Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Parthasarathi Dastidar' _publ_contact_author_address ; Analytical Science Discipline Central Salt & Marine Chemicals Research Institute G B Marg Bhavnagar Gujarat 364002 INDIA ; _publ_contact_author_email PARTHOD123@REDIFFMAIL.COM _publ_section_title ; Hydrogen-bonded microporous network, helix and 1D zigzag chains in MOFs of Zn(II): studying the effects of ligating topologies, hydrogen bonding backbone and counter-anions ; loop_ _publ_author_name 'Parthasarathi Dastidar' 'Amitava Das' 'D. Krishna Kumar' # Attachment '1a_kkb482i_FINAL_rev_1.cif' data_kkb482i _database_code_depnum_ccdc_archive 'CCDC 603374' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H20 Cl2 N4 O3 Zn' _chemical_formula_weight 416.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 19.1929(13) _cell_length_b 7.1978(5) _cell_length_c 24.4277(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3374.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 1.790 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5202 _exptl_absorpt_correction_T_max 0.8701 _exptl_absorpt_process_details BRUKER-SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18871 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 28.23 _reflns_number_total 4036 _reflns_number_gt 3302 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0509P)^2^+5.0479P] 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 4036 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.1090 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.110954(17) 1.08231(5) 0.113250(13) 0.02123(12) Uani 1 1 d . . . Cl1 Cl 0.00155(4) 1.01305(17) 0.08740(3) 0.0439(3) Uani 1 1 d . . . Cl2 Cl 0.12343(4) 1.37593(12) 0.14162(3) 0.02676(19) Uani 1 1 d . . . N1 N 0.13319(13) 0.9271(4) 0.18021(10) 0.0239(6) Uani 1 1 d . . . C2 C 0.08718(16) 0.8021(5) 0.19924(13) 0.0257(7) Uani 1 1 d . . . H2 H 0.0487 0.7734 0.1777 0.031 Uiso 1 1 calc R . . C3 C 0.09395(16) 0.7150(5) 0.24853(13) 0.0279(7) Uani 1 1 d . . . H3 H 0.0603 0.6305 0.2599 0.033 Uiso 1 1 calc R . . C4 C 0.15120(15) 0.7522(5) 0.28193(12) 0.0238(7) Uani 1 1 d . . . C5 C 0.20071(17) 0.8770(5) 0.26208(13) 0.0309(8) Uani 1 1 d . . . H5 H 0.2406 0.9037 0.2822 0.037 Uiso 1 1 calc R . . C6 C 0.18936(17) 0.9597(6) 0.21218(13) 0.0317(8) Uani 1 1 d . . . H6 H 0.2225 1.0436 0.1996 0.038 Uiso 1 1 calc R . . N7 N 0.15362(13) 0.6665(4) 0.33290(11) 0.0284(6) Uani 1 1 d . . . H7 H 0.1176 0.6038 0.3427 0.034 Uiso 1 1 calc R . . C8 C 0.20877(15) 0.6729(5) 0.36927(12) 0.0213(6) Uani 1 1 d . . . O9 O 0.26508(11) 0.7386(3) 0.35818(8) 0.0244(5) Uani 1 1 d . . . N10 N 0.19187(13) 0.5966(4) 0.41927(11) 0.0256(6) Uani 1 1 d . . . H10 H 0.1489 0.5691 0.4249 0.031 Uiso 1 1 calc R . . C11 C 0.23874(15) 0.5607(4) 0.46129(12) 0.0203(6) Uani 1 1 d . . . C12 C 0.21182(15) 0.5124(5) 0.51265(12) 0.0221(6) Uani 1 1 d . . . H12 H 0.1639 0.5066 0.5179 0.026 Uiso 1 1 calc R . . C13 C 0.25602(15) 0.4741(4) 0.55496(11) 0.0187(6) Uani 1 1 d . . . H13 H 0.2370 0.4421 0.5887 0.022 Uiso 1 1 calc R . . N14 N 0.32600(12) 0.4804(3) 0.55022(10) 0.0168(5) Uani 1 1 d . . . C15 C 0.35206(15) 0.5263(4) 0.50081(12) 0.0190(6) Uani 1 1 d . . . H15 H 0.4002 0.5307 0.4969 0.023 Uiso 1 1 calc R . . C16 C 0.31145(15) 0.5672(4) 0.45568(12) 0.0202(6) Uani 1 1 d . . . H16 H 0.3318 0.5982 0.4224 0.024 Uiso 1 1 calc R . . C17 C 0.0751(3) 0.2458(8) 0.3001(2) 0.0544(13) Uani 1 1 d . . . O18 O 0.04545(16) 0.3977(5) 0.32842(15) 0.0556(9) Uani 1 1 d . . . C19A C -0.0061(3) 0.4203(10) 0.5285(3) 0.0261(14) Uiso 0.50 1 d P . . C19B C 0.0164(3) 0.4596(10) 0.4701(3) 0.0255(14) Uiso 0.50 1 d P . . O20A O 0.0577(2) 0.6231(6) 0.46642(18) 0.0236(9) Uiso 0.50 1 d P . . O20B O -0.0560(2) 0.5567(6) 0.54732(18) 0.0259(10) Uiso 0.50 1 d P . . H17A H 0.042(4) 0.162(9) 0.285(3) 0.11(2) Uiso 1 1 d . . . H17B H 0.106(3) 0.174(9) 0.326(3) 0.10(2) Uiso 1 1 d . . . H17C H 0.107(3) 0.259(9) 0.275(3) 0.10(2) Uiso 1 1 d . . . H18 H 0.009(3) 0.378(8) 0.341(2) 0.070(18) 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 Zn1 0.01616(18) 0.0352(2) 0.01230(18) 0.00308(14) -0.00008(12) -0.00315(14) Cl1 0.0206(4) 0.0921(8) 0.0190(4) 0.0055(4) -0.0050(3) -0.0193(4) Cl2 0.0265(4) 0.0335(4) 0.0202(4) -0.0024(3) 0.0029(3) 0.0006(3) N1 0.0205(12) 0.0349(16) 0.0163(12) 0.0049(11) -0.0031(10) -0.0057(11) C2 0.0199(15) 0.0325(18) 0.0248(16) 0.0052(13) -0.0061(12) -0.0066(13) C3 0.0180(15) 0.0369(19) 0.0287(17) 0.0108(14) -0.0032(12) -0.0080(13) C4 0.0175(14) 0.0368(19) 0.0169(14) 0.0053(13) 0.0016(11) 0.0009(13) C5 0.0230(15) 0.051(2) 0.0190(16) 0.0098(15) -0.0077(12) -0.0120(15) C6 0.0224(16) 0.052(2) 0.0208(16) 0.0123(15) -0.0023(12) -0.0160(15) N7 0.0165(12) 0.0469(18) 0.0217(13) 0.0130(13) 0.0018(10) -0.0035(12) C8 0.0192(14) 0.0288(17) 0.0158(14) 0.0038(12) 0.0008(11) 0.0046(12) O9 0.0214(11) 0.0349(13) 0.0169(10) 0.0044(9) -0.0019(8) -0.0035(9) N10 0.0145(12) 0.0423(17) 0.0198(13) 0.0090(12) 0.0055(10) 0.0066(11) C11 0.0216(14) 0.0243(17) 0.0150(13) 0.0011(11) 0.0017(11) 0.0076(12) C12 0.0185(14) 0.0268(17) 0.0209(15) 0.0023(12) 0.0033(11) 0.0043(12) C13 0.0209(14) 0.0204(15) 0.0150(13) 0.0008(11) 0.0030(11) 0.0040(12) N14 0.0185(11) 0.0177(12) 0.0141(11) -0.0016(9) 0.0011(9) 0.0008(10) C15 0.0174(13) 0.0214(15) 0.0181(14) -0.0027(11) 0.0023(11) 0.0002(11) C16 0.0205(14) 0.0251(17) 0.0151(14) 0.0003(12) 0.0048(11) 0.0044(12) C17 0.040(2) 0.078(4) 0.046(3) 0.022(3) -0.010(2) -0.020(3) O18 0.0312(15) 0.061(2) 0.075(2) 0.0295(18) 0.0075(15) -0.0159(15) _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 N14 2.010(2) 2_564 ? Zn1 N1 2.026(3) . ? Zn1 Cl2 2.2370(9) . ? Zn1 Cl1 2.2486(8) . ? N1 C2 1.344(4) . ? N1 C6 1.352(4) . ? C2 C3 1.363(4) . ? C2 H2 0.9300 . ? C3 C4 1.395(4) . ? C3 H3 0.9300 . ? C4 N7 1.390(4) . ? C4 C5 1.395(4) . ? C5 C6 1.374(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? N7 C8 1.383(4) . ? N7 H7 0.8600 . ? C8 O9 1.210(4) . ? C8 N10 1.378(4) . ? N10 C11 1.389(4) . ? N10 H10 0.8600 . ? C11 C12 1.401(4) . ? C11 C16 1.403(4) . ? C12 C13 1.365(4) . ? C12 H12 0.9300 . ? C13 N14 1.349(4) . ? C13 H13 0.9300 . ? N14 C15 1.348(4) . ? N14 Zn1 2.010(2) 2_565 ? C15 C16 1.382(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 O18 1.413(7) 1 ? C17 O18 1.413(7) . ? C17 H17A 0.95(7) . ? C17 H17B 1.00(7) . ? C17 H17C 0.87(7) . ? O18 H18 0.77(5) . ? C19A C19B 0.887(8) 5_566 ? C19A O20A 1.046(7) 5_566 ? C19A O20B 1.446(8) . ? C19A C19B 1.517(9) . ? C19A C19A 1.818(14) 5_566 ? C19B O20B 0.879(7) 5_566 ? C19B C19A 0.887(8) 5_566 ? C19B O20A 1.422(8) . ? C19B O20A 1.422(8) 1 ? C19B C19B 1.696(13) 5_566 ? O20A C19A 1.046(7) 5_566 ? O20A O20B 1.337(6) 5_566 ? O20B C19B 0.879(7) 5_566 ? O20B O20A 1.337(6) 5_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 N14 Zn1 N1 111.59(10) 2_564 . ? N14 Zn1 Cl2 112.64(8) 2_564 . ? N1 Zn1 Cl2 104.37(8) . . ? N14 Zn1 Cl1 107.30(7) 2_564 . ? N1 Zn1 Cl1 107.53(8) . . ? Cl2 Zn1 Cl1 113.35(4) . . ? C2 N1 C6 116.1(3) . . ? C2 N1 Zn1 120.7(2) . . ? C6 N1 Zn1 122.6(2) . . ? N1 C2 C3 123.4(3) . . ? N1 C2 H2 118.3 . . ? C3 C2 H2 118.3 . . ? C2 C3 C4 120.2(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? N7 C4 C5 125.1(3) . . ? N7 C4 C3 117.7(3) . . ? C5 C4 C3 117.2(3) . . ? C6 C5 C4 118.7(3) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? N1 C6 C5 124.3(3) . . ? N1 C6 H6 117.8 . . ? C5 C6 H6 117.8 . . ? C8 N7 C4 125.9(3) . . ? C8 N7 H7 117.1 . . ? C4 N7 H7 117.1 . . ? O9 C8 N10 124.3(3) . . ? O9 C8 N7 123.6(3) . . ? N10 C8 N7 112.1(3) . . ? C8 N10 C11 125.2(3) . . ? C8 N10 H10 117.4 . . ? C11 N10 H10 117.4 . . ? N10 C11 C12 118.0(3) . . ? N10 C11 C16 124.4(3) . . ? C12 C11 C16 117.6(3) . . ? C13 C12 C11 119.9(3) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? N14 C13 C12 123.1(3) . . ? N14 C13 H13 118.4 . . ? C12 C13 H13 118.4 . . ? C15 N14 C13 117.0(2) . . ? C15 N14 Zn1 121.19(19) . 2_565 ? C13 N14 Zn1 121.75(19) . 2_565 ? N14 C15 C16 123.9(3) . . ? N14 C15 H15 118.1 . . ? C16 C15 H15 118.1 . . ? C15 C16 C11 118.4(3) . . ? C15 C16 H16 120.8 . . ? C11 C16 H16 120.8 . . ? O18 C17 H17A 115(4) 1 . ? O18 C17 H17A 115(4) . . ? O18 C17 H17B 109(4) 1 . ? O18 C17 H17B 109(4) . . ? H17A C17 H17B 108(5) . . ? O18 C17 H17C 123(4) 1 . ? O18 C17 H17C 123(4) . . ? H17A C17 H17C 106(5) . . ? H17B C17 H17C 94(5) . . ? C17 O18 H18 114(4) . . ? C19B C19A O20A 94.3(8) 5_566 5_566 ? C19B C19A O20B 34.8(5) 5_566 . ? O20A C19A O20B 62.5(4) 5_566 . ? C19B C19A C19B 85.4(8) 5_566 . ? O20A C19A C19B 115.9(6) 5_566 . ? O20B C19A C19B 111.2(6) . . ? C19B C19A C19A 56.3(6) 5_566 5_566 ? O20A C19A C19A 113.7(7) 5_566 5_566 ? O20B C19A C19A 84.3(5) . 5_566 ? C19B C19A C19A 29.1(3) . 5_566 ? O20B C19B C19A 110.0(9) 5_566 5_566 ? O20B C19B O20A 66.2(6) 5_566 . ? C19A C19B O20A 47.2(6) 5_566 . ? O20B C19B O20A 66.2(6) 5_566 1 ? C19A C19B O20A 47.2(6) 5_566 1 ? O20B C19B C19A 132.5(8) 5_566 . ? C19A C19B C19A 94.6(8) 5_566 . ? O20A C19B C19A 111.8(6) . . ? O20A C19B C19A 111.8(6) 1 . ? O20B C19B C19B 141.6(9) 5_566 5_566 ? C19A C19B C19B 63.1(7) 5_566 5_566 ? O20A C19B C19B 88.7(6) . 5_566 ? O20A C19B C19B 88.7(6) 1 5_566 ? C19A C19B C19B 31.4(3) . 5_566 ? C19A O20A O20B 73.6(5) 5_566 5_566 ? C19A O20A C19B 38.5(4) 5_566 . ? O20B O20A C19B 37.0(3) 5_566 . ? C19B O20B O20A 76.8(6) 5_566 5_566 ? C19B O20B C19A 35.2(5) 5_566 . ? O20A O20B C19A 43.9(3) 5_566 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7 O18 0.86 2.06 2.840(4) 150.7 1 N10 H10 O20A 0.86 2.06 2.827(5) 148.3 1 N10 H10 O20B 0.86 2.11 2.947(5) 163.9 5_566 O18 H18 Cl2 0.77(5) 2.58(5) 3.327(3) 163(5) 3_545 C3 H3 O18 0.93 2.39 3.145(4) 138.8 1 C12 H12 O20A 0.93 2.54 3.265(5) 135.3 1 _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 28.23 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.727 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.099 # Attachment '1b_kkb482h_FINAL_rev_1.cif' data_kkb482h _database_code_depnum_ccdc_archive 'CCDC 603375' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 Cl2 N4 O2.98 Zn' _chemical_formula_weight 384.2 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 Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 18.3464(17) _cell_length_b 6.8405(6) _cell_length_c 24.146(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3030.3(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.675 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1535 _exptl_absorpt_coefficient_mu 1.986 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5690 _exptl_absorpt_correction_T_max 0.8901 _exptl_absorpt_process_details BRUKER-SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16793 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3613 _reflns_number_gt 2979 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0474P)^2^+1.7686P] 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 3613 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1013 _refine_ls_wR_factor_gt 0.0962 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.099591(18) 0.41458(5) 0.379112(13) 0.01453(11) Uani 1 1 d . . . Cl2 Cl -0.01379(4) 0.45719(11) 0.34619(3) 0.02131(17) Uani 1 1 d . . . Cl3 Cl 0.12365(4) 0.11514(11) 0.41220(3) 0.02328(18) Uani 1 1 d . . . N1 N 0.16814(13) 0.4688(3) 0.31502(10) 0.0152(5) Uani 1 1 d . . . C2 C 0.14205(16) 0.5080(4) 0.26431(12) 0.0178(6) Uani 1 1 d . . . H2 H 0.0918 0.5183 0.2602 0.021 Uiso 1 1 calc R . . C3 C 0.18479(16) 0.5340(4) 0.21804(12) 0.0167(6) Uani 1 1 d . . . H3 H 0.1638 0.5585 0.1837 0.020 Uiso 1 1 calc R . . C4 C 0.26050(15) 0.5225(4) 0.22400(11) 0.0142(6) Uani 1 1 d . . . C5 C 0.28810(15) 0.4823(4) 0.27678(12) 0.0162(6) Uani 1 1 d . . . H5 H 0.3381 0.4741 0.2824 0.019 Uiso 1 1 calc R . . C6 C 0.24077(16) 0.4550(4) 0.32025(12) 0.0154(6) Uani 1 1 d . . . H6 H 0.2600 0.4256 0.3549 0.018 Uiso 1 1 calc R . . N7 N 0.30946(14) 0.5478(4) 0.18120(10) 0.0183(5) Uani 1 1 d . . . C8 C 0.29396(16) 0.6142(4) 0.12828(12) 0.0168(6) Uani 1 1 d . . . O9 O 0.23342(11) 0.6608(3) 0.11323(8) 0.0212(5) Uani 1 1 d . . . N10 N 0.35519(15) 0.6224(4) 0.09594(11) 0.0188(6) Uani 1 1 d . . . C11 C 0.36131(16) 0.7121(4) 0.04470(12) 0.0162(6) Uani 1 1 d . . . C12 C 0.30359(16) 0.7918(5) 0.01549(12) 0.0210(7) Uani 1 1 d . . . H12 H 0.2563 0.7823 0.0290 0.025 Uiso 1 1 calc R . . C13 C 0.31736(17) 0.8853(5) -0.03379(13) 0.0220(7) Uani 1 1 d . . . H13 H 0.2781 0.9392 -0.0528 0.026 Uiso 1 1 calc R . . N14 N 0.38376(13) 0.9035(3) -0.05616(10) 0.0172(5) Uani 1 1 d . . . C15 C 0.43955(15) 0.8209(4) -0.02849(12) 0.0167(6) Uani 1 1 d . . . H15 H 0.4861 0.8288 -0.0436 0.020 Uiso 1 1 calc R . . C16 C 0.43077(16) 0.7256(4) 0.02099(11) 0.0173(6) Uani 1 1 d . . . H16 H 0.4707 0.6702 0.0387 0.021 Uiso 1 1 calc R . . O17 O 0.4615(3) 0.5894(7) 0.2463(2) 0.0458(13) Uiso 0.55 1 d P . . O18 O 0.1059(5) 0.7384(15) 0.0435(4) 0.044(2) Uiso 0.27 1 d P . . O19 O 0.4543(3) 0.4182(7) 0.1697(2) 0.0399(12) Uiso 0.57 1 d P . . O20 O 0.4859(3) 0.4265(7) 0.1459(2) 0.0452(12) Uiso 0.59 1 d P . . H7 H 0.3532(19) 0.529(5) 0.1901(15) 0.026(10) Uiso 1 1 d . . . H10 H 0.388(2) 0.578(6) 0.1077(18) 0.036(13) 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 Zn1 0.01593(18) 0.0183(2) 0.00937(18) 0.00034(13) -0.00049(12) -0.00052(12) Cl2 0.0170(3) 0.0287(4) 0.0182(4) 0.0027(3) -0.0037(3) 0.0000(3) Cl3 0.0245(4) 0.0216(4) 0.0237(4) 0.0074(3) 0.0061(3) 0.0051(3) N1 0.0196(12) 0.0160(12) 0.0101(12) -0.0009(9) -0.0001(9) -0.0029(10) C2 0.0165(14) 0.0230(16) 0.0140(14) -0.0017(12) -0.0019(12) -0.0047(12) C3 0.0208(14) 0.0190(15) 0.0103(13) 0.0012(11) -0.0017(12) -0.0026(12) C4 0.0188(14) 0.0131(14) 0.0107(13) -0.0007(11) 0.0016(11) -0.0008(11) C5 0.0151(14) 0.0160(14) 0.0177(15) 0.0007(11) -0.0010(11) -0.0019(11) C6 0.0221(15) 0.0139(14) 0.0102(13) 0.0014(10) -0.0040(11) -0.0016(11) N7 0.0149(13) 0.0246(14) 0.0154(13) 0.0030(10) 0.0021(10) 0.0013(10) C8 0.0198(15) 0.0166(15) 0.0139(14) 0.0032(11) 0.0008(12) -0.0022(11) O9 0.0193(11) 0.0322(13) 0.0121(10) 0.0059(9) 0.0029(8) 0.0008(9) N10 0.0155(13) 0.0252(14) 0.0156(13) 0.0050(11) 0.0002(11) 0.0024(11) C11 0.0219(15) 0.0149(14) 0.0118(14) -0.0007(11) 0.0005(11) -0.0032(11) C12 0.0165(15) 0.0310(18) 0.0156(15) 0.0036(13) 0.0038(12) 0.0007(12) C13 0.0207(15) 0.0289(17) 0.0163(15) 0.0034(13) -0.0012(13) 0.0031(13) N14 0.0200(13) 0.0204(13) 0.0111(12) -0.0001(10) 0.0005(10) -0.0009(10) C15 0.0138(14) 0.0214(15) 0.0148(14) -0.0021(12) 0.0004(11) -0.0018(11) C16 0.0183(14) 0.0204(15) 0.0131(14) -0.0014(11) -0.0029(12) -0.0014(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N14 2.021(2) 2_565 ? Zn1 N1 2.028(2) . ? Zn1 Cl3 2.2424(8) . ? Zn1 Cl2 2.2458(8) . ? N1 C2 1.342(4) . ? N1 C6 1.342(4) . ? C2 C3 1.376(4) . ? C2 H2 0.9300 . ? C3 C4 1.399(4) . ? C3 H3 0.9300 . ? C4 N7 1.380(4) . ? C4 C5 1.399(4) . ? C5 C6 1.375(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? N7 C8 1.386(4) . ? N7 H7 0.84(3) . ? C8 O9 1.211(4) . ? C8 N10 1.369(4) . ? N10 C11 1.385(4) . ? N10 H10 0.73(4) . ? C11 C12 1.384(4) . ? C11 C16 1.400(4) . ? C12 C13 1.374(4) . ? C12 H12 0.9300 . ? C13 N14 1.338(4) . ? C13 H13 0.9300 . ? N14 C15 1.347(4) . ? N14 Zn1 2.021(2) 2_564 ? C15 C16 1.370(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? O17 O17 1.422(10) 3_655 ? O19 O20 0.819(6) 1 ? O19 O20 0.819(6) . ? O20 O19 0.819(6) 1 ? 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 N14 Zn1 N1 112.56(10) 2_565 . ? N14 Zn1 Cl3 104.91(7) 2_565 . ? N1 Zn1 Cl3 108.48(7) . . ? N14 Zn1 Cl2 109.50(7) 2_565 . ? N1 Zn1 Cl2 106.28(7) . . ? Cl3 Zn1 Cl2 115.27(3) . . ? C2 N1 C6 117.0(2) . . ? C2 N1 Zn1 120.78(19) . . ? C6 N1 Zn1 122.07(19) . . ? N1 C2 C3 124.3(3) . . ? N1 C2 H2 117.9 . . ? C3 C2 H2 117.9 . . ? C2 C3 C4 118.4(3) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? N7 C4 C3 124.2(3) . . ? N7 C4 C5 118.1(3) . . ? C3 C4 C5 117.7(3) . . ? C6 C5 C4 119.6(3) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? N1 C6 C5 123.1(3) . . ? N1 C6 H6 118.5 . . ? C5 C6 H6 118.5 . . ? C4 N7 C8 126.7(3) . . ? C4 N7 H7 114(2) . . ? C8 N7 H7 119(2) . . ? O9 C8 N10 124.8(3) . . ? O9 C8 N7 123.4(3) . . ? N10 C8 N7 111.8(3) . . ? C8 N10 C11 126.4(3) . . ? C8 N10 H10 116(3) . . ? C11 N10 H10 118(3) . . ? C12 C11 N10 124.6(3) . . ? C12 C11 C16 117.5(3) . . ? N10 C11 C16 117.9(3) . . ? C13 C12 C11 118.9(3) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? N14 C13 C12 124.1(3) . . ? N14 C13 H13 118.0 . . ? C12 C13 H13 118.0 . . ? C13 N14 C15 116.9(3) . . ? C13 N14 Zn1 120.5(2) . 2_564 ? C15 N14 Zn1 121.8(2) . 2_564 ? N14 C15 C16 122.9(3) . . ? N14 C15 H15 118.6 . . ? C16 C15 H15 118.6 . . ? C15 C16 C11 119.7(3) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? 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 N7 H7 O17 0.84(3) 2.44(4) 3.216(6) 153(3) 1 N7 H7 O19 0.84(3) 2.06(4) 2.815(6) 149(3) 1 N10 H10 O19 0.73(4) 2.22(4) 2.904(6) 157(4) 1 N10 H10 O20 0.73(4) 2.28(4) 3.001(6) 177(4) 1 C5 H5 O17 0.93 2.55 3.347(6) 143.8 1 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.812 _refine_diff_density_min -0.506 _refine_diff_density_rms 0.104 # Attachment '2_kkb466fm_FINAL_rev_1.cif' data_kkb466fm _database_code_depnum_ccdc_archive 'CCDC 603376' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H34 N8 O11 Zn2' _chemical_formula_weight 813.4 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.7579(7) _cell_length_b 16.5516(11) _cell_length_c 19.2846(13) _cell_angle_alpha 90.00 _cell_angle_beta 96.3070(10) _cell_angle_gamma 90.00 _cell_volume 3413.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1672 _exptl_absorpt_coefficient_mu 1.477 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5896 _exptl_absorpt_correction_T_max 0.8427 _exptl_absorpt_process_details BRUKER-SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9969 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 28.24 _reflns_number_total 3922 _reflns_number_gt 3376 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0447P)^2^+1.7809P] 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 3922 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0770 _refine_ls_wR_factor_gt 0.0739 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.258522(16) 0.001515(10) 0.691854(9) 0.01672(8) Uani 1 1 d . . . N1 N 0.37634(13) 0.05279(8) 0.62773(7) 0.0189(3) Uani 1 1 d . . . C2 C 0.34306(17) 0.11855(11) 0.58932(9) 0.0249(4) Uani 1 1 d . . . C3 C 0.41562(16) 0.15319(11) 0.54266(9) 0.0243(4) Uani 1 1 d . . . C4 C 0.53117(15) 0.11772(9) 0.53398(8) 0.0174(3) Uani 1 1 d . . . C5 C 0.56558(15) 0.04873(10) 0.57312(8) 0.0184(3) Uani 1 1 d . . . C6 C 0.48755(16) 0.01891(10) 0.61877(9) 0.0185(3) Uani 1 1 d . . . N7 N 0.61151(13) 0.14634(8) 0.48814(7) 0.0182(3) Uani 1 1 d . . . C8 C 0.60159(15) 0.22015(9) 0.45343(8) 0.0170(3) Uani 1 1 d . . . O9 O 0.52001(11) 0.26905(7) 0.45959(6) 0.0226(3) Uani 1 1 d . . . N10 N 0.69641(13) 0.22951(8) 0.41156(7) 0.0182(3) Uani 1 1 d . . . C11 C 0.70859(14) 0.29196(9) 0.36485(8) 0.0167(3) Uani 1 1 d . . . C12 C 0.62927(15) 0.35906(10) 0.35561(8) 0.0186(3) Uani 1 1 d . . . C13 C 0.65074(15) 0.41555(10) 0.30581(8) 0.0195(3) Uani 1 1 d . . . N14 N 0.74359(12) 0.41005(8) 0.26466(7) 0.0176(3) Uani 1 1 d . . . C15 C 0.81985(15) 0.34560(10) 0.27429(8) 0.0186(3) Uani 1 1 d . . . C16 C 0.80714(15) 0.28672(10) 0.32335(8) 0.0184(3) Uani 1 1 d . . . O17 O 0.08838(12) -0.00536(7) 0.64522(7) 0.0222(3) Uani 1 1 d . . . C18 C 0.07826(15) -0.05320(10) 0.59278(8) 0.0193(3) Uani 1 1 d . . . O19 O 0.17069(11) -0.08525(7) 0.57015(6) 0.0232(3) Uani 1 1 d . . . C20 C -0.05238(17) -0.06975(12) 0.55942(10) 0.0254(4) Uani 1 1 d . . . O21 O 0.35261(11) -0.09527(7) 0.72186(6) 0.0261(3) Uani 1 1 d . . . C22 C 0.31137(16) -0.12340(10) 0.77615(9) 0.0225(3) Uani 1 1 d . . . O23 O 0.21885(15) -0.09622(9) 0.80001(8) 0.0397(3) Uani 1 1 d . . . C24 C 0.3841(2) -0.19271(12) 0.81249(11) 0.0320(4) Uani 1 1 d . . . O25 O 0.0000 -0.18210(14) 0.7500 0.0507(7) Uani 1 2 d S . . H2 H 0.262(2) 0.1439(13) 0.5943(11) 0.033(5) Uiso 1 1 d . . . H3 H 0.389(2) 0.2009(14) 0.5179(11) 0.037(6) Uiso 1 1 d . . . H5 H 0.6463(18) 0.0220(12) 0.5705(10) 0.018(5) Uiso 1 1 d . . . H6 H 0.5068(18) -0.0254(12) 0.6445(10) 0.019(5) Uiso 1 1 d . . . H7 H 0.6713(18) 0.1173(12) 0.4820(10) 0.019(5) Uiso 1 1 d . . . H10 H 0.7451(18) 0.1905(12) 0.4114(10) 0.021(5) Uiso 1 1 d . . . H12 H 0.564(2) 0.3666(12) 0.3816(11) 0.029(5) Uiso 1 1 d . . . H13 H 0.5985(18) 0.4602(13) 0.2996(10) 0.022(5) Uiso 1 1 d . . . H15 H 0.8850(17) 0.3411(11) 0.2436(9) 0.020(5) Uiso 1 1 d . . . H16 H 0.8665(18) 0.2413(12) 0.3266(10) 0.023(5) Uiso 1 1 d . . . H20A H -0.090(2) -0.0187(15) 0.5440(12) 0.036(6) Uiso 1 1 d . . . H20B H -0.105(2) -0.0909(15) 0.5925(13) 0.046(7) Uiso 1 1 d . . . H20C H -0.0497(19) -0.1038(13) 0.5207(11) 0.028(5) Uiso 1 1 d . . . H24A H 0.386(3) -0.2399(17) 0.7798(14) 0.063(8) Uiso 1 1 d . . . H24B H 0.469(2) -0.1773(14) 0.8234(12) 0.044(6) Uiso 1 1 d . . . H24C H 0.352(2) -0.2057(16) 0.8549(14) 0.055(8) Uiso 1 1 d . . . H25 H -0.055(2) -0.1507(16) 0.7325(14) 0.055(8) 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 Zn1 0.01653(12) 0.01802(12) 0.01602(11) 0.00027(6) 0.00357(8) 0.00086(6) N1 0.0195(7) 0.0194(7) 0.0185(6) 0.0009(5) 0.0044(5) 0.0014(5) C2 0.0223(8) 0.0264(9) 0.0272(9) 0.0044(7) 0.0078(7) 0.0055(7) C3 0.0222(8) 0.0245(9) 0.0272(9) 0.0064(7) 0.0078(7) 0.0050(7) C4 0.0184(7) 0.0189(8) 0.0150(7) -0.0027(6) 0.0020(6) -0.0022(6) C5 0.0181(8) 0.0176(8) 0.0195(7) -0.0027(6) 0.0021(6) 0.0015(6) C6 0.0207(8) 0.0165(7) 0.0180(7) 0.0004(6) 0.0007(6) 0.0006(6) N7 0.0180(6) 0.0178(7) 0.0199(7) 0.0009(5) 0.0066(5) 0.0023(5) C8 0.0185(7) 0.0178(8) 0.0147(7) -0.0022(6) 0.0014(6) -0.0015(6) O9 0.0263(6) 0.0193(6) 0.0238(6) 0.0007(5) 0.0106(5) 0.0034(5) N10 0.0181(7) 0.0166(7) 0.0206(7) 0.0010(5) 0.0051(5) 0.0025(5) C11 0.0174(7) 0.0175(7) 0.0149(7) -0.0010(6) 0.0005(6) -0.0016(6) C12 0.0177(7) 0.0200(8) 0.0188(7) -0.0013(6) 0.0055(6) 0.0011(6) C13 0.0182(8) 0.0201(8) 0.0203(8) -0.0009(6) 0.0028(6) 0.0020(6) N14 0.0164(6) 0.0191(7) 0.0176(6) 0.0004(5) 0.0029(5) 0.0002(5) C15 0.0162(7) 0.0214(8) 0.0185(7) -0.0027(6) 0.0039(6) -0.0011(6) C16 0.0170(7) 0.0183(8) 0.0200(7) -0.0021(6) 0.0023(6) 0.0023(6) O17 0.0188(6) 0.0268(7) 0.0210(6) -0.0046(4) 0.0019(5) 0.0029(4) C18 0.0207(8) 0.0187(8) 0.0187(7) 0.0033(6) 0.0033(6) 0.0014(6) O19 0.0207(6) 0.0238(6) 0.0259(6) -0.0008(5) 0.0058(5) 0.0055(5) C20 0.0209(8) 0.0320(10) 0.0232(8) -0.0048(7) 0.0013(7) 0.0009(7) O21 0.0250(6) 0.0262(6) 0.0272(6) 0.0073(5) 0.0029(5) 0.0061(5) C22 0.0221(8) 0.0215(8) 0.0233(8) -0.0042(6) -0.0010(7) -0.0053(7) O23 0.0467(8) 0.0324(8) 0.0437(8) 0.0028(6) 0.0219(7) 0.0039(6) C24 0.0334(11) 0.0296(10) 0.0306(10) 0.0104(8) -0.0071(8) -0.0053(8) O25 0.0349(13) 0.0318(12) 0.091(2) 0.000 0.0323(13) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O21 1.9486(12) . ? Zn1 O17 1.9520(13) . ? Zn1 N14 2.0468(13) 8_456 ? Zn1 N1 2.0494(13) . ? N1 C2 1.343(2) . ? N1 C6 1.349(2) . ? C2 C3 1.379(2) . ? C2 H2 0.98(2) . ? C3 C4 1.401(2) . ? C3 H3 0.95(2) . ? C4 N7 1.386(2) . ? C4 C5 1.396(2) . ? C5 C6 1.373(2) . ? C5 H5 0.981(19) . ? C6 H6 0.90(2) . ? N7 C8 1.391(2) . ? N7 H7 0.82(2) . ? C8 O9 1.2093(19) . ? C8 N10 1.377(2) . ? N10 C11 1.387(2) . ? N10 H10 0.83(2) . ? C11 C16 1.400(2) . ? C11 C12 1.400(2) . ? C12 C13 1.378(2) . ? C12 H12 0.91(2) . ? C13 N14 1.345(2) . ? C13 H13 0.93(2) . ? N14 C15 1.346(2) . ? N14 Zn1 2.0467(13) 8 ? C15 C16 1.376(2) . ? C15 H15 0.969(19) . ? C16 H16 0.98(2) . ? O17 C18 1.280(2) . ? C18 O19 1.2473(19) . ? C18 C20 1.505(2) . ? C20 H20A 0.97(2) . ? C20 H20B 0.96(3) . ? C20 H20C 0.94(2) . ? O21 C22 1.270(2) . ? C22 O23 1.227(2) . ? C22 C24 1.516(3) . ? C24 H24A 1.01(3) . ? C24 H24B 0.95(2) . ? C24 H24C 0.95(3) . ? O25 H25 0.83(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O21 Zn1 O17 121.27(5) . . ? O21 Zn1 N14 117.49(5) . 8_456 ? O17 Zn1 N14 102.56(5) . 8_456 ? O21 Zn1 N1 100.61(5) . . ? O17 Zn1 N1 110.91(5) . . ? N14 Zn1 N1 102.60(5) 8_456 . ? C2 N1 C6 116.91(14) . . ? C2 N1 Zn1 121.56(11) . . ? C6 N1 Zn1 121.40(11) . . ? N1 C2 C3 124.13(16) . . ? N1 C2 H2 118.5(13) . . ? C3 C2 H2 117.4(13) . . ? C2 C3 C4 118.49(16) . . ? C2 C3 H3 121.0(13) . . ? C4 C3 H3 120.5(13) . . ? N7 C4 C5 118.52(14) . . ? N7 C4 C3 123.82(15) . . ? C5 C4 C3 117.65(14) . . ? C6 C5 C4 119.74(15) . . ? C6 C5 H5 118.5(11) . . ? C4 C5 H5 121.7(11) . . ? N1 C6 C5 123.08(15) . . ? N1 C6 H6 115.1(12) . . ? C5 C6 H6 121.8(12) . . ? C4 N7 C8 125.92(14) . . ? C4 N7 H7 116.4(13) . . ? C8 N7 H7 117.6(13) . . ? O9 C8 N10 125.06(15) . . ? O9 C8 N7 123.95(14) . . ? N10 C8 N7 110.98(13) . . ? C8 N10 C11 126.40(14) . . ? C8 N10 H10 115.0(13) . . ? C11 N10 H10 118.2(13) . . ? N10 C11 C16 117.19(14) . . ? N10 C11 C12 125.05(14) . . ? C16 C11 C12 117.76(14) . . ? C13 C12 C11 118.72(15) . . ? C13 C12 H12 119.1(13) . . ? C11 C12 H12 122.1(13) . . ? N14 C13 C12 123.87(15) . . ? N14 C13 H13 117.1(12) . . ? C12 C13 H13 119.0(12) . . ? C13 N14 C15 116.94(14) . . ? C13 N14 Zn1 118.40(11) . 8 ? C15 N14 Zn1 124.66(11) . 8 ? N14 C15 C16 123.45(14) . . ? N14 C15 H15 116.6(11) . . ? C16 C15 H15 120.0(11) . . ? C15 C16 C11 119.22(15) . . ? C15 C16 H16 118.2(11) . . ? C11 C16 H16 122.6(11) . . ? C18 O17 Zn1 113.22(10) . . ? O19 C18 O17 122.54(15) . . ? O19 C18 C20 121.05(15) . . ? O17 C18 C20 116.41(14) . . ? C18 C20 H20A 108.2(14) . . ? C18 C20 H20B 111.7(14) . . ? H20A C20 H20B 105(2) . . ? C18 C20 H20C 109.9(13) . . ? H20A C20 H20C 109.1(18) . . ? H20B C20 H20C 112.4(19) . . ? C22 O21 Zn1 109.22(11) . . ? O23 C22 O21 123.11(17) . . ? O23 C22 C24 120.18(17) . . ? O21 C22 C24 116.69(16) . . ? C22 C24 H24A 110.1(16) . . ? C22 C24 H24B 109.5(14) . . ? H24A C24 H24B 105(2) . . ? C22 C24 H24C 110.6(16) . . ? H24A C24 H24C 114(2) . . ? H24B C24 H24C 108(2) . . ? 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 N7 H7 O19 0.82(2) 2.14(2) 2.8905(18) 152.8(18) 5_656 N10 H10 O19 0.83(2) 1.98(2) 2.7854(18) 163.6(19) 5_656 O25 H25 O23 0.83(2) 2.02(2) 2.828(2) 165(3) 2_556 C13 H13 O17 0.93(2) 2.491(19) 3.202(2) 133.6(15) 7_556 C16 H16 O25 0.98(2) 2.381(19) 3.154(2) 135.0(15) 5_656 C20 H20B O23 0.96(3) 2.53(3) 3.437(2) 158(2) 2_556 C20 H20C O9 0.94(2) 2.56(2) 3.429(2) 153.5(17) 3_445 C24 H24B O21 0.95(2) 2.58(2) 3.387(2) 143.2(18) 2_656 _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.439 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.066 # Attachment '3_kkb514cm_FINAL_rev.cif' data_kkb514cm _database_code_depnum_ccdc_archive 'CCDC 603377' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 N4 O7 S Zn' _chemical_formula_weight 437.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 '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 4.8526(5) _cell_length_b 16.2068(17) _cell_length_c 24.048(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.387(2) _cell_angle_gamma 90.00 _cell_volume 1860.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description PLATE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 1.474 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6829 _exptl_absorpt_correction_T_max 0.9167 _exptl_absorpt_process_details BRUKER-SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6739 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 22.50 _reflns_number_total 2390 _reflns_number_gt 2083 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0711P)^2^+2.9735P] 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 2390 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1242 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.161 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.20117(10) 0.01680(3) 0.18029(2) 0.0153(2) Uani 1 1 d . . . N1 N 0.1360(8) 0.0914(2) 0.24221(15) 0.0163(9) Uani 1 1 d . . . C2 C 0.2697(10) 0.0845(3) 0.2964(2) 0.0225(11) Uani 1 1 d . . . H2H H 0.4181 0.0457 0.3050 0.027 Uiso 1 1 calc R . . C3 C 0.2007(10) 0.1310(3) 0.33970(19) 0.0232(11) Uani 1 1 d . . . H3 H 0.2998 0.1242 0.3773 0.028 Uiso 1 1 calc R . . C4 C -0.0156(9) 0.1880(3) 0.32788(19) 0.0168(10) Uani 1 1 d . . . C5 C -0.1509(9) 0.1957(3) 0.27223(19) 0.0186(11) Uani 1 1 d . . . H5 H -0.2991 0.2342 0.2624 0.022 Uiso 1 1 calc R . . C6 C -0.0694(10) 0.1474(3) 0.23181(18) 0.0192(11) Uani 1 1 d . . . H6 H -0.1641 0.1539 0.1939 0.023 Uiso 1 1 calc R . . N7 N -0.1063(8) 0.2391(2) 0.36733(15) 0.0189(9) Uani 1 1 d . . . H7 H -0.2648 0.2656 0.3561 0.023 Uiso 1 1 calc R . . C8 C 0.0255(10) 0.2525(3) 0.42207(19) 0.0183(10) Uani 1 1 d . . . O9 O 0.2372(7) 0.2166(2) 0.44510(13) 0.0292(8) Uani 1 1 d . . . N10 N -0.1114(8) 0.3123(2) 0.44746(15) 0.0188(9) Uani 1 1 d . . . H10 H -0.2671 0.3319 0.4273 0.023 Uiso 1 1 calc R . . C11 C -0.0306(9) 0.3449(3) 0.50120(18) 0.0172(10) Uani 1 1 d . . . C12 C 0.1855(12) 0.3177(3) 0.5423(2) 0.0357(14) Uani 1 1 d . . . H12 H 0.2948 0.2716 0.5352 0.043 Uiso 1 1 calc R . . C13 C 0.2424(12) 0.3571(3) 0.5931(2) 0.0354(14) Uani 1 1 d . . . H13 H 0.3909 0.3364 0.6209 0.042 Uiso 1 1 calc R . . N14 N 0.1015(8) 0.4230(2) 0.60630(15) 0.0178(9) Uani 1 1 d . . . C15 C -0.1092(12) 0.4488(4) 0.5667(2) 0.0415(16) Uani 1 1 d . . . H15 H -0.2140 0.4955 0.5746 0.050 Uiso 1 1 calc R . . C16 C -0.1814(12) 0.4110(4) 0.5153(2) 0.0440(17) Uani 1 1 d . . . H16 H -0.3375 0.4307 0.4890 0.053 Uiso 1 1 calc R . . O17 O 0.5896(6) -0.01855(19) 0.19769(14) 0.0230(8) Uani 1 1 d . . . S18 S 0.6850(2) -0.09488(7) 0.17148(5) 0.0160(3) Uani 1 1 d . . . O19 O 0.6167(6) -0.1683(2) 0.20093(14) 0.0240(8) Uani 1 1 d . . . O20 O 0.5553(7) -0.0975(2) 0.11211(14) 0.0290(8) Uani 1 1 d . . . O21 O 0.9941(6) -0.08682(18) 0.17742(13) 0.0210(7) Uani 1 1 d . . . O22 O 0.7246(12) 0.2911(4) 0.1306(2) 0.0752(15) Uani 1 1 d . . . H22H H 0.6339 0.2779 0.0987 0.113 Uiso 1 1 calc R . . C23 C 0.609(5) 0.3647(13) 0.1496(13) 0.345(19) Uani 1 1 d . . . H23A H 0.7428 0.3837 0.1832 0.414 Uiso 1 1 calc R . . H23B H 0.6121 0.4067 0.1198 0.414 Uiso 1 1 calc R . . C24 C 0.353(3) 0.3679(8) 0.1633(5) 0.128(4) Uani 1 1 d . . . H24A H 0.3534 0.4135 0.1907 0.154 Uiso 1 1 calc R . . H24B H 0.2188 0.3833 0.1288 0.154 Uiso 1 1 calc R . . O25 O 0.2551(12) 0.3035(4) 0.1843(2) 0.0733(15) Uani 1 1 d . . . H25 H 0.3054 0.3036 0.2196 0.110 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0143(3) 0.0168(4) 0.0143(3) -0.0004(2) 0.0010(2) 0.0028(2) N1 0.017(2) 0.017(2) 0.014(2) -0.0011(16) 0.0017(16) 0.0029(17) C2 0.018(3) 0.024(3) 0.024(3) 0.000(2) 0.000(2) 0.007(2) C3 0.027(3) 0.027(3) 0.013(2) 0.000(2) -0.003(2) 0.009(2) C4 0.018(2) 0.013(2) 0.020(3) -0.003(2) 0.004(2) -0.003(2) C5 0.017(2) 0.017(2) 0.020(3) 0.000(2) -0.002(2) 0.007(2) C6 0.023(3) 0.021(3) 0.011(2) -0.001(2) -0.0045(19) 0.002(2) N7 0.017(2) 0.021(2) 0.017(2) -0.0019(17) -0.0006(16) 0.0039(17) C8 0.019(3) 0.018(2) 0.017(3) -0.001(2) 0.004(2) -0.001(2) O9 0.028(2) 0.034(2) 0.0217(18) -0.0053(16) -0.0057(15) 0.0120(17) N10 0.021(2) 0.021(2) 0.013(2) -0.0044(17) -0.0004(16) 0.0028(17) C11 0.018(3) 0.018(2) 0.014(2) 0.002(2) 0.0005(19) -0.003(2) C12 0.037(3) 0.037(3) 0.029(3) -0.011(3) -0.004(3) 0.018(3) C13 0.036(3) 0.040(3) 0.024(3) -0.010(3) -0.011(2) 0.011(3) N14 0.018(2) 0.019(2) 0.016(2) -0.0001(17) 0.0005(17) -0.0030(17) C15 0.052(4) 0.043(4) 0.025(3) -0.011(3) -0.005(3) 0.032(3) C16 0.046(4) 0.058(4) 0.020(3) -0.014(3) -0.017(3) 0.030(3) O17 0.0147(17) 0.0195(19) 0.033(2) -0.0050(14) 0.0007(15) 0.0024(13) S18 0.0113(6) 0.0175(6) 0.0189(6) 0.0000(5) 0.0017(5) -0.0004(4) O19 0.0176(17) 0.0202(18) 0.0323(19) 0.0069(15) -0.0005(14) -0.0004(14) O20 0.0248(19) 0.040(2) 0.0212(18) -0.0009(15) 0.0005(15) -0.0113(16) O21 0.0144(17) 0.0191(17) 0.0303(18) -0.0009(14) 0.0062(14) 0.0023(13) O22 0.074(4) 0.083(4) 0.066(4) 0.008(3) 0.008(3) 0.019(3) C23 0.24(2) 0.22(2) 0.66(5) 0.12(3) 0.30(3) 0.12(2) C24 0.144(12) 0.115(10) 0.133(11) -0.035(8) 0.043(9) -0.016(9) O25 0.087(4) 0.083(4) 0.047(3) -0.005(3) 0.003(3) -0.014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O17 1.942(3) . ? Zn1 O21 1.952(3) 1_455 ? Zn1 N1 1.987(4) . ? Zn1 N14 2.010(4) 4_565 ? N1 C6 1.338(6) . ? N1 C2 1.352(6) . ? C2 C3 1.374(7) . ? C2 H2H 0.9500 . ? C3 C4 1.389(7) . ? C3 H3 0.9500 . ? C4 C5 1.386(6) . ? C4 N7 1.389(6) . ? C5 C6 1.361(6) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? N7 C8 1.373(6) . ? N7 H7 0.8800 . ? C8 O9 1.222(6) . ? C8 N10 1.379(6) . ? N10 C11 1.386(6) . ? N10 H10 0.8800 . ? C11 C16 1.374(7) . ? C11 C12 1.377(7) . ? C12 C13 1.363(8) . ? C12 H12 0.9500 . ? C13 N14 1.338(6) . ? C13 H13 0.9500 . ? N14 C15 1.332(6) . ? N14 Zn1 2.010(4) 4_566 ? C15 C16 1.369(7) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? O17 S18 1.499(3) . ? S18 O20 1.453(3) . ? S18 O19 1.453(3) . ? S18 O21 1.487(3) . ? O21 Zn1 1.952(3) 1_655 ? O22 C23 1.427(19) . ? O22 H22H 0.8400 . ? C23 C24 1.345(17) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 O25 1.287(12) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? O25 H25 0.8400 . ? 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 O17 Zn1 O21 103.13(13) . 1_455 ? O17 Zn1 N1 107.30(14) . . ? O21 Zn1 N1 113.56(14) 1_455 . ? O17 Zn1 N14 113.77(15) . 4_565 ? O21 Zn1 N14 110.23(14) 1_455 4_565 ? N1 Zn1 N14 108.83(15) . 4_565 ? C6 N1 C2 116.6(4) . . ? C6 N1 Zn1 119.1(3) . . ? C2 N1 Zn1 124.0(3) . . ? N1 C2 C3 123.0(4) . . ? N1 C2 H2H 118.5 . . ? C3 C2 H2H 118.5 . . ? C2 C3 C4 119.2(4) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 117.8(4) . . ? C5 C4 N7 116.9(4) . . ? C3 C4 N7 125.3(4) . . ? C6 C5 C4 119.3(4) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? N1 C6 C5 124.0(4) . . ? N1 C6 H6 118.0 . . ? C5 C6 H6 118.0 . . ? C8 N7 C4 126.8(4) . . ? C8 N7 H7 116.6 . . ? C4 N7 H7 116.6 . . ? O9 C8 N7 124.6(4) . . ? O9 C8 N10 124.5(4) . . ? N7 C8 N10 110.9(4) . . ? C8 N10 C11 127.1(4) . . ? C8 N10 H10 116.5 . . ? C11 N10 H10 116.5 . . ? C16 C11 C12 116.3(4) . . ? C16 C11 N10 116.9(4) . . ? C12 C11 N10 126.7(4) . . ? C13 C12 C11 119.9(5) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? N14 C13 C12 123.9(5) . . ? N14 C13 H13 118.1 . . ? C12 C13 H13 118.1 . . ? C15 N14 C13 116.1(4) . . ? C15 N14 Zn1 120.8(3) . 4_566 ? C13 N14 Zn1 123.1(3) . 4_566 ? N14 C15 C16 123.0(5) . . ? N14 C15 H15 118.5 . . ? C16 C15 H15 118.5 . . ? C15 C16 C11 120.7(5) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? S18 O17 Zn1 120.93(19) . . ? O20 S18 O19 111.0(2) . . ? O20 S18 O21 110.34(19) . . ? O19 S18 O21 109.87(18) . . ? O20 S18 O17 109.0(2) . . ? O19 S18 O17 110.85(19) . . ? O21 S18 O17 105.64(18) . . ? S18 O21 Zn1 125.66(19) . 1_655 ? C23 O22 H22H 109.5 . . ? C24 C23 O22 123(2) . . ? C24 C23 H23A 106.6 . . ? O22 C23 H23A 106.6 . . ? C24 C23 H23B 106.6 . . ? O22 C23 H23B 106.6 . . ? H23A C23 H23B 106.5 . . ? O25 C24 C23 119.2(15) . . ? O25 C24 H24A 107.5 . . ? C23 C24 H24A 107.5 . . ? O25 C24 H24B 107.5 . . ? C23 C24 H24B 107.5 . . ? H24A C24 H24B 107.0 . . ? C24 O25 H25 109.5 . . ? 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 N7 H7 O19 0.88 2.26 3.101(5) 160.4 2 N10 H10 O20 0.88 1.92 2.778(5) 164.6 2 O25 H25 O19 0.84 1.93 2.756(6) 165.6 2_655 C5 H5 O19 0.95 2.48 3.303(5) 145.3 2 C15 H15 O20 0.95 2.27 3.208(6) 168.1 4_466 C16 H16 O20 0.95 2.51 3.270(6) 136.8 2 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.961 _refine_diff_density_min -0.517 _refine_diff_density_rms 0.182 # Attachment '4_kkb457c_FINAL_rev.cif' data_kkb457c _database_code_depnum_ccdc_archive 'CCDC 603378' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 Cl2 N4 O Zn' _chemical_formula_weight 350.50 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 Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 18.371(3) _cell_length_b 9.8668(16) _cell_length_c 15.866(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2875.9(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ROD _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.619 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 2.075 _exptl_absorpt_correction_type MULTI-SCAN' _exptl_absorpt_correction_T_min 0.4486 _exptl_absorpt_correction_T_max 0.7742 _exptl_absorpt_process_details BRUKER-SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3975 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 28.24 _reflns_number_total 1558 _reflns_number_gt 1494 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0384P)^2^+0.0311P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.001(15) _refine_ls_number_reflns 1558 _refine_ls_number_parameters 88 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0317 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0738 _refine_ls_wR_factor_gt 0.0731 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 0.2500 -0.2500 0.54371(2) 0.03067(14) Uani 1 2 d S . . Cl2 Cl 0.17418(5) -0.11830(9) 0.47181(6) 0.0461(2) Uani 1 1 d . . . N1 N 0.19036(15) -0.3606(3) 0.62728(18) 0.0365(6) Uani 1 1 d . . . C2 C 0.1243(2) -0.3208(3) 0.6533(2) 0.0479(8) Uani 1 1 d . . . H2 H 0.1022 -0.2479 0.6263 0.058 Uiso 1 1 calc R . . C3 C 0.0882(2) -0.3828(4) 0.7174(3) 0.0533(9) Uani 1 1 d . . . H3 H 0.0421 -0.3534 0.7331 0.064 Uiso 1 1 calc R . . C4 C 0.1211(2) -0.4907(3) 0.7595(3) 0.0470(8) Uani 1 1 d . . . H4 H 0.0982 -0.5322 0.8050 0.056 Uiso 1 1 calc R . . C5 C 0.18817(17) -0.5344(3) 0.7320(2) 0.0328(6) Uani 1 1 d . . . C6 C 0.22228(18) -0.4653(3) 0.6677(2) 0.0334(6) Uani 1 1 d . . . H6 H 0.2689 -0.4916 0.6517 0.040 Uiso 1 1 calc R . . N7 N 0.22274(14) -0.6456(2) 0.77162(17) 0.0343(5) Uani 1 1 d . . . H7 H 0.2267 -0.6480 0.8256 0.041 Uiso 1 1 calc R . . C8 C 0.2500 -0.7500 0.7235(3) 0.0270(8) Uani 1 2 d S . . O9 O 0.2500 -0.7500 0.64786(19) 0.0337(6) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0365(2) 0.0301(2) 0.0254(2) 0.000 0.000 0.0026(2) Cl2 0.0470(5) 0.0571(5) 0.0342(4) 0.0080(4) -0.0020(4) 0.0167(4) N1 0.0390(15) 0.0338(13) 0.0366(16) 0.0023(11) 0.0040(12) 0.0008(11) C2 0.047(2) 0.0374(16) 0.060(2) 0.0104(16) 0.0044(16) 0.0139(14) C3 0.0431(18) 0.058(2) 0.058(2) 0.0086(16) 0.0214(18) 0.0137(16) C4 0.045(2) 0.0458(18) 0.050(2) 0.0078(15) 0.0182(15) 0.0030(14) C5 0.0379(16) 0.0309(13) 0.0297(14) -0.0020(11) 0.0061(12) 0.0008(11) C6 0.0321(15) 0.0341(14) 0.0341(16) -0.0016(12) 0.0049(12) 0.0036(12) N7 0.0431(14) 0.0342(12) 0.0257(12) 0.0004(9) 0.0050(11) 0.0048(11) C8 0.0240(19) 0.032(2) 0.0246(19) 0.000 0.000 -0.0033(13) O9 0.0367(16) 0.0371(15) 0.0272(15) 0.000 0.000 0.0026(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N1 2.037(3) . ? Zn1 N1 2.037(3) 14_545 ? Zn1 Cl2 2.2203(9) 14_545 ? Zn1 Cl2 2.2204(9) . ? N1 C2 1.341(4) . ? N1 C6 1.350(4) . ? C2 C3 1.360(5) . ? C3 C4 1.395(5) . ? C4 C5 1.376(5) . ? C5 C6 1.378(4) . ? C5 N7 1.415(4) . ? N7 C8 1.376(3) . ? C8 O9 1.200(5) . ? C8 N7 1.376(3) 14_535 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn1 N1 98.79(17) . 14_545 ? N1 Zn1 Cl2 110.99(7) . 14_545 ? N1 Zn1 Cl2 108.10(8) 14_545 14_545 ? N1 Zn1 Cl2 108.09(8) . . ? N1 Zn1 Cl2 110.99(7) 14_545 . ? Cl2 Zn1 Cl2 118.17(5) 14_545 . ? C2 N1 C6 118.1(3) . . ? C2 N1 Zn1 122.0(2) . . ? C6 N1 Zn1 119.1(2) . . ? N1 C2 C3 122.6(3) . . ? C2 C3 C4 119.4(3) . . ? C5 C4 C3 118.4(3) . . ? C4 C5 C6 119.1(3) . . ? C4 C5 N7 120.3(3) . . ? C6 C5 N7 120.6(3) . . ? N1 C6 C5 122.2(3) . . ? C8 N7 C5 119.8(3) . . ? O9 C8 N7 123.68(17) . . ? O9 C8 N7 123.68(17) . 14_535 ? N7 C8 N7 112.6(3) . 14_535 ? 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 N7 H7 Cl2 0.86 2.53 3.310(3) 151.4 5_545 C4 H4 O9 0.93 2.35 3.127(4) 140.7 4 _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.565 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.067 # Attachment '5_kkb511d_FINAL.cif' data_kkb511d _database_code_depnum_ccdc_archive 'CCDC 603379' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 Cl3 N4 O5 Zn' _chemical_formula_weight 517.06 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' Cl Cl 0.1484 0.1585 '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' H H 0.0000 0.0000 '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 9.2135(16) _cell_length_b 12.441(2) _cell_length_c 19.292(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.447(4) _cell_angle_gamma 90.00 _cell_volume 2201.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description NEEDLE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.560 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 1.514 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6350 _exptl_absorpt_correction_T_max 0.9419 _exptl_absorpt_process_details BRUKER-SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8549 _diffrn_reflns_av_R_equivalents 0.0965 _diffrn_reflns_av_sigmaI/netI 0.1313 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 22.48 _reflns_number_total 2865 _reflns_number_gt 1873 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0653P)^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 2865 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1127 _refine_ls_R_factor_gt 0.0686 _refine_ls_wR_factor_ref 0.1572 _refine_ls_wR_factor_gt 0.1389 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.13803(10) -0.10818(7) 0.30100(5) 0.0155(3) Uani 1 1 d . . . N1 N 0.1525(7) 0.0118(5) 0.3721(3) 0.0140(16) Uani 1 1 d . . . C2 C 0.1637(8) -0.0133(6) 0.4406(4) 0.015(2) Uani 1 1 d . . . H2 H 0.1641 -0.0867 0.4541 0.018 Uiso 1 1 calc R . . C3 C 0.1747(9) 0.0652(6) 0.4914(4) 0.018(2) Uani 1 1 d . . . H3 H 0.1861 0.0455 0.5392 0.021 Uiso 1 1 calc R . . C4 C 0.1691(9) 0.1731(7) 0.4728(4) 0.020(2) Uani 1 1 d . . . H4 H 0.1730 0.2280 0.5071 0.024 Uiso 1 1 calc R . . C5 C 0.1578(8) 0.1979(6) 0.4028(4) 0.016(2) Uani 1 1 d . . . C6 C 0.1504(8) 0.1153(7) 0.3541(4) 0.018(2) Uani 1 1 d . . . H6 H 0.1436 0.1332 0.3060 0.021 Uiso 1 1 calc R . . N7 N 0.1462(7) 0.3036(5) 0.3772(3) 0.0160(17) Uani 1 1 d . . . H7 H 0.0888 0.3155 0.3389 0.019 Uiso 1 1 calc R . . C8 C 0.2195(9) 0.3892(7) 0.4088(4) 0.018(2) Uani 1 1 d . . . O9 O 0.3067(6) 0.3816(4) 0.4601(3) 0.0231(14) Uani 1 1 d . . . N10 N 0.1878(7) 0.4846(5) 0.3740(3) 0.0213(18) Uani 1 1 d . . . H10 H 0.1151 0.4828 0.3410 0.026 Uiso 1 1 calc R . . C11 C 0.2574(9) 0.5828(6) 0.3852(4) 0.016(2) Uani 1 1 d . . . C12 C 0.3880(10) 0.5982(7) 0.4248(4) 0.024(2) Uani 1 1 d . . . H12 H 0.4361 0.5399 0.4491 0.029 Uiso 1 1 calc R . . C13 C 0.4481(9) 0.7008(6) 0.4284(4) 0.020(2) Uani 1 1 d . . . H13 H 0.5372 0.7137 0.4561 0.024 Uiso 1 1 calc R . . C14 C 0.3785(9) 0.7825(6) 0.3922(4) 0.017(2) Uani 1 1 d . . . H14 H 0.4228 0.8515 0.3934 0.021 Uiso 1 1 calc R . . N15 N 0.2497(7) 0.7692(5) 0.3547(3) 0.0156(17) Uani 1 1 d . . . C16 C 0.1907(9) 0.6691(7) 0.3511(4) 0.016(2) Uani 1 1 d . . . H16 H 0.1001 0.6584 0.3241 0.019 Uiso 1 1 calc R . . O17 O -0.0505(6) -0.1689(4) 0.2628(3) 0.0178(14) Uani 1 1 d . . . C18 C -0.1349(10) -0.1817(6) 0.3127(5) 0.019(2) Uani 1 1 d . . . O19 O -0.0925(7) -0.1724(5) 0.3743(3) 0.0304(16) Uani 1 1 d . . . C20 C -0.2907(9) -0.2124(7) 0.2901(5) 0.032(3) Uani 1 1 d . . . H20A H -0.2963 -0.2899 0.2811 0.048 Uiso 1 1 calc R . . H20B H -0.3244 -0.1733 0.2475 0.048 Uiso 1 1 calc R . . H20C H -0.3525 -0.1940 0.3270 0.048 Uiso 1 1 calc R . . O21 O 0.0953(6) 0.0202(4) 0.2023(3) 0.0216(14) Uani 1 1 d . . . C22 C 0.2012(10) -0.0323(7) 0.1825(5) 0.024(2) Uani 1 1 d . . . O23 O 0.2685(6) -0.1002(5) 0.2225(3) 0.0238(14) Uani 1 1 d . . . C24 C 0.2511(11) -0.0126(8) 0.1131(5) 0.045(3) Uani 1 1 d . . . H24A H 0.1819 -0.0449 0.0773 0.067 Uiso 1 1 calc R . . H24B H 0.3476 -0.0448 0.1109 0.067 Uiso 1 1 calc R . . H24C H 0.2569 0.0650 0.1050 0.067 Uiso 1 1 calc R . . C25 C 0.6213(10) 0.1678(8) 0.3206(5) 0.038(3) Uani 1 1 d . . . H25 H 0.6210 0.2292 0.2871 0.046 Uiso 1 1 calc R . . Cl26 Cl 0.5424(3) 0.2118(3) 0.39367(16) 0.0678(10) Uani 1 1 d . . . Cl27 Cl 0.5191(3) 0.06285(19) 0.27953(14) 0.0421(7) Uani 1 1 d . . . Cl28 Cl 0.8029(3) 0.1271(2) 0.34091(16) 0.0596(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0251(6) 0.0069(5) 0.0140(6) -0.0003(5) -0.0010(4) -0.0007(5) N1 0.028(4) 0.007(4) 0.008(4) 0.001(3) 0.000(3) 0.000(3) C2 0.021(5) 0.008(5) 0.019(6) -0.002(4) 0.006(4) 0.001(4) C3 0.029(5) 0.013(5) 0.012(5) 0.005(4) 0.007(4) -0.001(4) C4 0.035(6) 0.015(5) 0.012(6) -0.002(4) 0.008(4) -0.004(4) C5 0.015(5) 0.010(5) 0.021(6) -0.002(4) -0.005(4) -0.005(4) C6 0.017(5) 0.024(6) 0.011(5) 0.005(4) -0.005(4) -0.001(4) N7 0.018(4) 0.011(4) 0.017(4) 0.001(3) -0.009(3) 0.000(3) C8 0.023(5) 0.015(5) 0.018(5) -0.002(5) 0.007(4) 0.003(5) O9 0.031(4) 0.013(3) 0.023(4) 0.000(3) -0.010(3) 0.000(3) N10 0.029(5) 0.013(4) 0.020(5) -0.002(3) -0.005(3) 0.003(3) C11 0.026(5) 0.003(5) 0.020(5) -0.001(4) -0.002(4) -0.003(4) C12 0.039(6) 0.014(5) 0.018(5) 0.002(4) 0.001(4) 0.012(5) C13 0.022(5) 0.013(5) 0.024(6) 0.001(4) -0.006(4) 0.000(4) C14 0.021(5) 0.011(5) 0.020(5) -0.002(4) -0.003(4) -0.008(4) N15 0.023(4) 0.005(4) 0.019(4) 0.001(3) 0.003(3) 0.001(3) C16 0.017(5) 0.022(5) 0.009(5) -0.001(4) 0.001(4) 0.011(4) O17 0.022(3) 0.017(3) 0.014(4) 0.002(3) 0.002(3) -0.001(3) C18 0.030(6) 0.003(5) 0.025(6) 0.000(4) -0.003(5) 0.009(4) O19 0.039(4) 0.030(4) 0.022(4) -0.004(3) 0.000(3) -0.004(3) C20 0.026(6) 0.026(6) 0.047(7) -0.002(5) 0.012(5) -0.002(4) O21 0.035(4) 0.014(3) 0.014(4) -0.001(3) -0.005(3) -0.002(3) C22 0.027(6) 0.014(5) 0.030(6) -0.008(5) 0.003(5) 0.003(4) O23 0.029(4) 0.018(3) 0.024(4) 0.006(3) 0.001(3) 0.003(3) C24 0.052(7) 0.052(7) 0.034(7) 0.020(6) 0.018(5) 0.013(6) C25 0.027(6) 0.049(7) 0.038(7) 0.004(5) 0.002(5) -0.009(5) Cl26 0.058(2) 0.095(3) 0.055(2) -0.0328(19) 0.0277(17) -0.0244(18) Cl27 0.0450(17) 0.0242(14) 0.0560(19) 0.0007(12) -0.0006(14) 0.0038(12) Cl28 0.0306(16) 0.074(2) 0.073(2) 0.0345(18) -0.0022(14) 0.0054(15) _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 O17 1.972(5) . ? Zn1 O23 2.022(5) . ? Zn1 N1 2.024(6) . ? Zn1 N15 2.063(6) 1_545 ? Zn1 O21 2.488(5) . ? Zn1 C22 2.591(9) . ? N1 C6 1.333(10) . ? N1 C2 1.352(10) . ? C2 C3 1.381(10) . ? C2 H2 0.9500 . ? C3 C4 1.389(11) . ? C3 H3 0.9500 . ? C4 C5 1.380(11) . ? C4 H4 0.9500 . ? C5 C6 1.389(11) . ? C5 N7 1.405(10) . ? C6 H6 0.9500 . ? N7 C8 1.373(10) . ? N7 H7 0.8800 . ? C8 O9 1.218(9) . ? C8 N10 1.380(10) . ? N10 C11 1.387(10) . ? N10 H10 0.8800 . ? C11 C16 1.374(11) . ? C11 C12 1.376(11) . ? C12 C13 1.390(11) . ? C12 H12 0.9500 . ? C13 C14 1.360(11) . ? C13 H13 0.9500 . ? C14 N15 1.339(10) . ? C14 H14 0.9500 . ? N15 C16 1.358(10) . ? N15 Zn1 2.063(6) 1_565 ? C16 H16 0.9500 . ? O17 C18 1.303(10) . ? C18 O19 1.220(10) . ? C18 C20 1.509(12) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? O21 C22 1.263(9) . ? C22 O23 1.267(10) . ? C22 C24 1.476(12) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 Cl26 1.735(10) . ? C25 Cl27 1.754(10) . ? C25 Cl28 1.756(9) . ? C25 H25 1.0000 . ? 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 O17 Zn1 O23 107.7(2) . . ? O17 Zn1 N1 122.3(2) . . ? O23 Zn1 N1 117.8(2) . . ? O17 Zn1 N15 106.5(2) . 1_545 ? O23 Zn1 N15 96.3(2) . 1_545 ? N1 Zn1 N15 101.9(3) . 1_545 ? O17 Zn1 O21 83.7(2) . . ? O23 Zn1 O21 57.1(2) . . ? N1 Zn1 O21 92.4(2) . . ? N15 Zn1 O21 153.4(2) 1_545 . ? O17 Zn1 C22 94.2(3) . . ? O23 Zn1 C22 28.6(2) . . ? N1 Zn1 C22 108.9(3) . . ? N15 Zn1 C22 124.7(3) 1_545 . ? O21 Zn1 C22 28.7(2) . . ? C6 N1 C2 118.5(7) . . ? C6 N1 Zn1 122.4(5) . . ? C2 N1 Zn1 119.1(5) . . ? N1 C2 C3 121.6(7) . . ? N1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C2 C3 C4 120.1(8) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 117.8(8) . . ? C5 C4 H4 121.1 . . ? C3 C4 H4 121.1 . . ? C4 C5 C6 119.4(8) . . ? C4 C5 N7 123.3(7) . . ? C6 C5 N7 117.2(7) . . ? N1 C6 C5 122.6(8) . . ? N1 C6 H6 118.7 . . ? C5 C6 H6 118.7 . . ? C8 N7 C5 123.6(7) . . ? C8 N7 H7 118.2 . . ? C5 N7 H7 118.2 . . ? O9 C8 N7 124.0(8) . . ? O9 C8 N10 123.7(8) . . ? N7 C8 N10 112.3(8) . . ? C8 N10 C11 127.4(7) . . ? C8 N10 H10 116.3 . . ? C11 N10 H10 116.3 . . ? C16 C11 C12 119.0(7) . . ? C16 C11 N10 115.8(8) . . ? C12 C11 N10 125.2(7) . . ? C11 C12 C13 118.6(8) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C14 C13 C12 119.6(8) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? N15 C14 C13 122.4(8) . . ? N15 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? C14 N15 C16 118.1(7) . . ? C14 N15 Zn1 123.6(5) . 1_565 ? C16 N15 Zn1 118.3(6) . 1_565 ? N15 C16 C11 122.2(8) . . ? N15 C16 H16 118.9 . . ? C11 C16 H16 118.9 . . ? C18 O17 Zn1 109.7(5) . . ? O19 C18 O17 123.3(8) . . ? O19 C18 C20 120.9(8) . . ? O17 C18 C20 115.8(8) . . ? 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 . . ? C22 O21 Zn1 80.2(5) . . ? O21 C22 O23 120.5(8) . . ? O21 C22 C24 120.3(8) . . ? O23 C22 C24 119.2(8) . . ? O21 C22 Zn1 71.1(5) . . ? O23 C22 Zn1 49.9(4) . . ? C24 C22 Zn1 167.4(7) . . ? C22 O23 Zn1 101.5(5) . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? Cl26 C25 Cl27 110.7(5) . . ? Cl26 C25 Cl28 111.9(6) . . ? Cl27 C25 Cl28 110.2(6) . . ? Cl26 C25 H25 107.9 . . ? Cl27 C25 H25 107.9 . . ? Cl28 C25 H25 107.9 . . ? 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 N7 H7 O17 0.88 1.97 2.783(9) 152.9 2 N10 H10 O21 0.88 2.09 2.905(9) 153.8 2 C13 H13 O9 0.95 2.38 3.139(11) 137.1 3_666 C16 H16 O21 0.95 2.51 3.305(10) 141.6 2 C25 H25 O23 1.00 2.37 3.197(11) 139.5 2_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 22.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.029 _refine_diff_density_min -0.561 _refine_diff_density_rms 0.117 # Attachment '6_kkb59bm_FINAL.cif' data_kkb59bm _database_code_depnum_ccdc_archive 'CCDC 603380' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 N4 O9 S Zn' _chemical_formula_weight 461.75 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.7362(14) _cell_length_b 10.8978(19) _cell_length_c 21.528(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.732(4) _cell_angle_gamma 90.00 _cell_volume 1802.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.702 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 1.534 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5517 _exptl_absorpt_correction_T_max 0.7489 _exptl_absorpt_process_details BRUKER-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 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10539 _diffrn_reflns_av_R_equivalents 0.0558 _diffrn_reflns_av_sigmaI/netI 0.0809 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.34 _reflns_number_total 4172 _reflns_number_gt 2990 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER AXS SMART 3' _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'BRUKER SHELXLTL' _computing_publication_material 'MERCURY 1.4' _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^)+(0.0464P)^2^+0.1621P] 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 4172 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0872 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.1049 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.41310(6) 0.47096(4) 0.221106(19) 0.02326(14) Uani 1 1 d . . . N1 N 0.3508(4) 0.4178(3) 0.12386(14) 0.0286(7) Uani 1 1 d . . . C2 C 0.3853(6) 0.3035(4) 0.10692(19) 0.0402(11) Uani 1 1 d . . . H2 H 0.4270 0.2476 0.1377 0.048 Uiso 1 1 calc R . . C3 C 0.3617(7) 0.2653(4) 0.04608(19) 0.0478(13) Uani 1 1 d . . . H3 H 0.3866 0.1848 0.0359 0.057 Uiso 1 1 calc R . . C4 C 0.3009(6) 0.3473(4) 0.00009(18) 0.0423(11) Uani 1 1 d . . . H4 H 0.2852 0.3232 -0.0416 0.051 Uiso 1 1 calc R . . C5 C 0.2631(5) 0.4666(3) 0.01677(17) 0.0295(9) Uani 1 1 d . . . C6 C 0.2895(5) 0.4973(3) 0.07975(17) 0.0269(9) Uani 1 1 d . . . H6A H 0.2634 0.5766 0.0916 0.032 Uiso 1 1 calc R . . N7 N 0.1933(5) 0.5450(3) -0.03140(14) 0.0350(8) Uani 1 1 d . . . H7A H 0.1535 0.5103 -0.0660 0.042 Uiso 1 1 calc R . . C8 C 0.1813(6) 0.6690(4) -0.02981(17) 0.0321(9) Uani 1 1 d . . . O9 O 0.2250(5) 0.7303(3) 0.01713(12) 0.0483(9) Uani 1 1 d . . . N10 N 0.1146(5) 0.7188(3) -0.08578(14) 0.0360(9) Uani 1 1 d . . . H10 H 0.0852 0.6681 -0.1158 0.043 Uiso 1 1 calc R . . C11 C 0.0890(5) 0.8440(3) -0.09959(17) 0.0291(9) Uani 1 1 d . . . C12 C 0.0268(5) 0.8737(3) -0.16043(17) 0.0299(9) Uani 1 1 d . . . H12 H 0.0075 0.8099 -0.1891 0.036 Uiso 1 1 calc R . . N13 N -0.0073(4) 0.9871(3) -0.18087(14) 0.0285(7) Uani 1 1 d . . . C14 C 0.0232(6) 1.0786(4) -0.13933(18) 0.0376(11) Uani 1 1 d . . . H14 H 0.0017 1.1590 -0.1525 0.045 Uiso 1 1 calc R . . C15 C 0.0850(7) 1.0572(4) -0.07821(19) 0.0514(13) Uani 1 1 d . . . H15 H 0.1028 1.1228 -0.0505 0.062 Uiso 1 1 calc R . . C16 C 0.1213(6) 0.9400(4) -0.05715(19) 0.0441(12) Uani 1 1 d . . . H16 H 0.1660 0.9252 -0.0158 0.053 Uiso 1 1 calc R . . O17 O 0.1813(3) 0.5799(2) 0.21887(12) 0.0289(6) Uani 1 1 d . . . S18 S -0.00631(12) 0.55576(8) 0.19932(4) 0.0247(2) Uani 1 1 d . . . O19 O -0.0375(3) 0.4224(2) 0.20275(13) 0.0323(6) Uani 1 1 d . . . O20 O -0.1079(3) 0.6193(2) 0.24257(13) 0.0369(7) Uani 1 1 d . . . O21 O -0.0549(4) 0.5987(3) 0.13569(12) 0.0462(8) Uani 1 1 d . . . O22 O 0.5448(4) 0.6282(3) 0.19838(15) 0.0361(7) Uani 1 1 d . . . H22A H 0.6483 0.6217 0.2114 0.054 Uiso 1 1 calc R . . O23 O 0.6340(4) 0.3582(3) 0.22611(15) 0.0377(7) Uani 1 1 d . . . H23A H 0.7152 0.3967 0.2143 0.057 Uiso 1 1 calc R . . O24 O 0.2696(4) 0.3226(3) 0.24952(15) 0.0364(7) Uani 1 1 d . . . H24A H 0.1653 0.3378 0.2423 0.055 Uiso 1 1 calc R . . C25 C 0.4672(9) 0.9253(6) 0.1218(3) 0.0812(19) Uani 1 1 d . . . H25A H 0.3547 0.9434 0.1341 0.122 Uiso 1 1 calc R . . H25B H 0.4832 0.9709 0.0847 0.122 Uiso 1 1 calc R . . H25C H 0.5558 0.9477 0.1548 0.122 Uiso 1 1 calc R . . O26 O 0.4787(6) 0.7993(3) 0.10946(17) 0.0734(12) Uani 1 1 d . . . H10A H 0.3937 0.7778 0.0856 0.110 Uiso 1 1 calc R . . H22B H 0.521(6) 0.676(4) 0.1716(19) 0.043(14) Uiso 1 1 d . . . H23B H 0.637(5) 0.288(4) 0.2366(17) 0.027(12) Uiso 1 1 d . . . H24B H 0.284(6) 0.258(4) 0.257(2) 0.044(15) 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 Zn1 0.0217(2) 0.0200(2) 0.0270(2) 0.00141(18) -0.00141(17) 0.00021(18) N1 0.033(2) 0.0257(17) 0.0274(17) 0.0025(13) 0.0021(14) 0.0042(14) C2 0.056(3) 0.024(2) 0.036(2) 0.0011(18) -0.009(2) 0.010(2) C3 0.074(4) 0.028(2) 0.039(2) -0.0045(19) -0.005(2) 0.015(2) C4 0.065(3) 0.035(2) 0.026(2) -0.0038(18) 0.001(2) 0.005(2) C5 0.030(2) 0.030(2) 0.028(2) 0.0035(17) 0.0004(17) 0.0003(17) C6 0.032(2) 0.0190(19) 0.030(2) 0.0016(15) 0.0029(17) 0.0043(15) N7 0.052(2) 0.0256(19) 0.0249(17) -0.0008(14) -0.0045(16) -0.0004(16) C8 0.039(3) 0.031(2) 0.025(2) -0.0014(17) 0.0018(18) 0.0005(18) O9 0.081(3) 0.0308(17) 0.0288(15) -0.0051(12) -0.0133(16) 0.0083(15) N10 0.059(3) 0.0210(18) 0.0251(17) -0.0027(13) -0.0081(16) 0.0006(16) C11 0.033(2) 0.026(2) 0.026(2) 0.0003(16) -0.0032(17) -0.0020(17) C12 0.036(2) 0.023(2) 0.029(2) -0.0050(16) -0.0044(18) -0.0045(17) N13 0.0314(19) 0.0225(17) 0.0300(17) -0.0005(13) -0.0034(14) -0.0027(14) C14 0.053(3) 0.022(2) 0.035(2) -0.0011(17) -0.004(2) 0.0030(19) C15 0.088(4) 0.028(2) 0.035(2) -0.0093(19) -0.006(2) -0.001(2) C16 0.068(3) 0.036(3) 0.025(2) -0.0053(18) -0.011(2) 0.003(2) O17 0.0194(14) 0.0209(13) 0.0453(16) -0.0050(11) -0.0003(12) -0.0006(11) S18 0.0188(5) 0.0181(5) 0.0358(5) -0.0044(4) -0.0021(4) 0.0005(4) O19 0.0195(15) 0.0208(14) 0.0559(18) -0.0072(12) 0.0020(13) 0.0013(11) O20 0.0246(16) 0.0311(16) 0.0556(18) -0.0130(13) 0.0073(14) 0.0028(12) O21 0.050(2) 0.0458(19) 0.0388(17) 0.0010(14) -0.0120(15) 0.0014(15) O22 0.0233(16) 0.0349(17) 0.0483(19) 0.0124(15) -0.0026(14) -0.0037(13) O23 0.0241(16) 0.0252(17) 0.065(2) 0.0136(15) 0.0092(15) 0.0019(12) O24 0.0255(16) 0.0205(16) 0.061(2) 0.0122(14) -0.0028(15) -0.0001(13) C25 0.090(5) 0.075(4) 0.079(4) 0.004(3) 0.009(4) -0.017(4) O26 0.102(3) 0.047(2) 0.062(2) 0.0073(18) -0.031(2) -0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O22 2.081(3) . ? Zn1 O24 2.093(3) . ? Zn1 O23 2.097(3) . ? Zn1 O17 2.146(2) . ? Zn1 N1 2.171(3) . ? Zn1 N13 2.176(3) 4_676 ? N1 C6 1.331(4) . ? N1 C2 1.333(5) . ? C2 C3 1.366(6) . ? C2 H2 0.9300 . ? C3 C4 1.375(5) . ? C3 H3 0.9300 . ? C4 C5 1.389(5) . ? C4 H4 0.9300 . ? C5 C6 1.388(5) . ? C5 N7 1.402(5) . ? C6 H6A 0.9300 . ? N7 C8 1.355(5) . ? N7 H7A 0.8600 . ? C8 O9 1.225(4) 1 ? C8 O9 1.225(4) . ? C8 N10 1.366(5) . ? N10 C11 1.406(5) . ? N10 H10 0.8600 . ? C11 C12 1.380(5) . ? C11 C16 1.392(5) . ? C12 N13 1.328(4) . ? C12 H12 0.9300 . ? N13 C14 1.342(5) . ? N13 Zn1 2.176(3) 4_575 ? C14 C15 1.366(6) . ? C14 H14 0.9300 . ? C15 C16 1.373(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? O17 S18 1.487(3) . ? S18 O21 1.455(3) . ? S18 O20 1.461(3) . ? S18 O19 1.477(3) . ? O22 H22A 0.8200 . ? O22 H22B 0.78(4) . ? O23 H23A 0.8200 . ? O23 H23B 0.80(4) . ? O24 H24A 0.8200 . ? O24 H24B 0.73(4) . ? C25 O26 1.403(6) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? O26 H10A 0.8200 . ? 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 O22 Zn1 O24 174.83(13) . . ? O22 Zn1 O23 94.38(12) . . ? O24 Zn1 O23 89.40(11) . . ? O22 Zn1 O17 88.26(11) . . ? O24 Zn1 O17 87.91(11) . . ? O23 Zn1 O17 177.16(11) . . ? O22 Zn1 N1 93.02(12) . . ? O24 Zn1 N1 90.58(12) . . ? O23 Zn1 N1 88.88(12) . . ? O17 Zn1 N1 92.04(11) . . ? O22 Zn1 N13 87.96(12) . 4_676 ? O24 Zn1 N13 88.76(12) . 4_676 ? O23 Zn1 N13 86.38(12) . 4_676 ? O17 Zn1 N13 92.66(11) . 4_676 ? N1 Zn1 N13 175.23(12) . 4_676 ? C6 N1 C2 118.6(3) . . ? C6 N1 Zn1 122.3(2) . . ? C2 N1 Zn1 119.0(2) . . ? N1 C2 C3 122.5(4) . . ? N1 C2 H2 118.7 . . ? C3 C2 H2 118.7 . . ? C2 C3 C4 119.3(4) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 119.1(4) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6 C5 C4 117.8(3) . . ? C6 C5 N7 125.1(3) . . ? C4 C5 N7 117.0(3) . . ? N1 C6 C5 122.6(3) . . ? N1 C6 H6A 118.7 . . ? C5 C6 H6A 118.7 . . ? C8 N7 C5 127.6(3) . . ? C8 N7 H7A 116.2 . . ? C5 N7 H7A 116.2 . . ? O9 C8 N7 123.4(4) 1 . ? O9 C8 N7 123.4(4) . . ? O9 C8 N10 123.4(4) 1 . ? O9 C8 N10 123.4(4) . . ? N7 C8 N10 113.2(3) . . ? C8 N10 C11 127.0(3) . . ? C8 N10 H10 116.5 . . ? C11 N10 H10 116.5 . . ? C12 C11 C16 117.6(4) . . ? C12 C11 N10 116.9(3) . . ? C16 C11 N10 125.5(3) . . ? N13 C12 C11 124.5(3) . . ? N13 C12 H12 117.8 . . ? C11 C12 H12 117.8 . . ? C12 N13 C14 117.3(3) . . ? C12 N13 Zn1 122.6(2) . 4_575 ? C14 N13 Zn1 119.8(2) . 4_575 ? N13 C14 C15 121.9(4) . . ? N13 C14 H14 119.0 . . ? C15 C14 H14 119.0 . . ? C14 C15 C16 120.8(4) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C11 117.9(4) . . ? C15 C16 H16 121.0 . . ? C11 C16 H16 121.0 . . ? S18 O17 Zn1 133.92(15) . . ? O21 S18 O20 110.41(18) . . ? O21 S18 O19 109.75(17) . . ? O20 S18 O19 109.34(16) . . ? O21 S18 O17 110.21(17) . . ? O20 S18 O17 108.42(15) . . ? O19 S18 O17 108.68(15) . . ? Zn1 O22 H22A 109.5 . . ? Zn1 O22 H22B 130(3) . . ? H22A O22 H22B 116.4 . . ? Zn1 O23 H23A 109.5 . . ? Zn1 O23 H23B 125(3) . . ? H23A O23 H23B 125.5 . . ? Zn1 O24 H24A 109.5 . . ? Zn1 O24 H24B 137(4) . . ? H24A O24 H24B 111.1 . . ? O26 C25 H25A 109.5 . . ? O26 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O26 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C25 O26 H10A 109.5 . . ? 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 N7 H7A O21 0.86 1.99 2.842(4) 168.7 3_565 N10 H10 O19 0.86 2.11 2.951(4) 165.9 3_565 O26 H10A O9 0.82 1.92 2.730(5) 168.6 1 O22 H22A O20 0.82 1.93 2.745(4) 175.8 1_655 O22 H22B O26 0.79(4) 1.89(4) 2.678(5) 175(5) 1 O23 H23A O19 0.82 1.98 2.738(4) 154.0 1_655 O23 H23B O20 0.80(4) 1.91(4) 2.703(4) 171(4) 2_545 O24 H24B O17 0.73(4) 2.02(4) 2.746(4) 177(5) 2_545 C12 H12 O19 0.93 2.56 3.356(4) 143.6 3_565 _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.927 _refine_diff_density_max 0.650 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.094