# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 1999 # CCDC Number: 440/145 #============================================================================ data_global #============================================================================ _audit_creation_method 'form.cif (version 2.0)' # PROCESSING SUMMARY (IUCr Office Use Only) _journal_data_validation_number ? _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_paper_category ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Prof.Fun Hoong Kun' _publ_contact_author_address ; X-ray Crystallography Unit School of Physics Universiti Sains Malaysia 11800 USM, Penang MALAYSIA ; _publ_contact_author_email 'hkfun@usm.my' _publ_contact_author_fax '6 04 6579150' _publ_contact_author_phone '6 04 6577888 Ext. 3690' _publ_requested_journal 'New Journal of Chemistry' _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter ; Date : 23 July 1999 Dr. Denise Parent Managing Editor CNRS, Batiment B 1919, route de Mende 34293 Montpellier cedex 5 France Ref: Paper submitted to New Journal of Chemistry Dear Sir, Attached is a CIF with the after-mentioned title and authors for the above paper which I have submitted to Dalton Transactions as a communication. Yours Sincerely, Hoong-Kun Fun ; #============================================================================ # TITLE AND AUTHOR LIST _publ_section_title ; (S-(-)-Lactate)(isonicotinato)zinc(II): Structure and Second Harmonic Generation Property if a Chiral Two-dimensional Metal-organic coordination Polymer ; loop_ _publ_author_name _publ_author_address 'Hoong-Kun Fun' ; X-ray Crystallography Unit School of Physics Universiti Sains Malaysia 11800 USM, Penang Malaysia ; 'S.Shanmuga Sundara Raj' ; X-ray Crystallography Unit School of Physics Universiti Sains Malaysia 11800 USM, Penang Malaysia ; 'Ren-Gen Xiong' ; Coordination Chemistry Institute State Key Laboratory of Coordination Chemistry Nanjing University Nanjing 210093 P.R.China ; 'Jing-Lin Zuo' ; Coordination Chemistry Institute State Key Laboratory of Coordination Chemistry Nanjing University Nanjing 210093 P.R.China ; 'Xiao-Zeng You' ; Coordination Chemistry Institute State Key Laboratory of Coordination Chemistry Nanjing University Nanjing 210093 P.R.China ; #============================================================================ _publ_section_references ; Nardelli, M. (1995). J. Appl. Cryst. 28, 659. Siemens (1996a). SMART Software Reference Manual, Siemens Analytical X-Ray Systems, Inc., Siemens (1996b). SAINT v4 Software Reference Manual, Siemens Analytical X-Ray Systems, Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (1996). SADABS. Program for Empirical Absorption Correction of Area Detector Data, University of G\"ottingen, Germany. Sheldrick, G.M. (1997). SHELXTL V5.1 Software Reference Manual, Bruker AXS, Inc., Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; The data collection was covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different \f angle (0, 88 and 180\%) for the crystal and each exposure of 30s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -35\%. Coverage of the unique set is over 99% complete. Crystal decay was monitored by repeating thirty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible. ; #============================================================================ data_xrgt18m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 N O5 Zn' _chemical_formula_weight 276.54 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 'P 21 21 21' 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 6.3480(1) _cell_length_b 9.5489(1) _cell_length_c 18.2304(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1105.06(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 1.54 _cell_measurement_theta_max 33.18 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 2.227 _exptl_absorpt_correction_type empiriacal _exptl_absorpt_correction_T_min 0.3299 _exptl_absorpt_correction_T_max 0.7171 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7227 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2524 _reflns_number_gt 2463 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996a)' _computing_cell_refinement 'SAINT (Siemens, 1996b)' _computing_data_reduction 'SAINT (Siemens, 1996b)' _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL (Sheldrick, 1997) PARST (Nardelli, 1995) ; _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^)+(0.0947P)^2^+1.5223P] 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 SHELXTL _refine_ls_extinction_coef 0.027(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 2524 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1509 _refine_ls_wR_factor_gt 0.1502 _refine_ls_goodness_of_fit_ref 1.198 _refine_ls_restrained_S_all 1.198 _refine_ls_shift/su_max 0.001 _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 1.54896(7) 0.24346(5) 0.43961(2) 0.0151(2) Uani 1 1 d . . . O1 O 1.5814(13) 0.9683(6) 0.3265(3) 0.0728(19) Uani 1 1 d . . . O2 O 1.5525(12) 1.0084(5) 0.4472(3) 0.0603(15) Uani 1 1 d . . . O3 O 1.9177(8) 0.2449(6) 0.4454(2) 0.0516(12) Uani 1 1 d . . . O4 O 1.6906(7) 0.2269(5) 0.3202(3) 0.0483(11) Uani 1 1 d . . . H4A H 1.6040 0.2142 0.2796 0.058 Uiso 1 1 calc R . . O5 O 2.2218(8) 0.2320(8) 0.3865(4) 0.0770(17) Uani 1 1 d . . . N1 N 1.5361(12) 0.4831(6) 0.4273(3) 0.0508(15) Uani 1 1 d . . . C2 C 1.5081(16) 0.5381(8) 0.3600(5) 0.059(2) Uani 1 1 d . . . H2A H 1.4782 0.4783 0.3211 0.071 Uiso 1 1 calc R . . C3 C 1.5225(15) 0.6825(7) 0.3464(4) 0.058(2) Uani 1 1 d . . . H3A H 1.5138 0.7172 0.2988 0.070 Uiso 1 1 calc R . . C4 C 1.5501(12) 0.7726(8) 0.4057(4) 0.0491(15) Uani 1 1 d . . . C5 C 1.5647(13) 0.7185(8) 0.4743(4) 0.0514(16) Uani 1 1 d . . . H5A H 1.5770 0.7776 0.5146 0.062 Uiso 1 1 calc R . . C6 C 1.5613(13) 0.5736(8) 0.4839(4) 0.0513(17) Uani 1 1 d . . . H6A H 1.5770 0.5376 0.5311 0.062 Uiso 1 1 calc R . . C7 C 1.5639(13) 0.9295(7) 0.3916(4) 0.0463(15) Uani 1 1 d . . . C8 C 2.0300(9) 0.2380(7) 0.3880(4) 0.0440(13) Uani 1 1 d . . . C9 C 1.9119(11) 0.2369(9) 0.3126(4) 0.0534(16) Uani 1 1 d . . . H9A H 1.9635 0.1590 0.2825 0.064 Uiso 1 1 calc R . . C10 C 1.9637(19) 0.3820(15) 0.2728(6) 0.113(5) Uani 1 1 d . . . H10C H 1.8941 0.3849 0.2261 0.170 Uiso 1 1 calc R . . H10B H 2.1131 0.3901 0.2657 0.170 Uiso 1 1 calc R . . H10A H 1.9150 0.4582 0.3027 0.170 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 0.0165(3) 0.0116(3) 0.0171(3) 0.0006(2) 0.00263(14) 0.0006(2) O1 0.109(6) 0.050(3) 0.060(3) -0.002(3) 0.017(4) -0.010(3) O2 0.084(4) 0.037(3) 0.060(3) -0.001(2) 0.005(4) -0.001(3) O3 0.049(2) 0.062(3) 0.043(2) -0.002(3) -0.0027(17) -0.005(3) O4 0.050(2) 0.050(3) 0.045(2) 0.000(2) -0.0090(19) -0.002(2) O5 0.043(2) 0.097(5) 0.092(4) -0.006(4) -0.014(3) 0.002(3) N1 0.060(4) 0.037(3) 0.056(3) 0.005(3) 0.009(3) 0.007(3) C2 0.075(6) 0.046(4) 0.056(4) -0.001(3) -0.006(4) -0.006(4) C3 0.085(6) 0.038(3) 0.051(4) -0.002(3) -0.013(4) 0.002(4) C4 0.051(4) 0.040(3) 0.057(4) 0.002(3) 0.000(3) 0.003(4) C5 0.062(4) 0.040(3) 0.052(4) 0.000(3) 0.001(3) -0.003(3) C6 0.061(4) 0.043(4) 0.050(4) 0.002(3) -0.005(3) -0.003(3) C7 0.050(4) 0.034(3) 0.054(4) 0.000(3) -0.001(3) -0.002(3) C8 0.039(3) 0.040(3) 0.053(3) 0.000(3) -0.003(2) -0.005(3) C9 0.049(3) 0.067(5) 0.044(3) -0.001(4) -0.003(3) 0.004(4) C10 0.079(7) 0.172(13) 0.089(7) 0.071(8) -0.011(6) -0.050(9) _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 2.249(5) 1_545 ? Zn1 O3 2.259(4) 4_456 ? Zn1 O5 2.294(5) 1_455 ? Zn1 N1 2.301(6) . ? Zn1 O3 2.343(5) . ? Zn1 O4 2.361(5) . ? O1 C7 1.249(9) . ? O2 C7 1.265(9) . ? O2 Zn1 2.249(5) 1_565 ? O3 C8 1.268(8) . ? O3 Zn1 2.259(4) 4_556 ? O4 C9 1.415(8) . ? O5 C8 1.220(8) . ? O5 Zn1 2.294(5) 1_655 ? N1 C2 1.348(10) . ? N1 C6 1.355(10) . ? C2 C3 1.403(10) . ? C3 C4 1.394(10) . ? C4 C5 1.355(12) . ? C4 C7 1.522(10) . ? C5 C6 1.396(11) . ? C8 C9 1.566(9) . ? C9 C10 1.599(13) . ? 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 O3 89.77(19) 1_545 4_456 ? O2 Zn1 O5 89.3(3) 1_545 1_455 ? O3 Zn1 O5 93.4(2) 4_456 1_455 ? O2 Zn1 N1 177.5(2) 1_545 . ? O3 Zn1 N1 91.6(2) 4_456 . ? O5 Zn1 N1 88.5(3) 1_455 . ? O2 Zn1 O3 89.6(2) 1_545 . ? O3 Zn1 O3 109.06(13) 4_456 . ? O5 Zn1 O3 157.5(2) 1_455 . ? N1 Zn1 O3 92.0(2) . . ? O2 Zn1 O4 89.19(19) 1_545 . ? O3 Zn1 O4 178.73(18) 4_456 . ? O5 Zn1 O4 87.3(2) 1_455 . ? N1 Zn1 O4 89.4(2) . . ? O3 Zn1 O4 70.21(15) . . ? C7 O2 Zn1 123.1(5) . 1_565 ? C8 O3 Zn1 124.1(4) . 4_556 ? C8 O3 Zn1 121.6(4) . . ? Zn1 O3 Zn1 114.2(2) 4_556 . ? C9 O4 Zn1 117.7(4) . . ? C8 O5 Zn1 153.2(6) . 1_655 ? C2 N1 C6 117.4(6) . . ? C2 N1 Zn1 118.8(5) . . ? C6 N1 Zn1 123.7(5) . . ? N1 C2 C3 122.4(7) . . ? C4 C3 C2 118.5(7) . . ? C5 C4 C3 119.3(7) . . ? C5 C4 C7 121.8(7) . . ? C3 C4 C7 118.9(7) . . ? C4 C5 C6 119.6(8) . . ? N1 C6 C5 122.5(7) . . ? O1 C7 O2 126.2(7) . . ? O1 C7 C4 117.3(7) . . ? O2 C7 C4 116.6(7) . . ? O5 C8 O3 125.6(7) . . ? O5 C8 C9 117.3(7) . . ? O3 C8 C9 117.1(5) . . ? O4 C9 C8 112.9(6) . . ? O4 C9 C10 107.9(7) . . ? C8 C9 C10 107.1(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Zn1 O3 C8 89.8(5) 1_545 . . . ? O3 Zn1 O3 C8 179.4(6) 4_456 . . . ? O5 Zn1 O3 C8 2.7(10) 1_455 . . . ? N1 Zn1 O3 C8 -88.2(5) . . . . ? O4 Zn1 O3 C8 0.5(5) . . . . ? O2 Zn1 O3 Zn1 -89.5(2) 1_545 . . 4_556 ? O3 Zn1 O3 Zn1 0.15(11) 4_456 . . 4_556 ? O5 Zn1 O3 Zn1 -176.6(5) 1_455 . . 4_556 ? N1 Zn1 O3 Zn1 92.5(3) . . . 4_556 ? O4 Zn1 O3 Zn1 -178.7(3) . . . 4_556 ? O2 Zn1 O4 C9 -94.5(6) 1_545 . . . ? O3 Zn1 O4 C9 -60(8) 4_456 . . . ? O5 Zn1 O4 C9 176.2(6) 1_455 . . . ? N1 Zn1 O4 C9 87.6(6) . . . . ? O3 Zn1 O4 C9 -4.7(6) . . . . ? O2 Zn1 N1 C2 -28(6) 1_545 . . . ? O3 Zn1 N1 C2 -150.7(7) 4_456 . . . ? O5 Zn1 N1 C2 -57.3(7) 1_455 . . . ? O3 Zn1 N1 C2 100.1(7) . . . . ? O4 Zn1 N1 C2 30.0(7) . . . . ? O2 Zn1 N1 C6 154(5) 1_545 . . . ? O3 Zn1 N1 C6 31.3(7) 4_456 . . . ? O5 Zn1 N1 C6 124.7(7) 1_455 . . . ? O3 Zn1 N1 C6 -77.9(7) . . . . ? O4 Zn1 N1 C6 -148.0(7) . . . . ? C6 N1 C2 C3 5.6(15) . . . . ? Zn1 N1 C2 C3 -172.5(7) . . . . ? N1 C2 C3 C4 -5.2(15) . . . . ? C2 C3 C4 C5 0.8(13) . . . . ? C2 C3 C4 C7 -179.5(8) . . . . ? C3 C4 C5 C6 2.8(11) . . . . ? C7 C4 C5 C6 -176.9(8) . . . . ? C2 N1 C6 C5 -1.8(13) . . . . ? Zn1 N1 C6 C5 176.3(6) . . . . ? C4 C5 C6 N1 -2.4(13) . . . . ? Zn1 O2 C7 O1 2.5(13) 1_565 . . . ? Zn1 O2 C7 C4 -176.1(5) 1_565 . . . ? C5 C4 C7 O1 169.2(8) . . . . ? C3 C4 C7 O1 -10.5(12) . . . . ? C5 C4 C7 O2 -12.0(11) . . . . ? C3 C4 C7 O2 168.2(8) . . . . ? Zn1 O5 C8 O3 -10(2) 1_655 . . . ? Zn1 O5 C8 C9 170.3(11) 1_655 . . . ? Zn1 O3 C8 O5 2.6(11) 4_556 . . . ? Zn1 O3 C8 O5 -176.6(7) . . . . ? Zn1 O3 C8 C9 -177.5(5) 4_556 . . . ? Zn1 O3 C8 C9 3.3(8) . . . . ? Zn1 O4 C9 C8 7.6(9) . . . . ? Zn1 O4 C9 C10 -110.6(6) . . . . ? O5 C8 C9 O4 172.7(8) . . . . ? O3 C8 C9 O4 -7.2(10) . . . . ? O5 C8 C9 C10 -68.6(10) . . . . ? O3 C8 C9 C10 111.4(8) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.382 _refine_diff_density_min -0.828 _refine_diff_density_rms 0.159 #============================================================================ # END OF CIF