# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Ali Morsali' _publ_contact_author_email 'MORSALI A@YAHOO.COM' _publ_section_title ; Solid State Crystal-to-Crystal Transformation From Monomeric Structure to One-dimensional Coordination Polymers on Anion Exchange ; loop_ _publ_author_name 'Ali Morsali' 'Mojtaba Khanpour' # Attachment 'CCDC-01082m-revised.cif' data_01082m _database_code_depnum_ccdc_archive 'CCDC 723323' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H36 N8 O4 Zn, 2(C14 H14 N4), 2( N O3 )' _chemical_formula_sum 'C56 H64 N18 O10 Zn' _chemical_formula_weight 1214.62 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 8.7682(12) _cell_length_b 22.742(3) _cell_length_c 14.533(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.819(2) _cell_angle_gamma 90.00 _cell_volume 2896.5(7) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3670 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 25.02 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 0.499 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8608 _exptl_absorpt_correction_T_max 0.8771 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _diffrn_ambient_temperature 298(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 APEX area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15072 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5104 _reflns_number_gt 4472 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Bruker, 2002)' _computing_publication_material 'SHELXL-97 (Bruker, 2002)' _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^)+(0.0488P)^2^+2.1689P] 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 5104 _refine_ls_number_parameters 401 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1279 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.152 _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 0.5000 0.5000 1.0000 0.02563(15) Uani 1 2 d S . . O1 O 0.4149(2) 0.57079(9) 1.07288(15) 0.0359(5) Uani 1 1 d D . . O2 O 0.2939(2) 0.45554(9) 1.01115(16) 0.0339(5) Uani 1 1 d D . . O3 O 0.8509(3) 0.43596(13) 0.83447(18) 0.0620(8) Uani 1 1 d . . . O4 O 0.9491(3) 0.41226(17) 0.9652(2) 0.0857(11) Uani 1 1 d . . . O5 O 1.0907(3) 0.44868(11) 0.86169(17) 0.0493(6) Uani 1 1 d . . . N1 N -0.4406(3) 0.84873(12) 0.6919(2) 0.0459(7) Uani 1 1 d . . . N2 N -0.0820(3) 0.69463(12) 0.7320(2) 0.0408(7) Uani 1 1 d . . . N3 N 0.0705(3) 0.67552(11) 0.74128(19) 0.0388(6) Uani 1 1 d . . . N4 N 0.4254(3) 0.54288(10) 0.87049(16) 0.0280(5) Uani 1 1 d . . . N5 N 0.3119(3) 0.33411(12) 0.0411(2) 0.0432(7) Uani 1 1 d . . . N6 N 0.6504(3) 0.17237(12) 0.0139(2) 0.0452(7) Uani 1 1 d . . . N7 N 0.8002(3) 0.15182(13) 0.0089(2) 0.0462(7) Uani 1 1 d . . . N8 N 1.2120(4) 0.06927(15) -0.0355(3) 0.0624(9) Uani 1 1 d . . . N9 N 0.9638(3) 0.43254(12) 0.88827(19) 0.0385(6) Uani 1 1 d . . . C1 C -0.5528(4) 0.81139(15) 0.7078(2) 0.0430(8) Uani 1 1 d . . . H1 H -0.6526 0.8251 0.7030 0.052 Uiso 1 1 calc R . . C2 C -0.5294(4) 0.75362(15) 0.7312(2) 0.0433(8) Uani 1 1 d . . . H2 H -0.6116 0.7289 0.7417 0.052 Uiso 1 1 calc R . . C3 C -0.3827(4) 0.73289(14) 0.7387(2) 0.0395(8) Uani 1 1 d . . . H3 H -0.3644 0.6937 0.7539 0.047 Uiso 1 1 calc R . . C4 C -0.2619(3) 0.77067(13) 0.7237(2) 0.0313(7) Uani 1 1 d . . . C5 C -0.2984(4) 0.82825(14) 0.7011(2) 0.0393(8) Uani 1 1 d . . . H5 H -0.2186 0.8543 0.6918 0.047 Uiso 1 1 calc R . . C6 C -0.1014(3) 0.75004(14) 0.7319(2) 0.0333(7) Uani 1 1 d . . . C7 C 0.0235(4) 0.79430(18) 0.7432(4) 0.0822(16) Uani 1 1 d . . . H7A H 0.1185 0.7745 0.7560 0.123 Uiso 1 1 calc R . . H7B H 0.0017 0.8202 0.7934 0.123 Uiso 1 1 calc R . . H7C H 0.0306 0.8167 0.6876 0.123 Uiso 1 1 calc R . . C8 C -0.0473(4) 0.58564(15) 0.8023(3) 0.0477(9) Uani 1 1 d . . . H8A H -0.0485 0.5837 0.8682 0.072 Uiso 1 1 calc R . . H8B H -0.0351 0.5468 0.7778 0.072 Uiso 1 1 calc R . . H8C H -0.1417 0.6021 0.7790 0.072 Uiso 1 1 calc R . . C9 C 0.0820(3) 0.62336(13) 0.7741(2) 0.0312(7) Uani 1 1 d . . . C10 C 0.2393(3) 0.59855(12) 0.7819(2) 0.0287(6) Uani 1 1 d . . . C11 C 0.3430(4) 0.60497(13) 0.7121(2) 0.0362(7) Uani 1 1 d . . . H11 H 0.3166 0.6263 0.6594 0.043 Uiso 1 1 calc R . . C12 C 0.4848(4) 0.57947(14) 0.7217(2) 0.0387(8) Uani 1 1 d . . . H12 H 0.5548 0.5830 0.6752 0.046 Uiso 1 1 calc R . . C13 C 0.5219(3) 0.54863(13) 0.8010(2) 0.0335(7) Uani 1 1 d . . . H13 H 0.6176 0.5311 0.8066 0.040 Uiso 1 1 calc R . . C14 C 0.2870(3) 0.56718(12) 0.8598(2) 0.0293(7) Uani 1 1 d . . . H14 H 0.2189 0.5628 0.9071 0.035 Uiso 1 1 calc R . . C15 C 0.1939(4) 0.29794(15) 0.0317(2) 0.0445(8) Uani 1 1 d . . . H15 H 0.0962 0.3135 0.0354 0.053 Uiso 1 1 calc R . . C16 C 0.2087(4) 0.23868(15) 0.0169(3) 0.0490(9) Uani 1 1 d . . . H16 H 0.1228 0.2148 0.0107 0.059 Uiso 1 1 calc R . . C17 C 0.3521(4) 0.21512(15) 0.0113(2) 0.0445(8) Uani 1 1 d . . . H17 H 0.3643 0.1751 0.0010 0.053 Uiso 1 1 calc R . . C18 C 0.4789(3) 0.25134(13) 0.0211(2) 0.0340(7) Uani 1 1 d . . . C19 C 0.4510(4) 0.31045(14) 0.0359(2) 0.0379(8) Uani 1 1 d . . . H19 H 0.5346 0.3354 0.0428 0.046 Uiso 1 1 calc R . . C20 C 0.6359(4) 0.22839(14) 0.0170(2) 0.0390(8) Uani 1 1 d . . . C21 C 0.7681(4) 0.27007(18) 0.0190(4) 0.0722(13) Uani 1 1 d . . . H21A H 0.7962 0.2794 0.0816 0.108 Uiso 1 1 calc R . . H21B H 0.7398 0.3054 -0.0134 0.108 Uiso 1 1 calc R . . H21C H 0.8531 0.2521 -0.0101 0.108 Uiso 1 1 calc R . . C22 C 0.7211(4) 0.07844(17) 0.1226(3) 0.0571(10) Uani 1 1 d . . . H22A H 0.7376 0.0941 0.1834 0.086 Uiso 1 1 calc R . . H22B H 0.7370 0.0367 0.1237 0.086 Uiso 1 1 calc R . . H22C H 0.6185 0.0867 0.1015 0.086 Uiso 1 1 calc R . . C23 C 0.8304(4) 0.10620(15) 0.0589(2) 0.0400(8) Uani 1 1 d . . . C24 C 0.9869(4) 0.08294(14) 0.0533(2) 0.0400(8) Uani 1 1 d . . . C25 C 1.0597(5) 0.05722(16) 0.1287(3) 0.0534(10) Uani 1 1 d . . . H25 H 1.0089 0.0522 0.1834 0.064 Uiso 1 1 calc R . . C26 C 1.2084(5) 0.03918(18) 0.1217(3) 0.0663(12) Uani 1 1 d . . . H26 H 1.2607 0.0228 0.1722 0.080 Uiso 1 1 calc R . . C27 C 1.2785(5) 0.04569(18) 0.0398(4) 0.0672(12) Uani 1 1 d . . . H27 H 1.3788 0.0329 0.0361 0.081 Uiso 1 1 calc R . . C28 C 1.0695(4) 0.08745(15) -0.0264(3) 0.0492(9) Uani 1 1 d . . . H28 H 1.0210 0.1046 -0.0776 0.059 Uiso 1 1 calc R . . H1A H 0.474(3) 0.5872(16) 1.111(2) 0.059 Uiso 1 1 d D . . H2A H 0.229(3) 0.4582(14) 0.9671(19) 0.059 Uiso 1 1 d D . . H1B H 0.326(2) 0.5682(16) 1.091(2) 0.059 Uiso 1 1 d D . . H2B H 0.303(4) 0.4211(10) 1.029(2) 0.059 Uiso 1 1 d 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(2) 0.0219(3) 0.0335(3) 0.0009(2) -0.00358(18) 0.00050(19) O1 0.0253(11) 0.0310(12) 0.0515(14) -0.0129(10) 0.0003(10) -0.0016(9) O2 0.0242(11) 0.0271(11) 0.0499(14) 0.0060(10) -0.0080(9) -0.0031(9) O3 0.0328(14) 0.099(2) 0.0534(16) -0.0084(15) -0.0086(12) -0.0066(13) O4 0.0548(18) 0.141(3) 0.0617(19) 0.040(2) 0.0059(15) 0.0052(18) O5 0.0317(13) 0.0614(16) 0.0547(15) 0.0042(12) 0.0010(11) -0.0045(11) N1 0.0335(15) 0.0362(16) 0.068(2) 0.0122(14) -0.0001(14) 0.0062(12) N2 0.0306(14) 0.0328(16) 0.0585(18) 0.0074(13) -0.0067(13) 0.0053(12) N3 0.0322(15) 0.0303(15) 0.0533(18) 0.0048(12) -0.0076(12) 0.0064(11) N4 0.0250(13) 0.0261(13) 0.0325(14) 0.0025(10) -0.0036(10) 0.0023(10) N5 0.0414(17) 0.0285(15) 0.0599(19) 0.0042(13) 0.0020(14) 0.0042(12) N6 0.0446(17) 0.0417(17) 0.0493(18) -0.0033(13) 0.0007(13) 0.0111(13) N7 0.0461(17) 0.0451(18) 0.0472(18) -0.0040(14) 0.0012(14) 0.0155(14) N8 0.052(2) 0.057(2) 0.078(3) -0.0091(18) 0.0093(18) 0.0115(16) N9 0.0331(16) 0.0402(16) 0.0423(17) -0.0056(13) -0.0005(13) 0.0045(12) C1 0.0281(17) 0.046(2) 0.055(2) 0.0085(16) 0.0003(15) 0.0063(15) C2 0.0305(18) 0.039(2) 0.060(2) 0.0127(17) 0.0038(16) -0.0031(15) C3 0.0393(19) 0.0302(18) 0.049(2) 0.0109(15) 0.0013(15) -0.0001(14) C4 0.0324(16) 0.0296(16) 0.0317(16) 0.0049(13) -0.0011(13) 0.0025(13) C5 0.0307(17) 0.0316(18) 0.055(2) 0.0094(15) 0.0002(15) -0.0007(14) C6 0.0319(17) 0.0300(17) 0.0378(18) 0.0083(13) -0.0011(13) 0.0039(13) C7 0.035(2) 0.042(2) 0.168(5) 0.015(3) -0.012(3) -0.0012(18) C8 0.0337(18) 0.038(2) 0.072(3) 0.0132(18) -0.0007(17) 0.0043(15) C9 0.0310(16) 0.0309(17) 0.0312(17) -0.0031(13) -0.0040(13) 0.0053(13) C10 0.0299(16) 0.0222(15) 0.0337(16) 0.0000(12) -0.0036(13) 0.0017(12) C11 0.0427(19) 0.0302(17) 0.0354(18) 0.0074(14) -0.0014(14) 0.0001(14) C12 0.0354(18) 0.0403(19) 0.0407(19) 0.0060(15) 0.0088(15) -0.0013(14) C13 0.0242(15) 0.0311(17) 0.0452(19) 0.0013(14) -0.0002(14) 0.0017(13) C14 0.0269(16) 0.0273(16) 0.0336(17) 0.0009(13) 0.0009(12) 0.0013(12) C15 0.0362(19) 0.042(2) 0.056(2) 0.0033(17) 0.0044(16) 0.0026(15) C16 0.0367(19) 0.039(2) 0.071(3) -0.0024(18) 0.0037(17) -0.0051(15) C17 0.047(2) 0.0291(18) 0.057(2) 0.0002(15) 0.0014(17) 0.0012(15) C18 0.0378(18) 0.0301(17) 0.0340(18) 0.0054(13) 0.0009(14) 0.0025(13) C19 0.0357(18) 0.0303(18) 0.048(2) 0.0068(14) 0.0004(15) -0.0011(14) C20 0.0408(19) 0.0378(19) 0.0382(19) 0.0014(15) 0.0000(14) 0.0042(15) C21 0.037(2) 0.049(2) 0.130(4) 0.008(3) -0.003(2) 0.0045(18) C22 0.056(2) 0.053(2) 0.063(3) 0.0039(19) 0.003(2) 0.0079(19) C23 0.046(2) 0.0378(19) 0.0358(18) -0.0101(15) -0.0048(15) 0.0076(15) C24 0.049(2) 0.0304(18) 0.040(2) -0.0073(14) -0.0060(16) 0.0088(15) C25 0.062(3) 0.044(2) 0.054(2) 0.0023(17) -0.0028(19) 0.0155(18) C26 0.069(3) 0.054(3) 0.075(3) 0.001(2) -0.020(2) 0.023(2) C27 0.045(2) 0.053(3) 0.103(4) -0.014(2) -0.005(2) 0.0127(19) C28 0.054(2) 0.044(2) 0.049(2) -0.0060(17) -0.0022(18) 0.0125(17) _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 2.079(2) . ? Zn1 O1 2.079(2) 3_667 ? Zn1 O2 2.081(2) . ? Zn1 O2 2.081(2) 3_667 ? Zn1 N4 2.201(2) . ? Zn1 N4 2.201(2) 3_667 ? O1 H1A 0.830(17) . ? O1 H1B 0.832(17) . ? O2 H2A 0.843(17) . ? O2 H2B 0.830(17) . ? O3 N9 1.244(3) . ? O4 N9 1.220(4) . ? O5 N9 1.244(3) . ? N1 C1 1.325(4) . ? N1 C5 1.334(4) . ? N2 C6 1.271(4) . ? N2 N3 1.409(3) . ? N3 C9 1.281(4) . ? N4 C14 1.338(4) . ? N4 C13 1.345(4) . ? N5 C15 1.325(4) . ? N5 C19 1.338(4) . ? N6 C20 1.281(4) . ? N6 N7 1.398(4) . ? N7 C23 1.289(4) . ? N8 C28 1.326(5) . ? N8 C27 1.336(6) . ? C1 C2 1.371(5) . ? C1 H1 0.9300 . ? C2 C3 1.371(4) . ? C2 H2 0.9300 . ? C3 C4 1.387(4) . ? C3 H3 0.9300 . ? C4 C5 1.385(4) . ? C4 C6 1.485(4) . ? C5 H5 0.9300 . ? C6 C7 1.492(5) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.489(4) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.491(4) . ? C10 C14 1.391(4) . ? C10 C11 1.392(4) . ? C11 C12 1.375(4) . ? C11 H11 0.9300 . ? C12 C13 1.379(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.371(5) . ? C15 H15 0.9300 . ? C16 C17 1.372(5) . ? C16 H16 0.9300 . ? C17 C18 1.387(5) . ? C17 H17 0.9300 . ? C18 C19 1.384(4) . ? C18 C20 1.475(4) . ? C19 H19 0.9300 . ? C20 C21 1.497(5) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.493(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.476(5) . ? C24 C25 1.381(5) . ? C24 C28 1.390(5) . ? C25 C26 1.374(6) . ? C25 H25 0.9300 . ? C26 C27 1.365(6) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? 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 180.00(11) . 3_667 ? O1 Zn1 O2 90.58(8) . . ? O1 Zn1 O2 89.42(8) 3_667 . ? O1 Zn1 O2 89.42(8) . 3_667 ? O1 Zn1 O2 90.58(8) 3_667 3_667 ? O2 Zn1 O2 180.00(10) . 3_667 ? O1 Zn1 N4 89.48(9) . . ? O1 Zn1 N4 90.52(9) 3_667 . ? O2 Zn1 N4 92.67(9) . . ? O2 Zn1 N4 87.33(9) 3_667 . ? O1 Zn1 N4 90.52(9) . 3_667 ? O1 Zn1 N4 89.48(9) 3_667 3_667 ? O2 Zn1 N4 87.33(9) . 3_667 ? O2 Zn1 N4 92.67(9) 3_667 3_667 ? N4 Zn1 N4 180.000(1) . 3_667 ? Zn1 O1 H1A 117(2) . . ? Zn1 O1 H1B 117(2) . . ? H1A O1 H1B 113(2) . . ? Zn1 O2 H2A 118(2) . . ? Zn1 O2 H2B 114(2) . . ? H2A O2 H2B 112(2) . . ? C1 N1 C5 117.1(3) . . ? C6 N2 N3 115.6(3) . . ? C9 N3 N2 112.6(3) . . ? C14 N4 C13 117.6(2) . . ? C14 N4 Zn1 121.75(19) . . ? C13 N4 Zn1 120.57(19) . . ? C15 N5 C19 117.1(3) . . ? C20 N6 N7 115.4(3) . . ? C23 N7 N6 114.6(3) . . ? C28 N8 C27 115.6(4) . . ? O4 N9 O3 119.7(3) . . ? O4 N9 O5 121.1(3) . . ? O3 N9 O5 119.2(3) . . ? N1 C1 C2 123.5(3) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C1 C2 C3 118.8(3) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C2 C3 C4 119.6(3) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 116.8(3) . . ? C5 C4 C6 121.9(3) . . ? C3 C4 C6 121.2(3) . . ? N1 C5 C4 124.2(3) . . ? N1 C5 H5 117.9 . . ? C4 C5 H5 117.9 . . ? N2 C6 C4 116.0(3) . . ? N2 C6 C7 124.8(3) . . ? C4 C6 C7 119.1(3) . . ? 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 . . ? C9 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C9 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C9 C8 125.7(3) . . ? N3 C9 C10 116.1(3) . . ? C8 C9 C10 118.1(3) . . ? C14 C10 C11 117.4(3) . . ? C14 C10 C9 120.7(3) . . ? C11 C10 C9 121.9(3) . . ? C12 C11 C10 119.4(3) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 119.2(3) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? N4 C13 C12 122.7(3) . . ? N4 C13 H13 118.7 . . ? C12 C13 H13 118.7 . . ? N4 C14 C10 123.7(3) . . ? N4 C14 H14 118.1 . . ? C10 C14 H14 118.1 . . ? N5 C15 C16 123.3(3) . . ? N5 C15 H15 118.4 . . ? C16 C15 H15 118.4 . . ? C15 C16 C17 119.0(3) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C16 C17 C18 119.7(3) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C19 C18 C17 116.6(3) . . ? C19 C18 C20 121.3(3) . . ? C17 C18 C20 122.1(3) . . ? N5 C19 C18 124.5(3) . . ? N5 C19 H19 117.8 . . ? C18 C19 H19 117.8 . . ? N6 C20 C18 116.5(3) . . ? N6 C20 C21 123.6(3) . . ? C18 C20 C21 119.9(3) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C23 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N7 C23 C24 115.6(3) . . ? N7 C23 C22 124.5(3) . . ? C24 C23 C22 119.9(3) . . ? C25 C24 C28 117.0(3) . . ? C25 C24 C23 121.0(3) . . ? C28 C24 C23 122.0(3) . . ? C26 C25 C24 118.9(4) . . ? C26 C25 H25 120.5 . . ? C24 C25 H25 120.5 . . ? C27 C26 C25 119.1(4) . . ? C27 C26 H26 120.4 . . ? C25 C26 H26 120.4 . . ? N8 C27 C26 124.1(4) . . ? N8 C27 H27 117.9 . . ? C26 C27 H27 117.9 . . ? N8 C28 C24 125.2(4) . . ? N8 C28 H28 117.4 . . ? C24 C28 H28 117.4 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A N1 0.830(17) 2.01(2) 2.794(3) 158(4) 4_676 O1 H1B O3 0.832(17) 1.92(2) 2.733(3) 164(3) 3_667 O1 H1B N9 0.832(17) 2.570(18) 3.387(3) 168(3) 3_667 O1 H1B O4 0.832(17) 2.56(3) 3.245(4) 140(3) 3_667 O2 H2A O5 0.843(17) 1.94(2) 2.770(3) 169(3) 1_455 O2 H2A N9 0.843(17) 2.63(2) 3.393(3) 152(3) 1_455 O2 H2A O4 0.843(17) 2.67(3) 3.229(4) 125(3) 1_455 O2 H2B N5 0.830(17) 1.99(2) 2.799(3) 166(3) 1_556 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.473 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.058 # Attachment 'a312.cif' data_a312 _database_code_depnum_ccdc_archive 'CCDC 723324' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 N14 Zn' _chemical_formula_weight 626.03 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' 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 12.618(4) _cell_length_b 13.076(4) _cell_length_c 8.739(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.414(4) _cell_angle_gamma 90.00 _cell_volume 1383.2(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3237 _cell_measurement_theta_min 3.37 _cell_measurement_theta_max 25.30 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.936 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8496 _exptl_absorpt_correction_T_max 0.9122 _exptl_absorpt_process_details 'SADABS (Bruker, 1998)' _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 'Bruker smart 1000' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10473 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 26.69 _reflns_number_total 2701 _reflns_number_gt 2121 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (2005)' _computing_publication_material 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^)+(0.0362P)^2^+0.2842P] 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_number_reflns 2701 _refine_ls_number_parameters 198 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0735 _refine_ls_wR_factor_gt 0.0697 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 0.0000 0.5000 0.0000 0.01290(11) Uani 1 2 d S . . C1 C 0.24521(16) 0.41067(15) 0.0726(2) 0.0147(4) Uani 1 1 d . . . H1 H 0.2326 0.4261 -0.0373 0.018 Uiso 1 1 calc R . . C2 C 0.34833(16) 0.37437(15) 0.1559(2) 0.0128(4) Uani 1 1 d . . . C3 C 0.36528(17) 0.34903(16) 0.3163(2) 0.0165(5) Uani 1 1 d . . . H3 H 0.4347 0.3234 0.3779 0.020 Uiso 1 1 calc R . . C4 C 0.27938(17) 0.36176(16) 0.3845(2) 0.0181(5) Uani 1 1 d . . . H4 H 0.2888 0.3441 0.4930 0.022 Uiso 1 1 calc R . . C5 C 0.17975(17) 0.40053(16) 0.2924(2) 0.0162(5) Uani 1 1 d . . . H5 H 0.1218 0.4098 0.3407 0.019 Uiso 1 1 calc R . . C6 C 0.43808(17) 0.36465(15) 0.0764(2) 0.0149(4) Uani 1 1 d . . . C7 C 0.41754(17) 0.40528(17) -0.0908(2) 0.0181(5) Uani 1 1 d . . . H7A H 0.4858 0.4010 -0.1229 0.027 Uiso 1 1 calc R . . H7B H 0.3936 0.4767 -0.0943 0.027 Uiso 1 1 calc R . . H7C H 0.3599 0.3645 -0.1640 0.027 Uiso 1 1 calc R . . C8 C 0.95736(17) 0.26782(16) -0.0586(2) 0.0162(4) Uani 1 1 d . . . H8 H 1.0218 0.2749 -0.0935 0.019 Uiso 1 1 calc R . . C9 C 0.90960(16) 0.17282(16) -0.0656(2) 0.0166(5) Uani 1 1 d . . . H9 H 0.9413 0.1157 -0.1035 0.020 Uiso 1 1 calc R . . C10 C 0.81449(17) 0.16108(16) -0.0167(2) 0.0162(4) Uani 1 1 d . . . H10 H 0.7805 0.0960 -0.0204 0.019 Uiso 1 1 calc R . . C11 C 0.77002(16) 0.24663(15) 0.0379(2) 0.0138(4) Uani 1 1 d . . . C12 C 0.82515(16) 0.33908(16) 0.0434(2) 0.0144(4) Uani 1 1 d . . . H12 H 0.7964 0.3972 0.0834 0.017 Uiso 1 1 calc R . . C13 C 0.66877(16) 0.24017(16) 0.0930(2) 0.0146(4) Uani 1 1 d . . . C14 C 0.63641(19) 0.13861(16) 0.1441(3) 0.0223(5) Uani 1 1 d . . . H14A H 0.5838 0.1486 0.2065 0.034 Uiso 1 1 calc R . . H14B H 0.7022 0.1035 0.2096 0.034 Uiso 1 1 calc R . . H14C H 0.6020 0.0972 0.0497 0.034 Uiso 1 1 calc R . . N1 N 0.16101(13) 0.42566(13) 0.13788(19) 0.0142(4) Uani 1 1 d . . . N2 N 0.52761(14) 0.32202(13) 0.1588(2) 0.0164(4) Uani 1 1 d . . . N3 N 0.61627(14) 0.32431(14) 0.0914(2) 0.0169(4) Uani 1 1 d . . . N4 N 0.91663(13) 0.35143(13) -0.00441(19) 0.0142(4) Uani 1 1 d . . . N5 N -0.02545(14) 0.53468(14) 0.22238(19) 0.0170(4) Uani 1 1 d . . . N6 N -0.08927(14) 0.57465(14) 0.28025(19) 0.0184(4) Uani 1 1 d . . . N7 N -0.14983(17) 0.6133(2) 0.3417(2) 0.0438(6) 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 0.01020(18) 0.01538(19) 0.01428(17) -0.00029(15) 0.00533(12) 0.00027(15) C1 0.0132(11) 0.0148(11) 0.0167(10) -0.0014(8) 0.0052(8) -0.0004(9) C2 0.0114(11) 0.0112(11) 0.0164(10) -0.0022(8) 0.0049(8) -0.0009(8) C3 0.0124(11) 0.0166(12) 0.0195(11) 0.0025(9) 0.0028(9) 0.0029(9) C4 0.0185(12) 0.0194(12) 0.0174(10) 0.0028(9) 0.0066(9) 0.0011(9) C5 0.0132(11) 0.0178(12) 0.0203(11) -0.0002(9) 0.0090(9) -0.0006(9) C6 0.0136(11) 0.0137(11) 0.0183(10) -0.0021(8) 0.0063(9) -0.0010(9) C7 0.0138(11) 0.0237(13) 0.0183(11) 0.0000(9) 0.0071(9) 0.0003(9) C8 0.0115(10) 0.0236(12) 0.0149(9) 0.0006(9) 0.0059(8) 0.0025(9) C9 0.0151(11) 0.0186(12) 0.0164(10) -0.0027(9) 0.0048(8) 0.0026(9) C10 0.0145(11) 0.0158(11) 0.0177(10) 0.0000(8) 0.0035(8) -0.0010(9) C11 0.0104(10) 0.0168(11) 0.0135(9) 0.0018(8) 0.0022(8) 0.0025(9) C12 0.0129(11) 0.0157(11) 0.0150(10) 0.0003(8) 0.0044(8) 0.0028(9) C13 0.0111(10) 0.0200(12) 0.0123(9) 0.0014(8) 0.0024(8) -0.0006(9) C14 0.0190(12) 0.0200(12) 0.0317(12) 0.0032(10) 0.0131(10) 0.0026(10) N1 0.0115(9) 0.0148(9) 0.0173(9) -0.0010(7) 0.0057(7) 0.0001(7) N2 0.0115(9) 0.0196(10) 0.0203(9) 0.0008(7) 0.0080(7) 0.0013(8) N3 0.0103(9) 0.0210(10) 0.0218(9) 0.0014(7) 0.0084(7) 0.0014(8) N4 0.0088(9) 0.0186(10) 0.0155(8) 0.0006(7) 0.0038(7) 0.0010(7) N5 0.0160(10) 0.0200(10) 0.0167(9) -0.0003(7) 0.0074(8) 0.0053(8) N6 0.0141(10) 0.0265(11) 0.0130(8) -0.0024(8) 0.0011(7) -0.0018(8) N7 0.0210(12) 0.0868(19) 0.0222(11) -0.0187(11) 0.0040(9) 0.0152(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 Zn1 N5 2.1067(17) 3_565 ? Zn1 N5 2.1067(17) . ? Zn1 N4 2.2045(17) 1_455 ? Zn1 N4 2.2045(17) 3_665 ? Zn1 N1 2.2674(17) . ? Zn1 N1 2.2674(17) 3_565 ? C1 N1 1.354(2) . ? C1 C2 1.383(3) . ? C1 H1 0.9500 . ? C2 C3 1.397(3) . ? C2 C6 1.492(3) . ? C3 C4 1.386(3) . ? C3 H3 0.9500 . ? C4 C5 1.383(3) . ? C4 H4 0.9500 . ? C5 N1 1.345(2) . ? C5 H5 0.9500 . ? C6 N2 1.283(3) . ? C6 C7 1.508(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 N4 1.350(3) . ? C8 C9 1.374(3) . ? C8 H8 0.9500 . ? C9 C10 1.392(3) . ? C9 H9 0.9500 . ? C10 C11 1.395(3) . ? C10 H10 0.9500 . ? C11 C12 1.389(3) . ? C11 C13 1.490(3) . ? C12 N4 1.344(2) . ? C12 H12 0.9500 . ? C13 N3 1.282(3) . ? C13 C14 1.494(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? N2 N3 1.404(2) . ? N4 Zn1 2.2045(17) 1_655 ? N5 N6 1.187(2) . ? N6 N7 1.166(2) . ? 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 N5 Zn1 N5 180.0 3_565 . ? N5 Zn1 N4 89.46(6) 3_565 1_455 ? N5 Zn1 N4 90.54(6) . 1_455 ? N5 Zn1 N4 90.54(6) 3_565 3_665 ? N5 Zn1 N4 89.46(6) . 3_665 ? N4 Zn1 N4 180.00(8) 1_455 3_665 ? N5 Zn1 N1 92.91(6) 3_565 . ? N5 Zn1 N1 87.09(6) . . ? N4 Zn1 N1 89.02(6) 1_455 . ? N4 Zn1 N1 90.98(6) 3_665 . ? N5 Zn1 N1 87.09(6) 3_565 3_565 ? N5 Zn1 N1 92.91(6) . 3_565 ? N4 Zn1 N1 90.98(6) 1_455 3_565 ? N4 Zn1 N1 89.02(6) 3_665 3_565 ? N1 Zn1 N1 180.0 . 3_565 ? N1 C1 C2 124.15(18) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C1 C2 C3 117.64(18) . . ? C1 C2 C6 120.61(17) . . ? C3 C2 C6 121.74(18) . . ? C4 C3 C2 119.09(19) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C5 C4 C3 119.11(19) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? N1 C5 C4 123.15(18) . . ? N1 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? N2 C6 C2 116.09(17) . . ? N2 C6 C7 125.45(17) . . ? C2 C6 C7 118.45(17) . . ? 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 . . ? N4 C8 C9 122.82(18) . . ? N4 C8 H8 118.6 . . ? C9 C8 H8 118.6 . . ? C8 C9 C10 119.44(19) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C9 C10 C11 118.80(19) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C12 C11 C10 117.64(18) . . ? C12 C11 C13 120.34(18) . . ? C10 C11 C13 121.99(18) . . ? N4 C12 C11 124.04(18) . . ? N4 C12 H12 118.0 . . ? C11 C12 H12 118.0 . . ? N3 C13 C11 115.79(18) . . ? N3 C13 C14 125.60(18) . . ? C11 C13 C14 118.60(18) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C5 N1 C1 116.83(17) . . ? C5 N1 Zn1 121.03(13) . . ? C1 N1 Zn1 122.00(13) . . ? C6 N2 N3 115.79(16) . . ? C13 N3 N2 116.56(17) . . ? C12 N4 C8 117.23(17) . . ? C12 N4 Zn1 123.24(13) . 1_655 ? C8 N4 Zn1 119.53(13) . 1_655 ? N6 N5 Zn1 141.89(14) . . ? N7 N6 N5 177.9(2) . . ? _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.340 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.058 # Attachment '3a8kh.cif' data_3a8kh _database_code_depnum_ccdc_archive 'CCDC 724229' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H28 N10 S2 Zn' _chemical_formula_weight 658.15 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' S S 0.1246 0.1234 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5576(5) _cell_length_b 16.9548(10) _cell_length_c 9.6533(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.630(3) _cell_angle_gamma 90.00 _cell_volume 1546.58(15) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 11498 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 27.45 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.968 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8226 _exptl_absorpt_correction_T_max 0.8451 _exptl_absorpt_process_details 'SADABS (Bruker, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 39569 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 27.58 _reflns_number_total 3576 _reflns_number_gt 2952 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (2005)' _computing_publication_material 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^)+(0.0607P)^2^+10.2843P] 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_number_reflns 3576 _refine_ls_number_parameters 198 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0632 _refine_ls_wR_factor_ref 0.2069 _refine_ls_wR_factor_gt 0.2025 _refine_ls_goodness_of_fit_ref 1.195 _refine_ls_restrained_S_all 1.195 _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 0.0000 0.0000 0.0000 0.0215(2) Uani 1 2 d S . . C1 C -0.2280(6) 0.0819(3) 0.1520(6) 0.0275(11) Uani 1 1 d . . . H1 H -0.1663 0.0651 0.2302 0.033 Uiso 1 1 calc R . . C2 C -0.3526(6) 0.1210(3) 0.1724(6) 0.0308(12) Uani 1 1 d . . . H2 H -0.3732 0.1312 0.2618 0.037 Uiso 1 1 calc R . . C3 C -0.4448(6) 0.1441(3) 0.0523(6) 0.0309(12) Uani 1 1 d . . . H3 H -0.5291 0.1693 0.0623 0.037 Uiso 1 1 calc R . . C4 C -0.4136(6) 0.1304(3) -0.0778(6) 0.0255(11) Uani 1 1 d . . . C5 C -0.2848(5) 0.0920(3) -0.0864(5) 0.0252(10) Uani 1 1 d . . . H5 H -0.2613 0.0830 -0.1751 0.030 Uiso 1 1 calc R . . C6 C -0.5079(5) 0.1532(3) -0.2093(5) 0.0245(10) Uani 1 1 d . . . C7 C -0.6329(7) 0.2058(4) -0.2031(6) 0.0398(15) Uani 1 1 d . . . H7A H -0.6530 0.2352 -0.2887 0.060 Uiso 1 1 calc R . . H7B H -0.6120 0.2416 -0.1257 0.060 Uiso 1 1 calc R . . H7C H -0.7136 0.1743 -0.1910 0.060 Uiso 1 1 calc R . . C8 C -0.8616(5) 0.1647(3) -0.9117(5) 0.0258(11) Uani 1 1 d . . . H8 H -0.9112 0.1787 -0.9985 0.031 Uiso 1 1 calc R . . C9 C -0.7770(6) 0.2210(3) -0.8363(6) 0.0268(11) Uani 1 1 d . . . H9 H -0.7707 0.2715 -0.8725 0.032 Uiso 1 1 calc R . . C10 C -0.7020(5) 0.2018(3) -0.7070(5) 0.0221(10) Uani 1 1 d . . . H10 H -0.6431 0.2386 -0.6559 0.027 Uiso 1 1 calc R . . C11 C -0.7167(5) 0.1252(3) -0.6542(5) 0.0214(10) Uani 1 1 d . . . C12 C -0.8063(5) 0.0735(3) -0.7368(5) 0.0250(10) Uani 1 1 d . . . H12 H -0.8192 0.0236 -0.7007 0.030 Uiso 1 1 calc R . . C13 C -0.6423(5) 0.0993(3) -0.5148(5) 0.0224(10) Uani 1 1 d . . . C14 C -0.6719(6) 0.0183(3) -0.4618(6) 0.0279(11) Uani 1 1 d . . . H14A H -0.6135 0.0093 -0.3733 0.042 Uiso 1 1 calc R . . H14B H -0.6512 -0.0207 -0.5280 0.042 Uiso 1 1 calc R . . H14C H -0.7697 0.0147 -0.4504 0.042 Uiso 1 1 calc R . . C15 C 0.0096(5) 0.0954(3) -0.2907(5) 0.0241(10) Uani 1 1 d . . . N1 N -0.1940(5) 0.0676(3) 0.0237(4) 0.0242(9) Uani 1 1 d . . . N2 N -0.4762(4) 0.1239(3) -0.3237(4) 0.0243(9) Uani 1 1 d . . . N3 N -0.5549(5) 0.1491(3) -0.4488(4) 0.0243(9) Uani 1 1 d . . . N4 N -0.8755(4) 0.0904(3) -0.8650(4) 0.0237(9) Uani 1 1 d . . . N5 N 0.0215(5) 0.0666(3) -0.1794(4) 0.0254(9) Uani 1 1 d . . . S1 S -0.00744(17) 0.13491(9) -0.44559(15) 0.0359(4) 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 0.0207(4) 0.0242(4) 0.0186(4) 0.0031(3) 0.0002(3) -0.0006(3) C1 0.026(3) 0.031(3) 0.025(2) 0.003(2) 0.001(2) -0.002(2) C2 0.040(3) 0.031(3) 0.021(2) -0.001(2) 0.005(2) 0.001(2) C3 0.031(3) 0.024(3) 0.036(3) 0.002(2) 0.000(2) 0.006(2) C4 0.027(3) 0.016(2) 0.031(3) 0.0005(19) -0.004(2) -0.0011(19) C5 0.023(2) 0.027(3) 0.024(2) -0.003(2) -0.0007(19) 0.001(2) C6 0.023(2) 0.022(2) 0.026(2) -0.004(2) -0.0025(19) 0.000(2) C7 0.036(3) 0.047(4) 0.033(3) -0.010(3) -0.006(2) 0.019(3) C8 0.024(2) 0.029(3) 0.023(2) 0.003(2) 0.0001(19) 0.004(2) C9 0.028(3) 0.021(2) 0.031(3) 0.005(2) 0.004(2) 0.003(2) C10 0.021(2) 0.021(2) 0.025(2) -0.0024(19) 0.0045(18) 0.0007(19) C11 0.019(2) 0.023(2) 0.023(2) -0.0005(19) 0.0024(18) 0.0014(18) C12 0.025(2) 0.022(2) 0.026(2) 0.003(2) 0.000(2) 0.001(2) C13 0.022(2) 0.025(2) 0.020(2) -0.0013(19) 0.0022(18) 0.0001(19) C14 0.028(3) 0.027(3) 0.027(3) 0.002(2) -0.003(2) 0.000(2) C15 0.019(2) 0.022(2) 0.031(3) -0.005(2) 0.0030(19) 0.0017(19) N1 0.024(2) 0.025(2) 0.023(2) 0.0004(17) 0.0017(16) -0.0014(17) N2 0.021(2) 0.028(2) 0.023(2) 0.0027(17) -0.0011(16) -0.0010(17) N3 0.024(2) 0.024(2) 0.023(2) -0.0011(17) -0.0013(17) 0.0027(17) N4 0.022(2) 0.024(2) 0.024(2) 0.0006(17) -0.0003(16) -0.0005(17) N5 0.026(2) 0.027(2) 0.022(2) 0.0015(17) 0.0012(17) -0.0010(18) S1 0.0416(8) 0.0392(8) 0.0275(7) 0.0116(6) 0.0074(6) 0.0095(6) _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 N5 2.103(4) 3 ? Zn1 N5 2.103(4) . ? Zn1 N1 2.220(4) 3 ? Zn1 N1 2.220(4) . ? Zn1 N4 2.236(4) 1_656 ? Zn1 N4 2.236(4) 3_454 ? C1 N1 1.349(7) . ? C1 C2 1.402(8) . ? C1 H1 0.9300 . ? C2 C3 1.403(7) . ? C2 H2 0.9300 . ? C3 C4 1.354(8) . ? C3 H3 0.9300 . ? C4 C5 1.406(7) . ? C4 C6 1.493(7) . ? C5 N1 1.333(6) . ? C5 H5 0.9300 . ? C6 N2 1.289(7) . ? C6 C7 1.499(7) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N4 1.350(7) . ? C8 C9 1.386(7) . ? C8 H8 0.9300 . ? C9 C10 1.382(7) . ? C9 H9 0.9300 . ? C10 C11 1.411(7) . ? C10 H10 0.9300 . ? C11 C12 1.389(7) . ? C11 C13 1.490(7) . ? C12 N4 1.344(6) . ? C12 H12 0.9300 . ? C13 N3 1.288(6) . ? C13 C14 1.506(7) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 N5 1.170(7) . ? C15 S1 1.624(6) . ? N2 N3 1.390(6) . ? N4 Zn1 2.236(4) 1_454 ? 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 N5 Zn1 N5 180.0(2) 3 . ? N5 Zn1 N1 89.63(16) 3 3 ? N5 Zn1 N1 90.37(16) . 3 ? N5 Zn1 N1 90.37(16) 3 . ? N5 Zn1 N1 89.63(16) . . ? N1 Zn1 N1 180.0(2) 3 . ? N5 Zn1 N4 89.88(16) 3 1_656 ? N5 Zn1 N4 90.12(16) . 1_656 ? N1 Zn1 N4 91.96(16) 3 1_656 ? N1 Zn1 N4 88.04(16) . 1_656 ? N5 Zn1 N4 90.12(16) 3 3_454 ? N5 Zn1 N4 89.88(16) . 3_454 ? N1 Zn1 N4 88.04(16) 3 3_454 ? N1 Zn1 N4 91.96(16) . 3_454 ? N4 Zn1 N4 180.0(3) 1_656 3_454 ? N1 C1 C2 122.7(5) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 117.3(5) . . ? C1 C2 H2 121.4 . . ? C3 C2 H2 121.4 . . ? C4 C3 C2 121.3(5) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 116.8(5) . . ? C3 C4 C6 123.7(5) . . ? C5 C4 C6 119.5(5) . . ? N1 C5 C4 124.6(5) . . ? N1 C5 H5 117.7 . . ? C4 C5 H5 117.7 . . ? N2 C6 C4 116.1(5) . . ? N2 C6 C7 123.7(5) . . ? C4 C6 C7 120.2(5) . . ? 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 . . ? N4 C8 C9 123.1(5) . . ? N4 C8 H8 118.4 . . ? C9 C8 H8 118.4 . . ? C10 C9 C8 119.6(5) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 118.5(5) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? C12 C11 C10 117.4(4) . . ? C12 C11 C13 120.1(5) . . ? C10 C11 C13 122.5(4) . . ? N4 C12 C11 124.7(5) . . ? N4 C12 H12 117.6 . . ? C11 C12 H12 117.6 . . ? N3 C13 C11 116.1(5) . . ? N3 C13 C14 124.8(5) . . ? C11 C13 C14 119.1(4) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N5 C15 S1 179.7(5) . . ? C5 N1 C1 117.3(5) . . ? C5 N1 Zn1 122.1(4) . . ? C1 N1 Zn1 120.5(3) . . ? C6 N2 N3 117.4(4) . . ? C13 N3 N2 117.0(4) . . ? C12 N4 C8 116.5(4) . . ? C12 N4 Zn1 122.4(3) . 1_454 ? C8 N4 Zn1 121.0(3) . 1_454 ? C15 N5 Zn1 166.4(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.882 _refine_diff_density_min -0.694 _refine_diff_density_rms 0.128