# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 182 # 1. SUBMISSION DETAILS _publ_contact_author_name 'Xianhui Bu' _publ_contact_author_address ; Department of Chemistry and Biochemistry California State University, Long Beach 1250 Bellflower Boulevard, Long Beach, CA 90840 ; _publ_contact_author_email xbu@csulb.edu _publ_contact_author_fax ? loop_ _publ_author_name 'Xianhui Bu.' 'Jian Zhang.' _publ_requested_journal 'Chem. Commun' # Attachment '1.cif' data_1_a _database_code_depnum_ccdc_archive 'CCDC 671276' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 O4 Zn' _chemical_formula_weight 261.57 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' 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 Tetragonal _symmetry_space_group_name_H-M P4(3)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 13.2150(10) _cell_length_b 13.2150(10) _cell_length_c 12.84350(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2242.9(2) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 5895 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 27.15 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max .30 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 2.180 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 18480 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 30.18 _reflns_number_total 3328 _reflns_number_gt 2958 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0364P)^2^+0.2186P] 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 -0.011(14) _chemical_absolute_configuration rm _refine_ls_number_reflns 3328 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0683 _refine_ls_wR_factor_gt 0.0656 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.459982(17) -0.075342(18) -0.159824(18) 0.02268(7) Uani 1 1 d . . . O1 O 0.98302(11) 0.29773(11) -0.04269(12) 0.0274(3) Uani 1 1 d . . . O2 O 0.87647(14) 0.34543(14) 0.08244(14) 0.0416(4) Uani 1 1 d . . . O3 O 0.52801(12) 0.10049(13) 0.00234(15) 0.0406(4) Uani 1 1 d . . . O4 O 0.58405(13) -0.02128(14) -0.10234(15) 0.0470(5) Uani 1 1 d . . . C1 C 0.84952(18) 0.18652(18) 0.0027(2) 0.0337(5) Uani 1 1 d . . . C2 C 0.73152(17) 0.19553(17) 0.01231(17) 0.0279(4) Uani 1 1 d . . . C3 C 0.69935(19) 0.1039(2) -0.05220(19) 0.0362(6) Uani 1 1 d . . . C4 C 0.7722(2) 0.0716(2) -0.1132(2) 0.0532(8) Uani 1 1 d . . . H4A H 0.7660 0.0175 -0.1590 0.064 Uiso 1 1 calc R . . C5 C 0.8669(2) 0.1332(2) -0.0996(2) 0.0566(9) Uani 1 1 d . . . H5A H 0.8750 0.1814 -0.1560 0.068 Uiso 1 1 calc R . . H5B H 0.9263 0.0902 -0.0965 0.068 Uiso 1 1 calc R . . C6 C 0.8945(3) 0.1178(2) 0.0911(3) 0.0710(11) Uani 1 1 d . . . H6A H 0.9666 0.1139 0.0834 0.106 Uiso 1 1 calc R . . H6B H 0.8659 0.0512 0.0861 0.106 Uiso 1 1 calc R . . H6C H 0.8784 0.1465 0.1578 0.106 Uiso 1 1 calc R . . C7 C 0.6948(2) 0.1937(3) 0.1245(2) 0.0658(11) Uani 1 1 d . . . H7A H 0.6224 0.1992 0.1258 0.099 Uiso 1 1 calc R . . H7B H 0.7239 0.2495 0.1619 0.099 Uiso 1 1 calc R . . H7C H 0.7149 0.1313 0.1567 0.099 Uiso 1 1 calc R . . C8 C 0.6930(2) 0.2896(2) -0.0427(3) 0.0663(10) Uani 1 1 d . . . H8A H 0.6207 0.2934 -0.0359 0.099 Uiso 1 1 calc R . . H8B H 0.7107 0.2864 -0.1151 0.099 Uiso 1 1 calc R . . H8C H 0.7231 0.3485 -0.0119 0.099 Uiso 1 1 calc R . . C9 C 0.90658(16) 0.28488(17) 0.01356(16) 0.0256(4) Uani 1 1 d . . . C10 C 0.59678(18) 0.05852(19) -0.05054(18) 0.0335(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 Zn1 0.02084(13) 0.02060(13) 0.02658(11) -0.00494(10) 0.00584(9) -0.00434(9) O1 0.0220(8) 0.0225(7) 0.0378(8) 0.0023(6) 0.0030(6) -0.0027(6) O2 0.0409(10) 0.0421(10) 0.0418(9) -0.0207(8) 0.0103(8) -0.0184(8) O3 0.0232(9) 0.0335(9) 0.0651(11) -0.0024(8) 0.0050(8) -0.0069(7) O4 0.0320(9) 0.0451(11) 0.0639(12) -0.0194(9) 0.0007(9) -0.0155(8) C1 0.0277(12) 0.0321(13) 0.0412(13) -0.0127(10) 0.0084(10) -0.0114(10) C2 0.0265(11) 0.0274(12) 0.0299(11) -0.0062(9) 0.0035(9) -0.0100(9) C3 0.0305(13) 0.0400(14) 0.0383(12) -0.0143(10) 0.0052(10) -0.0142(11) C4 0.0403(15) 0.0576(18) 0.0615(18) -0.0392(15) 0.0183(13) -0.0239(14) C5 0.0401(15) 0.061(2) 0.0682(19) -0.0377(17) 0.0200(14) -0.0241(14) C6 0.057(2) 0.0498(19) 0.106(3) 0.027(2) -0.024(2) -0.0179(16) C7 0.059(2) 0.093(3) 0.0450(15) -0.0324(16) 0.0243(14) -0.047(2) C8 0.0419(18) 0.0423(18) 0.115(3) 0.0150(19) -0.0208(18) -0.0092(14) C9 0.0224(11) 0.0266(11) 0.0278(10) -0.0006(8) -0.0022(8) -0.0048(8) C10 0.0290(12) 0.0325(14) 0.0389(12) -0.0020(9) -0.0023(9) -0.0091(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 1.9197(16) 7_545 ? Zn1 O4 1.9349(16) . ? Zn1 O1 1.9372(14) 5_644 ? Zn1 O3 1.9434(17) 3_544 ? O1 C9 1.253(3) . ? O1 Zn1 1.9372(14) 5_654 ? O2 C9 1.257(3) . ? O2 Zn1 1.9197(16) 7_655 ? O3 C10 1.263(3) . ? O3 Zn1 1.9434(17) 4 ? O4 C10 1.258(3) . ? C1 C5 1.509(3) . ? C1 C9 1.509(3) . ? C1 C2 1.569(3) . ? C1 C6 1.570(4) . ? C2 C8 1.518(4) . ? C2 C7 1.521(3) . ? C2 C3 1.528(3) . ? C3 C4 1.312(3) . ? C3 C10 1.482(3) . ? C4 C5 1.503(4) . ? C4 H4A 0.9300 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? 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 Zn1 O4 126.38(8) 7_545 . ? O2 Zn1 O1 100.51(7) 7_545 5_644 ? O4 Zn1 O1 96.34(7) . 5_644 ? O2 Zn1 O3 102.09(8) 7_545 3_544 ? O4 Zn1 O3 108.09(8) . 3_544 ? O1 Zn1 O3 125.85(7) 5_644 3_544 ? C9 O1 Zn1 127.75(15) . 5_654 ? C9 O2 Zn1 139.56(15) . 7_655 ? C10 O3 Zn1 129.59(15) . 4 ? C10 O4 Zn1 128.65(17) . . ? C5 C1 C9 114.0(2) . . ? C5 C1 C2 104.8(2) . . ? C9 C1 C2 115.1(2) . . ? C5 C1 C6 107.6(3) . . ? C9 C1 C6 104.0(2) . . ? C2 C1 C6 111.3(2) . . ? C8 C2 C7 110.3(3) . . ? C8 C2 C3 107.7(2) . . ? C7 C2 C3 114.4(2) . . ? C8 C2 C1 111.0(2) . . ? C7 C2 C1 113.0(2) . . ? C3 C2 C1 100.02(18) . . ? C4 C3 C10 123.2(2) . . ? C4 C3 C2 112.2(2) . . ? C10 C3 C2 124.6(2) . . ? C3 C4 C5 111.5(2) . . ? C3 C4 H4A 124.3 . . ? C5 C4 H4A 124.3 . . ? C4 C5 C1 103.1(2) . . ? C4 C5 H5A 111.1 . . ? C1 C5 H5A 111.1 . . ? C4 C5 H5B 111.1 . . ? C1 C5 H5B 111.1 . . ? H5A C5 H5B 109.1 . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O1 C9 O2 125.0(2) . . ? O1 C9 C1 117.8(2) . . ? O2 C9 C1 117.05(19) . . ? O4 C10 O3 123.8(2) . . ? O4 C10 C3 117.0(2) . . ? O3 C10 C3 119.2(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.18 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.476 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.063 # Attachment '2.cif' data_2_a _database_code_depnum_ccdc_archive 'CCDC 671277' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H56 N2 O16 Zn4' _chemical_formula_weight 1202.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P222(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' _cell_length_a 7.4577(11) _cell_length_b 14.967(3) _cell_length_c 22.633(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2526.3(7) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1999 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 23.59 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max .25 _exptl_crystal_size_mid .13 _exptl_crystal_size_min .10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1236 _exptl_absorpt_coefficient_mu 1.948 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.83 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 18457 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.07 _reflns_number_total 4466 _reflns_number_gt 3566 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0565P)^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 0.02(2) _chemical_absolute_configuration rm _refine_ls_number_reflns 4466 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1055 _refine_ls_wR_factor_gt 0.0964 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 Zn1 Zn 0.48603(10) 0.0000 1.0000 0.02147(18) Uani 1 2 d S . . Zn2 Zn 0.5000 0.52609(5) 0.7500 0.0295(2) Uani 1 2 d S . . Zn3 Zn 0.00606(10) 0.0000 1.0000 0.02198(17) Uani 1 2 d S . . Zn4 Zn 0.0000 0.49334(4) 0.7500 0.02381(18) Uani 1 2 d S . . O1 O 0.4368(5) 0.4565(2) 0.81755(17) 0.0561(11) Uani 1 1 d . . . O2 O 0.1677(5) 0.4090(2) 0.78675(16) 0.0463(10) Uani 1 1 d . . . O3 O 0.2789(4) 0.0994(3) 0.99825(15) 0.0368(10) Uani 1 1 d . . . O4 O 0.0554(5) 0.0944(2) 0.93569(15) 0.0410(9) Uani 1 1 d . . . O5 O 0.6958(5) 0.3971(2) 1.22491(16) 0.0494(10) Uani 1 1 d . . . O6 O 0.9350(5) 0.4419(2) 1.17875(17) 0.0559(11) Uani 1 1 d . . . O7 O 0.6819(4) 0.1002(3) 1.00363(15) 0.0320(9) Uani 1 1 d . . . O8 O 0.9233(4) 0.08924(19) 1.05934(14) 0.0328(8) Uani 1 1 d . . . N1 N 0.4858(5) -0.00159(18) 1.09420(15) 0.0250(8) Uani 1 1 d . . . C1 C 0.2845(6) 0.3549(3) 0.8792(2) 0.0313(11) Uani 1 1 d . . . C2 C 0.1715(6) 0.2650(3) 0.8765(2) 0.0315(11) Uani 1 1 d . . . C3 C 0.2664(6) 0.2124(3) 0.9256(2) 0.0312(12) Uani 1 1 d . . . C4 C 0.4315(7) 0.2432(3) 0.9349(3) 0.0465(14) Uani 1 1 d . . . H4A H 0.5123 0.2172 0.9610 0.056 Uiso 1 1 calc R . . C5 C 0.4724(7) 0.3233(3) 0.8989(2) 0.0490(14) Uani 1 1 d . . . H5A H 0.5467 0.3083 0.8652 0.059 Uiso 1 1 calc R . . H5B H 0.5324 0.3687 0.9223 0.059 Uiso 1 1 calc R . . C6 C 0.2101(9) 0.4204(4) 0.9258(3) 0.0594(17) Uani 1 1 d . . . H6A H 0.2812 0.4739 0.9259 0.089 Uiso 1 1 calc R . . H6B H 0.2146 0.3931 0.9641 0.089 Uiso 1 1 calc R . . H6C H 0.0882 0.4351 0.9163 0.089 Uiso 1 1 calc R . . C7 C 0.2044(8) 0.2146(3) 0.8189(3) 0.0562(16) Uani 1 1 d . . . H7A H 0.1346 0.1606 0.8186 0.084 Uiso 1 1 calc R . . H7B H 0.3293 0.1999 0.8156 0.084 Uiso 1 1 calc R . . H7C H 0.1698 0.2514 0.7861 0.084 Uiso 1 1 calc R . . C8 C -0.0272(7) 0.2786(4) 0.8851(3) 0.0645(18) Uani 1 1 d . . . H8A H -0.0871 0.2219 0.8834 0.097 Uiso 1 1 calc R . . H8B H -0.0725 0.3167 0.8544 0.097 Uiso 1 1 calc R . . H8C H -0.0484 0.3058 0.9228 0.097 Uiso 1 1 calc R . . C9 C 0.2939(7) 0.4093(3) 0.8221(2) 0.0361(12) Uani 1 1 d . . . C10 C 0.1952(7) 0.1310(3) 0.9538(2) 0.0313(12) Uani 1 1 d . . . C11 C 0.7333(6) 0.3523(3) 1.1233(2) 0.0330(12) Uani 1 1 d . . . C12 C 0.8537(6) 0.2655(3) 1.1143(2) 0.0322(12) Uani 1 1 d . . . C13 C 0.7260(6) 0.2085(3) 1.0782(2) 0.0281(11) Uani 1 1 d . . . C14 C 0.5561(7) 0.2349(3) 1.0846(2) 0.0400(13) Uani 1 1 d . . . H14A H 0.4589 0.2075 1.0664 0.048 Uiso 1 1 calc R . . C15 C 0.5413(6) 0.3140(3) 1.1246(3) 0.0492(14) Uani 1 1 d . . . H15A H 0.5072 0.2963 1.1643 0.059 Uiso 1 1 calc R . . H15B H 0.4549 0.3570 1.1098 0.059 Uiso 1 1 calc R . . C16 C 0.7498(8) 0.4178(4) 1.0717(3) 0.0543(16) Uani 1 1 d . . . H16A H 0.6755 0.4690 1.0790 0.081 Uiso 1 1 calc R . . H16B H 0.7118 0.3891 1.0359 0.081 Uiso 1 1 calc R . . H16C H 0.8724 0.4365 1.0678 0.081 Uiso 1 1 calc R . . C17 C 1.0314(7) 0.2851(3) 1.0822(3) 0.0580(17) Uani 1 1 d . . . H17A H 1.0987 0.2308 1.0781 0.087 Uiso 1 1 calc R . . H17B H 1.0998 0.3275 1.1047 0.087 Uiso 1 1 calc R . . H17C H 1.0066 0.3094 1.0438 0.087 Uiso 1 1 calc R . . C18 C 0.8928(8) 0.2200(4) 1.1730(3) 0.0599(17) Uani 1 1 d . . . H18A H 0.9648 0.1678 1.1663 0.090 Uiso 1 1 calc R . . H18B H 0.7820 0.2030 1.1914 0.090 Uiso 1 1 calc R . . H18C H 0.9564 0.2606 1.1983 0.090 Uiso 1 1 calc R . . C19 C 0.7894(7) 0.4005(3) 1.1792(3) 0.0402(13) Uani 1 1 d . . . C20 C 0.7798(6) 0.1276(3) 1.0451(2) 0.0277(11) Uani 1 1 d . . . C21 C 0.6243(6) -0.0372(3) 1.12374(19) 0.0312(11) Uani 1 1 d . . . H21A H 0.7166 -0.0637 1.1023 0.037 Uiso 1 1 calc R . . C22 C 0.6355(6) -0.0361(3) 1.1845(2) 0.0366(12) Uani 1 1 d . . . H22A H 0.7356 -0.0599 1.2033 0.044 Uiso 1 1 calc R . . C23 C 0.4971(6) 0.0004(2) 1.21742(18) 0.0295(10) Uani 1 1 d . . . C24 C 0.3524(6) 0.0354(3) 1.1864(2) 0.0355(11) Uani 1 1 d . . . H24A H 0.2552 0.0595 1.2066 0.043 Uiso 1 1 calc R . . C25 C 0.3537(6) 0.0342(3) 1.12555(19) 0.0318(11) Uani 1 1 d . . . H25A H 0.2575 0.0596 1.1055 0.038 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 Zn1 0.0256(4) 0.0255(3) 0.0133(4) 0.0005(2) 0.000 0.000 Zn2 0.0276(4) 0.0316(4) 0.0293(4) 0.000 -0.0008(4) 0.000 Zn3 0.0303(4) 0.0164(3) 0.0192(4) -0.0002(2) 0.000 0.000 Zn4 0.0276(4) 0.0212(3) 0.0226(4) 0.000 -0.0029(3) 0.000 O1 0.053(2) 0.050(2) 0.065(3) 0.024(2) -0.008(2) -0.0099(19) O2 0.066(3) 0.0280(18) 0.046(2) 0.0094(16) -0.021(2) 0.0030(17) O3 0.046(2) 0.033(2) 0.032(2) 0.0095(16) 0.0088(19) 0.0146(16) O4 0.053(2) 0.0326(17) 0.038(2) 0.0059(15) -0.0015(17) -0.0178(15) O5 0.060(3) 0.042(2) 0.047(3) -0.0078(17) 0.005(2) 0.0169(18) O6 0.055(2) 0.059(3) 0.053(3) -0.0304(19) -0.001(2) -0.0159(19) O7 0.0394(19) 0.030(2) 0.027(2) -0.0021(15) -0.0017(16) -0.0121(16) O8 0.0418(19) 0.0265(16) 0.030(2) -0.0062(14) -0.0047(15) 0.0089(14) N1 0.033(2) 0.0258(16) 0.0163(19) 0.0014(12) 0.0015(18) 0.006(2) C1 0.037(3) 0.025(3) 0.033(3) 0.009(2) -0.003(2) -0.006(2) C2 0.031(3) 0.025(2) 0.039(3) 0.010(2) -0.003(2) 0.002(2) C3 0.035(3) 0.025(3) 0.033(3) 0.004(2) 0.000(2) 0.000(2) C4 0.043(3) 0.043(3) 0.054(4) 0.024(3) -0.017(3) -0.003(2) C5 0.041(3) 0.047(3) 0.060(4) 0.025(2) -0.013(3) -0.011(3) C6 0.097(5) 0.036(3) 0.045(4) 0.003(3) 0.009(3) -0.004(3) C7 0.089(4) 0.033(3) 0.047(4) 0.006(3) -0.015(3) -0.005(3) C8 0.039(3) 0.052(3) 0.102(5) 0.034(3) -0.011(3) -0.004(3) C9 0.043(3) 0.024(3) 0.041(3) 0.008(2) 0.000(3) 0.007(2) C10 0.047(3) 0.018(2) 0.029(3) 0.004(2) 0.007(3) 0.008(2) C11 0.038(3) 0.025(3) 0.036(3) -0.009(2) 0.000(2) 0.001(2) C12 0.029(3) 0.028(3) 0.040(3) -0.017(2) -0.001(2) 0.000(2) C13 0.034(3) 0.025(3) 0.025(3) -0.005(2) -0.004(2) 0.001(2) C14 0.034(3) 0.031(3) 0.055(4) -0.012(2) -0.008(3) -0.001(2) C15 0.035(3) 0.043(3) 0.070(4) -0.021(3) 0.005(3) 0.009(2) C16 0.072(4) 0.038(3) 0.053(4) 0.000(3) -0.010(3) 0.003(3) C17 0.038(3) 0.050(3) 0.086(5) -0.032(3) 0.014(3) -0.011(3) C18 0.090(4) 0.044(3) 0.046(4) -0.016(3) -0.023(3) 0.018(3) C19 0.046(3) 0.027(3) 0.048(4) -0.015(2) 0.006(3) 0.008(2) C20 0.043(3) 0.022(3) 0.018(3) -0.001(2) 0.001(2) -0.008(2) C21 0.040(3) 0.039(3) 0.014(3) -0.003(2) 0.004(2) 0.003(2) C22 0.038(3) 0.049(3) 0.023(3) 0.005(2) -0.005(2) 0.012(2) C23 0.037(3) 0.033(2) 0.018(2) -0.0013(15) -0.001(2) 0.001(3) C24 0.040(3) 0.043(3) 0.024(3) -0.003(2) 0.003(2) 0.007(2) C25 0.037(3) 0.040(3) 0.018(3) 0.001(2) -0.006(2) 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 O7 2.094(4) . ? Zn1 O7 2.094(4) 4_557 ? Zn1 N1 2.132(3) 4_557 ? Zn1 N1 2.132(3) . ? Zn1 O3 2.144(4) 4_557 ? Zn1 O3 2.144(4) . ? Zn2 O1 1.909(4) 3_656 ? Zn2 O1 1.909(4) . ? Zn2 O5 1.943(4) 4_567 ? Zn2 O5 1.943(3) 2_664 ? Zn3 O8 1.992(3) 4_457 ? Zn3 O8 1.992(3) 1_455 ? Zn3 O4 2.061(3) . ? Zn3 O4 2.061(3) 4_557 ? Zn4 O6 1.943(3) 4_467 ? Zn4 O6 1.943(3) 2_664 ? Zn4 O2 1.962(3) 3_556 ? Zn4 O2 1.962(3) . ? O1 C9 1.283(6) . ? O2 C9 1.235(6) . ? O3 C10 1.275(6) . ? O4 C10 1.247(6) . ? O5 C19 1.249(6) . ? O5 Zn2 1.943(3) 2_665 ? O6 C19 1.250(6) . ? O6 Zn4 1.943(3) 2_665 ? O7 C20 1.259(5) . ? O8 C20 1.256(5) . ? O8 Zn3 1.992(3) 1_655 ? N1 C25 1.327(5) . ? N1 C21 1.341(6) . ? C1 C9 1.530(7) . ? C1 C6 1.542(7) . ? C1 C5 1.544(6) . ? C1 C2 1.589(6) . ? C2 C8 1.508(7) . ? C2 C7 1.528(7) . ? C2 C3 1.534(6) . ? C3 C4 1.331(7) . ? C3 C10 1.475(6) . ? C4 C5 1.481(6) . ? C4 H4A 0.9300 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C11 C19 1.515(7) . ? C11 C16 1.530(7) . ? C11 C15 1.543(7) . ? C11 C12 1.593(6) . ? C12 C13 1.517(6) . ? C12 C18 1.521(7) . ? C12 C17 1.540(7) . ? C13 C14 1.335(6) . ? C13 C20 1.479(6) . ? C14 C15 1.495(6) . ? C14 H14A 0.9300 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C21 C22 1.378(6) . ? C21 H21A 0.9300 . ? C22 C23 1.386(6) . ? C22 H22A 0.9300 . ? C23 C24 1.390(6) . ? C23 C23 1.476(8) 3_657 ? C24 C25 1.377(6) . ? C24 H24A 0.9300 . ? 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 O7 Zn1 O7 91.6(2) . 4_557 ? O7 Zn1 N1 91.83(13) . 4_557 ? O7 Zn1 N1 88.24(13) 4_557 4_557 ? O7 Zn1 N1 88.24(13) . . ? O7 Zn1 N1 91.83(13) 4_557 . ? N1 Zn1 N1 179.9(2) 4_557 . ? O7 Zn1 O3 176.22(16) . 4_557 ? O7 Zn1 O3 90.37(13) 4_557 4_557 ? N1 Zn1 O3 91.47(13) 4_557 4_557 ? N1 Zn1 O3 88.46(13) . 4_557 ? O7 Zn1 O3 90.37(13) . . ? O7 Zn1 O3 176.22(16) 4_557 . ? N1 Zn1 O3 88.46(13) 4_557 . ? N1 Zn1 O3 91.47(13) . . ? O3 Zn1 O3 87.9(2) 4_557 . ? O1 Zn2 O1 113.9(2) 3_656 . ? O1 Zn2 O5 111.79(15) 3_656 4_567 ? O1 Zn2 O5 105.92(16) . 4_567 ? O1 Zn2 O5 105.92(16) 3_656 2_664 ? O1 Zn2 O5 111.79(15) . 2_664 ? O5 Zn2 O5 107.4(2) 4_567 2_664 ? O8 Zn3 O8 143.91(19) 4_457 1_455 ? O8 Zn3 O4 92.21(14) 4_457 . ? O8 Zn3 O4 94.13(15) 1_455 . ? O8 Zn3 O4 94.13(15) 4_457 4_557 ? O8 Zn3 O4 92.21(14) 1_455 4_557 ? O4 Zn3 O4 159.4(2) . 4_557 ? O6 Zn4 O6 120.1(2) 4_467 2_664 ? O6 Zn4 O2 120.93(16) 4_467 3_556 ? O6 Zn4 O2 97.37(16) 2_664 3_556 ? O6 Zn4 O2 97.37(15) 4_467 . ? O6 Zn4 O2 120.93(16) 2_664 . ? O2 Zn4 O2 99.9(2) 3_556 . ? C9 O1 Zn2 124.7(4) . . ? C9 O2 Zn4 139.3(3) . . ? C10 O3 Zn1 128.6(3) . . ? C10 O4 Zn3 102.6(3) . . ? C19 O5 Zn2 129.6(3) . 2_665 ? C19 O6 Zn4 117.2(4) . 2_665 ? C20 O7 Zn1 131.9(3) . . ? C20 O8 Zn3 113.4(3) . 1_655 ? C25 N1 C21 117.8(4) . . ? C25 N1 Zn1 122.1(3) . . ? C21 N1 Zn1 120.1(3) . . ? C9 C1 C6 104.8(4) . . ? C9 C1 C5 111.4(4) . . ? C6 C1 C5 108.9(5) . . ? C9 C1 C2 116.3(4) . . ? C6 C1 C2 112.0(4) . . ? C5 C1 C2 103.5(4) . . ? C8 C2 C7 109.5(5) . . ? C8 C2 C3 115.4(4) . . ? C7 C2 C3 106.9(4) . . ? C8 C2 C1 113.7(4) . . ? C7 C2 C1 111.5(4) . . ? C3 C2 C1 99.3(4) . . ? C4 C3 C10 123.4(5) . . ? C4 C3 C2 111.3(4) . . ? C10 C3 C2 124.8(4) . . ? C3 C4 C5 112.6(5) . . ? C3 C4 H4A 123.7 . . ? C5 C4 H4A 123.7 . . ? C4 C5 C1 102.7(4) . . ? C4 C5 H5A 111.2 . . ? C1 C5 H5A 111.2 . . ? C4 C5 H5B 111.2 . . ? C1 C5 H5B 111.2 . . ? H5A C5 H5B 109.1 . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C9 O1 125.7(5) . . ? O2 C9 C1 120.7(4) . . ? O1 C9 C1 113.5(5) . . ? O4 C10 O3 120.4(4) . . ? O4 C10 C3 121.5(4) . . ? O3 C10 C3 118.1(5) . . ? C19 C11 C16 108.1(4) . . ? C19 C11 C15 114.6(4) . . ? C16 C11 C15 109.1(5) . . ? C19 C11 C12 109.8(4) . . ? C16 C11 C12 112.3(4) . . ? C15 C11 C12 102.9(4) . . ? C13 C12 C18 109.8(4) . . ? C13 C12 C17 113.2(4) . . ? C18 C12 C17 109.4(5) . . ? C13 C12 C11 100.0(4) . . ? C18 C12 C11 111.2(4) . . ? C17 C12 C11 112.9(4) . . ? C14 C13 C20 123.7(4) . . ? C14 C13 C12 111.8(4) . . ? C20 C13 C12 124.2(4) . . ? C13 C14 C15 111.7(4) . . ? C13 C14 H14A 124.1 . . ? C15 C14 H14A 124.1 . . ? C14 C15 C11 102.3(4) . . ? C14 C15 H15A 111.3 . . ? C11 C15 H15A 111.3 . . ? C14 C15 H15B 111.3 . . ? C11 C15 H15B 111.3 . . ? H15A C15 H15B 109.2 . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C12 C18 H18A 109.5 . . ? C12 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C12 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O5 C19 O6 120.8(5) . . ? O5 C19 C11 121.2(5) . . ? O6 C19 C11 118.0(5) . . ? O8 C20 O7 122.4(4) . . ? O8 C20 C13 118.4(4) . . ? O7 C20 C13 119.2(4) . . ? N1 C21 C22 122.7(4) . . ? N1 C21 H21A 118.7 . . ? C22 C21 H21A 118.7 . . ? C21 C22 C23 119.7(4) . . ? C21 C22 H22A 120.1 . . ? C23 C22 H22A 120.1 . . ? C22 C23 C24 117.1(4) . . ? C22 C23 C23 121.0(5) . 3_657 ? C24 C23 C23 121.8(5) . 3_657 ? C25 C24 C23 119.6(4) . . ? C25 C24 H24A 120.2 . . ? C23 C24 H24A 120.2 . . ? N1 C25 C24 123.0(4) . . ? N1 C25 H25A 118.5 . . ? C24 C25 H25A 118.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.767 _refine_diff_density_min -0.783 _refine_diff_density_rms 0.096