Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Zaworotko, M.' 'Bailey Walsh, Rosa D.' 'Moulton, Brian' 'Rather, Beth' _publ_contact_author_name 'Dr M Zaworotko' _publ_contact_author_address ; Department of Chemistry University of South Florida 4202 E Fowler Ave (SCA 400) Tampa Florida 33620 UNITED STATES OF AMERICA ; _publ_contact_author_email 'XTAL@USF.EDU' _publ_section_title ; A new supramolecular isomer of [Zn(nicotinate)2]n: a novel 4 2.8 4 network that is the result of self-assembly of 4-connected nodes ; data_Compound_1b _database_code_CSD 175888 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Zn(C6H4O2N)2].C10H8' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 N2 O4 Zn' _chemical_formula_weight 437.74 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 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 10.899(2) _cell_length_b 11.292(2) _cell_length_c 15.358(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.47(3) _cell_angle_gamma 90.00 _cell_volume 1858.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelpiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 1.354 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.777 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2739 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0759 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 28.26 _reflns_number_total 1692 _reflns_number_gt 1260 _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^)+(0.0352P)^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 1692 _refine_ls_number_parameters 132 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.0872 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 0.883 _refine_ls_restrained_S_all 0.883 _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 0.5000 0.45818(5) 0.2500 0.0252(2) Uani 1 2 d S . . N20 N 0.4330(3) 0.5832(2) 0.32790(18) 0.0222(7) Uani 1 1 d . . . O11 O 0.3600(2) 0.2988(2) 0.28870(16) 0.0376(7) Uani 1 1 d . . . O12 O 0.3545(2) 0.39905(19) 0.16461(15) 0.0326(6) Uani 1 1 d . . . C10 C 0.3144(3) 0.3175(3) 0.2102(3) 0.0277(9) Uani 1 1 d . . . C11 C 0.2074(3) 0.2441(3) 0.1632(2) 0.0242(8) Uani 1 1 d . . . C12 C 0.1561(3) 0.2602(3) 0.0754(2) 0.0266(9) Uani 1 1 d . . . H12 H 0.1857 0.3196 0.0427 0.032 Uiso 1 1 calc R . . C13 C 0.0593(3) 0.1868(3) 0.0360(2) 0.0295(9) Uani 1 1 d . . . H13 H 0.0235 0.1959 -0.0234 0.035 Uiso 1 1 calc R . . C21 C 0.3401(3) 0.6541(3) 0.2912(2) 0.0251(9) Uani 1 1 d . . . H21 H 0.3052 0.6425 0.2319 0.030 Uiso 1 1 calc R . . C22 C 0.4826(3) 0.5999(3) 0.4131(2) 0.0272(9) Uani 1 1 d . . . H22 H 0.5479 0.5513 0.4392 0.033 Uiso 1 1 calc R . . C100 C 0.6792(4) -0.0885(3) 0.4395(3) 0.0463(11) Uani 1 1 d . . . H100 H 0.7503 -0.1288 0.4306 0.056 Uiso 1 1 calc R . . C101 C 0.6092(4) -0.0233(3) 0.3705(3) 0.0468(12) Uani 1 1 d . . . H101 H 0.6338 -0.0213 0.3156 0.056 Uiso 1 1 calc R . . C102 C 0.5053(4) 0.0375(3) 0.3824(2) 0.0401(10) Uani 1 1 d . . . H102 H 0.4608 0.0817 0.3361 0.048 Uiso 1 1 calc R . . C103 C 0.4646(3) 0.0337(3) 0.4650(2) 0.0312(10) Uani 1 1 d . . . C104 C 0.3570(4) 0.0928(3) 0.4802(3) 0.0387(10) Uani 1 1 d . . . H104 H 0.3094 0.1358 0.4345 0.046 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 0.0244(5) 0.0192(3) 0.0317(4) 0.000 0.0045(3) 0.000 N20 0.015(2) 0.0222(14) 0.0281(17) 0.0029(12) -0.0005(16) 0.0060(12) O11 0.036(2) 0.0368(15) 0.0344(16) -0.0003(12) -0.0075(15) -0.0090(13) O12 0.0284(17) 0.0259(13) 0.0424(15) -0.0004(11) 0.0036(14) -0.0086(11) C10 0.019(3) 0.0192(17) 0.045(2) -0.0060(16) 0.006(2) -0.0025(15) C11 0.019(2) 0.0203(17) 0.032(2) -0.0019(14) 0.0013(19) -0.0011(15) C12 0.024(3) 0.0200(16) 0.038(2) 0.0003(15) 0.010(2) -0.0021(16) C13 0.030(3) 0.0301(19) 0.026(2) -0.0015(15) -0.001(2) 0.0004(17) C21 0.021(3) 0.0277(18) 0.024(2) 0.0018(14) -0.0034(19) 0.0011(16) C22 0.027(3) 0.0227(17) 0.031(2) 0.0078(15) 0.003(2) 0.0038(16) C100 0.036(3) 0.040(2) 0.062(3) -0.009(2) 0.007(3) -0.001(2) C101 0.054(3) 0.045(3) 0.042(3) 0.000(2) 0.010(3) -0.009(2) C102 0.045(3) 0.036(2) 0.033(2) 0.0045(18) -0.010(2) -0.002(2) C103 0.029(3) 0.0261(18) 0.033(2) -0.0003(15) -0.009(2) -0.0038(18) C104 0.036(3) 0.031(2) 0.042(3) 0.0004(17) -0.012(2) -0.0015(19) _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 O12 1.981(2) . ? Zn1 O12 1.981(2) 2_655 ? Zn1 N20 2.068(3) . ? Zn1 N20 2.068(3) 2_655 ? Zn1 C10 2.558(3) . ? Zn1 C10 2.558(3) 2_655 ? N20 C21 1.333(4) . ? N20 C22 1.335(4) . ? O11 C10 1.235(4) . ? O12 C10 1.281(4) . ? C10 C11 1.504(5) . ? C11 C12 1.374(4) . ? C11 C21 1.387(4) 4_545 ? C12 C13 1.391(4) . ? C13 C22 1.383(4) 4_545 ? C21 C11 1.387(4) 4 ? C22 C13 1.383(4) 4 ? C100 C104 1.362(5) 5_656 ? C100 C101 1.398(5) . ? C101 C102 1.365(5) . ? C102 C103 1.418(5) . ? C103 C104 1.406(5) . ? C103 C103 1.425(7) 5_656 ? C104 C100 1.362(5) 5_656 ? 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 O12 Zn1 O12 140.62(13) . 2_655 ? O12 Zn1 N20 106.77(10) . . ? O12 Zn1 N20 99.89(10) 2_655 . ? O12 Zn1 N20 99.89(10) . 2_655 ? O12 Zn1 N20 106.77(10) 2_655 2_655 ? N20 Zn1 N20 93.87(14) . 2_655 ? O12 Zn1 C10 29.45(10) . . ? O12 Zn1 C10 116.88(11) 2_655 . ? N20 Zn1 C10 102.42(11) . . ? N20 Zn1 C10 129.30(12) 2_655 . ? O12 Zn1 C10 116.88(11) . 2_655 ? O12 Zn1 C10 29.45(10) 2_655 2_655 ? N20 Zn1 C10 129.30(12) . 2_655 ? N20 Zn1 C10 102.42(11) 2_655 2_655 ? C10 Zn1 C10 103.18(15) . 2_655 ? C21 N20 C22 118.1(3) . . ? C21 N20 Zn1 119.1(2) . . ? C22 N20 Zn1 122.7(2) . . ? C10 O12 Zn1 101.1(2) . . ? O11 C10 O12 122.6(3) . . ? O11 C10 C11 120.9(3) . . ? O12 C10 C11 116.4(3) . . ? O11 C10 Zn1 73.3(2) . . ? O12 C10 Zn1 49.49(17) . . ? C11 C10 Zn1 165.4(2) . . ? C12 C11 C21 118.0(3) . 4_545 ? C12 C11 C10 122.7(3) . . ? C21 C11 C10 119.3(3) 4_545 . ? C11 C12 C13 119.3(3) . . ? C22 C13 C12 118.6(3) 4_545 . ? N20 C21 C11 123.4(3) . 4 ? N20 C22 C13 122.5(3) . 4 ? C104 C100 C101 119.8(4) 5_656 . ? C102 C101 C100 121.0(4) . . ? C101 C102 C103 120.5(4) . . ? C104 C103 C102 122.7(3) . . ? C104 C103 C103 118.8(4) . 5_656 ? C102 C103 C103 118.5(4) . 5_656 ? C100 C104 C103 121.4(4) 5_656 . ? _diffrn_measured_fraction_theta_max 0.732 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.732 _refine_diff_density_max 0.551 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.075 data_Compound_1c _database_code_CSD 175889 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Zn(C6H4O2N)2].2C6H5O2N' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 N4 O8 Zn' _chemical_formula_weight 555.79 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 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 11.922(3) _cell_length_b 9.990(2) _cell_length_c 20.107(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.708(4) _cell_angle_gamma 90.00 _cell_volume 2389.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 1678 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 24.81 _exptl_crystal_description square _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 1.086 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min 0.808 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 5878 _diffrn_reflns_av_R_equivalents 0.0552 _diffrn_reflns_av_sigmaI/netI 0.0714 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2099 _reflns_number_gt 1581 _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^)+(0.0377P)^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 2099 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.0977 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.0000 -0.09967(6) 0.7500 0.0247(2) Uani 1 2 d S . . N1 N 0.0777(2) 0.0391(3) 0.69063(14) 0.0253(7) Uani 1 1 d . . . O1 O -0.13503(18) -0.2669(2) 0.77005(12) 0.0330(6) Uani 1 1 d . . . O2 O -0.12515(19) -0.1431(2) 0.67985(12) 0.0332(6) Uani 1 1 d . . . C1 C -0.1716(3) -0.2336(4) 0.71276(18) 0.0271(8) Uani 1 1 d . . . C2 C 0.0370(3) 0.0733(4) 0.62931(18) 0.0310(9) Uani 1 1 d . . . H2 H -0.0284 0.0288 0.6111 0.037 Uiso 1 1 calc R . . C3 C 0.0853(3) 0.1698(4) 0.59123(19) 0.0362(10) Uani 1 1 d . . . H3 H 0.0539 0.1916 0.5480 0.043 Uiso 1 1 calc R . . C4 C 0.1817(3) 0.2344(4) 0.61812(18) 0.0323(9) Uani 1 1 d . . . H4 H 0.2174 0.3008 0.5931 0.039 Uiso 1 1 calc R . . C5 C 0.2245(3) 0.2008(3) 0.68133(17) 0.0233(8) Uani 1 1 d . . . C6 C 0.1708(2) 0.1036(4) 0.71573(16) 0.0229(7) Uani 1 1 d . . . H6 H 0.2004 0.0807 0.7592 0.027 Uiso 1 1 calc R . . N100 N 0.7849(3) 0.9119(4) 0.98508(18) 0.0465(9) Uani 1 1 d . . . O100 O 0.8547(2) 0.8277(3) 0.97204(14) 0.0540(8) Uani 1 1 d . . . O101 O 0.7889(3) 0.9746(4) 1.03747(17) 0.0807(12) Uani 1 1 d . . . C100 C 0.6912(3) 0.9381(4) 0.93545(18) 0.0319(9) Uani 1 1 d . . . C101 C 0.6856(3) 0.8679(4) 0.87686(19) 0.0341(10) Uani 1 1 d . . . H101 H 0.7391 0.8005 0.8685 0.041 Uiso 1 1 calc R . . C102 C 0.5986(3) 0.8992(4) 0.83010(19) 0.0400(10) Uani 1 1 d . . . H102 H 0.5924 0.8525 0.7889 0.048 Uiso 1 1 calc R . . C103 C 0.5214(3) 0.9966(4) 0.8427(2) 0.0372(10) Uani 1 1 d . . . H103 H 0.4628 1.0173 0.8100 0.045 Uiso 1 1 calc R . . C104 C 0.5286(3) 1.0642(4) 0.9021(2) 0.0405(11) Uani 1 1 d . . . H104 H 0.4745 1.1310 0.9106 0.049 Uiso 1 1 calc R . . C105 C 0.6140(3) 1.0357(4) 0.9498(2) 0.0445(11) Uani 1 1 d . . . H105 H 0.6195 1.0818 0.9912 0.053 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 0.0163(3) 0.0211(3) 0.0360(4) 0.000 -0.0026(2) 0.000 N1 0.0177(15) 0.0206(16) 0.0371(18) -0.0022(14) -0.0020(13) -0.0004(12) O1 0.0267(14) 0.0300(15) 0.0411(16) -0.0010(13) -0.0072(11) -0.0032(12) O2 0.0249(13) 0.0293(15) 0.0449(16) 0.0010(12) -0.0009(11) -0.0120(12) C1 0.0169(17) 0.024(2) 0.040(2) -0.0062(18) 0.0010(16) 0.0020(16) C2 0.0210(18) 0.033(2) 0.038(2) -0.0019(18) -0.0060(16) -0.0050(16) C3 0.033(2) 0.036(2) 0.038(2) 0.0070(19) -0.0094(17) -0.0078(19) C4 0.0258(19) 0.031(2) 0.040(2) 0.0020(18) -0.0002(16) -0.0069(17) C5 0.0157(17) 0.0186(19) 0.035(2) -0.0035(16) -0.0004(14) -0.0001(15) C6 0.0178(16) 0.0221(18) 0.0280(19) -0.0008(17) -0.0037(13) 0.0036(17) N100 0.040(2) 0.050(2) 0.049(2) 0.005(2) -0.0077(16) 0.0041(19) O100 0.0367(17) 0.060(2) 0.064(2) 0.0083(17) -0.0065(15) 0.0151(16) O101 0.084(2) 0.095(3) 0.059(2) -0.031(2) -0.0338(19) 0.032(2) C100 0.029(2) 0.034(2) 0.032(2) 0.0041(17) -0.0017(16) 0.0032(17) C101 0.033(2) 0.031(2) 0.039(2) 0.0053(18) 0.0070(17) 0.0064(17) C102 0.048(2) 0.037(2) 0.034(2) -0.003(2) -0.0019(18) 0.007(2) C103 0.032(2) 0.039(2) 0.040(2) 0.008(2) -0.0016(18) 0.0005(19) C104 0.032(2) 0.040(3) 0.049(3) -0.001(2) 0.0040(19) 0.0110(18) C105 0.043(2) 0.051(3) 0.040(3) -0.011(2) 0.004(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 O2 2.033(2) . ? Zn1 O2 2.033(2) 2_556 ? Zn1 N1 2.086(3) 2_556 ? Zn1 N1 2.086(3) . ? Zn1 O1 2.373(2) . ? Zn1 O1 2.373(2) 2_556 ? Zn1 C1 2.518(3) . ? Zn1 C1 2.518(3) 2_556 ? N1 C2 1.339(4) . ? N1 C6 1.352(4) . ? O1 C1 1.250(4) . ? O2 C1 1.268(4) . ? C1 C5 1.504(4) 3_445 ? C2 C3 1.380(5) . ? C3 C4 1.396(5) . ? C4 C5 1.380(4) . ? C5 C6 1.374(4) . ? C5 C1 1.504(4) 3 ? N100 O100 1.223(4) . ? N100 O101 1.224(4) . ? N100 C100 1.472(5) . ? C100 C101 1.369(5) . ? C100 C105 1.384(5) . ? C101 C102 1.390(5) . ? C102 C103 1.375(5) . ? C103 C104 1.371(5) . ? C104 C105 1.382(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 Zn1 O2 155.35(14) . 2_556 ? O2 Zn1 N1 101.87(10) . 2_556 ? O2 Zn1 N1 94.48(10) 2_556 2_556 ? O2 Zn1 N1 94.48(10) . . ? O2 Zn1 N1 101.87(10) 2_556 . ? N1 Zn1 N1 96.65(16) 2_556 . ? O2 Zn1 O1 59.46(9) . . ? O2 Zn1 O1 101.98(9) 2_556 . ? N1 Zn1 O1 92.26(10) 2_556 . ? N1 Zn1 O1 153.75(10) . . ? O2 Zn1 O1 101.98(9) . 2_556 ? O2 Zn1 O1 59.46(9) 2_556 2_556 ? N1 Zn1 O1 153.75(10) 2_556 2_556 ? N1 Zn1 O1 92.26(9) . 2_556 ? O1 Zn1 O1 90.48(12) . 2_556 ? O2 Zn1 C1 30.03(10) . . ? O2 Zn1 C1 129.71(11) 2_556 . ? N1 Zn1 C1 98.11(11) 2_556 . ? N1 Zn1 C1 124.45(11) . . ? O1 Zn1 C1 29.43(9) . . ? O1 Zn1 C1 97.04(10) 2_556 . ? O2 Zn1 C1 129.71(11) . 2_556 ? O2 Zn1 C1 30.03(10) 2_556 2_556 ? N1 Zn1 C1 124.45(11) 2_556 2_556 ? N1 Zn1 C1 98.11(11) . 2_556 ? O1 Zn1 C1 97.04(10) . 2_556 ? O1 Zn1 C1 29.43(9) 2_556 2_556 ? C1 Zn1 C1 115.80(16) . 2_556 ? C2 N1 C6 117.5(3) . . ? C2 N1 Zn1 123.2(2) . . ? C6 N1 Zn1 119.2(2) . . ? C1 O1 Zn1 81.7(2) . . ? C1 O2 Zn1 96.7(2) . . ? O1 C1 O2 122.2(3) . . ? O1 C1 C5 120.0(3) . 3_445 ? O2 C1 C5 117.8(3) . 3_445 ? O1 C1 Zn1 68.84(18) . . ? O2 C1 Zn1 53.32(16) . . ? C5 C1 Zn1 171.1(3) 3_445 . ? N1 C2 C3 123.3(3) . . ? C2 C3 C4 118.1(3) . . ? C5 C4 C3 119.4(3) . . ? C6 C5 C4 118.6(3) . . ? C6 C5 C1 119.6(3) . 3 ? C4 C5 C1 121.8(3) . 3 ? N1 C6 C5 123.1(3) . . ? O100 N100 O101 123.2(4) . . ? O100 N100 C100 118.3(4) . . ? O101 N100 C100 118.5(4) . . ? C101 C100 C105 123.0(3) . . ? C101 C100 N100 119.0(3) . . ? C105 C100 N100 118.0(4) . . ? C100 C101 C102 117.4(3) . . ? C103 C102 C101 120.9(4) . . ? C104 C103 C102 120.3(4) . . ? C103 C104 C105 120.3(4) . . ? C104 C105 C100 118.1(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.371 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.072 data_Compound_2 _database_code_CSD 175890 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Zn(C6H4O2N)2].CH4O.2H2O' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 N2 O7 Zn' _chemical_formula_weight 370.09 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 Tetragonal _symmetry_space_group_name_H-M I-42d loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' '-x+1/2, y, -z+3/4' 'x+1/2, -y, -z+3/4' '-y+1/2, -x, z+3/4' 'y+1/2, x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' '-x+1, y+1/2, -z+5/4' 'x+1, -y+1/2, -z+5/4' '-y+1, -x+1/2, z+5/4' 'y+1, x+1/2, z+5/4' _cell_length_a 21.351(3) _cell_length_b 21.351(3) _cell_length_c 6.9183(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3153.9(10) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description tetrahedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1492 _exptl_absorpt_coefficient_mu 1.593 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.777 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 4472 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0642 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.25 _reflns_number_total 1767 _reflns_number_gt 1511 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0487P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.10(3) _refine_ls_number_reflns 1767 _refine_ls_number_parameters 125 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1134 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.152 _refine_ls_shift/su_max 0.155 _refine_ls_shift/su_mean 0.019 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 0.98923(3) 0.2500 0.1250 0.0169(2) Uani 1 2 d S . . O1 O 0.78801(13) 0.01640(14) 0.1349(5) 0.0241(7) Uani 1 1 d . . . O2 O 0.82243(15) 0.07156(15) -0.1119(7) 0.0291(8) Uani 1 1 d . . . N1 N 0.9287(2) 0.1860(2) 0.2454(6) 0.0244(10) Uani 1 1 d . . . C1 C 0.9221(3) 0.1804(3) 0.4364(8) 0.0447(18) Uani 1 1 d . . . H1 H 0.9450 0.2075 0.5188 0.054 Uiso 1 1 calc R . . C2 C 0.8823(3) 0.1356(3) 0.5194(8) 0.058(2) Uani 1 1 d . . . H2 H 0.8793 0.1319 0.6559 0.070 Uiso 1 1 calc R . . C3 C 0.8478(3) 0.0974(3) 0.4023(9) 0.0402(16) Uani 1 1 d . . . H3 H 0.8198 0.0677 0.4567 0.048 Uiso 1 1 calc R . . C4 C 0.8540(3) 0.1023(2) 0.2020(7) 0.0256(12) Uani 1 1 d . . . C5 C 0.8945(2) 0.1480(2) 0.1315(11) 0.0228(10) Uani 1 1 d . . . H5 H 0.8982 0.1527 -0.0046 0.027 Uiso 1 1 calc R . . C6 C 0.8195(2) 0.0614(2) 0.0668(8) 0.0217(11) Uani 1 1 d . . . C101 C 0.7500 0.2202(6) 0.8750 0.096(4) Uani 1 2 d S . . O101 O 0.8004(10) 0.2479(11) 0.861(4) 0.086(7) Uani 0.25 1 d P . . O102 O 0.7177(14) 0.1966(14) 1.002(3) 0.115(12) Uani 0.25 1 d P . . O202 O 0.0000 0.0000 0.701(4) 0.34(2) Uani 1 2 d S . . O201 O 0.0000 0.0000 0.921(6) 0.70(2) Uani 1 2 d S . . H201 H 0.0000 0.0000 1.0915 0.835 Uiso 0.50 2 d SPR . . 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 0.0173(4) 0.0166(4) 0.0168(3) -0.0022(3) 0.000 0.000 O1 0.0238(18) 0.0265(17) 0.0221(16) -0.0007(17) -0.0031(17) -0.0087(14) O2 0.034(2) 0.0310(19) 0.0227(18) -0.0006(19) -0.002(2) -0.0102(16) N1 0.025(3) 0.031(3) 0.018(2) -0.0052(18) 0.0005(17) -0.007(2) C1 0.056(4) 0.057(5) 0.021(3) -0.004(3) -0.004(3) -0.033(4) C2 0.090(6) 0.079(6) 0.005(3) -0.005(3) 0.001(3) -0.052(5) C3 0.058(4) 0.045(4) 0.018(3) 0.004(3) 0.005(3) -0.035(3) C4 0.026(3) 0.029(3) 0.022(2) -0.002(2) 0.000(2) -0.010(2) C5 0.026(3) 0.025(3) 0.018(2) 0.006(3) 0.002(3) -0.0047(19) C6 0.016(3) 0.023(3) 0.026(2) -0.0070(19) -0.0009(18) 0.001(2) C101 0.088(10) 0.075(9) 0.126(13) 0.000 0.037(12) 0.000 O101 0.094(16) 0.060(13) 0.105(17) 0.04(2) -0.023(16) -0.033(14) O102 0.11(2) 0.17(3) 0.066(17) 0.025(18) 0.053(14) 0.06(2) O202 0.212(18) 0.102(12) 0.70(6) 0.000 0.000 0.000(18) O201 0.49(2) 1.12(5) 0.48(6) 0.000 0.000 -0.677 _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 2.056(3) 3_665 ? Zn1 O1 2.056(3) 16_544 ? Zn1 N1 2.057(4) . ? Zn1 N1 2.057(4) 14_454 ? Zn1 O2 2.343(3) 16_544 ? Zn1 O2 2.343(3) 3_665 ? Zn1 C6 2.518(5) 16_544 ? Zn1 C6 2.518(5) 3_665 ? O1 C6 1.264(6) . ? O1 Zn1 2.056(3) 4_645 ? O2 C6 1.257(7) . ? O2 Zn1 2.343(3) 4_645 ? N1 C1 1.334(7) . ? N1 C5 1.346(7) . ? C1 C2 1.402(8) . ? C2 C3 1.364(8) . ? C3 C4 1.396(8) . ? C4 C5 1.392(7) . ? C4 C6 1.477(7) . ? C6 Zn1 2.518(5) 4_645 ? C101 O102 1.23(2) 5_656 ? C101 O102 1.23(2) . ? C101 O101 1.232(18) . ? C101 O101 1.232(18) 5_656 ? O101 O102 1.40(3) 5_656 ? O102 O101 1.40(3) 5_656 ? O202 O201 1.53(5) . ? O201 O201 1.09(9) 3_557 ? 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 O1 147.23(17) 3_665 16_544 ? O1 Zn1 N1 105.63(15) 3_665 . ? O1 Zn1 N1 94.88(14) 16_544 . ? O1 Zn1 N1 94.88(14) 3_665 14_454 ? O1 Zn1 N1 105.63(15) 16_544 14_454 ? N1 Zn1 N1 102.1(3) . 14_454 ? O1 Zn1 O2 94.73(14) 3_665 16_544 ? O1 Zn1 O2 59.62(15) 16_544 16_544 ? N1 Zn1 O2 153.41(17) . 16_544 ? N1 Zn1 O2 92.80(17) 14_454 16_544 ? O1 Zn1 O2 59.62(15) 3_665 3_665 ? O1 Zn1 O2 94.73(14) 16_544 3_665 ? N1 Zn1 O2 92.80(17) . 3_665 ? N1 Zn1 O2 153.41(17) 14_454 3_665 ? O2 Zn1 O2 82.77(16) 16_544 3_665 ? O1 Zn1 C6 121.40(15) 3_665 16_544 ? O1 Zn1 C6 29.98(15) 16_544 16_544 ? N1 Zn1 C6 124.24(18) . 16_544 ? N1 Zn1 C6 101.92(17) 14_454 16_544 ? O2 Zn1 C6 29.70(17) 16_544 16_544 ? O2 Zn1 C6 87.15(15) 3_665 16_544 ? O1 Zn1 C6 29.98(15) 3_665 3_665 ? O1 Zn1 C6 121.40(15) 16_544 3_665 ? N1 Zn1 C6 101.92(17) . 3_665 ? N1 Zn1 C6 124.24(18) 14_454 3_665 ? O2 Zn1 C6 87.15(15) 16_544 3_665 ? O2 Zn1 C6 29.70(17) 3_665 3_665 ? C6 Zn1 C6 104.5(2) 16_544 3_665 ? C6 O1 Zn1 95.6(3) . 4_645 ? C6 O2 Zn1 82.9(3) . 4_645 ? C1 N1 C5 117.9(5) . . ? C1 N1 Zn1 121.8(4) . . ? C5 N1 Zn1 120.2(4) . . ? N1 C1 C2 122.1(5) . . ? C3 C2 C1 119.4(6) . . ? C2 C3 C4 119.6(5) . . ? C5 C4 C3 117.3(5) . . ? C5 C4 C6 120.2(5) . . ? C3 C4 C6 122.5(5) . . ? N1 C5 C4 123.6(6) . . ? O2 C6 O1 121.6(5) . . ? O2 C6 C4 119.7(5) . . ? O1 C6 C4 118.6(5) . . ? O2 C6 Zn1 67.4(3) . 4_645 ? O1 C6 Zn1 54.4(3) . 4_645 ? C4 C6 Zn1 171.9(4) . 4_645 ? O102 C101 O102 131(3) 5_656 . ? O102 C101 O101 69.5(16) 5_656 . ? O102 C101 O101 138.1(18) . . ? O102 C101 O101 138.1(18) 5_656 5_656 ? O102 C101 O101 69.5(16) . 5_656 ? O101 C101 O101 123(3) . 5_656 ? C101 O101 O102 55.1(13) . 5_656 ? C101 O102 O101 55.3(14) . 5_656 ? O201 O201 O202 180.000(17) 3_557 . ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.538 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.087