# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Janusz Lewinski' _publ_contact_author_address ; Janusz Lewinski Department of Chemistry Warsaw University of Technology Noakowskiego 3, PL-00-664 Warszawa Poland ; _publ_contact_author_phone '048 22 6607315' _publ_contact_author_fax '048 22 6607279' _publ_contact_author_email lewin@ch.pw.edu.pl #========================================================= # 2. TITLE AND AUTHOR LIST _publ_section_title ; Divergent Coordination Mode of Magnesium and Zinc Akyls Supported by Pyrrolylaldiminate ligand. ; loop_ _publ_author_name _publ_author_address 'Janusz Lewinski' ; Department of Chemistry Warsaw University of Technology Noakowskiego 3, PL-00-664 Warszawa Poland e-mail: lewin@ch.pw.edu.pl ; 'Maciej Dranka' ; Department of Chemistry Warsaw University of Technology Noakowskiego 3, PL-00-664 Warszawa Poland ; 'Izabela Kraszewska' ; Department of Chemistry Warsaw University of Technology Noakowskiego 3, PL-00-664 Warszawa Poland ; 'Witold Sliwinski' ; Department of Chemistry Warsaw University of Technology Noakowskiego 3, PL-00-664 Warszawa Poland ; 'Iwona Justyniak' ; Institute of Physical Chemistry, Polish Academy of Sciences Kasprzaka 44/52, PL-01-224 Warszawa Poland ; #========================================================= # 1. SUBMISSION DETAILS _publ_contact_author ; Dr. Janusz Lewinski, Department of Chemistry Warsaw University of Technology Noakowskiego 3, PL-00-664 Warszawa Poland ; #============================================================ # 3. data compound [mg(pyrpr)]2 data_comp1 _database_code_depnum_ccdc_archive 'CCDC 277419' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H40 Mg2 N4' _chemical_formula_weight 433.22 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' Mg Mg 0.0486 0.0363 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5297(7) _cell_length_b 8.9152(8) _cell_length_c 9.5123(9) _cell_angle_alpha 88.853(5) _cell_angle_beta 82.971(7) _cell_angle_gamma 64.670(6) _cell_volume 648.47(10) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1549 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 21.97 _exptl_crystal_description prism _exptl_crystal_colour white _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.109 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 236 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 '\k-geometry diffractometr' _diffrn_measurement_device_type 'Nonius Kappa-CCD' _diffrn_measurement_method 'area detector \w scans' _diffrn_measurement_details ; 242 frames, \w rotation 1.5\% per frame (180s per frame) 34 frames, \w rotation 1.5\% per frame (180s per frame) 21 frames, \w rotation 1.5\% per frame (180s per frame) 33 frames, \w rotation 1.5\% per frame (180s per frame) 23 frames, \w rotation 1.5\% per frame (180s per frame) ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3049 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 22.00 _reflns_number_total 1566 _reflns_number_gt 1414 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'Denzo & Scalepak (Otwinowski, Minor, 1997)' _computing_data_reduction 'Denzo & Scalepak (Otwinowski, Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows, L.J.Farrugia (1997) J.Appl.Cryst. 30, 565, ORTEP III (Burnett, Johnson, 1996) ; _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PLATON, A.L.Spek (2000) Utrecht Univ., Utrecht, The Netherlands ; _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^)+(0.0532P)^2^+0.3215P] 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 1566 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1116 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 Mg1 Mg 0.07233(9) 0.05748(9) 0.36902(8) 0.0271(3) Uani 1 1 d . . . N1 N 0.1255(2) 0.0404(2) 0.5861(2) 0.0266(5) Uani 1 1 d . . . N2 N 0.3196(2) -0.1555(2) 0.3427(2) 0.0301(5) Uani 1 1 d . . . C1 C 0.0909(3) 0.1372(3) 0.7069(3) 0.0320(6) Uani 1 1 d . . . H1 H -0.0196 0.2256 0.7379 0.038 Uiso 1 1 calc R . . C2 C 0.2341(3) 0.0911(3) 0.7771(3) 0.0346(6) Uani 1 1 d . . . H2 H 0.2403 0.1391 0.8633 0.042 Uiso 1 1 calc R . . C3 C 0.3699(3) -0.0407(3) 0.6971(3) 0.0336(6) Uani 1 1 d . . . H3 H 0.4863 -0.0995 0.7186 0.040 Uiso 1 1 calc R . . C4 C 0.3027(3) -0.0692(3) 0.5813(3) 0.0292(6) Uani 1 1 d . . . C5 C 0.3928(3) -0.1694(3) 0.4570(3) 0.0311(6) Uani 1 1 d . . . H5 H 0.5103 -0.2492 0.4577 0.037 Uiso 1 1 calc R . . C6 C 0.4294(3) -0.2611(3) 0.2173(3) 0.0330(6) Uani 1 1 d . . . H6 H 0.5544 -0.2890 0.2261 0.040 Uiso 1 1 calc R . . C7 C 0.4095(3) -0.4228(3) 0.2124(3) 0.0409(7) Uani 1 1 d . . . H7A H 0.4304 -0.4763 0.3036 0.061 Uiso 1 1 calc R . . H7B H 0.4945 -0.4970 0.1368 0.061 Uiso 1 1 calc R . . H7C H 0.2909 -0.3990 0.1935 0.061 Uiso 1 1 calc R . . C8 C 0.3824(3) -0.1635(3) 0.0853(3) 0.0398(7) Uani 1 1 d . . . H8A H 0.2606 -0.1362 0.0740 0.060 Uiso 1 1 calc R . . H8B H 0.4593 -0.2301 0.0027 0.060 Uiso 1 1 calc R . . H8C H 0.3967 -0.0608 0.0936 0.060 Uiso 1 1 calc R . . C9 C -0.0060(3) 0.2866(3) 0.2640(3) 0.0312(6) Uani 1 1 d . . . C10 C 0.1421(3) 0.3366(3) 0.2161(3) 0.0432(7) Uani 1 1 d . . . H10A H 0.2283 0.2537 0.1466 0.065 Uiso 1 1 calc R . . H10B H 0.1984 0.3429 0.2982 0.065 Uiso 1 1 calc R . . H10C H 0.0945 0.4453 0.1729 0.065 Uiso 1 1 calc R . . C11 C -0.0966(3) 0.2868(3) 0.1354(3) 0.0389(7) Uani 1 1 d . . . H11A H -0.1409 0.3975 0.0956 0.058 Uiso 1 1 calc R . . H11B H -0.1942 0.2578 0.1642 0.058 Uiso 1 1 calc R . . H11C H -0.0129 0.2052 0.0637 0.058 Uiso 1 1 calc R . . C12 C -0.1379(3) 0.4206(3) 0.3716(3) 0.0382(7) Uani 1 1 d . . . H12A H -0.1762 0.5295 0.3289 0.057 Uiso 1 1 calc R . . H12B H -0.0825 0.4212 0.4559 0.057 Uiso 1 1 calc R . . H12C H -0.2392 0.3967 0.3989 0.057 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 Mg1 0.0279(5) 0.0231(5) 0.0282(5) 0.0019(3) -0.0037(3) -0.0089(4) N1 0.0263(11) 0.0232(11) 0.0283(12) 0.0003(9) -0.0043(8) -0.0084(9) N2 0.0303(11) 0.0273(11) 0.0326(13) -0.0017(9) -0.0001(10) -0.0132(9) C1 0.0356(15) 0.0286(13) 0.0333(15) -0.0015(11) -0.0020(12) -0.0159(11) C2 0.0402(15) 0.0393(15) 0.0304(15) -0.0033(12) -0.0041(12) -0.0227(13) C3 0.0307(14) 0.0367(15) 0.0349(16) 0.0040(12) -0.0069(12) -0.0155(12) C4 0.0327(15) 0.0272(13) 0.0297(15) 0.0043(11) -0.0055(11) -0.0145(12) C5 0.0309(14) 0.0253(13) 0.0368(16) 0.0038(11) -0.0054(12) -0.0115(11) C6 0.0307(14) 0.0293(14) 0.0352(16) -0.0046(11) -0.0017(11) -0.0096(11) C7 0.0383(15) 0.0310(14) 0.0496(18) -0.0073(13) 0.0002(12) -0.0123(12) C8 0.0481(16) 0.0368(15) 0.0331(16) -0.0038(12) -0.0011(12) -0.0177(13) C9 0.0300(14) 0.0258(13) 0.0379(15) 0.0033(11) -0.0050(11) -0.0118(11) C10 0.0403(16) 0.0323(15) 0.0578(19) 0.0116(13) -0.0097(13) -0.0158(12) C11 0.0365(15) 0.0393(15) 0.0395(17) 0.0063(12) -0.0062(12) -0.0148(12) C12 0.0382(15) 0.0289(14) 0.0448(17) 0.0019(12) -0.0071(12) -0.0112(12) _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 Mg1 C9 2.129(2) . ? Mg1 N2 2.140(2) . ? Mg1 N1 2.156(2) . ? Mg1 N1 2.204(2) 2_556 ? Mg1 C1 2.799(2) 2_556 ? Mg1 C5 2.833(2) . ? Mg1 C4 2.862(2) . ? Mg1 Mg1 3.0015(15) 2_556 ? N1 C1 1.376(3) . ? N1 C4 1.401(3) . ? N1 Mg1 2.204(2) 2_556 ? N2 C5 1.297(3) . ? N2 C6 1.484(3) . ? C1 C2 1.366(3) . ? C1 Mg1 2.799(2) 2_556 ? C1 H1 0.9500 . ? C2 C3 1.399(3) . ? C2 H2 0.9500 . ? C3 C4 1.377(3) . ? C3 H3 0.9500 . ? C4 C5 1.420(3) . ? C5 H5 0.9500 . ? C6 C8 1.508(4) . ? C6 C7 1.524(3) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C11 1.525(3) . ? C9 C10 1.528(3) . ? C9 C12 1.536(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? 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 C9 Mg1 N2 128.91(9) . . ? C9 Mg1 N1 121.15(9) . . ? N2 Mg1 N1 81.71(8) . . ? C9 Mg1 N1 116.60(8) . 2_556 ? N2 Mg1 N1 105.70(7) . 2_556 ? N1 Mg1 N1 93.01(7) . 2_556 ? C9 Mg1 C1 113.53(9) . 2_556 ? N2 Mg1 C1 90.04(7) . 2_556 ? N1 Mg1 C1 115.16(8) . 2_556 ? N1 Mg1 C1 28.92(7) 2_556 2_556 ? C9 Mg1 C5 133.56(8) . . ? N2 Mg1 C5 25.72(7) . . ? N1 Mg1 C5 56.67(7) . . ? N1 Mg1 C5 109.77(7) 2_556 . ? C1 Mg1 C5 105.42(7) 2_556 . ? C9 Mg1 C4 129.75(8) . . ? N2 Mg1 C4 54.48(7) . . ? N1 Mg1 C4 28.19(7) . . ? N1 Mg1 C4 106.07(7) 2_556 . ? C1 Mg1 C4 116.65(7) 2_556 . ? C5 Mg1 C4 28.88(7) . . ? C9 Mg1 Mg1 134.46(8) . 2_556 ? N2 Mg1 Mg1 95.46(6) . 2_556 ? N1 Mg1 Mg1 47.18(5) . 2_556 ? N1 Mg1 Mg1 45.83(5) 2_556 2_556 ? C1 Mg1 Mg1 70.27(6) 2_556 2_556 ? C5 Mg1 Mg1 81.59(6) . 2_556 ? C4 Mg1 Mg1 64.54(5) . 2_556 ? C1 N1 C4 104.08(18) . . ? C1 N1 Mg1 141.35(16) . . ? C4 N1 Mg1 105.19(14) . . ? C1 N1 Mg1 100.29(14) . 2_556 ? C4 N1 Mg1 118.99(14) . 2_556 ? Mg1 N1 Mg1 86.99(7) . 2_556 ? C5 N2 C6 117.25(19) . . ? C5 N2 Mg1 108.52(15) . . ? C6 N2 Mg1 132.94(16) . . ? C2 C1 N1 112.0(2) . . ? C2 C1 Mg1 128.33(17) . 2_556 ? N1 C1 Mg1 50.79(11) . 2_556 ? C2 C1 H1 124.0 . . ? N1 C1 H1 124.0 . . ? Mg1 C1 H1 90.6 2_556 . ? C1 C2 C3 106.5(2) . . ? C1 C2 H2 126.7 . . ? C3 C2 H2 126.7 . . ? C4 C3 C2 107.0(2) . . ? C4 C3 H3 126.5 . . ? C2 C3 H3 126.5 . . ? C3 C4 N1 110.4(2) . . ? C3 C4 C5 129.0(2) . . ? N1 C4 C5 119.8(2) . . ? C3 C4 Mg1 149.37(17) . . ? N1 C4 Mg1 46.62(11) . . ? C5 C4 Mg1 74.40(14) . . ? N2 C5 C4 122.1(2) . . ? N2 C5 Mg1 45.76(11) . . ? C4 C5 Mg1 76.72(14) . . ? N2 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? Mg1 C5 H5 163.3 . . ? N2 C6 C8 109.06(19) . . ? N2 C6 C7 110.7(2) . . ? C8 C6 C7 112.5(2) . . ? N2 C6 H6 108.2 . . ? C8 C6 H6 108.2 . . ? C7 C6 H6 108.2 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C9 C10 108.1(2) . . ? C11 C9 C12 108.28(19) . . ? C10 C9 C12 107.5(2) . . ? C11 C9 Mg1 111.89(16) . . ? C10 C9 Mg1 114.59(16) . . ? C12 C9 Mg1 106.26(16) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 22.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.239 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.039 #============================================================ # 3. data compound tBuzn(pyrpr) data_shelxl _database_code_depnum_ccdc_archive 'CCDC 277420' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 N2 Zn1' _chemical_formula_weight 257.69 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' Zn Zn 0.2839 1.4301 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 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 12.8805(7) _cell_length_b 8.8359(5) _cell_length_c 11.8961(6) _cell_angle_alpha 90.00 _cell_angle_beta 107.715(3) _cell_angle_gamma 90.00 _cell_volume 1289.71(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2130 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 24.11 _exptl_crystal_description prism _exptl_crystal_colour white _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 1.876 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'Scalepak (Otwinowski, Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 '\k-geometry diffractometr' _diffrn_measurement_device_type 'Nonius Kappa-CCD' _diffrn_measurement_method 'area detector \w scans' _diffrn_measurement_details ; 141 frames, \w rotation 1.5\% per frame (180s per frame) 21 frames, \w rotation 1.5\% per frame (180s per frame) 68 frames, \w rotation 1.5\% per frame (180s per frame) ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3732 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 24.00 _reflns_number_total 2007 _reflns_number_gt 1789 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'Denzo & Scalepak (Otwinowski, Minor, 1997)' _computing_data_reduction 'Denzo & Scalepak (Otwinowski, Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Ortep-3 for Windows, L.J.Farrugia (1997) J.Appl.Cryst. 30, 565, ORTEP III (Burnett, Johnson, 1996) ; _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PLATON, A.L.Spek (2000) Utrecht Univ., Utrecht, The Netherlands ; _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^)+(0.0337P)^2^+1.4900P] 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 2007 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0786 _refine_ls_wR_factor_gt 0.0761 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.70464(3) 0.01837(4) 0.55812(3) 0.02154(14) Uani 1 1 d . . . N1 N 0.57640(19) 0.0844(3) 0.60674(19) 0.0195(5) Uani 1 1 d . . . N2 N 0.6804(2) 0.2288(3) 0.4740(2) 0.0215(6) Uani 1 1 d . . . C1 C 0.5042(3) 0.0320(3) 0.6600(2) 0.0233(7) Uani 1 1 d . . . H1 H 0.5132 -0.0584 0.7053 0.028 Uiso 1 1 calc R . . C2 C 0.4150(2) 0.1290(3) 0.6390(3) 0.0245(7) Uani 1 1 d . . . H2 H 0.3532 0.1167 0.6659 0.029 Uiso 1 1 calc R . . C3 C 0.4346(2) 0.2480(3) 0.5705(3) 0.0254(7) Uani 1 1 d . . . H3 H 0.3891 0.3332 0.5423 0.031 Uiso 1 1 calc R . . C4 C 0.5336(2) 0.2168(3) 0.5521(3) 0.0220(7) Uani 1 1 d . . . C5 C 0.5932(2) 0.2907(3) 0.4838(3) 0.0230(7) Uani 1 1 d . . . H5 H 0.5685 0.3845 0.4461 0.028 Uiso 1 1 calc R . . C6 C 0.7464(3) 0.3063(4) 0.4094(3) 0.0258(7) Uani 1 1 d . . . H6 H 0.7042 0.3943 0.3655 0.031 Uiso 1 1 calc R . . C7 C 0.8503(3) 0.3642(4) 0.4980(3) 0.0342(8) Uani 1 1 d . . . H7A H 0.8317 0.4316 0.5545 0.051 Uiso 1 1 calc R . . H7B H 0.8933 0.4199 0.4565 0.051 Uiso 1 1 calc R . . H7C H 0.8928 0.2784 0.5404 0.051 Uiso 1 1 calc R . . C8 C 0.7687(3) 0.1964(4) 0.3216(3) 0.0303(8) Uani 1 1 d . . . H8A H 0.8082 0.1084 0.3637 0.045 Uiso 1 1 calc R . . H8B H 0.8128 0.2465 0.2784 0.045 Uiso 1 1 calc R . . H8C H 0.6994 0.1633 0.2658 0.045 Uiso 1 1 calc R . . C9 C 0.8335(2) -0.1144(3) 0.6251(2) 0.0230(7) Uani 1 1 d . . . C10 C 0.8051(3) -0.2265(4) 0.7084(3) 0.0397(9) Uani 1 1 d . . . H10A H 0.7439 -0.2898 0.6639 0.059 Uiso 1 1 calc R . . H10B H 0.7847 -0.1711 0.7699 0.059 Uiso 1 1 calc R . . H10C H 0.8684 -0.2907 0.7450 0.059 Uiso 1 1 calc R . . C11 C 0.9331(3) -0.0224(4) 0.6947(3) 0.0392(9) Uani 1 1 d . . . H11A H 0.9152 0.0351 0.7568 0.059 Uiso 1 1 calc R . . H11B H 0.9539 0.0476 0.6414 0.059 Uiso 1 1 calc R . . H11C H 0.9939 -0.0912 0.7306 0.059 Uiso 1 1 calc R . . C12 C 0.8661(3) -0.2022(4) 0.5307(3) 0.0304(8) Uani 1 1 d . . . H12A H 0.9283 -0.2678 0.5685 0.046 Uiso 1 1 calc R . . H12B H 0.8863 -0.1311 0.4777 0.046 Uiso 1 1 calc R . . H12C H 0.8046 -0.2644 0.4853 0.046 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 0.0183(2) 0.0233(2) 0.0226(2) 0.00173(15) 0.00547(15) 0.00251(15) N1 0.0191(13) 0.0217(13) 0.0170(12) -0.0042(10) 0.0044(10) -0.0029(11) N2 0.0210(14) 0.0202(13) 0.0214(13) 0.0022(10) 0.0037(11) -0.0020(11) C1 0.0288(18) 0.0225(15) 0.0176(14) -0.0054(12) 0.0057(13) -0.0025(13) C2 0.0200(17) 0.0281(17) 0.0276(16) -0.0074(14) 0.0105(14) -0.0031(13) C3 0.0219(17) 0.0209(16) 0.0323(17) -0.0053(13) 0.0063(14) 0.0009(13) C4 0.0242(17) 0.0172(15) 0.0233(15) -0.0049(13) 0.0051(13) -0.0011(13) C5 0.0222(17) 0.0180(15) 0.0252(16) -0.0005(12) 0.0020(13) -0.0017(13) C6 0.0231(17) 0.0287(17) 0.0261(17) 0.0057(13) 0.0080(14) -0.0028(14) C7 0.0284(19) 0.0366(19) 0.0379(19) 0.0007(16) 0.0103(16) -0.0104(16) C8 0.035(2) 0.0311(18) 0.0277(17) 0.0036(14) 0.0135(15) -0.0041(15) C9 0.0214(17) 0.0280(17) 0.0202(15) 0.0005(13) 0.0070(13) 0.0056(13) C10 0.039(2) 0.048(2) 0.0334(19) 0.0175(17) 0.0127(17) 0.0179(18) C11 0.0228(19) 0.046(2) 0.041(2) -0.0121(17) -0.0017(16) 0.0071(16) C12 0.0266(18) 0.0355(19) 0.0291(17) 0.0002(14) 0.0087(15) 0.0086(15) _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 C9 1.990(3) . ? Zn1 N1 1.996(2) . ? Zn1 N2 2.089(2) . ? N1 C1 1.356(4) . ? N1 C4 1.370(4) . ? N2 C5 1.286(4) . ? N2 C6 1.477(4) . ? C1 C2 1.394(4) . ? C1 H1 0.9500 . ? C2 C3 1.400(4) . ? C2 H2 0.9500 . ? C3 C4 1.386(4) . ? C3 H3 0.9500 . ? C4 C5 1.434(4) . ? C5 H5 0.9500 . ? C6 C8 1.517(4) . ? C6 C7 1.518(4) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.523(4) . ? C9 C12 1.525(4) . ? C9 C11 1.531(4) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? 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 C9 Zn1 N1 135.99(10) . . ? C9 Zn1 N2 134.50(11) . . ? N1 Zn1 N2 82.10(9) . . ? C1 N1 C4 106.2(2) . . ? C1 N1 Zn1 141.4(2) . . ? C4 N1 Zn1 111.16(18) . . ? C5 N2 C6 120.5(2) . . ? C5 N2 Zn1 110.01(19) . . ? C6 N2 Zn1 129.52(19) . . ? N1 C1 C2 110.6(3) . . ? N1 C1 H1 124.7 . . ? C2 C1 H1 124.7 . . ? C1 C2 C3 106.3(3) . . ? C1 C2 H2 126.8 . . ? C3 C2 H2 126.8 . . ? C4 C3 C2 106.3(3) . . ? C4 C3 H3 126.9 . . ? C2 C3 H3 126.9 . . ? N1 C4 C3 110.6(3) . . ? N1 C4 C5 116.8(3) . . ? C3 C4 C5 132.5(3) . . ? N2 C5 C4 119.4(3) . . ? N2 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? N2 C6 C8 108.7(2) . . ? N2 C6 C7 108.6(2) . . ? C8 C6 C7 112.5(3) . . ? N2 C6 H6 109.0 . . ? C8 C6 H6 109.0 . . ? C7 C6 H6 109.0 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C12 108.8(3) . . ? C10 C9 C11 108.7(3) . . ? C12 C9 C11 107.2(3) . . ? C10 C9 Zn1 107.9(2) . . ? C12 C9 Zn1 112.9(2) . . ? C11 C9 Zn1 111.3(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.870 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.062