# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 903982' #TrackingRef 'web_deposit_cif_file_0_BoLiu_1349151727.1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum C13H7NO4Zn _chemical_formula_weight 306.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P43212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 13.4641(2) _cell_length_b 13.4641(2) _cell_length_c 23.3751(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4237.48(11) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9035 _cell_measurement_theta_min 3.789 _cell_measurement_theta_max 58.967 _exptl_crystal_description polyhedral _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.961 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 1.671 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7100 _exptl_absorpt_correction_T_max 0.7643 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12088 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.79 _diffrn_reflns_theta_max 59.08 _reflns_number_total 2969 _reflns_number_gt 2913 _reflns_threshold_expression >2sigma(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^)+(0.1390P)^2^+17.0919P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.33(10) _refine_ls_number_reflns 2969 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0736 _refine_ls_wR_factor_ref 0.2402 _refine_ls_wR_factor_gt 0.2395 _refine_ls_goodness_of_fit_ref 1.226 _refine_ls_restrained_S_all 1.226 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.004 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 0.85790(7) 0.79571(8) 0.05864(4) 0.0203(4) Uani 1 1 d . . . O1 O 1.2062(4) 0.7122(5) 0.1758(3) 0.0374(15) Uani 1 1 d . . . O2 O 1.1659(4) 0.6597(6) 0.2633(3) 0.0414(17) Uani 1 1 d . . . O3 O 0.4903(4) 0.6868(5) 0.2308(3) 0.0385(16) Uani 1 1 d . . . O4 O 0.4444(5) 0.6535(6) 0.3197(3) 0.0420(16) Uani 1 1 d . . . C1 C 1.1451(6) 0.6910(6) 0.2146(4) 0.0260(18) Uani 1 1 d . . . C2 C 1.0368(6) 0.7053(7) 0.2019(3) 0.0279(19) Uani 1 1 d . . . C3 C 0.9669(6) 0.6904(8) 0.2442(4) 0.035(2) Uani 1 1 d . . . H3 H 0.9869 0.6681 0.2801 0.043 Uiso 1 1 calc R . . C4 C 0.8667(7) 0.7083(8) 0.2337(4) 0.039(2) Uani 1 1 d . . . C5 C 0.8422(7) 0.7392(7) 0.1781(4) 0.035(2) Uani 1 1 d . . . H5 H 0.7760 0.7526 0.1698 0.042 Uiso 1 1 calc R . . C6 C 1.0057(6) 0.7348(6) 0.1486(3) 0.0209(18) Uani 1 1 d . . . H6 H 1.0527 0.7442 0.1199 0.025 Uiso 1 1 calc R . . C7 C 0.7879(7) 0.6963(10) 0.2773(4) 0.046(3) Uani 1 1 d . . . C8 C 0.6884(7) 0.6877(8) 0.2615(4) 0.040(2) Uani 1 1 d . . . H8 H 0.6722 0.6876 0.2229 0.048 Uiso 1 1 calc R . . C9 C 0.6125(7) 0.6792(9) 0.3018(4) 0.042(2) Uani 1 1 d . . . C10 C 0.6389(9) 0.6793(13) 0.3584(5) 0.076(5) Uani 1 1 d . . . H10 H 0.5896 0.6721 0.3860 0.092 Uiso 1 1 calc R . . C11 C 0.7351(10) 0.6897(18) 0.3755(6) 0.117(9) Uani 1 1 d . . . H11 H 0.7504 0.6896 0.4143 0.140 Uiso 1 1 calc R . . C12 C 0.8106(9) 0.7005(16) 0.3353(5) 0.096(6) Uani 1 1 d . . . H12 H 0.8758 0.7105 0.3472 0.115 Uiso 1 1 calc R . . C13 C 0.5087(7) 0.6719(7) 0.2828(4) 0.035(2) Uani 1 1 d . . . N1 N 0.9093(5) 0.7503(5) 0.1366(3) 0.0251(16) 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 0.0176(6) 0.0216(6) 0.0218(6) 0.0026(5) -0.0024(4) -0.0007(4) O1 0.016(3) 0.060(4) 0.036(3) 0.010(3) -0.001(3) 0.000(3) O2 0.024(3) 0.067(5) 0.033(4) 0.015(3) -0.005(3) 0.004(3) O3 0.025(3) 0.057(4) 0.034(4) 0.007(3) 0.002(3) 0.003(3) O4 0.028(3) 0.062(5) 0.036(4) 0.002(3) 0.007(3) -0.002(3) C1 0.022(4) 0.026(4) 0.031(5) 0.000(4) 0.002(4) 0.003(4) C2 0.021(4) 0.036(5) 0.027(4) 0.005(4) 0.003(3) -0.003(4) C3 0.020(5) 0.057(6) 0.030(4) 0.011(4) -0.006(4) 0.003(4) C4 0.019(5) 0.065(7) 0.032(5) 0.002(5) 0.001(4) -0.001(5) C5 0.020(4) 0.054(6) 0.031(5) 0.010(4) 0.000(4) -0.001(4) C6 0.011(4) 0.023(4) 0.029(4) 0.006(3) 0.003(3) 0.001(3) C7 0.021(5) 0.089(8) 0.028(5) 0.007(5) -0.002(4) -0.002(5) C8 0.032(5) 0.060(6) 0.028(4) 0.008(4) 0.006(4) -0.001(5) C9 0.021(5) 0.072(7) 0.034(5) 0.006(5) 0.002(4) 0.005(4) C10 0.032(6) 0.162(15) 0.036(6) 0.008(7) 0.006(5) -0.018(8) C11 0.041(8) 0.27(3) 0.034(6) 0.029(11) -0.003(5) -0.019(11) C12 0.025(6) 0.23(2) 0.037(6) 0.010(10) -0.006(5) 0.000(9) C13 0.034(5) 0.042(6) 0.028(5) -0.001(4) 0.003(4) 0.007(4) N1 0.020(4) 0.028(4) 0.028(4) 0.005(3) -0.002(3) -0.002(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 O3 2.022(6) 6_565 ? Zn1 O4 2.024(6) 3_654 ? Zn1 N1 2.043(7) . ? Zn1 O2 2.058(6) 3_644 ? Zn1 O1 2.078(6) 6_465 ? Zn1 Zn1 2.9864(19) 7 ? O1 C1 1.257(10) . ? O1 Zn1 2.078(6) 6_565 ? O2 C1 1.246(11) . ? O2 Zn1 2.058(6) 4_565 ? O3 C13 1.256(11) . ? O3 Zn1 2.022(6) 6_465 ? O4 C13 1.247(11) . ? O4 Zn1 2.024(6) 4_465 ? C1 C2 1.500(12) . ? C2 C3 1.380(12) . ? C2 C6 1.374(12) . ? C3 C4 1.392(13) . ? C3 H3 0.9300 . ? C4 C5 1.405(13) . ? C4 C7 1.480(13) . ? C5 N1 1.333(11) . ? C5 H5 0.9300 . ? C6 N1 1.345(11) . ? C6 H6 0.9300 . ? C7 C12 1.392(15) . ? C7 C8 1.394(14) . ? C8 C9 1.395(13) . ? C8 H8 0.9300 . ? C9 C10 1.370(16) . ? C9 C13 1.470(13) . ? C10 C11 1.362(18) . ? C10 H10 0.9300 . ? C11 C12 1.392(18) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 O4 90.6(3) 6_565 3_654 ? O3 Zn1 N1 98.3(3) 6_565 . ? O4 Zn1 N1 102.0(3) 3_654 . ? O3 Zn1 O2 88.0(3) 6_565 3_644 ? O4 Zn1 O2 153.8(3) 3_654 3_644 ? N1 Zn1 O2 104.1(3) . 3_644 ? O3 Zn1 O1 162.4(2) 6_565 6_465 ? O4 Zn1 O1 87.3(3) 3_654 6_465 ? N1 Zn1 O1 99.3(3) . 6_465 ? O2 Zn1 O1 86.2(3) 3_644 6_465 ? O3 Zn1 Zn1 78.21(17) 6_565 7 ? O4 Zn1 Zn1 79.57(18) 3_654 7 ? N1 Zn1 Zn1 176.2(2) . 7 ? O2 Zn1 Zn1 74.53(18) 3_644 7 ? O1 Zn1 Zn1 84.24(16) 6_465 7 ? C1 O1 Zn1 120.3(5) . 6_565 ? C1 O2 Zn1 134.4(6) . 4_565 ? C13 O3 Zn1 129.3(6) . 6_465 ? C13 O4 Zn1 127.8(6) . 4_465 ? O2 C1 O1 126.2(8) . . ? O2 C1 C2 116.2(7) . . ? O1 C1 C2 117.6(7) . . ? C3 C2 C6 119.0(8) . . ? C3 C2 C1 120.2(7) . . ? C6 C2 C1 120.8(7) . . ? C2 C3 C4 120.6(8) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 116.3(8) . . ? C3 C4 C7 123.7(8) . . ? C5 C4 C7 120.1(8) . . ? N1 C5 C4 123.2(8) . . ? N1 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? N1 C6 C2 121.9(7) . . ? N1 C6 H6 119.0 . . ? C2 C6 H6 119.1 . . ? C12 C7 C8 118.2(9) . . ? C12 C7 C4 120.6(10) . . ? C8 C7 C4 121.1(8) . . ? C9 C8 C7 122.2(9) . . ? C9 C8 H8 118.9 . . ? C7 C8 H8 118.9 . . ? C10 C9 C8 117.5(9) . . ? C10 C9 C13 122.6(9) . . ? C8 C9 C13 119.9(9) . . ? C11 C10 C9 122.0(11) . . ? C11 C10 H10 119.0 . . ? C9 C10 H10 119.0 . . ? C10 C11 C12 120.5(12) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C7 119.5(11) . . ? C11 C12 H12 120.2 . . ? C7 C12 H12 120.2 . . ? O4 C13 O3 124.3(9) . . ? O4 C13 C9 117.7(8) . . ? O3 C13 C9 118.0(8) . . ? C5 N1 C6 119.0(7) . . ? C5 N1 Zn1 116.9(6) . . ? C6 N1 Zn1 124.0(6) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 59.08 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.119 _refine_diff_density_min -0.561 _refine_diff_density_rms 0.245