# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jhy-Der Chen' _publ_contact_author_email JDCHEN@CYCU.EDU.TW _publ_section_title ; Roles of halide anions in the structural diversity of Zn(II) complexes containing the flexible N,N-di(4-pyridyl)adipoamide ligand ; loop_ _publ_author_name 'Jhy-Der Chen.' 'Wen-Jung Chang.' 'Pei-Chi Cheng.' 'Yi-Fen Hsu.' ; Wayne Hsu ; 'Ju-Chun Wang.' 'Chia-Jun Wu.' 'Chun-Wei Yeh.' #===END data_6 _database_code_depnum_ccdc_archive 'CCDC 734436' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H74 I4 N12 O9 Zn2' _chemical_formula_weight 1601.53 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2189(16) _cell_length_b 9.4608(17) _cell_length_c 19.696(3) _cell_angle_alpha 88.101(3) _cell_angle_beta 76.706(4) _cell_angle_gamma 76.982(3) _cell_volume 1628.5(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3570 _cell_measurement_theta_min 2.210 _cell_measurement_theta_max 25.8645 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.633 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 790 _exptl_absorpt_coefficient_mu 2.687 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6959 _exptl_absorpt_correction_T_max 0.9881 _exptl_absorpt_process_details empirical _exptl_special_details ; ? ; _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 '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 9057 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0559 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 26.03 _reflns_number_total 6316 _reflns_number_gt 4242 _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^)+(0.0466P)^2^+5.9824P] 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 6316 _refine_ls_number_parameters 340 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0906 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1447 _refine_ls_wR_factor_gt 0.1255 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.073 _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 Zn Zn 0.48575(10) 1.28170(9) 0.24331(4) 0.0470(2) Uani 1 1 d . . . I1 I 0.39541(8) 1.49905(6) 0.32782(3) 0.0732(2) Uani 1 1 d . . . I2 I 0.75754(6) 1.13014(6) 0.22569(3) 0.0696(2) Uani 1 1 d . . . O1 O 0.0948(6) 0.7344(6) 0.2152(3) 0.0646(14) Uani 1 1 d . . . O2 O -0.4412(7) 0.7479(6) 0.1119(3) 0.0671(15) Uani 1 1 d . . . N1 N 0.3392(7) 1.1444(6) 0.2690(3) 0.0487(14) Uani 1 1 d . . . N2 N 0.0247(7) 0.8807(6) 0.3119(3) 0.0516(15) Uani 1 1 d . . . H2A H -0.0408 0.9005 0.3511 0.062 Uiso 1 1 calc R . . N3 N -0.2971(7) 0.5642(6) 0.0380(3) 0.0475(14) Uani 1 1 d . . . H3A H -0.2271 0.4861 0.0359 0.057 Uiso 1 1 calc R . . N4 N -0.4446(6) 0.6533(6) -0.1478(3) 0.0459(14) Uani 1 1 d . . . C1 C 0.2005(9) 1.1861(9) 0.3114(4) 0.064(2) Uani 1 1 d . . . H1A H 0.1737 1.2782 0.3320 0.077 Uiso 1 1 calc R . . C2 C 0.0976(9) 1.1016(9) 0.3258(4) 0.064(2) Uani 1 1 d . . . H2B H 0.0033 1.1357 0.3562 0.076 Uiso 1 1 calc R . . C3 C 0.1323(8) 0.9634(7) 0.2953(4) 0.0442(16) Uani 1 1 d . . . C4 C 0.2757(8) 0.9189(8) 0.2506(4) 0.0499(17) Uani 1 1 d . . . H4B H 0.3040 0.8282 0.2285 0.060 Uiso 1 1 calc R . . C5 C 0.3744(8) 1.0104(7) 0.2396(4) 0.0498(17) Uani 1 1 d . . . H5A H 0.4707 0.9786 0.2104 0.060 Uiso 1 1 calc R . . C6 C 0.0111(8) 0.7691(7) 0.2721(4) 0.0469(17) Uani 1 1 d . . . C7 C -0.1165(10) 0.6981(9) 0.3069(4) 0.063(2) Uani 1 1 d . . . H7A H -0.2080 0.7728 0.3240 0.076 Uiso 1 1 calc R . . H7B H -0.0892 0.6449 0.3468 0.076 Uiso 1 1 calc R . . C8 C -0.1518(10) 0.5933(8) 0.2578(4) 0.059(2) Uani 1 1 d . . . H8A H -0.0566 0.5315 0.2330 0.071 Uiso 1 1 calc R . . H8B H -0.2128 0.5315 0.2855 0.071 Uiso 1 1 calc R . . C9 C -0.2367(10) 0.6716(8) 0.2053(4) 0.058(2) Uani 1 1 d . . . H9A H -0.3383 0.7217 0.2297 0.070 Uiso 1 1 calc R . . H9B H -0.1835 0.7438 0.1824 0.070 Uiso 1 1 calc R . . C10 C -0.2498(10) 0.5716(8) 0.1520(4) 0.061(2) Uani 1 1 d . . . H10A H -0.2967 0.4959 0.1756 0.073 Uiso 1 1 calc R . . H10B H -0.1476 0.5256 0.1265 0.073 Uiso 1 1 calc R . . C11 C -0.3405(9) 0.6403(8) 0.1004(4) 0.0487(17) Uani 1 1 d . . . C12 C -0.3515(8) 0.5968(7) -0.0221(3) 0.0425(15) Uani 1 1 d . . . C13 C -0.4761(8) 0.7067(8) -0.0266(4) 0.0552(19) Uani 1 1 d . . . H13A H -0.5319 0.7632 0.0125 0.066 Uiso 1 1 calc R . . C14 C -0.5161(8) 0.7313(8) -0.0896(4) 0.0543(19) Uani 1 1 d . . . H14A H -0.5986 0.8073 -0.0919 0.065 Uiso 1 1 calc R . . C15 C -0.3271(9) 0.5428(8) -0.1425(4) 0.0526(19) Uani 1 1 d . . . H15A H -0.2768 0.4846 -0.1818 0.063 Uiso 1 1 calc R . . C16 C -0.2785(9) 0.5122(8) -0.0824(4) 0.0538(19) Uani 1 1 d . . . H16A H -0.1964 0.4348 -0.0813 0.065 Uiso 1 1 calc R . . O3 O -0.0472(8) 0.3160(7) 0.0144(3) 0.0833(19) Uani 1 1 d . . . O4 O 0.2154(11) 2.0098(11) 0.5671(4) 0.126(3) Uani 1 1 d . . . N5 N 0.1274(7) 0.1246(7) 0.0401(4) 0.0657(18) Uani 1 1 d . . . N6 N 0.4049(11) 1.8537(11) 0.4953(4) 0.100(3) Uani 1 1 d . . . C17 C 0.1957(12) 0.0471(13) 0.0955(6) 0.110(4) Uani 1 1 d . . . H17A H 0.1563 0.1025 0.1384 0.165 Uiso 1 1 calc R . . H17B H 0.3048 0.0345 0.0824 0.165 Uiso 1 1 calc R . . H17C H 0.1702 -0.0462 0.1018 0.165 Uiso 1 1 calc R . . C18 C 0.1718(12) 0.0627(11) -0.0293(5) 0.090(3) Uani 1 1 d . . . H18A H 0.1186 0.1256 -0.0592 0.135 Uiso 1 1 calc R . . H18B H 0.1465 -0.0304 -0.0284 0.135 Uiso 1 1 calc R . . H18C H 0.2801 0.0517 -0.0465 0.135 Uiso 1 1 calc R . . C19 C 0.0206(10) 0.2462(9) 0.0548(5) 0.068(2) Uani 1 1 d . . . H19A H -0.0047 0.2813 0.1006 0.082 Uiso 1 1 calc R . . C20 C 0.531(2) 1.7273(18) 0.4869(8) 0.173(8) Uani 1 1 d . . . H20A H 0.5446 1.6932 0.5320 0.260 Uiso 1 1 calc R . . H20B H 0.6230 1.7531 0.4611 0.260 Uiso 1 1 calc R . . H20C H 0.5091 1.6521 0.4620 0.260 Uiso 1 1 calc R . . C21 C 0.380(2) 1.9097(17) 0.4331(7) 0.147(6) Uani 1 1 d . . . H21A H 0.2983 1.9947 0.4415 0.221 Uiso 1 1 calc R . . H21B H 0.3534 1.8386 0.4075 0.221 Uiso 1 1 calc R . . H21C H 0.4716 1.9351 0.4065 0.221 Uiso 1 1 calc R . . C22 C 0.3268(17) 1.9019(17) 0.5579(6) 0.118(4) Uani 1 1 d . . . H22A H 0.3547 1.8546 0.5967 0.141 Uiso 1 1 calc R . . O5 O -0.047(3) 0.519(2) 0.4527(11) 0.30(4) Uiso 0.25 1 d PD . . O5' O -0.110(2) 0.5445(18) 0.481(2) 0.25(3) Uiso 0.25 1 d PD . . C23 C -0.105(2) 0.386(2) 0.4760(14) 0.145(11) Uiso 0.50 1 d PD . . C24 C -0.213(3) 0.363(4) 0.4327(19) 0.36(4) Uiso 0.50 1 d PD . . C25 C 0.025(3) 0.565(2) 0.5070(12) 0.135(10) Uiso 0.50 1 d PD . . C26 C 0.044(3) 0.717(2) 0.4940(15) 0.155(12) Uiso 0.50 1 d PD . . 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 Zn 0.0510(5) 0.0404(4) 0.0476(5) -0.0007(3) -0.0131(4) -0.0042(4) I1 0.1014(5) 0.0563(3) 0.0595(3) -0.0148(3) -0.0135(3) -0.0152(3) I2 0.0534(3) 0.0653(4) 0.0863(4) 0.0095(3) -0.0238(3) 0.0012(2) O1 0.053(3) 0.069(4) 0.065(4) -0.021(3) -0.002(3) -0.008(3) O2 0.069(4) 0.067(4) 0.056(3) -0.020(3) -0.017(3) 0.009(3) N1 0.048(3) 0.039(3) 0.053(3) -0.008(3) -0.004(3) -0.003(3) N2 0.053(4) 0.052(4) 0.048(3) -0.012(3) -0.006(3) -0.010(3) N3 0.051(3) 0.038(3) 0.047(3) -0.003(3) -0.010(3) 0.003(3) N4 0.048(3) 0.040(3) 0.044(3) -0.004(3) -0.012(3) 0.003(3) C1 0.061(5) 0.044(4) 0.075(5) -0.021(4) 0.002(4) -0.004(4) C2 0.049(4) 0.056(5) 0.073(5) -0.027(4) 0.010(4) -0.007(4) C3 0.043(4) 0.040(4) 0.047(4) -0.005(3) -0.012(3) -0.002(3) C4 0.049(4) 0.039(4) 0.055(4) -0.008(3) -0.010(3) 0.005(3) C5 0.051(4) 0.042(4) 0.047(4) -0.004(3) -0.002(3) 0.000(3) C6 0.046(4) 0.043(4) 0.050(4) -0.003(3) -0.017(3) -0.001(3) C7 0.080(6) 0.066(5) 0.053(5) 0.000(4) -0.018(4) -0.033(4) C8 0.071(5) 0.050(4) 0.065(5) 0.007(4) -0.029(4) -0.020(4) C9 0.071(5) 0.041(4) 0.062(5) -0.007(3) -0.019(4) -0.006(4) C10 0.077(6) 0.051(5) 0.056(5) -0.002(4) -0.022(4) -0.009(4) C11 0.057(4) 0.042(4) 0.047(4) -0.002(3) -0.012(3) -0.011(3) C12 0.044(4) 0.038(4) 0.041(4) 0.000(3) -0.009(3) -0.002(3) C13 0.053(4) 0.049(4) 0.050(4) -0.015(3) -0.008(3) 0.015(3) C14 0.047(4) 0.052(4) 0.049(4) -0.010(3) -0.010(3) 0.018(3) C15 0.060(5) 0.044(4) 0.042(4) -0.010(3) -0.011(3) 0.014(3) C16 0.061(5) 0.038(4) 0.051(4) -0.011(3) -0.013(4) 0.015(3) O3 0.093(5) 0.063(4) 0.079(4) 0.003(3) -0.025(4) 0.019(3) O4 0.118(7) 0.136(8) 0.095(6) -0.033(5) 0.024(5) -0.012(6) N5 0.050(4) 0.052(4) 0.083(5) 0.007(4) -0.007(3) 0.004(3) N6 0.104(7) 0.118(8) 0.059(5) -0.012(5) -0.006(5) 0.003(6) C17 0.075(7) 0.114(9) 0.131(10) 0.043(8) -0.041(7) 0.009(6) C18 0.079(7) 0.076(7) 0.099(8) -0.016(6) 0.012(6) -0.013(5) C19 0.067(5) 0.058(5) 0.071(6) -0.001(4) -0.006(4) -0.004(4) C20 0.185(17) 0.155(15) 0.132(13) -0.002(11) -0.022(12) 0.044(13) C21 0.193(16) 0.155(14) 0.087(9) 0.017(9) -0.032(10) -0.030(12) C22 0.128(11) 0.140(12) 0.079(8) -0.017(8) 0.005(8) -0.042(10) _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 Zn N1 2.050(6) . ? Zn N4 2.050(5) 2_575 ? Zn I2 2.5434(10) . ? Zn I1 2.5515(10) . ? O1 C6 1.212(8) . ? O2 C11 1.201(8) . ? N1 C1 1.338(9) . ? N1 C5 1.350(9) . ? N2 C3 1.373(9) . ? N2 C6 1.381(9) . ? N2 H2A 0.8600 . ? N3 C11 1.377(9) . ? N3 C12 1.388(8) . ? N3 H3A 0.8600 . ? N4 C14 1.335(8) . ? N4 C15 1.346(8) . ? N4 Zn 2.050(5) 2_575 ? C1 C2 1.350(11) . ? C1 H1A 0.9300 . ? C2 C3 1.396(10) . ? C2 H2B 0.9300 . ? C3 C4 1.393(10) . ? C4 C5 1.370(10) . ? C4 H4B 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.503(11) . ? C7 C8 1.542(10) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.513(10) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.479(10) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.501(10) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C13 1.383(9) . ? C12 C16 1.398(9) . ? C13 C14 1.373(10) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.360(10) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? O3 C19 1.213(10) . ? O4 C22 1.259(16) . ? N5 C19 1.325(10) . ? N5 C18 1.437(12) . ? N5 C17 1.477(11) . ? N6 C22 1.314(14) . ? N6 C21 1.366(14) . ? N6 C20 1.452(16) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9300 . ? O5 O5' 0.71(5) . ? O5 C25 1.12(3) 2_566 ? O5 C25 1.4999(10) . ? O5 C23 1.4999(11) . ? O5' C25 1.20(3) 2_566 ? O5' C25 1.4999(11) . ? O5' C23 1.4999(11) . ? C23 C25 1.08(3) 2_566 ? C23 C26 1.22(3) 2_566 ? C23 C24 1.4999(10) . ? C25 C23 1.08(3) 2_566 ? C25 O5 1.12(3) 2_566 ? C25 O5' 1.20(3) 2_566 ? C25 C25 1.45(4) 2_566 ? C25 C26 1.5000(11) . ? C26 C23 1.22(3) 2_566 ? 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 Zn N4 99.3(2) . 2_575 ? N1 Zn I2 107.92(16) . . ? N4 Zn I2 108.81(16) 2_575 . ? N1 Zn I1 109.40(15) . . ? N4 Zn I1 109.20(15) 2_575 . ? I2 Zn I1 120.16(4) . . ? C1 N1 C5 116.8(6) . . ? C1 N1 Zn 122.0(5) . . ? C5 N1 Zn 121.0(5) . . ? C3 N2 C6 126.6(6) . . ? C3 N2 H2A 116.7 . . ? C6 N2 H2A 116.7 . . ? C11 N3 C12 128.6(6) . . ? C11 N3 H3A 115.7 . . ? C12 N3 H3A 115.7 . . ? C14 N4 C15 116.3(6) . . ? C14 N4 Zn 121.8(4) . 2_575 ? C15 N4 Zn 121.0(4) . 2_575 ? N1 C1 C2 123.5(7) . . ? N1 C1 H1A 118.3 . . ? C2 C1 H1A 118.3 . . ? C1 C2 C3 120.2(7) . . ? C1 C2 H2B 119.9 . . ? C3 C2 H2B 119.9 . . ? N2 C3 C4 124.7(6) . . ? N2 C3 C2 118.3(6) . . ? C4 C3 C2 117.0(7) . . ? C5 C4 C3 119.1(6) . . ? C5 C4 H4B 120.5 . . ? C3 C4 H4B 120.5 . . ? N1 C5 C4 123.4(6) . . ? N1 C5 H5A 118.3 . . ? C4 C5 H5A 118.3 . . ? O1 C6 N2 122.3(7) . . ? O1 C6 C7 124.9(7) . . ? N2 C6 C7 112.8(6) . . ? C6 C7 C8 113.1(7) . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C7 112.7(6) . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C8 112.3(6) . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9B 109.1 . . ? C8 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C9 C10 C11 115.4(6) . . ? C9 C10 H10A 108.4 . . ? C11 C10 H10A 108.4 . . ? C9 C10 H10B 108.4 . . ? C11 C10 H10B 108.4 . . ? H10A C10 H10B 107.5 . . ? O2 C11 N3 123.1(7) . . ? O2 C11 C10 124.6(7) . . ? N3 C11 C10 112.2(6) . . ? C13 C12 N3 124.4(6) . . ? C13 C12 C16 116.9(6) . . ? N3 C12 C16 118.6(6) . . ? C14 C13 C12 119.0(6) . . ? C14 C13 H13A 120.5 . . ? C12 C13 H13A 120.5 . . ? N4 C14 C13 124.4(6) . . ? N4 C14 H14A 117.8 . . ? C13 C14 H14A 117.8 . . ? N4 C15 C16 123.1(6) . . ? N4 C15 H15A 118.4 . . ? C16 C15 H15A 118.4 . . ? C15 C16 C12 120.1(6) . . ? C15 C16 H16A 119.9 . . ? C12 C16 H16A 119.9 . . ? C19 N5 C18 120.2(8) . . ? C19 N5 C17 120.4(8) . . ? C18 N5 C17 119.3(8) . . ? C22 N6 C21 126.7(13) . . ? C22 N6 C20 120.5(12) . . ? C21 N6 C20 112.8(11) . . ? N5 C17 H17A 109.5 . . ? N5 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N5 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N5 C18 H18A 109.5 . . ? N5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O3 C19 N5 126.2(9) . . ? O3 C19 H19A 116.9 . . ? N5 C19 H19A 116.9 . . ? N6 C20 H20A 109.5 . . ? N6 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N6 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N6 C21 H21A 109.5 . . ? N6 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N6 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O4 C22 N6 122.2(14) . . ? O4 C22 H22A 118.9 . . ? N6 C22 H22A 118.9 . . ? O5' O5 C25 78(3) . 2_566 ? O5' O5 C25 76.2(9) . . ? C25 O5 C25 65.5(19) 2_566 . ? O5' O5 C23 76.2(9) . . ? C25 O5 C23 45.9(18) 2_566 . ? C25 O5 C23 109.52(10) . . ? O5 O5' C25 66(3) . 2_566 ? O5 O5' C25 76.2(9) . . ? C25 O5' C25 64.0(17) 2_566 . ? O5 O5' C23 76.2(9) . . ? C25 O5' C23 45.5(17) 2_566 . ? C25 O5' C23 109.52(10) . . ? C25 C23 C26 81.2(19) 2_566 2_566 ? C25 C23 C24 157.8(19) 2_566 . ? C26 C23 C24 119.1(17) 2_566 . ? C25 C23 O5 48.3(18) 2_566 . ? C26 C23 O5 127.1(18) 2_566 . ? C24 C23 O5 109.51(10) . . ? C25 C23 O5' 52.6(17) 2_566 . ? C26 C23 O5' 130.8(19) 2_566 . ? C24 C23 O5' 109.51(10) . . ? O5 C23 O5' 27.5(18) . . ? C23 C25 O5 86(2) 2_566 2_566 ? C23 C25 O5' 82(2) 2_566 2_566 ? O5 C25 O5' 36(3) 2_566 2_566 ? C23 C25 C25 150(3) 2_566 2_566 ? O5 C25 C25 69.8(18) 2_566 2_566 ? O5' C25 C25 68.0(17) 2_566 2_566 ? C23 C25 O5 153(3) 2_566 . ? O5 C25 O5 114.5(18) 2_566 . ? O5' C25 O5 104(2) 2_566 . ? C25 C25 O5 44.7(14) 2_566 . ? C23 C25 O5' 162.1(17) 2_566 . ? O5 C25 O5' 109(2) 2_566 . ? O5' C25 O5' 116.0(17) 2_566 . ? C25 C25 O5' 48.0(12) 2_566 . ? O5 C25 O5' 27.5(18) . . ? C23 C25 C26 53.4(16) 2_566 . ? O5 C25 C26 136.0(19) 2_566 . ? O5' C25 C26 132.2(18) 2_566 . ? C25 C25 C26 154.1(13) 2_566 . ? O5 C25 C26 109.50(10) . . ? O5' C25 C26 109.51(10) . . ? C23 C26 C25 45.4(16) 2_566 . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.788 _refine_diff_density_min -1.046 _refine_diff_density_rms 0.112 #===END # Attachment 'all.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 734437' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 Cl2 N4 O3 Zn' _chemical_formula_weight 452.63 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' Cl Cl 0.1484 0.1585 '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 Orthorhombic _symmetry_space_group_name_H-M Ccca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x, y, -z+1/2' 'x+1/2, -y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1, -y+1/2, z' '-x+1/2, y+1/2, -z+1/2' 'x+1, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x, -y, z-1/2' '-x-1/2, y, z-1/2' '-x+1/2, -y+1/2, -z' 'x, y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' '-x, y+1/2, z-1/2' _cell_length_a 15.3104(12) _cell_length_b 17.8384(13) _cell_length_c 14.6419(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3998.9(5) _cell_formula_units_Z 8 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 5310 _cell_measurement_theta_min 2.663 _cell_measurement_theta_max 26.006 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.67 _exptl_crystal_size_mid 0.51 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 1.518 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.597 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details empirical _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 10743 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 26.01 _reflns_number_total 1975 _reflns_number_gt 1628 _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^)+(0.0500P)^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 _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1975 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0859 _refine_ls_wR_factor_gt 0.0814 _refine_ls_goodness_of_fit_ref 1.210 _refine_ls_restrained_S_all 1.210 _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 Zn Zn 0.0000 0.038241(17) 0.7500 0.03405(14) Uani 1 2 d S . . Cl Cl 0.05549(4) 0.10687(4) 0.63673(4) 0.0589(2) Uani 1 1 d . . . O1 O 0.30640(12) -0.13354(12) 1.05482(12) 0.0803(7) Uani 1 1 d . . . N1 N 0.09343(10) -0.02808(9) 0.80507(11) 0.0370(4) Uani 1 1 d . . . N2 N 0.29600(11) -0.16305(11) 0.90469(12) 0.0435(4) Uani 1 1 d . . . H2A H 0.3186(14) -0.1858(12) 0.8613(15) 0.045(6) Uiso 1 1 d . . . C1 C 0.11117(13) -0.03068(11) 0.89484(13) 0.0381(5) Uani 1 1 d . . . H1A H 0.0769 -0.0020 0.9339 0.046 Uiso 1 1 calc R . . C2 C 0.17686(13) -0.07309(11) 0.93268(13) 0.0389(5) Uani 1 1 d . . . H2C H 0.1868 -0.0726 0.9953 0.047 Uiso 1 1 calc R . . C3 C 0.22817(12) -0.11678(11) 0.87489(13) 0.0363(4) Uani 1 1 d . . . C4 C 0.21014(15) -0.11459(14) 0.78191(15) 0.0522(6) Uani 1 1 d . . . H4A H 0.2429 -0.1433 0.7415 0.063 Uiso 1 1 calc R . . C5 C 0.14395(17) -0.06993(16) 0.74999(13) 0.0514(6) Uani 1 1 d . . . H5A H 0.1336 -0.0685 0.6874 0.062 Uiso 1 1 calc R . . C6 C 0.33160(13) -0.16956(12) 0.99048(13) 0.0413(5) Uani 1 1 d . . . C7 C 0.40339(14) -0.22723(12) 0.99579(15) 0.0404(5) Uani 1 1 d . . . H7A H 0.4382 -0.2239 0.9406 0.048 Uiso 1 1 calc R . . H7B H 0.3769 -0.2766 0.9970 0.048 Uiso 1 1 calc R . . C8 C 0.46365(15) -0.22019(15) 1.07713(15) 0.0502(6) Uani 1 1 d . . . H8A H 0.4297 -0.2250 1.1328 0.060 Uiso 1 1 calc R . . H8B H 0.4900 -0.1708 1.0769 0.060 Uiso 1 1 calc R . . O2 O 0.37487(19) -0.2500 0.7500 0.0519(6) Uani 1 2 d S . . H2B H 0.4051(18) -0.2203(16) 0.729(2) 0.064(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn 0.0363(2) 0.0342(2) 0.0316(2) 0.000 -0.00113(12) 0.000 Cl 0.0714(4) 0.0587(4) 0.0466(3) 0.0137(3) 0.0075(3) -0.0154(3) O1 0.0844(13) 0.1174(16) 0.0391(9) -0.0301(10) -0.0193(9) 0.0626(12) N1 0.0373(9) 0.0402(9) 0.0334(9) -0.0023(7) -0.0035(7) 0.0046(7) N2 0.0446(10) 0.0541(11) 0.0317(9) -0.0098(8) -0.0023(8) 0.0180(8) C1 0.0387(11) 0.0431(11) 0.0325(10) -0.0036(8) 0.0039(8) 0.0063(8) C2 0.0395(10) 0.0489(12) 0.0282(10) -0.0015(9) 0.0002(8) 0.0063(9) C3 0.0352(10) 0.0410(12) 0.0326(10) -0.0035(8) -0.0017(8) 0.0036(8) C4 0.0556(13) 0.0677(16) 0.0334(11) -0.0122(10) -0.0023(10) 0.0261(11) C5 0.0589(15) 0.0655(16) 0.0297(11) -0.0094(9) -0.0059(9) 0.0181(13) C6 0.0402(10) 0.0503(12) 0.0334(11) -0.0034(9) -0.0025(9) 0.0095(9) C7 0.0373(11) 0.0447(11) 0.0391(11) -0.0034(9) -0.0021(9) 0.0088(9) C8 0.0468(12) 0.0708(15) 0.0329(12) -0.0049(10) -0.0008(10) 0.0226(12) O2 0.0574(16) 0.0525(16) 0.0460(15) -0.0057(11) 0.000 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 Zn N1 2.0238(16) 3_556 ? Zn N1 2.0238(16) . ? Zn Cl 2.2296(6) 3_556 ? Zn Cl 2.2296(6) . ? O1 C6 1.204(2) . ? N1 C1 1.343(3) . ? N1 C5 1.344(3) . ? N2 C6 1.374(2) . ? N2 C3 1.396(2) . ? N2 H2A 0.83(2) . ? C1 C2 1.375(3) . ? C1 H1A 0.9300 . ? C2 C3 1.393(3) . ? C2 H2C 0.9300 . ? C3 C4 1.390(3) . ? C4 C5 1.371(3) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.508(3) . ? C7 C8 1.512(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C8 1.539(4) 6_545 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? O2 H2B 0.77(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 N1 Zn N1 108.45(9) 3_556 . ? N1 Zn Cl 110.37(5) 3_556 3_556 ? N1 Zn Cl 107.10(5) . 3_556 ? N1 Zn Cl 107.10(5) 3_556 . ? N1 Zn Cl 110.37(5) . . ? Cl Zn Cl 113.39(4) 3_556 . ? C1 N1 C5 116.85(17) . . ? C1 N1 Zn 123.58(13) . . ? C5 N1 Zn 119.51(14) . . ? C6 N2 C3 129.08(17) . . ? C6 N2 H2A 119.6(15) . . ? C3 N2 H2A 111.1(15) . . ? N1 C1 C2 124.14(18) . . ? N1 C1 H1A 117.9 . . ? C2 C1 H1A 117.9 . . ? C1 C2 C3 118.40(18) . . ? C1 C2 H2C 120.8 . . ? C3 C2 H2C 120.8 . . ? C4 C3 C2 117.85(18) . . ? C4 C3 N2 118.06(17) . . ? C2 C3 N2 124.08(18) . . ? C5 C4 C3 119.81(19) . . ? C5 C4 H4A 120.1 . . ? C3 C4 H4A 120.1 . . ? N1 C5 C4 122.93(19) . . ? N1 C5 H5A 118.5 . . ? C4 C5 H5A 118.5 . . ? O1 C6 N2 122.90(19) . . ? O1 C6 C7 123.89(19) . . ? N2 C6 C7 113.20(17) . . ? C6 C7 C8 115.40(17) . . ? C6 C7 H7A 108.4 . . ? C8 C7 H7A 108.4 . . ? C6 C7 H7B 108.4 . . ? C8 C7 H7B 108.4 . . ? H7A C7 H7B 107.5 . . ? C7 C8 C8 112.57(18) . 6_545 ? C7 C8 H8A 109.1 . . ? C8 C8 H8A 109.1 6_545 . ? C7 C8 H8B 109.1 . . ? C8 C8 H8B 109.1 6_545 . ? H8A C8 H8B 107.8 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.312 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.052 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 734438' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 Br2 N4 O3 Zn' _chemical_formula_weight 541.55 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Ccca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x, y, -z+1/2' 'x+1/2, -y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1, -y+1/2, z' '-x+1/2, y+1/2, -z+1/2' 'x+1, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x, -y, z-1/2' '-x-1/2, y, z-1/2' '-x+1/2, -y+1/2, -z' 'x, y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' '-x, y+1/2, z-1/2' _cell_length_a 15.3196(16) _cell_length_b 18.1947(13) _cell_length_c 14.8493(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4139.0(6) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 5.91 _cell_measurement_theta_max 12.49 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.738 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2144 _exptl_absorpt_coefficient_mu 5.070 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4120 _exptl_absorpt_correction_T_max 0.8232 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2244 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1800 _reflns_number_gt 1261 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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^)+(0.0412P)^2^+15.2569P] 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 1800 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1010 _refine_ls_wR_factor_gt 0.0881 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 Zn Zn 0.5000 0.52945(5) 0.7500 0.0367(2) Uani 1 2 d S . . Br Br 0.44216(4) 0.60147(4) 0.86777(4) 0.0610(2) Uani 1 1 d . . . O1 O 0.8083(3) 0.3660(3) 1.0501(3) 0.0886(17) Uani 1 1 d . . . N1 N 0.5947(2) 0.4653(2) 0.8038(3) 0.0365(10) Uani 1 1 d . . . N2 N 0.7982(3) 0.3352(3) 0.9029(3) 0.0470(12) Uani 1 1 d . . . H2A H 0.8209 0.3070 0.8628 0.056 Uiso 1 1 calc R . . C5 C 0.6442(4) 0.4229(3) 0.7501(4) 0.0549(15) Uani 1 1 d . . . H1A H 0.6324 0.4226 0.6886 0.066 Uiso 1 1 calc R . . C4 C 0.7113(4) 0.3802(4) 0.7815(4) 0.0570(17) Uani 1 1 d . . . H2B H 0.7438 0.3514 0.7420 0.068 Uiso 1 1 calc R . . C3 C 0.7303(3) 0.3803(3) 0.8731(3) 0.0403(13) Uani 1 1 d . . . C2 C 0.6802(3) 0.4245(3) 0.9279(3) 0.0416(13) Uani 1 1 d . . . H4A H 0.6914 0.4269 0.9894 0.050 Uiso 1 1 calc R . . C1 C 0.6144(3) 0.4646(3) 0.8913(3) 0.0425(13) Uani 1 1 d . . . H5A H 0.5809 0.4934 0.9298 0.051 Uiso 1 1 calc R . . C6 C 0.8338(3) 0.3297(3) 0.9879(3) 0.0469(14) Uani 1 1 d . . . C7 C 0.9028(3) 0.2718(3) 0.9946(3) 0.0431(13) Uani 1 1 d . . . H7A H 0.9372 0.2726 0.9397 0.052 Uiso 1 1 calc R . . H7B H 0.8746 0.2242 0.9982 0.052 Uiso 1 1 calc R . . C8 C 0.9638(3) 0.2795(4) 1.0738(3) 0.0511(15) Uani 1 1 d . . . H8A H 0.9305 0.2757 1.1291 0.061 Uiso 1 1 calc R . . H8B H 0.9905 0.3278 1.0723 0.061 Uiso 1 1 calc R . . O2 O 0.8774(4) 0.2500 0.7500 0.0546(15) Uani 1 2 d S . . H2O1 H 0.907(4) 0.218(3) 0.775(4) 0.06(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn 0.0361(4) 0.0381(5) 0.0358(4) 0.000 -0.0015(4) 0.000 Br 0.0712(4) 0.0634(4) 0.0485(3) -0.0131(3) 0.0071(3) 0.0175(3) O1 0.087(3) 0.131(4) 0.048(2) -0.034(3) -0.023(2) 0.068(3) N1 0.034(2) 0.043(3) 0.033(2) -0.003(2) -0.0038(18) 0.004(2) N2 0.043(3) 0.059(3) 0.039(2) -0.010(2) -0.004(2) 0.019(2) C5 0.064(4) 0.069(4) 0.033(3) -0.012(3) 0.000(3) 0.020(3) C4 0.054(4) 0.074(4) 0.043(3) -0.015(3) 0.000(3) 0.026(3) C3 0.038(3) 0.043(3) 0.040(3) -0.004(2) -0.001(2) 0.005(2) C2 0.040(3) 0.054(4) 0.031(2) -0.002(2) -0.001(2) 0.012(3) C1 0.043(3) 0.054(3) 0.031(3) -0.004(2) 0.003(2) 0.013(3) C6 0.044(3) 0.056(4) 0.040(3) -0.005(3) -0.004(3) 0.011(3) C7 0.038(3) 0.048(3) 0.042(3) -0.005(3) -0.001(2) 0.007(3) C8 0.046(3) 0.072(4) 0.036(3) -0.004(3) -0.001(2) 0.024(3) O2 0.061(4) 0.056(4) 0.047(3) -0.004(3) 0.000 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 Zn N1 2.026(4) 3_656 ? Zn N1 2.026(4) . ? Zn Br 2.3581(7) . ? Zn Br 2.3581(7) 3_656 ? O1 C6 1.201(6) . ? N1 C1 1.335(6) . ? N1 C5 1.344(6) . ? N2 C6 1.377(6) . ? N2 C3 1.398(6) . ? N2 H2A 0.8600 . ? C5 C4 1.370(8) . ? C5 H1A 0.9300 . ? C4 C3 1.391(7) . ? C4 H2B 0.9300 . ? C3 C2 1.377(7) . ? C2 C1 1.357(7) . ? C2 H4A 0.9300 . ? C1 H5A 0.9300 . ? C6 C7 1.496(7) . ? C7 C8 1.508(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C8 1.544(10) 6_655 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? O2 H2O1 0.83(5) . ? 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 Zn N1 109.7(2) 3_656 . ? N1 Zn Br 110.07(11) 3_656 . ? N1 Zn Br 107.27(11) . . ? N1 Zn Br 107.27(11) 3_656 3_656 ? N1 Zn Br 110.07(11) . 3_656 ? Br Zn Br 112.48(5) . 3_656 ? C1 N1 C5 116.4(4) . . ? C1 N1 Zn 123.5(3) . . ? C5 N1 Zn 120.1(3) . . ? C6 N2 C3 128.9(4) . . ? C6 N2 H2A 115.6 . . ? C3 N2 H2A 115.6 . . ? N1 C5 C4 123.1(5) . . ? N1 C5 H1A 118.4 . . ? C4 C5 H1A 118.4 . . ? C5 C4 C3 119.3(5) . . ? C5 C4 H2B 120.4 . . ? C3 C4 H2B 120.4 . . ? C2 C3 C4 117.5(5) . . ? C2 C3 N2 124.8(4) . . ? C4 C3 N2 117.7(5) . . ? C1 C2 C3 119.4(5) . . ? C1 C2 H4A 120.3 . . ? C3 C2 H4A 120.3 . . ? N1 C1 C2 124.3(5) . . ? N1 C1 H5A 117.9 . . ? C2 C1 H5A 117.9 . . ? O1 C6 N2 122.4(5) . . ? O1 C6 C7 124.4(5) . . ? N2 C6 C7 113.1(4) . . ? C6 C7 C8 115.1(4) . . ? C6 C7 H7A 108.5 . . ? C8 C7 H7A 108.5 . . ? C6 C7 H7B 108.5 . . ? C8 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C7 C8 C8 112.3(4) . 6_655 ? C7 C8 H8A 109.1 . . ? C8 C8 H8A 109.1 6_655 . ? C7 C8 H8B 109.1 . . ? C8 C8 H8B 109.1 6_655 . ? H8A C8 H8B 107.9 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.493 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.092 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 734439' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 I2 N4 O3 Zn' _chemical_formula_weight 635.53 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' I I -0.4742 1.8119 '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 9.3270(11) _cell_length_b 9.9752(12) _cell_length_c 22.896(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.813(11) _cell_angle_gamma 90.00 _cell_volume 2129.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 5.32 _cell_measurement_theta_max 12.35 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.983 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 4.075 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4666 _exptl_absorpt_correction_T_max 0.9908 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4415 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0772 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3688 _reflns_number_gt 2257 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _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^)+(0.0685P)^2^+3.0519P] 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 3688 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1140 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.1514 _refine_ls_wR_factor_gt 0.1300 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 Zn Zn 0.25565(13) 0.74363(12) 0.46191(5) 0.0448(3) Uani 1 1 d . . . I1 I 0.08409(9) 0.59413(8) 0.40202(3) 0.0585(3) Uani 1 1 d . . . I2 I 0.42976(9) 0.89923(8) 0.41174(3) 0.0595(3) Uani 1 1 d . . . O1 O -0.1437(10) 0.9041(8) 0.7110(4) 0.076(3) Uani 1 1 d . . . O2 O -0.3458(9) 1.5578(9) 0.7201(4) 0.070(2) Uani 1 1 d . . . O3 O -0.2415(8) 1.7431(7) 0.7994(3) 0.0537(19) Uani 1 1 d . . . H3OA H -0.2770 1.6935 0.7681 0.064 Uiso 1 1 d R . . N1 N 0.1438(9) 0.8553(8) 0.5214(4) 0.041(2) Uani 1 1 d . . . N2 N -0.0054(10) 1.0579(8) 0.6676(4) 0.050(2) Uani 1 1 d . . . H2A H 0.0272 1.1383 0.6709 0.060 Uiso 1 1 calc R . . N3 N -0.5150(9) 1.4256(8) 0.6776(4) 0.045(2) Uani 1 1 d . . . H3A H -0.5602 1.3510 0.6812 0.054 Uiso 1 1 calc R . . N4 N -0.6390(10) 1.6263(8) 0.5238(4) 0.046(2) Uani 1 1 d . . . C1 C 0.1898(12) 0.9758(11) 0.5379(5) 0.051(3) Uani 1 1 d . . . H1A H 0.2606 1.0159 0.5161 0.062 Uiso 1 1 calc R . . C2 C 0.1414(12) 1.0436(11) 0.5836(5) 0.053(3) Uani 1 1 d . . . H2B H 0.1776 1.1283 0.5924 0.064 Uiso 1 1 calc R . . C3 C 0.0352(11) 0.9862(10) 0.6183(4) 0.042(3) Uani 1 1 d . . . C4 C -0.0185(11) 0.8615(11) 0.5999(5) 0.049(3) Uani 1 1 d . . . H4B H -0.0917 0.8205 0.6201 0.058 Uiso 1 1 calc R . . C5 C 0.0371(12) 0.8004(11) 0.5523(5) 0.052(3) Uani 1 1 d . . . H5A H 0.0001 0.7177 0.5406 0.062 Uiso 1 1 calc R . . C6 C -0.0903(12) 1.0154(11) 0.7110(5) 0.050(3) Uani 1 1 d . . . C7 C -0.1133(13) 1.1160(11) 0.7582(5) 0.058(3) Uani 1 1 d . . . H7A H -0.0319 1.1764 0.7612 0.069 Uiso 1 1 calc R . . H7B H -0.1216 1.0705 0.7954 0.069 Uiso 1 1 calc R . . C8 C -0.2512(13) 1.1966(12) 0.7442(5) 0.059(3) Uani 1 1 d . . . H8A H -0.2427 1.2396 0.7065 0.071 Uiso 1 1 calc R . . H8B H -0.3318 1.1352 0.7414 0.071 Uiso 1 1 calc R . . C9 C -0.2811(12) 1.3004(11) 0.7887(5) 0.056(3) Uani 1 1 d . . . H9A H -0.2039 1.3657 0.7898 0.067 Uiso 1 1 calc R . . H9B H -0.2846 1.2588 0.8269 0.067 Uiso 1 1 calc R . . C10 C -0.4230(13) 1.3716(11) 0.7749(5) 0.057(3) Uani 1 1 d . . . H10A H -0.4976 1.3045 0.7697 0.069 Uiso 1 1 calc R . . H10B H -0.4470 1.4262 0.8082 0.069 Uiso 1 1 calc R . . C11 C -0.4235(11) 1.4569(10) 0.7229(5) 0.042(2) Uani 1 1 d . . . C12 C -0.5464(11) 1.4958(10) 0.6264(5) 0.043(3) Uani 1 1 d . . . C13 C -0.6576(13) 1.4470(11) 0.5928(5) 0.061(3) Uani 1 1 d . . . H13A H -0.7036 1.3684 0.6035 0.073 Uiso 1 1 calc R . . C14 C -0.7018(11) 1.5147(11) 0.5428(5) 0.051(3) Uani 1 1 d . . . H14A H -0.7797 1.4808 0.5211 0.061 Uiso 1 1 calc R . . C15 C -0.5294(12) 1.6705(12) 0.5560(5) 0.053(3) Uani 1 1 d . . . H15A H -0.4831 1.7478 0.5438 0.063 Uiso 1 1 calc R . . C16 C -0.4777(12) 1.6082(12) 0.6076(5) 0.056(3) Uani 1 1 d . . . H16A H -0.3989 1.6426 0.6285 0.067 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 Zn 0.0508(7) 0.0481(7) 0.0362(7) 0.0009(6) 0.0103(6) -0.0013(6) I1 0.0661(5) 0.0576(5) 0.0516(5) -0.0011(4) -0.0018(4) -0.0101(4) I2 0.0680(5) 0.0672(5) 0.0444(5) -0.0003(4) 0.0201(4) -0.0175(4) O1 0.107(7) 0.058(5) 0.064(6) 0.000(4) 0.038(5) -0.012(5) O2 0.082(6) 0.070(6) 0.059(5) -0.002(4) -0.002(5) -0.011(5) O3 0.066(5) 0.053(4) 0.043(4) -0.005(4) 0.004(4) -0.006(4) N1 0.039(5) 0.049(5) 0.035(5) -0.002(4) 0.008(4) -0.002(4) N2 0.067(6) 0.046(5) 0.038(5) 0.001(4) 0.020(5) -0.001(4) N3 0.060(6) 0.035(5) 0.041(5) 0.000(4) 0.005(5) 0.002(4) N4 0.048(5) 0.051(5) 0.040(5) 0.000(4) 0.006(4) -0.009(4) C1 0.059(7) 0.050(7) 0.046(7) 0.004(6) 0.026(6) 0.002(6) C2 0.060(7) 0.055(6) 0.045(7) -0.004(6) 0.015(6) -0.023(6) C3 0.051(6) 0.040(6) 0.037(6) 0.002(5) 0.022(5) 0.008(5) C4 0.042(6) 0.052(7) 0.053(7) 0.006(5) 0.022(5) 0.005(5) C5 0.056(7) 0.045(6) 0.054(7) -0.008(5) 0.013(6) -0.018(5) C6 0.052(7) 0.040(6) 0.058(8) 0.009(6) 0.013(6) 0.012(5) C7 0.069(8) 0.061(7) 0.045(7) -0.005(6) 0.028(6) -0.001(6) C8 0.061(8) 0.073(8) 0.044(7) 0.007(6) 0.017(6) 0.002(6) C9 0.057(7) 0.059(7) 0.052(7) -0.003(6) 0.003(6) 0.010(6) C10 0.071(8) 0.060(7) 0.042(7) -0.010(6) 0.003(6) 0.003(6) C11 0.044(6) 0.041(6) 0.041(6) -0.018(5) -0.002(5) 0.001(5) C12 0.049(6) 0.044(6) 0.038(6) -0.002(5) 0.009(5) 0.000(5) C13 0.071(8) 0.042(6) 0.068(9) -0.002(6) -0.001(7) -0.013(6) C14 0.044(7) 0.062(7) 0.047(7) -0.004(6) 0.001(6) -0.010(6) C15 0.045(7) 0.061(7) 0.052(7) 0.001(6) 0.013(6) -0.012(6) C16 0.050(7) 0.081(9) 0.037(6) 0.001(6) 0.006(5) -0.005(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 Zn N1 2.068(8) . ? Zn N4 2.063(9) 1_645 ? Zn I2 2.5463(14) . ? Zn I1 2.5545(15) . ? O1 C6 1.217(12) . ? O2 C11 1.242(12) . ? O3 H3OA 0.9236 . ? N1 C1 1.327(13) . ? N1 C5 1.355(13) . ? N2 C6 1.356(13) . ? N2 C3 1.399(12) . ? N2 H2A 0.8600 . ? N3 C11 1.358(13) . ? N3 C12 1.389(13) . ? N3 H3A 0.8600 . ? N4 C15 1.318(14) . ? N4 C14 1.337(13) . ? N4 Zn 2.063(9) 1_465 ? C1 C2 1.336(15) . ? C1 H1A 0.9300 . ? C2 C3 1.411(14) . ? C2 H2B 0.9300 . ? C3 C4 1.401(15) . ? C4 C5 1.366(15) . ? C4 H4B 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.496(15) . ? C7 C8 1.541(16) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.484(15) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.526(15) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.464(15) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C13 1.361(15) . ? C12 C16 1.367(15) . ? C13 C14 1.381(15) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.408(16) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn N4 95.3(3) . 1_645 ? N1 Zn I2 108.1(2) . . ? N4 Zn I2 111.0(2) 1_645 . ? N1 Zn I1 110.4(2) . . ? N4 Zn I1 108.3(2) 1_645 . ? I2 Zn I1 120.75(5) . . ? C1 N1 C5 117.0(9) . . ? C1 N1 Zn 120.7(7) . . ? C5 N1 Zn 121.3(7) . . ? C6 N2 C3 127.6(9) . . ? C6 N2 H2A 116.2 . . ? C3 N2 H2A 116.2 . . ? C11 N3 C12 129.7(9) . . ? C11 N3 H3A 115.2 . . ? C12 N3 H3A 115.2 . . ? C15 N4 C14 115.9(9) . . ? C15 N4 Zn 122.6(7) . 1_465 ? C14 N4 Zn 119.5(7) . 1_465 ? N1 C1 C2 124.5(10) . . ? N1 C1 H1A 117.7 . . ? C2 C1 H1A 117.7 . . ? C1 C2 C3 119.8(10) . . ? C1 C2 H2B 120.1 . . ? C3 C2 H2B 120.1 . . ? N2 C3 C4 126.4(9) . . ? N2 C3 C2 117.4(9) . . ? C4 C3 C2 116.2(9) . . ? C5 C4 C3 119.7(10) . . ? C5 C4 H4B 120.2 . . ? C3 C4 H4B 120.2 . . ? N1 C5 C4 122.7(10) . . ? N1 C5 H5A 118.7 . . ? C4 C5 H5A 118.7 . . ? O1 C6 N2 122.2(10) . . ? O1 C6 C7 123.0(11) . . ? N2 C6 C7 114.8(10) . . ? C6 C7 C8 109.8(10) . . ? C6 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? C6 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C9 C8 C7 113.3(10) . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C8 C9 C10 111.3(10) . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C9 114.8(10) . . ? C11 C10 H10A 108.6 . . ? C9 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? C9 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? O2 C11 N3 120.1(10) . . ? O2 C11 C10 121.7(10) . . ? N3 C11 C10 118.2(10) . . ? C13 C12 C16 118.2(10) . . ? C13 C12 N3 115.7(10) . . ? C16 C12 N3 126.2(10) . . ? C12 C13 C14 119.7(11) . . ? C12 C13 H13A 120.2 . . ? C14 C13 H13A 120.2 . . ? N4 C14 C13 123.7(10) . . ? N4 C14 H14A 118.2 . . ? C13 C14 H14A 118.2 . . ? N4 C15 C16 124.1(10) . . ? N4 C15 H15A 117.9 . . ? C16 C15 H15A 117.9 . . ? C12 C16 C15 118.4(11) . . ? C12 C16 H16A 120.8 . . ? C15 C16 H16A 120.8 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.047 _refine_diff_density_min -1.079 _refine_diff_density_rms 0.156 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 734440' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H50 Cl4 N10 O6 Zn2' _chemical_formula_weight 1015.42 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.9172(5) _cell_length_b 23.3476(15) _cell_length_c 12.7571(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.8200(10) _cell_angle_gamma 90.00 _cell_volume 2316.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 5533 _cell_measurement_theta_min 2.384 _cell_measurement_theta_max 25.920 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 1.320 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.414 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details empirical _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 12988 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 26.02 _reflns_number_total 4558 _reflns_number_gt 3534 _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^)+(0.0650P)^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 4558 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.1014 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 Zn Zn 0.07344(4) 0.181970(12) 0.74792(2) 0.04235(12) Uani 1 1 d . . . Cl1 Cl 0.35002(9) 0.16019(3) 0.75118(7) 0.0582(2) Uani 1 1 d . . . Cl2 Cl -0.02363(11) 0.26207(3) 0.66638(6) 0.0664(2) Uani 1 1 d . . . O1 O -0.6376(3) -0.00799(8) 0.6360(2) 0.0704(6) Uani 1 1 d . . . O2 O -1.1573(3) -0.13520(9) 0.69103(16) 0.0630(6) Uani 1 1 d . . . N1 N -0.0695(3) 0.11253(9) 0.69198(16) 0.0428(5) Uani 1 1 d . . . N2 N -0.3647(3) -0.03609(9) 0.62944(18) 0.0468(5) Uani 1 1 d . . . H2A H -0.3064 -0.0656 0.6173 0.056 Uiso 1 1 calc R . . N3 N -1.0050(3) -0.20890(10) 0.77684(17) 0.0495(5) Uani 1 1 d . . . H3A H -0.9478 -0.2389 0.7659 0.059 Uiso 1 1 calc R . . N4 N -1.0424(3) -0.18838(9) 1.09716(18) 0.0447(5) Uani 1 1 d . . . C1 C -0.0007(3) 0.06185(11) 0.6734(2) 0.0466(6) Uani 1 1 d . . . H1A H 0.1174 0.0597 0.6760 0.056 Uiso 1 1 calc R . . C2 C -0.0977(3) 0.01312(11) 0.6506(2) 0.0475(6) Uani 1 1 d . . . H2B H -0.0449 -0.0211 0.6378 0.057 Uiso 1 1 calc R . . C3 C -0.2734(3) 0.01454(10) 0.6466(2) 0.0401(6) Uani 1 1 d . . . C4 C -0.3471(3) 0.06755(11) 0.6617(2) 0.0494(6) Uani 1 1 d . . . H4B H -0.4654 0.0712 0.6563 0.059 Uiso 1 1 calc R . . C5 C -0.2411(3) 0.11417(11) 0.6848(2) 0.0502(7) Uani 1 1 d . . . H5A H -0.2911 0.1491 0.6962 0.060 Uiso 1 1 calc R . . C6 C -0.5350(3) -0.04566(11) 0.6291(2) 0.0475(6) Uani 1 1 d . . . C7 C -0.5829(3) -0.10846(11) 0.6191(2) 0.0495(6) Uani 1 1 d . . . H7A H -0.5217 -0.1286 0.6813 0.059 Uiso 1 1 calc R . . H7B H -0.5452 -0.1241 0.5569 0.059 Uiso 1 1 calc R . . C8 C -0.7739(3) -0.11962(11) 0.6092(2) 0.0480(6) Uani 1 1 d . . . H8A H -0.8365 -0.0978 0.5497 0.058 Uiso 1 1 calc R . . H8B H -0.8108 -0.1066 0.6736 0.058 Uiso 1 1 calc R . . C9 C -0.8168(3) -0.18272(10) 0.5921(2) 0.0439(6) Uani 1 1 d . . . H9A H -0.7486 -0.2046 0.6496 0.053 Uiso 1 1 calc R . . H9B H -0.7851 -0.1950 0.5258 0.053 Uiso 1 1 calc R . . C10 C -1.0078(3) -0.19609(12) 0.5880(2) 0.0476(6) Uani 1 1 d . . . H10A H -1.0760 -0.1770 0.5269 0.057 Uiso 1 1 calc R . . H10B H -1.0263 -0.2370 0.5789 0.057 Uiso 1 1 calc R . . C11 C -1.0669(3) -0.17684(11) 0.6883(2) 0.0435(6) Uani 1 1 d . . . C12 C -1.0215(3) -0.19979(11) 0.8822(2) 0.0423(6) Uani 1 1 d . . . C13 C -0.9427(3) -0.23872(12) 0.9580(2) 0.0500(7) Uani 1 1 d . . . H13A H -0.8814 -0.2695 0.9378 0.060 Uiso 1 1 calc R . . C14 C -0.9553(3) -0.23166(12) 1.0622(2) 0.0510(7) Uani 1 1 d . . . H14A H -0.9009 -0.2581 1.1118 0.061 Uiso 1 1 calc R . . C15 C -1.1171(4) -0.15142(12) 1.0221(2) 0.0529(7) Uani 1 1 d . . . H15A H -1.1789 -0.1212 1.0440 0.064 Uiso 1 1 calc R . . C16 C -1.1098(4) -0.15458(12) 0.9164(2) 0.0516(7) Uani 1 1 d . . . H16A H -1.1628 -0.1271 0.8687 0.062 Uiso 1 1 calc R . . O3 O -1.2917(8) -0.0263(2) 0.9065(4) 0.203(2) Uani 1 1 d . . . N5 N -1.3050(4) 0.05163(15) 1.0191(3) 0.0904(10) Uani 1 1 d . . . C17 C -1.3811(7) 0.1054(2) 1.0331(5) 0.146(2) Uani 1 1 d . . . H17A H -1.4494 0.1176 0.9665 0.219 Uiso 1 1 calc R . . H17B H -1.2925 0.1331 1.0566 0.219 Uiso 1 1 calc R . . H17C H -1.4529 0.1019 1.0856 0.219 Uiso 1 1 calc R . . C18 C -1.1925(8) 0.0236(2) 1.1028(4) 0.143(2) Uani 1 1 d . . . H18A H -1.1533 -0.0116 1.0768 0.214 Uiso 1 1 calc R . . H18B H -1.2523 0.0156 1.1600 0.214 Uiso 1 1 calc R . . H18C H -1.0956 0.0479 1.1283 0.214 Uiso 1 1 calc R . . C19 C -1.3405(8) 0.0231(3) 0.9253(5) 0.1315(19) Uani 1 1 d . . . H19A H -1.4084 0.0422 0.8686 0.158 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 Zn 0.04396(19) 0.03619(18) 0.0483(2) -0.00297(12) 0.01226(13) -0.00170(12) Cl1 0.0467(4) 0.0463(4) 0.0869(5) -0.0001(4) 0.0261(3) 0.0023(3) Cl2 0.0928(6) 0.0437(4) 0.0569(4) 0.0014(3) -0.0007(4) 0.0116(4) O1 0.0461(12) 0.0431(11) 0.123(2) -0.0047(12) 0.0194(12) 0.0030(9) O2 0.0678(14) 0.0589(13) 0.0663(13) 0.0159(10) 0.0223(10) 0.0259(11) N1 0.0402(12) 0.0361(11) 0.0525(13) -0.0031(9) 0.0097(9) 0.0005(9) N2 0.0412(12) 0.0310(11) 0.0688(14) -0.0015(10) 0.0120(10) 0.0010(9) N3 0.0567(14) 0.0431(12) 0.0521(13) 0.0051(10) 0.0193(11) 0.0164(11) N4 0.0443(12) 0.0426(12) 0.0496(12) -0.0010(10) 0.0150(10) 0.0021(10) C1 0.0376(13) 0.0393(14) 0.0626(16) -0.0016(12) 0.0083(12) 0.0025(11) C2 0.0395(14) 0.0349(13) 0.0683(17) -0.0024(12) 0.0109(12) 0.0048(11) C3 0.0413(13) 0.0324(13) 0.0468(14) 0.0022(10) 0.0090(11) 0.0004(10) C4 0.0376(13) 0.0395(14) 0.0714(18) -0.0016(13) 0.0112(12) 0.0022(11) C5 0.0462(15) 0.0355(13) 0.0695(18) -0.0049(13) 0.0126(13) 0.0041(12) C6 0.0446(15) 0.0409(14) 0.0569(16) 0.0037(12) 0.0090(12) -0.0003(12) C7 0.0439(15) 0.0373(14) 0.0672(17) 0.0030(12) 0.0100(13) -0.0030(11) C8 0.0438(14) 0.0420(14) 0.0583(16) 0.0059(12) 0.0095(12) -0.0021(12) C9 0.0452(14) 0.0406(14) 0.0469(14) -0.0010(11) 0.0113(11) -0.0011(11) C10 0.0474(15) 0.0490(15) 0.0452(14) -0.0027(12) 0.0058(12) -0.0071(12) C11 0.0378(13) 0.0396(14) 0.0531(15) 0.0032(11) 0.0089(11) -0.0035(11) C12 0.0383(13) 0.0399(13) 0.0505(15) 0.0019(11) 0.0127(11) 0.0026(11) C13 0.0529(16) 0.0466(15) 0.0544(16) 0.0012(12) 0.0197(13) 0.0147(13) C14 0.0499(16) 0.0467(16) 0.0574(16) 0.0049(13) 0.0129(13) 0.0122(13) C15 0.0606(18) 0.0444(15) 0.0564(17) -0.0030(13) 0.0177(14) 0.0129(13) C16 0.0594(18) 0.0429(15) 0.0549(17) 0.0052(12) 0.0168(13) 0.0122(13) O3 0.307(7) 0.160(4) 0.156(4) -0.016(3) 0.076(4) 0.100(5) N5 0.087(2) 0.077(2) 0.100(3) 0.0139(19) 0.0003(19) 0.0044(18) C17 0.114(4) 0.076(3) 0.230(7) -0.017(4) -0.016(4) 0.011(3) C18 0.156(5) 0.135(5) 0.119(4) 0.014(3) -0.023(4) 0.025(4) C19 0.154(5) 0.152(5) 0.093(4) 0.019(4) 0.035(3) 0.033(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 Zn N1 2.029(2) . ? Zn N4 2.042(2) 3_457 ? Zn Cl2 2.2068(8) . ? Zn Cl1 2.2408(8) . ? O1 C6 1.211(3) . ? O2 C11 1.212(3) . ? N1 C1 1.342(3) . ? N1 C5 1.345(3) . ? N2 C6 1.366(3) . ? N2 C3 1.381(3) . ? N2 H2A 0.8600 . ? N3 C11 1.367(3) . ? N3 C12 1.391(3) . ? N3 H3A 0.8600 . ? N4 C15 1.341(3) . ? N4 C14 1.346(3) . ? N4 Zn 2.042(2) 3_457 ? C1 C2 1.373(4) . ? C1 H1A 0.9300 . ? C2 C3 1.383(4) . ? C2 H2B 0.9300 . ? C3 C4 1.397(3) . ? C4 C5 1.373(4) . ? C4 H4B 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.514(4) . ? C7 C8 1.516(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.518(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.535(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.510(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C16 1.382(4) . ? C12 C13 1.388(4) . ? C13 C14 1.361(4) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.362(4) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? O3 C19 1.255(6) . ? N5 C19 1.352(6) . ? N5 C18 1.415(5) . ? N5 C17 1.418(6) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn N4 103.80(9) . 3_457 ? N1 Zn Cl2 112.93(6) . . ? N4 Zn Cl2 107.43(6) 3_457 . ? N1 Zn Cl1 107.69(6) . . ? N4 Zn Cl1 107.05(7) 3_457 . ? Cl2 Zn Cl1 116.98(3) . . ? C1 N1 C5 116.8(2) . . ? C1 N1 Zn 123.26(17) . . ? C5 N1 Zn 119.39(17) . . ? C6 N2 C3 128.9(2) . . ? C6 N2 H2A 115.6 . . ? C3 N2 H2A 115.6 . . ? C11 N3 C12 129.1(2) . . ? C11 N3 H3A 115.4 . . ? C12 N3 H3A 115.4 . . ? C15 N4 C14 115.6(2) . . ? C15 N4 Zn 121.79(18) . 3_457 ? C14 N4 Zn 122.54(19) . 3_457 ? N1 C1 C2 122.6(2) . . ? N1 C1 H1A 118.7 . . ? C2 C1 H1A 118.7 . . ? C1 C2 C3 120.5(2) . . ? C1 C2 H2B 119.8 . . ? C3 C2 H2B 119.8 . . ? N2 C3 C2 118.6(2) . . ? N2 C3 C4 124.1(2) . . ? C2 C3 C4 117.4(2) . . ? C5 C4 C3 118.5(2) . . ? C5 C4 H4B 120.7 . . ? C3 C4 H4B 120.7 . . ? N1 C5 C4 124.2(2) . . ? N1 C5 H5A 117.9 . . ? C4 C5 H5A 117.9 . . ? O1 C6 N2 123.8(2) . . ? O1 C6 C7 123.3(2) . . ? N2 C6 C7 113.0(2) . . ? C6 C7 C8 113.8(2) . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C9 111.8(2) . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? C8 C9 C10 113.2(2) . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C9 111.7(2) . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? O2 C11 N3 122.5(3) . . ? O2 C11 C10 122.8(2) . . ? N3 C11 C10 114.7(2) . . ? C16 C12 C13 117.9(3) . . ? C16 C12 N3 124.6(2) . . ? C13 C12 N3 117.5(2) . . ? C14 C13 C12 119.7(2) . . ? C14 C13 H13A 120.1 . . ? C12 C13 H13A 120.1 . . ? N4 C14 C13 123.4(3) . . ? N4 C14 H14A 118.3 . . ? C13 C14 H14A 118.3 . . ? N4 C15 C16 125.2(3) . . ? N4 C15 H15A 117.4 . . ? C16 C15 H15A 117.4 . . ? C15 C16 C12 118.2(3) . . ? C15 C16 H16A 120.9 . . ? C12 C16 H16A 120.9 . . ? C19 N5 C18 116.0(4) . . ? C19 N5 C17 121.6(4) . . ? C18 N5 C17 122.4(5) . . ? N5 C17 H17A 109.5 . . ? N5 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N5 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N5 C18 H18A 109.5 . . ? N5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O3 C19 N5 127.0(6) . . ? O3 C19 H19A 116.5 . . ? N5 C19 H19A 116.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.517 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.057 #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 734441' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H50 Br4 N10 O6 Zn2' _chemical_formula_weight 1193.26 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' Br Br -0.2901 2.4595 '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 7.9082(6) _cell_length_b 23.8744(16) _cell_length_c 12.8431(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.3210(10) _cell_angle_gamma 90.00 _cell_volume 2392.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5724 _cell_measurement_theta_min 2.344 _cell_measurement_theta_max 23.0125 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 4.395 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2048 _exptl_absorpt_correction_T_max 0.2671 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 '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 13442 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 26.05 _reflns_number_total 4715 _reflns_number_gt 3684 _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^)+(0.0485P)^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 4715 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0881 _refine_ls_wR_factor_gt 0.0846 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 Zn Zn 0.56917(4) 0.178921(14) 0.74735(3) 0.04102(11) Uani 1 1 d . . . Br1 Br 0.86520(4) 0.159817(14) 0.75451(3) 0.05903(13) Uani 1 1 d . . . Br2 Br 0.46212(5) 0.261537(14) 0.66177(3) 0.06056(13) Uani 1 1 d . . . O1 O -0.1225(3) -0.01036(10) 0.6275(2) 0.0687(7) Uani 1 1 d . . . O2 O -0.6353(3) -0.13146(10) 0.69983(18) 0.0617(6) Uani 1 1 d . . . O3 O 0.2384(10) -0.0181(4) 0.9095(5) 0.243(4) Uani 1 1 d . . . N1 N 0.4376(3) 0.11001(10) 0.69012(19) 0.0414(6) Uani 1 1 d . . . N2 N 0.1530(3) -0.03735(10) 0.6291(2) 0.0448(6) Uani 1 1 d . . . H2NA H 0.2141 -0.0663 0.6209 0.054 Uiso 1 1 calc R . . N3 N -0.4820(3) -0.20219(11) 0.7828(2) 0.0480(6) Uani 1 1 d . . . H3NA H -0.4209 -0.2307 0.7717 0.058 Uiso 1 1 calc R . . N4 N -0.5273(3) -0.18384(10) 1.09980(19) 0.0431(6) Uani 1 1 d . . . N5 N 0.1895(5) 0.05020(17) 1.0282(4) 0.0928(12) Uani 1 1 d . . . C1 C 0.5105(4) 0.06055(13) 0.6722(2) 0.0461(7) Uani 1 1 d . . . H1A H 0.6288 0.0590 0.6761 0.055 Uiso 1 1 calc R . . C2 C 0.4177(4) 0.01264(12) 0.6486(3) 0.0480(8) Uani 1 1 d . . . H2A H 0.4730 -0.0202 0.6345 0.058 Uiso 1 1 calc R . . C3 C 0.2419(4) 0.01273(12) 0.6454(2) 0.0400(7) Uani 1 1 d . . . C4 C 0.1644(4) 0.06374(13) 0.6597(3) 0.0466(7) Uani 1 1 d . . . H4A H 0.0460 0.0665 0.6542 0.056 Uiso 1 1 calc R . . C5 C 0.2670(4) 0.11001(13) 0.6821(3) 0.0478(8) Uani 1 1 d . . . H5A H 0.2138 0.1438 0.6924 0.057 Uiso 1 1 calc R . . C6 C -0.0184(4) -0.04696(13) 0.6241(2) 0.0456(7) Uani 1 1 d . . . C7 C -0.0659(4) -0.10857(13) 0.6134(3) 0.0478(7) Uani 1 1 d . . . H7A H -0.0312 -0.1232 0.5496 0.057 Uiso 1 1 calc R . . H7B H -0.0030 -0.1289 0.6728 0.057 Uiso 1 1 calc R . . C8 C -0.2553(4) -0.11900(12) 0.6092(2) 0.0440(7) Uani 1 1 d . . . H8A H -0.3187 -0.0976 0.5514 0.053 Uiso 1 1 calc R . . H8B H -0.2893 -0.1059 0.6742 0.053 Uiso 1 1 calc R . . C9 C -0.3010(4) -0.18031(12) 0.5942(2) 0.0424(7) Uani 1 1 d . . . H9A H -0.2324 -0.2018 0.6498 0.051 Uiso 1 1 calc R . . H9B H -0.2722 -0.1928 0.5274 0.051 Uiso 1 1 calc R . . C10 C -0.4906(4) -0.19222(13) 0.5957(2) 0.0452(7) Uani 1 1 d . . . H10A H -0.5591 -0.1739 0.5358 0.054 Uiso 1 1 calc R . . H10B H -0.5108 -0.2322 0.5886 0.054 Uiso 1 1 calc R . . C11 C -0.5464(4) -0.17212(12) 0.6953(2) 0.0416(7) Uani 1 1 d . . . C12 C -0.5001(4) -0.19373(12) 0.8877(2) 0.0419(7) Uani 1 1 d . . . C13 C -0.5894(4) -0.14964(13) 0.9221(3) 0.0504(8) Uani 1 1 d . . . H13A H -0.6408 -0.1226 0.8754 0.060 Uiso 1 1 calc R . . C14 C -0.5998(4) -0.14702(13) 1.0279(3) 0.0529(8) Uani 1 1 d . . . H14A H -0.6616 -0.1176 1.0508 0.063 Uiso 1 1 calc R . . C15 C -0.4397(4) -0.22577(14) 1.0647(2) 0.0503(8) Uani 1 1 d . . . H15A H -0.3880 -0.2521 1.1129 0.060 Uiso 1 1 calc R . . C16 C -0.4230(4) -0.23153(14) 0.9620(3) 0.0523(8) Uani 1 1 d . . . H16A H -0.3593 -0.2611 0.9414 0.063 Uiso 1 1 calc R . . C17 C 0.0994(8) 0.0998(3) 1.0464(6) 0.154(3) Uani 1 1 d . . . H17A H 0.0436 0.1147 0.9803 0.230 Uiso 1 1 calc R . . H17B H 0.1786 0.1270 1.0812 0.230 Uiso 1 1 calc R . . H17C H 0.0152 0.0913 1.0902 0.230 Uiso 1 1 calc R . . C18 C 0.2887(9) 0.0170(3) 1.1073(5) 0.162(3) Uani 1 1 d . . . H18A H 0.3348 -0.0146 1.0750 0.244 Uiso 1 1 calc R . . H18B H 0.2175 0.0040 1.1562 0.244 Uiso 1 1 calc R . . H18C H 0.3809 0.0390 1.1442 0.244 Uiso 1 1 calc R . . C19 C 0.1812(11) 0.0306(4) 0.9313(6) 0.172(4) Uani 1 1 d . . . H19A H 0.1312 0.0530 0.8756 0.206 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 Zn 0.0430(2) 0.0373(2) 0.0443(2) -0.00369(15) 0.01192(15) -0.00078(14) Br1 0.0454(2) 0.0466(2) 0.0898(3) 0.00108(17) 0.02507(17) 0.00321(14) Br2 0.0816(3) 0.0450(2) 0.0514(2) -0.00048(15) -0.00029(17) 0.01043(17) O1 0.0435(13) 0.0423(13) 0.120(2) -0.0018(14) 0.0124(13) 0.0037(11) O2 0.0724(16) 0.0571(15) 0.0580(15) 0.0133(12) 0.0174(12) 0.0276(12) O3 0.300(9) 0.260(8) 0.184(6) -0.024(5) 0.081(5) 0.119(7) N1 0.0409(14) 0.0372(14) 0.0466(15) -0.0025(11) 0.0087(11) 0.0014(10) N2 0.0389(14) 0.0313(13) 0.0637(17) 0.0011(12) 0.0070(12) 0.0037(10) N3 0.0580(16) 0.0455(15) 0.0434(15) 0.0034(12) 0.0165(12) 0.0170(12) N4 0.0458(15) 0.0417(14) 0.0441(15) 0.0003(12) 0.0140(11) 0.0045(11) N5 0.094(3) 0.084(3) 0.092(3) 0.008(2) -0.008(2) 0.008(2) C1 0.0376(16) 0.0413(17) 0.059(2) -0.0025(15) 0.0060(14) 0.0057(13) C2 0.0425(17) 0.0314(16) 0.071(2) -0.0041(15) 0.0113(15) 0.0060(13) C3 0.0413(16) 0.0361(16) 0.0425(17) 0.0028(13) 0.0066(12) 0.0004(12) C4 0.0390(17) 0.0390(17) 0.063(2) -0.0004(15) 0.0104(14) 0.0019(13) C5 0.0454(18) 0.0374(17) 0.062(2) -0.0055(15) 0.0125(15) 0.0057(13) C6 0.0441(18) 0.0392(17) 0.0521(19) 0.0048(14) 0.0030(14) -0.0014(14) C7 0.0454(18) 0.0388(17) 0.058(2) 0.0035(15) 0.0052(14) -0.0005(13) C8 0.0435(17) 0.0422(17) 0.0462(18) 0.0019(13) 0.0070(13) -0.0017(13) C9 0.0455(18) 0.0422(17) 0.0402(17) -0.0023(13) 0.0089(13) -0.0032(13) C10 0.0464(18) 0.0471(18) 0.0412(17) -0.0001(14) 0.0048(13) -0.0055(14) C11 0.0395(17) 0.0387(17) 0.0459(18) 0.0031(13) 0.0051(13) -0.0031(13) C12 0.0421(17) 0.0398(16) 0.0461(18) 0.0008(13) 0.0140(13) 0.0032(13) C13 0.061(2) 0.0423(18) 0.050(2) 0.0027(14) 0.0144(15) 0.0119(15) C14 0.065(2) 0.0413(18) 0.056(2) -0.0048(15) 0.0183(16) 0.0126(15) C15 0.056(2) 0.0503(19) 0.0464(19) 0.0069(15) 0.0127(15) 0.0136(15) C16 0.062(2) 0.049(2) 0.0487(19) 0.0042(15) 0.0183(16) 0.0228(16) C17 0.128(5) 0.097(5) 0.221(8) -0.025(5) -0.017(5) 0.026(4) C18 0.185(8) 0.178(7) 0.107(5) 0.030(5) -0.026(5) 0.002(6) C19 0.184(8) 0.236(10) 0.099(5) 0.002(6) 0.035(5) 0.079(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 Zn N1 2.021(2) . ? Zn N4 2.046(2) 3_557 ? Zn Br2 2.3481(5) . ? Zn Br1 2.3722(5) . ? O1 C6 1.207(4) . ? O2 C11 1.205(4) . ? O3 C19 1.294(9) . ? N1 C5 1.336(4) . ? N1 C1 1.350(4) . ? N2 C6 1.366(4) . ? N2 C3 1.386(4) . ? N2 H2NA 0.8600 . ? N3 C11 1.362(4) . ? N3 C12 1.391(4) . ? N3 H3NA 0.8600 . ? N4 C14 1.336(4) . ? N4 C15 1.336(4) . ? N4 Zn 2.046(2) 3_557 ? N5 C19 1.321(8) . ? N5 C17 1.421(7) . ? N5 C18 1.421(6) . ? C1 C2 1.366(4) . ? C1 H1A 0.9300 . ? C2 C3 1.384(4) . ? C2 H2A 0.9300 . ? C3 C4 1.389(4) . ? C4 C5 1.373(4) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.519(4) . ? C7 C8 1.511(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.512(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.530(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.498(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C13 1.380(4) . ? C12 C16 1.382(4) . ? C13 C14 1.375(5) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.354(4) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn N4 104.00(10) . 3_557 ? N1 Zn Br2 112.85(7) . . ? N4 Zn Br2 107.38(7) 3_557 . ? N1 Zn Br1 107.73(7) . . ? N4 Zn Br1 106.61(7) 3_557 . ? Br2 Zn Br1 117.282(19) . . ? C5 N1 C1 116.1(3) . . ? C5 N1 Zn 118.84(19) . . ? C1 N1 Zn 124.4(2) . . ? C6 N2 C3 128.8(2) . . ? C6 N2 H2NA 115.6 . . ? C3 N2 H2NA 115.6 . . ? C11 N3 C12 129.7(3) . . ? C11 N3 H3NA 115.1 . . ? C12 N3 H3NA 115.1 . . ? C14 N4 C15 116.6(3) . . ? C14 N4 Zn 120.5(2) . 3_557 ? C15 N4 Zn 122.7(2) . 3_557 ? C19 N5 C17 120.1(6) . . ? C19 N5 C18 114.4(6) . . ? C17 N5 C18 125.5(6) . . ? N1 C1 C2 122.8(3) . . ? N1 C1 H1A 118.6 . . ? C2 C1 H1A 118.6 . . ? C1 C2 C3 120.4(3) . . ? C1 C2 H2A 119.8 . . ? C3 C2 H2A 119.8 . . ? C2 C3 N2 119.1(3) . . ? C2 C3 C4 117.4(3) . . ? N2 C3 C4 123.5(3) . . ? C5 C4 C3 118.3(3) . . ? C5 C4 H4A 120.8 . . ? C3 C4 H4A 120.8 . . ? N1 C5 C4 124.8(3) . . ? N1 C5 H5A 117.6 . . ? C4 C5 H5A 117.6 . . ? O1 C6 N2 123.7(3) . . ? O1 C6 C7 123.0(3) . . ? N2 C6 C7 113.3(3) . . ? C8 C7 C6 113.1(3) . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 C9 112.3(2) . . ? C7 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? C7 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? C8 C9 C10 113.1(3) . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 112.1(2) . . ? C11 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? C11 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? O2 C11 N3 121.8(3) . . ? O2 C11 C10 123.7(3) . . ? N3 C11 C10 114.4(3) . . ? C13 C12 C16 117.9(3) . . ? C13 C12 N3 124.0(3) . . ? C16 C12 N3 118.1(3) . . ? C14 C13 C12 117.9(3) . . ? C14 C13 H13A 121.1 . . ? C12 C13 H13A 121.1 . . ? N4 C14 C13 124.4(3) . . ? N4 C14 H14A 117.8 . . ? C13 C14 H14A 117.8 . . ? N4 C15 C16 122.9(3) . . ? N4 C15 H15A 118.6 . . ? C16 C15 H15A 118.6 . . ? C15 C16 C12 120.3(3) . . ? C15 C16 H16A 119.8 . . ? C12 C16 H16A 119.8 . . ? N5 C17 H17A 109.5 . . ? N5 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N5 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N5 C18 H18A 109.5 . . ? N5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O3 C19 N5 123.8(8) . . ? O3 C19 H19A 118.1 . . ? N5 C19 H19A 118.1 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.524 _refine_diff_density_min -0.407 _refine_diff_density_rms 0.065