# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 ####################################################################### # # 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_k07adb7 _database_code_depnum_ccdc_archive 'CCDC 781644' #TrackingRef 'c0ce00310g.cif' _database_code_depnum_ccdc_archive 'CCDC 781644' #TrackingRef '- burrows-dpp.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H29 N8 O6 Zn1.50' _chemical_formula_weight 719.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 18.8940(2) _cell_length_b 9.3870(1) _cell_length_c 36.7670(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.624(1) _cell_angle_gamma 90.00 _cell_volume 6387.18(12) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 38172 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description Tabloid _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2960 _exptl_absorpt_coefficient_mu 1.193 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.85 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37375 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -47 _diffrn_reflns_limit_l_max 47 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7247 _reflns_number_gt 6168 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97/2 (Sheldrick 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick 1997)' _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^)+(0.0300P)^2^+10.8747P] 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 7247 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0762 _refine_ls_wR_factor_gt 0.0706 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.5000 -0.39088(3) -0.2500 0.01871(7) Uani 1 2 d S . . Zn2 Zn 0.302368(11) 0.58979(2) 0.028122(6) 0.02090(6) Uani 1 1 d . . . O1 O 0.53216(7) -0.55098(14) -0.20458(4) 0.0270(3) Uani 1 1 d . . . O2 O 0.61126(7) -0.43705(14) -0.22954(4) 0.0281(3) Uani 1 1 d . . . O3 O 0.30557(7) 0.38935(15) 0.06306(4) 0.0329(3) Uani 1 1 d . . . O4 O 0.39758(7) 0.53323(13) 0.07037(4) 0.0249(3) Uani 1 1 d . . . O5 O 0.20267(7) 0.53562(14) -0.00012(4) 0.0281(3) Uani 1 1 d . . . O6 O 0.13953(7) 0.73380(14) -0.01794(4) 0.0280(3) Uani 1 1 d . . . N1 N 0.48185(8) -0.23797(15) -0.21169(4) 0.0201(3) Uani 1 1 d . . . N2 N 0.52097(8) 0.17705(16) -0.12339(4) 0.0216(3) Uani 1 1 d . . . N3 N 0.50167(8) 0.26618(15) -0.09858(4) 0.0202(3) Uani 1 1 d . . . H3 H 0.5290 0.3368 -0.0880 0.030(6) Uiso 1 1 calc R . . N4 N 0.34433(8) 0.47599(16) -0.01342(4) 0.0209(3) Uani 1 1 d . . . N5 N 0.25751(8) 0.70778(16) 0.06882(4) 0.0221(3) Uani 1 1 d . . . N6 N 0.09656(8) 0.96469(16) 0.14377(4) 0.0219(3) Uani 1 1 d . . . N7 N 0.08755(8) 1.06315(15) 0.16910(4) 0.0204(3) Uani 1 1 d . . . H71 H 0.0461 1.0787 0.1758 0.038(6) Uiso 1 1 calc R . . N8 N 0.16402(9) 1.46156(18) 0.26622(5) 0.0310(4) Uani 1 1 d . . . C1 C 0.59710(10) -0.52462(19) -0.20591(5) 0.0235(4) Uani 1 1 d . . . C2 C 0.65724(13) -0.5973(3) -0.17963(7) 0.0431(6) Uani 1 1 d . . . H2A H 0.6850 -0.6563 -0.1937 0.065 Uiso 1 1 calc R . . H2B H 0.6370 -0.6577 -0.1625 0.065 Uiso 1 1 calc R . . H2C H 0.6890 -0.5255 -0.1655 0.065 Uiso 1 1 calc R . . C3 C 0.36812(10) 0.42030(19) 0.07919(5) 0.0235(4) Uani 1 1 d . . . C4 C 0.40952(14) 0.3257(3) 0.10885(7) 0.0488(6) Uani 1 1 d . . . H4A H 0.4573 0.3669 0.1183 0.073 Uiso 0.50 1 calc PR . . H4B H 0.4150 0.2312 0.0984 0.073 Uiso 0.50 1 calc PR . . H4C H 0.3833 0.3172 0.1292 0.073 Uiso 0.50 1 calc PR . . H4D H 0.3797 0.2433 0.1123 0.073 Uiso 0.50 1 calc PR . . H4E H 0.4221 0.3790 0.1322 0.073 Uiso 0.50 1 calc PR . . H4F H 0.4538 0.2930 0.1014 0.073 Uiso 0.50 1 calc PR . . C5 C 0.14618(10) 0.6016(2) -0.01413(5) 0.0232(4) Uani 1 1 d . . . C6 C 0.07973(12) 0.5113(3) -0.02766(7) 0.0428(6) Uani 1 1 d . . . H6A H 0.0758 0.4899 -0.0541 0.064 Uiso 1 1 calc R . . H6B H 0.0367 0.5635 -0.0242 0.064 Uiso 1 1 calc R . . H6C H 0.0837 0.4223 -0.0135 0.064 Uiso 1 1 calc R . . C7 C 0.53798(10) -0.15310(19) -0.19737(5) 0.0214(4) Uani 1 1 d . . . H7 H 0.5824 -0.1666 -0.2053 0.026 Uiso 1 1 calc R . . C8 C 0.53413(10) -0.04806(19) -0.17194(5) 0.0203(4) Uani 1 1 d . . . H8 H 0.5752 0.0095 -0.1627 0.024 Uiso 1 1 calc R . . C9 C 0.46950(9) -0.02594(18) -0.15971(5) 0.0185(3) Uani 1 1 d . . . C10 C 0.41126(10) -0.11298(19) -0.17470(5) 0.0219(4) Uani 1 1 d . . . H10 H 0.3662 -0.1015 -0.1674 0.026 Uiso 1 1 calc R . . C11 C 0.41960(10) -0.21643(19) -0.20035(5) 0.0216(4) Uani 1 1 d . . . H11 H 0.3793 -0.2748 -0.2104 0.026 Uiso 1 1 calc R . . C12 C 0.46514(9) 0.08652(18) -0.13251(5) 0.0189(3) Uani 1 1 d . . . C13 C 0.41010(9) 0.11924(18) -0.11319(5) 0.0193(3) Uani 1 1 d . . . H13 H 0.3652 0.0716 -0.1147 0.023 Uiso 1 1 calc R . . C14 C 0.43553(9) 0.23599(18) -0.09143(5) 0.0185(3) Uani 1 1 d . . . C15 C 0.40436(9) 0.31889(18) -0.06473(5) 0.0189(3) Uani 1 1 d . . . C16 C 0.43843(10) 0.44048(19) -0.04756(5) 0.0235(4) Uani 1 1 d . . . H16 H 0.4829 0.4721 -0.0531 0.028 Uiso 1 1 calc R . . C17 C 0.40693(10) 0.5141(2) -0.02253(5) 0.0239(4) Uani 1 1 d . . . H17 H 0.4309 0.5964 -0.0111 0.029 Uiso 1 1 calc R . . C18 C 0.33893(10) 0.27945(19) -0.05559(5) 0.0241(4) Uani 1 1 d . . . H18 H 0.3136 0.1980 -0.0667 0.029 Uiso 1 1 calc R . . C19 C 0.31128(10) 0.3597(2) -0.03025(5) 0.0248(4) Uani 1 1 d . . . H19 H 0.2666 0.3313 -0.0244 0.030 Uiso 1 1 calc R . . C20 C 0.29530(10) 0.8132(2) 0.08814(5) 0.0258(4) Uani 1 1 d . . . H20 H 0.3437 0.8280 0.0853 0.031 Uiso 1 1 calc R . . C21 C 0.26777(10) 0.9015(2) 0.11196(5) 0.0251(4) Uani 1 1 d . . . H21 H 0.2968 0.9754 0.1248 0.030 Uiso 1 1 calc R . . C22 C 0.19751(10) 0.88184(19) 0.11701(5) 0.0204(4) Uani 1 1 d . . . C23 C 0.15848(10) 0.7696(2) 0.09771(5) 0.0236(4) Uani 1 1 d . . . H23 H 0.1106 0.7502 0.1007 0.028 Uiso 1 1 calc R . . C24 C 0.18996(10) 0.6867(2) 0.07429(5) 0.0239(4) Uani 1 1 d . . . H24 H 0.1625 0.6109 0.0613 0.029 Uiso 1 1 calc R . . C25 C 0.16666(9) 0.97554(19) 0.14181(5) 0.0200(4) Uani 1 1 d . . . C26 C 0.20133(10) 1.08120(19) 0.16582(5) 0.0215(4) Uani 1 1 d . . . H26 H 0.2506 1.1093 0.1694 0.026 Uiso 1 1 calc R . . C27 C 0.14922(9) 1.13599(18) 0.18318(5) 0.0194(3) Uani 1 1 d . . . C28 C 0.15340(10) 1.24707(18) 0.21148(5) 0.0201(4) Uani 1 1 d . . . C29 C 0.21716(10) 1.3230(2) 0.22346(5) 0.0287(4) Uani 1 1 d . . . H29 H 0.2586 1.3034 0.2133 0.034 Uiso 1 1 calc R . . C30 C 0.21967(11) 1.4277(2) 0.25034(6) 0.0321(5) Uani 1 1 d . . . H30 H 0.2636 1.4785 0.2580 0.039 Uiso 1 1 calc R . . C31 C 0.09498(10) 1.28165(19) 0.22783(5) 0.0232(4) Uani 1 1 d . . . H31 H 0.0501 1.2334 0.2207 0.028 Uiso 1 1 calc R . . C32 C 0.10346(11) 1.3868(2) 0.25449(5) 0.0280(4) Uani 1 1 d . . . H32 H 0.0631 1.4079 0.2654 0.034 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 0.02211(15) 0.01721(14) 0.01790(14) 0.000 0.00659(11) 0.000 Zn2 0.02038(12) 0.02349(11) 0.01996(11) -0.00302(8) 0.00678(8) 0.00231(8) O1 0.0246(7) 0.0272(7) 0.0322(7) -0.0019(6) 0.0126(6) -0.0021(6) O2 0.0236(7) 0.0283(7) 0.0342(7) 0.0058(6) 0.0102(6) 0.0010(6) O3 0.0243(7) 0.0360(8) 0.0377(8) 0.0009(6) 0.0045(6) -0.0097(6) O4 0.0233(7) 0.0229(6) 0.0291(7) -0.0026(5) 0.0071(5) -0.0060(5) O5 0.0232(7) 0.0298(7) 0.0308(7) -0.0066(6) 0.0043(6) 0.0031(6) O6 0.0322(7) 0.0243(7) 0.0307(7) -0.0014(6) 0.0140(6) 0.0003(6) N1 0.0252(8) 0.0182(7) 0.0181(7) -0.0002(6) 0.0073(6) 0.0003(6) N2 0.0222(8) 0.0212(7) 0.0224(7) -0.0048(6) 0.0073(6) 0.0003(6) N3 0.0191(7) 0.0205(7) 0.0218(7) -0.0066(6) 0.0063(6) -0.0025(6) N4 0.0202(8) 0.0230(8) 0.0206(7) -0.0038(6) 0.0066(6) 0.0001(6) N5 0.0221(8) 0.0244(8) 0.0209(7) -0.0023(6) 0.0071(6) 0.0033(6) N6 0.0235(8) 0.0233(8) 0.0206(7) -0.0039(6) 0.0081(6) 0.0008(6) N7 0.0201(8) 0.0224(7) 0.0206(7) -0.0027(6) 0.0087(6) 0.0013(6) N8 0.0283(9) 0.0314(9) 0.0336(9) -0.0113(7) 0.0067(7) -0.0008(7) C1 0.0237(10) 0.0228(9) 0.0246(9) -0.0024(7) 0.0059(7) 0.0017(7) C2 0.0365(13) 0.0446(13) 0.0441(13) 0.0103(11) -0.0017(10) 0.0076(10) C3 0.0229(9) 0.0237(9) 0.0245(9) -0.0021(7) 0.0063(7) -0.0024(7) C4 0.0510(15) 0.0440(14) 0.0458(14) 0.0141(11) -0.0034(11) 0.0008(11) C5 0.0234(9) 0.0273(9) 0.0213(8) -0.0030(7) 0.0100(7) -0.0019(8) C6 0.0304(12) 0.0395(12) 0.0550(14) 0.0048(11) 0.0007(10) -0.0104(10) C7 0.0225(9) 0.0206(8) 0.0231(9) 0.0006(7) 0.0096(7) 0.0013(7) C8 0.0205(9) 0.0205(8) 0.0203(8) 0.0000(7) 0.0052(7) -0.0008(7) C9 0.0224(9) 0.0171(8) 0.0166(8) 0.0019(6) 0.0052(7) 0.0017(7) C10 0.0214(9) 0.0226(9) 0.0234(9) -0.0014(7) 0.0088(7) -0.0017(7) C11 0.0234(9) 0.0212(9) 0.0214(8) -0.0008(7) 0.0074(7) -0.0033(7) C12 0.0201(9) 0.0180(8) 0.0185(8) -0.0012(7) 0.0035(7) 0.0001(7) C13 0.0188(9) 0.0200(8) 0.0197(8) -0.0017(7) 0.0050(7) -0.0020(7) C14 0.0173(8) 0.0192(8) 0.0197(8) 0.0001(7) 0.0050(7) 0.0004(7) C15 0.0196(9) 0.0202(8) 0.0172(8) 0.0005(7) 0.0045(7) 0.0003(7) C16 0.0204(9) 0.0250(9) 0.0273(9) -0.0057(7) 0.0100(7) -0.0052(7) C17 0.0220(9) 0.0256(9) 0.0251(9) -0.0081(7) 0.0072(7) -0.0049(7) C18 0.0230(9) 0.0223(9) 0.0284(9) -0.0062(7) 0.0087(7) -0.0056(7) C19 0.0232(9) 0.0249(9) 0.0290(9) -0.0042(8) 0.0115(8) -0.0040(7) C20 0.0198(9) 0.0344(10) 0.0240(9) -0.0057(8) 0.0062(7) 0.0010(8) C21 0.0210(9) 0.0305(10) 0.0236(9) -0.0080(8) 0.0037(7) -0.0013(8) C22 0.0223(9) 0.0234(9) 0.0161(8) 0.0005(7) 0.0051(7) 0.0043(7) C23 0.0212(9) 0.0283(9) 0.0233(9) -0.0016(7) 0.0092(7) -0.0004(7) C24 0.0258(10) 0.0247(9) 0.0224(9) -0.0034(7) 0.0078(7) -0.0031(7) C25 0.0210(9) 0.0226(9) 0.0172(8) 0.0015(7) 0.0057(7) 0.0032(7) C26 0.0186(9) 0.0260(9) 0.0204(8) -0.0015(7) 0.0053(7) 0.0022(7) C27 0.0194(9) 0.0213(8) 0.0177(8) 0.0008(7) 0.0043(7) 0.0014(7) C28 0.0225(9) 0.0203(8) 0.0174(8) 0.0003(7) 0.0042(7) 0.0026(7) C29 0.0216(10) 0.0348(11) 0.0314(10) -0.0085(8) 0.0091(8) -0.0009(8) C30 0.0230(10) 0.0375(11) 0.0361(11) -0.0119(9) 0.0067(8) -0.0048(8) C31 0.0207(9) 0.0238(9) 0.0265(9) -0.0039(7) 0.0083(7) -0.0022(7) C32 0.0246(10) 0.0310(10) 0.0305(10) -0.0068(8) 0.0110(8) 0.0008(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N1 2.0874(14) . ? Zn1 N1 2.0874(14) 2_654 ? Zn1 O2 2.1296(13) . ? Zn1 O2 2.1296(13) 2_654 ? Zn1 O1 2.2378(14) . ? Zn1 O1 2.2378(14) 2_654 ? Zn1 C1 2.5241(19) 2_654 ? Zn1 C1 2.5241(18) . ? Zn2 O5 2.0241(13) . ? Zn2 O6 2.0624(13) 7_565 ? Zn2 N4 2.1427(14) . ? Zn2 N5 2.1669(14) . ? Zn2 O4 2.1919(13) . ? Zn2 O3 2.2722(14) . ? Zn2 C3 2.5806(19) . ? O1 C1 1.262(2) . ? O2 C1 1.263(2) . ? O3 C3 1.245(2) . ? O4 C3 1.269(2) . ? O5 C5 1.251(2) . ? O6 C5 1.253(2) . ? O6 Zn2 2.0624(13) 7_565 ? N1 C11 1.340(2) . ? N1 C7 1.346(2) . ? N2 N3 1.3414(19) . ? N2 C12 1.343(2) . ? N3 C14 1.358(2) . ? N3 H3 0.8800 . ? N4 C17 1.341(2) . ? N4 C19 1.345(2) . ? N5 C20 1.337(2) . ? N5 C24 1.346(2) . ? N6 C25 1.345(2) . ? N6 N7 1.347(2) . ? N7 C27 1.360(2) . ? N7 H71 0.8800 . ? N8 C32 1.337(3) . ? N8 C30 1.340(3) . ? C1 C2 1.500(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.498(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C4 H4D 0.9800 . ? C4 H4E 0.9800 . ? C4 H4F 0.9800 . ? C5 C6 1.513(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.371(2) . ? C7 H7 0.9500 . ? C8 C9 1.399(2) . ? C8 H8 0.9500 . ? C9 C10 1.392(2) . ? C9 C12 1.468(2) . ? C10 C11 1.385(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.406(2) . ? C13 C14 1.385(2) . ? C13 H13 0.9500 . ? C14 C15 1.466(2) . ? C15 C18 1.395(2) . ? C15 C16 1.397(2) . ? C16 C17 1.378(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.380(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.381(2) . ? C20 H20 0.9500 . ? C21 C22 1.389(3) . ? C21 H21 0.9500 . ? C22 C23 1.395(3) . ? C22 C25 1.469(2) . ? C23 C24 1.381(2) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C26 1.400(2) . ? C26 C27 1.376(2) . ? C26 H26 0.9500 . ? C27 C28 1.464(2) . ? C28 C29 1.393(3) . ? C28 C31 1.397(2) . ? C29 C30 1.387(3) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C32 1.378(3) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn1 N1 93.11(8) . 2_654 ? N1 Zn1 O2 100.74(6) . . ? N1 Zn1 O2 95.37(5) 2_654 . ? N1 Zn1 O2 95.37(5) . 2_654 ? N1 Zn1 O2 100.74(6) 2_654 2_654 ? O2 Zn1 O2 156.51(7) . 2_654 ? N1 Zn1 O1 90.86(5) . . ? N1 Zn1 O1 155.31(5) 2_654 . ? O2 Zn1 O1 59.96(5) . . ? O2 Zn1 O1 103.13(5) 2_654 . ? N1 Zn1 O1 155.31(5) . 2_654 ? N1 Zn1 O1 90.86(5) 2_654 2_654 ? O2 Zn1 O1 103.13(5) . 2_654 ? O2 Zn1 O1 59.96(5) 2_654 2_654 ? O1 Zn1 O1 95.62(7) . 2_654 ? N1 Zn1 C1 125.34(6) . 2_654 ? N1 Zn1 C1 96.06(6) 2_654 2_654 ? O2 Zn1 C1 131.57(6) . 2_654 ? O2 Zn1 C1 30.00(5) 2_654 2_654 ? O1 Zn1 C1 101.43(5) . 2_654 ? O1 Zn1 C1 29.97(5) 2_654 2_654 ? N1 Zn1 C1 96.06(6) . . ? N1 Zn1 C1 125.34(6) 2_654 . ? O2 Zn1 C1 30.00(5) . . ? O2 Zn1 C1 131.57(6) 2_654 . ? O1 Zn1 C1 29.97(5) . . ? O1 Zn1 C1 101.43(5) 2_654 . ? C1 Zn1 C1 120.35(8) 2_654 . ? O5 Zn2 O6 125.66(6) . 7_565 ? O5 Zn2 N4 87.07(5) . . ? O6 Zn2 N4 89.08(5) 7_565 . ? O5 Zn2 N5 91.69(5) . . ? O6 Zn2 N5 90.66(5) 7_565 . ? N4 Zn2 N5 178.27(6) . . ? O5 Zn2 O4 148.07(5) . . ? O6 Zn2 O4 86.12(5) 7_565 . ? N4 Zn2 O4 90.90(5) . . ? N5 Zn2 O4 90.79(5) . . ? O5 Zn2 O3 89.89(5) . . ? O6 Zn2 O3 144.40(5) 7_565 . ? N4 Zn2 O3 91.07(5) . . ? N5 Zn2 O3 90.14(6) . . ? O4 Zn2 O3 58.28(5) . . ? O5 Zn2 C3 118.70(6) . . ? O6 Zn2 C3 115.55(6) 7_565 . ? N4 Zn2 C3 91.05(6) . . ? N5 Zn2 C3 90.61(6) . . ? O4 Zn2 C3 29.43(5) . . ? O3 Zn2 C3 28.84(5) . . ? C1 O1 Zn1 87.67(11) . . ? C1 O2 Zn1 92.56(11) . . ? C3 O3 Zn2 89.46(11) . . ? C3 O4 Zn2 92.51(11) . . ? C5 O5 Zn2 135.68(13) . . ? C5 O6 Zn2 140.43(12) . 7_565 ? C11 N1 C7 117.45(15) . . ? C11 N1 Zn1 125.98(12) . . ? C7 N1 Zn1 116.57(11) . . ? N3 N2 C12 104.89(14) . . ? N2 N3 C14 112.85(14) . . ? N2 N3 H3 123.6 . . ? C14 N3 H3 123.6 . . ? C17 N4 C19 116.93(15) . . ? C17 N4 Zn2 121.11(12) . . ? C19 N4 Zn2 121.89(12) . . ? C20 N5 C24 116.75(15) . . ? C20 N5 Zn2 120.23(12) . . ? C24 N5 Zn2 122.87(12) . . ? C25 N6 N7 104.36(14) . . ? N6 N7 C27 112.95(14) . . ? N6 N7 H71 123.5 . . ? C27 N7 H71 123.5 . . ? C32 N8 C30 115.49(17) . . ? O1 C1 O2 119.77(17) . . ? O1 C1 C2 120.14(18) . . ? O2 C1 C2 120.10(18) . . ? O1 C1 Zn1 62.36(10) . . ? O2 C1 Zn1 57.44(9) . . ? C2 C1 Zn1 177.01(15) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O3 C3 O4 119.75(17) . . ? O3 C3 C4 120.96(18) . . ? O4 C3 C4 119.29(18) . . ? O3 C3 Zn2 61.69(10) . . ? O4 C3 Zn2 58.05(9) . . ? C4 C3 Zn2 177.30(15) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C4 H4D 109.5 . . ? H4A C4 H4D 141.1 . . ? H4B C4 H4D 56.3 . . ? H4C C4 H4D 56.3 . . ? C3 C4 H4E 109.5 . . ? H4A C4 H4E 56.3 . . ? H4B C4 H4E 141.1 . . ? H4C C4 H4E 56.3 . . ? H4D C4 H4E 109.5 . . ? C3 C4 H4F 109.5 . . ? H4A C4 H4F 56.3 . . ? H4B C4 H4F 56.3 . . ? H4C C4 H4F 141.1 . . ? H4D C4 H4F 109.5 . . ? H4E C4 H4F 109.5 . . ? O5 C5 O6 126.44(18) . . ? O5 C5 C6 116.17(17) . . ? O6 C5 C6 117.39(18) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 C8 123.13(16) . . ? N1 C7 H7 118.4 . . ? C8 C7 H7 118.4 . . ? C7 C8 C9 119.72(17) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C10 C9 C8 117.20(16) . . ? C10 C9 C12 122.91(16) . . ? C8 C9 C12 119.88(16) . . ? C11 C10 C9 119.46(16) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? N1 C11 C10 123.04(16) . . ? N1 C11 H11 118.5 . . ? C10 C11 H11 118.5 . . ? N2 C12 C13 111.04(15) . . ? N2 C12 C9 118.42(15) . . ? C13 C12 C9 130.54(16) . . ? C14 C13 C12 105.00(15) . . ? C14 C13 H13 127.5 . . ? C12 C13 H13 127.5 . . ? N3 C14 C13 106.21(15) . . ? N3 C14 C15 121.90(15) . . ? C13 C14 C15 131.88(16) . . ? C18 C15 C16 117.27(16) . . ? C18 C15 C14 121.04(16) . . ? C16 C15 C14 121.69(15) . . ? C17 C16 C15 119.31(16) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? N4 C17 C16 123.66(17) . . ? N4 C17 H17 118.2 . . ? C16 C17 H17 118.2 . . ? C19 C18 C15 119.49(17) . . ? C19 C18 H18 120.3 . . ? C15 C18 H18 120.3 . . ? N4 C19 C18 123.34(17) . . ? N4 C19 H19 118.3 . . ? C18 C19 H19 118.3 . . ? N5 C20 C21 123.48(17) . . ? N5 C20 H20 118.3 . . ? C21 C20 H20 118.3 . . ? C20 C21 C22 119.81(17) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? C21 C22 C23 116.96(16) . . ? C21 C22 C25 120.85(16) . . ? C23 C22 C25 122.19(16) . . ? C24 C23 C22 119.52(17) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? N5 C24 C23 123.44(17) . . ? N5 C24 H24 118.3 . . ? C23 C24 H24 118.3 . . ? N6 C25 C26 111.16(15) . . ? N6 C25 C22 120.39(16) . . ? C26 C25 C22 128.45(16) . . ? C27 C26 C25 105.64(16) . . ? C27 C26 H26 127.2 . . ? C25 C26 H26 127.2 . . ? N7 C27 C26 105.89(15) . . ? N7 C27 C28 123.22(15) . . ? C26 C27 C28 130.89(17) . . ? C29 C28 C31 116.92(16) . . ? C29 C28 C27 120.58(16) . . ? C31 C28 C27 122.49(16) . . ? C30 C29 C28 119.41(18) . . ? C30 C29 H29 120.3 . . ? C28 C29 H29 120.3 . . ? N8 C30 C29 124.15(19) . . ? N8 C30 H30 117.9 . . ? C29 C30 H30 117.9 . . ? C32 C31 C28 118.94(17) . . ? C32 C31 H31 120.5 . . ? C28 C31 H31 120.5 . . ? N8 C32 C31 125.08(18) . . ? N8 C32 H32 117.5 . . ? C31 C32 H32 117.5 . . ? 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 N1 Zn1 O1 C1 -100.68(11) . . . . ? N1 Zn1 O1 C1 -1.32(18) 2_654 . . . ? O2 Zn1 O1 C1 1.24(10) . . . . ? O2 Zn1 O1 C1 163.60(10) 2_654 . . . ? O1 Zn1 O1 C1 103.17(11) 2_654 . . . ? C1 Zn1 O1 C1 132.93(10) 2_654 . . . ? N1 Zn1 O2 C1 83.48(11) . . . . ? N1 Zn1 O2 C1 177.69(11) 2_654 . . . ? O2 Zn1 O2 C1 -49.01(10) 2_654 . . . ? O1 Zn1 O2 C1 -1.24(10) . . . . ? O1 Zn1 O2 C1 -90.17(11) 2_654 . . . ? C1 Zn1 O2 C1 -79.30(15) 2_654 . . . ? O5 Zn2 O3 C3 177.30(12) . . . . ? O6 Zn2 O3 C3 0.32(16) 7_565 . . . ? N4 Zn2 O3 C3 90.23(12) . . . . ? N5 Zn2 O3 C3 -91.01(12) . . . . ? O4 Zn2 O3 C3 -0.16(10) . . . . ? O5 Zn2 O4 C3 -4.64(16) . . . . ? O6 Zn2 O4 C3 -179.55(11) 7_565 . . . ? N4 Zn2 O4 C3 -90.54(11) . . . . ? N5 Zn2 O4 C3 89.83(11) . . . . ? O3 Zn2 O4 C3 0.16(10) . . . . ? O6 Zn2 O5 C5 -37.91(19) 7_565 . . . ? N4 Zn2 O5 C5 -124.66(18) . . . . ? N5 Zn2 O5 C5 54.12(18) . . . . ? O4 Zn2 O5 C5 148.34(16) . . . . ? O3 Zn2 O5 C5 144.26(18) . . . . ? C3 Zn2 O5 C5 145.75(17) . . . . ? N1 Zn1 N1 C11 115.52(16) 2_654 . . . ? O2 Zn1 N1 C11 -148.42(14) . . . . ? O2 Zn1 N1 C11 14.42(15) 2_654 . . . ? O1 Zn1 N1 C11 -88.86(14) . . . . ? O1 Zn1 N1 C11 16.6(2) 2_654 . . . ? C1 Zn1 N1 C11 15.83(17) 2_654 . . . ? C1 Zn1 N1 C11 -118.44(14) . . . . ? N1 Zn1 N1 C7 -64.03(11) 2_654 . . . ? O2 Zn1 N1 C7 32.04(13) . . . . ? O2 Zn1 N1 C7 -165.13(12) 2_654 . . . ? O1 Zn1 N1 C7 91.60(13) . . . . ? O1 Zn1 N1 C7 -162.90(12) 2_654 . . . ? C1 Zn1 N1 C7 -163.71(12) 2_654 . . . ? C1 Zn1 N1 C7 62.01(13) . . . . ? C12 N2 N3 C14 0.07(19) . . . . ? O5 Zn2 N4 C17 150.18(14) . . . . ? O6 Zn2 N4 C17 24.40(14) 7_565 . . . ? N5 Zn2 N4 C17 105.7(19) . . . . ? O4 Zn2 N4 C17 -61.70(14) . . . . ? O3 Zn2 N4 C17 -119.99(14) . . . . ? C3 Zn2 N4 C17 -91.14(14) . . . . ? O5 Zn2 N4 C19 -33.05(15) . . . . ? O6 Zn2 N4 C19 -158.82(15) 7_565 . . . ? N5 Zn2 N4 C19 -77(2) . . . . ? O4 Zn2 N4 C19 115.07(14) . . . . ? O3 Zn2 N4 C19 56.79(14) . . . . ? C3 Zn2 N4 C19 85.64(15) . . . . ? O5 Zn2 N5 C20 -155.46(14) . . . . ? O6 Zn2 N5 C20 -29.75(14) 7_565 . . . ? N4 Zn2 N5 C20 -111.1(19) . . . . ? O4 Zn2 N5 C20 56.38(14) . . . . ? O3 Zn2 N5 C20 114.65(14) . . . . ? C3 Zn2 N5 C20 85.81(14) . . . . ? O5 Zn2 N5 C24 20.03(15) . . . . ? O6 Zn2 N5 C24 145.74(14) 7_565 . . . ? N4 Zn2 N5 C24 64(2) . . . . ? O4 Zn2 N5 C24 -128.14(14) . . . . ? O3 Zn2 N5 C24 -69.86(14) . . . . ? C3 Zn2 N5 C24 -98.70(14) . . . . ? C25 N6 N7 C27 0.11(19) . . . . ? Zn1 O1 C1 O2 -2.09(17) . . . . ? Zn1 O1 C1 C2 178.12(17) . . . . ? Zn1 O2 C1 O1 2.19(18) . . . . ? Zn1 O2 C1 C2 -178.01(17) . . . . ? N1 Zn1 C1 O1 81.15(11) . . . . ? N1 Zn1 C1 O1 179.32(9) 2_654 . . . ? O2 Zn1 C1 O1 -177.85(17) . . . . ? O2 Zn1 C1 O1 -21.56(13) 2_654 . . . ? O1 Zn1 C1 O1 -81.34(12) 2_654 . . . ? C1 Zn1 C1 O1 -56.26(9) 2_654 . . . ? N1 Zn1 C1 O2 -101.00(11) . . . . ? N1 Zn1 C1 O2 -2.82(13) 2_654 . . . ? O2 Zn1 C1 O2 156.29(9) 2_654 . . . ? O1 Zn1 C1 O2 177.85(17) . . . . ? O1 Zn1 C1 O2 96.51(11) 2_654 . . . ? C1 Zn1 C1 O2 121.59(11) 2_654 . . . ? N1 Zn1 C1 C2 -66(3) . . . . ? N1 Zn1 C1 C2 32(3) 2_654 . . . ? O2 Zn1 C1 C2 35(3) . . . . ? O2 Zn1 C1 C2 -169(3) 2_654 . . . ? O1 Zn1 C1 C2 -147(3) . . . . ? O1 Zn1 C1 C2 132(3) 2_654 . . . ? C1 Zn1 C1 C2 157(3) 2_654 . . . ? Zn2 O3 C3 O4 0.28(18) . . . . ? Zn2 O3 C3 C4 -179.44(18) . . . . ? Zn2 O4 C3 O3 -0.29(18) . . . . ? Zn2 O4 C3 C4 179.43(18) . . . . ? O5 Zn2 C3 O3 -3.08(13) . . . . ? O6 Zn2 C3 O3 -179.79(10) 7_565 . . . ? N4 Zn2 C3 O3 -90.31(11) . . . . ? N5 Zn2 C3 O3 89.18(12) . . . . ? O4 Zn2 C3 O3 179.72(18) . . . . ? O5 Zn2 C3 O4 177.20(9) . . . . ? O6 Zn2 C3 O4 0.49(12) 7_565 . . . ? N4 Zn2 C3 O4 89.97(11) . . . . ? N5 Zn2 C3 O4 -90.53(11) . . . . ? O3 Zn2 C3 O4 -179.72(18) . . . . ? O5 Zn2 C3 C4 167(3) . . . . ? O6 Zn2 C3 C4 -10(3) 7_565 . . . ? N4 Zn2 C3 C4 79(3) . . . . ? N5 Zn2 C3 C4 -101(3) . . . . ? O4 Zn2 C3 C4 -11(3) . . . . ? O3 Zn2 C3 C4 170(3) . . . . ? Zn2 O5 C5 O6 9.3(3) . . . . ? Zn2 O5 C5 C6 -170.56(15) . . . . ? Zn2 O6 C5 O5 33.5(3) 7_565 . . . ? Zn2 O6 C5 C6 -146.55(17) 7_565 . . . ? C11 N1 C7 C8 0.4(3) . . . . ? Zn1 N1 C7 C8 -179.97(14) . . . . ? N1 C7 C8 C9 0.2(3) . . . . ? C7 C8 C9 C10 -0.6(2) . . . . ? C7 C8 C9 C12 -179.93(16) . . . . ? C8 C9 C10 C11 0.5(2) . . . . ? C12 C9 C10 C11 179.74(16) . . . . ? C7 N1 C11 C10 -0.6(3) . . . . ? Zn1 N1 C11 C10 179.84(13) . . . . ? C9 C10 C11 N1 0.2(3) . . . . ? N3 N2 C12 C13 0.00(19) . . . . ? N3 N2 C12 C9 179.83(14) . . . . ? C10 C9 C12 N2 -171.29(16) . . . . ? C8 C9 C12 N2 8.0(2) . . . . ? C10 C9 C12 C13 8.5(3) . . . . ? C8 C9 C12 C13 -172.25(17) . . . . ? N2 C12 C13 C14 -0.1(2) . . . . ? C9 C12 C13 C14 -179.87(17) . . . . ? N2 N3 C14 C13 -0.12(19) . . . . ? N2 N3 C14 C15 179.09(15) . . . . ? C12 C13 C14 N3 0.11(19) . . . . ? C12 C13 C14 C15 -178.99(18) . . . . ? N3 C14 C15 C18 -174.91(16) . . . . ? C13 C14 C15 C18 4.1(3) . . . . ? N3 C14 C15 C16 5.4(3) . . . . ? C13 C14 C15 C16 -175.60(18) . . . . ? C18 C15 C16 C17 0.6(3) . . . . ? C14 C15 C16 C17 -179.68(17) . . . . ? C19 N4 C17 C16 -0.5(3) . . . . ? Zn2 N4 C17 C16 176.45(15) . . . . ? C15 C16 C17 N4 -0.1(3) . . . . ? C16 C15 C18 C19 -0.5(3) . . . . ? C14 C15 C18 C19 179.78(17) . . . . ? C17 N4 C19 C18 0.6(3) . . . . ? Zn2 N4 C19 C18 -176.30(15) . . . . ? C15 C18 C19 N4 -0.1(3) . . . . ? C24 N5 C20 C21 -2.0(3) . . . . ? Zn2 N5 C20 C21 173.78(15) . . . . ? N5 C20 C21 C22 0.6(3) . . . . ? C20 C21 C22 C23 1.1(3) . . . . ? C20 C21 C22 C25 -179.20(17) . . . . ? C21 C22 C23 C24 -1.5(3) . . . . ? C25 C22 C23 C24 178.85(16) . . . . ? C20 N5 C24 C23 1.6(3) . . . . ? Zn2 N5 C24 C23 -174.04(14) . . . . ? C22 C23 C24 N5 0.1(3) . . . . ? N7 N6 C25 C26 -0.24(19) . . . . ? N7 N6 C25 C22 179.09(15) . . . . ? C21 C22 C25 N6 173.49(17) . . . . ? C23 C22 C25 N6 -6.8(3) . . . . ? C21 C22 C25 C26 -7.3(3) . . . . ? C23 C22 C25 C26 172.36(18) . . . . ? N6 C25 C26 C27 0.3(2) . . . . ? C22 C25 C26 C27 -178.98(17) . . . . ? N6 N7 C27 C26 0.1(2) . . . . ? N6 N7 C27 C28 -179.17(15) . . . . ? C25 C26 C27 N7 -0.20(19) . . . . ? C25 C26 C27 C28 178.94(17) . . . . ? N7 C27 C28 C29 -176.71(17) . . . . ? C26 C27 C28 C29 4.3(3) . . . . ? N7 C27 C28 C31 3.7(3) . . . . ? C26 C27 C28 C31 -175.34(18) . . . . ? C31 C28 C29 C30 -0.3(3) . . . . ? C27 C28 C29 C30 -179.94(18) . . . . ? C32 N8 C30 C29 0.0(3) . . . . ? C28 C29 C30 N8 0.4(3) . . . . ? C29 C28 C31 C32 -0.1(3) . . . . ? C27 C28 C31 C32 179.50(17) . . . . ? C30 N8 C32 C31 -0.5(3) . . . . ? C28 C31 C32 N8 0.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.346 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.067 data_k07adb17 _database_code_depnum_ccdc_archive 'CCDC 781645' #TrackingRef 'c0ce00310g.cif' _database_code_depnum_ccdc_archive 'CCDC 781645' #TrackingRef '- burrows-dpp.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17.50 H18 N4 O4.50 Zn' _chemical_formula_weight 421.73 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 13.9650(5) _cell_length_b 10.8130(4) _cell_length_c 24.2060(8) _cell_angle_alpha 90.00 _cell_angle_beta 98.454(2) _cell_angle_gamma 90.00 _cell_volume 3615.5(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 56466 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1736 _exptl_absorpt_coefficient_mu 1.393 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19661 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4117 _reflns_number_gt 3109 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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. The methanol carbon is located at a special position in the space group and consequently the solvent fragment is disordered. Thus, since the partial methyl hydrogen atoms could not be reliably located, they were omitted from the final least-squares refinement. ; _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^)+(0.0517P)^2^+8.5737P] 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 4117 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1217 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.35447(3) 0.27515(4) 0.558543(14) 0.03327(14) Uani 1 1 d . . . O1 O 0.46722(16) 0.1946(2) 0.61146(9) 0.0352(5) Uani 1 1 d . . . O2 O 0.5020(2) 0.3895(3) 0.61070(15) 0.0710(9) Uani 1 1 d . . . O3 O 0.31853(17) 0.4451(2) 0.52804(9) 0.0391(5) Uani 1 1 d . . . O4 O 0.21769(17) 0.3915(2) 0.45189(9) 0.0472(6) Uani 1 1 d . . . O5 O 0.5243(5) 0.5260(5) 0.7182(2) 0.0667(16) Uani 0.50 1 d P A -1 H5A H 0.5053 0.5069 0.6847 0.080 Uiso 0.50 1 calc PR A -1 N1 N 0.62210(19) 0.0089(3) 0.28642(10) 0.0340(6) Uani 1 1 d . . . N2 N 0.57769(18) 0.0218(2) 0.33190(10) 0.0322(6) Uani 1 1 d . . . H2 H 0.5597 -0.0412 0.3510 0.039 Uiso 1 1 calc R . . N3 N 0.42856(18) 0.2380(3) 0.48696(10) 0.0320(6) Uani 1 1 d . . . N4 N 0.77714(18) 0.1908(3) 0.12752(10) 0.0335(6) Uani 1 1 d . . . C1 C 0.7723(2) 0.0766(3) 0.14920(12) 0.0355(7) Uani 1 1 d . . . H4 H 0.8006 0.0100 0.1318 0.043 Uiso 1 1 calc R . . C2 C 0.7281(2) 0.0516(3) 0.19546(12) 0.0347(7) Uani 1 1 d . . . H3 H 0.7271 -0.0303 0.2095 0.042 Uiso 1 1 calc R . . C3 C 0.6849(2) 0.1477(3) 0.22136(11) 0.0294(6) Uani 1 1 d . . . C4 C 0.6896(2) 0.2653(3) 0.19896(12) 0.0341(7) Uani 1 1 d . . . H5 H 0.6612 0.3335 0.2152 0.041 Uiso 1 1 calc R . . C5 C 0.7359(2) 0.2825(3) 0.15290(12) 0.0356(7) Uani 1 1 d . . . H6 H 0.7387 0.3639 0.1384 0.043 Uiso 1 1 calc R . . C6 C 0.6365(2) 0.1250(3) 0.27054(11) 0.0283(6) Uani 1 1 d . . . C7 C 0.6011(2) 0.2117(3) 0.30590(11) 0.0299(6) Uani 1 1 d . . . H1 H 0.6027 0.2993 0.3033 0.036 Uiso 1 1 calc R . . C8 C 0.5635(2) 0.1412(3) 0.34522(11) 0.0286(6) Uani 1 1 d . . . C9 C 0.4322(2) 0.1218(3) 0.46897(13) 0.0381(8) Uani 1 1 d . . . H10 H 0.4036 0.0593 0.4888 0.046 Uiso 1 1 calc R . . C10 C 0.4747(2) 0.0860(3) 0.42353(13) 0.0357(7) Uani 1 1 d . . . H7 H 0.4748 0.0016 0.4127 0.043 Uiso 1 1 calc R . . C11 C 0.5177(2) 0.1756(3) 0.39377(11) 0.0285(6) Uani 1 1 d . . . C12 C 0.5152(2) 0.2968(3) 0.41219(12) 0.0342(7) Uani 1 1 d . . . H8 H 0.5442 0.3608 0.3934 0.041 Uiso 1 1 calc R . . C13 C 0.4699(2) 0.3244(3) 0.45832(12) 0.0343(7) Uani 1 1 d . . . H9 H 0.4683 0.4081 0.4701 0.041 Uiso 1 1 calc R . . C14 C 0.5224(3) 0.2829(3) 0.62635(15) 0.0421(8) Uani 1 1 d . . . C15 C 0.6162(3) 0.2539(5) 0.6641(2) 0.0708(13) Uani 1 1 d . . . H12 H 0.6513 0.3309 0.6744 0.106 Uiso 1 1 calc R . . H13 H 0.6561 0.1996 0.6444 0.106 Uiso 1 1 calc R . . H11 H 0.6018 0.2124 0.6979 0.106 Uiso 1 1 calc R . . C16 C 0.2702(2) 0.4671(3) 0.48125(13) 0.0364(7) Uani 1 1 d . . . C17 C 0.2767(3) 0.5957(4) 0.45844(17) 0.0596(11) Uani 1 1 d . . . H16 H 0.2169 0.6152 0.4334 0.089 Uiso 1 1 calc R . . H14 H 0.3318 0.6007 0.4377 0.089 Uiso 1 1 calc R . . H15 H 0.2856 0.6551 0.4894 0.089 Uiso 1 1 calc R . . C18 C 0.5000 0.4418(8) 0.7500 0.082(2) Uani 1 2 d S . . 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 0.0375(2) 0.0400(2) 0.0255(2) 0.00123(14) 0.01543(14) 0.00839(16) O1 0.0405(12) 0.0376(13) 0.0306(11) 0.0012(9) 0.0153(9) -0.0013(10) O2 0.0553(17) 0.0414(17) 0.114(3) 0.0197(16) 0.0066(17) 0.0032(13) O3 0.0496(14) 0.0374(13) 0.0321(12) -0.0020(9) 0.0121(10) 0.0046(10) O4 0.0439(14) 0.0620(17) 0.0403(13) -0.0171(11) 0.0210(10) -0.0142(12) O5 0.094(5) 0.047(4) 0.062(4) 0.001(3) 0.022(3) -0.002(3) N1 0.0387(14) 0.0405(16) 0.0266(12) 0.0013(11) 0.0180(11) 0.0013(11) N2 0.0385(14) 0.0375(15) 0.0246(12) 0.0046(10) 0.0180(10) -0.0004(11) N3 0.0323(13) 0.0428(16) 0.0232(12) 0.0025(10) 0.0121(10) 0.0058(11) N4 0.0368(14) 0.0428(16) 0.0237(12) -0.0017(10) 0.0138(10) -0.0084(11) C1 0.0409(18) 0.042(2) 0.0271(15) -0.0017(13) 0.0161(13) 0.0009(14) C2 0.0424(18) 0.0346(18) 0.0298(15) 0.0031(12) 0.0146(13) 0.0000(14) C3 0.0291(15) 0.0380(17) 0.0227(13) -0.0010(12) 0.0088(11) -0.0039(12) C4 0.0435(18) 0.0342(18) 0.0274(15) -0.0027(12) 0.0149(13) -0.0043(14) C5 0.0496(19) 0.0324(18) 0.0279(15) -0.0011(12) 0.0163(14) -0.0094(14) C6 0.0270(14) 0.0355(18) 0.0240(14) 0.0028(11) 0.0085(11) 0.0003(12) C7 0.0345(16) 0.0316(17) 0.0256(14) 0.0017(11) 0.0109(12) -0.0006(12) C8 0.0309(15) 0.0346(17) 0.0214(13) -0.0008(11) 0.0077(11) 0.0000(12) C9 0.0435(18) 0.038(2) 0.0383(16) 0.0084(14) 0.0236(14) 0.0082(14) C10 0.0436(18) 0.0306(17) 0.0379(16) 0.0015(13) 0.0226(14) 0.0043(13) C11 0.0273(14) 0.0373(17) 0.0222(13) 0.0000(12) 0.0082(11) 0.0029(12) C12 0.0377(17) 0.0388(19) 0.0286(15) -0.0012(12) 0.0126(12) -0.0044(13) C13 0.0387(17) 0.0374(18) 0.0286(15) -0.0068(13) 0.0116(12) -0.0011(14) C14 0.0424(19) 0.036(2) 0.050(2) 0.0041(15) 0.0109(15) 0.0034(15) C15 0.053(3) 0.068(3) 0.083(3) -0.008(2) -0.018(2) 0.014(2) C16 0.0351(17) 0.044(2) 0.0324(17) -0.0053(14) 0.0146(13) -0.0005(14) C17 0.062(3) 0.058(3) 0.054(2) 0.0089(19) -0.0042(19) 0.001(2) C18 0.082(5) 0.082(5) 0.078(5) 0.000 -0.003(4) 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 O3 2.016(2) . ? Zn1 O4 2.062(2) 7_556 ? Zn1 O1 2.070(2) . ? Zn1 N4 2.149(2) 8_456 ? Zn1 N3 2.182(2) . ? O1 C14 1.246(4) . ? O2 C14 1.233(4) . ? O3 C16 1.253(4) . ? O4 C16 1.248(4) . ? O4 Zn1 2.062(2) 7_556 ? O5 C18 1.270(8) . ? O5 H5A 0.8400 . ? N1 C6 1.337(4) . ? N1 N2 1.348(3) . ? N2 C8 1.352(4) . ? N2 H2 0.8800 . ? N3 C9 1.333(4) . ? N3 C13 1.343(4) . ? N4 C5 1.340(4) . ? N4 C1 1.347(4) . ? N4 Zn1 2.149(2) 8 ? C1 C2 1.383(4) . ? C1 H4 0.9500 . ? C2 C3 1.395(4) . ? C2 H3 0.9500 . ? C3 C4 1.388(4) . ? C3 C6 1.473(4) . ? C4 C5 1.381(4) . ? C4 H5 0.9500 . ? C5 H6 0.9500 . ? C6 C7 1.407(4) . ? C7 C8 1.382(4) . ? C7 H1 0.9500 . ? C8 C11 1.467(4) . ? C9 C10 1.380(4) . ? C9 H10 0.9500 . ? C10 C11 1.394(4) . ? C10 H7 0.9500 . ? C11 C12 1.387(5) . ? C12 C13 1.394(4) . ? C12 H8 0.9500 . ? C13 H9 0.9500 . ? C14 C15 1.516(5) . ? C15 H12 0.9800 . ? C15 H13 0.9800 . ? C15 H11 0.9800 . ? C16 C17 1.504(5) . ? C17 H16 0.9800 . ? C17 H14 0.9800 . ? C17 H15 0.9800 . ? C18 O5 1.270(8) 2_656 ? 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 O3 Zn1 O4 131.36(10) . 7_556 ? O3 Zn1 O1 137.37(9) . . ? O4 Zn1 O1 91.25(10) 7_556 . ? O3 Zn1 N4 90.10(9) . 8_456 ? O4 Zn1 N4 87.28(10) 7_556 8_456 ? O1 Zn1 N4 90.84(9) . 8_456 ? O3 Zn1 N3 89.93(9) . . ? O4 Zn1 N3 91.27(9) 7_556 . ? O1 Zn1 N3 90.43(9) . . ? N4 Zn1 N3 178.08(10) 8_456 . ? C14 O1 Zn1 103.8(2) . . ? C16 O3 Zn1 125.2(2) . . ? C16 O4 Zn1 151.4(2) . 7_556 ? C18 O5 H5A 109.5 . . ? C6 N1 N2 104.2(2) . . ? N1 N2 C8 113.2(2) . . ? N1 N2 H2 123.4 . . ? C8 N2 H2 123.4 . . ? C9 N3 C13 116.5(3) . . ? C9 N3 Zn1 118.6(2) . . ? C13 N3 Zn1 124.9(2) . . ? C5 N4 C1 116.7(2) . . ? C5 N4 Zn1 121.9(2) . 8 ? C1 N4 Zn1 121.3(2) . 8 ? N4 C1 C2 123.3(3) . . ? N4 C1 H4 118.4 . . ? C2 C1 H4 118.4 . . ? C1 C2 C3 119.5(3) . . ? C1 C2 H3 120.2 . . ? C3 C2 H3 120.2 . . ? C4 C3 C2 117.2(3) . . ? C4 C3 C6 121.4(3) . . ? C2 C3 C6 121.3(3) . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H5 120.2 . . ? C3 C4 H5 120.2 . . ? N4 C5 C4 123.6(3) . . ? N4 C5 H6 118.2 . . ? C4 C5 H6 118.2 . . ? N1 C6 C7 111.7(2) . . ? N1 C6 C3 119.6(3) . . ? C7 C6 C3 128.7(3) . . ? C8 C7 C6 104.7(3) . . ? C8 C7 H1 127.6 . . ? C6 C7 H1 127.6 . . ? N2 C8 C7 106.2(2) . . ? N2 C8 C11 122.0(3) . . ? C7 C8 C11 131.8(3) . . ? N3 C9 C10 124.5(3) . . ? N3 C9 H10 117.8 . . ? C10 C9 H10 117.8 . . ? C9 C10 C11 119.0(3) . . ? C9 C10 H7 120.5 . . ? C11 C10 H7 120.5 . . ? C12 C11 C10 117.2(3) . . ? C12 C11 C8 122.1(3) . . ? C10 C11 C8 120.6(3) . . ? C11 C12 C13 119.7(3) . . ? C11 C12 H8 120.1 . . ? C13 C12 H8 120.1 . . ? N3 C13 C12 123.0(3) . . ? N3 C13 H9 118.5 . . ? C12 C13 H9 118.5 . . ? O2 C14 O1 121.5(3) . . ? O2 C14 C15 121.2(4) . . ? O1 C14 C15 117.3(3) . . ? C14 C15 H12 109.5 . . ? C14 C15 H13 109.5 . . ? H12 C15 H13 109.5 . . ? C14 C15 H11 109.5 . . ? H12 C15 H11 109.5 . . ? H13 C15 H11 109.5 . . ? O4 C16 O3 125.7(3) . . ? O4 C16 C17 117.3(3) . . ? O3 C16 C17 117.0(3) . . ? C16 C17 H16 109.5 . . ? C16 C17 H14 109.5 . . ? H16 C17 H14 109.5 . . ? C16 C17 H15 109.5 . . ? H16 C17 H15 109.5 . . ? H14 C17 H15 109.5 . . ? O5 C18 O5 88.4(8) . 2_656 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.848 _refine_diff_density_min -0.777 _refine_diff_density_rms 0.080 data_k09adb05 _database_code_depnum_ccdc_archive 'CCDC 781646' #TrackingRef 'c0ce00310g.cif' _database_code_depnum_ccdc_archive 'CCDC 781646' #TrackingRef '- burrows-dpp.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H28 N8 O5 Zn' _chemical_formula_weight 645.97 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 20.0990(6) _cell_length_b 9.1430(4) _cell_length_c 17.5490(7) _cell_angle_alpha 90.00 _cell_angle_beta 115.116(2) _cell_angle_gamma 90.00 _cell_volume 2919.98(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 40525 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 25.028 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.896 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.743 _exptl_absorpt_correction_T_max 0.888 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16494 _diffrn_reflns_av_R_equivalents 0.0902 _diffrn_reflns_av_sigmaI/netI 0.0537 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2573 _reflns_number_gt 1860 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97/2 (Sheldrick 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick 1997)' _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^)+(0.0784P)^2^+4.4982P] 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 2573 _refine_ls_number_parameters 225 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0904 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.1696 _refine_ls_wR_factor_gt 0.1443 _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_restrained_S_all 1.170 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.0000 0.08299(8) -0.2500 0.0517(3) Uani 1 2 d S . . O1 O -0.0574(4) 0.0124(7) -0.1953(4) 0.0731(18) Uani 0.60 1 d PD A 1 O2 O 0.0203(3) -0.1454(8) -0.1060(5) 0.0736(18) Uani 0.60 1 d PD A 1 O3 O 0.0464(5) 0.6279(11) 0.0352(6) 0.101(3) Uani 0.50 1 d P . . O1A O -0.0029(4) -0.0789(8) -0.1707(5) 0.0415(16) Uiso 0.40 1 d PD A 2 O2A O -0.0790(5) 0.0853(10) -0.1580(6) 0.066(2) Uiso 0.40 1 d PD A 2 N1 N 0.0795(2) 0.2157(4) -0.1684(2) 0.0534(10) Uani 1 1 d . A . N2 N 0.3065(2) 0.5090(4) 0.0147(2) 0.0485(9) Uani 1 1 d . . . N3 N 0.3403(2) 0.6071(4) 0.0755(2) 0.0441(9) Uani 1 1 d D . . N4 N 0.3625(2) 0.9874(4) 0.3032(2) 0.0539(10) Uani 1 1 d . A . C1 C 0.0650(3) 0.2918(6) -0.1123(3) 0.0580(13) Uani 1 1 d . . . H1 H 0.0183 0.2798 -0.1114 0.070 Uiso 1 1 calc R A . C2 C 0.1147(3) 0.3871(5) -0.0555(3) 0.0571(13) Uani 1 1 d . A . H2 H 0.1014 0.4406 -0.0176 0.069 Uiso 1 1 calc R . . C3 C 0.1837(3) 0.4050(5) -0.0535(3) 0.0474(11) Uani 1 1 d . . . C4 C 0.1996(3) 0.3233(5) -0.1108(3) 0.0500(11) Uani 1 1 d . A . H4 H 0.2466 0.3302 -0.1113 0.060 Uiso 1 1 calc R . . C5 C 0.1463(3) 0.2320(5) -0.1669(3) 0.0530(12) Uani 1 1 d . . . H5 H 0.1576 0.1783 -0.2062 0.064 Uiso 1 1 calc R A . C6 C 0.2379(3) 0.5053(4) 0.0066(3) 0.0451(11) Uani 1 1 d . A . C7 C 0.2280(3) 0.6031(4) 0.0622(3) 0.0437(10) Uani 1 1 d . . . H7 H 0.1840 0.6209 0.0685 0.052 Uiso 1 1 calc R A . C8 C 0.2948(2) 0.6674(4) 0.1056(2) 0.0400(10) Uani 1 1 d . A . C9 C 0.3185(2) 0.7780(4) 0.1730(3) 0.0416(10) Uani 1 1 d . . . C10 C 0.2693(3) 0.8381(5) 0.2003(3) 0.0456(10) Uani 1 1 d . A . H10 H 0.2193 0.8087 0.1751 0.055 Uiso 1 1 calc R . . C11 C 0.2928(3) 0.9410(5) 0.2642(3) 0.0526(12) Uani 1 1 d . . . H11 H 0.2577 0.9809 0.2813 0.063 Uiso 1 1 calc R A . C12 C 0.4094(3) 0.9294(5) 0.2754(3) 0.0523(12) Uani 1 1 d . . . H12 H 0.4591 0.9613 0.3012 0.063 Uiso 1 1 calc R A . C13 C 0.3908(2) 0.8276(5) 0.2127(3) 0.0477(11) Uani 1 1 d . A . H13 H 0.4270 0.7909 0.1962 0.057 Uiso 1 1 calc R . . C14 C -0.0399(7) -0.0793(17) -0.1365(7) 0.053(3) Uani 0.60 1 d PD A 1 C15 C -0.0925(5) -0.1028(11) -0.0969(6) 0.056(2) Uani 0.60 1 d PD A 1 H15A H -0.1360 -0.0414 -0.1254 0.084 Uiso 0.60 1 calc PR A 1 H15B H -0.0684 -0.0764 -0.0372 0.084 Uiso 0.60 1 calc PR A 1 H15C H -0.1072 -0.2058 -0.1024 0.084 Uiso 0.60 1 calc PR A 1 C14A C -0.0449(12) -0.0344(16) -0.1393(13) 0.041(6) Uiso 0.40 1 d PD A 2 C15A C -0.0579(8) -0.1322(15) -0.0776(8) 0.052(4) Uiso 0.40 1 d PD A 2 H15D H -0.0310 -0.2242 -0.0714 0.078 Uiso 0.40 1 calc PR A 2 H15E H -0.1105 -0.1527 -0.0985 0.078 Uiso 0.40 1 calc PR A 2 H15F H -0.0405 -0.0831 -0.0229 0.078 Uiso 0.40 1 calc PR A 2 H3 H 0.3890(5) 0.620(4) 0.093(2) 0.036(12) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0703(6) 0.0370(4) 0.0400(4) 0.000 0.0159(4) 0.000 O1 0.105(5) 0.069(4) 0.052(4) -0.001(3) 0.039(4) -0.023(4) O2 0.043(3) 0.076(4) 0.095(5) -0.019(4) 0.023(3) 0.000(3) O3 0.104(6) 0.131(8) 0.102(7) 0.034(6) 0.076(6) 0.072(6) N1 0.070(3) 0.046(2) 0.038(2) 0.0037(17) 0.0177(19) -0.005(2) N2 0.065(3) 0.037(2) 0.043(2) 0.0013(16) 0.0224(19) -0.0020(18) N3 0.052(2) 0.036(2) 0.046(2) 0.0026(16) 0.0228(19) -0.0013(17) N4 0.062(3) 0.045(2) 0.051(2) -0.0041(18) 0.021(2) 0.000(2) C1 0.062(3) 0.062(3) 0.045(3) 0.002(2) 0.017(2) -0.010(3) C2 0.075(4) 0.053(3) 0.039(2) -0.001(2) 0.020(2) -0.007(3) C3 0.063(3) 0.034(2) 0.039(2) 0.0111(19) 0.015(2) -0.001(2) C4 0.065(3) 0.039(2) 0.043(2) 0.006(2) 0.020(2) 0.002(2) C5 0.074(3) 0.037(2) 0.042(2) 0.004(2) 0.019(2) -0.003(2) C6 0.061(3) 0.035(2) 0.034(2) 0.0085(18) 0.016(2) 0.001(2) C7 0.049(3) 0.041(2) 0.041(2) 0.0109(19) 0.018(2) 0.002(2) C8 0.051(3) 0.034(2) 0.036(2) 0.0099(17) 0.019(2) 0.0032(19) C9 0.051(3) 0.032(2) 0.040(2) 0.0088(17) 0.017(2) 0.0023(19) C10 0.047(3) 0.049(3) 0.042(2) 0.003(2) 0.020(2) -0.003(2) C11 0.060(3) 0.053(3) 0.048(3) -0.003(2) 0.026(2) 0.002(2) C12 0.049(3) 0.040(2) 0.060(3) -0.001(2) 0.016(2) -0.003(2) C13 0.050(3) 0.038(2) 0.056(3) 0.005(2) 0.023(2) 0.006(2) C14 0.065(8) 0.046(8) 0.046(6) -0.011(6) 0.020(5) -0.016(7) C15 0.039(5) 0.077(6) 0.057(5) 0.014(4) 0.025(4) 0.005(5) _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 1.899(6) 2_554 ? Zn1 O1 1.899(6) . ? Zn1 N1 2.033(4) . ? Zn1 N1 2.033(4) 2_554 ? Zn1 O1A 2.049(8) 2_554 ? Zn1 O1A 2.049(8) . ? O1 C14 1.260(12) . ? O2 C14 1.252(16) . ? O1A C14A 1.256(16) . ? O2A C14A 1.259(18) . ? N1 C1 1.335(6) . ? N1 C5 1.340(6) . ? N2 C6 1.327(6) . ? N2 N3 1.337(5) . ? N3 C8 1.353(6) . ? N3 H3 0.900(5) . ? N4 C12 1.340(6) . ? N4 C11 1.340(6) . ? C1 C2 1.381(7) . ? C1 H1 0.9500 . ? C2 C3 1.382(7) . ? C2 H2 0.9500 . ? C3 C4 1.394(7) . ? C3 C6 1.472(6) . ? C4 C5 1.386(6) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.398(6) . ? C7 C8 1.364(6) . ? C7 H7 0.9500 . ? C8 C9 1.473(6) . ? C9 C10 1.381(6) . ? C9 C13 1.394(6) . ? C10 C11 1.384(6) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.367(6) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.506(11) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C14A C15A 1.510(15) . ? C15A H15D 0.9800 . ? C15A H15E 0.9800 . ? C15A H15F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O1 140.3(4) 2_554 . ? O1 Zn1 N1 95.4(3) 2_554 . ? O1 Zn1 N1 108.1(2) . . ? O1 Zn1 N1 108.1(2) 2_554 2_554 ? O1 Zn1 N1 95.4(3) . 2_554 ? N1 Zn1 N1 106.7(2) . 2_554 ? O1 Zn1 O1A 38.1(3) 2_554 2_554 ? O1 Zn1 O1A 107.2(3) . 2_554 ? N1 Zn1 O1A 132.0(2) . 2_554 ? N1 Zn1 O1A 101.1(2) 2_554 2_554 ? O1 Zn1 O1A 107.2(3) 2_554 . ? O1 Zn1 O1A 38.1(3) . . ? N1 Zn1 O1A 101.1(2) . . ? N1 Zn1 O1A 132.0(2) 2_554 . ? O1A Zn1 O1A 87.5(4) 2_554 . ? C14 O1 Zn1 128.5(8) . . ? C14A O1A Zn1 106.4(9) . . ? C1 N1 C5 117.3(4) . . ? C1 N1 Zn1 118.6(3) . . ? C5 N1 Zn1 124.1(3) . . ? C6 N2 N3 104.8(4) . . ? N2 N3 C8 112.7(4) . . ? N2 N3 H3 118(3) . . ? C8 N3 H3 129(3) . . ? C12 N4 C11 115.7(4) . . ? N1 C1 C2 122.9(5) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 120.3(5) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 117.0(4) . . ? C2 C3 C6 121.4(4) . . ? C4 C3 C6 121.6(5) . . ? C5 C4 C3 119.3(5) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? N1 C5 C4 123.2(5) . . ? N1 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? N2 C6 C7 111.0(4) . . ? N2 C6 C3 120.8(4) . . ? C7 C6 C3 128.1(4) . . ? C8 C7 C6 105.5(4) . . ? C8 C7 H7 127.3 . . ? C6 C7 H7 127.3 . . ? N3 C8 C7 106.0(4) . . ? N3 C8 C9 123.5(4) . . ? C7 C8 C9 130.6(4) . . ? C10 C9 C13 116.4(4) . . ? C10 C9 C8 121.1(4) . . ? C13 C9 C8 122.5(4) . . ? C9 C10 C11 120.2(4) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? N4 C11 C10 123.5(5) . . ? N4 C11 H11 118.2 . . ? C10 C11 H11 118.2 . . ? N4 C12 C13 124.6(4) . . ? N4 C12 H12 117.7 . . ? C13 C12 H12 117.7 . . ? C12 C13 C9 119.7(4) . . ? C12 C13 H13 120.2 . . ? C9 C13 H13 120.2 . . ? O2 C14 O1 123.7(9) . . ? O2 C14 C15 118.4(10) . . ? O1 C14 C15 117.8(12) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O2A C14A O1A 124.1(13) . . ? O2A C14A C15A 117.4(13) . . ? O1A C14A C15A 118.4(14) . . ? C14A C15A H15D 109.5 . . ? C14A C15A H15E 109.5 . . ? H15D C15A H15E 109.5 . . ? C14A C15A H15F 109.5 . . ? H15D C15A H15F 109.5 . . ? H15E C15A H15F 109.5 . . ? 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 O1 Zn1 O1 C14 51.9(9) 2_554 . . . ? N1 Zn1 O1 C14 -71.5(10) . . . . ? N1 Zn1 O1 C14 178.9(10) 2_554 . . . ? O1A Zn1 O1 C14 75.5(10) 2_554 . . . ? O1A Zn1 O1 C14 13.5(9) . . . . ? O1 Zn1 O1A C14A -175.8(11) 2_554 . . . ? O1 Zn1 O1A C14A -20.3(11) . . . . ? N1 Zn1 O1A C14A 84.9(12) . . . . ? N1 Zn1 O1A C14A -40.0(12) 2_554 . . . ? O1A Zn1 O1A C14A -142.7(12) 2_554 . . . ? O1 Zn1 N1 C1 -178.8(4) 2_554 . . . ? O1 Zn1 N1 C1 -31.2(4) . . . . ? N1 Zn1 N1 C1 70.5(3) 2_554 . . . ? O1A Zn1 N1 C1 -166.7(4) 2_554 . . . ? O1A Zn1 N1 C1 -70.0(4) . . . . ? O1 Zn1 N1 C5 1.1(4) 2_554 . . . ? O1 Zn1 N1 C5 148.7(4) . . . . ? N1 Zn1 N1 C5 -109.7(4) 2_554 . . . ? O1A Zn1 N1 C5 13.1(5) 2_554 . . . ? O1A Zn1 N1 C5 109.8(4) . . . . ? C6 N2 N3 C8 -0.7(4) . . . . ? C5 N1 C1 C2 1.6(7) . . . . ? Zn1 N1 C1 C2 -178.6(4) . . . . ? N1 C1 C2 C3 -1.5(7) . . . . ? C1 C2 C3 C4 0.0(6) . . . . ? C1 C2 C3 C6 -179.7(4) . . . . ? C2 C3 C4 C5 1.2(6) . . . . ? C6 C3 C4 C5 -179.1(4) . . . . ? C1 N1 C5 C4 -0.3(6) . . . . ? Zn1 N1 C5 C4 179.8(3) . . . . ? C3 C4 C5 N1 -1.1(7) . . . . ? N3 N2 C6 C7 0.5(4) . . . . ? N3 N2 C6 C3 -178.1(3) . . . . ? C2 C3 C6 N2 172.0(4) . . . . ? C4 C3 C6 N2 -7.7(6) . . . . ? C2 C3 C6 C7 -6.4(7) . . . . ? C4 C3 C6 C7 173.9(4) . . . . ? N2 C6 C7 C8 -0.2(5) . . . . ? C3 C6 C7 C8 178.3(4) . . . . ? N2 N3 C8 C7 0.6(5) . . . . ? N2 N3 C8 C9 179.8(3) . . . . ? C6 C7 C8 N3 -0.3(4) . . . . ? C6 C7 C8 C9 -179.3(4) . . . . ? N3 C8 C9 C10 178.7(4) . . . . ? C7 C8 C9 C10 -2.4(7) . . . . ? N3 C8 C9 C13 -1.4(6) . . . . ? C7 C8 C9 C13 177.5(4) . . . . ? C13 C9 C10 C11 -0.4(6) . . . . ? C8 C9 C10 C11 179.5(4) . . . . ? C12 N4 C11 C10 1.2(7) . . . . ? C9 C10 C11 N4 -0.5(7) . . . . ? C11 N4 C12 C13 -1.0(7) . . . . ? N4 C12 C13 C9 0.2(7) . . . . ? C10 C9 C13 C12 0.6(6) . . . . ? C8 C9 C13 C12 -179.3(4) . . . . ? Zn1 O1 C14 O2 -3.2(18) . . . . ? Zn1 O1 C14 C15 172.6(7) . . . . ? Zn1 O1A C14A O2A 2(2) . . . . ? Zn1 O1A C14A C15A 180.0(14) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.565 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.096 data_k07adb10 _database_code_depnum_ccdc_archive 'CCDC 781647' #TrackingRef 'c0ce00310g.cif' _database_code_depnum_ccdc_archive 'CCDC 781647' #TrackingRef '- burrows-dpp.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 Cl2 N4 Zn' _chemical_formula_weight 358.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.2750(1) _cell_length_b 21.5070(3) _cell_length_c 12.2530(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.063(1) _cell_angle_gamma 90.00 _cell_volume 1364.26(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 20158 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.746 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 2.184 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.25 _exptl_absorpt_correction_T_max 0.30 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25196 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3119 _reflns_number_gt 2784 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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^)+(0.0304P)^2^+0.9853P] 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 SHELXL _refine_ls_extinction_coef 0.0020(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3119 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0317 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0658 _refine_ls_wR_factor_gt 0.0628 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.002 _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 1.07950(4) 1.351852(9) 0.639786(16) 0.01775(8) Uani 1 1 d . . . Cl1 Cl 1.12971(10) 1.38546(2) 0.47361(4) 0.02815(12) Uani 1 1 d . . . N1 N 0.8483(3) 1.27453(7) 0.61721(13) 0.0189(3) Uani 1 1 d . . . C1 C 0.6476(4) 1.27039(9) 0.53181(16) 0.0223(4) Uani 1 1 d . . . H1 H 0.6332 1.3003 0.4738 0.027 Uiso 1 1 calc R . . Cl2 Cl 1.40701(8) 1.32308(2) 0.77687(4) 0.02207(11) Uani 1 1 d . . . N2 N 0.0784(3) 1.12378(7) 0.52586(13) 0.0200(3) Uani 1 1 d . . . H2 H 0.0521 1.1459 0.4643 0.024 Uiso 1 1 calc R . . C2 C 0.4608(4) 1.22470(9) 0.52415(16) 0.0224(4) Uani 1 1 d . . . H2A H 0.3221 1.2234 0.4620 0.027 Uiso 1 1 calc R . . N3 N -0.0800(3) 1.07801(7) 0.54539(13) 0.0204(3) Uani 1 1 d . . . C3 C 0.4784(3) 1.18047(8) 0.60897(15) 0.0182(4) Uani 1 1 d . . . N4 N -0.3843(3) 0.91941(7) 0.79354(12) 0.0190(3) Uani 1 1 d . . . C4 C 0.6900(4) 1.18431(8) 0.69660(15) 0.0196(4) Uani 1 1 d . . . H4 H 0.7110 1.1547 0.7552 0.024 Uiso 1 1 calc R . . C5 C 0.8685(4) 1.23121(8) 0.69783(15) 0.0199(4) Uani 1 1 d . . . H5 H 1.0118 1.2331 0.7580 0.024 Uiso 1 1 calc R . . C6 C 0.2830(3) 1.13274(9) 0.61018(15) 0.0189(4) Uani 1 1 d . . . C7 C 0.2541(4) 1.08974(8) 0.69134(15) 0.0199(4) Uani 1 1 d . . . H7 H 0.3642 1.0838 0.7616 0.024 Uiso 1 1 calc R . . C8 C 0.0272(3) 1.05692(8) 0.64736(14) 0.0183(4) Uani 1 1 d . . . C9 C -0.4322(3) 0.92945(8) 0.68312(15) 0.0199(4) Uani 1 1 d . . . H9 H -0.5633 0.9057 0.6376 0.024 Uiso 1 1 calc R . . C10 C -0.2994(3) 0.97273(8) 0.63336(15) 0.0195(4) Uani 1 1 d . . . H10 H -0.3395 0.9785 0.5551 0.023 Uiso 1 1 calc R . . C11 C -0.1056(3) 1.00816(8) 0.69821(15) 0.0179(3) Uani 1 1 d . . . C12 C -0.0517(4) 0.99653(9) 0.81239(16) 0.0243(4) Uani 1 1 d . . . H12 H 0.0819 1.0188 0.8595 0.029 Uiso 1 1 calc R . . C13 C -0.1940(4) 0.95244(9) 0.85617(16) 0.0243(4) Uani 1 1 d . . . H13 H -0.1558 0.9451 0.9341 0.029 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 0.01817(13) 0.01801(13) 0.01703(13) -0.00163(7) 0.00328(8) -0.00085(7) Cl1 0.0326(3) 0.0338(3) 0.0185(2) 0.00347(18) 0.00599(18) -0.0011(2) N1 0.0203(8) 0.0185(8) 0.0183(7) -0.0019(6) 0.0049(6) -0.0005(6) C1 0.0247(10) 0.0213(9) 0.0200(9) 0.0025(7) 0.0019(7) -0.0006(7) Cl2 0.0199(2) 0.0255(2) 0.0195(2) -0.00369(17) 0.00061(16) 0.00201(17) N2 0.0213(8) 0.0198(8) 0.0183(8) 0.0031(6) 0.0022(6) -0.0030(6) C2 0.0232(9) 0.0231(9) 0.0193(9) 0.0020(7) 0.0003(7) -0.0030(7) N3 0.0215(8) 0.0197(8) 0.0201(8) 0.0005(6) 0.0039(6) -0.0032(6) C3 0.0185(9) 0.0169(8) 0.0202(9) -0.0017(7) 0.0060(7) 0.0006(7) N4 0.0198(8) 0.0175(7) 0.0197(8) 0.0013(6) 0.0040(6) 0.0003(6) C4 0.0210(9) 0.0188(9) 0.0192(9) 0.0018(7) 0.0041(7) 0.0011(7) C5 0.0184(9) 0.0218(9) 0.0188(9) -0.0009(7) 0.0018(7) 0.0009(7) C6 0.0178(9) 0.0195(9) 0.0195(9) -0.0023(7) 0.0039(7) 0.0002(7) C7 0.0203(9) 0.0207(9) 0.0182(9) 0.0006(7) 0.0019(7) 0.0005(7) C8 0.0187(8) 0.0173(9) 0.0185(9) -0.0007(7) 0.0029(7) 0.0010(7) C9 0.0189(9) 0.0198(9) 0.0199(9) 0.0010(7) 0.0008(7) -0.0016(7) C10 0.0199(9) 0.0207(9) 0.0170(9) 0.0020(7) 0.0016(7) 0.0006(7) C11 0.0181(9) 0.0163(8) 0.0193(9) 0.0010(7) 0.0040(7) 0.0033(7) C12 0.0268(10) 0.0247(10) 0.0200(9) -0.0013(8) 0.0009(7) -0.0064(8) C13 0.0291(10) 0.0268(10) 0.0166(9) 0.0006(7) 0.0031(7) -0.0044(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N4 2.0402(15) 2_556 ? Zn1 N1 2.0493(15) . ? Zn1 Cl1 2.2239(5) . ? Zn1 Cl2 2.2528(5) . ? N1 C1 1.341(2) . ? N1 C5 1.347(2) . ? C1 C2 1.382(3) . ? C1 H1 0.9500 . ? N2 N3 1.342(2) . ? N2 C6 1.357(2) . ? N2 H2 0.8800 . ? C2 C3 1.399(3) . ? C2 H2A 0.9500 . ? N3 C8 1.347(2) . ? C3 C4 1.395(3) . ? C3 C6 1.457(3) . ? N4 C13 1.343(2) . ? N4 C9 1.345(2) . ? N4 Zn1 2.0402(15) 2_546 ? C4 C5 1.378(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.388(3) . ? C7 C8 1.405(3) . ? C7 H7 0.9500 . ? C8 C11 1.465(3) . ? C9 C10 1.376(3) . ? C9 H9 0.9500 . ? C10 C11 1.394(3) . ? C10 H10 0.9500 . ? C11 C12 1.396(3) . ? C12 C13 1.380(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? 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 N4 Zn1 N1 107.40(6) 2_556 . ? N4 Zn1 Cl1 107.04(5) 2_556 . ? N1 Zn1 Cl1 108.21(5) . . ? N4 Zn1 Cl2 105.72(4) 2_556 . ? N1 Zn1 Cl2 103.24(5) . . ? Cl1 Zn1 Cl2 124.26(2) . . ? C1 N1 C5 117.77(16) . . ? C1 N1 Zn1 121.29(13) . . ? C5 N1 Zn1 120.06(12) . . ? N1 C1 C2 123.09(17) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? N3 N2 C6 113.56(15) . . ? N3 N2 H2 123.2 . . ? C6 N2 H2 123.2 . . ? C1 C2 C3 119.23(17) . . ? C1 C2 H2A 120.4 . . ? C3 C2 H2A 120.4 . . ? N2 N3 C8 104.32(15) . . ? C4 C3 C2 117.45(17) . . ? C4 C3 C6 119.81(16) . . ? C2 C3 C6 122.72(17) . . ? C13 N4 C9 117.73(16) . . ? C13 N4 Zn1 121.80(12) . 2_546 ? C9 N4 Zn1 120.33(12) . 2_546 ? C5 C4 C3 119.73(17) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N1 C5 C4 122.72(17) . . ? N1 C5 H5 118.6 . . ? C4 C5 H5 118.6 . . ? N2 C6 C7 105.70(16) . . ? N2 C6 C3 123.58(17) . . ? C7 C6 C3 130.70(17) . . ? C6 C7 C8 105.22(16) . . ? C6 C7 H7 127.4 . . ? C8 C7 H7 127.4 . . ? N3 C8 C7 111.20(16) . . ? N3 C8 C11 119.04(16) . . ? C7 C8 C11 129.66(16) . . ? N4 C9 C10 122.73(17) . . ? N4 C9 H9 118.6 . . ? C10 C9 H9 118.6 . . ? C9 C10 C11 119.80(17) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C12 117.35(17) . . ? C10 C11 C8 120.45(16) . . ? C12 C11 C8 122.17(17) . . ? C13 C12 C11 119.42(18) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? N4 C13 C12 122.93(17) . . ? N4 C13 H13 118.5 . . ? C12 C13 H13 118.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.349 _refine_diff_density_min -0.448 _refine_diff_density_rms 0.085 data_h07adb4 _database_code_depnum_ccdc_archive 'CCDC 781648' #TrackingRef 'c0ce00310g.cif' _database_code_depnum_ccdc_archive 'CCDC 781648' #TrackingRef '- burrows-dpp.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 N5 O6 Zn0.50' _chemical_formula_weight 399.05 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 7.4230(2) _cell_length_b 8.8460(3) _cell_length_c 14.0560(5) _cell_angle_alpha 90.480(1) _cell_angle_beta 104.689(1) _cell_angle_gamma 101.917(2) _cell_volume 871.76(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7257 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.782 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.69 _exptl_absorpt_correction_T_max 0.75 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11476 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0651 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3979 _reflns_number_gt 3138 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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^)+(0.0437P)^2^+0.0587P] 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 SHELXL _refine_ls_extinction_coef 0.013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3979 _refine_ls_number_parameters 257 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0910 _refine_ls_wR_factor_gt 0.0846 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.5000 0.5000 0.5000 0.01755(13) Uani 1 2 d S . . O1 O 0.3271(2) 0.66360(17) 0.48484(11) 0.0249(3) Uani 1 1 d D . . O2 O 0.43292(19) 0.44318(16) 0.63651(10) 0.0217(3) Uani 1 1 d D . . O3 O 0.1624(2) 0.74367(16) 0.31030(11) 0.0253(3) Uani 1 1 d . . . O4 O 0.4298(2) 0.9060(2) 0.31904(15) 0.0465(5) Uani 1 1 d . . . O5 O 0.2131(3) 0.8572(2) 0.18111(13) 0.0492(5) Uani 1 1 d . . . O6 O -0.4324(2) -0.10705(17) 0.12418(11) 0.0289(4) Uani 1 1 d D . . N1 N 0.2644(2) 0.32899(18) 0.41807(12) 0.0178(4) Uani 1 1 d . . . N2 N -0.2320(2) 0.19747(19) 0.11254(12) 0.0222(4) Uani 1 1 d . . . N3 N -0.3005(2) 0.27849(19) 0.03602(13) 0.0233(4) Uani 1 1 d . . . H3 H -0.3873 0.2367 -0.0178 0.028 Uiso 1 1 calc R . . N4 N -0.4125(2) 0.6006(2) -0.18695(12) 0.0219(4) Uani 1 1 d . . . N5 N 0.2699(3) 0.8372(2) 0.26958(15) 0.0286(4) Uani 1 1 d . . . C1 C 0.2909(3) 0.7545(3) 0.55868(18) 0.0334(6) Uani 1 1 d . . . H1A H 0.3295 0.7112 0.6227 0.050 Uiso 1 1 calc R . . H1B H 0.1545 0.7542 0.5431 0.050 Uiso 1 1 calc R . . H1C H 0.3638 0.8610 0.5612 0.050 Uiso 1 1 calc R . . C2 C 0.2499(3) 0.3678(3) 0.64970(18) 0.0359(6) Uani 1 1 d . . . H2A H 0.1492 0.3795 0.5916 0.054 Uiso 1 1 calc R . . H2B H 0.2295 0.4151 0.7083 0.054 Uiso 1 1 calc R . . H2C H 0.2469 0.2575 0.6581 0.054 Uiso 1 1 calc R . . C3 C 0.2374(3) 0.1805(2) 0.44177(15) 0.0203(5) Uani 1 1 d . . . H3A H 0.3190 0.1537 0.4999 0.024 Uiso 1 1 calc R . . C4 C 0.0953(3) 0.0659(2) 0.38463(16) 0.0225(5) Uani 1 1 d . . . H4 H 0.0772 -0.0372 0.4048 0.027 Uiso 1 1 calc R . . C5 C -0.0207(3) 0.1011(2) 0.29796(15) 0.0211(5) Uani 1 1 d . . . H5 H -0.1166 0.0225 0.2571 0.025 Uiso 1 1 calc R . . C6 C 0.0054(3) 0.2545(2) 0.27143(15) 0.0171(4) Uani 1 1 d . . . C7 C 0.1477(3) 0.3632(2) 0.33522(15) 0.0171(4) Uani 1 1 d . . . H7 H 0.1634 0.4684 0.3192 0.020 Uiso 1 1 calc R . . C8 C -0.1048(3) 0.3024(2) 0.17883(15) 0.0184(4) Uani 1 1 d . . . C9 C -0.0924(3) 0.4512(2) 0.14356(15) 0.0187(4) Uani 1 1 d . . . H9 H -0.0131 0.5454 0.1760 0.022 Uiso 1 1 calc R . . C10 C -0.2203(3) 0.4315(2) 0.05148(15) 0.0185(4) Uani 1 1 d . . . C11 C -0.3722(3) 0.5011(2) -0.11770(15) 0.0211(5) Uani 1 1 d . . . H11 H -0.4188 0.3936 -0.1355 0.025 Uiso 1 1 calc R . . C12 C -0.2659(3) 0.5456(2) -0.02103(15) 0.0190(4) Uani 1 1 d . . . C13 C -0.1982(3) 0.7040(2) 0.00345(16) 0.0235(5) Uani 1 1 d . . . H13 H -0.1236 0.7402 0.0681 0.028 Uiso 1 1 calc R . . C14 C -0.2409(3) 0.8073(2) -0.06727(16) 0.0253(5) Uani 1 1 d . . . H14 H -0.1973 0.9155 -0.0513 0.030 Uiso 1 1 calc R . . C15 C -0.3468(3) 0.7535(2) -0.16108(16) 0.0235(5) Uani 1 1 d . . . H15 H -0.3747 0.8260 -0.2092 0.028 Uiso 1 1 calc R . . H6A H -0.3592 -0.0145 0.1181 0.038(7) Uiso 1 1 d RD . . H6B H -0.517(3) -0.085(3) 0.1628(19) 0.063(9) Uiso 1 1 d D . . H2 H 0.493(3) 0.515(2) 0.6945(12) 0.050(8) Uiso 1 1 d D . . H1 H 0.280(4) 0.705(3) 0.4213(11) 0.065(9) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01663(19) 0.0198(2) 0.0134(2) -0.00010(13) 0.00041(13) 0.00206(13) O1 0.0297(8) 0.0291(8) 0.0165(8) -0.0024(7) 0.0016(6) 0.0132(7) O2 0.0207(8) 0.0253(8) 0.0160(8) -0.0007(6) 0.0047(6) -0.0019(6) O3 0.0271(8) 0.0219(8) 0.0241(9) 0.0050(6) 0.0055(6) 0.0005(6) O4 0.0265(9) 0.0365(10) 0.0650(14) 0.0031(9) 0.0026(9) -0.0074(8) O5 0.0680(13) 0.0515(12) 0.0241(10) 0.0118(9) 0.0124(9) 0.0030(10) O6 0.0292(9) 0.0255(8) 0.0255(9) -0.0024(7) 0.0044(7) -0.0053(7) N1 0.0190(9) 0.0191(9) 0.0147(9) 0.0020(7) 0.0032(7) 0.0044(7) N2 0.0216(9) 0.0228(9) 0.0158(10) 0.0018(7) -0.0015(7) -0.0015(7) N3 0.0206(9) 0.0264(10) 0.0155(9) -0.0001(8) -0.0035(7) -0.0013(7) N4 0.0215(9) 0.0286(10) 0.0142(9) 0.0021(8) 0.0038(7) 0.0035(7) N5 0.0335(11) 0.0215(10) 0.0324(12) 0.0018(9) 0.0112(9) 0.0065(8) C1 0.0407(14) 0.0370(13) 0.0264(13) -0.0031(11) 0.0088(10) 0.0174(11) C2 0.0297(13) 0.0470(15) 0.0267(13) -0.0061(11) 0.0123(10) -0.0073(11) C3 0.0196(11) 0.0225(11) 0.0173(11) 0.0013(9) 0.0010(8) 0.0058(9) C4 0.0257(11) 0.0186(10) 0.0222(12) 0.0025(9) 0.0050(9) 0.0042(9) C5 0.0193(11) 0.0196(10) 0.0208(12) -0.0028(9) 0.0024(8) 0.0001(8) C6 0.0166(10) 0.0207(10) 0.0142(10) 0.0002(8) 0.0048(8) 0.0038(8) C7 0.0177(10) 0.0175(10) 0.0154(10) 0.0019(8) 0.0033(8) 0.0036(8) C8 0.0153(10) 0.0227(11) 0.0155(11) -0.0012(8) 0.0033(8) 0.0014(8) C9 0.0176(10) 0.0193(10) 0.0167(11) -0.0021(8) 0.0030(8) 0.0002(8) C10 0.0159(10) 0.0207(10) 0.0178(11) -0.0008(8) 0.0038(8) 0.0024(8) C11 0.0192(10) 0.0246(11) 0.0167(11) -0.0007(9) 0.0025(8) 0.0014(9) C12 0.0142(10) 0.0248(11) 0.0175(11) 0.0013(9) 0.0042(8) 0.0034(8) C13 0.0236(11) 0.0272(11) 0.0163(11) -0.0022(9) 0.0013(9) 0.0026(9) C14 0.0269(12) 0.0213(11) 0.0240(12) -0.0004(9) 0.0030(9) 0.0018(9) C15 0.0243(11) 0.0277(12) 0.0200(12) 0.0054(9) 0.0081(9) 0.0060(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 2.1023(14) . ? Zn1 O1 2.1023(14) 2_666 ? Zn1 N1 2.1283(16) . ? Zn1 N1 2.1283(16) 2_666 ? Zn1 O2 2.1400(14) 2_666 ? Zn1 O2 2.1400(14) . ? O1 C1 1.419(3) . ? O2 C2 1.442(3) . ? O3 N5 1.271(2) . ? O4 N5 1.240(2) . ? O5 N5 1.234(2) . ? N1 C7 1.342(2) . ? N1 C3 1.345(2) . ? N2 C8 1.341(2) . ? N2 N3 1.347(2) . ? N3 C10 1.352(2) . ? N4 C11 1.337(3) . ? N4 C15 1.352(3) . ? C3 C4 1.379(3) . ? C4 C5 1.381(3) . ? C5 C6 1.398(3) . ? C6 C7 1.389(3) . ? C6 C8 1.468(3) . ? C8 C9 1.404(3) . ? C9 C10 1.383(3) . ? C10 C12 1.468(3) . ? C11 C12 1.394(3) . ? C12 C13 1.396(3) . ? C13 C14 1.378(3) . ? C14 C15 1.376(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O1 180.0 . 2_666 ? O1 Zn1 N1 90.46(6) . . ? O1 Zn1 N1 89.54(6) 2_666 . ? O1 Zn1 N1 89.54(6) . 2_666 ? O1 Zn1 N1 90.46(6) 2_666 2_666 ? N1 Zn1 N1 180.0 . 2_666 ? O1 Zn1 O2 91.16(6) . 2_666 ? O1 Zn1 O2 88.84(6) 2_666 2_666 ? N1 Zn1 O2 87.60(6) . 2_666 ? N1 Zn1 O2 92.40(6) 2_666 2_666 ? O1 Zn1 O2 88.84(6) . . ? O1 Zn1 O2 91.16(6) 2_666 . ? N1 Zn1 O2 92.40(6) . . ? N1 Zn1 O2 87.60(6) 2_666 . ? O2 Zn1 O2 180.0 2_666 . ? C1 O1 Zn1 129.40(13) . . ? C2 O2 Zn1 126.91(13) . . ? C7 N1 C3 117.51(17) . . ? C7 N1 Zn1 120.64(13) . . ? C3 N1 Zn1 121.56(13) . . ? C8 N2 N3 105.36(15) . . ? N2 N3 C10 112.22(16) . . ? C11 N4 C15 117.75(18) . . ? O5 N5 O4 121.22(19) . . ? O5 N5 O3 119.16(19) . . ? O4 N5 O3 119.6(2) . . ? N1 C3 C4 122.28(19) . . ? C3 C4 C5 119.86(19) . . ? C4 C5 C6 118.88(19) . . ? C7 C6 C5 117.25(18) . . ? C7 C6 C8 119.75(17) . . ? C5 C6 C8 122.96(18) . . ? N1 C7 C6 124.14(18) . . ? N2 C8 C9 110.62(17) . . ? N2 C8 C6 120.73(17) . . ? C9 C8 C6 128.59(18) . . ? C10 C9 C8 105.22(18) . . ? N3 C10 C9 106.58(17) . . ? N3 C10 C12 123.50(18) . . ? C9 C10 C12 129.91(18) . . ? N4 C11 C12 123.96(19) . . ? C11 C12 C13 117.11(19) . . ? C11 C12 C10 121.85(18) . . ? C13 C12 C10 121.00(18) . . ? C14 C13 C12 119.25(19) . . ? C15 C14 C13 119.9(2) . . ? N4 C15 C14 122.1(2) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.491 _refine_diff_density_min -0.691 _refine_diff_density_rms 0.113 data_c:\x-seed\k08adb01\maxus\k08adb01 _database_code_depnum_ccdc_archive 'CCDC 883182' #TrackingRef 'k08adb01.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H40 Co N10 O12' _chemical_formula_weight 791.65 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' Co Co 0.3494 0.9721 '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 7.4020(2) _cell_length_b 8.8340(2) _cell_length_c 14.0560(4) _cell_angle_alpha 90.328(1) _cell_angle_beta 104.437(1) _cell_angle_gamma 101.866(2) _cell_volume 869.49(4) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8890 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description Block _exptl_crystal_colour Pale-pink _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 413 _exptl_absorpt_coefficient_mu 0.571 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.94 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11613 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 27.45 _reflns_number_total 3930 _reflns_number_gt 3532 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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^)+(0.0207P)^2^+0.4164P] 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 SHELXL _refine_ls_extinction_coef 0.009(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3930 _refine_ls_number_parameters 257 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0783 _refine_ls_wR_factor_gt 0.0748 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.118 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.0000 0.0000 0.0000 0.01491(10) Uani 1 2 d S . . O1 O 0.17092(16) -0.16082(13) 0.01523(8) 0.0228(3) Uani 1 1 d D . . O2 O -0.06499(15) -0.05404(12) 0.13624(7) 0.0204(2) Uani 1 1 d D . . O3 O 0.33917(16) -0.24079(13) 0.18832(8) 0.0240(3) Uani 1 1 d . . . O4 O 0.2895(2) -0.35558(17) 0.31765(10) 0.0467(4) Uani 1 1 d . . . O5 O 0.07220(19) -0.40451(16) 0.18036(12) 0.0437(4) Uani 1 1 d . . . O6 O 0.93332(18) 0.60796(14) 0.37582(9) 0.0280(3) Uani 1 1 d D . . N1 N 0.23783(18) 0.17265(14) 0.08261(9) 0.0168(3) Uani 1 1 d . . . N2 N 0.73264(19) 0.30342(15) 0.38789(9) 0.0215(3) Uani 1 1 d . . . N3 N 0.80028(19) 0.22201(15) 0.46415(10) 0.0213(3) Uani 1 1 d . . . H3 H 0.8866 0.2637 0.5179 0.026 Uiso 1 1 calc R . . N4 N 0.91171(19) -0.10205(16) 0.68710(9) 0.0208(3) Uani 1 1 d . . . N5 N 0.2319(2) -0.33504(16) 0.22920(11) 0.0260(3) Uani 1 1 d . . . C1 C 0.2015(3) -0.2569(2) -0.05863(13) 0.0297(4) Uani 1 1 d . . . H1A H 0.1312 -0.3633 -0.0569 0.045 Uiso 1 1 calc R . . H1B H 0.3381 -0.2555 -0.0463 0.045 Uiso 1 1 calc R . . H1C H 0.1561 -0.2180 -0.1235 0.045 Uiso 1 1 calc R . . C2 C -0.2477(3) -0.1294(2) 0.14958(14) 0.0324(4) Uani 1 1 d . . . H2A H -0.3484 -0.1170 0.0918 0.049 Uiso 1 1 calc R . . H2B H -0.2684 -0.0827 0.2083 0.049 Uiso 1 1 calc R . . H2C H -0.2508 -0.2399 0.1577 0.049 Uiso 1 1 calc R . . C3 C 0.2656(2) 0.32097(18) 0.05799(11) 0.0190(3) Uani 1 1 d . . . H3A H 0.1846 0.3476 -0.0004 0.023 Uiso 1 1 calc R . . C4 C 0.4082(2) 0.43629(18) 0.11487(12) 0.0209(3) Uani 1 1 d . . . H4 H 0.4267 0.5394 0.0944 0.025 Uiso 1 1 calc R . . C5 C 0.5236(2) 0.40027(18) 0.20174(12) 0.0205(3) Uani 1 1 d . . . H5 H 0.6197 0.4788 0.2423 0.025 Uiso 1 1 calc R . . C6 C 0.4971(2) 0.24715(17) 0.22896(11) 0.0171(3) Uani 1 1 d . . . C7 C 0.3538(2) 0.13789(18) 0.16572(11) 0.0170(3) Uani 1 1 d . . . H7 H 0.3372 0.0327 0.1823 0.020 Uiso 1 1 calc R . . C8 C 0.6061(2) 0.19839(17) 0.32154(11) 0.0170(3) Uani 1 1 d . . . C9 C 0.5942(2) 0.04925(18) 0.35668(11) 0.0178(3) Uani 1 1 d . . . H9 H 0.5159 -0.0449 0.3240 0.021 Uiso 1 1 calc R . . C10 C 0.7205(2) 0.06834(18) 0.44885(11) 0.0181(3) Uani 1 1 d . . . C11 C 0.7659(2) -0.04608(18) 0.52128(11) 0.0178(3) Uani 1 1 d . . . C12 C 0.6986(2) -0.20467(19) 0.49689(12) 0.0227(3) Uani 1 1 d . . . H12 H 0.6247 -0.2405 0.4323 0.027 Uiso 1 1 calc R . . C13 C 0.7407(2) -0.30896(19) 0.56770(12) 0.0244(4) Uani 1 1 d . . . H13 H 0.6970 -0.4172 0.5521 0.029 Uiso 1 1 calc R . . C14 C 0.8471(2) -0.25374(19) 0.66153(12) 0.0225(3) Uani 1 1 d . . . H14 H 0.8755 -0.3262 0.7098 0.027 Uiso 1 1 calc R . . C15 C 0.8705(2) -0.00247(18) 0.61714(11) 0.0204(3) Uani 1 1 d . . . H15 H 0.9162 0.1052 0.6347 0.024 Uiso 1 1 calc R . . H2 H -0.0068 0.0045 0.1970 0.045(6) Uiso 1 1 d RD . . H1 H 0.219(3) -0.196(2) 0.0742(8) 0.047(6) Uiso 1 1 d D . . H6B H 1.008(3) 0.589(3) 0.3375(16) 0.062(8) Uiso 1 1 d D . . H6A H 0.870(3) 0.5130(12) 0.3844(17) 0.049(7) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.01502(17) 0.01488(16) 0.01282(16) -0.00002(10) 0.00066(11) 0.00224(11) O1 0.0283(6) 0.0243(6) 0.0162(6) -0.0009(5) 0.0009(5) 0.0128(5) O2 0.0205(6) 0.0231(6) 0.0147(5) -0.0008(4) 0.0042(4) -0.0014(4) O3 0.0249(6) 0.0205(6) 0.0241(6) 0.0042(5) 0.0046(5) 0.0010(5) O4 0.0653(10) 0.0459(9) 0.0252(7) 0.0117(6) 0.0122(7) 0.0029(7) O5 0.0260(7) 0.0335(8) 0.0621(10) 0.0037(7) 0.0035(7) -0.0054(6) O6 0.0299(7) 0.0232(6) 0.0250(6) -0.0023(5) 0.0048(5) -0.0043(5) N1 0.0171(7) 0.0168(6) 0.0150(6) 0.0001(5) 0.0016(5) 0.0033(5) N2 0.0208(7) 0.0204(7) 0.0176(7) 0.0020(5) -0.0008(5) -0.0010(5) N3 0.0205(7) 0.0206(7) 0.0162(6) 0.0015(5) -0.0027(5) -0.0016(5) N4 0.0210(7) 0.0242(7) 0.0159(6) 0.0023(5) 0.0034(5) 0.0034(5) N5 0.0318(8) 0.0179(7) 0.0298(8) 0.0014(6) 0.0103(6) 0.0054(6) C1 0.0380(10) 0.0310(10) 0.0241(9) -0.0026(7) 0.0074(8) 0.0172(8) C2 0.0262(9) 0.0396(11) 0.0270(9) -0.0071(8) 0.0115(8) -0.0079(8) C3 0.0208(8) 0.0179(7) 0.0175(7) 0.0025(6) 0.0024(6) 0.0054(6) C4 0.0242(8) 0.0147(7) 0.0225(8) 0.0010(6) 0.0044(7) 0.0030(6) C5 0.0203(8) 0.0171(7) 0.0205(8) -0.0028(6) 0.0014(6) 0.0007(6) C6 0.0162(7) 0.0192(8) 0.0155(7) 0.0002(6) 0.0041(6) 0.0030(6) C7 0.0174(8) 0.0159(7) 0.0164(7) 0.0013(6) 0.0033(6) 0.0024(6) C8 0.0154(7) 0.0184(7) 0.0158(7) -0.0004(6) 0.0025(6) 0.0023(6) C9 0.0161(7) 0.0190(7) 0.0163(7) -0.0014(6) 0.0015(6) 0.0024(6) C10 0.0161(8) 0.0187(8) 0.0183(8) 0.0000(6) 0.0040(6) 0.0021(6) C11 0.0151(7) 0.0213(8) 0.0171(7) 0.0009(6) 0.0042(6) 0.0040(6) C12 0.0242(9) 0.0220(8) 0.0188(8) -0.0018(6) 0.0012(7) 0.0032(6) C13 0.0286(9) 0.0198(8) 0.0229(8) 0.0003(6) 0.0044(7) 0.0037(7) C14 0.0249(9) 0.0229(8) 0.0207(8) 0.0050(6) 0.0069(7) 0.0062(6) C15 0.0201(8) 0.0203(8) 0.0191(8) -0.0001(6) 0.0037(6) 0.0024(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 2.0670(11) 2 ? Co1 O1 2.0670(11) . ? Co1 O2 2.1218(10) . ? Co1 O2 2.1218(10) 2 ? Co1 N1 2.1517(12) 2 ? Co1 N1 2.1517(12) . ? O1 C1 1.4268(19) . ? O1 H1 0.900(3) . ? O2 C2 1.4367(19) . ? O2 H2 0.9499 . ? O3 N5 1.2708(18) . ? O4 N5 1.2371(19) . ? O5 N5 1.240(2) . ? O6 H6B 0.898(3) . ? O6 H6A 0.899(3) . ? N1 C3 1.3449(19) . ? N1 C7 1.3449(19) . ? N2 C8 1.3434(19) . ? N2 N3 1.3439(18) . ? N3 C10 1.357(2) . ? N3 H3 0.8800 . ? N4 C14 1.341(2) . ? N4 C15 1.343(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.385(2) . ? C3 H3A 0.9500 . ? C4 C5 1.385(2) . ? C4 H4 0.9500 . ? C5 C6 1.396(2) . ? C5 H5 0.9500 . ? C6 C7 1.395(2) . ? C6 C8 1.468(2) . ? C7 H7 0.9500 . ? C8 C9 1.403(2) . ? C9 C10 1.382(2) . ? C9 H9 0.9500 . ? C10 C11 1.467(2) . ? C11 C15 1.384(2) . ? C11 C12 1.397(2) . ? C12 C13 1.382(2) . ? C12 H12 0.9500 . ? C13 C14 1.384(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? 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 Co1 O1 180.00(5) 2 . ? O1 Co1 O2 88.71(4) 2 . ? O1 Co1 O2 91.29(4) . . ? O1 Co1 O2 91.29(4) 2 2 ? O1 Co1 O2 88.71(4) . 2 ? O2 Co1 O2 180.00(9) . 2 ? O1 Co1 N1 90.34(5) 2 2 ? O1 Co1 N1 89.66(5) . 2 ? O2 Co1 N1 93.24(4) . 2 ? O2 Co1 N1 86.76(4) 2 2 ? O1 Co1 N1 89.66(5) 2 . ? O1 Co1 N1 90.34(5) . . ? O2 Co1 N1 86.76(4) . . ? O2 Co1 N1 93.24(4) 2 . ? N1 Co1 N1 180.00(6) 2 . ? C1 O1 Co1 129.23(10) . . ? C1 O1 H1 107.8(15) . . ? Co1 O1 H1 121.7(15) . . ? C2 O2 Co1 126.30(10) . . ? C2 O2 H2 102.4 . . ? Co1 O2 H2 125.4 . . ? H6B O6 H6A 104(2) . . ? C3 N1 C7 117.81(13) . . ? C3 N1 Co1 121.36(10) . . ? C7 N1 Co1 120.58(10) . . ? C8 N2 N3 105.27(12) . . ? N2 N3 C10 112.38(13) . . ? N2 N3 H3 123.8 . . ? C10 N3 H3 123.8 . . ? C14 N4 C15 117.34(13) . . ? O4 N5 O5 121.13(15) . . ? O4 N5 O3 119.00(15) . . ? O5 N5 O3 119.87(15) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 H2A 109.5 . . ? O2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? O2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C4 122.22(14) . . ? N1 C3 H3A 118.9 . . ? C4 C3 H3A 118.9 . . ? C5 C4 C3 119.57(15) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 119.20(14) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C7 C6 C5 117.28(14) . . ? C7 C6 C8 119.31(14) . . ? C5 C6 C8 123.35(14) . . ? N1 C7 C6 123.86(14) . . ? N1 C7 H7 118.1 . . ? C6 C7 H7 118.1 . . ? N2 C8 C9 110.64(13) . . ? N2 C8 C6 120.55(13) . . ? C9 C8 C6 128.76(14) . . ? C10 C9 C8 105.37(13) . . ? C10 C9 H9 127.3 . . ? C8 C9 H9 127.3 . . ? N3 C10 C9 106.33(14) . . ? N3 C10 C11 123.55(14) . . ? C9 C10 C11 130.12(14) . . ? C15 C11 C12 117.08(14) . . ? C15 C11 C10 121.91(14) . . ? C12 C11 C10 120.97(14) . . ? C13 C12 C11 119.35(15) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 119.20(15) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? N4 C14 C13 122.62(15) . . ? N4 C14 H14 118.7 . . ? C13 C14 H14 118.7 . . ? N4 C15 C11 124.41(14) . . ? N4 C15 H15 117.8 . . ? C11 C15 H15 117.8 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.364 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.081