Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 1350 _publ_requested_journal CrystEngComm _publ_contact_author_name 'Dr. Paul E. Kruger' _publ_contact_author_address ; Inorganic Supramolecular Chemistry Group Nasr Institute of Advanced Materials Science Department of Chemistry Trinity College Dublin. Dublin 2, Ireland ; _publ_contact_author_email Paul.Kruger@tcd.ie _publ_contact_author_phone 353-1-608-1422 _publ_contact_author_fax 353-1-671-2826 loop_ _publ_author_name 'Paul Kruger' 'Brian Conerney' 'Paul Jensen' 'Boujemaa Moubaraki' 'Keith S. Murray' _publ_section_title ; Synthesis and structural characterisation of two coordination polymers (molecular ladders) incorporating [M(OAc)2]2 secondary building units and 4,4'-bipyridine [M = Cu(II), Zn(II)] ; data_1 _database_code_CSD 219748 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety Cu(2,2'-bipy)(AcO)2 _chemical_formula_sum 'C14 H14 Cu N2 O6.50' _chemical_formula_weight 377.81 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.758(4) _cell_length_b 11.135(3) _cell_length_c 17.341(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.395(3) _cell_angle_gamma 90.00 _cell_volume 3182.7(14) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 _exptl_absorpt_coefficient_mu 1.408 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.894 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 APEX SAMRT CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14022 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 28.27 _reflns_number_total 3685 _reflns_number_gt 2901 _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 SHELXL' _computing_publication_material 'BRUKER SHELXL' _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^)+(0.0427P)^2^+22.0982P] 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 3685 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1562 _refine_ls_wR_factor_gt 0.1501 _refine_ls_goodness_of_fit_ref 1.223 _refine_ls_restrained_S_all 1.223 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 Cu1 Cu 0.09696(3) 0.11773(5) -0.19758(3) 0.01380(17) Uani 1 1 d . . . N1 N 0.1034(2) -0.0633(3) -0.1992(2) 0.0167(8) Uani 1 1 d . . . N2 N 0.1034(2) -0.7008(3) -0.1970(2) 0.0172(8) Uani 1 1 d . . . C1 C 0.1404(3) -0.1259(4) -0.2491(3) 0.0191(10) Uani 1 1 d . . . H1 H 0.1654 -0.0828 -0.2856 0.023 Uiso 1 1 calc R . . C2 C 0.1437(3) -0.2498(4) -0.2497(3) 0.0191(10) Uani 1 1 d . . . H2 H 0.1698 -0.2905 -0.2864 0.023 Uiso 1 1 calc R . . C3 C 0.1089(3) -0.3133(4) -0.1968(3) 0.0154(9) Uiso 1 1 d . . . C4 C 0.1069(3) -0.4463(4) -0.1964(3) 0.0163(10) Uani 1 1 d . . . C5 C 0.1573(3) -0.5160(4) -0.2361(3) 0.0197(10) Uani 1 1 d . . . H5 H 0.1943 -0.4776 -0.2637 0.024 Uiso 1 1 calc R . . C6 C 0.1526(3) -0.6401(4) -0.2350(3) 0.0211(11) Uani 1 1 d . . . H6 H 0.1865 -0.6845 -0.2629 0.025 Uiso 1 1 calc R . . C7 C 0.0563(3) -0.6375(4) -0.1571(3) 0.0193(10) Uani 1 1 d . . . H7 H 0.0220 -0.6793 -0.1282 0.023 Uiso 1 1 calc R . . C8 C 0.0559(3) -0.5130(4) -0.1567(3) 0.0185(10) Uani 1 1 d . . . H8 H 0.0203 -0.4719 -0.1289 0.022 Uiso 1 1 calc R . . C9 C 0.0699(3) -0.2502(4) -0.1453(3) 0.0215(11) Uani 1 1 d . . . H9 H 0.0444 -0.2914 -0.1084 0.026 Uiso 1 1 calc R . . C10 C 0.0689(3) -0.1272(4) -0.1489(3) 0.0218(10) Uani 1 1 d . . . H10 H 0.0421 -0.0848 -0.1134 0.026 Uiso 1 1 calc R . . C11 C 0.0964(3) 0.1222(4) -0.3570(3) 0.0171(9) Uani 1 1 d . . . C12 C 0.0604(3) 0.1189(6) -0.4429(3) 0.0340(13) Uani 1 1 d . . . H12A H 0.0662 0.1980 -0.4661 0.051 Uiso 1 1 calc R . . H12B H 0.0028 0.0979 -0.4496 0.051 Uiso 1 1 calc R . . H12C H 0.0889 0.0587 -0.4691 0.051 Uiso 1 1 calc R . . C13 C 0.2099(3) 0.1061(4) -0.0640(3) 0.0207(10) Uani 1 1 d . . . C14 C 0.2415(3) 0.0864(5) 0.0222(3) 0.0309(13) Uani 1 1 d . . . H14A H 0.2361 0.0013 0.0349 0.046 Uiso 1 1 calc R . . H14B H 0.2102 0.1352 0.0531 0.046 Uiso 1 1 calc R . . H14C H 0.2988 0.1096 0.0346 0.046 Uiso 1 1 calc R . . O1 O 0.04615(19) 0.1164(3) -0.30940(18) 0.0170(7) Uani 1 1 d . . . O2 O 0.1702(2) 0.1287(3) -0.3354(2) 0.0225(7) Uani 1 1 d . . . O3 O 0.1331(2) 0.1144(3) -0.08395(19) 0.0220(7) Uani 1 1 d . . . O4 O 0.2561(2) 0.1160(5) -0.1117(2) 0.0429(11) Uani 1 1 d . . . O5 O 0.2200(3) 0.3032(5) -0.4376(3) 0.0559(14) Uani 1 1 d . . . O6 O 0.4108(5) 0.1916(9) -0.0444(5) 0.044(2) Uani 0.50 1 d P . . O7 O 0.4373(6) -0.0626(11) -0.0269(6) 0.048(3) Uani 0.50 1 d P . . O8 O 0.4006(7) -0.0282(13) -0.0603(7) 0.066(4) Uani 0.50 1 d P . . 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 Cu1 0.0169(3) 0.0076(3) 0.0157(3) 0.0005(2) -0.0001(2) 0.0001(2) N1 0.020(2) 0.0092(18) 0.020(2) 0.0018(17) -0.0002(16) 0.0005(16) N2 0.017(2) 0.0132(19) 0.020(2) -0.0042(17) -0.0015(16) -0.0011(16) C1 0.022(2) 0.015(2) 0.022(2) 0.004(2) 0.0078(19) -0.0004(19) C2 0.018(2) 0.018(2) 0.023(3) -0.001(2) 0.007(2) 0.0014(18) C4 0.012(2) 0.020(2) 0.014(2) -0.0020(19) -0.0054(17) -0.0034(18) C5 0.019(2) 0.014(2) 0.027(3) -0.002(2) 0.007(2) -0.0025(18) C6 0.021(2) 0.015(3) 0.027(3) -0.004(2) 0.004(2) 0.0027(19) C7 0.023(2) 0.014(2) 0.021(2) -0.0045(19) 0.0030(19) -0.0042(18) C8 0.019(2) 0.018(3) 0.019(2) -0.0022(19) 0.005(2) -0.0007(18) C9 0.034(3) 0.010(2) 0.022(3) 0.002(2) 0.011(2) -0.002(2) C10 0.030(3) 0.015(2) 0.023(2) -0.001(2) 0.012(2) 0.003(2) C11 0.026(2) 0.007(2) 0.018(2) 0.0002(18) 0.0035(19) 0.0013(19) C12 0.034(3) 0.042(3) 0.025(3) 0.000(3) 0.004(2) -0.001(3) C13 0.022(2) 0.019(3) 0.019(2) -0.002(2) -0.0007(19) -0.003(2) C14 0.030(3) 0.038(3) 0.022(3) 0.005(2) -0.004(2) -0.004(2) O1 0.0227(17) 0.0129(16) 0.0151(16) 0.0002(13) 0.0023(13) 0.0019(14) O2 0.0237(18) 0.0184(18) 0.0259(18) 0.0016(15) 0.0055(14) 0.0019(14) O3 0.0211(17) 0.0229(18) 0.0200(17) -0.0006(15) -0.0021(14) 0.0002(15) O4 0.025(2) 0.079(3) 0.025(2) 0.005(2) 0.0038(17) -0.003(2) O5 0.065(3) 0.052(3) 0.053(3) 0.011(2) 0.017(3) -0.021(3) O6 0.021(4) 0.075(7) 0.034(5) 0.029(5) 0.000(4) -0.007(4) O7 0.033(6) 0.080(8) 0.032(6) 0.005(5) 0.010(4) 0.011(5) O8 0.043(7) 0.104(11) 0.051(8) -0.011(7) 0.012(6) 0.017(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 Cu1 O3 1.955(3) . ? Cu1 O1 1.972(3) . ? Cu1 N1 2.019(4) . ? Cu1 N2 2.024(4) 1_565 ? Cu1 O1 2.423(3) 2_554 ? N1 C10 1.335(6) . ? N1 C1 1.347(6) . ? N2 C6 1.329(6) . ? N2 C7 1.339(6) . ? N2 Cu1 2.024(4) 1_545 ? C1 C2 1.381(7) . ? C2 C3 1.371(7) . ? C3 C9 1.388(7) . ? C3 C4 1.481(6) . ? C4 C8 1.402(7) . ? C4 C5 1.415(7) . ? C5 C6 1.385(7) . ? C7 C8 1.386(7) . ? C9 C10 1.371(7) . ? C11 O2 1.228(6) . ? C11 O1 1.283(6) . ? C11 C12 1.503(7) . ? C13 O4 1.235(6) . ? C13 O3 1.274(6) . ? C13 C14 1.509(7) . ? O1 Cu1 2.423(3) 2_554 ? O7 O8 0.855(12) . ? 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 Cu1 O1 172.48(14) . . ? O3 Cu1 N1 89.28(16) . . ? O1 Cu1 N1 89.62(15) . . ? O3 Cu1 N2 90.44(16) . 1_565 ? O1 Cu1 N2 91.45(15) . 1_565 ? N1 Cu1 N2 173.80(16) . 1_565 ? O3 Cu1 O1 94.55(12) . 2_554 ? O1 Cu1 O1 78.08(13) . 2_554 ? N1 Cu1 O1 92.87(14) . 2_554 ? N2 Cu1 O1 93.32(14) 1_565 2_554 ? C10 N1 C1 116.6(4) . . ? C10 N1 Cu1 119.5(3) . . ? C1 N1 Cu1 123.9(3) . . ? C6 N2 C7 117.7(4) . . ? C6 N2 Cu1 122.8(3) . 1_545 ? C7 N2 Cu1 119.5(3) . 1_545 ? N1 C1 C2 123.1(4) . . ? C3 C2 C1 119.2(4) . . ? C2 C3 C9 118.4(4) . . ? C2 C3 C4 122.1(4) . . ? C9 C3 C4 119.3(4) . . ? C8 C4 C5 114.7(4) . . ? C8 C4 C3 123.2(5) . . ? C5 C4 C3 122.0(4) . . ? C6 C5 C4 120.0(5) . . ? N2 C6 C5 123.8(5) . . ? N2 C7 C8 122.2(5) . . ? C7 C8 C4 121.6(5) . . ? C10 C9 C3 118.7(5) . . ? N1 C10 C9 123.9(5) . . ? O2 C11 O1 123.3(4) . . ? O2 C11 C12 120.4(4) . . ? O1 C11 C12 116.4(4) . . ? O4 C13 O3 122.4(5) . . ? O4 C13 C14 121.7(5) . . ? O3 C13 C14 115.8(4) . . ? C11 O1 Cu1 114.5(3) . . ? C11 O1 Cu1 143.4(3) . 2_554 ? Cu1 O1 Cu1 101.91(13) . 2_554 ? C13 O3 Cu1 112.9(3) . . ? _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.932 _refine_diff_density_max 0.855 _refine_diff_density_min -0.494 _refine_diff_density_rms 0.118 #---END data_2 _database_code_CSD 219749 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety Zn(2,2'-bipy)(AcO)2 _chemical_formula_sum 'C14 H14 N2 O4 Zn' _chemical_formula_weight 339.64 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.942(3) _cell_length_b 9.106(3) _cell_length_c 10.593(3) _cell_angle_alpha 109.296(4) _cell_angle_beta 99.716(4) _cell_angle_gamma 101.034(4) _cell_volume 687.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 1.804 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.658 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 APEX CCD' _diffrn_measurement_method 'Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7698 _diffrn_reflns_av_R_equivalents 0.0943 _diffrn_reflns_av_sigmaI/netI 0.0933 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 28.22 _reflns_number_total 3046 _reflns_number_gt 2390 _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 SHELXL' _computing_publication_material 'BRUKER SHELXL' _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^)+(0.0747P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3046 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.1402 _refine_ls_wR_factor_gt 0.1338 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _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 -0.33340(6) -0.01928(5) -0.34930(4) 0.01717(17) Uani 1 1 d . . . O1 O -0.2377(4) 0.1568(3) -0.4144(3) 0.0238(7) Uani 1 1 d . . . O2 O -0.4042(4) 0.1150(4) -0.6221(3) 0.0254(7) Uani 1 1 d . . . O3 O -0.2792(4) -0.1682(4) -0.2332(3) 0.0280(7) Uani 1 1 d . . . O4 O -0.0493(4) -0.0079(4) -0.2475(3) 0.0330(8) Uani 1 1 d . . . N1 N -0.3479(4) 0.1740(4) -0.1668(3) 0.0185(7) Uani 1 1 d . . . N2 N -0.3271(4) 0.7938(4) 0.4616(3) 0.0163(7) Uani 1 1 d . . . C1 C -0.2432(5) 0.3240(5) -0.1243(4) 0.0241(9) Uani 1 1 d . . . H1 H -0.1674 0.3465 -0.1799 0.029 Uiso 1 1 calc R . . C2 C -0.2385(6) 0.4474(5) -0.0052(4) 0.0244(9) Uani 1 1 d . . . H2 H -0.1622 0.5517 0.0188 0.029 Uiso 1 1 calc R . . C3 C -0.3453(5) 0.4200(5) 0.0805(4) 0.0171(8) Uani 1 1 d . . . C4 C -0.3381(5) 0.5486(5) 0.2120(4) 0.0169(8) Uani 1 1 d . . . C5 C -0.2293(5) 0.7042(5) 0.2543(4) 0.0197(8) Uani 1 1 d . . . H5 H -0.1566 0.7301 0.1980 0.024 Uiso 1 1 calc R . . C6 C -0.2266(5) 0.8205(5) 0.3773(4) 0.0196(8) Uani 1 1 d . . . H6 H -0.1496 0.9252 0.4040 0.023 Uiso 1 1 calc R . . C7 C -0.4319(6) 0.6437(5) 0.4215(4) 0.0205(9) Uani 1 1 d . . . H7 H -0.5029 0.6216 0.4801 0.025 Uiso 1 1 calc R . . C8 C -0.4426(6) 0.5196(5) 0.2999(4) 0.0209(9) Uani 1 1 d . . . H8 H -0.5198 0.4157 0.2762 0.025 Uiso 1 1 calc R . . C9 C -0.4551(6) 0.2638(5) 0.0372(4) 0.0222(9) Uani 1 1 d . . . H9 H -0.5309 0.2376 0.0915 0.027 Uiso 1 1 calc R . . C10 C -0.4526(6) 0.1474(5) -0.0857(4) 0.0237(9) Uani 1 1 d . . . H10 H -0.5299 0.0425 -0.1139 0.028 Uiso 1 1 calc R . . C11 C -0.2700(5) 0.1860(5) -0.5234(4) 0.0193(8) Uani 1 1 d . . . C12 C -0.1329(6) 0.3163(6) -0.5331(5) 0.0345(11) Uani 1 1 d . . . H12A H -0.0361 0.2729 -0.5626 0.052 Uiso 1 1 calc R . . H12B H -0.0862 0.4045 -0.4425 0.052 Uiso 1 1 calc R . . H12C H -0.1862 0.3571 -0.6005 0.052 Uiso 1 1 calc R . . C13 C -0.1147(6) -0.1153(5) -0.2081(4) 0.0241(9) Uani 1 1 d . . . C14 C -0.0009(8) -0.1860(8) -0.1307(6) 0.0509(15) Uani 1 1 d . . . H14A H -0.0366 -0.1804 -0.0455 0.076 Uiso 1 1 calc R . . H14B H 0.1233 -0.1250 -0.1078 0.076 Uiso 1 1 calc R . . H14C H -0.0146 -0.2989 -0.1880 0.076 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 0.0249(3) 0.0116(3) 0.0107(2) -0.00213(17) 0.00590(17) 0.00514(18) O1 0.0368(17) 0.0145(15) 0.0160(13) 0.0021(12) 0.0090(12) 0.0023(13) O2 0.0241(15) 0.0241(16) 0.0200(14) -0.0008(12) 0.0068(12) 0.0036(12) O3 0.0303(17) 0.0246(17) 0.0222(15) 0.0014(13) 0.0081(12) 0.0033(13) O4 0.0393(18) 0.0273(18) 0.0311(17) 0.0103(14) 0.0137(14) 0.0024(15) N1 0.0237(17) 0.0112(16) 0.0158(15) -0.0017(13) 0.0083(13) 0.0032(14) N2 0.0232(17) 0.0086(16) 0.0111(14) -0.0028(12) 0.0038(12) 0.0030(13) C1 0.026(2) 0.020(2) 0.0194(19) -0.0008(17) 0.0102(16) 0.0010(18) C2 0.028(2) 0.014(2) 0.022(2) -0.0017(17) 0.0102(17) -0.0022(17) C3 0.0226(19) 0.0133(19) 0.0127(17) 0.0000(15) 0.0050(15) 0.0069(16) C4 0.021(2) 0.0128(19) 0.0147(18) 0.0017(15) 0.0043(15) 0.0062(16) C5 0.026(2) 0.012(2) 0.0178(18) 0.0004(16) 0.0100(16) 0.0032(16) C6 0.023(2) 0.013(2) 0.0175(18) -0.0011(16) 0.0078(15) 0.0029(16) C7 0.033(2) 0.013(2) 0.0166(18) 0.0032(16) 0.0135(16) 0.0058(17) C8 0.030(2) 0.0105(19) 0.0167(18) -0.0012(15) 0.0081(16) 0.0028(16) C9 0.032(2) 0.014(2) 0.0179(19) 0.0004(16) 0.0137(17) 0.0037(17) C10 0.036(2) 0.011(2) 0.0195(19) 0.0007(16) 0.0112(17) 0.0017(17) C11 0.025(2) 0.014(2) 0.0196(19) 0.0009(16) 0.0112(16) 0.0113(17) C12 0.037(3) 0.030(3) 0.035(3) 0.017(2) 0.008(2) -0.001(2) C13 0.034(2) 0.020(2) 0.0147(18) 0.0003(17) 0.0061(17) 0.0099(19) C14 0.057(4) 0.062(4) 0.039(3) 0.022(3) 0.005(3) 0.029(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 2.016(3) . ? Zn1 O2 2.028(3) 2_454 ? Zn1 O3 2.164(3) . ? Zn1 N2 2.173(3) 1_544 ? Zn1 N1 2.180(3) . ? Zn1 O4 2.298(4) . ? Zn1 C13 2.566(4) . ? O1 C11 1.264(5) . ? O2 C11 1.249(5) . ? O2 Zn1 2.028(3) 2_454 ? O3 C13 1.252(5) . ? O4 C13 1.244(5) . ? N1 C10 1.339(5) . ? N1 C1 1.339(5) . ? N2 C7 1.343(5) . ? N2 C6 1.343(5) . ? N2 Zn1 2.173(3) 1_566 ? C1 C2 1.374(6) . ? C2 C3 1.390(5) . ? C3 C9 1.397(5) . ? C3 C4 1.479(5) . ? C4 C5 1.392(5) . ? C4 C8 1.401(5) . ? C5 C6 1.374(5) . ? C7 C8 1.381(5) . ? C9 C10 1.386(5) . ? C11 C12 1.493(6) . ? C13 C14 1.492(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O2 123.35(13) . 2_454 ? O1 Zn1 O3 147.96(12) . . ? O2 Zn1 O3 88.48(12) 2_454 . ? O1 Zn1 N2 91.84(12) . 1_544 ? O2 Zn1 N2 91.73(12) 2_454 1_544 ? O3 Zn1 N2 90.62(12) . 1_544 ? O1 Zn1 N1 86.15(12) . . ? O2 Zn1 N1 87.29(11) 2_454 . ? O3 Zn1 N1 92.41(12) . . ? N2 Zn1 N1 176.79(13) 1_544 . ? O1 Zn1 O4 89.92(12) . . ? O2 Zn1 O4 146.52(13) 2_454 . ? O3 Zn1 O4 58.10(11) . . ? N2 Zn1 O4 90.68(12) 1_544 . ? N1 Zn1 O4 91.83(12) . . ? O1 Zn1 C13 118.90(13) . . ? O2 Zn1 C13 117.61(13) 2_454 . ? O3 Zn1 C13 29.13(12) . . ? N2 Zn1 C13 90.09(13) 1_544 . ? N1 Zn1 C13 93.07(13) . . ? O4 Zn1 C13 28.98(12) . . ? C11 O1 Zn1 136.8(3) . . ? C11 O2 Zn1 137.9(3) . 2_454 ? C13 O3 Zn1 93.5(3) . . ? C13 O4 Zn1 87.6(3) . . ? C10 N1 C1 116.1(3) . . ? C10 N1 Zn1 122.1(3) . . ? C1 N1 Zn1 121.7(3) . . ? C7 N2 C6 116.6(3) . . ? C7 N2 Zn1 119.9(2) . 1_566 ? C6 N2 Zn1 123.5(2) . 1_566 ? N1 C1 C2 124.0(4) . . ? C1 C2 C3 120.1(4) . . ? C2 C3 C9 116.3(3) . . ? C2 C3 C4 121.4(3) . . ? C9 C3 C4 122.2(3) . . ? C5 C4 C8 116.7(3) . . ? C5 C4 C3 122.0(3) . . ? C8 C4 C3 121.3(3) . . ? C6 C5 C4 120.3(4) . . ? N2 C6 C5 123.4(4) . . ? N2 C7 C8 123.9(4) . . ? C7 C8 C4 119.2(4) . . ? C10 C9 C3 119.5(4) . . ? N1 C10 C9 123.9(4) . . ? O2 C11 O1 125.8(4) . . ? O2 C11 C12 118.2(4) . . ? O1 C11 C12 116.0(4) . . ? O4 C13 O3 120.7(4) . . ? O4 C13 C14 121.4(4) . . ? O3 C13 C14 117.8(4) . . ? O4 C13 Zn1 63.5(2) . . ? O3 C13 Zn1 57.3(2) . . ? C14 C13 Zn1 174.5(4) . . ? _diffrn_measured_fraction_theta_max 0.897 _diffrn_reflns_theta_full 28.22 _diffrn_measured_fraction_theta_full 0.897 _refine_diff_density_max 1.250 _refine_diff_density_min -1.024 _refine_diff_density_rms 0.160