# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Fu Fu' _publ_contact_author_email 'WF FU@YAHOO.COM.CN' _publ_section_title ; A novel Kolbe reaction pathway for a selective one- and two-electron reduction of azo compounds ; loop_ _publ_author_name 'Fu Fu' 'Xin Gan' 'Hui-Fang Jie Li' 'Li Li' 'De-Hui Wang' 'Liang-Jun Zhou' data_080415a _database_code_depnum_ccdc_archive 'CCDC 664375' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H32 Cl2 N6 O9 Zn4' _chemical_formula_weight 940.99 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' 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 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 22.926(3) _cell_length_b 12.2830(17) _cell_length_c 26.975(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.015(2) _cell_angle_gamma 90.00 _cell_volume 7370.0(15) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2791 _cell_measurement_theta_min 2.589 _cell_measurement_theta_max 25.229 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.696 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3792 _exptl_absorpt_coefficient_mu 2.774 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5934 _exptl_absorpt_correction_T_max 0.8737 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19045 _diffrn_reflns_av_R_equivalents 0.0876 _diffrn_reflns_av_sigmaI/netI 0.1136 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.01 _reflns_number_total 6509 _reflns_number_gt 3346 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.0000P] 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 6509 _refine_ls_number_parameters 564 _refine_ls_number_restraints 180 _refine_ls_R_factor_all 0.1217 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1138 _refine_ls_wR_factor_gt 0.0967 _refine_ls_goodness_of_fit_ref 0.886 _refine_ls_restrained_S_all 0.893 _refine_ls_shift/su_max 0.005 _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 0.15587(3) 0.36377(6) 0.54104(3) 0.0416(2) Uani 1 1 d . A . Zn2 Zn 0.30147(4) 0.37747(6) 0.58409(3) 0.0455(2) Uani 1 1 d . . . Zn3 Zn 0.23332(4) 0.36762(6) 0.66156(3) 0.0481(2) Uani 1 1 d . A . Zn4 Zn 0.20503(4) 0.57898(6) 0.59853(3) 0.0548(3) Uani 1 1 d . . . N1 N 0.0814(2) 0.2552(4) 0.6074(2) 0.0510(15) Uani 1 1 d . . . N2 N 0.1222(2) 0.2175(4) 0.53995(18) 0.0382(13) Uani 1 1 d . . . N3 N 0.2326(2) 0.2055(4) 0.66095(19) 0.0461(14) Uani 1 1 d . . . N4 N 0.2746(2) 0.2057(4) 0.58998(18) 0.0376(13) Uani 1 1 d . . . N5 N 0.1657(2) 0.1894(4) 0.47109(18) 0.0378(13) Uani 1 1 d . . . N6 N 0.1811(2) 0.2993(4) 0.48034(18) 0.0381(13) Uani 1 1 d . A . O9 O 0.22120(18) 0.4256(3) 0.59275(14) 0.0418(11) Uani 1 1 d . A . C1 C 0.0896(3) 0.1799(6) 0.5731(2) 0.0458(18) Uani 1 1 d . A . C2 C 0.1341(3) 0.1509(5) 0.5037(2) 0.0412(16) Uani 1 1 d . A . C3 C 0.1131(3) 0.0415(5) 0.5000(3) 0.0518(19) Uani 1 1 d . . . H3 H 0.1213 -0.0045 0.4751 0.062 Uiso 1 1 calc R A . C4 C 0.0817(3) 0.0051(5) 0.5321(3) 0.054(2) Uani 1 1 d . A . H4 H 0.0683 -0.0666 0.5292 0.065 Uiso 1 1 calc R . . C5 C 0.0679(3) 0.0719(6) 0.5708(3) 0.0479(18) Uani 1 1 d . . . C6 C 0.0355(3) 0.0418(6) 0.6070(3) 0.058(2) Uani 1 1 d . A . C7 C 0.0263(3) 0.1183(7) 0.6402(3) 0.069(2) Uani 1 1 d . . . H7 H 0.0044 0.1002 0.6639 0.083 Uiso 1 1 calc R A . C8 C 0.0486(3) 0.2234(7) 0.6398(3) 0.061(2) Uani 1 1 d . A . C9 C 0.0116(4) -0.0736(6) 0.6079(3) 0.086(3) Uani 1 1 d . . . H9A H -0.0211 -0.0738 0.6244 0.129 Uiso 1 1 calc R A . H9B H 0.0431 -0.1202 0.6262 0.129 Uiso 1 1 calc R . . H9C H -0.0024 -0.0997 0.5735 0.129 Uiso 1 1 calc R . . C10 C 0.0380(4) 0.3097(7) 0.6764(3) 0.090(3) Uani 1 1 d . . . H10A H 0.0749 0.3246 0.7011 0.135 Uiso 1 1 calc R A . H10B H 0.0084 0.2845 0.6935 0.135 Uiso 1 1 calc R . . H10C H 0.0238 0.3750 0.6578 0.135 Uiso 1 1 calc R . . C11 C 0.2471(3) 0.1473(5) 0.6214(2) 0.0406(16) Uani 1 1 d . A . C12 C 0.2096(3) 0.3486(5) 0.4489(2) 0.0376(16) Uani 1 1 d . . . C13 C 0.2215(3) 0.4623(5) 0.4567(2) 0.0461(18) Uani 1 1 d . A . H13 H 0.2103 0.4978 0.4834 0.055 Uiso 1 1 calc R . . C14 C 0.2484(3) 0.5179(5) 0.4262(2) 0.0483(18) Uani 1 1 d . . . H14 H 0.2568 0.5915 0.4320 0.058 Uiso 1 1 calc R A . C15 C 0.2355(3) 0.0358(5) 0.6158(2) 0.0437(17) Uani 1 1 d . . . C16 C 0.2079(3) -0.0178(6) 0.6502(3) 0.054(2) Uani 1 1 d . A . C17 C 0.1974(3) 0.0417(6) 0.6898(3) 0.059(2) Uani 1 1 d . . . H17 H 0.1809 0.0069 0.7138 0.071 Uiso 1 1 calc R A . C18 C 0.2099(3) 0.1487(6) 0.6955(2) 0.054(2) Uani 1 1 d . A . C19 C 0.1914(4) -0.1350(6) 0.6438(3) 0.076(2) Uani 1 1 d . . . H19A H 0.1708 -0.1560 0.6694 0.114 Uiso 1 1 calc R A . H19B H 0.2271 -0.1780 0.6475 0.114 Uiso 1 1 calc R . . H19C H 0.1655 -0.1466 0.6105 0.114 Uiso 1 1 calc R . . C20 C 0.1982(4) 0.2130(6) 0.7402(2) 0.074(2) Uani 1 1 d . . . H20A H 0.1867 0.1641 0.7639 0.111 Uiso 1 1 calc R A . H20B H 0.1665 0.2644 0.7279 0.111 Uiso 1 1 calc R . . H20C H 0.2341 0.2511 0.7570 0.111 Uiso 1 1 calc R . . O1 O 0.0958(2) 0.4793(4) 0.51491(18) 0.0604(13) Uani 1 1 d . . . O2 O 0.1377(3) 0.6335(4) 0.5462(2) 0.0803(17) Uani 1 1 d . A . C21 C 0.0956(4) 0.5807(7) 0.5187(3) 0.058(2) Uani 1 1 d . A . C22 C 0.0420(3) 0.6394(6) 0.4872(3) 0.087(3) Uani 1 1 d . . . H22A H 0.0505 0.7159 0.4872 0.130 Uiso 1 1 calc R A . H22B H 0.0080 0.6275 0.5014 0.130 Uiso 1 1 calc R . . H22C H 0.0332 0.6124 0.4528 0.130 Uiso 1 1 calc R . . O3 O 0.3655(10) 0.400(2) 0.6434(6) 0.055(6) Uani 0.45(4) 1 d PDU A 1 O4 O 0.3124(7) 0.429(2) 0.6999(8) 0.039(5) Uani 0.45(4) 1 d PDU A 1 C23 C 0.3606(7) 0.418(3) 0.6873(7) 0.055(9) Uani 0.45(4) 1 d PDU A 1 C24 C 0.4172(7) 0.449(3) 0.7264(8) 0.073(8) Uani 0.45(4) 1 d PDU A 1 H24A H 0.4507 0.4100 0.7195 0.109 Uiso 0.45(4) 1 calc PR A 1 H24B H 0.4129 0.4303 0.7600 0.109 Uiso 0.45(4) 1 calc PR A 1 H24C H 0.4239 0.5257 0.7247 0.109 Uiso 0.45(4) 1 calc PR A 1 O3' O 0.3692(8) 0.3610(18) 0.6507(5) 0.047(4) Uani 0.55(4) 1 d PDU A 2 O4' O 0.3146(6) 0.3915(19) 0.7059(7) 0.058(5) Uani 0.55(4) 1 d PDU A 2 C23' C 0.3635(7) 0.384(2) 0.6941(5) 0.047(6) Uani 0.55(4) 1 d PDU A 2 C24' C 0.4197(6) 0.386(3) 0.7363(6) 0.068(7) Uani 0.55(4) 1 d PDU A 2 H24D H 0.4141 0.3421 0.7641 0.102 Uiso 0.55(4) 1 calc PR A 2 H24E H 0.4283 0.4597 0.7478 0.102 Uiso 0.55(4) 1 calc PR A 2 H24F H 0.4526 0.3581 0.7239 0.102 Uiso 0.55(4) 1 calc PR A 2 O5 O 0.1832(2) 0.4460(4) 0.69846(18) 0.0661(15) Uani 1 1 d . . . O6 O 0.1784(3) 0.6062(4) 0.6613(2) 0.0796(18) Uani 1 1 d . A . C25 C 0.1693(3) 0.5461(7) 0.6945(3) 0.061(2) Uani 1 1 d . A . C26 C 0.1396(4) 0.5908(7) 0.7345(3) 0.089(3) Uani 1 1 d . . . H26A H 0.1492 0.6666 0.7399 0.134 Uiso 1 1 calc R A . H26B H 0.1539 0.5517 0.7660 0.134 Uiso 1 1 calc R . . H26C H 0.0968 0.5823 0.7231 0.134 Uiso 1 1 calc R . . O7 O 0.3314(8) 0.5452(9) 0.5866(7) 0.070(3) Uani 0.58(3) 1 d PDU A 1 O8 O 0.2653(5) 0.6805(10) 0.5874(8) 0.068(4) Uani 0.58(3) 1 d PDU A 1 C27 C 0.3144(7) 0.6435(10) 0.5843(9) 0.075(3) Uani 0.58(3) 1 d PDU A 1 C28 C 0.3584(7) 0.7258(11) 0.5723(10) 0.090(6) Uani 0.58(3) 1 d PDU A 1 H28A H 0.3460 0.7462 0.5369 0.135 Uiso 0.58(3) 1 calc PR A 1 H28B H 0.3978 0.6941 0.5790 0.135 Uiso 0.58(3) 1 calc PR A 1 H28C H 0.3592 0.7891 0.5933 0.135 Uiso 0.58(3) 1 calc PR A 1 O7' O 0.3154(10) 0.5600(17) 0.5679(9) 0.070(3) Uani 0.42(3) 1 d PDU A 2 O8' O 0.2751(8) 0.6714(16) 0.6136(8) 0.063(6) Uani 0.42(3) 1 d PDU A 2 C27' C 0.3157(9) 0.6444(18) 0.5937(12) 0.075(3) Uani 0.42(3) 1 d PDU A 2 C28' C 0.3713(9) 0.7146(19) 0.6051(12) 0.092(9) Uani 0.42(3) 1 d PDU A 2 H28D H 0.3657 0.7750 0.6261 0.139 Uiso 0.42(3) 1 calc PR A 2 H28E H 0.3786 0.7412 0.5737 0.139 Uiso 0.42(3) 1 calc PR A 2 H28F H 0.4052 0.6722 0.6229 0.139 Uiso 0.42(3) 1 calc PR A 2 C29 C 0.0568(5) 0.3732(14) 0.3930(5) 0.103(6) Uani 0.672(4) 1 d PDU B 1 H29A H 0.0710 0.4113 0.4252 0.123 Uiso 0.672(4) 1 calc PR B 1 H29B H 0.0735 0.3004 0.3969 0.123 Uiso 0.672(4) 1 calc PR B 1 Cl1 Cl -0.0206(4) 0.3655(9) 0.3786(3) 0.146(2) Uani 0.672(4) 1 d PDU B 1 Cl2 Cl 0.0809(4) 0.4405(7) 0.3458(3) 0.177(3) Uani 0.672(4) 1 d PDU B 1 C29' C 0.0513(12) 0.346(3) 0.3753(9) 0.047(12) Uani 0.210(6) 1 d PDU C 2 H29C H 0.0848 0.3917 0.3921 0.057 Uiso 0.210(6) 1 calc PR C 2 H29D H 0.0614 0.2709 0.3848 0.057 Uiso 0.210(6) 1 calc PR C 2 Cl1' Cl -0.0129(15) 0.383(3) 0.3939(10) 0.146(2) Uani 0.210(6) 1 d PDU C 2 Cl2' Cl 0.0379(13) 0.361(2) 0.3098(9) 0.214(10) Uani 0.210(6) 1 d PDU C 2 C29" C 0.0750(13) 0.358(2) 0.343(2) 0.037(15) Uani 0.117(4) 1 d PDU D 3 H29E H 0.0846 0.3469 0.3101 0.044 Uiso 0.117(4) 1 calc PR D 3 H29F H 0.0993 0.3080 0.3674 0.044 Uiso 0.117(4) 1 calc PR D 3 Cl1" Cl -0.0001(11) 0.333(2) 0.3376(13) 0.146(2) Uani 0.117(4) 1 d PDU D 3 Cl2" Cl 0.0903(13) 0.490(2) 0.3629(12) 0.096(9) Uani 0.117(4) 1 d PDU D 3 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 0.0439(5) 0.0390(5) 0.0456(4) -0.0032(4) 0.0182(4) -0.0015(4) Zn2 0.0451(5) 0.0484(5) 0.0472(5) -0.0062(4) 0.0193(4) -0.0009(4) Zn3 0.0526(6) 0.0514(5) 0.0451(5) -0.0046(4) 0.0213(4) 0.0003(4) Zn4 0.0585(6) 0.0390(5) 0.0713(6) -0.0088(4) 0.0240(5) -0.0027(4) N1 0.051(4) 0.059(4) 0.051(4) 0.004(3) 0.027(3) 0.001(3) N2 0.037(4) 0.043(3) 0.039(3) 0.003(3) 0.017(3) -0.002(3) N3 0.051(4) 0.054(4) 0.037(3) 0.005(3) 0.019(3) 0.003(3) N4 0.037(3) 0.040(3) 0.040(3) 0.006(2) 0.016(3) -0.001(3) N5 0.040(4) 0.033(3) 0.042(3) -0.002(2) 0.012(3) -0.004(3) N6 0.040(4) 0.033(3) 0.046(3) 0.005(2) 0.019(3) -0.004(2) O9 0.045(3) 0.036(2) 0.048(3) -0.003(2) 0.018(2) 0.000(2) C1 0.038(5) 0.056(5) 0.048(4) 0.000(4) 0.017(4) -0.005(4) C2 0.038(4) 0.046(4) 0.042(4) 0.000(3) 0.015(3) -0.006(3) C3 0.059(5) 0.045(4) 0.055(5) -0.005(3) 0.022(4) -0.009(4) C4 0.063(5) 0.046(4) 0.058(5) 0.002(4) 0.022(4) -0.013(4) C5 0.043(5) 0.054(5) 0.049(4) 0.002(4) 0.017(4) -0.001(4) C6 0.051(5) 0.071(5) 0.058(5) 0.013(4) 0.023(4) -0.012(4) C7 0.064(6) 0.088(7) 0.067(5) 0.011(5) 0.039(5) -0.008(5) C8 0.054(6) 0.086(6) 0.051(5) 0.004(4) 0.026(4) 0.005(5) C9 0.094(7) 0.089(6) 0.086(6) 0.017(5) 0.042(6) -0.029(6) C10 0.092(8) 0.107(7) 0.084(6) -0.018(5) 0.047(6) 0.001(6) C11 0.034(4) 0.047(4) 0.043(4) 0.005(3) 0.013(3) 0.005(3) C12 0.041(4) 0.035(4) 0.041(4) 0.004(3) 0.018(3) 0.001(3) C13 0.055(5) 0.040(4) 0.050(4) 0.000(3) 0.025(4) -0.001(3) C14 0.049(5) 0.040(4) 0.059(5) 0.002(4) 0.020(4) 0.000(3) C15 0.049(5) 0.038(4) 0.048(4) 0.008(3) 0.021(4) -0.001(3) C16 0.064(6) 0.044(5) 0.059(5) 0.011(4) 0.022(4) 0.010(4) C17 0.069(6) 0.055(5) 0.064(5) 0.019(4) 0.037(5) 0.005(4) C18 0.067(5) 0.064(5) 0.038(4) 0.011(4) 0.027(4) 0.010(4) C19 0.102(7) 0.051(5) 0.090(6) 0.011(4) 0.054(5) -0.011(5) C20 0.099(7) 0.086(6) 0.045(5) 0.007(4) 0.032(5) 0.004(5) O1 0.045(3) 0.048(3) 0.084(4) 0.002(3) 0.009(3) 0.010(3) O2 0.080(4) 0.047(3) 0.103(4) -0.001(3) 0.003(4) -0.001(3) C21 0.062(6) 0.050(5) 0.069(5) 0.011(4) 0.029(5) 0.007(5) C22 0.056(6) 0.074(6) 0.119(7) 0.032(5) -0.001(5) 0.019(5) O3 0.052(8) 0.060(10) 0.056(8) 0.001(7) 0.020(6) 0.005(7) O4 0.043(8) 0.040(9) 0.039(7) -0.012(6) 0.020(5) -0.004(5) C23 0.055(11) 0.046(12) 0.060(11) -0.008(8) 0.007(8) -0.002(7) C24 0.066(11) 0.084(12) 0.064(10) -0.004(8) 0.009(8) 0.004(8) O3' 0.043(6) 0.050(8) 0.045(6) -0.005(5) 0.007(5) 0.002(6) O4' 0.071(8) 0.053(9) 0.051(7) 0.002(6) 0.017(5) 0.001(6) C23' 0.058(9) 0.037(9) 0.047(8) 0.001(7) 0.014(7) -0.009(6) C24' 0.058(9) 0.082(11) 0.061(8) -0.006(7) 0.011(7) -0.005(7) O5 0.079(4) 0.061(4) 0.070(3) -0.003(3) 0.042(3) 0.006(3) O6 0.124(5) 0.048(3) 0.085(4) -0.012(3) 0.060(4) 0.004(3) C25 0.055(6) 0.068(6) 0.068(6) -0.022(5) 0.028(5) -0.004(4) C26 0.101(7) 0.094(7) 0.089(6) -0.026(5) 0.055(6) 0.005(5) O7 0.071(6) 0.059(4) 0.090(7) 0.000(5) 0.039(5) -0.008(4) O8 0.065(7) 0.048(6) 0.095(9) 0.004(6) 0.027(6) -0.004(5) C27 0.073(5) 0.057(5) 0.101(7) -0.007(5) 0.033(5) -0.009(4) C28 0.079(9) 0.077(9) 0.115(11) 0.012(7) 0.024(8) -0.019(7) O7' 0.071(6) 0.059(4) 0.090(7) 0.000(5) 0.039(5) -0.008(4) O8' 0.070(9) 0.060(8) 0.068(9) -0.017(7) 0.036(7) -0.002(6) C27' 0.073(5) 0.057(5) 0.101(7) -0.007(5) 0.033(5) -0.009(4) C28' 0.090(12) 0.084(12) 0.104(13) -0.002(9) 0.025(9) -0.006(8) C29 0.087(9) 0.120(10) 0.096(9) 0.001(8) 0.011(8) -0.005(7) Cl1 0.127(4) 0.156(4) 0.160(5) 0.007(4) 0.042(4) 0.009(3) Cl2 0.156(6) 0.201(7) 0.190(7) 0.032(6) 0.074(5) 0.015(5) C29' 0.042(14) 0.048(14) 0.047(14) -0.001(9) 0.002(9) 0.001(9) Cl1' 0.127(4) 0.156(4) 0.160(5) 0.007(4) 0.042(4) 0.009(3) Cl2' 0.209(13) 0.242(14) 0.211(13) 0.002(9) 0.092(10) 0.007(9) C29" 0.030(17) 0.040(17) 0.037(17) -0.011(10) 0.001(10) 0.002(10) Cl1" 0.127(4) 0.156(4) 0.160(5) 0.007(4) 0.042(4) 0.009(3) Cl2" 0.083(12) 0.084(12) 0.106(12) -0.014(8) -0.003(8) -0.004(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 O9 1.937(4) . ? Zn1 N2 1.953(5) . ? Zn1 O1 1.985(5) . ? Zn1 N6 2.025(5) . ? Zn1 Zn4 3.1331(11) . ? Zn2 O3 1.911(17) . ? Zn2 N5 2.000(5) 7_556 ? Zn2 O9 2.000(4) . ? Zn2 O3' 2.081(15) . ? Zn2 O7 2.168(12) . ? Zn2 N4 2.214(5) . ? Zn2 O7' 2.32(2) . ? Zn2 Zn3 2.8991(10) . ? Zn3 O9 1.944(4) . ? Zn3 O5 1.947(5) . ? Zn3 O4' 1.977(15) . ? Zn3 N3 1.991(5) . ? Zn3 O4 2.002(16) . ? Zn3 Zn4 3.0850(11) . ? Zn4 O8' 1.927(16) . ? Zn4 O9 1.934(4) . ? Zn4 O8 1.937(12) . ? Zn4 O2 1.942(6) . ? Zn4 O6 1.963(5) . ? N1 C8 1.341(8) . ? N1 C1 1.354(8) . ? N2 C2 1.354(7) . ? N2 C1 1.376(7) . ? N3 C18 1.365(7) . ? N3 C11 1.389(7) . ? N4 C12 1.364(7) 7_556 ? N4 C11 1.376(7) . ? N5 C2 1.352(7) . ? N5 N6 1.402(6) . ? N5 Zn2 1.999(5) 7_556 ? N6 C12 1.335(7) . ? C1 C5 1.413(9) . ? C2 C3 1.423(8) . ? C3 C4 1.332(8) . ? C3 H3 0.9300 . ? C4 C5 1.423(8) . ? C4 H4 0.9300 . ? C5 C6 1.412(8) . ? C6 C7 1.349(9) . ? C6 C9 1.523(9) . ? C7 C8 1.390(10) . ? C7 H7 0.9300 . ? C8 C10 1.508(9) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C15 1.396(8) . ? C12 N4 1.364(7) 7_556 ? C12 C13 1.429(8) . ? C13 C14 1.332(8) . ? C13 H13 0.9300 . ? C14 C15 1.435(8) 7_556 ? C14 H14 0.9300 . ? C15 C16 1.405(8) . ? C15 C14 1.435(8) 7_556 ? C16 C17 1.364(9) . ? C16 C19 1.487(9) . ? C17 C18 1.346(9) . ? C17 H17 0.9300 . ? C18 C20 1.517(8) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? O1 C21 1.250(8) . ? O2 C21 1.248(9) . ? C21 C22 1.498(10) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? O3 C23 1.238(9) . ? O4 C23 1.239(9) . ? C23 C24 1.508(9) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? O3' C23' 1.242(8) . ? O4' C23' 1.241(9) . ? C23' C24' 1.498(9) . ? C24' H24D 0.9600 . ? C24' H24E 0.9600 . ? C24' H24F 0.9600 . ? O5 C25 1.269(8) . ? O6 C25 1.217(8) . ? C25 C26 1.511(9) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? O7 C27 1.266(9) . ? O8 C27 1.237(9) . ? C27 C28 1.516(9) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? O7' C27' 1.249(9) . ? O8' C27' 1.227(9) . ? C27' C28' 1.508(9) . ? C28' H28D 0.9600 . ? C28' H28E 0.9600 . ? C28' H28F 0.9600 . ? C29 Cl2 1.718(9) . ? C29 Cl1 1.723(9) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29' Cl2' 1.727(10) . ? C29' Cl1' 1.728(10) . ? C29' H29C 0.9700 . ? C29' H29D 0.9700 . ? C29" Cl1" 1.721(10) . ? C29" Cl2" 1.723(10) . ? C29" H29E 0.9700 . ? C29" H29F 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O9 Zn1 N2 127.24(18) . . ? O9 Zn1 O1 108.95(18) . . ? N2 Zn1 O1 114.5(2) . . ? O9 Zn1 N6 114.42(18) . . ? N2 Zn1 N6 79.47(19) . . ? O1 Zn1 N6 107.55(19) . . ? O9 Zn1 Zn4 35.94(11) . . ? N2 Zn1 Zn4 151.30(14) . . ? O1 Zn1 Zn4 73.02(14) . . ? N6 Zn1 Zn4 126.26(14) . . ? O3 Zn2 N5 109.3(7) . 7_556 ? O3 Zn2 O9 113.7(6) . . ? N5 Zn2 O9 136.98(18) 7_556 . ? O3 Zn2 O3' 14.0(8) . . ? N5 Zn2 O3' 105.4(5) 7_556 . ? O9 Zn2 O3' 116.3(5) . . ? O3 Zn2 O7 70.3(10) . . ? N5 Zn2 O7 103.9(4) 7_556 . ? O9 Zn2 O7 90.5(4) . . ? O3' Zn2 O7 84.3(8) . . ? O3 Zn2 N4 104.3(9) . . ? N5 Zn2 N4 79.82(19) 7_556 . ? O9 Zn2 N4 89.61(17) . . ? O3' Zn2 N4 90.4(6) . . ? O7 Zn2 N4 174.2(5) . . ? O3 Zn2 O7' 84.6(10) . . ? N5 Zn2 O7' 99.4(5) 7_556 . ? O9 Zn2 O7' 84.8(6) . . ? O3' Zn2 O7' 98.6(8) . . ? O7 Zn2 O7' 14.3(7) . . ? N4 Zn2 O7' 170.8(6) . . ? O3 Zn2 Zn3 80.9(6) . . ? N5 Zn2 Zn3 152.25(14) 7_556 . ? O9 Zn2 Zn3 41.94(11) . . ? O3' Zn2 Zn3 78.1(5) . . ? O7 Zn2 Zn3 103.8(4) . . ? N4 Zn2 Zn3 72.59(13) . . ? O7' Zn2 Zn3 107.4(5) . . ? O9 Zn3 O5 109.98(19) . . ? O9 Zn3 O4' 114.8(6) . . ? O5 Zn3 O4' 101.8(6) . . ? O9 Zn3 N3 111.04(18) . . ? O5 Zn3 N3 119.6(2) . . ? O4' Zn3 N3 99.1(7) . . ? O9 Zn3 O4 105.0(7) . . ? O5 Zn3 O4 97.1(5) . . ? O4' Zn3 O4 13.9(8) . . ? N3 Zn3 O4 112.5(7) . . ? O9 Zn3 Zn2 43.43(12) . . ? O5 Zn3 Zn2 146.69(15) . . ? O4' Zn3 Zn2 80.6(5) . . ? N3 Zn3 Zn2 92.31(15) . . ? O4 Zn3 Zn2 77.2(6) . . ? O9 Zn3 Zn4 37.19(11) . . ? O5 Zn3 Zn4 78.14(15) . . ? O4' Zn3 Zn4 104.5(7) . . ? N3 Zn3 Zn4 146.80(15) . . ? O4 Zn3 Zn4 90.7(8) . . ? Zn2 Zn3 Zn4 69.25(3) . . ? O8' Zn4 O9 115.1(6) . . ? O8' Zn4 O8 20.8(5) . . ? O9 Zn4 O8 117.2(4) . . ? O8' Zn4 O2 115.1(7) . . ? O9 Zn4 O2 114.3(2) . . ? O8 Zn4 O2 97.8(5) . . ? O8' Zn4 O6 97.7(6) . . ? O9 Zn4 O6 109.95(19) . . ? O8 Zn4 O6 114.0(6) . . ? O2 Zn4 O6 102.2(2) . . ? O8' Zn4 Zn3 109.0(7) . . ? O9 Zn4 Zn3 37.41(11) . . ? O8 Zn4 Zn3 124.4(4) . . ? O2 Zn4 Zn3 135.67(17) . . ? O6 Zn4 Zn3 74.66(15) . . ? O8' Zn4 Zn1 141.5(4) . . ? O9 Zn4 Zn1 36.01(12) . . ? O8 Zn4 Zn1 130.6(5) . . ? O2 Zn4 Zn1 78.69(16) . . ? O6 Zn4 Zn1 114.92(16) . . ? Zn3 Zn4 Zn1 64.23(3) . . ? C8 N1 C1 116.1(6) . . ? C2 N2 C1 120.2(5) . . ? C2 N2 Zn1 114.7(4) . . ? C1 N2 Zn1 125.0(4) . . ? C18 N3 C11 117.5(6) . . ? C18 N3 Zn3 120.6(4) . . ? C11 N3 Zn3 121.2(4) . . ? C12 N4 C11 117.8(5) 7_556 . ? C12 N4 Zn2 106.3(4) 7_556 . ? C11 N4 Zn2 135.9(4) . . ? C2 N5 N6 111.8(5) . . ? C2 N5 Zn2 134.2(4) . 7_556 ? N6 N5 Zn2 113.9(3) . 7_556 ? C12 N6 N5 117.6(5) . . ? C12 N6 Zn1 128.0(4) . . ? N5 N6 Zn1 114.3(3) . . ? Zn4 O9 Zn1 108.05(19) . . ? Zn4 O9 Zn3 105.40(17) . . ? Zn1 O9 Zn3 116.80(19) . . ? Zn4 O9 Zn2 119.8(2) . . ? Zn1 O9 Zn2 111.91(18) . . ? Zn3 O9 Zn2 94.63(17) . . ? N1 C1 N2 113.7(6) . . ? N1 C1 C5 124.4(6) . . ? N2 C1 C5 121.9(6) . . ? N5 C2 N2 119.5(6) . . ? N5 C2 C3 120.7(6) . . ? N2 C2 C3 119.8(6) . . ? C4 C3 C2 119.9(6) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 122.4(7) . . ? C3 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? C6 C5 C1 117.1(6) . . ? C6 C5 C4 127.2(7) . . ? C1 C5 C4 115.7(6) . . ? C7 C6 C5 118.0(7) . . ? C7 C6 C9 121.6(7) . . ? C5 C6 C9 120.4(7) . . ? C6 C7 C8 121.7(7) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? N1 C8 C7 122.7(7) . . ? N1 C8 C10 115.2(7) . . ? C7 C8 C10 122.0(7) . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N4 C11 N3 115.8(6) . . ? N4 C11 C15 123.3(6) . . ? N3 C11 C15 120.9(6) . . ? N6 C12 N4 121.9(5) . 7_556 ? N6 C12 C13 117.1(5) . . ? N4 C12 C13 120.9(5) 7_556 . ? C14 C13 C12 120.8(6) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 119.9(6) . 7_556 ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 7_556 . ? C11 C15 C16 119.6(6) . . ? C11 C15 C14 117.2(6) . 7_556 ? C16 C15 C14 123.2(6) . 7_556 ? C17 C16 C15 117.3(7) . . ? C17 C16 C19 121.4(7) . . ? C15 C16 C19 121.4(6) . . ? C18 C17 C16 122.7(7) . . ? C18 C17 H17 118.6 . . ? C16 C17 H17 118.6 . . ? C17 C18 N3 121.8(6) . . ? C17 C18 C20 121.7(6) . . ? N3 C18 C20 116.5(6) . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C21 O1 Zn1 134.4(5) . . ? C21 O2 Zn4 128.1(5) . . ? O2 C21 O1 123.3(8) . . ? O2 C21 C22 119.8(8) . . ? O1 C21 C22 116.9(8) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C23 O3 Zn2 126.7(15) . . ? C23 O4 Zn3 125.2(13) . . ? O3 C23 O4 125.1(16) . . ? O3 C23 C24 116.9(10) . . ? O4 C23 C24 117.1(10) . . ? C23' O3' Zn2 124.3(11) . . ? C23' O4' Zn3 127.8(13) . . ? O4' C23' O3' 124.4(13) . . ? O4' C23' C24' 117.9(9) . . ? O3' C23' C24' 116.9(9) . . ? C23' C24' H24D 109.5 . . ? C23' C24' H24E 109.5 . . ? H24D C24' H24E 109.5 . . ? C23' C24' H24F 109.5 . . ? H24D C24' H24F 109.5 . . ? H24E C24' H24F 109.5 . . ? C25 O5 Zn3 127.2(5) . . ? C25 O6 Zn4 132.6(5) . . ? O6 C25 O5 124.3(7) . . ? O6 C25 C26 119.6(8) . . ? O5 C25 C26 116.1(8) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C27 O7 Zn2 144.5(12) . . ? C27 O8 Zn4 118.0(10) . . ? O8 C27 O7 128.4(12) . . ? O8 C27 C28 115.7(10) . . ? O7 C27 C28 115.7(9) . . ? C27' O7' Zn2 133(2) . . ? C27' O8' Zn4 115.5(12) . . ? O8' C27' O7' 124.4(15) . . ? O8' C27' C28' 116.8(11) . . ? O7' C27' C28' 118.6(10) . . ? C27' C28' H28D 109.5 . . ? C27' C28' H28E 109.5 . . ? H28D C28' H28E 109.5 . . ? C27' C28' H28F 109.5 . . ? H28D C28' H28F 109.5 . . ? H28E C28' H28F 109.5 . . ? Cl2 C29 Cl1 110.9(7) . . ? Cl2 C29 H29A 109.5 . . ? Cl1 C29 H29A 109.5 . . ? Cl2 C29 H29B 109.5 . . ? Cl1 C29 H29B 109.5 . . ? H29A C29 H29B 108.0 . . ? Cl2' C29' Cl1' 108.4(9) . . ? Cl2' C29' H29C 110.0 . . ? Cl1' C29' H29C 110.0 . . ? Cl2' C29' H29D 110.0 . . ? Cl1' C29' H29D 110.0 . . ? H29C C29' H29D 108.4 . . ? Cl1" C29" Cl2" 108.4(9) . . ? Cl1" C29" H29E 110.0 . . ? Cl2" C29" H29E 110.0 . . ? Cl1" C29" H29F 110.0 . . ? Cl2" C29" H29F 110.0 . . ? H29E C29" H29F 108.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Zn2 Zn3 O9 142.0(9) . . . . ? N5 Zn2 Zn3 O9 -103.5(4) 7_556 . . . ? O3' Zn2 Zn3 O9 156.0(6) . . . . ? O7 Zn2 Zn3 O9 75.0(6) . . . . ? N4 Zn2 Zn3 O9 -109.8(2) . . . . ? O7' Zn2 Zn3 O9 60.6(6) . . . . ? O3 Zn2 Zn3 O5 96.6(9) . . . . ? N5 Zn2 Zn3 O5 -148.9(4) 7_556 . . . ? O9 Zn2 Zn3 O5 -45.4(3) . . . . ? O3' Zn2 Zn3 O5 110.6(7) . . . . ? O7 Zn2 Zn3 O5 29.6(6) . . . . ? N4 Zn2 Zn3 O5 -155.2(3) . . . . ? O7' Zn2 Zn3 O5 15.2(7) . . . . ? O3 Zn2 Zn3 O4' -0.5(7) . . . . ? N5 Zn2 Zn3 O4' 114.0(8) 7_556 . . . ? O9 Zn2 Zn3 O4' -142.5(7) . . . . ? O3' Zn2 Zn3 O4' 13.5(6) . . . . ? O7 Zn2 Zn3 O4' -67.5(9) . . . . ? N4 Zn2 Zn3 O4' 107.7(7) . . . . ? O7' Zn2 Zn3 O4' -81.9(9) . . . . ? O3 Zn2 Zn3 N3 -99.3(9) . . . . ? N5 Zn2 Zn3 N3 15.2(3) 7_556 . . . ? O9 Zn2 Zn3 N3 118.7(2) . . . . ? O3' Zn2 Zn3 N3 -85.4(6) . . . . ? O7 Zn2 Zn3 N3 -166.4(6) . . . . ? N4 Zn2 Zn3 N3 8.9(2) . . . . ? O7' Zn2 Zn3 N3 179.3(6) . . . . ? O3 Zn2 Zn3 O4 13.3(7) . . . . ? N5 Zn2 Zn3 O4 127.7(8) 7_556 . . . ? O9 Zn2 Zn3 O4 -128.7(8) . . . . ? O3' Zn2 Zn3 O4 27.2(6) . . . . ? O7 Zn2 Zn3 O4 -53.8(9) . . . . ? N4 Zn2 Zn3 O4 121.5(8) . . . . ? O7' Zn2 Zn3 O4 -68.1(10) . . . . ? O3 Zn2 Zn3 Zn4 109.0(8) . . . . ? N5 Zn2 Zn3 Zn4 -136.5(3) 7_556 . . . ? O9 Zn2 Zn3 Zn4 -32.98(16) . . . . ? O3' Zn2 Zn3 Zn4 123.0(6) . . . . ? O7 Zn2 Zn3 Zn4 42.0(5) . . . . ? N4 Zn2 Zn3 Zn4 -142.76(14) . . . . ? O7' Zn2 Zn3 Zn4 27.6(6) . . . . ? O9 Zn3 Zn4 O8' -106.8(5) . . . . ? O5 Zn3 Zn4 O8' 104.6(5) . . . . ? O4' Zn3 Zn4 O8' 5.3(7) . . . . ? N3 Zn3 Zn4 O8' -128.5(6) . . . . ? O4 Zn3 Zn4 O8' 7.5(7) . . . . ? Zn2 Zn3 Zn4 O8' -68.5(5) . . . . ? O5 Zn3 Zn4 O9 -148.7(3) . . . . ? O4' Zn3 Zn4 O9 112.0(6) . . . . ? N3 Zn3 Zn4 O9 -21.7(3) . . . . ? O4 Zn3 Zn4 O9 114.2(5) . . . . ? Zn2 Zn3 Zn4 O9 38.2(2) . . . . ? O9 Zn3 Zn4 O8 -90.9(7) . . . . ? O5 Zn3 Zn4 O8 120.4(7) . . . . ? O4' Zn3 Zn4 O8 21.1(9) . . . . ? N3 Zn3 Zn4 O8 -112.7(7) . . . . ? O4 Zn3 Zn4 O8 23.3(8) . . . . ? Zn2 Zn3 Zn4 O8 -52.7(7) . . . . ? O9 Zn3 Zn4 O2 68.4(3) . . . . ? O5 Zn3 Zn4 O2 -80.3(3) . . . . ? O4' Zn3 Zn4 O2 -179.6(6) . . . . ? N3 Zn3 Zn4 O2 46.6(4) . . . . ? O4 Zn3 Zn4 O2 -177.4(5) . . . . ? Zn2 Zn3 Zn4 O2 106.6(2) . . . . ? O9 Zn3 Zn4 O6 160.2(3) . . . . ? O5 Zn3 Zn4 O6 11.5(2) . . . . ? O4' Zn3 Zn4 O6 -87.8(6) . . . . ? N3 Zn3 Zn4 O6 138.5(3) . . . . ? O4 Zn3 Zn4 O6 -85.6(5) . . . . ? Zn2 Zn3 Zn4 O6 -161.55(18) . . . . ? O9 Zn3 Zn4 Zn1 32.1(2) . . . . ? O5 Zn3 Zn4 Zn1 -116.60(16) . . . . ? O4' Zn3 Zn4 Zn1 144.1(5) . . . . ? N3 Zn3 Zn4 Zn1 10.3(3) . . . . ? O4 Zn3 Zn4 Zn1 146.3(5) . . . . ? Zn2 Zn3 Zn4 Zn1 70.32(3) . . . . ? O9 Zn1 Zn4 O8' 55.3(12) . . . . ? N2 Zn1 Zn4 O8' 123.4(12) . . . . ? O1 Zn1 Zn4 O8' -126.4(12) . . . . ? N6 Zn1 Zn4 O8' -26.8(12) . . . . ? N2 Zn1 Zn4 O9 68.1(4) . . . . ? O1 Zn1 Zn4 O9 178.3(2) . . . . ? N6 Zn1 Zn4 O9 -82.1(3) . . . . ? O9 Zn1 Zn4 O8 81.1(6) . . . . ? N2 Zn1 Zn4 O8 149.2(7) . . . . ? O1 Zn1 Zn4 O8 -100.6(6) . . . . ? N6 Zn1 Zn4 O8 -1.0(6) . . . . ? O9 Zn1 Zn4 O2 171.7(3) . . . . ? N2 Zn1 Zn4 O2 -120.2(4) . . . . ? O1 Zn1 Zn4 O2 -10.0(2) . . . . ? N6 Zn1 Zn4 O2 89.6(2) . . . . ? O9 Zn1 Zn4 O6 -90.0(3) . . . . ? N2 Zn1 Zn4 O6 -21.9(4) . . . . ? O1 Zn1 Zn4 O6 88.3(2) . . . . ? N6 Zn1 Zn4 O6 -172.1(3) . . . . ? O9 Zn1 Zn4 Zn3 -33.28(19) . . . . ? N2 Zn1 Zn4 Zn3 34.8(3) . . . . ? O1 Zn1 Zn4 Zn3 145.04(14) . . . . ? N6 Zn1 Zn4 Zn3 -115.34(17) . . . . ? O9 Zn1 N2 C2 -110.0(4) . . . . ? O1 Zn1 N2 C2 107.3(4) . . . . ? N6 Zn1 N2 C2 2.7(4) . . . . ? Zn4 Zn1 N2 C2 -153.2(3) . . . . ? O9 Zn1 N2 C1 68.7(5) . . . . ? O1 Zn1 N2 C1 -73.9(5) . . . . ? N6 Zn1 N2 C1 -178.5(5) . . . . ? Zn4 Zn1 N2 C1 25.5(7) . . . . ? O9 Zn3 N3 C18 -146.1(5) . . . . ? O5 Zn3 N3 C18 -16.3(6) . . . . ? O4' Zn3 N3 C18 92.9(7) . . . . ? O4 Zn3 N3 C18 96.6(8) . . . . ? Zn2 Zn3 N3 C18 173.7(5) . . . . ? Zn4 Zn3 N3 C18 -132.2(4) . . . . ? O9 Zn3 N3 C11 24.7(5) . . . . ? O5 Zn3 N3 C11 154.5(4) . . . . ? O4' Zn3 N3 C11 -96.3(7) . . . . ? O4 Zn3 N3 C11 -92.6(8) . . . . ? Zn2 Zn3 N3 C11 -15.5(5) . . . . ? Zn4 Zn3 N3 C11 38.6(6) . . . . ? O3 Zn2 N4 C12 -112.2(7) . . . 7_556 ? N5 Zn2 N4 C12 -4.7(4) 7_556 . . 7_556 ? O9 Zn2 N4 C12 133.4(4) . . . 7_556 ? O3' Zn2 N4 C12 -110.2(6) . . . 7_556 ? O7 Zn2 N4 C12 -135(4) . . . 7_556 ? O7' Zn2 N4 C12 81(3) . . . 7_556 ? Zn3 Zn2 N4 C12 172.4(4) . . . 7_556 ? O3 Zn2 N4 C11 68.7(9) . . . . ? N5 Zn2 N4 C11 176.2(6) 7_556 . . . ? O9 Zn2 N4 C11 -45.7(6) . . . . ? O3' Zn2 N4 C11 70.6(7) . . . . ? O7 Zn2 N4 C11 46(4) . . . . ? O7' Zn2 N4 C11 -98(3) . . . . ? Zn3 Zn2 N4 C11 -6.8(5) . . . . ? C2 N5 N6 C12 -176.5(5) . . . . ? Zn2 N5 N6 C12 6.5(6) 7_556 . . . ? C2 N5 N6 Zn1 3.2(6) . . . . ? Zn2 N5 N6 Zn1 -173.7(2) 7_556 . . . ? O9 Zn1 N6 C12 -57.3(5) . . . . ? N2 Zn1 N6 C12 176.4(5) . . . . ? O1 Zn1 N6 C12 63.8(5) . . . . ? Zn4 Zn1 N6 C12 -17.7(6) . . . . ? O9 Zn1 N6 N5 123.0(4) . . . . ? N2 Zn1 N6 N5 -3.3(4) . . . . ? O1 Zn1 N6 N5 -115.8(4) . . . . ? Zn4 Zn1 N6 N5 162.7(3) . . . . ? O8' Zn4 O9 Zn1 -145.6(7) . . . . ? O8 Zn4 O9 Zn1 -122.5(7) . . . . ? O2 Zn4 O9 Zn1 -9.0(3) . . . . ? O6 Zn4 O9 Zn1 105.2(2) . . . . ? Zn3 Zn4 O9 Zn1 125.6(3) . . . . ? O8' Zn4 O9 Zn3 88.8(7) . . . . ? O8 Zn4 O9 Zn3 111.9(7) . . . . ? O2 Zn4 O9 Zn3 -134.5(2) . . . . ? O6 Zn4 O9 Zn3 -20.3(3) . . . . ? Zn1 Zn4 O9 Zn3 -125.6(3) . . . . ? O8' Zn4 O9 Zn2 -15.9(8) . . . . ? O8 Zn4 O9 Zn2 7.2(7) . . . . ? O2 Zn4 O9 Zn2 120.7(3) . . . . ? O6 Zn4 O9 Zn2 -125.1(2) . . . . ? Zn3 Zn4 O9 Zn2 -104.7(3) . . . . ? Zn1 Zn4 O9 Zn2 129.7(3) . . . . ? N2 Zn1 O9 Zn4 -146.0(2) . . . . ? O1 Zn1 O9 Zn4 -1.7(2) . . . . ? N6 Zn1 O9 Zn4 118.7(2) . . . . ? N2 Zn1 O9 Zn3 -27.4(3) . . . . ? O1 Zn1 O9 Zn3 116.8(2) . . . . ? N6 Zn1 O9 Zn3 -122.8(2) . . . . ? Zn4 Zn1 O9 Zn3 118.5(3) . . . . ? N2 Zn1 O9 Zn2 80.1(3) . . . . ? O1 Zn1 O9 Zn2 -135.7(2) . . . . ? N6 Zn1 O9 Zn2 -15.3(3) . . . . ? Zn4 Zn1 O9 Zn2 -134.0(3) . . . . ? O5 Zn3 O9 Zn4 32.8(3) . . . . ? O4' Zn3 O9 Zn4 -81.2(7) . . . . ? N3 Zn3 O9 Zn4 167.4(2) . . . . ? O4 Zn3 O9 Zn4 -70.7(6) . . . . ? Zn2 Zn3 O9 Zn4 -122.6(2) . . . . ? O5 Zn3 O9 Zn1 -87.2(2) . . . . ? O4' Zn3 O9 Zn1 158.8(7) . . . . ? N3 Zn3 O9 Zn1 47.5(3) . . . . ? O4 Zn3 O9 Zn1 169.3(6) . . . . ? Zn2 Zn3 O9 Zn1 117.4(3) . . . . ? Zn4 Zn3 O9 Zn1 -119.9(3) . . . . ? O5 Zn3 O9 Zn2 155.43(18) . . . . ? O4' Zn3 O9 Zn2 41.4(7) . . . . ? N3 Zn3 O9 Zn2 -69.9(2) . . . . ? O4 Zn3 O9 Zn2 51.9(6) . . . . ? Zn4 Zn3 O9 Zn2 122.6(2) . . . . ? O3 Zn2 O9 Zn4 69.1(9) . . . . ? N5 Zn2 O9 Zn4 -110.9(3) 7_556 . . . ? O3' Zn2 O9 Zn4 84.3(7) . . . . ? O7 Zn2 O9 Zn4 0.4(5) . . . . ? N4 Zn2 O9 Zn4 174.6(2) . . . . ? O7' Zn2 O9 Zn4 -12.7(6) . . . . ? Zn3 Zn2 O9 Zn4 110.7(3) . . . . ? O3 Zn2 O9 Zn1 -163.0(9) . . . . ? N5 Zn2 O9 Zn1 17.1(3) 7_556 . . . ? O3' Zn2 O9 Zn1 -147.8(7) . . . . ? O7 Zn2 O9 Zn1 128.3(5) . . . . ? N4 Zn2 O9 Zn1 -57.5(2) . . . . ? O7' Zn2 O9 Zn1 115.3(6) . . . . ? Zn3 Zn2 O9 Zn1 -121.3(2) . . . . ? O3 Zn2 O9 Zn3 -41.6(9) . . . . ? N5 Zn2 O9 Zn3 138.4(2) 7_556 . . . ? O3' Zn2 O9 Zn3 -26.4(7) . . . . ? O7 Zn2 O9 Zn3 -110.3(5) . . . . ? N4 Zn2 O9 Zn3 63.88(18) . . . . ? O7' Zn2 O9 Zn3 -123.4(6) . . . . ? C8 N1 C1 N2 178.4(6) . . . . ? C8 N1 C1 C5 -2.2(10) . . . . ? C2 N2 C1 N1 179.7(5) . . . . ? Zn1 N2 C1 N1 1.0(8) . . . . ? C2 N2 C1 C5 0.3(9) . . . . ? Zn1 N2 C1 C5 -178.4(5) . . . . ? N6 N5 C2 N2 -1.0(8) . . . . ? Zn2 N5 C2 N2 175.1(4) 7_556 . . . ? N6 N5 C2 C3 178.7(6) . . . . ? Zn2 N5 C2 C3 -5.2(9) 7_556 . . . ? C1 N2 C2 N5 179.4(5) . . . . ? Zn1 N2 C2 N5 -1.8(7) . . . . ? C1 N2 C2 C3 -0.3(9) . . . . ? Zn1 N2 C2 C3 178.5(5) . . . . ? N5 C2 C3 C4 -179.5(6) . . . . ? N2 C2 C3 C4 0.1(10) . . . . ? C2 C3 C4 C5 0.0(11) . . . . ? N1 C1 C5 C6 0.1(10) . . . . ? N2 C1 C5 C6 179.3(6) . . . . ? N1 C1 C5 C4 -179.4(6) . . . . ? N2 C1 C5 C4 -0.2(9) . . . . ? C3 C4 C5 C6 -179.5(7) . . . . ? C3 C4 C5 C1 0.0(10) . . . . ? C1 C5 C6 C7 1.7(10) . . . . ? C4 C5 C6 C7 -178.9(7) . . . . ? C1 C5 C6 C9 -178.8(7) . . . . ? C4 C5 C6 C9 0.6(11) . . . . ? C5 C6 C7 C8 -1.2(12) . . . . ? C9 C6 C7 C8 179.3(7) . . . . ? C1 N1 C8 C7 2.8(10) . . . . ? C1 N1 C8 C10 -177.6(6) . . . . ? C6 C7 C8 N1 -1.2(12) . . . . ? C6 C7 C8 C10 179.3(7) . . . . ? C12 N4 C11 N3 179.1(5) 7_556 . . . ? Zn2 N4 C11 N3 -1.9(8) . . . . ? C12 N4 C11 C15 0.8(9) 7_556 . . . ? Zn2 N4 C11 C15 179.9(5) . . . . ? C18 N3 C11 N4 -174.6(6) . . . . ? Zn3 N3 C11 N4 14.3(7) . . . . ? C18 N3 C11 C15 3.6(9) . . . . ? Zn3 N3 C11 C15 -167.5(5) . . . . ? N5 N6 C12 N4 -2.2(8) . . . 7_556 ? Zn1 N6 C12 N4 178.2(4) . . . 7_556 ? N5 N6 C12 C13 176.1(5) . . . . ? Zn1 N6 C12 C13 -3.6(8) . . . . ? N6 C12 C13 C14 -178.3(6) . . . . ? N4 C12 C13 C14 -0.1(10) 7_556 . . . ? C12 C13 C14 C15 1.4(10) . . . 7_556 ? N4 C11 C15 C16 179.1(6) . . . . ? N3 C11 C15 C16 1.0(9) . . . . ? N4 C11 C15 C14 -2.2(9) . . . 7_556 ? N3 C11 C15 C14 179.7(6) . . . 7_556 ? C11 C15 C16 C17 -4.3(10) . . . . ? C14 C15 C16 C17 177.1(7) 7_556 . . . ? C11 C15 C16 C19 176.4(7) . . . . ? C14 C15 C16 C19 -2.3(11) 7_556 . . . ? C15 C16 C17 C18 3.0(11) . . . . ? C19 C16 C17 C18 -177.7(7) . . . . ? C16 C17 C18 N3 1.8(12) . . . . ? C16 C17 C18 C20 -179.5(7) . . . . ? C11 N3 C18 C17 -5.1(10) . . . . ? Zn3 N3 C18 C17 166.0(6) . . . . ? C11 N3 C18 C20 176.2(6) . . . . ? Zn3 N3 C18 C20 -12.7(8) . . . . ? O9 Zn1 O1 C21 12.7(7) . . . . ? N2 Zn1 O1 C21 162.0(6) . . . . ? N6 Zn1 O1 C21 -111.8(6) . . . . ? Zn4 Zn1 O1 C21 11.7(6) . . . . ? O8' Zn4 O2 C21 156.9(8) . . . . ? O9 Zn4 O2 C21 20.3(7) . . . . ? O8 Zn4 O2 C21 144.9(8) . . . . ? O6 Zn4 O2 C21 -98.4(7) . . . . ? Zn3 Zn4 O2 C21 -18.0(8) . . . . ? Zn1 Zn4 O2 C21 14.9(6) . . . . ? Zn4 O2 C21 O1 -12.9(11) . . . . ? Zn4 O2 C21 C22 168.9(5) . . . . ? Zn1 O1 C21 O2 -5.4(11) . . . . ? Zn1 O1 C21 C22 173.0(5) . . . . ? N5 Zn2 O3 C23 -164(2) 7_556 . . . ? O9 Zn2 O3 C23 16(2) . . . . ? O3' Zn2 O3 C23 -88(5) . . . . ? O7 Zn2 O3 C23 98(2) . . . . ? N4 Zn2 O3 C23 -80(2) . . . . ? O7' Zn2 O3 C23 98(2) . . . . ? Zn3 Zn2 O3 C23 -11(2) . . . . ? O9 Zn3 O4 C23 -56(2) . . . . ? O5 Zn3 O4 C23 -169(2) . . . . ? O4' Zn3 O4 C23 80(4) . . . . ? N3 Zn3 O4 C23 65(2) . . . . ? Zn2 Zn3 O4 C23 -22(2) . . . . ? Zn4 Zn3 O4 C23 -91(2) . . . . ? Zn2 O3 C23 O4 -2(4) . . . . ? Zn2 O3 C23 C24 -171.5(15) . . . . ? Zn3 O4 C23 O3 24(4) . . . . ? Zn3 O4 C23 C24 -167.3(15) . . . . ? O3 Zn2 O3' C23' 79(4) . . . . ? N5 Zn2 O3' C23' -173.3(16) 7_556 . . . ? O9 Zn2 O3' C23' -4.0(19) . . . . ? O7 Zn2 O3' C23' 83.8(17) . . . . ? N4 Zn2 O3' C23' -93.8(17) . . . . ? O7' Zn2 O3' C23' 84.4(17) . . . . ? Zn3 Zn2 O3' C23' -21.7(16) . . . . ? O9 Zn3 O4' C23' -40(2) . . . . ? O5 Zn3 O4' C23' -159.1(18) . . . . ? N3 Zn3 O4' C23' 78.0(19) . . . . ? O4 Zn3 O4' C23' -88(4) . . . . ? Zn2 Zn3 O4' C23' -12.9(18) . . . . ? Zn4 Zn3 O4' C23' -78.4(19) . . . . ? Zn3 O4' C23' O3' 1(3) . . . . ? Zn3 O4' C23' C24' -169.1(11) . . . . ? Zn2 O3' C23' O4' 21(3) . . . . ? Zn2 O3' C23' C24' -169.4(11) . . . . ? O9 Zn3 O5 C25 -34.7(7) . . . . ? O4' Zn3 O5 C25 87.4(9) . . . . ? N3 Zn3 O5 C25 -164.9(6) . . . . ? O4 Zn3 O5 C25 74.1(10) . . . . ? Zn2 Zn3 O5 C25 -3.3(8) . . . . ? Zn4 Zn3 O5 C25 -15.1(6) . . . . ? O8' Zn4 O6 C25 -122.7(10) . . . . ? O9 Zn4 O6 C25 -2.4(8) . . . . ? O8 Zn4 O6 C25 -136.3(9) . . . . ? O2 Zn4 O6 C25 119.4(8) . . . . ? Zn3 Zn4 O6 C25 -15.0(7) . . . . ? Zn1 Zn4 O6 C25 36.3(8) . . . . ? Zn4 O6 C25 O5 9.6(13) . . . . ? Zn4 O6 C25 C26 -170.6(5) . . . . ? Zn3 O5 C25 O6 10.9(12) . . . . ? Zn3 O5 C25 C26 -168.9(5) . . . . ? O3 Zn2 O7 C27 -129(3) . . . . ? N5 Zn2 O7 C27 125(3) 7_556 . . . ? O9 Zn2 O7 C27 -14(3) . . . . ? O3' Zn2 O7 C27 -130(3) . . . . ? N4 Zn2 O7 C27 -105(5) . . . . ? O7' Zn2 O7 C27 52(4) . . . . ? Zn3 Zn2 O7 C27 -54(3) . . . . ? O8' Zn4 O8 C27 80(3) . . . . ? O9 Zn4 O8 C27 -10.0(19) . . . . ? O2 Zn4 O8 C27 -132.5(17) . . . . ? O6 Zn4 O8 C27 120.4(16) . . . . ? Zn3 Zn4 O8 C27 33(2) . . . . ? Zn1 Zn4 O8 C27 -50.7(19) . . . . ? Zn4 O8 C27 O7 1(3) . . . . ? Zn4 O8 C27 C28 176.4(13) . . . . ? Zn2 O7 C27 O8 14(5) . . . . ? Zn2 O7 C27 C28 -161(2) . . . . ? O3 Zn2 O7' C27' -55(2) . . . . ? N5 Zn2 O7' C27' -163(2) 7_556 . . . ? O9 Zn2 O7' C27' 60(2) . . . . ? O3' Zn2 O7' C27' -56(3) . . . . ? O7 Zn2 O7' C27' -54(3) . . . . ? N4 Zn2 O7' C27' 112(3) . . . . ? Zn3 Zn2 O7' C27' 24(3) . . . . ? O9 Zn4 O8' C27' 36(2) . . . . ? O8 Zn4 O8' C27' -65(2) . . . . ? O2 Zn4 O8' C27' -100(2) . . . . ? O6 Zn4 O8' C27' 152(2) . . . . ? Zn3 Zn4 O8' C27' 76(2) . . . . ? Zn1 Zn4 O8' C27' 4(3) . . . . ? Zn4 O8' C27' O7' -4(4) . . . . ? Zn4 O8' C27' C28' -179.5(19) . . . . ? Zn2 O7' C27' O8' -54(5) . . . . ? Zn2 O7' C27' C28' 121(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.626 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.088 #===END ## Crystallographic Data of Complex 2 data_070628f _database_code_depnum_ccdc_archive 'CCDC 664377' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H40 N8 O10 Zn4' _chemical_formula_weight 970.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.3500(16) _cell_length_b 17.192(2) _cell_length_c 10.0654(15) _cell_angle_alpha 90.00 _cell_angle_beta 99.210(2) _cell_angle_gamma 90.00 _cell_volume 1938.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2331 _cell_measurement_theta_min 2.368 _cell_measurement_theta_max 23.749 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 988 _exptl_absorpt_coefficient_mu 2.510 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3915 _exptl_absorpt_correction_T_max 0.6608 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9172 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3397 _reflns_number_gt 2298 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+2.7443P] 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 3397 _refine_ls_number_parameters 278 _refine_ls_number_restraints 78 _refine_ls_R_factor_all 0.0802 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1333 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.049 _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 0.75512(5) 0.05763(4) 0.37737(6) 0.0505(2) Uani 1 1 d . . . Zn2 Zn 1.18118(5) 0.07741(4) 0.37679(7) 0.0530(2) Uani 1 1 d . . . N1 N 0.8462(4) 0.1391(3) 0.5064(4) 0.0467(11) Uani 1 1 d . B . N2 N 1.0097(4) 0.0879(2) 0.4196(4) 0.0448(10) Uani 1 1 d . B . N3 N 0.9290(4) 0.0419(3) 0.3490(4) 0.0458(11) Uani 1 1 d . B . N4 N 1.0886(4) -0.0024(3) 0.2471(4) 0.0497(11) Uani 1 1 d . B . O1 O 0.7078(3) -0.0234(2) 0.4898(4) 0.0606(11) Uani 1 1 d . . . H1A H 0.6736 -0.0580 0.4369 0.073 Uiso 0.50 1 d PR A 1 O2 O 0.6439(14) 0.1336(4) 0.2604(13) 0.091(3) Uani 0.74(5) 1 d PDU B 1 O3 O 0.6296(16) 0.0171(5) 0.1901(13) 0.106(3) Uani 0.74(5) 1 d PDU B 1 O4 O 1.273(3) 0.1378(9) 0.258(2) 0.072(3) Uani 0.46(8) 1 d PDU C 1 O5 O 1.241(3) 0.2099(11) 0.420(2) 0.105(3) Uani 0.46(8) 1 d PDU C 1 O2' O 0.607(3) 0.121(2) 0.2876(19) 0.089(10) Uani 0.26(5) 1 d PDU B 2 O3' O 0.666(3) 0.033(2) 0.166(2) 0.106(3) Uani 0.26(5) 1 d PDU B 2 O4' O 1.245(3) 0.1483(12) 0.2408(15) 0.072(3) Uani 0.54(8) 1 d PDU C 2 O5' O 1.269(3) 0.1988(13) 0.4358(12) 0.105(3) Uani 0.54(8) 1 d PDU C 2 C1 C 0.9652(5) 0.1387(3) 0.5046(5) 0.0446(12) Uani 1 1 d . . . C2 C 1.0404(5) 0.1890(3) 0.5858(6) 0.0579(15) Uani 1 1 d . B . H2A H 1.1220 0.1894 0.5838 0.070 Uiso 1 1 calc R . . C3 C 0.9914(6) 0.2381(4) 0.6688(7) 0.0673(17) Uani 1 1 d . . . H3A H 1.0409 0.2714 0.7253 0.081 Uiso 1 1 calc R B . C4 C 0.8704(6) 0.2392(4) 0.6706(6) 0.0655(17) Uani 1 1 d . B . H4A H 0.8379 0.2733 0.7266 0.079 Uiso 1 1 calc R . . C5 C 0.7989(5) 0.1893(3) 0.5886(6) 0.0554(15) Uani 1 1 d . . . C6 C 0.6658(5) 0.1865(4) 0.5805(7) 0.083(2) Uani 1 1 d . B . H6A H 0.6407 0.1336 0.5871 0.124 Uiso 1 1 calc R . . H6B H 0.6285 0.2081 0.4962 0.124 Uiso 1 1 calc R . . H6C H 0.6431 0.2163 0.6531 0.124 Uiso 1 1 calc R . . C7 C 0.9717(5) -0.0061(3) 0.2566(5) 0.0476(13) Uani 1 1 d . . . C8 C 0.8927(6) -0.0549(3) 0.1758(6) 0.0561(15) Uani 1 1 d . B . H8A H 0.8123 -0.0564 0.1842 0.067 Uiso 1 1 calc R . . C9 C 0.9364(6) -0.1003(4) 0.0839(6) 0.0696(18) Uani 1 1 d . . . H9A H 0.8857 -0.1337 0.0288 0.084 Uiso 1 1 calc R B . C10 C 1.0559(7) -0.0969(4) 0.0724(6) 0.0697(18) Uani 1 1 d . B . H10A H 1.0857 -0.1278 0.0097 0.084 Uiso 1 1 calc R . . C11 C 1.1302(5) -0.0479(4) 0.1539(6) 0.0585(15) Uani 1 1 d . . . C12 C 1.2601(6) -0.0412(4) 0.1484(7) 0.085(2) Uani 1 1 d . B . H12A H 1.3040 -0.0414 0.2382 0.128 Uiso 1 1 calc R . . H12B H 1.2752 0.0065 0.1043 0.128 Uiso 1 1 calc R . . H12C H 1.2849 -0.0844 0.0991 0.128 Uiso 1 1 calc R . . C13 C 0.5983(5) 0.0861(4) 0.1800(6) 0.0679(18) Uani 1 1 d D B . C14 C 0.5023(6) 0.1099(4) 0.0655(6) 0.079(2) Uani 1 1 d D . . H14A H 0.4956 0.0712 -0.0042 0.118 Uiso 1 1 calc R B . H14B H 0.5227 0.1590 0.0301 0.118 Uiso 1 1 calc R . . H14C H 0.4274 0.1144 0.0978 0.118 Uiso 1 1 calc R . . C15 C 1.2879(4) 0.1995(3) 0.3193(5) 0.0657(17) Uani 1 1 d D C . C16 C 1.3625(6) 0.2626(4) 0.2721(6) 0.078(2) Uani 1 1 d D . . H16A H 1.3486 0.3105 0.3159 0.117 Uiso 1 1 calc R C . H16D H 1.3413 0.2687 0.1765 0.117 Uiso 1 1 calc R . . H16B H 1.4453 0.2489 0.2938 0.117 Uiso 1 1 calc R . . C17 C 0.5871(10) -0.0540(8) 0.4584(15) 0.081(4) Uani 0.50 1 d P D 2 H17A H 0.5338 -0.0134 0.4210 0.122 Uiso 0.50 1 calc PR D 2 H17B H 0.5624 -0.0734 0.5391 0.122 Uiso 0.50 1 calc PR D 2 H17C H 0.5852 -0.0956 0.3943 0.122 Uiso 0.50 1 calc PR D 2 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 0.0374(4) 0.0603(4) 0.0514(4) 0.0018(3) -0.0001(3) -0.0019(3) Zn2 0.0396(4) 0.0678(5) 0.0514(4) 0.0072(3) 0.0069(3) -0.0027(3) N1 0.039(2) 0.055(3) 0.044(3) 0.000(2) 0.000(2) 0.000(2) N2 0.036(2) 0.053(3) 0.045(3) -0.002(2) 0.004(2) -0.006(2) N3 0.039(2) 0.056(3) 0.041(3) -0.003(2) 0.002(2) -0.004(2) N4 0.046(3) 0.060(3) 0.044(3) 0.006(2) 0.010(2) 0.003(2) O1 0.034(2) 0.079(3) 0.066(3) 0.017(2) -0.0001(18) -0.0061(19) O2 0.076(6) 0.102(5) 0.086(6) 0.030(5) -0.022(4) -0.020(4) O3 0.097(5) 0.125(5) 0.089(4) 0.004(4) -0.009(4) 0.030(4) O4 0.067(5) 0.076(4) 0.069(4) 0.008(3) 0.002(4) -0.013(4) O5 0.115(6) 0.121(5) 0.088(4) 0.004(3) 0.038(4) -0.015(4) O2' 0.078(12) 0.091(13) 0.094(12) -0.009(9) 0.004(8) 0.001(8) O3' 0.097(5) 0.125(5) 0.089(4) 0.004(4) -0.009(4) 0.030(4) O4' 0.067(5) 0.076(4) 0.069(4) 0.008(3) 0.002(4) -0.013(4) O5' 0.115(6) 0.121(5) 0.088(4) 0.004(3) 0.038(4) -0.015(4) C1 0.046(3) 0.047(3) 0.039(3) 0.005(2) 0.003(2) -0.001(3) C2 0.050(3) 0.066(4) 0.055(4) -0.004(3) 0.001(3) -0.009(3) C3 0.065(4) 0.065(4) 0.069(4) -0.016(3) 0.000(3) -0.007(3) C4 0.070(4) 0.068(4) 0.058(4) -0.012(3) 0.009(3) 0.001(3) C5 0.056(4) 0.055(4) 0.057(4) 0.004(3) 0.013(3) 0.012(3) C6 0.051(4) 0.104(6) 0.095(5) -0.024(4) 0.018(4) 0.017(4) C7 0.049(3) 0.050(3) 0.043(3) 0.003(3) 0.004(3) 0.002(3) C8 0.060(4) 0.054(3) 0.052(4) -0.008(3) 0.003(3) -0.001(3) C9 0.080(5) 0.068(4) 0.057(4) -0.010(3) 0.000(3) -0.004(4) C10 0.089(5) 0.068(4) 0.055(4) -0.012(3) 0.020(4) 0.009(4) C11 0.062(4) 0.064(4) 0.051(4) 0.005(3) 0.013(3) 0.013(3) C12 0.077(5) 0.103(6) 0.082(5) 0.000(4) 0.034(4) 0.019(4) C13 0.065(4) 0.084(5) 0.054(4) 0.006(4) 0.007(3) 0.006(4) C14 0.061(4) 0.104(5) 0.064(4) 0.007(4) -0.014(3) 0.006(4) C15 0.061(4) 0.083(5) 0.054(4) 0.011(4) 0.010(3) -0.004(4) C16 0.079(5) 0.082(5) 0.072(5) 0.007(4) 0.009(4) -0.021(4) C17 0.034(6) 0.095(10) 0.108(12) 0.026(9) -0.013(7) -0.007(7) _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 1.925(4) . ? Zn1 O2 2.052(7) . ? Zn1 N3 2.056(4) . ? Zn1 N1 2.070(4) . ? Zn1 O2' 2.085(15) . ? Zn1 O3' 2.243(15) . ? Zn1 O3 2.282(8) . ? Zn1 C13 2.494(6) . ? Zn2 O1 1.927(4) 3_756 ? Zn2 O4 1.998(12) . ? Zn2 O4' 2.049(12) . ? Zn2 N4 2.061(5) . ? Zn2 N2 2.067(4) . ? Zn2 O5' 2.348(12) . ? Zn2 O5 2.396(13) . ? Zn2 C15 2.537(6) . ? N1 C1 1.353(6) . ? N1 C5 1.363(7) . ? N2 N3 1.328(6) . ? N2 C1 1.374(6) . ? N3 C7 1.388(6) . ? N4 C7 1.347(6) . ? N4 C11 1.363(7) . ? O1 C17 1.455(11) . ? O1 Zn2 1.927(4) 3_756 ? O1 H1A 0.8500 . ? O2 C13 1.206(7) . ? O3 C13 1.237(7) . ? O4 C15 1.227(8) . ? O5 C15 1.229(8) . ? O2' C13 1.229(8) . ? O3' C13 1.212(8) . ? O4' C15 1.230(7) . ? O5' C15 1.225(7) . ? C1 C2 1.386(7) . ? C2 C3 1.367(8) . ? C2 H2A 0.9300 . ? C3 C4 1.377(8) . ? C3 H3A 0.9300 . ? C4 C5 1.365(8) . ? C4 H4A 0.9300 . ? C5 C6 1.500(8) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.391(7) . ? C8 C9 1.364(8) . ? C8 H8A 0.9300 . ? C9 C10 1.380(9) . ? C9 H9A 0.9300 . ? C10 C11 1.369(9) . ? C10 H10A 0.9300 . ? C11 C12 1.489(8) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.510(8) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.498(8) . ? C16 H16A 0.9600 . ? C16 H16D 0.9600 . ? C16 H16B 0.9600 . ? C17 H1A 1.0409 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O2 126.4(6) . . ? O1 Zn1 N3 110.51(16) . . ? O2 Zn1 N3 121.4(6) . . ? O1 Zn1 N1 106.21(17) . . ? O2 Zn1 N1 97.4(2) . . ? N3 Zn1 N1 77.43(17) . . ? O1 Zn1 O2' 110.6(15) . . ? O2 Zn1 O2' 16.0(10) . . ? N3 Zn1 O2' 137.2(14) . . ? N1 Zn1 O2' 101.8(8) . . ? O1 Zn1 O3' 107.2(14) . . ? O2 Zn1 O3' 55.4(4) . . ? N3 Zn1 O3' 98.1(9) . . ? N1 Zn1 O3' 145.6(13) . . ? O2' Zn1 O3' 58.5(2) . . ? O1 Zn1 O3 93.9(5) . . ? O2 Zn1 O3 58.3(2) . . ? N3 Zn1 O3 109.3(5) . . ? N1 Zn1 O3 155.2(3) . . ? O2' Zn1 O3 56.5(5) . . ? O3' Zn1 O3 14.7(10) . . ? O1 Zn1 C13 112.31(15) . . ? O2 Zn1 C13 28.71(19) . . ? N3 Zn1 C13 119.57(15) . . ? N1 Zn1 C13 126.02(18) . . ? O2' Zn1 C13 29.4(2) . . ? O3' Zn1 C13 29.0(2) . . ? O3 Zn1 C13 29.60(17) . . ? O1 Zn2 O4 108.8(11) 3_756 . ? O1 Zn2 O4' 119.4(10) 3_756 . ? O4 Zn2 O4' 10.7(9) . . ? O1 Zn2 N4 109.33(18) 3_756 . ? O4 Zn2 N4 103.2(5) . . ? O4' Zn2 N4 99.9(3) . . ? O1 Zn2 N2 115.42(16) 3_756 . ? O4 Zn2 N2 132.7(11) . . ? O4' Zn2 N2 122.2(10) . . ? N4 Zn2 N2 77.82(17) . . ? O1 Zn2 O5' 92.7(8) 3_756 . ? O4 Zn2 O5' 56.6(3) . . ? O4' Zn2 O5' 57.3(2) . . ? N4 Zn2 O5' 154.7(5) . . ? N2 Zn2 O5' 104.2(7) . . ? O1 Zn2 O5 101.3(9) 3_756 . ? O4 Zn2 O5 57.0(2) . . ? O4' Zn2 O5 55.6(3) . . ? N4 Zn2 O5 148.0(8) . . ? N2 Zn2 O5 97.4(6) . . ? O5' Zn2 O5 9.2(8) . . ? O1 Zn2 C15 105.95(14) 3_756 . ? O4 Zn2 C15 28.3(2) . . ? O4' Zn2 C15 28.7(2) . . ? N4 Zn2 C15 128.30(17) . . ? N2 Zn2 C15 118.36(15) . . ? O5' Zn2 C15 28.71(17) . . ? O5 Zn2 C15 28.68(17) . . ? C1 N1 C5 120.1(5) . . ? C1 N1 Zn1 112.8(3) . . ? C5 N1 Zn1 127.1(4) . . ? N3 N2 C1 114.9(4) . . ? N3 N2 Zn2 115.4(3) . . ? C1 N2 Zn2 129.6(3) . . ? N2 N3 C7 115.3(4) . . ? N2 N3 Zn1 116.3(3) . . ? C7 N3 Zn1 128.1(3) . . ? C7 N4 C11 118.3(5) . . ? C7 N4 Zn2 113.3(3) . . ? C11 N4 Zn2 128.3(4) . . ? C17 O1 Zn1 118.4(6) . . ? C17 O1 Zn2 117.7(6) . 3_756 ? Zn1 O1 Zn2 123.06(18) . 3_756 ? C17 O1 H1A 44.8 . . ? Zn1 O1 H1A 106.4 . . ? Zn2 O1 H1A 106.3 3_756 . ? C13 O2 Zn1 96.5(5) . . ? C13 O3 Zn1 84.8(5) . . ? C15 O4 Zn2 101.0(8) . . ? C15 O5 Zn2 82.0(7) . . ? C13 O2' Zn1 94.1(9) . . ? C13 O3' Zn1 87.1(8) . . ? C15 O4' Zn2 98.2(8) . . ? C15 O5' Zn2 84.2(7) . . ? N1 C1 N2 118.6(5) . . ? N1 C1 C2 120.7(5) . . ? N2 C1 C2 120.6(5) . . ? C3 C2 C1 118.2(5) . . ? C3 C2 H2A 120.9 . . ? C1 C2 H2A 120.9 . . ? C2 C3 C4 121.4(6) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 118.8(6) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? N1 C5 C4 120.7(5) . . ? N1 C5 C6 116.0(5) . . ? C4 C5 C6 123.2(6) . . ? 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 . . ? N4 C7 N3 118.2(5) . . ? N4 C7 C8 122.5(5) . . ? N3 C7 C8 119.2(5) . . ? C9 C8 C7 118.1(6) . . ? C9 C8 H8A 120.9 . . ? C7 C8 H8A 120.9 . . ? C8 C9 C10 120.1(6) . . ? C8 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? C11 C10 C9 119.7(6) . . ? C11 C10 H10A 120.1 . . ? C9 C10 H10A 120.1 . . ? N4 C11 C10 121.2(6) . . ? N4 C11 C12 115.8(6) . . ? C10 C11 C12 123.0(6) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O2 C13 O3' 111.9(12) . . ? O2 C13 O2' 27.3(18) . . ? O3' C13 O2' 120.3(8) . . ? O2 C13 O3 120.4(7) . . ? O3' C13 O3 27.4(18) . . ? O2' C13 O3 114.5(13) . . ? O2 C13 C14 120.6(6) . . ? O3' C13 C14 120.6(7) . . ? O2' C13 C14 119.1(7) . . ? O3 C13 C14 119.0(6) . . ? O2 C13 Zn1 54.8(4) . . ? O3' C13 Zn1 63.9(8) . . ? O2' C13 Zn1 56.5(7) . . ? O3 C13 Zn1 65.6(4) . . ? C14 C13 Zn1 175.3(4) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O5' C15 O4 116.2(11) . . ? O5' C15 O5 18.0(15) . . ? O4 C15 O5 119.8(7) . . ? O5' C15 O4' 119.7(7) . . ? O4 C15 O4' 17.8(15) . . ? O5 C15 O4' 117.0(11) . . ? O5' C15 C16 120.3(7) . . ? O4 C15 C16 120.4(7) . . ? O5 C15 C16 119.8(7) . . ? O4' C15 C16 120.0(6) . . ? O5' C15 Zn2 67.1(6) . . ? O4 C15 Zn2 50.6(6) . . ? O5 C15 Zn2 69.3(7) . . ? O4' C15 Zn2 53.1(6) . . ? C16 C15 Zn2 170.3(3) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16D 109.5 . . ? H16A C16 H16D 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? H16D C16 H16B 109.5 . . ? O1 C17 H1A 35.1 . . ? O1 C17 H17A 109.5 . . ? O1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 N1 C1 107.8(3) . . . . ? O2 Zn1 N1 C1 -120.8(7) . . . . ? N3 Zn1 N1 C1 -0.2(3) . . . . ? O2' Zn1 N1 C1 -136.4(14) . . . . ? O3' Zn1 N1 C1 -86.2(13) . . . . ? O3 Zn1 N1 C1 -109.3(14) . . . . ? C13 Zn1 N1 C1 -117.8(3) . . . . ? O1 Zn1 N1 C5 -71.7(4) . . . . ? O2 Zn1 N1 C5 59.7(7) . . . . ? N3 Zn1 N1 C5 -179.7(5) . . . . ? O2' Zn1 N1 C5 44.1(14) . . . . ? O3' Zn1 N1 C5 94.3(13) . . . . ? O3 Zn1 N1 C5 71.3(14) . . . . ? C13 Zn1 N1 C5 62.7(5) . . . . ? O1 Zn2 N2 N3 -105.7(4) 3_756 . . . ? O4 Zn2 N2 N3 96.9(7) . . . . ? O4' Zn2 N2 N3 94.2(4) . . . . ? N4 Zn2 N2 N3 0.1(3) . . . . ? O5' Zn2 N2 N3 154.3(6) . . . . ? O5 Zn2 N2 N3 148.0(8) . . . . ? C15 Zn2 N2 N3 127.3(3) . . . . ? O1 Zn2 N2 C1 78.7(5) 3_756 . . . ? O4 Zn2 N2 C1 -78.7(8) . . . . ? O4' Zn2 N2 C1 -81.4(5) . . . . ? N4 Zn2 N2 C1 -175.5(5) . . . . ? O5' Zn2 N2 C1 -21.4(7) . . . . ? O5 Zn2 N2 C1 -27.6(8) . . . . ? C15 Zn2 N2 C1 -48.4(5) . . . . ? C1 N2 N3 C7 176.0(4) . . . . ? Zn2 N2 N3 C7 -0.3(6) . . . . ? C1 N2 N3 Zn1 1.5(6) . . . . ? Zn2 N2 N3 Zn1 -174.86(18) . . . . ? O1 Zn1 N3 N2 -103.5(4) . . . . ? O2 Zn1 N3 N2 90.4(4) . . . . ? N1 Zn1 N3 N2 -0.7(3) . . . . ? O2' Zn1 N3 N2 93.2(11) . . . . ? O3' Zn1 N3 N2 144.7(12) . . . . ? O3 Zn1 N3 N2 154.5(5) . . . . ? C13 Zn1 N3 N2 123.8(4) . . . . ? O1 Zn1 N3 C7 82.8(4) . . . . ? O2 Zn1 N3 C7 -83.3(5) . . . . ? N1 Zn1 N3 C7 -174.4(5) . . . . ? O2' Zn1 N3 C7 -80.5(11) . . . . ? O3' Zn1 N3 C7 -29.1(12) . . . . ? O3 Zn1 N3 C7 -19.3(6) . . . . ? C13 Zn1 N3 C7 -49.9(5) . . . . ? O1 Zn2 N4 C7 113.0(4) 3_756 . . . ? O4 Zn2 N4 C7 -131.4(11) . . . . ? O4' Zn2 N4 C7 -121.0(11) . . . . ? N2 Zn2 N4 C7 0.0(3) . . . . ? O5' Zn2 N4 C7 -97.5(18) . . . . ? O5 Zn2 N4 C7 -84.4(10) . . . . ? C15 Zn2 N4 C7 -116.6(3) . . . . ? O1 Zn2 N4 C11 -69.3(5) 3_756 . . . ? O4 Zn2 N4 C11 46.4(12) . . . . ? O4' Zn2 N4 C11 56.8(11) . . . . ? N2 Zn2 N4 C11 177.8(5) . . . . ? O5' Zn2 N4 C11 80.2(18) . . . . ? O5 Zn2 N4 C11 93.4(10) . . . . ? C15 Zn2 N4 C11 61.1(5) . . . . ? O2 Zn1 O1 C17 23.4(9) . . . . ? N3 Zn1 O1 C17 -141.8(8) . . . . ? N1 Zn1 O1 C17 135.9(8) . . . . ? O2' Zn1 O1 C17 26.2(9) . . . . ? O3' Zn1 O1 C17 -35.9(9) . . . . ? O3 Zn1 O1 C17 -29.4(9) . . . . ? C13 Zn1 O1 C17 -5.5(8) . . . . ? O2 Zn1 O1 Zn2 -166.8(4) . . . 3_756 ? N3 Zn1 O1 Zn2 28.0(3) . . . 3_756 ? N1 Zn1 O1 Zn2 -54.3(3) . . . 3_756 ? O2' Zn1 O1 Zn2 -164.0(4) . . . 3_756 ? O3' Zn1 O1 Zn2 133.9(5) . . . 3_756 ? O3 Zn1 O1 Zn2 140.3(4) . . . 3_756 ? C13 Zn1 O1 Zn2 164.3(2) . . . 3_756 ? O1 Zn1 O2 C13 -68.5(13) . . . . ? N3 Zn1 O2 C13 95.2(10) . . . . ? N1 Zn1 O2 C13 175.0(10) . . . . ? O2' Zn1 O2 C13 -77.9(16) . . . . ? O3' Zn1 O2 C13 17.9(11) . . . . ? O3 Zn1 O2 C13 0.6(2) . . . . ? O1 Zn1 O3 C13 130.5(10) . . . . ? O2 Zn1 O3 C13 -0.6(2) . . . . ? N3 Zn1 O3 C13 -116.2(9) . . . . ? N1 Zn1 O3 C13 -14(2) . . . . ? O2' Zn1 O3 C13 18.3(12) . . . . ? O3' Zn1 O3 C13 -74.6(11) . . . . ? O1 Zn2 O4 C15 -89(2) 3_756 . . . ? O4' Zn2 O4 C15 82(2) . . . . ? N4 Zn2 O4 C15 155.1(18) . . . . ? N2 Zn2 O4 C15 70(2) . . . . ? O5' Zn2 O4 C15 -8.3(10) . . . . ? O5 Zn2 O4 C15 2.6(3) . . . . ? O1 Zn2 O5 C15 102.6(17) 3_756 . . . ? O4 Zn2 O5 C15 -2.6(3) . . . . ? O4' Zn2 O5 C15 -15.4(9) . . . . ? N4 Zn2 O5 C15 -61(2) . . . . ? N2 Zn2 O5 C15 -139.5(16) . . . . ? O5' Zn2 O5 C15 81.7(16) . . . . ? O1 Zn1 O2' C13 -99(3) . . . . ? O2 Zn1 O2' C13 72.9(12) . . . . ? N3 Zn1 O2' C13 64(3) . . . . ? N1 Zn1 O2' C13 148(2) . . . . ? O3' Zn1 O2' C13 -1.0(3) . . . . ? O3 Zn1 O2' C13 -18.3(12) . . . . ? O1 Zn1 O3' C13 105(2) . . . . ? O2 Zn1 O3' C13 -17.7(11) . . . . ? N3 Zn1 O3' C13 -140(2) . . . . ? N1 Zn1 O3' C13 -61(4) . . . . ? O2' Zn1 O3' C13 1.0(3) . . . . ? O3 Zn1 O3' C13 78.8(14) . . . . ? O1 Zn2 O4' C15 -68(2) 3_756 . . . ? O4 Zn2 O4' C15 -78(2) . . . . ? N4 Zn2 O4' C15 172.9(17) . . . . ? N2 Zn2 O4' C15 91.1(19) . . . . ? O5' Zn2 O4' C15 4.5(3) . . . . ? O5 Zn2 O4' C15 15.4(9) . . . . ? O1 Zn2 O5' C15 119.1(16) 3_756 . . . ? O4 Zn2 O5' C15 8.2(10) . . . . ? O4' Zn2 O5' C15 -4.5(3) . . . . ? N4 Zn2 O5' C15 -32(3) . . . . ? N2 Zn2 O5' C15 -123.8(15) . . . . ? O5 Zn2 O5' C15 -81.4(16) . . . . ? C5 N1 C1 N2 -179.4(5) . . . . ? Zn1 N1 C1 N2 1.1(6) . . . . ? C5 N1 C1 C2 0.1(7) . . . . ? Zn1 N1 C1 C2 -179.4(4) . . . . ? N3 N2 C1 N1 -1.7(7) . . . . ? Zn2 N2 C1 N1 173.9(3) . . . . ? N3 N2 C1 C2 178.8(5) . . . . ? Zn2 N2 C1 C2 -5.5(7) . . . . ? N1 C1 C2 C3 0.9(8) . . . . ? N2 C1 C2 C3 -179.7(5) . . . . ? C1 C2 C3 C4 -1.4(9) . . . . ? C2 C3 C4 C5 0.9(10) . . . . ? C1 N1 C5 C4 -0.6(8) . . . . ? Zn1 N1 C5 C4 178.8(4) . . . . ? C1 N1 C5 C6 178.4(5) . . . . ? Zn1 N1 C5 C6 -2.2(7) . . . . ? C3 C4 C5 N1 0.1(9) . . . . ? C3 C4 C5 C6 -178.8(6) . . . . ? C11 N4 C7 N3 -178.2(5) . . . . ? Zn2 N4 C7 N3 -0.2(6) . . . . ? C11 N4 C7 C8 0.4(8) . . . . ? Zn2 N4 C7 C8 178.4(4) . . . . ? N2 N3 C7 N4 0.4(7) . . . . ? Zn1 N3 C7 N4 174.1(4) . . . . ? N2 N3 C7 C8 -178.3(5) . . . . ? Zn1 N3 C7 C8 -4.5(7) . . . . ? N4 C7 C8 C9 0.1(9) . . . . ? N3 C7 C8 C9 178.7(5) . . . . ? C7 C8 C9 C10 -0.4(9) . . . . ? C8 C9 C10 C11 0.1(10) . . . . ? C7 N4 C11 C10 -0.7(8) . . . . ? Zn2 N4 C11 C10 -178.3(4) . . . . ? C7 N4 C11 C12 -179.9(5) . . . . ? Zn2 N4 C11 C12 2.5(7) . . . . ? C9 C10 C11 N4 0.4(10) . . . . ? C9 C10 C11 C12 179.6(6) . . . . ? Zn1 O2 C13 O3' -30.3(18) . . . . ? Zn1 O2 C13 O2' 84(2) . . . . ? Zn1 O2 C13 O3 -1.2(4) . . . . ? Zn1 O2 C13 C14 178.8(4) . . . . ? Zn1 O3' C13 O2 27.3(16) . . . . ? Zn1 O3' C13 O2' -1.7(5) . . . . ? Zn1 O3' C13 O3 -87.0(19) . . . . ? Zn1 O3' C13 C14 178.2(4) . . . . ? Zn1 O2' C13 O2 -77.1(17) . . . . ? Zn1 O2' C13 O3' 1.9(6) . . . . ? Zn1 O2' C13 O3 32.2(19) . . . . ? Zn1 O2' C13 C14 -178.1(4) . . . . ? Zn1 O3 C13 O2 1.0(4) . . . . ? Zn1 O3 C13 O3' 79.8(18) . . . . ? Zn1 O3 C13 O2' -29.2(18) . . . . ? Zn1 O3 C13 C14 -178.9(3) . . . . ? O1 Zn1 C13 O2 126.0(12) . . . . ? N3 Zn1 C13 O2 -102.1(12) . . . . ? N1 Zn1 C13 O2 -6.2(12) . . . . ? O2' Zn1 C13 O2 33(2) . . . . ? O3' Zn1 C13 O2 -149(2) . . . . ? O3 Zn1 C13 O2 -178.9(4) . . . . ? O1 Zn1 C13 O3' -85(3) . . . . ? O2 Zn1 C13 O3' 149(2) . . . . ? N3 Zn1 C13 O3' 47(3) . . . . ? N1 Zn1 C13 O3' 142(3) . . . . ? O2' Zn1 C13 O3' -178.2(5) . . . . ? O3 Zn1 C13 O3' -30(2) . . . . ? O1 Zn1 C13 O2' 93(3) . . . . ? O2 Zn1 C13 O2' -33(2) . . . . ? N3 Zn1 C13 O2' -135(3) . . . . ? N1 Zn1 C13 O2' -39(3) . . . . ? O3' Zn1 C13 O2' 178.2(5) . . . . ? O3 Zn1 C13 O2' 148(2) . . . . ? O1 Zn1 C13 O3 -55.1(12) . . . . ? O2 Zn1 C13 O3 178.9(4) . . . . ? N3 Zn1 C13 O3 76.8(12) . . . . ? N1 Zn1 C13 O3 172.7(12) . . . . ? O2' Zn1 C13 O3 -148(2) . . . . ? O3' Zn1 C13 O3 30(2) . . . . ? O1 Zn1 C13 C14 114(4) . . . . ? O2 Zn1 C13 C14 -12(4) . . . . ? N3 Zn1 C13 C14 -114(4) . . . . ? N1 Zn1 C13 C14 -19(4) . . . . ? O2' Zn1 C13 C14 21(5) . . . . ? O3' Zn1 C13 C14 -161(4) . . . . ? O3 Zn1 C13 C14 169(4) . . . . ? Zn2 O5' C15 O4 -12.5(15) . . . . ? Zn2 O5' C15 O5 94(3) . . . . ? Zn2 O5' C15 O4' 7.3(5) . . . . ? Zn2 O5' C15 C16 -172.8(4) . . . . ? Zn2 O4 C15 O5' 15.0(18) . . . . ? Zn2 O4 C15 O5 -5.0(6) . . . . ? Zn2 O4 C15 O4' -91(3) . . . . ? Zn2 O4 C15 C16 175.3(5) . . . . ? Zn2 O5 C15 O5' -79(3) . . . . ? Zn2 O5 C15 O4 4.1(5) . . . . ? Zn2 O5 C15 O4' 24.1(15) . . . . ? Zn2 O5 C15 C16 -176.1(5) . . . . ? Zn2 O4' C15 O5' -8.4(5) . . . . ? Zn2 O4' C15 O4 75(3) . . . . ? Zn2 O4' C15 O5 -28.6(17) . . . . ? Zn2 O4' C15 C16 171.7(4) . . . . ? O1 Zn2 C15 O5' -65.2(18) 3_756 . . . ? O4 Zn2 C15 O5' -165.4(18) . . . . ? O4' Zn2 C15 O5' 172.1(5) . . . . ? N4 Zn2 C15 O5' 163.1(19) . . . . ? N2 Zn2 C15 O5' 66.2(19) . . . . ? O5 Zn2 C15 O5' 19.2(16) . . . . ? O1 Zn2 C15 O4 100(2) 3_756 . . . ? O4' Zn2 C15 O4 -22.5(18) . . . . ? N4 Zn2 C15 O4 -31(2) . . . . ? N2 Zn2 C15 O4 -128(2) . . . . ? O5' Zn2 C15 O4 165.4(18) . . . . ? O5 Zn2 C15 O4 -175.4(6) . . . . ? O1 Zn2 C15 O5 -84(2) 3_756 . . . ? O4 Zn2 C15 O5 175.4(6) . . . . ? O4' Zn2 C15 O5 152.9(17) . . . . ? N4 Zn2 C15 O5 144(2) . . . . ? N2 Zn2 C15 O5 47(2) . . . . ? O5' Zn2 C15 O5 -19.2(16) . . . . ? O1 Zn2 C15 O4' 123(2) 3_756 . . . ? O4 Zn2 C15 O4' 22.5(18) . . . . ? N4 Zn2 C15 O4' -9(2) . . . . ? N2 Zn2 C15 O4' -106(2) . . . . ? O5' Zn2 C15 O4' -172.1(5) . . . . ? O5 Zn2 C15 O4' -152.9(17) . . . . ? O1 Zn2 C15 C16 75.3(18) 3_756 . . . ? O4 Zn2 C15 C16 -25(3) . . . . ? O4' Zn2 C15 C16 -47(3) . . . . ? N4 Zn2 C15 C16 -56.3(17) . . . . ? N2 Zn2 C15 C16 -153.2(17) . . . . ? O5' Zn2 C15 C16 141(3) . . . . ? O5 Zn2 C15 C16 160(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.743 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.084 #===END #===END ## Crystallographic Data of Compound L data_061203a _database_code_depnum_ccdc_archive 'CCDC 664378' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 N6' _chemical_formula_weight 342.40 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.017(4) _cell_length_b 10.788(6) _cell_length_c 10.389(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.298(7) _cell_angle_gamma 90.00 _cell_volume 893.0(9) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 936 _cell_measurement_theta_min 2.731 _cell_measurement_theta_max 25.169 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9564 _exptl_absorpt_correction_T_max 0.9802 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4487 _diffrn_reflns_av_R_equivalents 0.0596 _diffrn_reflns_av_sigmaI/netI 0.0614 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1575 _reflns_number_gt 804 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+0.3788P] 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 1575 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1191 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.2002 _refine_ls_wR_factor_gt 0.1536 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 N1 N 0.7711(3) 0.0732(2) 0.5700(3) 0.0556(8) Uani 1 1 d . . . N2 N 0.6600(3) 0.2687(2) 0.5374(2) 0.0526(8) Uani 1 1 d . . . N3 N 0.5559(3) 0.4664(2) 0.5261(3) 0.0638(9) Uani 1 1 d . . . C1 C 0.6754(4) 0.1527(3) 0.4885(3) 0.0480(8) Uani 1 1 d . . . C2 C 0.5642(4) 0.3470(3) 0.4647(3) 0.0531(9) Uani 1 1 d . . . C3 C 0.4824(4) 0.3205(3) 0.3426(3) 0.0598(10) Uani 1 1 d . . . H3 H 0.4168 0.3799 0.2962 0.072 Uiso 1 1 calc R . . C4 C 0.5012(4) 0.2059(3) 0.2936(3) 0.0588(10) Uani 1 1 d . . . H4 H 0.4491 0.1859 0.2118 0.071 Uiso 1 1 calc R . . C5 C 0.5988(4) 0.1170(3) 0.3657(3) 0.0496(8) Uani 1 1 d . . . C6 C 0.6249(4) -0.0070(3) 0.3233(4) 0.0620(10) Uani 1 1 d . . . C7 C 0.7191(5) -0.0820(3) 0.4069(4) 0.0666(11) Uani 1 1 d . . . H7 H 0.7363 -0.1637 0.3831 0.080 Uiso 1 1 calc R . . C8 C 0.7914(4) -0.0403(3) 0.5283(4) 0.0578(9) Uani 1 1 d . . . C9 C 0.5464(5) -0.0499(4) 0.1923(4) 0.0979(15) Uani 1 1 d . . . H9A H 0.5788 -0.1341 0.1784 0.147 Uiso 1 1 calc R . . H9B H 0.5839 0.0020 0.1262 0.147 Uiso 1 1 calc R . . H9C H 0.4264 -0.0450 0.1889 0.147 Uiso 1 1 calc R . . C10 C 0.8967(4) -0.1257(3) 0.6173(4) 0.0784(12) Uani 1 1 d . . . H10A H 0.9891 -0.0804 0.6612 0.118 Uiso 1 1 calc R . . H10B H 0.9387 -0.1917 0.5680 0.118 Uiso 1 1 calc R . . H10C H 0.8297 -0.1597 0.6799 0.118 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 N1 0.0535(17) 0.0480(17) 0.0652(19) 0.0003(14) 0.0060(14) 0.0016(13) N2 0.0510(17) 0.0480(16) 0.0566(18) -0.0081(13) -0.0049(13) 0.0054(12) N3 0.062(2) 0.0546(19) 0.070(2) -0.0084(15) -0.0113(15) 0.0131(13) C1 0.0409(19) 0.049(2) 0.053(2) -0.0044(16) 0.0046(15) -0.0009(15) C2 0.049(2) 0.050(2) 0.058(2) -0.0078(17) -0.0040(16) 0.0014(15) C3 0.054(2) 0.063(2) 0.059(2) -0.0019(18) -0.0092(17) 0.0058(17) C4 0.052(2) 0.074(2) 0.049(2) -0.0133(19) -0.0054(16) -0.0070(17) C5 0.0407(18) 0.055(2) 0.053(2) -0.0088(16) 0.0042(16) -0.0073(15) C6 0.054(2) 0.058(2) 0.075(3) -0.025(2) 0.0149(19) -0.0124(17) C7 0.064(2) 0.045(2) 0.095(3) -0.011(2) 0.023(2) -0.0054(18) C8 0.053(2) 0.048(2) 0.075(3) 0.0023(18) 0.0181(19) -0.0055(16) C9 0.103(3) 0.090(3) 0.099(3) -0.050(3) 0.003(3) -0.006(2) C10 0.074(3) 0.052(2) 0.112(3) 0.016(2) 0.022(2) 0.0092(19) _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 N1 C8 1.314(4) . ? N1 C1 1.377(4) . ? N2 C2 1.322(4) . ? N2 C1 1.361(4) . ? N3 N3 1.232(5) 3_666 ? N3 C2 1.442(4) . ? C1 C5 1.408(4) . ? C2 C3 1.392(4) . ? C3 C4 1.352(4) . ? C3 H3 0.9300 . ? C4 C5 1.401(4) . ? C4 H4 0.9300 . ? C5 C6 1.431(5) . ? C6 C7 1.355(5) . ? C6 C9 1.508(5) . ? C7 C8 1.403(5) . ? C7 H7 0.9300 . ? C8 C10 1.498(4) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 N1 C1 117.3(3) . . ? C2 N2 C1 116.5(3) . . ? N3 N3 C2 113.5(3) 3_666 . ? N2 C1 N1 114.2(3) . . ? N2 C1 C5 122.7(3) . . ? N1 C1 C5 123.0(3) . . ? N2 C2 C3 125.1(3) . . ? N2 C2 N3 111.8(3) . . ? C3 C2 N3 123.1(3) . . ? C4 C3 C2 118.1(3) . . ? C4 C3 H3 121.0 . . ? C2 C3 H3 121.0 . . ? C3 C4 C5 120.2(3) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C1 117.4(3) . . ? C4 C5 C6 124.5(3) . . ? C1 C5 C6 118.1(3) . . ? C7 C6 C5 116.8(3) . . ? C7 C6 C9 122.9(3) . . ? C5 C6 C9 120.3(4) . . ? C6 C7 C8 122.1(3) . . ? C6 C7 H7 118.9 . . ? C8 C7 H7 118.9 . . ? N1 C8 C7 122.7(3) . . ? N1 C8 C10 116.8(3) . . ? C7 C8 C10 120.5(3) . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.499 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.043 #===END ## Crystallographic Data of Compound H2L data_a _database_code_depnum_ccdc_archive 'CCDC 664379' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 Cl3 N3' _chemical_formula_weight 291.58 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' 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.3383(15) _cell_length_b 22.678(5) _cell_length_c 8.0867(16) _cell_angle_alpha 90.00 _cell_angle_beta 95.07(3) _cell_angle_gamma 90.00 _cell_volume 1340.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6437 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 25.03 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 0.664 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.767 _exptl_absorpt_correction_T_max 0.923 _exptl_absorpt_process_details ; HIGASHI, T. (1995). Abscor-Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation,Tokyo,Japan. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS RAPID IP' _diffrn_measurement_method \W _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6437 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.1118 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2318 _reflns_number_gt 766 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid-AUTO (Rigaku,2000)' _computing_cell_refinement Rapid-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC,2000)' _computing_structure_solution SHELXS-97,(Sheldrick,1997) _computing_structure_refinement SHELXL-97,(Sheldrick,1997) _computing_molecular_graphics 'Siemens SHELXTL V4.2,(Sheldrick,1990)' _computing_publication_material SHELXL-97,(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^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom or difmap' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0040(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2318 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1689 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1399 _refine_ls_wR_factor_gt 0.1204 _refine_ls_goodness_of_fit_ref 0.931 _refine_ls_restrained_S_all 0.931 _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 Cl1 Cl -0.0492(4) -0.26664(9) 0.9379(3) 0.2367(15) Uani 1 1 d . . . Cl2 Cl 0.3244(4) -0.26226(9) 0.8728(3) 0.2202(13) Uani 1 1 d . . . Cl3 Cl 0.0773(3) -0.32799(8) 0.6630(2) 0.1615(10) Uani 1 1 d . . . N1 N 0.7193(4) -0.06611(15) 0.5171(4) 0.0536(9) Uani 1 1 d . . . N2 N 0.6351(4) -0.01681(14) 0.2740(4) 0.0491(9) Uani 1 1 d . . . HN2 H 0.5661 -0.0450 0.2225 0.093 Uiso 1 1 d . . . N3 N 0.5283(5) 0.02816(12) 0.0183(4) 0.0539(10) Uani 1 1 d . . . C1 C 0.7110(5) -0.0141(2) 0.4350(5) 0.0486(11) Uani 1 1 d . . . C2 C 0.7717(5) 0.04025(19) 0.5014(5) 0.0509(11) Uani 1 1 d . . . C3 C 0.8453(5) 0.0399(2) 0.6701(5) 0.0594(13) Uani 1 1 d . . . C4 C 0.8500(6) -0.0136(3) 0.7519(5) 0.0679(14) Uani 1 1 d . . . H4 H 0.8952 -0.0149 0.8629 0.082 Uiso 1 1 calc R . . C5 C 0.7903(6) -0.0654(2) 0.6749(5) 0.0592(12) Uani 1 1 d . . . C6 C 0.7547(5) 0.09080(18) 0.3949(5) 0.0541(12) Uani 1 1 d . . . H6 H 0.7958 0.1273 0.4348 0.065 Uiso 1 1 calc R . . C7 C 0.6807(5) 0.08586(19) 0.2402(5) 0.0589(12) Uani 1 1 d . . . H7 H 0.6744 0.1192 0.1729 0.071 Uiso 1 1 calc R . . C8 C 0.6096(5) 0.03107(18) 0.1716(5) 0.0490(11) Uani 1 1 d . . . C9 C 0.8008(6) -0.1221(2) 0.7668(5) 0.0840(16) Uani 1 1 d . . . H9A H 0.7527 -0.1532 0.6950 0.126 Uiso 1 1 calc R . . H9B H 0.7303 -0.1193 0.8610 0.126 Uiso 1 1 calc R . . H9C H 0.9260 -0.1305 0.8037 0.126 Uiso 1 1 calc R . . C10 C 0.9121(7) 0.0953(2) 0.7577(5) 0.0858(15) Uani 1 1 d . . . H10A H 0.8978 0.1280 0.6823 0.129 Uiso 1 1 calc R . . H10B H 1.0389 0.0910 0.7962 0.129 Uiso 1 1 calc R . . H10C H 0.8422 0.1024 0.8506 0.129 Uiso 1 1 calc R . . C11 C 0.1301(8) -0.3036(2) 0.8616(6) 0.111(2) Uani 1 1 d . . . H11 H 0.1554 -0.3385 0.9316 0.134 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 Cl1 0.349(4) 0.1104(16) 0.277(3) 0.0430(17) 0.179(3) 0.0805(19) Cl2 0.246(3) 0.1347(18) 0.273(3) -0.0293(18) -0.020(2) -0.0762(18) Cl3 0.223(2) 0.1477(16) 0.1034(13) -0.0113(12) -0.0462(13) 0.0260(15) N1 0.052(2) 0.063(2) 0.044(2) -0.0038(19) -0.0059(17) 0.005(2) N2 0.052(2) 0.054(2) 0.0391(19) 0.0062(18) -0.0063(16) -0.0074(18) N3 0.068(3) 0.046(2) 0.045(2) 0.0025(19) -0.0050(18) 0.003(2) C1 0.039(3) 0.061(3) 0.045(3) -0.002(2) 0.000(2) 0.001(2) C2 0.043(3) 0.060(3) 0.049(3) -0.011(2) 0.001(2) -0.006(2) C3 0.044(3) 0.078(4) 0.055(3) -0.017(3) -0.001(2) 0.003(3) C4 0.055(3) 0.108(4) 0.039(2) 0.001(3) -0.008(2) 0.012(3) C5 0.058(3) 0.071(3) 0.047(3) 0.006(3) -0.002(2) 0.000(3) C6 0.054(3) 0.060(3) 0.048(3) -0.003(2) 0.002(2) -0.004(2) C7 0.063(3) 0.061(3) 0.052(3) 0.006(2) 0.004(2) 0.001(2) C8 0.057(3) 0.049(3) 0.041(2) -0.002(2) 0.005(2) 0.000(2) C9 0.084(4) 0.106(4) 0.059(3) 0.022(3) -0.010(3) 0.012(3) C10 0.087(4) 0.102(4) 0.065(3) -0.018(3) -0.017(3) -0.005(3) C11 0.185(7) 0.063(3) 0.083(4) -0.011(3) -0.007(4) 0.010(4) _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 Cl1 C11 1.720(6) . ? Cl2 C11 1.702(6) . ? Cl3 C11 1.711(5) . ? N1 C5 1.335(5) . ? N1 C1 1.351(5) . ? N2 C8 1.368(4) . ? N2 C1 1.372(4) . ? N2 HN2 0.894(3) . ? N3 C8 1.329(4) . ? N3 N3 1.367(6) 3_655 ? C1 C2 1.402(5) . ? C2 C3 1.422(5) . ? C2 C6 1.433(5) . ? C3 C4 1.382(6) . ? C3 C10 1.503(5) . ? C4 C5 1.382(6) . ? C4 H4 0.9300 . ? C5 C9 1.483(6) . ? C6 C7 1.324(5) . ? C6 H6 0.9300 . ? C7 C8 1.439(5) . ? C7 H7 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11 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 C5 N1 C1 117.1(4) . . ? C8 N2 C1 124.2(4) . . ? C8 N2 HN2 104.1(3) . . ? C1 N2 HN2 129.7(4) . . ? C8 N3 N3 110.5(4) . 3_655 ? N1 C1 N2 115.1(4) . . ? N1 C1 C2 125.5(3) . . ? N2 C1 C2 119.4(4) . . ? C1 C2 C3 116.3(4) . . ? C1 C2 C6 117.8(4) . . ? C3 C2 C6 125.9(4) . . ? C4 C3 C2 117.1(4) . . ? C4 C3 C10 121.1(4) . . ? C2 C3 C10 121.9(5) . . ? C3 C4 C5 122.5(4) . . ? C3 C4 H4 118.7 . . ? C5 C4 H4 118.7 . . ? N1 C5 C4 121.5(4) . . ? N1 C5 C9 117.8(4) . . ? C4 C5 C9 120.7(4) . . ? C7 C6 C2 120.5(4) . . ? C7 C6 H6 119.8 . . ? C2 C6 H6 119.8 . . ? C6 C7 C8 122.8(4) . . ? C6 C7 H7 118.6 . . ? C8 C7 H7 118.6 . . ? N3 C8 N2 123.4(4) . . ? N3 C8 C7 121.3(4) . . ? N2 C8 C7 115.3(3) . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C3 C10 H10A 109.5 . . ? C3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? Cl2 C11 Cl3 110.3(3) . . ? Cl2 C11 Cl1 112.1(3) . . ? Cl3 C11 Cl1 112.2(3) . . ? Cl2 C11 H11 107.3 . . ? Cl3 C11 H11 107.3 . . ? Cl1 C11 H11 107.3 . . ? 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 C5 N1 C1 N2 -179.2(4) . . . . ? C5 N1 C1 C2 0.4(6) . . . . ? C8 N2 C1 N1 178.1(3) . . . . ? C8 N2 C1 C2 -1.6(5) . . . . ? N1 C1 C2 C3 -1.0(6) . . . . ? N2 C1 C2 C3 178.7(4) . . . . ? N1 C1 C2 C6 179.0(4) . . . . ? N2 C1 C2 C6 -1.3(5) . . . . ? C1 C2 C3 C4 0.1(6) . . . . ? C6 C2 C3 C4 -179.9(4) . . . . ? C1 C2 C3 C10 -178.8(4) . . . . ? C6 C2 C3 C10 1.2(6) . . . . ? C2 C3 C4 C5 1.3(6) . . . . ? C10 C3 C4 C5 -179.8(4) . . . . ? C1 N1 C5 C4 1.0(6) . . . . ? C1 N1 C5 C9 -179.9(4) . . . . ? C3 C4 C5 N1 -1.9(7) . . . . ? C3 C4 C5 C9 179.0(4) . . . . ? C1 C2 C6 C7 1.2(6) . . . . ? C3 C2 C6 C7 -178.8(4) . . . . ? C2 C6 C7 C8 1.8(6) . . . . ? N3 N3 C8 N2 1.5(6) 3_655 . . . ? N3 N3 C8 C7 -179.7(4) 3_655 . . . ? C1 N2 C8 N3 -176.8(4) . . . . ? C1 N2 C8 C7 4.3(5) . . . . ? C6 C7 C8 N3 176.7(4) . . . . ? C6 C7 C8 N2 -4.4(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 HN2 N3 0.894(3) 2.045(3) 2.567(4) 116.1(2) 3_655 N2 HN2 Cl3 0.894(3) 2.923(2) 3.648(4) 139.3(2) 4_655 _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.200 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.044