# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_name 'Chih-Chieh Wang' _publ_contact_author_name 'Chih-Chieh Wang' _publ_contact_author_email ccwang@scu.edu.tw data_ic10009 _database_code_depnum_ccdc_archive 'CCDC 757053' #TrackingRef '- compound1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 N2 O6 Zn' _chemical_formula_weight 397.68 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.1516(5) _cell_length_b 8.0418(3) _cell_length_c 18.4027(8) _cell_angle_alpha 90.00 _cell_angle_beta 98.5030(10) _cell_angle_gamma 90.00 _cell_volume 1778.56(13) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4778 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.46 _exptl_crystal_description plate _exptl_crystal_colour light-brown _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 1.414 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7188 _exptl_absorpt_correction_T_max 0.8833 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 ApexCCD area detector' _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 17101 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4077 _reflns_number_gt 3550 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAIM\NT' _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^)+(0.0258P)^2^+1.5427P] 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 4077 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0578 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.0962 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 1.213 _refine_ls_restrained_S_all 1.213 _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 1.0000 0.0000 0.0000 0.02877(12) Uani 1 2 d S . . Zn2 Zn 0.5000 -0.5000 0.0000 0.03059(12) Uani 1 2 d S . . O1 O 1.07003(14) 0.2370(2) 0.01319(12) 0.0364(5) Uani 1 1 d . . . O2 O 1.17658(14) 0.6034(2) 0.01995(12) 0.0372(5) Uani 1 1 d . . . O3 O 0.57681(14) -0.7401(2) 0.01053(12) 0.0377(5) Uani 1 1 d . . . O4 O 0.33562(15) -0.8994(2) 0.02723(14) 0.0505(6) Uani 1 1 d . . . O5 O 1.15584(15) -0.0778(3) 0.05316(12) 0.0316(4) Uani 1 1 d . . . H5A H 1.174(3) -0.180(5) 0.0477(19) 0.059(11) Uiso 1 1 d . . . H5B H 1.206(3) -0.018(4) 0.045(2) 0.055(11) Uiso 1 1 d . . . O6 O 0.36453(16) -0.5755(3) 0.04889(12) 0.0352(5) Uani 1 1 d . . . H6A H 0.346(3) -0.680(4) 0.0426(17) 0.043(9) Uiso 1 1 d . . . H6B H 0.309(3) -0.527(4) 0.0391(17) 0.038(9) Uiso 1 1 d . . . N1 N 0.9401(2) 0.0060(3) 0.10827(14) 0.0389(6) Uani 1 1 d . . . N2 N 0.58283(19) -0.4335(3) 0.10742(14) 0.0394(6) Uani 1 1 d . . . C1 C 1.03111(19) 0.3802(3) 0.00570(14) 0.0246(5) Uani 1 1 d . . . C2 C 1.07977(19) 0.5465(3) 0.00903(14) 0.0241(5) Uani 1 1 d . . . C3 C 0.5339(2) -0.8815(3) 0.00479(15) 0.0292(6) Uani 1 1 d . . . C4 C 0.4258(2) -0.9551(3) 0.01233(16) 0.0297(6) Uani 1 1 d . . . C5 C 0.9891(3) -0.0887(4) 0.16351(19) 0.0489(8) Uani 1 1 d . . . H5C H 1.0558 -0.1405 0.1582 0.059 Uiso 1 1 calc R . . C6 C 0.9464(3) -0.1137(5) 0.22762(19) 0.0542(9) Uani 1 1 d . . . H6C H 0.9845 -0.1801 0.2644 0.065 Uiso 1 1 calc R . . C7 C 0.8469(3) -0.0406(4) 0.23769(17) 0.0444(7) Uani 1 1 d . . . C8 C 0.7979(3) 0.0598(4) 0.18190(19) 0.0508(8) Uani 1 1 d . . . H8A H 0.7318 0.1146 0.1864 0.061 Uiso 1 1 calc R . . C9 C 0.8461(3) 0.0800(4) 0.11906(18) 0.0463(8) Uani 1 1 d . . . H9A H 0.8109 0.1492 0.0823 0.056 Uiso 1 1 calc R . . C10 C 0.7924(3) -0.0765(5) 0.30457(18) 0.0571(9) Uani 1 1 d . . . H10A H 0.7243 -0.0123 0.3016 0.069 Uiso 1 1 calc R . . H10B H 0.8416 -0.0411 0.3482 0.069 Uiso 1 1 calc R . . C11 C 0.7650(3) -0.2612(5) 0.31203(17) 0.0543(9) Uani 1 1 d . . . H11A H 0.8336 -0.3237 0.3236 0.065 Uiso 1 1 calc R . . H11B H 0.7225 -0.2756 0.3523 0.065 Uiso 1 1 calc R . . C12 C 0.5341(3) -0.3409(4) 0.1541(2) 0.0511(8) Uani 1 1 d . . . H12A H 0.4599 -0.3110 0.1408 0.061 Uiso 1 1 calc R . . C13 C 0.5887(3) -0.2880(5) 0.2209(2) 0.0563(9) Uani 1 1 d . . . H13A H 0.5511 -0.2246 0.2516 0.068 Uiso 1 1 calc R . . C14 C 0.6993(3) -0.3285(4) 0.24258(17) 0.0443(7) Uani 1 1 d . . . C15 C 0.7475(3) -0.4277(5) 0.19492(19) 0.0508(8) Uani 1 1 d . . . H15A H 0.8209 -0.4621 0.2075 0.061 Uiso 1 1 calc R . . C16 C 0.6882(3) -0.4762(4) 0.12907(19) 0.0468(8) Uani 1 1 d . . . H16A H 0.7236 -0.5422 0.0980 0.056 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 0.0260(2) 0.0158(2) 0.0452(3) 0.00043(18) 0.00732(18) -0.00054(16) Zn2 0.0248(2) 0.0183(2) 0.0501(3) -0.00304(18) 0.01042(18) -0.00155(16) O1 0.0260(9) 0.0146(9) 0.0671(14) 0.0007(9) 0.0018(9) 0.0009(7) O2 0.0201(8) 0.0179(9) 0.0732(15) 0.0003(9) 0.0053(8) -0.0016(7) O3 0.0269(9) 0.0160(9) 0.0721(15) -0.0026(9) 0.0135(9) -0.0020(7) O4 0.0287(10) 0.0208(10) 0.109(2) -0.0098(11) 0.0323(11) -0.0008(8) O5 0.0244(9) 0.0177(9) 0.0535(13) -0.0013(9) 0.0084(8) -0.0018(8) O6 0.0224(9) 0.0195(10) 0.0658(15) 0.0029(9) 0.0135(9) 0.0018(8) N1 0.0378(13) 0.0327(13) 0.0479(15) 0.0004(11) 0.0122(11) -0.0029(10) N2 0.0336(12) 0.0336(13) 0.0521(16) -0.0079(11) 0.0095(11) -0.0028(10) C1 0.0234(11) 0.0163(12) 0.0335(14) 0.0017(10) 0.0029(10) -0.0001(9) C2 0.0230(11) 0.0173(11) 0.0322(13) 0.0004(10) 0.0041(10) 0.0006(9) C3 0.0238(12) 0.0203(13) 0.0451(16) -0.0001(11) 0.0104(11) 0.0001(10) C4 0.0253(12) 0.0184(12) 0.0472(17) -0.0019(11) 0.0110(11) -0.0005(9) C5 0.0362(15) 0.055(2) 0.056(2) 0.0090(17) 0.0079(14) 0.0034(15) C6 0.0463(18) 0.072(3) 0.0429(19) 0.0116(17) 0.0030(14) -0.0001(17) C7 0.0503(18) 0.0442(18) 0.0388(17) -0.0081(14) 0.0068(14) -0.0105(14) C8 0.0549(19) 0.050(2) 0.051(2) -0.0053(16) 0.0204(16) 0.0092(16) C9 0.0514(18) 0.0396(18) 0.0500(19) 0.0036(15) 0.0148(15) 0.0105(15) C10 0.072(2) 0.071(2) 0.0312(17) -0.0127(17) 0.0142(16) -0.010(2) C11 0.066(2) 0.068(2) 0.0304(17) 0.0016(16) 0.0102(15) -0.0053(19) C12 0.0359(16) 0.057(2) 0.062(2) -0.0144(17) 0.0135(15) 0.0017(15) C13 0.054(2) 0.065(2) 0.055(2) -0.0181(18) 0.0241(17) -0.0019(17) C14 0.0506(18) 0.0457(18) 0.0387(17) 0.0024(14) 0.0136(14) -0.0071(15) C15 0.0443(17) 0.056(2) 0.051(2) -0.0026(16) 0.0015(14) 0.0103(16) C16 0.0422(16) 0.0422(18) 0.055(2) -0.0100(15) 0.0049(14) 0.0131(14) _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 2.0869(17) . ? Zn1 O1 2.0869(17) 3_755 ? Zn1 O5 2.0943(19) . ? Zn1 O5 2.0943(19) 3_755 ? Zn1 N1 2.220(2) 3_755 ? Zn1 N1 2.221(2) . ? Zn2 O6 2.0799(19) . ? Zn2 O6 2.0799(19) 3_645 ? Zn2 O3 2.1411(18) 3_645 ? Zn2 O3 2.1412(18) . ? Zn2 N2 2.149(3) . ? Zn2 N2 2.149(3) 3_645 ? O1 C1 1.245(3) . ? O2 C2 1.251(3) . ? O3 C3 1.249(3) . ? O4 C4 1.251(3) . ? N1 C9 1.329(4) . ? N1 C5 1.337(4) . ? N2 C16 1.329(4) . ? N2 C12 1.340(4) . ? C1 C2 1.459(3) 3_765 ? C1 C2 1.460(3) . ? C2 C1 1.459(3) 3_765 ? C3 C4 1.453(3) 3_635 ? C3 C4 1.465(3) . ? C4 C3 1.453(3) 3_635 ? C5 C6 1.372(4) . ? C6 C7 1.381(5) . ? C7 C8 1.371(5) . ? C7 C10 1.509(4) . ? C8 C9 1.381(4) . ? C10 C11 1.533(5) . ? C11 C14 1.504(4) . ? C12 C13 1.375(5) . ? C13 C14 1.383(5) . ? C14 C15 1.378(4) . ? C15 C16 1.371(4) . ? 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 180.0 . 3_755 ? O1 Zn1 O5 83.88(7) . . ? O1 Zn1 O5 96.12(7) 3_755 . ? O1 Zn1 O5 96.12(7) . 3_755 ? O1 Zn1 O5 83.88(7) 3_755 3_755 ? O5 Zn1 O5 180.0 . 3_755 ? O1 Zn1 N1 86.68(8) . 3_755 ? O1 Zn1 N1 93.33(8) 3_755 3_755 ? O5 Zn1 N1 91.09(9) . 3_755 ? O5 Zn1 N1 88.91(9) 3_755 3_755 ? O1 Zn1 N1 93.32(8) . . ? O1 Zn1 N1 86.67(8) 3_755 . ? O5 Zn1 N1 88.91(9) . . ? O5 Zn1 N1 91.09(9) 3_755 . ? N1 Zn1 N1 179.999(1) 3_755 . ? O6 Zn2 O6 180.0 . 3_645 ? O6 Zn2 O3 86.57(8) . 3_645 ? O6 Zn2 O3 93.43(8) 3_645 3_645 ? O6 Zn2 O3 93.43(8) . . ? O6 Zn2 O3 86.57(8) 3_645 . ? O3 Zn2 O3 180.0 3_645 . ? O6 Zn2 N2 88.16(9) . . ? O6 Zn2 N2 91.85(9) 3_645 . ? O3 Zn2 N2 89.84(9) 3_645 . ? O3 Zn2 N2 90.16(9) . . ? O6 Zn2 N2 91.84(9) . 3_645 ? O6 Zn2 N2 88.15(9) 3_645 3_645 ? O3 Zn2 N2 90.16(9) 3_645 3_645 ? O3 Zn2 N2 89.84(9) . 3_645 ? N2 Zn2 N2 180.00(7) . 3_645 ? C1 O1 Zn1 133.66(16) . . ? C3 O3 Zn2 129.98(16) . . ? C9 N1 C5 115.9(3) . . ? C9 N1 Zn1 123.1(2) . . ? C5 N1 Zn1 120.1(2) . . ? C16 N2 C12 116.7(3) . . ? C16 N2 Zn2 120.7(2) . . ? C12 N2 Zn2 122.5(2) . . ? O1 C1 C2 136.0(2) . 3_765 ? O1 C1 C2 134.3(2) . . ? C2 C1 C2 89.72(19) 3_765 . ? O2 C2 C1 134.7(2) . 3_765 ? O2 C2 C1 135.0(2) . . ? C1 C2 C1 90.28(19) 3_765 . ? O3 C3 C4 133.8(2) . 3_635 ? O3 C3 C4 136.7(2) . . ? C4 C3 C4 89.5(2) 3_635 . ? O4 C4 C3 134.9(2) . 3_635 ? O4 C4 C3 134.6(2) . . ? C3 C4 C3 90.5(2) 3_635 . ? N1 C5 C6 123.7(3) . . ? C5 C6 C7 120.2(3) . . ? C8 C7 C6 116.2(3) . . ? C8 C7 C10 121.9(3) . . ? C6 C7 C10 121.8(3) . . ? C7 C8 C9 120.3(3) . . ? N1 C9 C8 123.6(3) . . ? C7 C10 C11 112.7(3) . . ? C14 C11 C10 111.6(3) . . ? N2 C12 C13 123.0(3) . . ? C12 C13 C14 120.4(3) . . ? C15 C14 C13 116.0(3) . . ? C15 C14 C11 121.8(3) . . ? C13 C14 C11 122.1(3) . . ? C16 C15 C14 120.7(3) . . ? N2 C16 C15 123.2(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.346 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.054 # Attachment 'compound2.cif' data_ic8907 _database_code_depnum_ccdc_archive 'CCDC 757054' #TrackingRef 'compound2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H23 N2 O15 Zn2' _chemical_formula_weight 686.16 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 8.0228(3) _cell_length_b 8.1119(3) _cell_length_c 19.1586(8) _cell_angle_alpha 78.6019(14) _cell_angle_beta 87.3341(13) _cell_angle_gamma 88.6256(14) _cell_volume 1220.79(8) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4258 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 26.88 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.867 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 698 _exptl_absorpt_coefficient_mu 2.050 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6846 _exptl_absorpt_correction_T_max 0.9225 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 ApexCCD area detector' _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 16310 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.09 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5607 _reflns_number_gt 4961 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0518P)^2^+0.7001P] 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 SHELXL _refine_ls_extinction_coef 0.0018(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5607 _refine_ls_number_parameters 374 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 1.196 _refine_ls_restrained_S_all 1.196 _refine_ls_shift/su_max 0.002 _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 0.5000 0.5000 0.01828(14) Uani 1 2 d S . . Zn2 Zn -0.5000 1.0000 0.5000 0.01986(15) Uani 1 2 d S . . Zn3 Zn -0.29215(5) -0.36121(5) 0.78176(2) 0.01810(12) Uani 1 1 d . . . O1 O -0.1074(3) 0.7375(3) 0.50922(14) 0.0232(5) Uani 1 1 d . . . O2 O -0.2644(3) 1.1076(3) 0.51170(12) 0.0184(5) Uani 1 1 d . . . O3 O -0.1098(4) 0.3990(3) 0.59943(14) 0.0383(7) Uani 1 1 d . . . H3 H -0.1184 0.2980 0.6054 0.057 Uiso 1 1 d . . . H3' H -0.1088 0.4642 0.6261 0.057 Uiso 1 1 d . . . O4 O -0.4351(3) 0.7534(3) 0.56207(14) 0.0296(6) Uani 1 1 d . . . H4 H -0.3448 0.7334 0.5473 0.044 Uiso 1 1 d . . . H4' H -0.4289 0.7387 0.6011 0.044 Uiso 1 1 d . . . O5 O -0.2153(3) 0.4478(3) 0.45407(14) 0.0269(5) Uani 1 1 d . . . H5 H -0.1980 0.4388 0.4068 0.040 Uiso 1 1 d . . . H5' H -0.2540 0.3582 0.4709 0.040 Uiso 1 1 d . . . O6 O -0.3598(3) -0.1349(3) 0.81482(13) 0.0260(5) Uani 1 1 d . . . O7 O -0.1711(4) 0.0879(3) 0.67514(14) 0.0315(6) Uani 1 1 d . . . O8 O -0.2113(3) 0.4166(3) 0.74618(13) 0.0257(5) Uani 1 1 d . . . O9 O -0.3903(4) 0.1904(3) 0.88673(14) 0.0348(7) Uani 1 1 d . . . O10 O -0.0570(3) -0.3496(4) 0.83122(13) 0.0278(6) Uani 1 1 d . . . O11 O 0.3036(3) -0.3728(4) 0.89649(14) 0.0351(7) Uani 1 1 d . . . O12 O 0.4758(3) -0.3722(3) 0.73663(13) 0.0262(5) Uani 1 1 d . . . O13 O 0.1118(3) -0.3696(3) 0.67528(13) 0.0267(6) Uani 1 1 d . . . O14 O -0.2012(3) -0.2422(3) 0.68232(13) 0.0241(5) Uani 1 1 d . . . H14 H -0.1952 -0.1405 0.6774 0.036 Uiso 1 1 d . . . H14' H -0.1203 -0.2718 0.6752 0.036 Uiso 1 1 d . . . O15 O -0.3759(3) -0.4780(3) 0.88298(13) 0.0255(5) Uani 1 1 d . . . H15 H -0.4608 -0.4531 0.8903 0.038 Uiso 1 1 d . . . H15' H -0.3781 -0.5875 0.8860 0.038 Uiso 1 1 d . . . N1 N -0.5905(4) 1.0832(4) 0.59157(15) 0.0216(6) Uani 1 1 d . . . N2 N -0.8974(5) 1.2627(5) 1.03905(18) 0.0380(8) Uani 1 1 d . . . H2A H -0.9140 1.3006 1.0777 0.046 Uiso 1 1 calc R . . C1 C -0.0472(4) 0.8807(4) 0.50388(17) 0.0171(6) Uani 1 1 d . . . C2 C -0.1193(4) 1.0474(4) 0.50559(17) 0.0165(6) Uani 1 1 d . . . C3 C -0.5411(5) 1.2251(5) 0.6098(2) 0.0276(8) Uani 1 1 d . . . H3A H -0.4656 1.2932 0.5795 0.033 Uiso 1 1 calc R . . C4 C -0.5983(4) 1.2743(5) 0.67224(19) 0.0251(7) Uani 1 1 d . . . H4A H -0.5612 1.3737 0.6831 0.030 Uiso 1 1 calc R . . C5 C -0.7102(4) 1.1759(4) 0.71812(18) 0.0230(7) Uani 1 1 d . . . C6 C -0.7665(5) 1.0334(5) 0.69707(19) 0.0287(8) Uani 1 1 d . . . H6A H -0.8480 0.9674 0.7246 0.034 Uiso 1 1 calc R . . C7 C -0.7012(5) 0.9904(5) 0.6353(2) 0.0271(8) Uani 1 1 d . . . H7A H -0.7362 0.8913 0.6236 0.032 Uiso 1 1 calc R . . C8 C -0.7725(5) 1.2229(4) 0.78684(19) 0.0270(8) Uani 1 1 d . . . H8A H -0.8722 1.2925 0.7776 0.032 Uiso 1 1 calc R . . H8B H -0.6888 1.2912 0.8019 0.032 Uiso 1 1 calc R . . C9 C -0.8134(6) 1.0780(5) 0.8483(2) 0.0337(9) Uani 1 1 d . . . H9A H -0.9115 1.0209 0.8379 0.040 Uiso 1 1 calc R . . H9B H -0.7211 0.9977 0.8537 0.040 Uiso 1 1 calc R . . C10 C -1.0167(6) 1.2795(6) 0.9932(2) 0.0447(11) Uani 1 1 d . . . H10A H -1.1178 1.3303 1.0032 0.054 Uiso 1 1 calc R . . C11 C -0.9927(5) 1.2224(6) 0.9307(2) 0.0424(11) Uani 1 1 d . . . H11A H -1.0757 1.2385 0.8976 0.051 Uiso 1 1 calc R . . C12 C -0.8455(5) 1.1411(5) 0.91689(19) 0.0271(8) Uani 1 1 d . . . C13 C -0.7243(5) 1.1262(6) 0.9665(2) 0.0380(10) Uani 1 1 d . . . H13A H -0.6231 1.0733 0.9585 0.046 Uiso 1 1 calc R . . C14 C -0.7521(6) 1.1889(6) 1.0273(2) 0.0400(10) Uani 1 1 d . . . H14A H -0.6694 1.1797 1.0604 0.048 Uiso 1 1 calc R . . C15 C -0.3161(4) 0.0145(4) 0.79580(18) 0.0209(7) Uani 1 1 d . . . C16 C -0.2311(4) 0.1166(4) 0.73316(19) 0.0232(7) Uani 1 1 d . . . C17 C -0.2501(4) 0.2640(4) 0.76561(18) 0.0205(7) Uani 1 1 d . . . C18 C -0.3331(4) 0.1625(4) 0.82881(19) 0.0217(7) Uani 1 1 d . . . C19 C 0.0900(4) -0.3599(4) 0.80519(18) 0.0205(7) Uani 1 1 d . . . C20 C 0.2545(4) -0.3682(4) 0.83560(18) 0.0221(7) Uani 1 1 d . . . C21 C 0.3323(4) -0.3696(4) 0.76426(18) 0.0207(7) Uani 1 1 d . . . C22 C 0.1659(4) -0.3674(4) 0.73526(19) 0.0209(7) 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 0.0213(3) 0.0139(3) 0.0199(3) -0.0043(2) 0.0020(2) -0.0019(2) Zn2 0.0192(3) 0.0214(3) 0.0202(3) -0.0078(2) 0.0025(2) -0.0017(2) Zn3 0.0197(2) 0.0167(2) 0.0185(2) -0.00514(15) 0.00079(15) -0.00164(14) O1 0.0191(12) 0.0160(11) 0.0360(14) -0.0095(10) 0.0020(10) -0.0023(9) O2 0.0151(11) 0.0175(11) 0.0238(12) -0.0075(9) 0.0003(9) 0.0010(9) O3 0.071(2) 0.0203(13) 0.0234(14) -0.0069(11) 0.0154(14) -0.0136(13) O4 0.0259(13) 0.0332(14) 0.0296(14) -0.0063(11) -0.0015(11) 0.0049(11) O5 0.0294(13) 0.0220(13) 0.0301(14) -0.0065(11) -0.0023(11) -0.0028(10) O6 0.0378(14) 0.0161(12) 0.0241(13) -0.0054(10) 0.0074(11) -0.0046(10) O7 0.0499(17) 0.0210(13) 0.0229(13) -0.0056(10) 0.0125(12) -0.0039(12) O8 0.0323(14) 0.0151(11) 0.0291(13) -0.0052(10) 0.0094(11) -0.0028(10) O9 0.0523(18) 0.0240(14) 0.0282(14) -0.0082(11) 0.0139(13) -0.0067(12) O10 0.0191(12) 0.0460(16) 0.0211(13) -0.0146(11) 0.0040(10) -0.0014(11) O11 0.0265(14) 0.0569(19) 0.0245(14) -0.0150(13) -0.0029(11) 0.0062(13) O12 0.0178(12) 0.0370(14) 0.0272(13) -0.0156(11) 0.0026(10) -0.0019(10) O13 0.0230(12) 0.0399(15) 0.0190(12) -0.0101(11) 0.0013(10) -0.0020(11) O14 0.0290(13) 0.0192(12) 0.0234(13) -0.0038(10) 0.0045(10) -0.0021(10) O15 0.0243(13) 0.0238(13) 0.0278(13) -0.0051(10) 0.0043(10) -0.0004(10) N1 0.0211(14) 0.0251(15) 0.0208(14) -0.0105(12) 0.0011(11) -0.0001(11) N2 0.053(2) 0.044(2) 0.0207(16) -0.0169(15) 0.0092(15) -0.0084(17) C1 0.0175(15) 0.0176(15) 0.0170(15) -0.0058(12) 0.0012(12) 0.0014(12) C2 0.0199(15) 0.0130(14) 0.0164(15) -0.0029(12) -0.0007(12) -0.0010(12) C3 0.0282(19) 0.0276(19) 0.0276(19) -0.0078(15) 0.0054(15) -0.0063(15) C4 0.0265(18) 0.0255(18) 0.0253(18) -0.0104(15) 0.0008(14) -0.0031(14) C5 0.0277(18) 0.0251(18) 0.0170(16) -0.0066(14) 0.0004(14) 0.0043(14) C6 0.040(2) 0.0254(18) 0.0208(18) -0.0052(15) 0.0069(15) -0.0081(16) C7 0.035(2) 0.0218(17) 0.0267(19) -0.0105(15) 0.0028(15) -0.0060(15) C8 0.040(2) 0.0211(17) 0.0218(18) -0.0103(14) 0.0040(15) 0.0006(15) C9 0.052(3) 0.029(2) 0.0211(19) -0.0106(16) 0.0040(17) -0.0006(18) C10 0.037(2) 0.060(3) 0.042(3) -0.024(2) 0.008(2) 0.003(2) C11 0.035(2) 0.066(3) 0.033(2) -0.023(2) -0.0032(18) -0.001(2) C12 0.036(2) 0.0259(18) 0.0190(17) -0.0057(14) 0.0077(15) -0.0071(15) C13 0.038(2) 0.050(3) 0.026(2) -0.0073(18) 0.0026(17) 0.0042(19) C14 0.045(3) 0.053(3) 0.023(2) -0.0092(19) -0.0053(18) -0.005(2) C15 0.0235(17) 0.0183(16) 0.0212(17) -0.0043(13) -0.0023(13) -0.0005(13) C16 0.0273(18) 0.0178(16) 0.0238(18) -0.0023(14) 0.0002(14) -0.0002(13) C17 0.0210(16) 0.0191(16) 0.0215(17) -0.0047(13) -0.0001(13) -0.0003(13) C18 0.0261(18) 0.0141(15) 0.0249(18) -0.0042(13) 0.0022(14) -0.0023(13) C19 0.0222(17) 0.0203(16) 0.0202(16) -0.0074(13) 0.0011(13) -0.0012(13) C20 0.0196(16) 0.0263(18) 0.0223(17) -0.0103(14) 0.0014(13) 0.0008(13) C21 0.0229(17) 0.0197(16) 0.0211(17) -0.0080(13) 0.0007(13) -0.0019(13) C22 0.0222(17) 0.0177(16) 0.0240(17) -0.0080(13) 0.0028(13) -0.0006(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O5 2.064(3) 2_566 ? Zn1 O5 2.064(3) . ? Zn1 O3 2.083(3) . ? Zn1 O3 2.083(3) 2_566 ? Zn1 O1 2.127(2) . ? Zn1 O1 2.127(2) 2_566 ? Zn2 N1 2.094(3) . ? Zn2 N1 2.094(3) 2_476 ? Zn2 O2 2.140(2) . ? Zn2 O2 2.140(2) 2_476 ? Zn2 O4 2.181(3) . ? Zn2 O4 2.181(3) 2_476 ? Zn3 O14 2.067(2) . ? Zn3 O15 2.072(2) . ? Zn3 O12 2.100(2) 1_455 ? Zn3 O6 2.109(2) . ? Zn3 O8 2.126(2) 1_545 ? Zn3 O10 2.162(2) . ? O1 C1 1.253(4) . ? O2 C2 1.261(4) . ? O6 C15 1.248(4) . ? O7 C16 1.252(4) . ? O8 C17 1.263(4) . ? O8 Zn3 2.126(2) 1_565 ? O9 C18 1.241(4) . ? O10 C19 1.266(4) . ? O11 C20 1.242(4) . ? O12 C21 1.246(4) . ? O12 Zn3 2.100(2) 1_655 ? O13 C22 1.251(4) . ? N1 C7 1.331(5) . ? N1 C3 1.341(5) . ? N2 C10 1.316(6) . ? N2 C14 1.328(6) . ? C1 C2 1.460(4) 2_576 ? C1 C2 1.464(4) . ? C2 C1 1.460(4) 2_576 ? C3 C4 1.389(5) . ? C4 C5 1.378(5) . ? C5 C6 1.389(5) . ? C5 C8 1.502(5) . ? C6 C7 1.375(5) . ? C8 C9 1.520(5) . ? C9 C12 1.512(5) . ? C10 C11 1.370(6) . ? C11 C12 1.380(6) . ? C12 C13 1.377(6) . ? C13 C14 1.368(6) . ? C15 C18 1.464(5) . ? C15 C16 1.466(5) . ? C16 C17 1.455(5) . ? C17 C18 1.465(5) . ? C19 C22 1.458(5) . ? C19 C20 1.462(5) . ? C20 C21 1.478(5) . ? C21 C22 1.467(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 O5 Zn1 O5 180.000(1) 2_566 . ? O5 Zn1 O3 91.35(11) 2_566 . ? O5 Zn1 O3 88.65(12) . . ? O5 Zn1 O3 88.65(12) 2_566 2_566 ? O5 Zn1 O3 91.35(11) . 2_566 ? O3 Zn1 O3 180.000(1) . 2_566 ? O5 Zn1 O1 91.52(9) 2_566 . ? O5 Zn1 O1 88.48(9) . . ? O3 Zn1 O1 88.64(10) . . ? O3 Zn1 O1 91.36(10) 2_566 . ? O5 Zn1 O1 88.48(9) 2_566 2_566 ? O5 Zn1 O1 91.52(9) . 2_566 ? O3 Zn1 O1 91.36(10) . 2_566 ? O3 Zn1 O1 88.64(10) 2_566 2_566 ? O1 Zn1 O1 180.00(14) . 2_566 ? N1 Zn2 N1 180.000(1) . 2_476 ? N1 Zn2 O2 88.65(10) . . ? N1 Zn2 O2 91.35(10) 2_476 . ? N1 Zn2 O2 91.35(10) . 2_476 ? N1 Zn2 O2 88.65(10) 2_476 2_476 ? O2 Zn2 O2 180.000(1) . 2_476 ? N1 Zn2 O4 91.65(11) . . ? N1 Zn2 O4 88.35(11) 2_476 . ? O2 Zn2 O4 94.29(9) . . ? O2 Zn2 O4 85.71(9) 2_476 . ? N1 Zn2 O4 88.35(11) . 2_476 ? N1 Zn2 O4 91.65(11) 2_476 2_476 ? O2 Zn2 O4 85.71(9) . 2_476 ? O2 Zn2 O4 94.29(9) 2_476 2_476 ? O4 Zn2 O4 180.00(13) . 2_476 ? O14 Zn3 O15 178.00(10) . . ? O14 Zn3 O12 87.85(10) . 1_455 ? O15 Zn3 O12 94.09(10) . 1_455 ? O14 Zn3 O6 94.09(9) . . ? O15 Zn3 O6 85.37(10) . . ? O12 Zn3 O6 91.82(10) 1_455 . ? O14 Zn3 O8 83.69(9) . 1_545 ? O15 Zn3 O8 96.78(10) . 1_545 ? O12 Zn3 O8 90.32(10) 1_455 1_545 ? O6 Zn3 O8 176.86(9) . 1_545 ? O14 Zn3 O10 93.63(10) . . ? O15 Zn3 O10 84.42(10) . . ? O12 Zn3 O10 178.30(9) 1_455 . ? O6 Zn3 O10 87.26(10) . . ? O8 Zn3 O10 90.66(10) 1_545 . ? C1 O1 Zn1 132.9(2) . . ? C2 O2 Zn2 129.3(2) . . ? C15 O6 Zn3 134.4(2) . . ? C17 O8 Zn3 132.8(2) . 1_565 ? C19 O10 Zn3 129.1(2) . . ? C21 O12 Zn3 129.7(2) . 1_655 ? C7 N1 C3 117.2(3) . . ? C7 N1 Zn2 119.1(2) . . ? C3 N1 Zn2 123.6(2) . . ? C10 N2 C14 121.9(4) . . ? O1 C1 C2 136.3(3) . 2_576 ? O1 C1 C2 133.9(3) . . ? C2 C1 C2 89.8(3) 2_576 . ? O2 C2 C1 134.0(3) . 2_576 ? O2 C2 C1 135.8(3) . . ? C1 C2 C1 90.2(3) 2_576 . ? N1 C3 C4 122.5(3) . . ? C5 C4 C3 120.0(3) . . ? C4 C5 C6 117.0(3) . . ? C4 C5 C8 121.7(3) . . ? C6 C5 C8 121.3(3) . . ? C7 C6 C5 119.7(3) . . ? N1 C7 C6 123.5(3) . . ? C5 C8 C9 116.3(3) . . ? C12 C9 C8 110.7(3) . . ? N2 C10 C11 120.3(4) . . ? C10 C11 C12 120.0(4) . . ? C13 C12 C11 117.6(4) . . ? C13 C12 C9 120.7(4) . . ? C11 C12 C9 121.6(4) . . ? C14 C13 C12 120.4(4) . . ? N2 C14 C13 119.8(4) . . ? O6 C15 C18 133.6(3) . . ? O6 C15 C16 136.6(3) . . ? C18 C15 C16 89.9(3) . . ? O7 C16 C17 135.4(3) . . ? O7 C16 C15 134.5(3) . . ? C17 C16 C15 90.1(3) . . ? O8 C17 C16 134.3(3) . . ? O8 C17 C18 135.5(3) . . ? C16 C17 C18 90.3(3) . . ? O9 C18 C15 135.4(3) . . ? O9 C18 C17 134.8(3) . . ? C15 C18 C17 89.8(3) . . ? O10 C19 C22 136.1(3) . . ? O10 C19 C20 133.1(3) . . ? C22 C19 C20 90.8(3) . . ? O11 C20 C19 134.0(3) . . ? O11 C20 C21 136.6(3) . . ? C19 C20 C21 89.4(3) . . ? O12 C21 C22 132.6(3) . . ? O12 C21 C20 137.6(3) . . ? C22 C21 C20 89.8(3) . . ? O13 C22 C19 135.0(3) . . ? O13 C22 C21 135.0(3) . . ? C19 C22 C21 90.0(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.648 _refine_diff_density_min -0.834 _refine_diff_density_rms 0.118