# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof. Danil Dybtsev' _publ_contact_author_email danil@postech.ac.kr _publ_section_title ; Enantioselective Sorption of Alcohols in a Homochiral Metal-Organic Framework ; loop_ _publ_author_name K.Suh M.Yutkin D.Dybtsev V.Fedin K.Kim # Attachment '1-R-PhEtOH.cif' data_p212121a _database_code_depnum_ccdc_archive 'CCDC 847107' #TrackingRef '1-R-PhEtOH.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 N O8 Zn2 C8 H10 O' _chemical_formula_sum 'C22 H25 N O9 Zn2' _chemical_formula_weight 578.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.334(2) _cell_length_b 11.672(2) _cell_length_c 20.341(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2453.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5039 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 30.34 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 2.005 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'HKL2000 Scalepack' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.80000 _diffrn_radiation_type 'Synchrotron at Pohang Accelerator Laboratory' _diffrn_radiation_source 'bending mangnet 6B MX Beamline' _diffrn_radiation_monochromator 'Si(111) double crystal monochromator' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16254 _diffrn_reflns_av_R_equivalents 0.0939 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 30.34 _reflns_number_total 5039 _reflns_number_gt 5014 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ADSC Qunatum-210 ADX Program' _computing_cell_refinement HKL2000 _computing_data_reduction HKL2000 _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.058(11) _refine_ls_number_reflns 5039 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1327 _refine_ls_wR_factor_gt 0.1324 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _refine_ls_shift/su_max 0.057 _refine_ls_shift/su_mean 0.014 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 0.84731(3) 0.32513(3) -0.011465(19) 0.01001(13) Uani 1 1 d . . . Zn2 Zn 0.53438(3) 0.41947(3) -0.007170(19) 0.00957(13) Uani 1 1 d . . . O1B O 0.8234(2) 0.4171(2) 0.07101(11) 0.0172(5) Uani 1 1 d . . . O2B O 0.6091(2) 0.4462(2) 0.08297(11) 0.0201(5) Uani 1 1 d . . . O3B O 0.9052(2) 0.5399(2) 0.40334(12) 0.0189(5) Uani 1 1 d . . . O4B O 0.6944(2) 0.5838(2) 0.40903(12) 0.0219(5) Uani 1 1 d . . . C1B C 0.7237(3) 0.4436(3) 0.10387(15) 0.0131(6) Uani 1 1 d . . . C2B C 0.7439(3) 0.4758(3) 0.17451(16) 0.0146(6) Uani 1 1 d . . . C3B C 0.8663(3) 0.4648(3) 0.20312(17) 0.0195(7) Uani 1 1 d . . . H3BA H 0.9359 0.4393 0.1781 0.023 Uiso 1 1 calc R . . C4B C 0.6405(3) 0.5173(3) 0.21160(17) 0.0172(6) Uani 1 1 d . . . H4BA H 0.5600 0.5281 0.1920 0.021 Uiso 1 1 calc R . . C5B C 0.8839(3) 0.4921(3) 0.26940(16) 0.0197(7) Uani 1 1 d . . . H5BA H 0.9652 0.4854 0.2886 0.024 Uiso 1 1 calc R . . C6B C 0.6576(3) 0.5424(3) 0.27736(17) 0.0171(6) Uani 1 1 d . . . H6BA H 0.5881 0.5680 0.3024 0.020 Uiso 1 1 calc R . . C7B C 0.7790(3) 0.5293(3) 0.30636(16) 0.0141(6) Uani 1 1 d . . . C8B C 0.7948(3) 0.5541(3) 0.37917(15) 0.0119(6) Uani 1 1 d . . . O1L O 0.6496(2) 0.26876(19) -0.00984(12) 0.0136(4) Uani 1 1 d . . . O2L O 0.5313(2) 0.1197(2) 0.02414(13) 0.0190(5) Uani 1 1 d . . . O3L O 0.8707(2) 0.16134(17) 0.00579(12) 0.0120(4) Uani 1 1 d . . . C1L C 0.6375(3) 0.1688(3) 0.01257(14) 0.0111(6) Uani 1 1 d . . . C2L C 0.7600(3) 0.1049(3) 0.03165(17) 0.0159(6) Uani 1 1 d . . . H2LA H 0.7559 0.0277 0.0128 0.019 Uiso 1 1 calc R . . C3L C 0.7664(3) 0.0942(3) 0.10628(18) 0.0238(7) Uani 1 1 d . . . H3LA H 0.8433 0.0533 0.1184 0.036 Uiso 1 1 calc R . . H3LB H 0.6918 0.0533 0.1218 0.036 Uiso 1 1 calc R . . H3LC H 0.7681 0.1692 0.1256 0.036 Uiso 1 1 calc R . . O1D O 0.4555(2) 0.58719(19) -0.00177(12) 0.0201(5) Uani 1 1 d . . . N1D N 0.4403(3) 0.7655(2) 0.04140(17) 0.0267(7) Uani 1 1 d . . . C1D C 0.4846(3) 0.6611(3) 0.03948(17) 0.0195(6) Uani 1 1 d . . . H1DA H 0.5433 0.6400 0.0720 0.023 Uiso 1 1 calc R . . C2D C 0.4802(5) 0.8470(4) 0.0935(2) 0.0407(10) Uani 1 1 d . . . H2DA H 0.5453 0.8122 0.1206 0.061 Uiso 1 1 calc R . . H2DB H 0.4066 0.8666 0.1200 0.061 Uiso 1 1 calc R . . H2DC H 0.5146 0.9151 0.0736 0.061 Uiso 1 1 calc R . . C3D C 0.3409(4) 0.8036(4) -0.0053(3) 0.0421(11) Uani 1 1 d . . . H3DA H 0.3239 0.7437 -0.0364 0.063 Uiso 1 1 calc R . . H3DB H 0.3709 0.8706 -0.0281 0.063 Uiso 1 1 calc R . . H3DC H 0.2628 0.8216 0.0182 0.063 Uiso 1 1 calc R . . O1R O 0.8906(4) 0.1796(3) -0.17282(18) 0.0493(9) Uani 1 1 d . . . H1RA H 0.9441 0.1436 -0.1513 0.074 Uiso 1 1 calc R . . C1R C 0.7742(4) -0.0011(3) -0.1882(2) 0.0290(8) Uani 1 1 d . . . C2R C 0.7909(4) -0.1075(4) -0.2176(2) 0.0318(8) Uani 1 1 d . . . H2RA H 0.8424 -0.1142 -0.2549 0.038 Uiso 1 1 calc R . . C3R C 0.7315(5) -0.2027(4) -0.1919(3) 0.0466(12) Uani 1 1 d . . . H3RA H 0.7438 -0.2739 -0.2115 0.056 Uiso 1 1 calc R . . C4R C 0.6529(5) -0.1929(5) -0.1366(3) 0.0491(13) Uani 1 1 d . . . H4RA H 0.6099 -0.2568 -0.1203 0.059 Uiso 1 1 calc R . . C5R C 0.6390(5) -0.0878(5) -0.1061(3) 0.0508(12) Uani 1 1 d . . . H5RA H 0.5891 -0.0813 -0.0683 0.061 Uiso 1 1 calc R . . C6R C 0.6997(5) 0.0078(4) -0.1320(2) 0.0390(10) Uani 1 1 d . . . H6RA H 0.6902 0.0786 -0.1115 0.047 Uiso 1 1 calc R . . C7R C 0.8321(5) 0.1051(4) -0.2203(2) 0.0346(9) Uani 1 1 d . . . H7RA H 0.8982 0.0811 -0.2520 0.042 Uiso 1 1 calc R . . C8R C 0.7321(5) 0.1748(4) -0.2555(3) 0.0401(10) Uani 1 1 d . . . H8RA H 0.7727 0.2400 -0.2756 0.060 Uiso 1 1 calc R . . H8RB H 0.6679 0.2003 -0.2248 0.060 Uiso 1 1 calc R . . H8RC H 0.6917 0.1288 -0.2888 0.060 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 0.0034(2) 0.0152(2) 0.0115(2) 0.00049(12) 0.00061(12) -0.00024(11) Zn2 0.00348(19) 0.0154(2) 0.00979(19) -0.00015(12) -0.00011(11) -0.00058(11) O1B 0.0135(11) 0.0256(11) 0.0125(10) -0.0060(9) 0.0019(8) -0.0044(10) O2B 0.0180(12) 0.0273(12) 0.0150(11) -0.0067(9) -0.0053(10) 0.0090(10) O3B 0.0164(11) 0.0248(11) 0.0155(12) -0.0057(9) -0.0073(9) 0.0033(10) O4B 0.0095(10) 0.0394(13) 0.0169(12) -0.0088(11) 0.0056(9) -0.0059(10) C1B 0.0133(14) 0.0154(13) 0.0107(14) -0.0015(10) -0.0020(12) 0.0029(11) C2B 0.0133(14) 0.0187(13) 0.0118(15) -0.0020(11) -0.0015(12) 0.0013(12) C3B 0.0100(14) 0.0325(16) 0.0160(15) -0.0060(13) 0.0008(12) 0.0034(12) C4B 0.0088(12) 0.0310(17) 0.0119(14) -0.0012(13) -0.0040(12) -0.0030(13) C5B 0.0077(13) 0.0326(17) 0.0189(17) -0.0036(13) 0.0001(12) 0.0054(14) C6B 0.0061(13) 0.0294(16) 0.0157(16) -0.0058(12) 0.0008(12) 0.0027(12) C7B 0.0107(14) 0.0205(13) 0.0112(15) -0.0024(11) 0.0008(11) -0.0006(12) C8B 0.0100(13) 0.0163(13) 0.0095(14) -0.0019(10) 0.0030(11) -0.0066(11) O1L 0.0035(9) 0.0185(10) 0.0189(11) 0.0007(9) 0.0011(9) -0.0016(8) O2L 0.0046(11) 0.0201(10) 0.0323(14) 0.0046(10) -0.0005(10) -0.0004(8) O3L 0.0048(10) 0.0124(9) 0.0188(11) 0.0011(8) 0.0040(9) -0.0021(8) C1L 0.0019(13) 0.0217(14) 0.0097(14) 0.0030(11) 0.0008(9) -0.0014(10) C2L 0.0052(14) 0.0212(13) 0.0213(16) 0.0063(12) 0.0051(12) -0.0050(11) C3L 0.0087(15) 0.0389(19) 0.0239(17) 0.0123(15) 0.0024(12) 0.0005(14) O1D 0.0170(12) 0.0142(11) 0.0292(14) -0.0004(9) -0.0029(10) 0.0024(8) N1D 0.0258(16) 0.0170(13) 0.0373(17) -0.0010(12) 0.0010(14) 0.0011(12) C1D 0.0174(16) 0.0158(13) 0.0253(17) 0.0026(12) 0.0009(13) 0.0053(13) C2D 0.050(3) 0.0243(18) 0.048(3) -0.0068(17) 0.002(2) -0.0038(19) C3D 0.031(2) 0.0322(18) 0.064(3) 0.012(2) 0.000(2) 0.0144(17) O1R 0.058(2) 0.0366(16) 0.054(2) -0.0062(14) -0.0246(18) -0.0101(16) C1R 0.0278(18) 0.0304(18) 0.029(2) -0.0026(14) -0.0068(16) 0.0007(16) C2R 0.030(2) 0.0350(17) 0.030(2) -0.0081(16) 0.0005(18) -0.0013(18) C3R 0.054(3) 0.040(2) 0.046(3) 0.004(2) -0.008(3) -0.011(2) C4R 0.038(3) 0.056(3) 0.052(3) 0.014(2) -0.008(2) -0.017(2) C5R 0.032(2) 0.068(3) 0.053(3) 0.005(3) 0.007(2) -0.006(2) C6R 0.036(2) 0.045(2) 0.036(3) -0.0009(18) 0.0001(18) 0.003(2) C7R 0.034(2) 0.0378(19) 0.032(2) -0.0055(17) -0.0077(19) -0.0011(18) C8R 0.039(2) 0.035(2) 0.047(3) 0.001(2) -0.014(2) 0.001(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 O3L 1.959(2) . ? Zn1 O4B 1.982(2) 2_664 ? Zn1 O1B 2.007(2) . ? Zn1 O2L 2.024(2) 4 ? Zn1 O1L 2.147(2) . ? Zn2 O3L 1.937(2) 4_455 ? Zn2 O3B 1.982(2) 2_664 ? Zn2 O2B 2.014(2) . ? Zn2 O1L 2.125(2) . ? Zn2 O1D 2.123(2) . ? O1B C1B 1.266(4) . ? O2B C1B 1.259(4) . ? O3B C8B 1.254(4) . ? O3B Zn2 1.982(2) 2_665 ? O4B C8B 1.251(4) . ? O4B Zn1 1.982(2) 2_665 ? C1B C2B 1.500(4) . ? C2B C4B 1.395(5) . ? C2B C3B 1.398(4) . ? C3B C5B 1.397(5) . ? C4B C6B 1.381(5) . ? C5B C7B 1.389(4) . ? C6B C7B 1.394(4) . ? C7B C8B 1.518(4) . ? O1L C1L 1.259(4) . ? O2L C1L 1.260(4) . ? O2L Zn1 2.024(2) 4_455 ? O3L C2L 1.422(4) . ? O3L Zn2 1.937(2) 4 ? C1L C2L 1.520(4) . ? C2L C3L 1.525(5) . ? O1D C1D 1.240(4) . ? N1D C1D 1.303(4) . ? N1D C3D 1.468(6) . ? N1D C2D 1.482(5) . ? O1R C7R 1.433(5) . ? C1R C6R 1.382(7) . ? C1R C2R 1.389(6) . ? C1R C7R 1.524(6) . ? C2R C3R 1.373(6) . ? C3R C4R 1.392(8) . ? C4R C5R 1.382(9) . ? C5R C6R 1.385(7) . ? C7R C8R 1.497(6) . ? 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 O3L Zn1 O4B 134.12(11) . 2_664 ? O3L Zn1 O1B 112.80(10) . . ? O4B Zn1 O1B 111.62(11) 2_664 . ? O3L Zn1 O2L 102.55(9) . 4 ? O4B Zn1 O2L 85.96(10) 2_664 4 ? O1B Zn1 O2L 92.98(10) . 4 ? O3L Zn1 O1L 79.38(9) . . ? O4B Zn1 O1L 88.29(9) 2_664 . ? O1B Zn1 O1L 91.94(9) . . ? O2L Zn1 O1L 173.51(10) 4 . ? O3L Zn2 O3B 113.87(10) 4_455 2_664 ? O3L Zn2 O2B 113.39(10) 4_455 . ? O3B Zn2 O2B 132.74(10) 2_664 . ? O3L Zn2 O1L 94.95(9) 4_455 . ? O3B Zn2 O1L 89.88(9) 2_664 . ? O2B Zn2 O1L 86.36(10) . . ? O3L Zn2 O1D 96.50(9) 4_455 . ? O3B Zn2 O1D 87.02(9) 2_664 . ? O2B Zn2 O1D 87.56(9) . . ? O1L Zn2 O1D 168.43(9) . . ? C1B O1B Zn1 132.2(2) . . ? C1B O2B Zn2 131.7(2) . . ? C8B O3B Zn2 128.0(2) . 2_665 ? C8B O4B Zn1 136.4(2) . 2_665 ? O1B C1B O2B 126.4(3) . . ? O1B C1B C2B 117.0(3) . . ? O2B C1B C2B 116.7(3) . . ? C4B C2B C3B 120.0(3) . . ? C4B C2B C1B 119.9(3) . . ? C3B C2B C1B 120.1(3) . . ? C5B C3B C2B 119.9(3) . . ? C6B C4B C2B 119.9(3) . . ? C3B C5B C7B 119.5(3) . . ? C4B C6B C7B 120.2(3) . . ? C5B C7B C6B 120.5(3) . . ? C5B C7B C8B 120.3(3) . . ? C6B C7B C8B 119.2(3) . . ? O3B C8B O4B 126.9(3) . . ? O3B C8B C7B 117.1(3) . . ? O4B C8B C7B 116.0(3) . . ? C1L O1L Zn2 134.62(19) . . ? C1L O1L Zn1 112.60(19) . . ? Zn2 O1L Zn1 106.25(10) . . ? C1L O2L Zn1 130.5(2) . 4_455 ? C2L O3L Zn2 118.15(19) . 4 ? C2L O3L Zn1 114.80(19) . . ? Zn2 O3L Zn1 125.87(11) 4 . ? O1L C1L O2L 125.2(3) . . ? O1L C1L C2L 117.7(3) . . ? O2L C1L C2L 117.0(3) . . ? O3L C2L C1L 110.4(2) . . ? O3L C2L C3L 111.8(3) . . ? C1L C2L C3L 109.3(3) . . ? C1D O1D Zn2 125.7(2) . . ? C1D N1D C3D 120.7(4) . . ? C1D N1D C2D 121.6(4) . . ? C3D N1D C2D 117.5(4) . . ? O1D C1D N1D 125.9(3) . . ? C6R C1R C2R 119.5(4) . . ? C6R C1R C7R 120.8(4) . . ? C2R C1R C7R 119.6(4) . . ? C3R C2R C1R 120.3(4) . . ? C4R C3R C2R 120.1(5) . . ? C3R C4R C5R 119.8(5) . . ? C4R C5R C6R 119.8(5) . . ? C1R C6R C5R 120.4(5) . . ? O1R C7R C1R 111.7(3) . . ? O1R C7R C8R 106.5(4) . . ? C1R C7R C8R 112.1(4) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 30.34 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.764 _refine_diff_density_min -1.264 _refine_diff_density_rms 0.157 # Attachment '1-S-PhEtOH.cif' data_p212121b _database_code_depnum_ccdc_archive 'CCDC 847108' #TrackingRef '1-S-PhEtOH.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 N O8 Zn2 C8 H10 O' _chemical_formula_sum 'C22 H25 N O9 Zn2' _chemical_formula_weight 578.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.337(2) _cell_length_b 11.649(2) _cell_length_c 20.464(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2464.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5155 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 30.36 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.558 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 1.997 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'HKL2000 Scalepack' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.80000 _diffrn_radiation_type 'Synchrotron at Pohang Accelerator Laboratory' _diffrn_radiation_source 'bending mangnet 6B MX beamline' _diffrn_radiation_monochromator 'Si(111) double crystal monochromator' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17272 _diffrn_reflns_av_R_equivalents 0.0620 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 30.36 _reflns_number_total 5155 _reflns_number_gt 5120 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ADSC Quantum-210 ADX Progam' _computing_cell_refinement HKL2000 _computing_data_reduction HKL2000 _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^)+(0.1092P)^2^+1.4886P] 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 0.006(14) _refine_ls_number_reflns 5155 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1316 _refine_ls_wR_factor_gt 0.1311 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.029 _refine_ls_shift/su_mean 0.007 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 0.04354(3) 0.42234(3) -0.00678(2) 0.01423(12) Uani 1 1 d . . . Zn2 Zn 0.35700(3) 0.32479(3) -0.00728(2) 0.01441(13) Uani 1 1 d . . . O1B O 0.3329(2) 0.4141(2) 0.07553(12) 0.0225(5) Uani 1 1 d . . . O2B O 0.1219(3) 0.4579(2) 0.07990(12) 0.0240(5) Uani 1 1 d . . . O3B O 0.3818(2) 0.5353(2) 0.40725(12) 0.0238(5) Uani 1 1 d . . . O4B O 0.1800(2) 0.6088(2) 0.40491(13) 0.0243(6) Uani 1 1 d . . . C1B C 0.2329(3) 0.4467(3) 0.10468(16) 0.0187(7) Uani 1 1 d . . . C2B C 0.2454(3) 0.4778(3) 0.17575(17) 0.0193(6) Uani 1 1 d . . . C3B C 0.1384(3) 0.5187(3) 0.20975(17) 0.0222(7) Uani 1 1 d . . . H3BA H 0.0596 0.5274 0.1884 0.027 Uiso 1 1 calc R . . C4B C 0.3629(4) 0.4654(4) 0.20773(18) 0.0282(8) Uani 1 1 d . . . H4BA H 0.4346 0.4385 0.1850 0.034 Uiso 1 1 calc R . . C5B C 0.1489(3) 0.5467(3) 0.27605(17) 0.0226(7) Uani 1 1 d . . . H5BA H 0.0773 0.5743 0.2986 0.027 Uiso 1 1 calc R . . C6B C 0.3740(3) 0.4929(4) 0.27356(17) 0.0258(8) Uani 1 1 d . . . H6BA H 0.4531 0.4844 0.2947 0.031 Uiso 1 1 calc R . . C7B C 0.2666(3) 0.5332(3) 0.30809(16) 0.0184(6) Uani 1 1 d . . . C8B C 0.2772(3) 0.5620(3) 0.37939(17) 0.0189(7) Uani 1 1 d . . . O1L O 0.1586(2) 0.2708(2) -0.00535(12) 0.0189(5) Uani 1 1 d . . . O2L O 0.0403(2) 0.1156(2) 0.01848(13) 0.0217(5) Uani 1 1 d . . . O3L O 0.3801(2) 0.15880(19) 0.00706(14) 0.0190(5) Uani 1 1 d . . . C1L C 0.1460(3) 0.1670(3) 0.01210(15) 0.0167(6) Uani 1 1 d . . . C2L C 0.2676(3) 0.1004(3) 0.02896(19) 0.0218(7) Uani 1 1 d . . . H2LA H 0.2636 0.0254 0.0073 0.026 Uiso 1 1 calc R . . C3L C 0.2732(3) 0.0813(4) 0.1028(2) 0.0334(9) Uani 1 1 d . . . H3LA H 0.3501 0.0392 0.1136 0.050 Uiso 1 1 calc R . . H3LB H 0.1986 0.0385 0.1165 0.050 Uiso 1 1 calc R . . H3LC H 0.2743 0.1541 0.1247 0.050 Uiso 1 1 calc R . . O1D O -0.0392(2) 0.5892(2) -0.00522(13) 0.0229(5) Uani 1 1 d . . . N1D N -0.0678(3) 0.7663(3) 0.03800(19) 0.0311(7) Uani 1 1 d . . . C1D C -0.0168(4) 0.6628(3) 0.03705(19) 0.0245(7) Uani 1 1 d . . . H1DA H 0.0401 0.6435 0.0705 0.029 Uiso 1 1 calc R . . C2D C -0.1616(5) 0.8018(4) -0.0110(3) 0.0492(13) Uani 1 1 d . . . H2DA H -0.1723 0.7416 -0.0426 0.074 Uiso 1 1 calc R . . H2DB H -0.1313 0.8700 -0.0325 0.074 Uiso 1 1 calc R . . H2DC H -0.2431 0.8172 0.0097 0.074 Uiso 1 1 calc R . . C3D C -0.0372(6) 0.8489(4) 0.0890(3) 0.0497(13) Uani 1 1 d . . . H3DA H 0.0269 0.8171 0.1177 0.075 Uiso 1 1 calc R . . H3DB H -0.1140 0.8663 0.1134 0.075 Uiso 1 1 calc R . . H3DC H -0.0042 0.9179 0.0695 0.075 Uiso 1 1 calc R . . O1S O 0.3979(5) 0.1429(5) -0.2645(3) 0.0820(16) Uani 1 1 d . . . H1SB H 0.4138 0.2063 -0.2799 0.123 Uiso 1 1 calc R . . C1S C 0.1691(6) -0.1768(6) -0.1435(4) 0.0628(16) Uani 1 1 d . . . H1SA H 0.1377 -0.2457 -0.1269 0.075 Uiso 1 1 calc R . . C2S C 0.2417(7) -0.1761(5) -0.2006(3) 0.0574(15) Uani 1 1 d . . . H2SA H 0.2644 -0.2441 -0.2215 0.069 Uiso 1 1 calc R . . C3S C 0.2795(5) -0.0700(5) -0.2253(3) 0.0512(12) Uani 1 1 d . . . H3SA H 0.3270 -0.0684 -0.2639 0.061 Uiso 1 1 calc R . . C4S C 0.2499(5) 0.0338(5) -0.1953(3) 0.0470(12) Uani 1 1 d . . . C5S C 0.1829(6) 0.0301(6) -0.1362(3) 0.0556(14) Uani 1 1 d . . . H5SA H 0.1653 0.0979 -0.1138 0.067 Uiso 1 1 calc R . . C6S C 0.1427(6) -0.0727(6) -0.1109(3) 0.0555(13) Uani 1 1 d . . . H6SA H 0.0975 -0.0740 -0.0716 0.067 Uiso 1 1 calc R . . C7S C 0.2844(6) 0.1497(5) -0.2248(3) 0.0531(13) Uani 1 1 d . . . H7SA H 0.2984 0.2056 -0.1896 0.064 Uiso 1 1 calc R . . C8S C 0.1800(7) 0.1920(6) -0.2690(3) 0.0626(16) Uani 1 1 d . . . H8SA H 0.2043 0.2651 -0.2868 0.094 Uiso 1 1 calc R . . H8SB H 0.1010 0.1999 -0.2448 0.094 Uiso 1 1 calc R . . H8SC H 0.1674 0.1381 -0.3039 0.094 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 0.00633(19) 0.0237(2) 0.01260(19) 0.00041(14) -0.00020(12) -0.00015(12) Zn2 0.00617(19) 0.0239(2) 0.0131(2) -0.00022(14) 0.00018(13) -0.00009(12) O1B 0.0158(11) 0.0359(13) 0.0157(11) -0.0040(10) 0.0027(9) -0.0032(11) O2B 0.0213(12) 0.0339(13) 0.0169(11) -0.0049(10) -0.0051(10) 0.0106(11) O3B 0.0182(12) 0.0358(13) 0.0175(12) -0.0056(10) -0.0074(10) 0.0035(11) O4B 0.0114(10) 0.0466(15) 0.0150(12) -0.0073(11) 0.0019(9) -0.0012(10) C1B 0.0171(16) 0.0262(15) 0.0126(15) -0.0007(12) -0.0031(12) -0.0036(13) C2B 0.0140(15) 0.0277(15) 0.0162(15) -0.0015(13) -0.0011(13) -0.0003(13) C3B 0.0116(15) 0.0389(18) 0.0161(16) -0.0021(14) -0.0021(13) -0.0023(14) C4B 0.0163(16) 0.052(2) 0.0159(16) -0.0069(16) -0.0047(14) 0.0089(17) C5B 0.0095(14) 0.0387(19) 0.0196(17) -0.0033(14) 0.0004(13) -0.0021(14) C6B 0.0119(14) 0.050(2) 0.0152(16) -0.0063(15) -0.0053(13) 0.0061(15) C7B 0.0124(14) 0.0293(15) 0.0137(15) -0.0009(13) -0.0003(12) -0.0003(13) C8B 0.0133(15) 0.0268(15) 0.0167(15) 0.0000(13) -0.0003(12) -0.0043(12) O1L 0.0079(10) 0.0249(10) 0.0239(12) 0.0049(11) -0.0008(10) 0.0026(8) O2L 0.0073(10) 0.0290(11) 0.0287(13) 0.0016(11) -0.0004(10) -0.0024(9) O3L 0.0040(9) 0.0229(9) 0.0301(13) 0.0053(10) 0.0007(10) 0.0005(8) C1L 0.0094(15) 0.0280(15) 0.0128(14) 0.0020(12) 0.0022(11) 0.0001(11) C2L 0.0044(13) 0.0273(14) 0.0337(19) 0.0070(14) 0.0037(13) -0.0035(12) C3L 0.0103(16) 0.055(2) 0.035(2) 0.020(2) -0.0015(14) -0.0006(17) O1D 0.0148(11) 0.0245(11) 0.0293(13) -0.0009(10) -0.0021(10) 0.0028(8) N1D 0.0264(16) 0.0246(14) 0.0423(19) -0.0055(14) -0.0007(15) 0.0054(13) C1D 0.0205(17) 0.0230(15) 0.0300(18) -0.0015(15) 0.0022(14) 0.0040(14) C2D 0.045(3) 0.040(2) 0.063(3) 0.015(2) -0.008(3) 0.021(2) C3D 0.056(3) 0.029(2) 0.064(3) -0.024(2) 0.004(3) 0.001(2) O1S 0.060(3) 0.082(3) 0.104(4) 0.030(3) 0.020(3) -0.003(3) C1S 0.054(3) 0.072(4) 0.063(4) 0.013(3) -0.021(3) -0.015(3) C2S 0.070(4) 0.062(3) 0.040(3) -0.006(3) -0.008(3) -0.015(3) C3S 0.043(3) 0.065(3) 0.045(3) -0.007(3) 0.003(2) -0.002(3) C4S 0.036(2) 0.058(3) 0.047(3) -0.018(2) -0.008(2) 0.003(2) C5S 0.050(3) 0.072(3) 0.045(3) -0.015(3) 0.002(3) -0.001(3) C6S 0.050(3) 0.075(4) 0.041(3) -0.007(3) 0.006(3) -0.009(3) C7S 0.049(3) 0.054(3) 0.056(3) -0.010(3) 0.004(3) -0.012(2) C8S 0.058(3) 0.063(3) 0.067(4) -0.010(3) 0.006(3) -0.005(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 O3L 1.935(2) 4_455 ? Zn1 O3B 1.984(2) 2_564 ? Zn1 O2B 1.993(3) . ? Zn1 O1L 2.129(2) . ? Zn1 O1D 2.124(2) . ? Zn2 O3L 1.970(2) . ? Zn2 O4B 1.993(3) 2_564 ? Zn2 O1B 2.004(3) . ? Zn2 O2L 2.031(2) 4 ? Zn2 O1L 2.145(2) . ? O1B C1B 1.252(4) . ? O2B C1B 1.261(4) . ? O3B C8B 1.261(4) . ? O3B Zn1 1.984(2) 2_565 ? O4B C8B 1.257(4) . ? O4B Zn2 1.993(3) 2_565 ? C1B C2B 1.504(4) . ? C2B C4B 1.387(5) . ? C2B C3B 1.390(5) . ? C3B C5B 1.400(5) . ? C4B C6B 1.389(5) . ? C5B C7B 1.390(5) . ? C6B C7B 1.397(5) . ? C7B C8B 1.501(5) . ? O1L C1L 1.268(4) . ? O2L C1L 1.252(4) . ? O2L Zn2 2.031(2) 4_455 ? O3L C2L 1.420(4) . ? O3L Zn1 1.935(2) 4 ? C1L C2L 1.517(5) . ? C2L C3L 1.528(5) . ? O1D C1D 1.240(5) . ? N1D C1D 1.316(5) . ? N1D C3D 1.454(6) . ? N1D C2D 1.455(6) . ? O1S C7S 1.429(8) . ? C1S C2S 1.388(10) . ? C1S C6S 1.411(10) . ? C2S C3S 1.391(9) . ? C3S C4S 1.390(8) . ? C4S C5S 1.395(8) . ? C4S C7S 1.521(8) . ? C5S C6S 1.370(9) . ? C7S C8S 1.493(10) . ? 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 O3L Zn1 O3B 117.29(12) 4_455 2_564 ? O3L Zn1 O2B 117.31(12) 4_455 . ? O3B Zn1 O2B 125.40(11) 2_564 . ? O3L Zn1 O1L 94.76(9) 4_455 . ? O3B Zn1 O1L 90.06(10) 2_564 . ? O2B Zn1 O1L 86.15(10) . . ? O3L Zn1 O1D 95.49(10) 4_455 . ? O3B Zn1 O1D 86.68(10) 2_564 . ? O2B Zn1 O1D 87.72(10) . . ? O1L Zn1 O1D 169.63(9) . . ? O3L Zn2 O4B 122.57(12) . 2_564 ? O3L Zn2 O1B 113.49(12) . . ? O4B Zn2 O1B 122.48(11) 2_564 . ? O3L Zn2 O2L 103.83(10) . 4 ? O4B Zn2 O2L 86.83(11) 2_564 4 ? O1B Zn2 O2L 91.95(10) . 4 ? O3L Zn2 O1L 79.96(9) . . ? O4B Zn2 O1L 86.96(10) 2_564 . ? O1B Zn2 O1L 91.01(10) . . ? O2L Zn2 O1L 173.77(10) 4 . ? C1B O1B Zn2 131.5(2) . . ? C1B O2B Zn1 134.9(2) . . ? C8B O3B Zn1 132.3(2) . 2_565 ? C8B O4B Zn2 134.1(2) . 2_565 ? O1B C1B O2B 126.2(3) . . ? O1B C1B C2B 117.6(3) . . ? O2B C1B C2B 116.2(3) . . ? C4B C2B C3B 119.7(3) . . ? C4B C2B C1B 120.4(3) . . ? C3B C2B C1B 119.9(3) . . ? C2B C3B C5B 120.2(3) . . ? C2B C4B C6B 120.4(3) . . ? C7B C5B C3B 119.9(3) . . ? C4B C6B C7B 120.1(3) . . ? C5B C7B C6B 119.6(3) . . ? C5B C7B C8B 119.8(3) . . ? C6B C7B C8B 120.6(3) . . ? O4B C8B O3B 127.2(3) . . ? O4B C8B C7B 116.3(3) . . ? O3B C8B C7B 116.5(3) . . ? C1L O1L Zn1 137.5(2) . . ? C1L O1L Zn2 112.55(19) . . ? Zn1 O1L Zn2 106.92(10) . . ? C1L O2L Zn2 129.7(2) . 4_455 ? C2L O3L Zn1 118.8(2) . 4 ? C2L O3L Zn2 114.7(2) . . ? Zn1 O3L Zn2 125.79(11) 4 . ? O2L C1L O1L 125.1(3) . . ? O2L C1L C2L 117.1(3) . . ? O1L C1L C2L 117.8(3) . . ? O3L C2L C1L 111.2(3) . . ? O3L C2L C3L 110.5(3) . . ? C1L C2L C3L 109.3(3) . . ? C1D O1D Zn1 124.6(2) . . ? C1D N1D C3D 122.0(4) . . ? C1D N1D C2D 121.1(4) . . ? C3D N1D C2D 116.8(4) . . ? O1D C1D N1D 124.7(4) . . ? C2S C1S C6S 119.9(6) . . ? C1S C2S C3S 117.6(6) . . ? C2S C3S C4S 123.4(5) . . ? C3S C4S C5S 117.8(6) . . ? C3S C4S C7S 123.0(5) . . ? C5S C4S C7S 119.2(5) . . ? C6S C5S C4S 120.4(6) . . ? C5S C6S C1S 120.9(5) . . ? O1S C7S C8S 105.5(6) . . ? O1S C7S C4S 111.6(5) . . ? C8S C7S C4S 111.3(5) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.36 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.691 _refine_diff_density_min -2.210 _refine_diff_density_rms 0.152