# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 _publ_contact_author_name 'Prof Hong-Chang Liang' _publ_contact_author_address ; Chemistry and Biochemistry San Diego State University 5500 Campanile Drive San Diego CA 92182-1030 UNITED STATES OF AMERICA ; _publ_contact_author_email HCLIANG@SCIENCES.SDSU.EDU _publ_section_title ; Syntheses of Water-Soluble N-donor Ligands for Aqueous Catalysis Using Green, Michael-Type Addition Reactions ; loop_ _publ_author_name 'Hong-Chang Liang' 'Sanjib K. Das' 'Juan R. Galvan' 'Arnold Rheingold' 'Suzanne M. Sato' ; L.N.Zakharov ; 'Yonglian Zhang' data_liang01a _database_code_depnum_ccdc_archive 'CCDC 268563' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H19 Cl2 N2 Na O6 S Zn' _chemical_formula_weight 442.58 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' Na Na 0.0362 0.0249 '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 18.3353(10) _cell_length_b 7.6965(4) _cell_length_c 12.7734(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.1480(10) _cell_angle_gamma 90.00 _cell_volume 1747.88(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7174 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.27 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 1.880 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5353 _exptl_absorpt_correction_T_max 0.8956 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 10766 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4038 _reflns_number_gt 3601 _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^)+(0.0400P)^2^+0.7000P] 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 4038 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0745 _refine_ls_wR_factor_gt 0.0723 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.004 _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 0.314803(13) 0.39276(3) 0.273949(17) 0.02052(8) Uani 1 1 d . . . Cl1 Cl 0.40075(3) 0.22551(9) 0.22835(5) 0.03715(15) Uani 1 1 d . . . Cl2 Cl 0.22983(3) 0.53068(7) 0.14588(4) 0.02552(12) Uani 1 1 d . . . Na1 Na 0.07301(5) 0.38425(10) 0.08284(6) 0.02439(18) Uani 1 1 d . . . S1 S 0.13779(3) -0.01719(6) 0.20932(4) 0.02052(11) Uani 1 1 d . . . O1 O 0.10988(8) 0.15937(19) 0.21387(12) 0.0265(3) Uani 1 1 d . . . O2 O 0.10931(10) -0.1348(2) 0.27976(13) 0.0329(4) Uani 1 1 d . . . O3 O 0.12574(9) -0.08191(19) 0.09930(12) 0.0263(3) Uani 1 1 d . . . O4 O 0.04989(11) 0.5299(2) 0.23763(13) 0.0309(4) Uani 1 1 d . . . O5 O 0.05940(9) 0.6359(2) -0.02720(13) 0.0235(3) Uani 1 1 d . . . O6 O 0.08504(12) 0.1871(3) -0.05622(16) 0.0406(4) Uani 1 1 d . . . N1 N 0.37098(10) 0.5682(2) 0.38445(13) 0.0227(4) Uani 1 1 d . . . N2 N 0.25230(10) 0.2683(2) 0.36455(13) 0.0202(3) Uani 1 1 d . . . C1 C 0.43935(12) 0.6277(3) 0.38084(18) 0.0293(5) Uani 1 1 d . . . H1A H 0.4610 0.5889 0.3245 0.035 Uiso 1 1 calc R . . C2 C 0.47918(13) 0.7434(3) 0.45639(19) 0.0332(5) Uani 1 1 d . . . H2B H 0.5273 0.7838 0.4520 0.040 Uiso 1 1 calc R . . C3 C 0.44769(13) 0.7990(3) 0.53818(19) 0.0314(5) Uani 1 1 d . . . H3B H 0.4740 0.8781 0.5913 0.038 Uiso 1 1 calc R . . C4 C 0.37750(13) 0.7386(3) 0.54206(17) 0.0278(4) Uani 1 1 d . . . H4B H 0.3551 0.7764 0.5977 0.033 Uiso 1 1 calc R . . C5 C 0.33984(11) 0.6224(3) 0.46438(16) 0.0219(4) Uani 1 1 d . . . C6 C 0.26438(12) 0.5473(3) 0.46645(17) 0.0252(4) Uani 1 1 d . . . H6B H 0.2269 0.5836 0.4004 0.030 Uiso 1 1 calc R . . H6C H 0.2484 0.5949 0.5294 0.030 Uiso 1 1 calc R . . C7 C 0.26558(12) 0.3486(3) 0.47319(16) 0.0261(4) Uani 1 1 d . . . H7A H 0.3149 0.3099 0.5178 0.031 Uiso 1 1 calc R . . H7B H 0.2263 0.3090 0.5089 0.031 Uiso 1 1 calc R . . C8 C 0.26084(13) 0.0769(3) 0.37153(17) 0.0270(4) Uani 1 1 d . . . H8A H 0.2300 0.0303 0.4188 0.032 Uiso 1 1 calc R . . H8B H 0.3141 0.0479 0.4047 0.032 Uiso 1 1 calc R . . C9 C 0.23697(12) -0.0087(3) 0.26148(17) 0.0238(4) Uani 1 1 d . . . H9A H 0.2572 -0.1285 0.2668 0.029 Uiso 1 1 calc R . . H9B H 0.2594 0.0561 0.2101 0.029 Uiso 1 1 calc R . . H1 H 0.2127(13) 0.286(3) 0.3383(18) 0.015(6) Uiso 1 1 d . . . H4E H 0.006(2) 0.540(5) 0.235(3) 0.064(11) Uiso 1 1 d . . . H4F H 0.0691(19) 0.628(5) 0.246(3) 0.052(9) Uiso 1 1 d . . . H5E H 0.0762(16) 0.712(4) 0.009(2) 0.042(9) Uiso 1 1 d . . . H5F H 0.0795(17) 0.632(4) -0.073(2) 0.040(8) Uiso 1 1 d . . . H6E H 0.089(2) 0.093(5) -0.018(3) 0.061(11) Uiso 1 1 d . . . H6F H 0.0738(19) 0.164(4) -0.110(3) 0.051(10) Uiso 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 0.01936(13) 0.02735(14) 0.01551(12) -0.00156(8) 0.00553(9) -0.00162(9) Cl1 0.0218(3) 0.0590(4) 0.0300(3) -0.0127(3) 0.0051(2) 0.0086(2) Cl2 0.0264(3) 0.0279(3) 0.0216(2) 0.00326(18) 0.00457(19) 0.0009(2) Na1 0.0239(4) 0.0275(4) 0.0209(4) 0.0028(3) 0.0037(3) 0.0012(3) S1 0.0227(2) 0.0222(2) 0.0179(2) -0.00244(18) 0.00730(19) -0.00240(19) O1 0.0261(8) 0.0272(8) 0.0241(7) -0.0049(6) 0.0022(6) 0.0042(6) O2 0.0432(10) 0.0340(9) 0.0266(8) -0.0030(6) 0.0184(7) -0.0130(7) O3 0.0317(8) 0.0280(8) 0.0200(7) -0.0046(6) 0.0077(6) -0.0048(6) O4 0.0321(10) 0.0320(9) 0.0296(8) -0.0043(7) 0.0095(7) -0.0079(8) O5 0.0250(8) 0.0274(8) 0.0180(7) -0.0020(6) 0.0052(6) -0.0049(6) O6 0.0523(12) 0.0448(12) 0.0240(9) -0.0023(8) 0.0079(8) 0.0003(9) N1 0.0202(8) 0.0286(9) 0.0197(8) -0.0022(7) 0.0055(7) -0.0037(7) N2 0.0180(9) 0.0258(9) 0.0150(8) -0.0001(6) 0.0009(7) -0.0014(7) C1 0.0248(11) 0.0353(12) 0.0296(11) -0.0012(9) 0.0101(9) -0.0051(9) C2 0.0228(11) 0.0352(13) 0.0407(13) -0.0016(10) 0.0058(10) -0.0089(9) C3 0.0320(12) 0.0262(11) 0.0324(12) -0.0043(9) 0.0006(9) -0.0070(9) C4 0.0319(11) 0.0278(11) 0.0236(10) -0.0040(8) 0.0068(9) -0.0023(9) C5 0.0219(10) 0.0252(10) 0.0188(9) 0.0008(7) 0.0051(8) -0.0016(8) C6 0.0226(10) 0.0325(11) 0.0230(10) -0.0056(8) 0.0106(8) -0.0051(9) C7 0.0282(11) 0.0346(11) 0.0173(9) -0.0023(8) 0.0089(8) -0.0099(9) C8 0.0318(12) 0.0245(10) 0.0222(10) 0.0038(8) 0.0019(9) -0.0001(9) C9 0.0227(10) 0.0231(10) 0.0252(10) -0.0005(8) 0.0052(8) 0.0008(8) _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 N1 2.0411(17) . ? Zn1 N2 2.0538(17) . ? Zn1 Cl1 2.2200(6) . ? Zn1 Cl2 2.2326(5) . ? Cl2 Na1 3.0090(10) . ? Na1 O5 2.3620(18) 3_565 ? Na1 O5 2.3705(17) . ? Na1 O1 2.3876(17) . ? Na1 O6 2.387(2) . ? Na1 O4 2.3991(18) . ? Na1 Na1 3.4715(16) 3_565 ? S1 O3 1.4561(15) . ? S1 O1 1.4582(15) . ? S1 O2 1.4599(15) . ? S1 C9 1.778(2) . ? O5 Na1 2.3620(18) 3_565 ? N1 C1 1.346(3) . ? N1 C5 1.352(3) . ? N2 C8 1.482(3) . ? N2 C7 1.484(2) . ? C1 C2 1.383(3) . ? C2 C3 1.380(3) . ? C3 C4 1.381(3) . ? C4 C5 1.388(3) . ? C5 C6 1.506(3) . ? C6 C7 1.532(3) . ? C8 C9 1.517(3) . ? 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 N1 Zn1 N2 100.12(7) . . ? N1 Zn1 Cl1 107.13(5) . . ? N2 Zn1 Cl1 114.02(5) . . ? N1 Zn1 Cl2 109.63(5) . . ? N2 Zn1 Cl2 104.42(5) . . ? Cl1 Zn1 Cl2 119.77(2) . . ? Zn1 Cl2 Na1 117.91(3) . . ? O5 Na1 O5 85.63(6) 3_565 . ? O5 Na1 O1 104.91(6) 3_565 . ? O5 Na1 O1 168.18(7) . . ? O5 Na1 O6 90.54(7) 3_565 . ? O5 Na1 O6 95.38(7) . . ? O1 Na1 O6 89.94(7) . . ? O5 Na1 O4 84.44(7) 3_565 . ? O5 Na1 O4 95.31(7) . . ? O1 Na1 O4 80.67(6) . . ? O6 Na1 O4 167.81(8) . . ? O5 Na1 Cl2 161.76(5) 3_565 . ? O5 Na1 Cl2 78.92(5) . . ? O1 Na1 Cl2 89.75(5) . . ? O6 Na1 Cl2 100.44(6) . . ? O4 Na1 Cl2 87.37(5) . . ? O5 Na1 Na1 42.91(4) 3_565 3_565 ? O5 Na1 Na1 42.72(4) . 3_565 ? O1 Na1 Na1 147.50(6) . 3_565 ? O6 Na1 Na1 94.04(6) . 3_565 ? O4 Na1 Na1 89.84(6) . 3_565 ? Cl2 Na1 Na1 121.00(4) . 3_565 ? O3 S1 O1 112.66(9) . . ? O3 S1 O2 112.95(9) . . ? O1 S1 O2 111.80(9) . . ? O3 S1 C9 105.92(10) . . ? O1 S1 C9 106.70(9) . . ? O2 S1 C9 106.20(10) . . ? S1 O1 Na1 133.60(9) . . ? Na1 O5 Na1 94.37(6) 3_565 . ? C1 N1 C5 119.33(18) . . ? C1 N1 Zn1 121.21(14) . . ? C5 N1 Zn1 119.45(14) . . ? C8 N2 C7 111.52(16) . . ? C8 N2 Zn1 115.61(14) . . ? C7 N2 Zn1 110.25(12) . . ? N1 C1 C2 122.2(2) . . ? C3 C2 C1 118.7(2) . . ? C2 C3 C4 119.3(2) . . ? C3 C4 C5 119.8(2) . . ? N1 C5 C4 120.71(19) . . ? N1 C5 C6 117.02(18) . . ? C4 C5 C6 122.24(19) . . ? C5 C6 C7 112.56(18) . . ? N2 C7 C6 111.49(17) . . ? N2 C8 C9 111.95(17) . . ? C8 C9 S1 113.59(15) . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.610 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.072