# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Anthony Cheetham' _publ_contact_author_address ; Materials Department University of California Santa Barbara California 93106 UNITED STATES OF AMERICA ; _publ_contact_author_email CHEETHAM@MRL.UCSB.EDU _publ_section_title ; Interplay of Thermodynamic and Kinetic Factors in the Hydrothermal Syntheses of Hybrid Networks: Zinc 4-Cyclohexene 1,2 Dicarboxylates ; loop_ _publ_author_name 'A. Cheetham' 'William T. A. Harrison' 'Clare Lee' 'Caroline Mellot-Draznieks' 'C. N. R. Rao' ; B.Slater ; 'G. Wu' # Attachment 'CLARE01_p.cif' data_clare01 _database_code_depnum_ccdc_archive 'CCDC 298856' # TRANS ANHYDROUS FORM _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 O4 Zn' _chemical_formula_sum 'C8 H8 O4 Zn' _chemical_formula_weight 233.52 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.8606(4) _cell_length_b 6.7240(5) _cell_length_c 13.1788(11) _cell_angle_alpha 98.071(1) _cell_angle_beta 98.236(1) _cell_angle_gamma 95.585(1) _cell_volume 419.01(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.851 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 236 _exptl_absorpt_coefficient_mu 2.905 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.594 _exptl_absorpt_correction_T_max 0.868 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3229 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1595 _reflns_number_gt 1497 _reflns_threshold_expression I>2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0528P)^2^+0.5936P] 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 1595 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0925 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.75484(7) -0.29625(5) 0.07919(3) 0.02305(16) Uani 1 1 d . . . O1 O 0.5918(5) -0.0797(4) 0.1565(2) 0.0331(6) Uani 1 1 d . . . O2 O 0.1653(5) -0.2376(3) 0.11098(19) 0.0295(5) Uani 1 1 d . . . O3 O 0.2953(5) 0.2797(4) 0.06599(19) 0.0362(6) Uani 1 1 d . . . O4 O 0.6856(5) 0.4729(4) 0.1471(2) 0.0370(6) Uani 1 1 d . . . C1 C 0.3332(6) -0.0905(5) 0.1594(3) 0.0233(6) Uani 1 1 d . . . C2 C 0.4760(7) 0.3463(5) 0.1440(3) 0.0262(7) Uani 1 1 d . . . C3 C 0.2364(7) 0.0771(5) 0.2294(3) 0.0268(7) Uani 1 1 d . . . H3 H 0.0502 0.1018 0.1979 0.032 Uiso 1 1 calc R . . C4 C 0.4347(7) 0.2746(5) 0.2453(3) 0.0290(7) Uani 1 1 d . . . H4 H 0.6174 0.2510 0.2806 0.035 Uiso 1 1 calc R . . C5 C 0.3287(10) 0.4417(6) 0.3123(3) 0.0461(10) Uani 1 1 d . . . H5A H 0.4764 0.5538 0.3342 0.055 Uiso 1 1 calc R . . H5B H 0.1732 0.4898 0.2719 0.055 Uiso 1 1 calc R . . C6 C 0.2347(12) 0.3716(8) 0.4066(4) 0.0616(13) Uani 1 1 d . . . H6 H 0.2063 0.4687 0.4605 0.074 Uiso 1 1 calc R . . C7 C 0.1906(13) 0.1797(9) 0.4166(4) 0.0672(15) Uani 1 1 d . . . H7 H 0.1413 0.1494 0.4788 0.081 Uiso 1 1 calc R . . C8 C 0.2142(12) 0.0081(7) 0.3352(4) 0.0522(12) Uani 1 1 d . . . H8A H 0.0513 -0.0917 0.3274 0.063 Uiso 1 1 calc R . . H8B H 0.3785 -0.0559 0.3569 0.063 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 0.0192(2) 0.0208(2) 0.0288(2) 0.00490(15) 0.00445(15) -0.00186(14) O1 0.0180(12) 0.0300(13) 0.0489(15) -0.0022(11) 0.0083(10) -0.0014(9) O2 0.0196(11) 0.0213(11) 0.0454(14) -0.0015(10) 0.0072(10) -0.0012(9) O3 0.0385(14) 0.0390(14) 0.0298(13) 0.0086(11) 0.0047(11) -0.0049(11) O4 0.0307(13) 0.0323(13) 0.0490(16) 0.0183(11) 0.0032(11) -0.0046(11) C1 0.0203(15) 0.0198(15) 0.0314(17) 0.0072(12) 0.0067(12) 0.0018(12) C2 0.0282(17) 0.0190(15) 0.0332(18) 0.0071(13) 0.0075(14) 0.0034(13) C3 0.0279(17) 0.0204(15) 0.0327(18) 0.0036(13) 0.0104(14) -0.0018(13) C4 0.0345(18) 0.0214(16) 0.0294(17) 0.0034(13) 0.0038(14) -0.0028(14) C5 0.058(3) 0.033(2) 0.048(2) 0.0002(17) 0.014(2) 0.0068(19) C6 0.080(4) 0.056(3) 0.048(3) -0.007(2) 0.028(3) 0.004(3) C7 0.098(4) 0.062(3) 0.045(3) 0.006(2) 0.033(3) -0.007(3) C8 0.080(3) 0.033(2) 0.052(3) 0.0142(18) 0.035(2) 0.003(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 O3 1.914(2) 2_655 ? Zn1 O4 1.924(2) 1_545 ? Zn1 O1 1.956(2) . ? Zn1 O2 1.968(2) 1_655 ? O1 C1 1.259(4) . ? O2 C1 1.252(4) . ? O2 Zn1 1.968(2) 1_455 ? O3 C2 1.251(4) . ? O3 Zn1 1.914(2) 2_655 ? O4 C2 1.254(4) . ? O4 Zn1 1.924(2) 1_565 ? C1 C3 1.509(4) . ? C2 C4 1.514(5) . ? C3 C4 1.534(5) . ? C3 C8 1.544(5) . ? C3 H3 0.9800 . ? C4 C5 1.507(5) . ? C4 H4 0.9800 . ? C5 C6 1.503(7) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.316(8) . ? C6 H6 0.9300 . ? C7 C8 1.487(7) . ? C7 H7 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 O4 129.25(12) 2_655 1_545 ? O3 Zn1 O1 111.25(11) 2_655 . ? O4 Zn1 O1 104.84(12) 1_545 . ? O3 Zn1 O2 99.10(11) 2_655 1_655 ? O4 Zn1 O2 102.02(10) 1_545 1_655 ? O1 Zn1 O2 108.44(9) . 1_655 ? C1 O1 Zn1 121.7(2) . . ? C1 O2 Zn1 134.8(2) . 1_455 ? C2 O3 Zn1 136.9(2) . 2_655 ? C2 O4 Zn1 133.9(2) . 1_565 ? O2 C1 O1 122.0(3) . . ? O2 C1 C3 121.3(3) . . ? O1 C1 C3 116.7(3) . . ? O3 C2 O4 125.9(3) . . ? O3 C2 C4 117.6(3) . . ? O4 C2 C4 116.4(3) . . ? C1 C3 C4 112.1(3) . . ? C1 C3 C8 108.8(3) . . ? C4 C3 C8 109.9(3) . . ? C1 C3 H3 108.6 . . ? C4 C3 H3 108.6 . . ? C8 C3 H3 108.6 . . ? C5 C4 C2 108.2(3) . . ? C5 C4 C3 111.2(3) . . ? C2 C4 C3 112.7(3) . . ? C5 C4 H4 108.2 . . ? C2 C4 H4 108.2 . . ? C3 C4 H4 108.2 . . ? C6 C5 C4 111.8(4) . . ? C6 C5 H5A 109.3 . . ? C4 C5 H5A 109.3 . . ? C6 C5 H5B 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 123.2(4) . . ? C7 C6 H6 118.4 . . ? C5 C6 H6 118.4 . . ? C6 C7 C8 124.4(5) . . ? C6 C7 H7 117.8 . . ? C8 C7 H7 117.8 . . ? C7 C8 C3 112.1(4) . . ? C7 C8 H8A 109.2 . . ? C3 C8 H8A 109.2 . . ? C7 C8 H8B 109.2 . . ? C3 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Zn1 O1 C1 80.0(3) 2_655 . . . ? O4 Zn1 O1 C1 -63.7(3) 1_545 . . . ? O2 Zn1 O1 C1 -172.1(2) 1_655 . . . ? Zn1 O2 C1 O1 -169.9(2) 1_455 . . . ? Zn1 O2 C1 C3 13.7(5) 1_455 . . . ? Zn1 O1 C1 O2 -1.9(4) . . . . ? Zn1 O1 C1 C3 174.6(2) . . . . ? Zn1 O3 C2 O4 7.9(6) 2_655 . . . ? Zn1 O3 C2 C4 -174.5(2) 2_655 . . . ? Zn1 O4 C2 O3 34.3(5) 1_565 . . . ? Zn1 O4 C2 C4 -143.3(3) 1_565 . . . ? O2 C1 C3 C4 -156.9(3) . . . . ? O1 C1 C3 C4 26.5(4) . . . . ? O2 C1 C3 C8 81.2(4) . . . . ? O1 C1 C3 C8 -95.3(4) . . . . ? O3 C2 C4 C5 -103.1(4) . . . . ? O4 C2 C4 C5 74.7(4) . . . . ? O3 C2 C4 C3 20.3(4) . . . . ? O4 C2 C4 C3 -161.9(3) . . . . ? C1 C3 C4 C5 178.0(3) . . . . ? C8 C3 C4 C5 -60.8(4) . . . . ? C1 C3 C4 C2 56.3(4) . . . . ? C8 C3 C4 C2 177.5(3) . . . . ? C2 C4 C5 C6 170.2(4) . . . . ? C3 C4 C5 C6 45.9(5) . . . . ? C4 C5 C6 C7 -14.4(8) . . . . ? C5 C6 C7 C8 -3.0(11) . . . . ? C6 C7 C8 C3 -11.8(9) . . . . ? C1 C3 C8 C7 165.6(4) . . . . ? C4 C3 C8 C7 42.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 1.042 _refine_diff_density_min -0.502 _refine_diff_density_rms 0.102 # Attachment 'WH602_p.cif' data_wh602 _database_code_depnum_ccdc_archive 'CCDC 298857' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 O4 Zn, 2(H2 O)' _chemical_formula_sum 'C8 H12 O6 Zn' _chemical_formula_weight 269.55 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.7790(2) _cell_length_b 12.0260(4) _cell_length_c 8.5260(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.9436(17) _cell_angle_gamma 90.00 _cell_volume 973.13(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2277 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.840 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 2.530 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.463 _exptl_absorpt_correction_T_max 0.804 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10666 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 27.52 _reflns_number_total 2228 _reflns_number_gt 2035 _reflns_threshold_expression I>2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0152P)^2^+0.8939P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'difmap (O-H) and geom (C-H)' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0084(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2228 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0263 _refine_ls_R_factor_gt 0.0225 _refine_ls_wR_factor_ref 0.0516 _refine_ls_wR_factor_gt 0.0498 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 0.014794(19) 0.217259(15) 0.08015(2) 0.00929(8) Uani 1 1 d . . . C1 C 0.22725(17) 0.08181(13) 0.17333(19) 0.0099(3) Uani 1 1 d . . . C2 C 0.33024(17) -0.00066(14) 0.27257(19) 0.0095(3) Uani 1 1 d . . . H2 H 0.3872 0.0419 0.3666 0.011 Uiso 1 1 calc R . . C3 C 0.43538(17) -0.04811(15) 0.1834(2) 0.0126(3) Uani 1 1 d . . . H3A H 0.3839 -0.0744 0.0752 0.015 Uiso 1 1 calc R . . H3B H 0.5009 0.0114 0.1680 0.015 Uiso 1 1 calc R . . C4 C 0.51838(18) -0.14272(15) 0.2746(2) 0.0145(4) Uani 1 1 d . . . H4 H 0.5992 -0.1675 0.2413 0.017 Uiso 1 1 calc R . . C5 C 0.48602(18) -0.19392(15) 0.3988(2) 0.0148(4) Uani 1 1 d . . . H5 H 0.5458 -0.2523 0.4501 0.018 Uiso 1 1 calc R . . C6 C 0.36003(18) -0.16465(15) 0.4627(2) 0.0133(3) Uani 1 1 d . . . H6A H 0.3920 -0.1244 0.5663 0.016 Uiso 1 1 calc R . . H6B H 0.3131 -0.2339 0.4843 0.016 Uiso 1 1 calc R . . C7 C 0.25343(17) -0.09225(14) 0.34435(19) 0.0093(3) Uani 1 1 d . . . H7 H 0.1943 -0.0540 0.4087 0.011 Uiso 1 1 calc R . . C8 C 0.15426(17) -0.16131(14) 0.21647(19) 0.0093(3) Uani 1 1 d . . . O1 O 0.22893(13) 0.11132(10) 0.03459(14) 0.0143(3) Uani 1 1 d . . . O2 O 0.13659(12) 0.12338(10) 0.24482(14) 0.0136(3) Uani 1 1 d . . . O3 O 0.12520(12) -0.12792(10) 0.07168(14) 0.0121(2) Uani 1 1 d . . . O4 O 0.09991(13) -0.24894(11) 0.25652(14) 0.0138(3) Uani 1 1 d . . . O5 O 0.07349(14) 0.36525(11) 0.03325(16) 0.0154(3) Uani 1 1 d . . . H10 H 0.116(2) 0.4096(19) 0.104(3) 0.019 Uiso 1 1 d . . . H11 H 0.102(2) 0.3669(19) -0.039(3) 0.019 Uiso 1 1 d . . . O6 O 0.19670(14) 0.51044(12) 0.25083(16) 0.0174(3) Uani 1 1 d . . . H12 H 0.162(2) 0.571(2) 0.244(3) 0.021 Uiso 1 1 d . . . H13 H 0.210(2) 0.4844(19) 0.340(3) 0.021 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01068(12) 0.00907(12) 0.00756(11) -0.00004(7) 0.00110(8) -0.00031(7) C1 0.0103(8) 0.0074(7) 0.0111(8) -0.0024(6) 0.0011(6) -0.0042(6) C2 0.0085(7) 0.0099(8) 0.0095(7) -0.0004(6) 0.0012(6) -0.0011(6) C3 0.0105(8) 0.0151(8) 0.0128(8) 0.0000(7) 0.0040(6) -0.0004(7) C4 0.0107(8) 0.0155(9) 0.0162(8) -0.0046(7) 0.0012(7) 0.0016(7) C5 0.0127(9) 0.0126(8) 0.0161(8) -0.0005(7) -0.0022(7) 0.0028(7) C6 0.0134(8) 0.0134(8) 0.0114(8) 0.0021(7) -0.0005(6) -0.0019(7) C7 0.0097(8) 0.0095(8) 0.0087(7) -0.0001(6) 0.0022(6) -0.0008(6) C8 0.0077(7) 0.0099(8) 0.0111(8) -0.0015(6) 0.0039(6) 0.0015(6) O1 0.0181(6) 0.0132(6) 0.0117(6) 0.0021(5) 0.0039(5) -0.0006(5) O2 0.0142(6) 0.0153(6) 0.0112(6) 0.0000(5) 0.0031(5) 0.0064(5) O3 0.0135(6) 0.0121(6) 0.0092(5) 0.0004(5) -0.0003(5) -0.0017(5) O4 0.0161(6) 0.0133(6) 0.0130(6) -0.0014(5) 0.0058(5) -0.0060(5) O5 0.0238(7) 0.0136(6) 0.0095(6) -0.0024(5) 0.0053(5) -0.0055(5) O6 0.0256(7) 0.0131(7) 0.0129(6) -0.0008(5) 0.0038(5) 0.0020(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O5 1.9409(13) . ? Zn1 O3 1.9622(12) 3 ? Zn1 O2 1.9643(12) . ? Zn1 O4 2.0287(12) 2 ? C1 O1 1.239(2) . ? C1 O2 1.291(2) . ? C1 C2 1.518(2) . ? C2 C3 1.529(2) . ? C2 C7 1.541(2) . ? C2 H2 1.0000 . ? C3 C4 1.501(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.327(3) . ? C4 H4 0.9500 . ? C5 C6 1.504(2) . ? C5 H5 0.9500 . ? C6 C7 1.535(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.520(2) . ? C7 H7 1.0000 . ? C8 O3 1.264(2) . ? C8 O4 1.264(2) . ? O3 Zn1 1.9622(12) 3 ? O4 Zn1 2.0287(12) 2_545 ? O5 H10 0.84(2) . ? O5 H11 0.73(2) . ? O6 H12 0.80(2) . ? O6 H13 0.81(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 O5 Zn1 O3 124.06(5) . 3 ? O5 Zn1 O2 121.05(5) . . ? O3 Zn1 O2 111.31(5) 3 . ? O5 Zn1 O4 101.40(6) . 2 ? O3 Zn1 O4 98.58(5) 3 2 ? O2 Zn1 O4 87.99(5) . 2 ? O1 C1 O2 120.55(15) . . ? O1 C1 C2 124.04(15) . . ? O2 C1 C2 115.38(14) . . ? C1 C2 C3 113.70(13) . . ? C1 C2 C7 111.54(13) . . ? C3 C2 C7 112.42(14) . . ? C1 C2 H2 106.2 . . ? C3 C2 H2 106.2 . . ? C7 C2 H2 106.2 . . ? C4 C3 C2 111.69(14) . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 124.17(16) . . ? C5 C4 H4 117.9 . . ? C3 C4 H4 117.9 . . ? C4 C5 C6 123.65(16) . . ? C4 C5 H5 118.2 . . ? C6 C5 H5 118.2 . . ? C5 C6 C7 112.35(14) . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C6 112.12(14) . . ? C8 C7 C2 113.18(13) . . ? C6 C7 C2 110.35(13) . . ? C8 C7 H7 106.9 . . ? C6 C7 H7 106.9 . . ? C2 C7 H7 106.9 . . ? O3 C8 O4 121.24(15) . . ? O3 C8 C7 118.79(14) . . ? O4 C8 C7 119.94(14) . . ? C1 O2 Zn1 104.60(10) . . ? C8 O3 Zn1 115.30(11) . 3 ? C8 O4 Zn1 133.68(11) . 2_545 ? Zn1 O5 H10 123.9(15) . . ? Zn1 O5 H11 112.9(18) . . ? H10 O5 H11 111(2) . . ? H12 O6 H13 113(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -1.9(2) . . . . ? O2 C1 C2 C3 179.83(14) . . . . ? O1 C1 C2 C7 -130.30(16) . . . . ? O2 C1 C2 C7 51.43(18) . . . . ? C1 C2 C3 C4 -170.36(14) . . . . ? C7 C2 C3 C4 -42.42(18) . . . . ? C2 C3 C4 C5 12.9(2) . . . . ? C3 C4 C5 C6 1.0(3) . . . . ? C4 C5 C6 C7 15.0(2) . . . . ? C5 C6 C7 C8 83.69(17) . . . . ? C5 C6 C7 C2 -43.48(19) . . . . ? C1 C2 C7 C8 61.31(17) . . . . ? C3 C2 C7 C8 -67.76(17) . . . . ? C1 C2 C7 C6 -172.12(13) . . . . ? C3 C2 C7 C6 58.81(17) . . . . ? C6 C7 C8 O3 -137.48(15) . . . . ? C2 C7 C8 O3 -11.8(2) . . . . ? C6 C7 C8 O4 44.2(2) . . . . ? C2 C7 C8 O4 169.84(14) . . . . ? O1 C1 O2 Zn1 5.16(18) . . . . ? C2 C1 O2 Zn1 -176.50(11) . . . . ? O5 Zn1 O2 C1 -80.07(11) . . . . ? O3 Zn1 O2 C1 79.41(11) 3 . . . ? O4 Zn1 O2 C1 177.84(10) 2 . . . ? O4 C8 O3 Zn1 2.8(2) . . . 3 ? C7 C8 O3 Zn1 -175.53(11) . . . 3 ? O3 C8 O4 Zn1 -123.88(15) . . . 2_545 ? C7 C8 O4 Zn1 54.4(2) . . . 2_545 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H10 O6 0.84(2) 1.79(2) 2.6200(19) 176(2) . O5 H11 O2 0.73(2) 1.96(2) 2.6793(18) 168(2) 4_565 O6 H12 O4 0.80(2) 2.26(3) 3.0485(19) 170(2) 1_565 O6 H13 O1 0.81(2) 1.99(2) 2.7801(18) 167(2) 4_566 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.458 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.071 # Attachment 'clare03_p.cif' data_clare03 _database_code_depnum_ccdc_archive 'CCDC 298858' # ANHYDROUS CIS FORM _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 O4 Zn' _chemical_formula_sum 'C8 H8 O4 Zn' _chemical_formula_weight 233.52 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 11.8544(14) _cell_length_b 13.0110(13) _cell_length_c 11.8523(13) _cell_angle_alpha 90.00 _cell_angle_beta 102.379(2) _cell_angle_gamma 90.00 _cell_volume 1785.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.737 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 2.727 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.495 _exptl_absorpt_correction_T_max 0.612 _exptl_absorpt_process_details 'SADABS (Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8257 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0628 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 24.74 _reflns_number_total 3017 _reflns_number_gt 2066 _reflns_threshold_expression I>2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0403P)^2^] 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 3017 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0855 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.45104(5) 0.24968(4) 0.32992(4) 0.03505(18) Uani 1 1 d . . . Zn2 Zn 0.57692(5) 0.05547(4) 0.23223(4) 0.03790(19) Uani 1 1 d . . . O1 O 0.3638(3) 0.4244(3) 0.3082(3) 0.0575(10) Uani 1 1 d . . . O2 O 0.3415(3) 0.3045(3) 0.4268(3) 0.0519(10) Uani 1 1 d . . . O3 O 0.4221(3) 0.4490(3) 0.6403(3) 0.0495(9) Uani 1 1 d . . . O4 O 0.3330(3) 0.3236(3) 0.7179(3) 0.0524(10) Uani 1 1 d . . . O5 O 0.6659(3) 0.1707(3) 0.1963(3) 0.0522(9) Uani 1 1 d . . . O6 O 0.5655(3) 0.3029(3) 0.2461(3) 0.0480(9) Uani 1 1 d . . . O7 O 0.5537(3) 0.3121(3) -0.0321(3) 0.0555(10) Uani 1 1 d . . . O8 O 0.5917(3) 0.4633(3) -0.1040(3) 0.0564(10) Uani 1 1 d . . . C1 C 0.3215(4) 0.3933(4) 0.3918(4) 0.0335(11) Uani 1 1 d . . . C2 C 0.2483(4) 0.4647(3) 0.4471(3) 0.0305(11) Uani 1 1 d . . . H2 H 0.2931 0.5277 0.4684 0.037 Uiso 1 1 calc R . . C3 C 0.1351(4) 0.4957(4) 0.3631(4) 0.0509(14) Uani 1 1 d . . . H3A H 0.1080 0.5602 0.3886 0.061 Uiso 1 1 calc R . . H3B H 0.1507 0.5065 0.2869 0.061 Uiso 1 1 calc R . . C4 C 0.0434(5) 0.4177(5) 0.3553(5) 0.0612(16) Uani 1 1 d . . . H4 H -0.0185 0.4204 0.2922 0.073 Uiso 1 1 calc R . . C5 C 0.0437(5) 0.3445(5) 0.4320(5) 0.0718(19) Uani 1 1 d . . . H5 H -0.0182 0.2990 0.4198 0.086 Uiso 1 1 calc R . . C6 C 0.1373(4) 0.3298(4) 0.5378(4) 0.0537(15) Uani 1 1 d . . . H6A H 0.1786 0.2667 0.5298 0.064 Uiso 1 1 calc R . . H6B H 0.1025 0.3222 0.6043 0.064 Uiso 1 1 calc R . . C7 C 0.2232(4) 0.4187(4) 0.5595(3) 0.0361(12) Uani 1 1 d . . . H7 H 0.1859 0.4734 0.5950 0.043 Uiso 1 1 calc R . . C8 C 0.3356(4) 0.3941(4) 0.6453(4) 0.0367(12) Uani 1 1 d . . . C9 C 0.6453(4) 0.2663(4) 0.2037(4) 0.0376(12) Uani 1 1 d . . . C10 C 0.7276(4) 0.3413(4) 0.1659(4) 0.0352(11) Uani 1 1 d . . . H10 H 0.7733 0.3707 0.2373 0.042 Uiso 1 1 calc R . . C11 C 0.8156(4) 0.2932(4) 0.1036(4) 0.0481(13) Uani 1 1 d . . . H11A H 0.8697 0.2515 0.1578 0.058 Uiso 1 1 calc R . . H11B H 0.7756 0.2486 0.0423 0.058 Uiso 1 1 calc R . . C12 C 0.8813(5) 0.3748(4) 0.0528(5) 0.0581(15) Uani 1 1 d . . . H12 H 0.9442 0.3537 0.0235 0.070 Uiso 1 1 calc R . . C13 C 0.8558(5) 0.4729(5) 0.0473(4) 0.0570(15) Uani 1 1 d . . . H13 H 0.9033 0.5175 0.0174 0.068 Uiso 1 1 calc R . . C14 C 0.7542(4) 0.5166(4) 0.0867(4) 0.0466(13) Uani 1 1 d . . . H14A H 0.7174 0.5683 0.0320 0.056 Uiso 1 1 calc R . . H14B H 0.7801 0.5496 0.1611 0.056 Uiso 1 1 calc R . . C15 C 0.6668(4) 0.4325(3) 0.0968(3) 0.0353(12) Uani 1 1 d . . . H15 H 0.6115 0.4610 0.1391 0.042 Uiso 1 1 calc R . . C16 C 0.6001(4) 0.3998(4) -0.0225(4) 0.0419(13) 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 0.0328(3) 0.0440(4) 0.0300(3) -0.0040(2) 0.0103(2) 0.0031(3) Zn2 0.0356(3) 0.0427(4) 0.0378(3) -0.0009(3) 0.0132(2) 0.0049(3) O1 0.068(3) 0.059(3) 0.057(2) -0.0133(18) 0.040(2) -0.018(2) O2 0.071(3) 0.049(2) 0.0392(19) 0.0072(17) 0.0188(17) 0.030(2) O3 0.041(2) 0.054(2) 0.048(2) 0.0055(17) -0.0017(16) -0.0102(19) O4 0.045(2) 0.067(3) 0.046(2) 0.0242(18) 0.0136(17) 0.0044(18) O5 0.048(2) 0.042(2) 0.071(2) 0.0068(19) 0.0237(18) 0.0030(19) O6 0.044(2) 0.054(2) 0.052(2) -0.0022(17) 0.0236(17) 0.0004(18) O7 0.048(2) 0.081(3) 0.0357(19) 0.0020(19) 0.0046(16) -0.022(2) O8 0.074(3) 0.058(3) 0.0345(19) 0.0082(17) 0.0051(17) 0.012(2) C1 0.027(3) 0.044(3) 0.028(2) -0.011(2) 0.001(2) 0.001(2) C2 0.027(3) 0.031(3) 0.035(2) 0.001(2) 0.009(2) 0.005(2) C3 0.036(3) 0.065(4) 0.053(3) 0.018(3) 0.012(2) 0.015(3) C4 0.036(3) 0.078(5) 0.064(4) 0.018(3) -0.001(3) -0.006(3) C5 0.047(4) 0.080(5) 0.081(4) 0.020(4) -0.004(3) -0.030(3) C6 0.039(3) 0.068(4) 0.054(3) 0.018(3) 0.011(3) -0.005(3) C7 0.033(3) 0.047(3) 0.031(2) 0.002(2) 0.011(2) 0.002(2) C8 0.036(3) 0.047(3) 0.028(2) 0.000(2) 0.009(2) 0.012(3) C9 0.033(3) 0.047(4) 0.031(2) 0.006(2) 0.004(2) -0.002(3) C10 0.028(3) 0.041(3) 0.035(2) 0.000(2) 0.004(2) 0.001(2) C11 0.035(3) 0.052(3) 0.062(3) -0.003(3) 0.021(3) 0.010(3) C12 0.045(3) 0.057(4) 0.084(4) -0.001(3) 0.039(3) 0.002(3) C13 0.052(4) 0.059(4) 0.066(4) -0.003(3) 0.027(3) -0.011(3) C14 0.053(4) 0.045(3) 0.044(3) -0.001(2) 0.015(3) 0.001(3) C15 0.035(3) 0.044(3) 0.028(2) -0.004(2) 0.010(2) -0.004(2) C16 0.032(3) 0.054(4) 0.044(3) 0.001(3) 0.018(2) 0.009(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O4 1.957(3) 4_565 ? Zn1 O6 1.971(3) . ? Zn1 O7 1.987(3) 4_566 ? Zn1 O2 2.038(3) . ? Zn1 O1 2.488(4) . ? Zn2 O3 1.924(3) 4_565 ? Zn2 O8 1.927(3) 4_566 ? Zn2 O5 1.933(3) . ? Zn2 O1 1.943(3) 2_645 ? O1 C1 1.269(5) . ? O1 Zn2 1.943(3) 2_655 ? O2 C1 1.233(5) . ? O3 C8 1.261(6) . ? O3 Zn2 1.924(3) 4_566 ? O4 C8 1.263(5) . ? O4 Zn1 1.957(3) 4_566 ? O5 C9 1.274(5) . ? O6 C9 1.257(5) . ? O7 C16 1.261(6) . ? O7 Zn1 1.987(3) 4_565 ? O8 C16 1.258(6) . ? O8 Zn2 1.927(3) 4_565 ? C1 C2 1.513(6) . ? C2 C3 1.543(6) . ? C2 C7 1.546(6) . ? C2 H2 0.9800 . ? C3 C4 1.475(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.316(7) . ? C4 H4 0.9300 . ? C5 C6 1.498(7) . ? C5 H5 0.9300 . ? C6 C7 1.526(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.526(6) . ? C7 H7 0.9800 . ? C9 C10 1.514(6) . ? C10 C15 1.532(6) . ? C10 C11 1.534(6) . ? C10 H10 0.9800 . ? C11 C12 1.516(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.310(7) . ? C12 H12 0.9300 . ? C13 C14 1.494(7) . ? C13 H13 0.9300 . ? C14 C15 1.529(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.526(6) . ? C15 H15 0.9800 . ? 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 O6 107.36(14) 4_565 . ? O4 Zn1 O7 125.68(16) 4_565 4_566 ? O6 Zn1 O7 101.02(14) . 4_566 ? O4 Zn1 O2 95.95(14) 4_565 . ? O6 Zn1 O2 138.73(15) . . ? O7 Zn1 O2 91.68(13) 4_566 . ? O4 Zn1 O1 98.87(13) 4_565 . ? O6 Zn1 O1 86.70(12) . . ? O7 Zn1 O1 128.50(14) 4_566 . ? O2 Zn1 O1 55.77(12) . . ? O3 Zn2 O8 115.88(16) 4_565 4_566 ? O3 Zn2 O5 113.44(15) 4_565 . ? O8 Zn2 O5 112.63(15) 4_566 . ? O3 Zn2 O1 100.69(15) 4_565 2_645 ? O8 Zn2 O1 100.21(14) 4_566 2_645 ? O5 Zn2 O1 112.54(15) . 2_645 ? C1 O1 Zn2 134.2(3) . 2_655 ? C1 O1 Zn1 81.5(3) . . ? Zn2 O1 Zn1 131.56(17) 2_655 . ? C1 O2 Zn1 103.8(3) . . ? C8 O3 Zn2 130.0(3) . 4_566 ? C8 O4 Zn1 134.3(3) . 4_566 ? C9 O5 Zn2 128.4(3) . . ? C9 O6 Zn1 136.6(3) . . ? C16 O7 Zn1 128.2(3) . 4_565 ? C16 O8 Zn2 131.6(3) . 4_565 ? O2 C1 O1 118.8(4) . . ? O2 C1 C2 121.1(4) . . ? O1 C1 C2 120.1(5) . . ? C1 C2 C3 112.4(4) . . ? C1 C2 C7 111.7(4) . . ? C3 C2 C7 110.8(4) . . ? C1 C2 H2 107.2 . . ? C3 C2 H2 107.2 . . ? C7 C2 H2 107.2 . . ? C4 C3 C2 112.8(4) . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3B 109.0 . . ? C2 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 124.1(5) . . ? C5 C4 H4 117.9 . . ? C3 C4 H4 117.9 . . ? C4 C5 C6 124.3(5) . . ? C4 C5 H5 117.9 . . ? C6 C5 H5 117.9 . . ? C5 C6 C7 113.0(4) . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 114.1(4) . . ? C8 C7 C2 110.7(4) . . ? C6 C7 C2 113.1(4) . . ? C8 C7 H7 106.1 . . ? C6 C7 H7 106.1 . . ? C2 C7 H7 106.1 . . ? O3 C8 O4 125.5(4) . . ? O3 C8 C7 116.9(4) . . ? O4 C8 C7 117.5(5) . . ? O6 C9 O5 124.7(4) . . ? O6 C9 C10 117.5(5) . . ? O5 C9 C10 117.6(4) . . ? C9 C10 C15 113.5(4) . . ? C9 C10 C11 115.3(4) . . ? C15 C10 C11 110.5(4) . . ? C9 C10 H10 105.6 . . ? C15 C10 H10 105.6 . . ? C11 C10 H10 105.6 . . ? C12 C11 C10 111.4(4) . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C13 C12 C11 124.7(5) . . ? C13 C12 H12 117.6 . . ? C11 C12 H12 117.6 . . ? C12 C13 C14 123.2(5) . . ? C12 C13 H13 118.4 . . ? C14 C13 H13 118.4 . . ? C13 C14 C15 110.9(4) . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.0 . . ? C16 C15 C14 110.6(4) . . ? C16 C15 C10 111.7(4) . . ? C14 C15 C10 110.3(4) . . ? C16 C15 H15 108.0 . . ? C14 C15 H15 108.0 . . ? C10 C15 H15 108.0 . . ? O8 C16 O7 124.4(5) . . ? O8 C16 C15 117.9(5) . . ? O7 C16 C15 117.7(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Zn1 O1 C1 93.1(3) 4_565 . . . ? O6 Zn1 O1 C1 -159.9(3) . . . . ? O7 Zn1 O1 C1 -58.4(3) 4_566 . . . ? O2 Zn1 O1 C1 1.9(2) . . . . ? O4 Zn1 O1 Zn2 -122.9(2) 4_565 . . 2_655 ? O6 Zn1 O1 Zn2 -15.8(2) . . . 2_655 ? O7 Zn1 O1 Zn2 85.6(3) 4_566 . . 2_655 ? O2 Zn1 O1 Zn2 145.9(3) . . . 2_655 ? O4 Zn1 O2 C1 -98.7(3) 4_565 . . . ? O6 Zn1 O2 C1 26.3(4) . . . . ? O7 Zn1 O2 C1 135.2(3) 4_566 . . . ? O1 Zn1 O2 C1 -2.0(3) . . . . ? O3 Zn2 O5 C9 60.7(4) 4_565 . . . ? O8 Zn2 O5 C9 -73.4(4) 4_566 . . . ? O1 Zn2 O5 C9 174.2(4) 2_645 . . . ? O4 Zn1 O6 C9 -73.8(5) 4_565 . . . ? O7 Zn1 O6 C9 59.3(5) 4_566 . . . ? O2 Zn1 O6 C9 164.8(4) . . . . ? O1 Zn1 O6 C9 -172.1(5) . . . . ? Zn1 O2 C1 O1 3.7(5) . . . . ? Zn1 O2 C1 C2 -176.2(3) . . . . ? Zn2 O1 C1 O2 -145.2(4) 2_655 . . . ? Zn1 O1 C1 O2 -2.9(4) . . . . ? Zn2 O1 C1 C2 34.7(7) 2_655 . . . ? Zn1 O1 C1 C2 176.9(4) . . . . ? O2 C1 C2 C3 -115.7(5) . . . . ? O1 C1 C2 C3 64.5(6) . . . . ? O2 C1 C2 C7 9.7(6) . . . . ? O1 C1 C2 C7 -170.2(4) . . . . ? C1 C2 C3 C4 82.3(5) . . . . ? C7 C2 C3 C4 -43.5(6) . . . . ? C2 C3 C4 C5 18.0(8) . . . . ? C3 C4 C5 C6 -0.3(11) . . . . ? C4 C5 C6 C7 9.7(9) . . . . ? C5 C6 C7 C8 -164.3(4) . . . . ? C5 C6 C7 C2 -36.5(6) . . . . ? C1 C2 C7 C8 57.2(5) . . . . ? C3 C2 C7 C8 -176.6(4) . . . . ? C1 C2 C7 C6 -72.3(5) . . . . ? C3 C2 C7 C6 53.9(5) . . . . ? Zn2 O3 C8 O4 2.3(7) 4_566 . . . ? Zn2 O3 C8 C7 179.3(3) 4_566 . . . ? Zn1 O4 C8 O3 -12.6(7) 4_566 . . . ? Zn1 O4 C8 C7 170.4(3) 4_566 . . . ? C6 C7 C8 O3 158.3(4) . . . . ? C2 C7 C8 O3 29.3(6) . . . . ? C6 C7 C8 O4 -24.5(6) . . . . ? C2 C7 C8 O4 -153.5(4) . . . . ? Zn1 O6 C9 O5 7.5(7) . . . . ? Zn1 O6 C9 C10 -168.4(3) . . . . ? Zn2 O5 C9 O6 6.2(7) . . . . ? Zn2 O5 C9 C10 -177.9(3) . . . . ? O6 C9 C10 C15 -45.2(5) . . . . ? O5 C9 C10 C15 138.6(4) . . . . ? O6 C9 C10 C11 -174.0(4) . . . . ? O5 C9 C10 C11 9.8(6) . . . . ? C9 C10 C11 C12 171.1(4) . . . . ? C15 C10 C11 C12 40.8(5) . . . . ? C10 C11 C12 C13 -9.3(8) . . . . ? C11 C12 C13 C14 -2.6(9) . . . . ? C12 C13 C14 C15 -17.8(7) . . . . ? C13 C14 C15 C16 -74.8(5) . . . . ? C13 C14 C15 C10 49.3(5) . . . . ? C9 C10 C15 C16 -70.0(5) . . . . ? C11 C10 C15 C16 61.3(5) . . . . ? C9 C10 C15 C14 166.5(4) . . . . ? C11 C10 C15 C14 -62.2(5) . . . . ? Zn2 O8 C16 O7 -32.0(7) 4_565 . . . ? Zn2 O8 C16 C15 150.6(4) 4_565 . . . ? Zn1 O7 C16 O8 -2.8(7) 4_565 . . . ? Zn1 O7 C16 C15 174.6(3) 4_565 . . . ? C14 C15 C16 O8 -24.7(6) . . . . ? C10 C15 C16 O8 -148.1(4) . . . . ? C14 C15 C16 O7 157.7(4) . . . . ? C10 C15 C16 O7 34.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 24.74 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.561 _refine_diff_density_min -0.613 _refine_diff_density_rms 0.097