# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H22 N6 O6 Zn' _chemical_formula_weight 471.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5231(10) _cell_length_b 10.2095(11) _cell_length_c 11.7475(13) _cell_angle_alpha 105.6250(10) _cell_angle_beta 91.6650(10) _cell_angle_gamma 106.8790(10) _cell_volume 1045.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3415 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 25.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 1.221 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7500 _exptl_absorpt_correction_T_max 0.8012 _exptl_absorpt_process_details SADABS _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 7851 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3863 _reflns_number_gt 3350 _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^)+(0.0356P)^2^+0.3975P] 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 3863 _refine_ls_number_parameters 282 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.0369 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0770 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.087 _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 O6 O 0.9538(13) 0.3454(9) 0.4055(10) 0.136(5) Uani 0.504(12) 1 d P A 1 H4W H 0.8634 0.3229 0.3789 0.204 Uiso 0.504(12) 1 d PR A 1 H3W H 1.0056 0.3148 0.3532 0.204 Uiso 0.504(12) 1 d PR A 1 O6' O 1.1067(16) 0.4033(11) 0.4657(6) 0.148(5) Uani 0.496(12) 1 d P A 2 H5W H 1.1507 0.4319 0.4108 0.221 Uiso 0.496(12) 1 d PR A 2 H6W H 1.0143 0.3681 0.4438 0.221 Uiso 0.496(12) 1 d PR A 2 Zn1 Zn 0.15459(3) 0.66234(3) 0.19090(2) 0.03450(10) Uani 1 1 d . . . O1 O 0.1958(2) 0.49084(16) 0.08988(14) 0.0437(4) Uani 1 1 d . . . O2 O 0.1373(3) 0.4112(2) 0.24325(17) 0.0673(6) Uani 1 1 d . . . O3 O 0.1226(2) -0.07896(17) 0.23767(15) 0.0460(4) Uani 1 1 d . . . O4 O 0.18818(19) -0.21571(15) 0.08201(14) 0.0399(4) Uani 1 1 d . . . O5 O 0.0314(3) 0.0919(3) 0.4318(2) 0.0916(8) Uani 1 1 d . . . H1W H 0.0265 0.1736 0.4312 0.137 Uiso 1 1 d R . . H2W H 0.0480 0.0455 0.3646 0.137 Uiso 1 1 d R . . N1 N 0.2927(2) 0.7465(2) 0.34379(17) 0.0377(5) Uani 1 1 d . . . N2 N 0.4577(2) 0.7737(2) 0.48679(18) 0.0420(5) Uani 1 1 d . . . N3 N 0.3817(3) 0.8657(3) 0.5332(2) 0.0606(7) Uani 1 1 d . . . N4 N -0.0600(2) 0.6004(2) 0.21775(17) 0.0370(4) Uani 1 1 d . . . N5 N -0.2859(2) 0.4647(2) 0.19838(17) 0.0391(5) Uani 1 1 d . . . N6 N -0.2817(3) 0.5905(2) 0.2792(2) 0.0517(6) Uani 1 1 d . . . C1 C 0.1908(2) 0.2519(2) 0.07622(19) 0.0292(5) Uani 1 1 d . . . C2 C 0.1603(2) 0.1421(2) 0.12872(19) 0.0293(5) Uani 1 1 d . . . H2 H 0.1221 0.1543 0.2014 0.035 Uiso 1 1 calc R . . C3 C 0.1861(2) 0.0143(2) 0.07424(19) 0.0301(5) Uani 1 1 d . . . C4 C 0.2419(3) -0.0023(2) -0.0347(2) 0.0417(6) Uani 1 1 d U . . H4 H 0.2592 -0.0880 -0.0720 0.050 Uiso 1 1 calc R . . C5 C 0.2726(3) 0.1058(3) -0.0893(2) 0.0479(6) Uani 1 1 d U . . C6 C 0.2461(3) 0.2328(2) -0.0326(2) 0.0383(5) Uani 1 1 d U . . H6 H 0.2657 0.3062 -0.0682 0.046 Uiso 1 1 calc R . . C7 C 0.1717(3) 0.3926(2) 0.1417(2) 0.0359(5) Uani 1 1 d . . . C8 C 0.1623(3) -0.1000(2) 0.1360(2) 0.0331(5) Uani 1 1 d . . . C9 C 0.3366(5) 0.0870(4) -0.2073(3) 0.0918(13) Uani 1 1 d U . . H9A H 0.4404 0.1000 -0.1939 0.138 Uiso 1 1 calc R . . H9B H 0.3224 0.1565 -0.2437 0.138 Uiso 1 1 calc R . . H9C H 0.2877 -0.0075 -0.2589 0.138 Uiso 1 1 calc R . . C10 C 0.4041(3) 0.7054(3) 0.3754(2) 0.0417(6) Uani 1 1 d . . . H10 H 0.4394 0.6375 0.3255 0.050 Uiso 1 1 calc R . . C11 C 0.2850(3) 0.8456(3) 0.4439(2) 0.0514(7) Uani 1 1 d . . . H11 H 0.2166 0.8955 0.4489 0.062 Uiso 1 1 calc R . . C12 C 0.5768(3) 0.7578(3) 0.5586(2) 0.0497(7) Uani 1 1 d . . . H12A H 0.6380 0.8518 0.6063 0.060 Uiso 1 1 calc R . . H12B H 0.6382 0.7149 0.5060 0.060 Uiso 1 1 calc R . . C13 C 0.5192(3) 0.6660(3) 0.6404(2) 0.0468(6) Uani 1 1 d . . . H13A H 0.4435 0.5795 0.5946 0.056 Uiso 1 1 calc R . . H13B H 0.5994 0.6379 0.6687 0.056 Uiso 1 1 calc R . . C14 C -0.1440(3) 0.6670(3) 0.2871(2) 0.0481(6) Uani 1 1 d . . . H14 H -0.1065 0.7603 0.3367 0.058 Uiso 1 1 calc R . . C15 C -0.1545(3) 0.4733(2) 0.1634(2) 0.0385(5) Uani 1 1 d . . . H15 H -0.1315 0.4005 0.1082 0.046 Uiso 1 1 calc R . . C16 C -0.4205(3) 0.3427(3) 0.1616(2) 0.0498(6) Uani 1 1 d . . . H16A H -0.4101 0.2782 0.0872 0.060 Uiso 1 1 calc R . . H16B H -0.5028 0.3764 0.1474 0.060 Uiso 1 1 calc R . . C17 C -0.4551(3) 0.2612(3) 0.2528(2) 0.0482(6) Uani 1 1 d . . . H17A H -0.3651 0.2473 0.2806 0.058 Uiso 1 1 calc R . . H17B H -0.5247 0.1674 0.2143 0.058 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 O6 0.149(9) 0.169(7) 0.150(8) 0.097(6) 0.100(8) 0.084(6) O6' 0.224(14) 0.201(9) 0.073(4) 0.071(5) 0.054(6) 0.117(9) Zn1 0.05140(18) 0.02416(15) 0.03347(16) 0.01108(11) 0.01202(12) 0.01682(12) O1 0.0740(12) 0.0262(8) 0.0417(9) 0.0153(7) 0.0173(8) 0.0259(8) O2 0.1345(19) 0.0413(11) 0.0485(12) 0.0209(9) 0.0417(12) 0.0507(12) O3 0.0753(12) 0.0325(9) 0.0398(10) 0.0154(7) 0.0195(9) 0.0254(9) O4 0.0657(11) 0.0216(8) 0.0395(9) 0.0113(7) 0.0135(8) 0.0212(8) O5 0.136(2) 0.0796(16) 0.0751(16) 0.0219(13) 0.0507(16) 0.0535(16) N1 0.0504(12) 0.0312(10) 0.0358(11) 0.0096(8) 0.0103(9) 0.0186(9) N2 0.0452(12) 0.0419(12) 0.0412(12) 0.0105(10) 0.0083(9) 0.0180(10) N3 0.0731(17) 0.0646(16) 0.0457(14) -0.0036(12) 0.0007(12) 0.0424(14) N4 0.0475(12) 0.0292(10) 0.0363(11) 0.0087(8) 0.0087(9) 0.0153(9) N5 0.0444(12) 0.0377(11) 0.0348(11) 0.0080(9) 0.0044(9) 0.0142(9) N6 0.0541(14) 0.0409(12) 0.0590(14) 0.0057(11) 0.0182(11) 0.0203(11) C1 0.0337(12) 0.0225(10) 0.0325(12) 0.0066(9) 0.0020(9) 0.0117(9) C2 0.0368(12) 0.0242(11) 0.0290(11) 0.0086(9) 0.0048(9) 0.0119(9) C3 0.0374(12) 0.0211(10) 0.0315(11) 0.0070(9) -0.0001(9) 0.0098(9) C4 0.0694(17) 0.0259(11) 0.0369(13) 0.0088(10) 0.0148(12) 0.0250(11) C5 0.0799(18) 0.0383(13) 0.0383(13) 0.0159(11) 0.0232(13) 0.0314(13) C6 0.0586(15) 0.0274(11) 0.0373(13) 0.0158(10) 0.0120(11) 0.0195(11) C7 0.0501(14) 0.0262(11) 0.0370(13) 0.0108(10) 0.0077(11) 0.0185(10) C8 0.0442(13) 0.0210(10) 0.0346(13) 0.0080(9) 0.0032(10) 0.0112(9) C9 0.179(4) 0.071(2) 0.068(2) 0.0408(17) 0.073(2) 0.078(2) C10 0.0538(15) 0.0353(13) 0.0417(14) 0.0112(11) 0.0147(12) 0.0217(12) C11 0.0616(17) 0.0522(16) 0.0458(16) 0.0052(13) 0.0073(13) 0.0338(14) C12 0.0367(14) 0.0563(17) 0.0563(17) 0.0141(13) 0.0033(12) 0.0170(12) C13 0.0461(15) 0.0471(15) 0.0486(15) 0.0118(12) 0.0000(12) 0.0189(12) C14 0.0583(17) 0.0322(13) 0.0495(16) 0.0020(11) 0.0146(13) 0.0157(12) C15 0.0495(15) 0.0350(13) 0.0327(12) 0.0075(10) 0.0077(11) 0.0172(11) C16 0.0458(15) 0.0521(16) 0.0448(15) 0.0079(12) -0.0031(12) 0.0117(13) C17 0.0411(14) 0.0398(14) 0.0553(16) 0.0065(12) 0.0019(12) 0.0071(11) _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 O6 H4W 0.8500 . ? O6 H3W 0.8500 . ? O6 H6W 0.6625 . ? O6' H5W 0.8500 . ? O6' H6W 0.8501 . ? Zn1 O1 1.9838(15) . ? Zn1 O4 1.9848(15) 1_565 ? Zn1 N1 2.017(2) . ? Zn1 N4 2.018(2) . ? O1 C7 1.277(3) . ? O2 C7 1.227(3) . ? O3 C8 1.245(3) . ? O4 C8 1.277(3) . ? O4 Zn1 1.9848(15) 1_545 ? O5 H1W 0.8500 . ? O5 H2W 0.8500 . ? N1 C10 1.326(3) . ? N1 C11 1.349(3) . ? N2 C10 1.312(3) . ? N2 N3 1.359(3) . ? N2 C12 1.465(3) . ? N3 C11 1.307(3) . ? N4 C15 1.320(3) . ? N4 C14 1.350(3) . ? N5 C15 1.314(3) . ? N5 N6 1.365(3) . ? N5 C16 1.460(3) . ? N6 C14 1.303(3) . ? C1 C6 1.383(3) . ? C1 C2 1.384(3) . ? C1 C7 1.501(3) . ? C2 C3 1.385(3) . ? C2 H2 0.9300 . ? C3 C4 1.387(3) . ? C3 C8 1.501(3) . ? C4 C5 1.385(3) . ? C4 H4 0.9300 . ? C5 C6 1.387(3) . ? C5 C9 1.518(4) . ? C6 H6 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.524(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C17 1.518(4) 2_566 ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.513(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C13 1.518(4) 2_566 ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? 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 H4W O6 H3W 112.9 . . ? H4W O6 H6W 160.2 . . ? H3W O6 H6W 86.5 . . ? H5W O6' H6W 109.9 . . ? O1 Zn1 O4 100.17(6) . 1_565 ? O1 Zn1 N1 110.51(7) . . ? O4 Zn1 N1 114.13(7) 1_565 . ? O1 Zn1 N4 106.90(7) . . ? O4 Zn1 N4 111.23(7) 1_565 . ? N1 Zn1 N4 112.94(8) . . ? C7 O1 Zn1 110.62(14) . . ? C8 O4 Zn1 106.94(14) . 1_545 ? H1W O5 H2W 111.6 . . ? C10 N1 C11 102.6(2) . . ? C10 N1 Zn1 127.95(16) . . ? C11 N1 Zn1 129.02(17) . . ? C10 N2 N3 109.4(2) . . ? C10 N2 C12 128.9(2) . . ? N3 N2 C12 121.7(2) . . ? C11 N3 N2 103.0(2) . . ? C15 N4 C14 102.9(2) . . ? C15 N4 Zn1 124.16(16) . . ? C14 N4 Zn1 132.93(17) . . ? C15 N5 N6 109.9(2) . . ? C15 N5 C16 127.9(2) . . ? N6 N5 C16 122.3(2) . . ? C14 N6 N5 102.2(2) . . ? C6 C1 C2 119.44(19) . . ? C6 C1 C7 121.11(19) . . ? C2 C1 C7 119.35(19) . . ? C1 C2 C3 120.8(2) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C2 C3 C4 118.77(19) . . ? C2 C3 C8 120.20(19) . . ? C4 C3 C8 120.93(19) . . ? C5 C4 C3 121.5(2) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 118.5(2) . . ? C4 C5 C9 120.8(2) . . ? C6 C5 C9 120.7(2) . . ? C1 C6 C5 121.0(2) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? O2 C7 O1 122.1(2) . . ? O2 C7 C1 119.6(2) . . ? O1 C7 C1 118.25(19) . . ? O3 C8 O4 122.2(2) . . ? O3 C8 C3 120.04(19) . . ? O4 C8 C3 117.69(19) . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 N1 110.7(2) . . ? N2 C10 H10 124.7 . . ? N1 C10 H10 124.7 . . ? N3 C11 N1 114.3(2) . . ? N3 C11 H11 122.8 . . ? N1 C11 H11 122.8 . . ? N2 C12 C13 112.6(2) . . ? N2 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? N2 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C17 C13 C12 114.4(2) 2_566 . ? C17 C13 H13A 108.6 2_566 . ? C12 C13 H13A 108.6 . . ? C17 C13 H13B 108.6 2_566 . ? C12 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? N6 C14 N4 114.8(2) . . ? N6 C14 H14 122.6 . . ? N4 C14 H14 122.6 . . ? N5 C15 N4 110.2(2) . . ? N5 C15 H15 124.9 . . ? N4 C15 H15 124.9 . . ? N5 C16 C17 113.1(2) . . ? N5 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? N5 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C16 C17 C13 114.3(2) . 2_566 ? C16 C17 H17A 108.7 . . ? C13 C17 H17A 108.7 2_566 . ? C16 C17 H17B 108.7 . . ? C13 C17 H17B 108.7 2_566 . ? H17A C17 H17B 107.6 . . ? 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 O4 Zn1 O1 C7 -176.15(16) 1_565 . . . ? N1 Zn1 O1 C7 63.15(18) . . . . ? N4 Zn1 O1 C7 -60.11(18) . . . . ? O1 Zn1 N1 C10 4.3(2) . . . . ? O4 Zn1 N1 C10 -107.7(2) 1_565 . . . ? N4 Zn1 N1 C10 124.0(2) . . . . ? O1 Zn1 N1 C11 -167.0(2) . . . . ? O4 Zn1 N1 C11 81.0(2) 1_565 . . . ? N4 Zn1 N1 C11 -47.3(2) . . . . ? C10 N2 N3 C11 0.0(3) . . . . ? C12 N2 N3 C11 -178.4(2) . . . . ? O1 Zn1 N4 C15 -8.0(2) . . . . ? O4 Zn1 N4 C15 100.47(19) 1_565 . . . ? N1 Zn1 N4 C15 -129.70(18) . . . . ? O1 Zn1 N4 C14 172.9(2) . . . . ? O4 Zn1 N4 C14 -78.6(2) 1_565 . . . ? N1 Zn1 N4 C14 51.2(2) . . . . ? C15 N5 N6 C14 -0.3(3) . . . . ? C16 N5 N6 C14 179.2(2) . . . . ? C6 C1 C2 C3 0.7(3) . . . . ? C7 C1 C2 C3 -175.7(2) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C1 C2 C3 C8 175.8(2) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C8 C3 C4 C5 -176.1(2) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C3 C4 C5 C9 178.7(3) . . . . ? C2 C1 C6 C5 -0.6(4) . . . . ? C7 C1 C6 C5 175.8(2) . . . . ? C4 C5 C6 C1 0.3(4) . . . . ? C9 C5 C6 C1 -178.6(3) . . . . ? Zn1 O1 C7 O2 -4.4(3) . . . . ? Zn1 O1 C7 C1 177.45(16) . . . . ? C6 C1 C7 O2 -172.4(2) . . . . ? C2 C1 C7 O2 4.0(4) . . . . ? C6 C1 C7 O1 5.8(3) . . . . ? C2 C1 C7 O1 -177.8(2) . . . . ? Zn1 O4 C8 O3 -0.6(3) 1_545 . . . ? Zn1 O4 C8 C3 177.48(15) 1_545 . . . ? C2 C3 C8 O3 -1.7(3) . . . . ? C4 C3 C8 O3 174.6(2) . . . . ? C2 C3 C8 O4 -179.8(2) . . . . ? C4 C3 C8 O4 -3.5(3) . . . . ? N3 N2 C10 N1 -0.5(3) . . . . ? C12 N2 C10 N1 177.7(2) . . . . ? C11 N1 C10 N2 0.8(3) . . . . ? Zn1 N1 C10 N2 -172.30(16) . . . . ? N2 N3 C11 N1 0.5(3) . . . . ? C10 N1 C11 N3 -0.8(3) . . . . ? Zn1 N1 C11 N3 172.2(2) . . . . ? C10 N2 C12 C13 -99.9(3) . . . . ? N3 N2 C12 C13 78.1(3) . . . . ? N2 C12 C13 C17 -73.8(3) . . . 2_566 ? N5 N6 C14 N4 0.1(3) . . . . ? C15 N4 C14 N6 0.1(3) . . . . ? Zn1 N4 C14 N6 179.33(18) . . . . ? N6 N5 C15 N4 0.3(3) . . . . ? C16 N5 C15 N4 -179.1(2) . . . . ? C14 N4 C15 N5 -0.3(3) . . . . ? Zn1 N4 C15 N5 -179.59(15) . . . . ? C15 N5 C16 C17 101.9(3) . . . . ? N6 N5 C16 C17 -77.4(3) . . . . ? N5 C16 C17 C13 76.2(3) . . . 2_566 ? 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 O5 H2W O3 0.85 1.98 2.802(3) 163.4 . O5 H1W O6 0.85 2.15 2.977(8) 164.1 1_455 O5 H1W O6' 0.85 2.16 2.959(9) 155.9 1_455 O6' H5W O2 0.85 1.92 2.657(6) 144.7 1_655 O6 H3W O2 0.85 2.07 2.709(6) 131.9 1_655 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.290 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 960214' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H30 N9 O8 Zn2' _chemical_formula_weight 775.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.879(4) _cell_length_b 8.2185(18) _cell_length_c 22.862(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.936(2) _cell_angle_gamma 90.00 _cell_volume 3167.3(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8781 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 25.49 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1588 _exptl_absorpt_coefficient_mu 1.581 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5633 _exptl_absorpt_correction_T_max 0.7639 _exptl_absorpt_process_details sadabs _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 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 23304 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.49 _reflns_number_total 5884 _reflns_number_gt 5014 _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^)+(0.0302P)^2^+1.6008P] 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 5884 _refine_ls_number_parameters 444 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0648 _refine_ls_wR_factor_gt 0.0615 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 1.032013(14) 0.12750(3) 0.230273(10) 0.02723(7) Uani 1 1 d . . . Zn2 Zn 0.643478(14) -0.20936(3) 0.451788(10) 0.02850(7) Uani 1 1 d . . . O1 O 0.96361(9) 0.38795(17) 0.28133(7) 0.0374(4) Uani 1 1 d . . . O2 O 0.94426(8) 0.12433(16) 0.28626(6) 0.0288(3) Uani 1 1 d . . . O3 O 0.72518(10) -0.08243(19) 0.40745(7) 0.0433(4) Uani 1 1 d . . . O4 O 0.67721(10) 0.0833(2) 0.47222(7) 0.0517(5) Uani 1 1 d . . . O5 O 0.68541(9) -0.2619(2) 0.52986(6) 0.0385(4) Uani 1 1 d . . . O6 O 0.57894(10) -0.4156(2) 0.54131(7) 0.0483(4) Uani 1 1 d . . . O7 O 0.85893(11) -0.2337(2) 0.77894(9) 0.0573(5) Uani 1 1 d . . . O8 O 0.88550(12) -0.1818(3) 0.68914(10) 0.0768(7) Uani 1 1 d . . . N1 N 0.53163(10) -0.1310(2) 0.43389(7) 0.0306(4) Uani 1 1 d . . . N2 N 0.40677(10) -0.1091(2) 0.40747(7) 0.0335(4) Uani 1 1 d . . . N3 N 0.43928(12) 0.0373(2) 0.39445(9) 0.0440(5) Uani 1 1 d . . . N4 N 0.32325(11) -0.0588(2) 0.17713(8) 0.0332(4) Uani 1 1 d . . . N5 N 0.38411(12) -0.1374(2) 0.15195(9) 0.0435(5) Uani 1 1 d . . . N6 N 0.35134(10) 0.0916(2) 0.10303(7) 0.0310(4) Uani 1 1 d . . . N7 N 0.97104(10) 0.2093(2) 0.15723(7) 0.0307(4) Uani 1 1 d . . . N8 N 0.92245(12) 0.3697(2) 0.08950(8) 0.0387(4) Uani 1 1 d . . . N9 N 0.88143(13) 0.2279(3) 0.08266(10) 0.0566(6) Uani 1 1 d . . . C1 C 0.88313(11) 0.2851(2) 0.35648(8) 0.0244(4) Uani 1 1 d . . . C2 C 0.83085(12) 0.1610(2) 0.37088(8) 0.0262(4) Uani 1 1 d . . . H2 H 0.8280 0.0655 0.3490 0.031 Uiso 1 1 calc R . . C3 C 0.78329(12) 0.1815(3) 0.41800(8) 0.0271(4) Uani 1 1 d . . . C4 C 0.79052(12) 0.3220(3) 0.45189(9) 0.0306(5) Uani 1 1 d . . . H4 H 0.7582 0.3350 0.4833 0.037 Uiso 1 1 calc R . . C5 C 0.84472(12) 0.4431(3) 0.43997(9) 0.0310(5) Uani 1 1 d . . . C6 C 0.88974(12) 0.4233(3) 0.39127(9) 0.0305(5) Uani 1 1 d . . . H6 H 0.9252 0.5046 0.3818 0.037 Uiso 1 1 calc R . . C7 C 0.93298(11) 0.2661(2) 0.30466(9) 0.0250(4) Uani 1 1 d . . . C8 C 0.72437(13) 0.0534(3) 0.43389(9) 0.0338(5) Uani 1 1 d . . . C9 C 0.85492(16) 0.5925(3) 0.47775(11) 0.0494(7) Uani 1 1 d . . . H9A H 0.8201 0.5860 0.5096 0.074 Uiso 1 1 calc R . . H9B H 0.8423 0.6876 0.4547 0.074 Uiso 1 1 calc R . . H9C H 0.9089 0.5991 0.4930 0.074 Uiso 1 1 calc R . . C10 C 0.66627(12) -0.3625(2) 0.62445(9) 0.0283(4) Uani 1 1 d . . . C11 C 0.74097(12) -0.3101(3) 0.64428(9) 0.0315(5) Uani 1 1 d . . . H11 H 0.7765 -0.2718 0.6177 0.038 Uiso 1 1 calc R . . C12 C 0.76307(13) -0.3145(3) 0.70389(10) 0.0336(5) Uani 1 1 d . . . C13 C 0.71000(14) -0.3742(3) 0.74314(10) 0.0366(5) Uani 1 1 d . . . H13 H 0.7255 -0.3810 0.7827 0.044 Uiso 1 1 calc R . . C14 C 0.63434(14) -0.4238(3) 0.72438(10) 0.0368(5) Uani 1 1 d . . . C15 C 0.61346(13) -0.4173(3) 0.66461(9) 0.0344(5) Uani 1 1 d . . . H15 H 0.5630 -0.4506 0.6514 0.041 Uiso 1 1 calc R . . C16 C 0.64014(13) -0.3491(3) 0.56040(9) 0.0315(5) Uani 1 1 d . . . C17 C 0.84088(15) -0.2404(3) 0.72468(13) 0.0485(7) Uani 1 1 d . . . C18 C 0.57463(17) -0.4777(4) 0.76767(12) 0.0608(8) Uani 1 1 d . . . H18A H 0.5610 -0.3871 0.7917 0.091 Uiso 1 1 calc R . . H18B H 0.5973 -0.5628 0.7920 0.091 Uiso 1 1 calc R . . H18C H 0.5278 -0.5175 0.7468 0.091 Uiso 1 1 calc R . . C19 C 0.51379(14) 0.0180(3) 0.41094(10) 0.0390(5) Uani 1 1 d . . . H19 H 0.5515 0.0993 0.4073 0.047 Uiso 1 1 calc R . . C20 C 0.46199(13) -0.2070(3) 0.43094(9) 0.0339(5) Uani 1 1 d . . . H20 H 0.4534 -0.3129 0.4435 0.041 Uiso 1 1 calc R . . C21 C 0.32117(13) -0.1306(4) 0.39750(10) 0.0450(6) Uani 1 1 d . . . H21A H 0.2951 -0.0306 0.4082 0.054 Uiso 1 1 calc R . . H21B H 0.3039 -0.2154 0.4235 0.054 Uiso 1 1 calc R . . C22 C 0.29406(14) -0.1741(3) 0.33589(10) 0.0425(6) Uani 1 1 d . . . H22A H 0.2376 -0.1518 0.3314 0.051 Uiso 1 1 calc R . . H22B H 0.3008 -0.2905 0.3313 0.051 Uiso 1 1 calc R . . C23 C 0.33365(13) -0.0912(3) 0.28596(9) 0.0354(5) Uani 1 1 d . . . H23A H 0.3874 -0.1314 0.2837 0.042 Uiso 1 1 calc R . . H23B H 0.3361 0.0252 0.2929 0.042 Uiso 1 1 calc R . . C24 C 0.28704(14) -0.1251(3) 0.22889(9) 0.0391(5) Uani 1 1 d . . . H24A H 0.2814 -0.2419 0.2242 0.047 Uiso 1 1 calc R . . H24B H 0.2343 -0.0795 0.2311 0.047 Uiso 1 1 calc R . . C25 C 0.30440(13) 0.0751(3) 0.14744(9) 0.0327(5) Uani 1 1 d . . . H25 H 0.2642 0.1470 0.1564 0.039 Uiso 1 1 calc R . . C26 C 0.39837(13) -0.0422(3) 0.10748(10) 0.0382(5) Uani 1 1 d . . . H26 H 0.4373 -0.0647 0.0813 0.046 Uiso 1 1 calc R . . C27 C 0.97508(14) 0.3560(3) 0.13390(9) 0.0371(5) Uani 1 1 d . . . H27 H 1.0099 0.4376 0.1469 0.045 Uiso 1 1 calc R . . C28 C 0.91272(15) 0.1362(3) 0.12425(11) 0.0457(6) Uani 1 1 d . . . H28 H 0.8963 0.0300 0.1306 0.055 Uiso 1 1 calc R . . C29 C 0.90828(17) 0.5056(3) 0.04887(11) 0.0523(7) Uani 1 1 d . . . H29A H 0.9227 0.6068 0.0685 0.063 Uiso 1 1 calc R . . H29B H 0.8522 0.5106 0.0373 0.063 Uiso 1 1 calc R . . C30 C 0.95606(15) 0.4876(3) -0.00557(10) 0.0487(6) Uani 1 1 d . . . H30A H 0.9471 0.3798 -0.0218 0.058 Uiso 1 1 calc R . . H30B H 0.9367 0.5659 -0.0347 0.058 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 0.03057(14) 0.02653(13) 0.02507(13) 0.00031(10) 0.00626(10) 0.00031(10) Zn2 0.03034(14) 0.02981(14) 0.02549(13) 0.00117(10) 0.00279(10) -0.00473(10) O1 0.0507(10) 0.0250(8) 0.0383(9) 0.0022(7) 0.0208(7) -0.0034(7) O2 0.0334(8) 0.0233(8) 0.0305(8) -0.0004(6) 0.0106(6) -0.0001(6) O3 0.0503(10) 0.0359(9) 0.0449(9) 0.0006(8) 0.0124(8) -0.0162(8) O4 0.0497(10) 0.0709(13) 0.0360(9) -0.0049(8) 0.0173(8) -0.0267(9) O5 0.0388(9) 0.0509(10) 0.0262(8) 0.0067(7) 0.0043(7) -0.0056(7) O6 0.0542(11) 0.0502(10) 0.0389(9) 0.0072(8) -0.0137(8) -0.0214(9) O7 0.0494(11) 0.0562(12) 0.0634(12) -0.0178(9) -0.0270(9) 0.0045(9) O8 0.0422(12) 0.0949(17) 0.0915(17) 0.0176(14) -0.0157(11) -0.0258(11) N1 0.0325(10) 0.0291(9) 0.0303(9) 0.0010(8) 0.0015(8) -0.0024(8) N2 0.0326(10) 0.0419(11) 0.0262(9) -0.0001(8) 0.0030(8) -0.0003(8) N3 0.0477(12) 0.0331(11) 0.0507(12) 0.0028(9) -0.0017(10) 0.0015(9) N4 0.0375(10) 0.0338(10) 0.0281(9) 0.0019(8) -0.0001(8) 0.0011(8) N5 0.0446(12) 0.0413(11) 0.0447(12) 0.0074(10) 0.0049(9) 0.0108(9) N6 0.0342(10) 0.0309(10) 0.0279(9) 0.0007(7) 0.0015(8) 0.0029(8) N7 0.0342(10) 0.0302(10) 0.0277(9) -0.0012(8) 0.0025(7) -0.0002(8) N8 0.0461(11) 0.0401(11) 0.0297(10) 0.0029(8) 0.0002(9) 0.0060(9) N9 0.0499(13) 0.0669(16) 0.0515(14) 0.0109(12) -0.0106(11) -0.0166(12) C1 0.0237(10) 0.0258(10) 0.0239(10) 0.0028(8) 0.0036(8) 0.0016(8) C2 0.0268(10) 0.0270(10) 0.0247(10) 0.0014(8) 0.0015(8) -0.0015(8) C3 0.0237(10) 0.0337(11) 0.0238(10) 0.0047(9) 0.0010(8) -0.0037(8) C4 0.0288(11) 0.0393(12) 0.0243(10) 0.0022(9) 0.0069(8) 0.0012(9) C5 0.0336(11) 0.0292(11) 0.0307(11) -0.0026(9) 0.0070(9) 0.0010(9) C6 0.0316(11) 0.0260(11) 0.0347(12) 0.0017(9) 0.0081(9) -0.0055(9) C7 0.0237(10) 0.0252(11) 0.0264(10) 0.0031(8) 0.0035(8) 0.0010(8) C8 0.0340(12) 0.0414(13) 0.0255(11) 0.0076(10) -0.0023(9) -0.0108(10) C9 0.0599(17) 0.0397(14) 0.0503(15) -0.0133(12) 0.0198(13) -0.0068(12) C10 0.0307(11) 0.0267(11) 0.0275(11) 0.0022(9) 0.0000(9) 0.0015(9) C11 0.0300(11) 0.0296(11) 0.0350(12) 0.0027(9) 0.0032(9) 0.0000(9) C12 0.0310(12) 0.0296(12) 0.0392(12) -0.0025(10) -0.0068(9) 0.0048(9) C13 0.0468(14) 0.0349(12) 0.0272(11) -0.0011(9) -0.0062(10) 0.0096(10) C14 0.0409(13) 0.0386(13) 0.0314(12) 0.0065(10) 0.0064(10) 0.0020(10) C15 0.0284(11) 0.0393(13) 0.0353(12) 0.0068(10) -0.0017(9) -0.0033(9) C16 0.0352(12) 0.0288(11) 0.0303(11) 0.0018(9) 0.0012(9) 0.0007(9) C17 0.0405(14) 0.0308(13) 0.0719(19) -0.0049(12) -0.0199(14) 0.0074(11) C18 0.0589(17) 0.083(2) 0.0420(15) 0.0160(15) 0.0161(13) 0.0000(15) C19 0.0413(13) 0.0280(12) 0.0473(14) 0.0006(10) -0.0016(11) -0.0054(10) C20 0.0370(12) 0.0339(12) 0.0308(11) 0.0041(10) 0.0024(9) -0.0036(10) C21 0.0304(12) 0.0721(18) 0.0328(12) 0.0002(12) 0.0051(10) -0.0032(12) C22 0.0402(13) 0.0549(16) 0.0321(12) 0.0039(11) -0.0005(10) -0.0067(11) C23 0.0347(12) 0.0418(13) 0.0296(11) 0.0006(10) 0.0005(9) -0.0024(10) C24 0.0401(13) 0.0458(14) 0.0313(12) 0.0051(10) 0.0005(10) -0.0052(11) C25 0.0378(12) 0.0307(11) 0.0293(11) -0.0032(9) -0.0009(9) 0.0048(9) C26 0.0372(12) 0.0387(13) 0.0392(13) 0.0036(10) 0.0064(10) 0.0064(10) C27 0.0504(14) 0.0325(12) 0.0282(11) -0.0033(10) -0.0004(10) -0.0039(10) C28 0.0463(14) 0.0443(14) 0.0453(14) 0.0074(12) -0.0075(11) -0.0140(12) C29 0.0620(17) 0.0525(16) 0.0425(14) 0.0147(12) 0.0032(12) 0.0201(13) C30 0.0611(16) 0.0492(15) 0.0351(13) 0.0104(11) -0.0055(12) 0.0029(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.9884(15) 2_745 ? Zn1 O2 2.0067(14) . ? Zn1 N7 2.0307(18) . ? Zn1 O7 2.058(2) 3_756 ? Zn1 O8 2.295(2) 3_756 ? Zn1 C17 2.510(3) 3_756 ? Zn2 O5 1.9349(15) . ? Zn2 N1 2.0167(18) . ? Zn2 O3 2.0398(15) . ? Zn2 N6 2.0654(18) 2_645 ? Zn2 C8 2.599(2) . ? O1 C7 1.258(2) . ? O1 Zn1 1.9884(15) 2_755 ? O2 C7 1.257(2) . ? O3 C8 1.270(3) . ? O4 C8 1.238(3) . ? O5 C16 1.280(3) . ? O6 C16 1.229(3) . ? O7 C17 1.263(3) . ? O7 Zn1 2.058(2) 3_756 ? O8 C17 1.234(3) . ? O8 Zn1 2.295(2) 3_756 ? N1 C20 1.330(3) . ? N1 C19 1.360(3) . ? N2 C20 1.324(3) . ? N2 N3 1.362(3) . ? N2 C21 1.462(3) . ? N3 C19 1.304(3) . ? N4 C25 1.323(3) . ? N4 N5 1.365(3) . ? N4 C24 1.464(3) . ? N5 C26 1.314(3) . ? N6 C25 1.326(3) . ? N6 C26 1.357(3) . ? N6 Zn2 2.0654(17) 2_655 ? N7 C27 1.322(3) . ? N7 C28 1.350(3) . ? N8 C27 1.319(3) . ? N8 N9 1.360(3) . ? N8 C29 1.465(3) . ? N9 C28 1.303(3) . ? C1 C6 1.387(3) . ? C1 C2 1.399(3) . ? C1 C7 1.496(3) . ? C2 C3 1.386(3) . ? C2 H2 0.9300 . ? C3 C4 1.392(3) . ? C3 C8 1.505(3) . ? C4 C5 1.389(3) . ? C4 H4 0.9300 . ? C5 C6 1.389(3) . ? C5 C9 1.506(3) . ? C6 H6 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.386(3) . ? C10 C15 1.387(3) . ? C10 C16 1.512(3) . ? C11 C12 1.395(3) . ? C11 H11 0.9300 . ? C12 C13 1.390(3) . ? C12 C17 1.502(3) . ? C13 C14 1.387(3) . ? C13 H13 0.9300 . ? C14 C15 1.395(3) . ? C14 C18 1.515(3) . ? C15 H15 0.9300 . ? C17 Zn1 2.510(3) 3_756 ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.502(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.514(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.515(3) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 C30 1.524(4) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C30 1.506(5) 3_765 ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? 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 O2 96.08(6) 2_745 . ? O1 Zn1 N7 103.82(7) 2_745 . ? O2 Zn1 N7 99.75(7) . . ? O1 Zn1 O7 111.51(7) 2_745 3_756 ? O2 Zn1 O7 139.83(7) . 3_756 ? N7 Zn1 O7 101.18(7) . 3_756 ? O1 Zn1 O8 105.92(8) 2_745 3_756 ? O2 Zn1 O8 85.86(7) . 3_756 ? N7 Zn1 O8 148.95(8) . 3_756 ? O7 Zn1 O8 59.38(8) 3_756 3_756 ? O1 Zn1 C17 112.59(7) 2_745 3_756 ? O2 Zn1 C17 112.73(8) . 3_756 ? N7 Zn1 C17 126.99(8) . 3_756 ? O7 Zn1 C17 30.09(9) 3_756 3_756 ? O8 Zn1 C17 29.32(8) 3_756 3_756 ? O5 Zn2 N1 123.57(7) . . ? O5 Zn2 O3 110.36(7) . . ? N1 Zn2 O3 112.68(7) . . ? O5 Zn2 N6 110.98(7) . 2_645 ? N1 Zn2 N6 101.42(7) . 2_645 ? O3 Zn2 N6 93.03(7) . 2_645 ? O5 Zn2 C8 99.23(7) . . ? N1 Zn2 C8 101.34(7) . . ? O3 Zn2 C8 28.68(7) . . ? N6 Zn2 C8 121.59(7) 2_645 . ? C7 O1 Zn1 149.70(14) . 2_755 ? C7 O2 Zn1 109.32(12) . . ? C8 O3 Zn2 100.90(13) . . ? C16 O5 Zn2 115.31(14) . . ? C17 O7 Zn1 95.17(18) . 3_756 ? C17 O8 Zn1 85.02(17) . 3_756 ? C20 N1 C19 103.05(18) . . ? C20 N1 Zn2 132.55(15) . . ? C19 N1 Zn2 123.52(15) . . ? C20 N2 N3 110.02(18) . . ? C20 N2 C21 131.3(2) . . ? N3 N2 C21 118.61(19) . . ? C19 N3 N2 102.89(18) . . ? C25 N4 N5 110.07(18) . . ? C25 N4 C24 128.66(19) . . ? N5 N4 C24 121.26(18) . . ? C26 N5 N4 102.50(18) . . ? C25 N6 C26 103.29(18) . . ? C25 N6 Zn2 126.22(14) . 2_655 ? C26 N6 Zn2 130.14(15) . 2_655 ? C27 N7 C28 103.39(19) . . ? C27 N7 Zn1 126.83(15) . . ? C28 N7 Zn1 129.53(15) . . ? C27 N8 N9 109.54(19) . . ? C27 N8 C29 129.4(2) . . ? N9 N8 C29 121.0(2) . . ? C28 N9 N8 103.1(2) . . ? C6 C1 C2 119.67(18) . . ? C6 C1 C7 120.49(18) . . ? C2 C1 C7 119.82(18) . . ? C3 C2 C1 119.44(19) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 119.70(18) . . ? C2 C3 C8 121.23(19) . . ? C4 C3 C8 119.07(18) . . ? C5 C4 C3 121.69(19) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C4 C5 C6 117.77(19) . . ? C4 C5 C9 121.94(19) . . ? C6 C5 C9 120.29(19) . . ? C1 C6 C5 121.62(19) . . ? C1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? O2 C7 O1 121.56(18) . . ? O2 C7 C1 117.57(17) . . ? O1 C7 C1 120.85(18) . . ? O4 C8 O3 122.3(2) . . ? O4 C8 C3 119.2(2) . . ? O3 C8 C3 118.46(19) . . ? O4 C8 Zn2 72.03(13) . . ? O3 C8 Zn2 50.42(10) . . ? C3 C8 Zn2 167.98(17) . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 119.28(19) . . ? C11 C10 C16 120.62(19) . . ? C15 C10 C16 119.95(18) . . ? C10 C11 C12 120.3(2) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 119.4(2) . . ? C13 C12 C17 121.4(2) . . ? C11 C12 C17 119.0(2) . . ? C14 C13 C12 121.2(2) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 118.3(2) . . ? C13 C14 C18 121.1(2) . . ? C15 C14 C18 120.5(2) . . ? C10 C15 C14 121.5(2) . . ? C10 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? O6 C16 O5 124.7(2) . . ? O6 C16 C10 120.64(19) . . ? O5 C16 C10 114.61(18) . . ? O8 C17 O7 120.3(2) . . ? O8 C17 C12 120.2(2) . . ? O7 C17 C12 119.4(3) . . ? O8 C17 Zn1 65.66(15) . 3_756 ? O7 C17 Zn1 54.74(13) . 3_756 ? C12 C17 Zn1 174.1(2) . 3_756 ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 C19 N1 114.3(2) . . ? N3 C19 H19 122.8 . . ? N1 C19 H19 122.8 . . ? N2 C20 N1 109.71(19) . . ? N2 C20 H20 125.1 . . ? N1 C20 H20 125.1 . . ? N2 C21 C22 115.23(19) . . ? N2 C21 H21A 108.5 . . ? C22 C21 H21A 108.5 . . ? N2 C21 H21B 108.5 . . ? C22 C21 H21B 108.5 . . ? H21A C21 H21B 107.5 . . ? C21 C22 C23 118.4(2) . . ? C21 C22 H22A 107.7 . . ? C23 C22 H22A 107.7 . . ? C21 C22 H22B 107.7 . . ? C23 C22 H22B 107.7 . . ? H22A C22 H22B 107.1 . . ? C22 C23 C24 109.69(18) . . ? C22 C23 H23A 109.7 . . ? C24 C23 H23A 109.7 . . ? C22 C23 H23B 109.7 . . ? C24 C23 H23B 109.7 . . ? H23A C23 H23B 108.2 . . ? N4 C24 C23 114.07(18) . . ? N4 C24 H24A 108.7 . . ? C23 C24 H24A 108.7 . . ? N4 C24 H24B 108.7 . . ? C23 C24 H24B 108.7 . . ? H24A C24 H24B 107.6 . . ? N4 C25 N6 109.90(19) . . ? N4 C25 H25 125.1 . . ? N6 C25 H25 125.1 . . ? N5 C26 N6 114.2(2) . . ? N5 C26 H26 122.9 . . ? N6 C26 H26 122.9 . . ? N8 C27 N7 110.0(2) . . ? N8 C27 H27 125.0 . . ? N7 C27 H27 125.0 . . ? N9 C28 N7 114.0(2) . . ? N9 C28 H28 123.0 . . ? N7 C28 H28 123.0 . . ? N8 C29 C30 111.6(2) . . ? N8 C29 H29A 109.3 . . ? C30 C29 H29A 109.3 . . ? N8 C29 H29B 109.3 . . ? C30 C29 H29B 109.3 . . ? H29A C29 H29B 108.0 . . ? C30 C30 C29 114.0(3) 3_765 . ? C30 C30 H30A 108.8 3_765 . ? C29 C30 H30A 108.8 . . ? C30 C30 H30B 108.8 3_765 . ? C29 C30 H30B 108.8 . . ? H30A C30 H30B 107.6 . . ? 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 O1 Zn1 O2 C7 175.15(13) 2_745 . . . ? N7 Zn1 O2 C7 -79.66(14) . . . . ? O7 Zn1 O2 C7 40.89(17) 3_756 . . . ? O8 Zn1 O2 C7 69.55(14) 3_756 . . . ? C17 Zn1 O2 C7 57.54(15) 3_756 . . . ? O5 Zn2 O3 C8 -71.23(15) . . . . ? N1 Zn2 O3 C8 71.35(15) . . . . ? N6 Zn2 O3 C8 175.06(14) 2_645 . . . ? N1 Zn2 O5 C16 45.74(18) . . . . ? O3 Zn2 O5 C16 -176.55(14) . . . . ? N6 Zn2 O5 C16 -74.86(16) 2_645 . . . ? C8 Zn2 O5 C16 156.04(15) . . . . ? O5 Zn2 N1 C20 -75.7(2) . . . . ? O3 Zn2 N1 C20 147.41(19) . . . . ? N6 Zn2 N1 C20 49.2(2) 2_645 . . . ? C8 Zn2 N1 C20 175.04(19) . . . . ? O5 Zn2 N1 C19 116.94(17) . . . . ? O3 Zn2 N1 C19 -19.92(19) . . . . ? N6 Zn2 N1 C19 -118.14(17) 2_645 . . . ? C8 Zn2 N1 C19 7.71(18) . . . . ? C20 N2 N3 C19 0.3(2) . . . . ? C21 N2 N3 C19 176.90(19) . . . . ? C25 N4 N5 C26 0.2(2) . . . . ? C24 N4 N5 C26 179.1(2) . . . . ? O1 Zn1 N7 C27 -154.80(18) 2_745 . . . ? O2 Zn1 N7 C27 106.41(18) . . . . ? O7 Zn1 N7 C27 -39.11(19) 3_756 . . . ? O8 Zn1 N7 C27 8.2(3) 3_756 . . . ? C17 Zn1 N7 C27 -21.9(2) 3_756 . . . ? O1 Zn1 N7 C28 31.9(2) 2_745 . . . ? O2 Zn1 N7 C28 -66.9(2) . . . . ? O7 Zn1 N7 C28 147.6(2) 3_756 . . . ? O8 Zn1 N7 C28 -165.1(2) 3_756 . . . ? C17 Zn1 N7 C28 164.8(2) 3_756 . . . ? C27 N8 N9 C28 0.0(3) . . . . ? C29 N8 N9 C28 176.8(2) . . . . ? C6 C1 C2 C3 3.4(3) . . . . ? C7 C1 C2 C3 -178.22(18) . . . . ? C1 C2 C3 C4 -2.8(3) . . . . ? C1 C2 C3 C8 178.05(18) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C8 C3 C4 C5 178.93(19) . . . . ? C3 C4 C5 C6 2.7(3) . . . . ? C3 C4 C5 C9 -177.7(2) . . . . ? C2 C1 C6 C5 -0.9(3) . . . . ? C7 C1 C6 C5 -179.34(19) . . . . ? C4 C5 C6 C1 -2.0(3) . . . . ? C9 C5 C6 C1 178.3(2) . . . . ? Zn1 O2 C7 O1 11.9(2) . . . . ? Zn1 O2 C7 C1 -166.69(14) . . . . ? Zn1 O1 C7 O2 164.5(2) 2_755 . . . ? Zn1 O1 C7 C1 -17.0(4) 2_755 . . . ? C6 C1 C7 O2 157.70(19) . . . . ? C2 C1 C7 O2 -20.7(3) . . . . ? C6 C1 C7 O1 -20.9(3) . . . . ? C2 C1 C7 O1 160.70(19) . . . . ? Zn2 O3 C8 O4 -5.2(3) . . . . ? Zn2 O3 C8 C3 174.47(15) . . . . ? C2 C3 C8 O4 -172.4(2) . . . . ? C4 C3 C8 O4 8.4(3) . . . . ? C2 C3 C8 O3 7.9(3) . . . . ? C4 C3 C8 O3 -171.29(19) . . . . ? C2 C3 C8 Zn2 28.8(8) . . . . ? C4 C3 C8 Zn2 -150.4(6) . . . . ? O5 Zn2 C8 O4 -68.71(14) . . . . ? N1 Zn2 C8 O4 58.44(14) . . . . ? O3 Zn2 C8 O4 175.4(2) . . . . ? N6 Zn2 C8 O4 169.57(12) 2_645 . . . ? O5 Zn2 C8 O3 115.93(14) . . . . ? N1 Zn2 C8 O3 -116.92(14) . . . . ? N6 Zn2 C8 O3 -5.79(17) 2_645 . . . ? O5 Zn2 C8 C3 91.9(7) . . . . ? N1 Zn2 C8 C3 -141.0(7) . . . . ? O3 Zn2 C8 C3 -24.0(6) . . . . ? N6 Zn2 C8 C3 -29.8(7) 2_645 . . . ? C15 C10 C11 C12 0.8(3) . . . . ? C16 C10 C11 C12 176.44(19) . . . . ? C10 C11 C12 C13 1.0(3) . . . . ? C10 C11 C12 C17 -173.5(2) . . . . ? C11 C12 C13 C14 -2.5(3) . . . . ? C17 C12 C13 C14 171.9(2) . . . . ? C12 C13 C14 C15 2.1(3) . . . . ? C12 C13 C14 C18 -175.7(2) . . . . ? C11 C10 C15 C14 -1.2(3) . . . . ? C16 C10 C15 C14 -176.8(2) . . . . ? C13 C14 C15 C10 -0.2(3) . . . . ? C18 C14 C15 C10 177.6(2) . . . . ? Zn2 O5 C16 O6 9.5(3) . . . . ? Zn2 O5 C16 C10 -168.97(14) . . . . ? C11 C10 C16 O6 169.7(2) . . . . ? C15 C10 C16 O6 -14.7(3) . . . . ? C11 C10 C16 O5 -11.8(3) . . . . ? C15 C10 C16 O5 163.8(2) . . . . ? Zn1 O8 C17 O7 3.2(2) 3_756 . . . ? Zn1 O8 C17 C12 -179.2(2) 3_756 . . . ? Zn1 O7 C17 O8 -3.6(3) 3_756 . . . ? Zn1 O7 C17 C12 178.83(18) 3_756 . . . ? C13 C12 C17 O8 -176.8(2) . . . . ? C11 C12 C17 O8 -2.4(3) . . . . ? C13 C12 C17 O7 0.7(3) . . . . ? C11 C12 C17 O7 175.1(2) . . . . ? C13 C12 C17 Zn1 10.1(18) . . . 3_756 ? C11 C12 C17 Zn1 -175.6(15) . . . 3_756 ? N2 N3 C19 N1 -0.1(3) . . . . ? C20 N1 C19 N3 -0.1(3) . . . . ? Zn2 N1 C19 N3 170.35(16) . . . . ? N3 N2 C20 N1 -0.4(2) . . . . ? C21 N2 C20 N1 -176.4(2) . . . . ? C19 N1 C20 N2 0.3(2) . . . . ? Zn2 N1 C20 N2 -168.89(14) . . . . ? C20 N2 C21 C22 -100.9(3) . . . . ? N3 N2 C21 C22 83.3(3) . . . . ? N2 C21 C22 C23 -39.9(3) . . . . ? C21 C22 C23 C24 -168.4(2) . . . . ? C25 N4 C24 C23 -100.9(3) . . . . ? N5 N4 C24 C23 80.4(3) . . . . ? C22 C23 C24 N4 -176.3(2) . . . . ? N5 N4 C25 N6 -0.8(2) . . . . ? C24 N4 C25 N6 -179.6(2) . . . . ? C26 N6 C25 N4 1.0(2) . . . . ? Zn2 N6 C25 N4 -172.67(14) 2_655 . . . ? N4 N5 C26 N6 0.5(3) . . . . ? C25 N6 C26 N5 -1.0(3) . . . . ? Zn2 N6 C26 N5 172.36(16) 2_655 . . . ? N9 N8 C27 N7 0.1(3) . . . . ? C29 N8 C27 N7 -176.4(2) . . . . ? C28 N7 C27 N8 -0.2(3) . . . . ? Zn1 N7 C27 N8 -174.87(14) . . . . ? N8 N9 C28 N7 -0.1(3) . . . . ? C27 N7 C28 N9 0.2(3) . . . . ? Zn1 N7 C28 N9 174.67(17) . . . . ? C27 N8 C29 C30 91.8(3) . . . . ? N9 N8 C29 C30 -84.3(3) . . . . ? N8 C29 C30 C30 -70.7(4) . . . 3_765 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.372 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 960215' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 N6 O6 Zn' _chemical_formula_weight 455.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2209(11) _cell_length_b 10.2628(12) _cell_length_c 12.7492(15) _cell_angle_alpha 111.6640(10) _cell_angle_beta 93.5900(10) _cell_angle_gamma 112.6310(10) _cell_volume 1005.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3303 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 25.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 1.267 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5994 _exptl_absorpt_correction_T_max 0.8327 _exptl_absorpt_process_details SADABS _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 7736 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3716 _reflns_number_gt 3245 _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^)+(0.0804P)^2^+1.8747P] 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 3716 _refine_ls_number_parameters 272 _refine_ls_number_restraints 70 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1526 _refine_ls_wR_factor_gt 0.1462 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.138 _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 1.11708(6) 1.08951(5) 0.18014(4) 0.02993(19) Uani 1 1 d . . . O1 O 1.1232(4) 0.8611(4) 0.2464(3) 0.0427(8) Uani 1 1 d . . . O2 O 1.1804(4) 0.9218(3) 0.0996(3) 0.0372(7) Uani 1 1 d . . . O3 O 1.0825(5) 0.3594(4) 0.2318(3) 0.0475(8) Uani 1 1 d . . . O4 O 1.1557(4) 0.2126(3) 0.0904(3) 0.0376(7) Uani 1 1 d . . . O5 O 1.3713(5) 0.5177(4) -0.1340(3) 0.0520(9) Uani 1 1 d . . . O6 O -0.0154(10) 0.5473(10) 0.4122(6) 0.057(2) Uani 0.50 1 d P . . H1W H 0.0539 0.6314 0.4495 0.086 Uiso 0.50 1 d PR . . H2W H 0.0126 0.4896 0.3588 0.086 Uiso 0.50 1 d PR . . O7 O 0.0804(9) 0.8832(11) 0.4623(5) 0.066(2) Uani 0.50 1 d P . . H4W H 0.0827 0.8493 0.3930 0.098 Uiso 0.50 1 d PR . . H3W H 0.1229 0.9788 0.4929 0.098 Uiso 0.50 1 d PR . . N1 N 0.8929(4) 1.0153(4) 0.2095(3) 0.0370(8) Uani 1 1 d U . . N2 N 0.6776(4) 0.8840(4) 0.2537(3) 0.0357(8) Uani 1 1 d U . . N3 N 0.6410(6) 0.9861(6) 0.2265(5) 0.0671(13) Uani 1 1 d U . . N4 N 0.5365(4) 0.7241(4) 0.5145(3) 0.0349(8) Uani 1 1 d . . . N5 N 0.6192(5) 0.6404(5) 0.4698(3) 0.0441(10) Uani 1 1 d . . . N6 N 0.7163(4) 0.7797(4) 0.6624(3) 0.0340(8) Uani 1 1 d . . . C1 C 1.1927(5) 0.6931(4) 0.0967(3) 0.0265(8) Uani 1 1 d . . . C2 C 1.1461(5) 0.5807(4) 0.1400(3) 0.0270(8) Uani 1 1 d . . . H2 H 1.0942 0.5920 0.2007 0.032 Uiso 1 1 calc R . . C3 C 1.1773(5) 0.4514(4) 0.0921(3) 0.0277(8) Uani 1 1 d . . . C4 C 1.2537(5) 0.4350(5) 0.0012(4) 0.0317(9) Uani 1 1 d . . . H4 H 1.2755 0.3490 -0.0304 0.038 Uiso 1 1 calc R . . C5 C 1.2983(5) 0.5462(5) -0.0433(4) 0.0328(9) Uani 1 1 d . . . C6 C 1.2672(5) 0.6758(5) 0.0047(4) 0.0305(9) Uani 1 1 d . . . H6 H 1.2963 0.7503 -0.0248 0.037 Uiso 1 1 calc R . . C7 C 1.1620(5) 0.8341(5) 0.1522(4) 0.0299(9) Uani 1 1 d . . . C8 C 1.1336(5) 0.3340(5) 0.1422(4) 0.0310(9) Uani 1 1 d . . . C9 C 1.4246(8) 0.6298(7) -0.1805(5) 0.0592(15) Uani 1 1 d . . . H9A H 1.3340 0.6425 -0.2084 0.089 Uiso 1 1 calc R . . H9B H 1.4723 0.5946 -0.2436 0.089 Uiso 1 1 calc R . . H9C H 1.5035 0.7279 -0.1210 0.089 Uiso 1 1 calc R . . C10 C 0.8253(5) 0.9042(5) 0.2443(4) 0.0323(9) Uani 1 1 d U . . H10 H 0.8753 0.8479 0.2600 0.039 Uiso 1 1 calc R . . C11 C 0.7763(7) 1.0626(7) 0.1999(6) 0.0638(14) Uani 1 1 d U . . H11 H 0.7893 1.1417 0.1767 0.077 Uiso 1 1 calc R . . C12 C 0.5630(5) 0.7683(5) 0.2860(4) 0.0362(10) Uani 1 1 d . . . H12A H 0.6171 0.7155 0.3094 0.043 Uiso 1 1 calc R . . H12B H 0.4748 0.6907 0.2187 0.043 Uiso 1 1 calc R . . C13 C 0.4950(5) 0.8410(5) 0.3836(4) 0.0353(9) Uani 1 1 d . . . H13A H 0.4160 0.8674 0.3538 0.042 Uiso 1 1 calc R . . H13B H 0.5815 0.9368 0.4422 0.042 Uiso 1 1 calc R . . C14 C 0.4145(5) 0.7310(5) 0.4396(4) 0.0382(10) Uani 1 1 d . . . H14A H 0.3464 0.7674 0.4854 0.046 Uiso 1 1 calc R . . H14B H 0.3464 0.6271 0.3793 0.046 Uiso 1 1 calc R . . C15 C 0.5964(5) 0.8062(5) 0.6290(4) 0.0342(9) Uani 1 1 d . . . H15 H 0.5590 0.8724 0.6780 0.041 Uiso 1 1 calc R . . C16 C 0.7260(6) 0.6774(5) 0.5626(4) 0.0396(10) Uani 1 1 d . . . H16 H 0.8010 0.6368 0.5595 0.047 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 0.0377(3) 0.0267(3) 0.0358(3) 0.0181(2) 0.0133(2) 0.0191(2) O1 0.062(2) 0.0363(17) 0.0449(18) 0.0189(15) 0.0248(16) 0.0327(16) O2 0.0530(19) 0.0291(15) 0.0439(17) 0.0207(14) 0.0153(15) 0.0265(14) O3 0.073(2) 0.0404(18) 0.0473(19) 0.0287(16) 0.0291(18) 0.0313(18) O4 0.0532(19) 0.0272(15) 0.0433(17) 0.0204(13) 0.0131(15) 0.0230(14) O5 0.085(3) 0.051(2) 0.054(2) 0.0342(18) 0.045(2) 0.047(2) O6 0.080(5) 0.089(6) 0.051(4) 0.041(4) 0.049(4) 0.068(5) O7 0.059(5) 0.107(7) 0.017(3) 0.033(4) 0.011(3) 0.018(4) N1 0.0359(18) 0.0391(19) 0.048(2) 0.0262(16) 0.0138(16) 0.0202(15) N2 0.0334(18) 0.0365(18) 0.045(2) 0.0223(16) 0.0112(15) 0.0182(15) N3 0.048(2) 0.071(3) 0.118(4) 0.066(3) 0.027(2) 0.035(2) N4 0.037(2) 0.0335(19) 0.0352(19) 0.0154(16) 0.0107(16) 0.0159(16) N5 0.055(2) 0.043(2) 0.041(2) 0.0148(18) 0.0157(19) 0.030(2) N6 0.040(2) 0.0309(18) 0.0360(19) 0.0165(15) 0.0100(16) 0.0176(16) C1 0.0277(19) 0.0213(18) 0.033(2) 0.0119(16) 0.0036(16) 0.0130(16) C2 0.0281(19) 0.0257(19) 0.030(2) 0.0136(16) 0.0086(16) 0.0127(16) C3 0.029(2) 0.0206(18) 0.033(2) 0.0127(16) 0.0037(16) 0.0098(16) C4 0.043(2) 0.025(2) 0.033(2) 0.0118(17) 0.0095(18) 0.0200(18) C5 0.043(2) 0.031(2) 0.032(2) 0.0144(18) 0.0141(18) 0.0218(19) C6 0.038(2) 0.027(2) 0.034(2) 0.0181(17) 0.0106(18) 0.0168(18) C7 0.031(2) 0.025(2) 0.037(2) 0.0129(17) 0.0083(17) 0.0152(17) C8 0.036(2) 0.026(2) 0.034(2) 0.0160(17) 0.0053(18) 0.0132(17) C9 0.084(4) 0.059(3) 0.059(3) 0.036(3) 0.045(3) 0.040(3) C10 0.036(2) 0.035(2) 0.035(2) 0.0181(17) 0.0113(17) 0.0206(17) C11 0.051(3) 0.067(3) 0.108(4) 0.064(3) 0.025(3) 0.034(2) C12 0.037(2) 0.029(2) 0.041(2) 0.0143(18) 0.0124(19) 0.0125(18) C13 0.036(2) 0.036(2) 0.038(2) 0.0151(19) 0.0095(19) 0.0205(19) C14 0.031(2) 0.044(3) 0.040(2) 0.018(2) 0.0084(19) 0.016(2) C15 0.038(2) 0.033(2) 0.036(2) 0.0167(19) 0.0122(18) 0.0175(19) C16 0.048(3) 0.039(2) 0.040(2) 0.017(2) 0.013(2) 0.027(2) _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 O4 1.950(3) 1_565 ? Zn1 O2 1.975(3) . ? Zn1 N1 2.022(4) . ? Zn1 N6 2.056(4) 2_776 ? O1 C7 1.238(5) . ? O2 C7 1.277(5) . ? O3 C8 1.239(5) . ? O4 C8 1.278(5) . ? O4 Zn1 1.950(3) 1_545 ? O5 C5 1.369(5) . ? O5 C9 1.422(6) . ? O6 H1W 0.7839 . ? O6 H2W 0.8499 . ? O7 H4W 0.8271 . ? O7 H3W 0.8186 . ? N1 C10 1.322(5) . ? N1 C11 1.355(6) . ? N2 C10 1.317(6) . ? N2 N3 1.363(6) . ? N2 C12 1.464(5) . ? N3 C11 1.336(7) . ? N4 C15 1.333(6) . ? N4 N5 1.358(5) . ? N4 C14 1.469(6) . ? N5 C16 1.322(6) . ? N6 C15 1.317(6) . ? N6 C16 1.353(6) . ? N6 Zn1 2.056(4) 2_776 ? C1 C6 1.386(6) . ? C1 C2 1.392(5) . ? C1 C7 1.503(5) . ? C2 C3 1.391(5) . ? C2 H2 0.9300 . ? C3 C4 1.385(6) . ? C3 C8 1.500(5) . ? C4 C5 1.393(6) . ? C4 H4 0.9300 . ? C5 C6 1.393(6) . ? C6 H6 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.507(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.534(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15 0.9300 . ? C16 H16 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 O4 Zn1 O2 105.38(12) 1_565 . ? O4 Zn1 N1 115.04(14) 1_565 . ? O2 Zn1 N1 114.82(14) . . ? O4 Zn1 N6 108.74(14) 1_565 2_776 ? O2 Zn1 N6 103.50(14) . 2_776 ? N1 Zn1 N6 108.62(15) . 2_776 ? C7 O2 Zn1 110.9(3) . . ? C8 O4 Zn1 110.2(3) . 1_545 ? C5 O5 C9 118.3(4) . . ? H1W O6 H2W 113.9 . . ? H4W O7 H3W 111.0 . . ? C10 N1 C11 102.9(4) . . ? C10 N1 Zn1 126.4(3) . . ? C11 N1 Zn1 130.7(3) . . ? C10 N2 N3 110.3(4) . . ? C10 N2 C12 126.8(4) . . ? N3 N2 C12 122.9(4) . . ? C11 N3 N2 101.8(4) . . ? C15 N4 N5 109.6(4) . . ? C15 N4 C14 128.2(4) . . ? N5 N4 C14 121.7(4) . . ? C16 N5 N4 102.8(4) . . ? C15 N6 C16 103.7(4) . . ? C15 N6 Zn1 126.0(3) . 2_776 ? C16 N6 Zn1 128.5(3) . 2_776 ? C6 C1 C2 120.6(4) . . ? C6 C1 C7 120.6(3) . . ? C2 C1 C7 118.8(4) . . ? C3 C2 C1 119.8(4) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C4 C3 C2 119.7(4) . . ? C4 C3 C8 120.5(3) . . ? C2 C3 C8 119.7(4) . . ? C3 C4 C5 120.5(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? O5 C5 C6 124.5(4) . . ? O5 C5 C4 115.7(4) . . ? C6 C5 C4 119.8(4) . . ? C1 C6 C5 119.6(4) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? O1 C7 O2 123.4(4) . . ? O1 C7 C1 119.1(4) . . ? O2 C7 C1 117.6(4) . . ? O3 C8 O4 123.2(4) . . ? O3 C8 C3 119.7(4) . . ? O4 C8 C3 117.1(4) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 N1 110.8(4) . . ? N2 C10 H10 124.6 . . ? N1 C10 H10 124.6 . . ? N3 C11 N1 114.3(5) . . ? N3 C11 H11 122.9 . . ? N1 C11 H11 122.9 . . ? N2 C12 C13 112.3(4) . . ? N2 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? N2 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.9 . . ? C12 C13 C14 111.9(4) . . ? C12 C13 H13A 109.2 . . ? C14 C13 H13A 109.2 . . ? C12 C13 H13B 109.2 . . ? C14 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? N4 C14 C13 110.9(4) . . ? N4 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? N4 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? N6 C15 N4 110.0(4) . . ? N6 C15 H15 125.0 . . ? N4 C15 H15 125.0 . . ? N5 C16 N6 113.8(4) . . ? N5 C16 H16 123.1 . . ? N6 C16 H16 123.1 . . ? 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 O4 Zn1 O2 C7 179.1(3) 1_565 . . . ? N1 Zn1 O2 C7 -53.2(3) . . . . ? N6 Zn1 O2 C7 65.0(3) 2_776 . . . ? O4 Zn1 N1 C10 164.0(3) 1_565 . . . ? O2 Zn1 N1 C10 41.4(4) . . . . ? N6 Zn1 N1 C10 -73.9(4) 2_776 . . . ? O4 Zn1 N1 C11 -16.2(6) 1_565 . . . ? O2 Zn1 N1 C11 -138.7(5) . . . . ? N6 Zn1 N1 C11 106.0(5) 2_776 . . . ? C10 N2 N3 C11 0.8(6) . . . . ? C12 N2 N3 C11 -178.0(5) . . . . ? C15 N4 N5 C16 0.4(5) . . . . ? C14 N4 N5 C16 173.7(4) . . . . ? C6 C1 C2 C3 1.3(6) . . . . ? C7 C1 C2 C3 -178.2(3) . . . . ? C1 C2 C3 C4 -0.4(6) . . . . ? C1 C2 C3 C8 177.3(4) . . . . ? C2 C3 C4 C5 -0.6(6) . . . . ? C8 C3 C4 C5 -178.3(4) . . . . ? C9 O5 C5 C6 2.2(7) . . . . ? C9 O5 C5 C4 -177.9(5) . . . . ? C3 C4 C5 O5 -179.2(4) . . . . ? C3 C4 C5 C6 0.7(7) . . . . ? C2 C1 C6 C5 -1.2(6) . . . . ? C7 C1 C6 C5 178.3(4) . . . . ? O5 C5 C6 C1 -179.9(4) . . . . ? C4 C5 C6 C1 0.2(6) . . . . ? Zn1 O2 C7 O1 -5.8(5) . . . . ? Zn1 O2 C7 C1 175.4(3) . . . . ? C6 C1 C7 O1 -166.8(4) . . . . ? C2 C1 C7 O1 12.7(6) . . . . ? C6 C1 C7 O2 12.0(6) . . . . ? C2 C1 C7 O2 -168.5(4) . . . . ? Zn1 O4 C8 O3 -5.2(5) 1_545 . . . ? Zn1 O4 C8 C3 173.0(3) 1_545 . . . ? C4 C3 C8 O3 171.7(4) . . . . ? C2 C3 C8 O3 -6.0(6) . . . . ? C4 C3 C8 O4 -6.5(6) . . . . ? C2 C3 C8 O4 175.8(4) . . . . ? N3 N2 C10 N1 -1.0(6) . . . . ? C12 N2 C10 N1 177.7(4) . . . . ? C11 N1 C10 N2 0.8(6) . . . . ? Zn1 N1 C10 N2 -179.3(3) . . . . ? N2 N3 C11 N1 -0.3(8) . . . . ? C10 N1 C11 N3 -0.2(7) . . . . ? Zn1 N1 C11 N3 179.9(4) . . . . ? C10 N2 C12 C13 128.3(5) . . . . ? N3 N2 C12 C13 -53.0(6) . . . . ? N2 C12 C13 C14 -164.0(4) . . . . ? C15 N4 C14 C13 95.3(5) . . . . ? N5 N4 C14 C13 -76.7(5) . . . . ? C12 C13 C14 N4 75.4(5) . . . . ? C16 N6 C15 N4 -0.1(5) . . . . ? Zn1 N6 C15 N4 165.2(3) 2_776 . . . ? N5 N4 C15 N6 -0.2(5) . . . . ? C14 N4 C15 N6 -173.0(4) . . . . ? N4 N5 C16 N6 -0.4(5) . . . . ? C15 N6 C16 N5 0.3(5) . . . . ? Zn1 N6 C16 N5 -164.5(3) 2_776 . . . ? 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 O6 H1W O7 0.78 2.44 3.006(13) 129.9 . O6 H2W O3 0.85 2.01 2.855(7) 178.1 1_455 O7 H4W O1 0.83 1.97 2.743(7) 156.3 1_455 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.008 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.107 _database_code_depnum_ccdc_archive 'CCDC 960216' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H30 N6 O14 Zn2' _chemical_formula_weight 769.29 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.257(4) _cell_length_b 10.829(3) _cell_length_c 17.134(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.765(3) _cell_angle_gamma 90.00 _cell_volume 3134.6(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2591 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 25.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 1.608 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6109 _exptl_absorpt_correction_T_max 0.7717 _exptl_absorpt_process_details sadabs _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 cans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11549 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2914 _reflns_number_gt 2317 _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^)+(0.0473P)^2^+1.1470P] 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 2914 _refine_ls_number_parameters 224 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0858 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.040 _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 0.435424(18) 0.51108(3) 0.88446(2) 0.03550(14) Uani 1 1 d . . . O1 O 0.31288(12) 0.3479(2) 0.85153(14) 0.0516(6) Uani 1 1 d . . . O2 O 0.34668(12) 0.49674(17) 0.93982(13) 0.0416(5) Uani 1 1 d . . . O3 O 0.05682(13) 0.1253(2) 0.84272(14) 0.0549(6) Uani 1 1 d . . . O4 O -0.00033(11) 0.14394(18) 0.94544(12) 0.0408(5) Uani 1 1 d . . . O5 O 0.11349(14) 0.5289(2) 1.07932(16) 0.0638(7) Uani 1 1 d . . . O6 O 0.37898(13) 0.5875(2) 0.78322(13) 0.0630(7) Uani 1 1 d . . . H1W H 0.3322 0.6071 0.7872 0.094 Uiso 1 1 d R . . H2W H 0.3980 0.6054 0.7426 0.094 Uiso 1 1 d R . . O7 O 0.27366(13) 0.1634(2) 0.74229(15) 0.0667(7) Uani 1 1 d . . . H3W H 0.2859 0.2346 0.7618 0.100 Uiso 1 1 d R . . H4W H 0.2977 0.1693 0.7038 0.100 Uiso 1 1 d R . . N1 N 0.49996(13) 0.3628(2) 0.86541(14) 0.0356(6) Uani 1 1 d . . . N2 N 0.53438(15) 0.1768(2) 0.84030(15) 0.0411(6) Uani 1 1 d . . . N3 N 0.60347(15) 0.2419(3) 0.85812(18) 0.0560(7) Uani 1 1 d . . . C1 C 0.22504(15) 0.3944(2) 0.93792(16) 0.0315(6) Uani 1 1 d . . . C2 C 0.17435(15) 0.2986(2) 0.90900(16) 0.0320(6) Uani 1 1 d . . . H2 H 0.1863 0.2462 0.8701 0.038 Uiso 1 1 calc R . . C3 C 0.10582(15) 0.2804(2) 0.93772(16) 0.0314(6) Uani 1 1 d . . . C4 C 0.08763(16) 0.3585(3) 0.99524(17) 0.0355(7) Uani 1 1 d . . . H4 H 0.0418 0.3460 1.0148 0.043 Uiso 1 1 calc R . . C5 C 0.13816(18) 0.4558(3) 1.02381(18) 0.0403(7) Uani 1 1 d . . . C6 C 0.20731(17) 0.4733(3) 0.99595(19) 0.0367(7) Uani 1 1 d . . . H6A H 0.2416 0.5373 1.0159 0.044 Uiso 1 1 calc R . . C7 C 0.29970(16) 0.4126(3) 0.90669(18) 0.0360(7) Uani 1 1 d . . . C8 C 0.05110(17) 0.1762(3) 0.90587(18) 0.0373(7) Uani 1 1 d . . . C9 C 0.1634(2) 0.6287(4) 1.1127(3) 0.0878(15) Uani 1 1 d . . . H9A H 0.2134 0.5968 1.1404 0.132 Uiso 1 1 calc R . . H9B H 0.1387 0.6736 1.1493 0.132 Uiso 1 1 calc R . . H9C H 0.1717 0.6829 1.0708 0.132 Uiso 1 1 calc R . . C10 C 0.47452(17) 0.2497(3) 0.84476(16) 0.0366(7) Uani 1 1 d . . . H10 H 0.4218 0.2253 0.8348 0.044 Uiso 1 1 calc R . . C11 C 0.57919(19) 0.3518(3) 0.8729(2) 0.0574(10) Uani 1 1 d . . . H11 H 0.6137 0.4176 0.8874 0.069 Uiso 1 1 calc R . . C12 C 0.5340(2) 0.0435(3) 0.8231(2) 0.0562(9) Uani 1 1 d D . . H12A H 0.5859(8) 0.011(3) 0.843(2) 0.067 Uiso 1 1 d D . . H12B H 0.5095(17) 0.006(3) 0.8625(17) 0.067 Uiso 1 1 d D . . C13 C 0.4657(4) 0.0068(5) 0.7580(4) 0.0506(18) Uani 0.50 1 d PD . . H13A H 0.4444 -0.0737 0.7638 0.061 Uiso 0.50 1 d PRD . . H13B H 0.4236 0.0526 0.7734 0.061 Uiso 0.50 1 d PRD . . 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 0.0291(2) 0.0362(2) 0.0444(2) -0.00929(15) 0.01504(15) -0.00702(14) O1 0.0390(13) 0.0569(14) 0.0659(15) -0.0193(12) 0.0268(11) -0.0109(10) O2 0.0299(11) 0.0462(13) 0.0517(13) -0.0065(10) 0.0155(9) -0.0153(9) O3 0.0564(15) 0.0641(15) 0.0519(14) -0.0242(12) 0.0293(12) -0.0294(12) O4 0.0369(11) 0.0454(12) 0.0451(12) -0.0076(9) 0.0200(10) -0.0184(9) O5 0.0566(16) 0.0692(16) 0.0763(19) -0.0389(13) 0.0387(14) -0.0261(12) O6 0.0447(13) 0.097(2) 0.0533(15) 0.0228(14) 0.0243(11) 0.0090(13) O7 0.0519(15) 0.0742(17) 0.0778(18) -0.0222(14) 0.0225(13) -0.0160(13) N1 0.0303(13) 0.0403(14) 0.0378(14) -0.0028(11) 0.0111(11) -0.0019(11) N2 0.0433(15) 0.0407(15) 0.0407(14) 0.0027(11) 0.0119(12) 0.0078(12) N3 0.0373(15) 0.0521(18) 0.078(2) -0.0011(15) 0.0111(14) 0.0063(14) C1 0.0279(14) 0.0296(15) 0.0388(16) 0.0035(12) 0.0112(12) -0.0034(11) C2 0.0307(15) 0.0299(15) 0.0376(16) 0.0006(12) 0.0122(12) -0.0042(12) C3 0.0299(15) 0.0294(15) 0.0357(15) 0.0012(12) 0.0088(12) -0.0047(12) C4 0.0310(15) 0.0401(16) 0.0390(17) -0.0012(13) 0.0153(13) -0.0099(13) C5 0.0410(17) 0.0426(17) 0.0412(18) -0.0115(14) 0.0175(14) -0.0087(14) C6 0.0322(16) 0.0335(16) 0.0453(18) -0.0049(13) 0.0103(13) -0.0118(12) C7 0.0276(15) 0.0353(16) 0.0477(18) 0.0054(14) 0.0136(13) -0.0026(13) C8 0.0321(16) 0.0389(17) 0.0426(18) -0.0021(14) 0.0114(13) -0.0076(13) C9 0.087(3) 0.078(3) 0.111(4) -0.061(3) 0.050(3) -0.036(2) C10 0.0328(16) 0.0401(17) 0.0386(16) 0.0007(13) 0.0113(13) 0.0025(13) C11 0.0341(19) 0.053(2) 0.085(3) -0.0117(19) 0.0123(18) -0.0028(16) C12 0.067(3) 0.0378(19) 0.065(3) 0.0101(17) 0.016(2) 0.0179(18) C13 0.068(5) 0.028(3) 0.063(5) -0.005(3) 0.029(4) -0.008(3) _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 1.965(2) . ? Zn1 O4 1.9794(19) 3 ? Zn1 O6 1.988(2) . ? Zn1 N1 2.018(2) . ? O1 C7 1.234(3) . ? O2 C7 1.274(3) . ? O3 C8 1.236(4) . ? O4 C8 1.271(3) . ? O4 Zn1 1.9793(19) 3_445 ? O5 C5 1.371(4) . ? O5 C9 1.427(4) . ? O6 H1W 0.8501 . ? O6 H2W 0.8499 . ? O7 H3W 0.8500 . ? O7 H4W 0.8501 . ? N1 C10 1.325(3) . ? N1 C11 1.352(4) . ? N2 C10 1.315(4) . ? N2 N3 1.365(4) . ? N2 C12 1.473(4) . ? N3 C11 1.303(4) . ? C1 C2 1.382(4) . ? C1 C6 1.392(4) . ? C1 C7 1.506(4) . ? C2 C3 1.385(4) . ? C2 H2 0.9300 . ? C3 C4 1.383(4) . ? C3 C8 1.500(4) . ? C4 C5 1.391(4) . ? C4 H4 0.9300 . ? C5 C6 1.386(4) . ? C6 H6A 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.445(8) 2_656 ? C12 C13 1.501(8) . ? C12 H12A 0.957(10) . ? C12 H12B 0.958(10) . ? C13 C13 1.268(14) 2_656 ? C13 C12 1.445(8) 2_656 ? C13 H13A 0.9601 . ? C13 H13B 0.9600 . ? 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 O4 102.15(8) . 3 ? O2 Zn1 O6 99.36(9) . . ? O4 Zn1 O6 106.26(10) 3 . ? O2 Zn1 N1 121.69(9) . . ? O4 Zn1 N1 113.29(9) 3 . ? O6 Zn1 N1 112.23(10) . . ? C7 O2 Zn1 109.22(18) . . ? C8 O4 Zn1 107.18(18) . 3_445 ? C5 O5 C9 117.9(3) . . ? Zn1 O6 H1W 109.7 . . ? Zn1 O6 H2W 127.4 . . ? H1W O6 H2W 122.7 . . ? H3W O7 H4W 96.7 . . ? C10 N1 C11 102.5(3) . . ? C10 N1 Zn1 127.95(19) . . ? C11 N1 Zn1 129.5(2) . . ? C10 N2 N3 109.7(2) . . ? C10 N2 C12 128.9(3) . . ? N3 N2 C12 121.3(3) . . ? C11 N3 N2 102.4(3) . . ? C2 C1 C6 120.1(2) . . ? C2 C1 C7 119.7(2) . . ? C6 C1 C7 120.2(2) . . ? C1 C2 C3 120.2(3) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 120.0(2) . . ? C4 C3 C8 120.1(2) . . ? C2 C3 C8 119.8(2) . . ? C3 C4 C5 119.8(2) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? O5 C5 C6 124.8(3) . . ? O5 C5 C4 114.9(3) . . ? C6 C5 C4 120.3(3) . . ? C5 C6 C1 119.5(3) . . ? C5 C6 H6A 120.3 . . ? C1 C6 H6A 120.3 . . ? O1 C7 O2 123.2(3) . . ? O1 C7 C1 120.2(3) . . ? O2 C7 C1 116.6(3) . . ? O3 C8 O4 122.2(3) . . ? O3 C8 C3 119.8(3) . . ? O4 C8 C3 118.0(3) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 N1 110.4(3) . . ? N2 C10 H10 124.8 . . ? N1 C10 H10 124.8 . . ? N3 C11 N1 114.9(3) . . ? N3 C11 H11 122.5 . . ? N1 C11 H11 122.5 . . ? C13 C12 N2 117.4(4) 2_656 . ? C13 C12 C13 50.9(5) 2_656 . ? N2 C12 C13 112.3(3) . . ? C13 C12 H12A 93(2) 2_656 . ? N2 C12 H12A 109(2) . . ? C13 C12 H12A 134(2) . . ? C13 C12 H12B 130(2) 2_656 . ? N2 C12 H12B 105(2) . . ? C13 C12 H12B 91(2) . . ? H12A C12 H12B 96.5(13) . . ? C13 C13 C12 66.8(6) 2_656 2_656 ? C13 C13 C12 62.2(6) 2_656 . ? C12 C13 C12 119.0(5) 2_656 . ? C13 C13 H13A 114.6 2_656 . ? C12 C13 H13A 115.2 2_656 . ? C12 C13 H13A 115.0 . . ? C13 C13 H13B 148.4 2_656 . ? C12 C13 H13B 105.9 2_656 . ? C12 C13 H13B 100.6 . . ? H13A C13 H13B 96.5 . . ? 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 O4 Zn1 O2 C7 -179.68(18) 3 . . . ? O6 Zn1 O2 C7 71.3(2) . . . . ? N1 Zn1 O2 C7 -52.2(2) . . . . ? O2 Zn1 N1 C10 39.8(3) . . . . ? O4 Zn1 N1 C10 162.1(2) 3 . . . ? O6 Zn1 N1 C10 -77.5(3) . . . . ? O2 Zn1 N1 C11 -137.7(3) . . . . ? O4 Zn1 N1 C11 -15.3(3) 3 . . . ? O6 Zn1 N1 C11 105.0(3) . . . . ? C10 N2 N3 C11 0.4(3) . . . . ? C12 N2 N3 C11 -177.1(3) . . . . ? C6 C1 C2 C3 -0.2(4) . . . . ? C7 C1 C2 C3 179.5(2) . . . . ? C1 C2 C3 C4 0.3(4) . . . . ? C1 C2 C3 C8 179.9(3) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C8 C3 C4 C5 -179.2(3) . . . . ? C9 O5 C5 C6 -1.7(5) . . . . ? C9 O5 C5 C4 178.5(3) . . . . ? C3 C4 C5 O5 178.6(3) . . . . ? C3 C4 C5 C6 -1.2(5) . . . . ? O5 C5 C6 C1 -178.4(3) . . . . ? C4 C5 C6 C1 1.4(5) . . . . ? C2 C1 C6 C5 -0.7(4) . . . . ? C7 C1 C6 C5 179.7(3) . . . . ? Zn1 O2 C7 O1 3.8(4) . . . . ? Zn1 O2 C7 C1 -176.02(19) . . . . ? C2 C1 C7 O1 5.2(4) . . . . ? C6 C1 C7 O1 -175.2(3) . . . . ? C2 C1 C7 O2 -175.0(3) . . . . ? C6 C1 C7 O2 4.6(4) . . . . ? Zn1 O4 C8 O3 -2.2(4) 3_445 . . . ? Zn1 O4 C8 C3 177.5(2) 3_445 . . . ? C4 C3 C8 O3 163.0(3) . . . . ? C2 C3 C8 O3 -16.6(4) . . . . ? C4 C3 C8 O4 -16.7(4) . . . . ? C2 C3 C8 O4 163.8(3) . . . . ? N3 N2 C10 N1 -0.3(3) . . . . ? C12 N2 C10 N1 177.0(3) . . . . ? C11 N1 C10 N2 0.0(3) . . . . ? Zn1 N1 C10 N2 -178.00(19) . . . . ? N2 N3 C11 N1 -0.5(4) . . . . ? C10 N1 C11 N3 0.3(4) . . . . ? Zn1 N1 C11 N3 178.3(2) . . . . ? C10 N2 C12 C13 97.3(5) . . . 2_656 ? N3 N2 C12 C13 -85.7(5) . . . 2_656 ? C10 N2 C12 C13 41.0(5) . . . . ? N3 N2 C12 C13 -142.0(4) . . . . ? N2 C12 C13 C13 108.0(3) . . . 2_656 ? C13 C12 C13 C12 -36.8(6) 2_656 . . 2_656 ? N2 C12 C13 C12 71.2(5) . . . 2_656 ? 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 O7 H4W N3 0.85 2.32 3.109(4) 154.1 2_656 O7 H3W O1 0.85 1.95 2.727(3) 152.0 . O6 H2W O3 0.85 1.80 2.651(3) 173.3 4_556 O6 H1W O7 0.85 1.89 2.708(3) 159.7 4_556 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.425 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 960217' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_bb _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H30 N6 O14 Zn2' _chemical_formula_weight 769.29 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.004(5) _cell_length_b 9.661(3) _cell_length_c 19.023(5) _cell_angle_alpha 90.00 _cell_angle_beta 112.238(3) _cell_angle_gamma 90.00 _cell_volume 3062.6(14) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3847 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 25.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.668 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 1.646 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6838 _exptl_absorpt_correction_T_max 0.7561 _exptl_absorpt_process_details SADABS _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 10682 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2751 _reflns_number_gt 2291 _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^)+(0.0379P)^2^+3.6292P] 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 2751 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0774 _refine_ls_wR_factor_gt 0.0714 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.950 _refine_ls_shift/su_max 0.003 _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 0.720412(16) -0.04501(3) 1.026016(16) 0.02958(11) Uani 1 1 d . . . O1 O 0.83861(10) -0.05856(17) 1.06825(11) 0.0348(4) Uani 1 1 d . . . O2 O 0.82515(10) 0.14230(18) 1.00945(11) 0.0380(4) Uani 1 1 d . . . O3 O 1.06997(11) 0.3620(2) 0.99357(11) 0.0452(5) Uani 1 1 d . . . O4 O 1.18963(9) 0.29356(19) 1.07175(10) 0.0352(4) Uani 1 1 d . . . O5 O 1.13035(11) -0.1216(2) 1.20914(12) 0.0515(6) Uani 1 1 d . . . O6 O 0.69368(11) 0.12237(19) 1.07382(11) 0.0388(4) Uani 1 1 d . . . H1W H 0.6784 0.1847 1.0424 0.058 Uiso 1 1 d R . . H2W H 0.6500 0.1011 1.0901 0.058 Uiso 1 1 d R . . O7 O 0.57489(12) 0.0947(2) 0.12134(11) 0.0507(5) Uani 1 1 d . . . H3W H 0.5785 0.1236 0.1685 0.076 Uiso 1 1 d R . . H4W H 0.5314 0.1192 0.0864 0.076 Uiso 1 1 d R . . N1 N 0.67114(13) -0.0278(2) 0.91220(12) 0.0320(5) Uani 1 1 d . . . N2 N 0.60534(14) 0.0622(2) 0.80171(12) 0.0370(5) Uani 1 1 d . . . N3 N 0.60124(16) -0.0772(2) 0.79034(14) 0.0449(6) Uani 1 1 d . . . C1 C 0.95759(14) 0.0567(2) 1.07578(14) 0.0258(5) Uani 1 1 d . . . C2 C 0.99288(14) 0.1613(2) 1.04860(13) 0.0256(5) Uani 1 1 d . . . H2 H 0.9609 0.2250 1.0136 0.031 Uiso 1 1 calc R . . C3 C 1.07583(14) 0.1701(2) 1.07385(13) 0.0259(5) Uani 1 1 d . . . C4 C 1.12459(14) 0.0764(2) 1.12722(14) 0.0282(5) Uani 1 1 d . . . H4 H 1.1802 0.0825 1.1440 0.034 Uiso 1 1 calc R . . C5 C 1.08879(15) -0.0264(2) 1.15505(15) 0.0312(6) Uani 1 1 d . . . C6 C 1.00581(15) -0.0373(2) 1.12880(15) 0.0309(6) Uani 1 1 d . . . H6A H 0.9824 -0.1077 1.1467 0.037 Uiso 1 1 calc R . . C7 C 0.86813(14) 0.0484(2) 1.04839(14) 0.0261(5) Uani 1 1 d . . . C8 C 1.11264(14) 0.2835(3) 1.04312(14) 0.0287(5) Uani 1 1 d . . . C9 C 1.21435(19) -0.1133(4) 1.2405(2) 0.0713(12) Uani 1 1 d . . . H9A H 1.2348 -0.1221 1.2009 0.107 Uiso 1 1 calc R . . H9B H 1.2354 -0.1866 1.2767 0.107 Uiso 1 1 calc R . . H9C H 1.2303 -0.0256 1.2654 0.107 Uiso 1 1 calc R . . C10 C 0.64107(16) -0.1259(3) 0.85837(16) 0.0404(6) Uani 1 1 d . . . H10 H 0.6481 -0.2201 0.8688 0.049 Uiso 1 1 calc R . . C11 C 0.64713(17) 0.0890(3) 0.87387(15) 0.0378(6) Uani 1 1 d . . . H11 H 0.6582 0.1772 0.8949 0.045 Uiso 1 1 calc R . . C12 C 0.5659(2) 0.1584(3) 0.73897(16) 0.0493(8) Uani 1 1 d . . . H12A H 0.5436 0.1065 0.6920 0.059 Uiso 1 1 calc R . . H12B H 0.6057 0.2217 0.7344 0.059 Uiso 1 1 calc R . . C13 C 0.5000 0.2408(4) 0.7500 0.0474(11) Uani 1 2 d S . . H13A H 0.5241 0.3002 0.7939 0.057 Uiso 0.50 1 calc PR . . H13B H 0.4759 0.3002 0.7061 0.057 Uiso 0.50 1 calc PR . . 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 0.02271(16) 0.03053(17) 0.03414(19) 0.00970(12) 0.00922(12) -0.00190(12) O1 0.0230(9) 0.0305(9) 0.0514(11) 0.0111(8) 0.0146(8) -0.0043(7) O2 0.0262(9) 0.0289(10) 0.0576(12) 0.0125(9) 0.0143(8) 0.0004(7) O3 0.0312(10) 0.0466(12) 0.0551(13) 0.0215(10) 0.0133(9) -0.0041(9) O4 0.0234(9) 0.0370(10) 0.0430(11) 0.0087(8) 0.0102(8) -0.0089(7) O5 0.0327(10) 0.0512(13) 0.0640(14) 0.0303(11) 0.0107(10) 0.0026(9) O6 0.0396(10) 0.0318(10) 0.0502(12) 0.0086(8) 0.0228(9) 0.0015(8) O7 0.0444(12) 0.0730(15) 0.0363(12) 0.0077(10) 0.0170(9) 0.0075(11) N1 0.0318(11) 0.0299(12) 0.0341(12) 0.0055(9) 0.0121(9) -0.0018(9) N2 0.0485(14) 0.0335(12) 0.0281(12) 0.0030(9) 0.0135(10) -0.0026(10) N3 0.0555(16) 0.0351(13) 0.0376(14) -0.0051(10) 0.0103(12) -0.0031(11) C1 0.0269(12) 0.0228(11) 0.0301(13) -0.0031(10) 0.0134(10) -0.0039(9) C2 0.0257(12) 0.0237(12) 0.0276(13) 0.0010(9) 0.0104(10) -0.0023(9) C3 0.0275(12) 0.0246(12) 0.0283(13) -0.0047(10) 0.0136(10) -0.0062(9) C4 0.0202(11) 0.0300(13) 0.0333(14) 0.0016(10) 0.0089(10) -0.0043(9) C5 0.0313(13) 0.0279(13) 0.0345(14) 0.0042(10) 0.0125(11) -0.0003(10) C6 0.0309(13) 0.0255(12) 0.0386(15) 0.0035(11) 0.0158(11) -0.0055(10) C7 0.0256(12) 0.0218(11) 0.0334(14) -0.0014(10) 0.0140(10) -0.0056(10) C8 0.0285(13) 0.0281(12) 0.0315(14) 0.0017(11) 0.0135(11) -0.0052(10) C9 0.0372(17) 0.079(3) 0.079(3) 0.041(2) 0.0007(17) 0.0003(17) C10 0.0424(15) 0.0306(14) 0.0445(17) 0.0035(12) 0.0122(13) 0.0008(12) C11 0.0500(17) 0.0288(14) 0.0333(16) 0.0007(11) 0.0142(13) -0.0040(12) C12 0.067(2) 0.0445(17) 0.0298(16) 0.0097(13) 0.0107(14) -0.0044(15) C13 0.068(3) 0.028(2) 0.027(2) 0.000 -0.0032(19) 0.000 _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 O4 1.9649(17) 3_445 ? Zn1 O1 1.9740(18) . ? Zn1 O6 2.0012(19) . ? Zn1 N1 2.012(2) . ? O1 C7 1.282(3) . ? O2 C7 1.240(3) . ? O3 C8 1.227(3) . ? O4 C8 1.287(3) . ? O4 Zn1 1.9649(17) 3 ? O5 C5 1.372(3) . ? O5 C9 1.402(4) . ? O6 H1W 0.8200 . ? O6 H2W 0.9696 . ? O7 H3W 0.9181 . ? O7 H4W 0.8463 . ? N1 C11 1.324(3) . ? N1 C10 1.350(4) . ? N2 C11 1.317(3) . ? N2 N3 1.362(3) . ? N2 C12 1.466(3) . ? N3 C10 1.307(4) . ? C1 C6 1.390(3) . ? C1 C2 1.393(3) . ? C1 C7 1.496(3) . ? C2 C3 1.388(3) . ? C2 H2 0.9300 . ? C3 C4 1.395(3) . ? C3 C8 1.508(3) . ? C4 C5 1.393(3) . ? C4 H4 0.9300 . ? C5 C6 1.388(4) . ? C6 H6A 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.508(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C12 1.508(4) 2_656 ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? 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 O4 Zn1 O1 102.03(7) 3_445 . ? O4 Zn1 O6 106.46(8) 3_445 . ? O1 Zn1 O6 106.04(8) . . ? O4 Zn1 N1 117.31(8) 3_445 . ? O1 Zn1 N1 114.32(8) . . ? O6 Zn1 N1 109.76(8) . . ? C7 O1 Zn1 109.26(15) . . ? C8 O4 Zn1 108.15(15) . 3 ? C5 O5 C9 118.4(2) . . ? Zn1 O6 H1W 109.5 . . ? Zn1 O6 H2W 109.7 . . ? H1W O6 H2W 107.5 . . ? H3W O7 H4W 112.6 . . ? C11 N1 C10 103.1(2) . . ? C11 N1 Zn1 125.62(18) . . ? C10 N1 Zn1 130.19(18) . . ? C11 N2 N3 109.6(2) . . ? C11 N2 C12 129.3(2) . . ? N3 N2 C12 121.1(2) . . ? C10 N3 N2 102.8(2) . . ? C6 C1 C2 119.7(2) . . ? C6 C1 C7 120.8(2) . . ? C2 C1 C7 119.5(2) . . ? C3 C2 C1 119.9(2) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.7(2) . . ? C2 C3 C8 118.9(2) . . ? C4 C3 C8 120.4(2) . . ? C5 C4 C3 119.0(2) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? O5 C5 C6 115.2(2) . . ? O5 C5 C4 124.3(2) . . ? C6 C5 C4 120.5(2) . . ? C5 C6 C1 120.2(2) . . ? C5 C6 H6A 119.9 . . ? C1 C6 H6A 119.9 . . ? O2 C7 O1 122.1(2) . . ? O2 C7 C1 121.0(2) . . ? O1 C7 C1 116.9(2) . . ? O3 C8 O4 122.7(2) . . ? O3 C8 C3 120.5(2) . . ? O4 C8 C3 116.9(2) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 N1 114.3(3) . . ? N3 C10 H10 122.9 . . ? N1 C10 H10 122.9 . . ? N2 C11 N1 110.2(2) . . ? N2 C11 H11 124.9 . . ? N1 C11 H11 124.9 . . ? N2 C12 C13 112.6(2) . . ? N2 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? N2 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C12 C13 C12 116.3(3) 2_656 . ? C12 C13 H13A 108.2 2_656 . ? C12 C13 H13A 108.2 . . ? C12 C13 H13B 108.2 2_656 . ? C12 C13 H13B 108.2 . . ? H13A C13 H13B 107.4 . . ? 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 O4 Zn1 O1 C7 -174.37(16) 3_445 . . . ? O6 Zn1 O1 C7 -63.10(17) . . . . ? N1 Zn1 O1 C7 57.96(18) . . . . ? O4 Zn1 N1 C11 141.5(2) 3_445 . . . ? O1 Zn1 N1 C11 -99.2(2) . . . . ? O6 Zn1 N1 C11 19.8(2) . . . . ? O4 Zn1 N1 C10 -24.6(3) 3_445 . . . ? O1 Zn1 N1 C10 94.8(2) . . . . ? O6 Zn1 N1 C10 -146.3(2) . . . . ? C11 N2 N3 C10 0.7(3) . . . . ? C12 N2 N3 C10 -178.6(3) . . . . ? C6 C1 C2 C3 0.7(3) . . . . ? C7 C1 C2 C3 179.8(2) . . . . ? C1 C2 C3 C4 -0.9(3) . . . . ? C1 C2 C3 C8 179.5(2) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? C8 C3 C4 C5 179.4(2) . . . . ? C9 O5 C5 C6 -177.4(3) . . . . ? C9 O5 C5 C4 2.0(4) . . . . ? C3 C4 C5 O5 -178.0(2) . . . . ? C3 C4 C5 C6 1.4(4) . . . . ? O5 C5 C6 C1 177.9(2) . . . . ? C4 C5 C6 C1 -1.6(4) . . . . ? C2 C1 C6 C5 0.6(4) . . . . ? C7 C1 C6 C5 -178.5(2) . . . . ? Zn1 O1 C7 O2 0.9(3) . . . . ? Zn1 O1 C7 C1 179.61(16) . . . . ? C6 C1 C7 O2 170.0(2) . . . . ? C2 C1 C7 O2 -9.1(4) . . . . ? C6 C1 C7 O1 -8.8(3) . . . . ? C2 C1 C7 O1 172.2(2) . . . . ? Zn1 O4 C8 O3 2.7(3) 3 . . . ? Zn1 O4 C8 C3 -176.73(16) 3 . . . ? C2 C3 C8 O3 -3.9(4) . . . . ? C4 C3 C8 O3 176.6(2) . . . . ? C2 C3 C8 O4 175.5(2) . . . . ? C4 C3 C8 O4 -4.0(3) . . . . ? N2 N3 C10 N1 -0.8(3) . . . . ? C11 N1 C10 N3 0.5(3) . . . . ? Zn1 N1 C10 N3 168.92(19) . . . . ? N3 N2 C11 N1 -0.5(3) . . . . ? C12 N2 C11 N1 178.7(3) . . . . ? C10 N1 C11 N2 0.0(3) . . . . ? Zn1 N1 C11 N2 -169.12(17) . . . . ? C11 N2 C12 C13 -63.1(4) . . . . ? N3 N2 C12 C13 116.0(3) . . . . ? N2 C12 C13 C12 -56.68(19) . . . 2_656 ? 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 O7 H4W O3 0.85 1.89 2.728(3) 169.2 7_656 O7 H3W O5 0.92 2.64 3.168(3) 117.1 3_454 O7 H3W N3 0.92 2.24 3.072(3) 150.2 6 O6 H2W O7 0.97 1.67 2.632(3) 169.8 1_556 O6 H1W O2 0.82 1.93 2.718(3) 161.2 7_657 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.613 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.059 _database_code_depnum_ccdc_archive 'CCDC 960218'