10 118.2(3) . . ? C13 C11 C12 120.4(3) . . ? C10 C11 C12 121.4(3) . . ? O5 C12 O4 124.0(4) . . ? O5 C12 C11 119.7(4) . . ? O4 C12 C11 116.3(3) . . ? C14 C13 C11 121.6(4) . . ? C14 C13 H13A 119.2 . . ? C11 C13 H13A 119.2 . . ? C16 C14 C13 118.9(3) . . ? C16 C14 C15 121.5(4) . . ? C13 C14 C15 119.7(4) . . ? O7 C15 O6 119.2(4) . . ? O7 C15 C14 121.0(4) . . ? O6 C15 C14 119.7(4) . . ? O7 C15 Zn1 61.5(2) . 4_565 ? O6 C15 Zn1 57.9(2) . 4_565 ? C14 C15 Zn1 175.8(3) . 4_565 ? C17 C16 C14 120.5(4) . . ? C17 C16 H16A 119.7 . . ? C14 C16 H16A 119.7 . . ? C16 C17 C10 120.7(4) . . ? C16 C17 H17A 119.7 . . ? C10 C17 H17A 119.7 . . ? H6C O11 H6D 111.9 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.442 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.090 #===END _database_code_depnum_ccdc_archive 'CCDC 949409'