# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jianyong Zhang' _publ_contact_author_email zhjyong@mail.sysu.edu.cn loop_ _publ_author_name 'Xin Tan' 'Jixian Zhan' 'Jianyong Zhang' 'Mei Pan' 'Cheng-Yong Su' data_M-Cd _database_code_depnum_ccdc_archive 'CCDC 836380' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 Cd N O6' _chemical_formula_weight 389.63 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(5) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z+1/2' 'y, -x+y, z+1/6' 'x-y, x, z+5/6' _cell_length_a 10.5423(17) _cell_length_b 10.5423(17) _cell_length_c 20.448(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1968.1(6) _cell_formula_units_Z 6 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.972 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 1.692 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7854 _exptl_absorpt_correction_T_max 0.8490 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'multiwire proportional' _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 15029 _diffrn_reflns_av_R_equivalents 0.0543 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 27.44 _reflns_number_total 2984 _reflns_number_gt 2866 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0139P)^2^+0.3065P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(2) _refine_ls_number_reflns 2984 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0260 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.0516 _refine_ls_wR_factor_gt 0.0507 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.055 _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 O1W O 1.1850(3) 0.8119(3) 1.14839(12) 0.0367(5) Uani 1 1 d . . . H1WA H 1.1823 0.7407 1.1692 0.055 Uiso 1 1 d R . . H1WB H 1.1092 0.8179 1.1567 0.055 Uiso 1 1 d R . . O2W O 1.2736(3) 0.7570(3) 0.93356(12) 0.0457(6) Uani 1 1 d . . . H2WA H 1.2909 0.8280 0.9083 0.069 Uiso 1 1 d R . . H2WB H 1.3162 0.7120 0.9196 0.069 Uiso 1 1 d R . . Cd1 Cd 1.23842(2) 0.79340(2) 1.042554(17) 0.02545(7) Uani 1 1 d . . . C1 C 0.8757(3) 0.8246(3) 0.97663(14) 0.0239(6) Uani 1 1 d . . . C2 C 0.7475(3) 0.6988(3) 0.95926(14) 0.0249(6) Uani 1 1 d . . . H2A H 0.7375 0.6054 0.9672 0.030 Uiso 1 1 calc R . . C3 C 0.6336(3) 0.7086(3) 0.93032(14) 0.0240(6) Uani 1 1 d . . . C4 C 0.6479(3) 0.8456(3) 0.92084(13) 0.0232(6) Uani 1 1 d . . . H4A H 0.5689 0.8522 0.9021 0.028 Uiso 1 1 calc R . . C5 C 0.7758(3) 0.9739(3) 0.93823(13) 0.0214(6) Uani 1 1 d . . . C6 C 0.8902(3) 0.9609(3) 0.96649(14) 0.0239(6) Uani 1 1 d . . . H6A H 0.9783 1.0466 0.9788 0.029 Uiso 1 1 calc R . . C7 C 0.7890(3) 1.1197(3) 0.92481(13) 0.0236(6) Uani 1 1 d . . . C8 C 0.6638(3) 1.1287(3) 0.91420(14) 0.0269(6) Uani 1 1 d . . . H8A H 0.5716 1.0414 0.9176 0.032 Uiso 1 1 calc R . . C9 C 0.7940(4) 1.3765(3) 0.89643(15) 0.0317(7) Uani 1 1 d . . . H9A H 0.7967 1.4655 0.8858 0.038 Uiso 1 1 calc R . . C10 C 0.9238(4) 1.3791(4) 0.90838(17) 0.0391(8) Uani 1 1 d . . . H10A H 1.0141 1.4690 0.9074 0.047 Uiso 1 1 calc R . . C11 C 0.9212(4) 1.2493(4) 0.92185(16) 0.0338(7) Uani 1 1 d . . . H11A H 1.0102 1.2492 0.9291 0.041 Uiso 1 1 calc R . . C12 C 1.0005(3) 0.8093(3) 1.00423(14) 0.0257(6) Uani 1 1 d . . . C13 C 0.5006(3) 0.5734(3) 0.90486(14) 0.0263(6) Uani 1 1 d . . . O1 O 1.1239(3) 0.9225(3) 1.01006(11) 0.0367(5) Uani 1 1 d . . . O2 O 0.9789(2) 0.6849(2) 1.01955(10) 0.0331(5) Uani 1 1 d . . . O3 O 0.5197(3) 0.4704(2) 0.89119(13) 0.0451(6) Uani 1 1 d . . . O4 O 0.3847(2) 0.5771(2) 0.89629(11) 0.0365(5) Uani 1 1 d . . . N1 N 0.6648(3) 1.2534(3) 0.89937(12) 0.0269(5) 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 O1W 0.0328(13) 0.0428(15) 0.0400(13) 0.0076(10) 0.0059(10) 0.0231(12) O2W 0.0647(18) 0.0499(16) 0.0396(14) 0.0052(11) 0.0080(12) 0.0415(15) Cd1 0.01723(11) 0.02030(11) 0.03767(11) 0.00411(9) -0.00154(9) 0.00850(9) C1 0.0242(15) 0.0256(16) 0.0256(14) 0.0031(11) 0.0006(11) 0.0152(13) C2 0.0288(16) 0.0224(15) 0.0277(15) 0.0025(11) -0.0006(12) 0.0159(13) C3 0.0221(15) 0.0216(15) 0.0282(14) -0.0015(11) -0.0013(11) 0.0108(13) C4 0.0207(15) 0.0231(15) 0.0297(15) 0.0019(11) -0.0005(11) 0.0138(13) C5 0.0207(15) 0.0209(14) 0.0245(13) 0.0004(10) 0.0004(10) 0.0119(12) C6 0.0192(14) 0.0237(15) 0.0301(15) -0.0006(11) -0.0015(11) 0.0117(13) C7 0.0241(16) 0.0216(15) 0.0265(14) -0.0016(10) -0.0036(11) 0.0124(12) C8 0.0234(16) 0.0192(15) 0.0382(17) -0.0009(11) -0.0016(12) 0.0106(13) C9 0.0321(18) 0.0215(16) 0.0426(18) 0.0078(12) 0.0032(13) 0.0143(14) C10 0.0261(18) 0.0246(17) 0.061(2) 0.0056(15) 0.0031(15) 0.0083(14) C11 0.0232(16) 0.0329(18) 0.0468(19) 0.0038(13) -0.0012(13) 0.0152(15) C12 0.0237(16) 0.0309(17) 0.0268(15) 0.0026(12) -0.0022(11) 0.0169(14) C13 0.0275(16) 0.0190(15) 0.0305(14) 0.0001(11) -0.0031(12) 0.0103(13) O1 0.0245(12) 0.0298(13) 0.0548(14) 0.0117(10) -0.0006(10) 0.0127(11) O2 0.0250(12) 0.0290(13) 0.0492(14) 0.0057(9) -0.0032(9) 0.0165(10) O3 0.0424(14) 0.0228(12) 0.0708(18) -0.0073(11) -0.0093(12) 0.0168(11) O4 0.0278(12) 0.0329(13) 0.0491(14) -0.0129(9) -0.0123(9) 0.0155(11) N1 0.0255(14) 0.0219(13) 0.0359(13) 0.0023(10) -0.0016(10) 0.0137(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 O1W Cd1 2.269(2) . ? O1W H1WA 0.8503 . ? O1W H1WB 0.8499 . ? O2W Cd1 2.322(3) . ? O2W H2WA 0.8504 . ? O2W H2WB 0.8498 . ? Cd1 O3 2.185(2) 5_665 ? Cd1 N1 2.293(3) 5 ? Cd1 O1 2.322(2) . ? Cd1 O2 2.426(2) . ? Cd1 C12 2.712(3) . ? C1 C6 1.383(4) . ? C1 C2 1.385(4) . ? C1 C12 1.513(4) . ? C2 C3 1.389(4) . ? C2 H2A 0.9500 . ? C3 C4 1.389(4) . ? C3 C13 1.507(4) . ? C4 C5 1.397(4) . ? C4 H4A 0.9500 . ? C5 C6 1.405(4) . ? C5 C7 1.497(4) . ? C6 H6A 0.9500 . ? C7 C11 1.382(4) . ? C7 C8 1.388(4) . ? C8 N1 1.344(4) . ? C8 H8A 0.9500 . ? C9 N1 1.332(4) . ? C9 C10 1.377(5) . ? C9 H9A 0.9500 . ? C10 C11 1.382(5) . ? C10 H10A 0.9500 . ? C11 H11A 0.9500 . ? C12 O2 1.253(4) . ? C12 O1 1.256(4) . ? C13 O3 1.231(4) . ? C13 O4 1.255(4) . ? O3 Cd1 2.185(2) 6_544 ? N1 Cd1 2.293(3) 6_554 ? 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 Cd1 O1W H1WA 107.5 . . ? Cd1 O1W H1WB 118.7 . . ? H1WA O1W H1WB 110.4 . . ? Cd1 O2W H2WA 114.8 . . ? Cd1 O2W H2WB 126.0 . . ? H2WA O2W H2WB 110.2 . . ? O3 Cd1 O1W 91.72(9) 5_665 . ? O3 Cd1 N1 96.11(9) 5_665 5 ? O1W Cd1 N1 91.04(9) . 5 ? O3 Cd1 O1 107.99(9) 5_665 . ? O1W Cd1 O1 89.92(8) . . ? N1 Cd1 O1 155.84(9) 5 . ? O3 Cd1 O2W 92.99(10) 5_665 . ? O1W Cd1 O2W 175.15(9) . . ? N1 Cd1 O2W 87.34(9) 5 . ? O1 Cd1 O2W 89.71(9) . . ? O3 Cd1 O2 162.96(8) 5_665 . ? O1W Cd1 O2 87.45(8) . . ? N1 Cd1 O2 100.92(8) 5 . ? O1 Cd1 O2 55.01(8) . . ? O2W Cd1 O2 88.37(8) . . ? O3 Cd1 C12 135.51(9) 5_665 . ? O1W Cd1 C12 89.62(9) . . ? N1 Cd1 C12 128.33(9) 5 . ? O1 Cd1 C12 27.53(9) . . ? O2W Cd1 C12 87.81(10) . . ? O2 Cd1 C12 27.53(8) . . ? C6 C1 C2 120.3(3) . . ? C6 C1 C12 121.1(3) . . ? C2 C1 C12 118.6(3) . . ? C1 C2 C3 120.3(3) . . ? C1 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? C2 C3 C4 119.3(3) . . ? C2 C3 C13 120.4(3) . . ? C4 C3 C13 120.1(2) . . ? C3 C4 C5 121.5(3) . . ? C3 C4 H4A 119.3 . . ? C5 C4 H4A 119.3 . . ? C4 C5 C6 118.1(3) . . ? C4 C5 C7 119.8(2) . . ? C6 C5 C7 122.1(3) . . ? C1 C6 C5 120.6(3) . . ? C1 C6 H6A 119.7 . . ? C5 C6 H6A 119.7 . . ? C11 C7 C8 116.7(3) . . ? C11 C7 C5 123.6(3) . . ? C8 C7 C5 119.7(3) . . ? N1 C8 C7 124.0(3) . . ? N1 C8 H8A 118.0 . . ? C7 C8 H8A 118.0 . . ? N1 C9 C10 122.2(3) . . ? N1 C9 H9A 118.9 . . ? C10 C9 H9A 118.9 . . ? C9 C10 C11 119.2(3) . . ? C9 C10 H10A 120.4 . . ? C11 C10 H10A 120.4 . . ? C7 C11 C10 119.9(3) . . ? C7 C11 H11A 120.0 . . ? C10 C11 H11A 120.0 . . ? O2 C12 O1 122.0(3) . . ? O2 C12 C1 119.4(3) . . ? O1 C12 C1 118.5(3) . . ? O2 C12 Cd1 63.47(15) . . ? O1 C12 Cd1 58.72(15) . . ? C1 C12 Cd1 174.4(2) . . ? O3 C13 O4 126.0(3) . . ? O3 C13 C3 115.4(3) . . ? O4 C13 C3 118.6(3) . . ? C12 O1 Cd1 93.75(18) . . ? C12 O2 Cd1 89.01(18) . . ? C13 O3 Cd1 153.3(2) . 6_544 ? C9 N1 C8 117.9(3) . . ? C9 N1 Cd1 124.3(2) . 6_554 ? C8 N1 Cd1 117.8(2) . 6_554 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.3(4) . . . . ? C12 C1 C2 C3 -176.3(3) . . . . ? C1 C2 C3 C4 -2.0(4) . . . . ? C1 C2 C3 C13 173.5(3) . . . . ? C2 C3 C4 C5 1.7(4) . . . . ? C13 C3 C4 C5 -173.8(3) . . . . ? C3 C4 C5 C6 -0.7(4) . . . . ? C3 C4 C5 C7 177.6(3) . . . . ? C2 C1 C6 C5 -0.3(4) . . . . ? C12 C1 C6 C5 177.3(3) . . . . ? C4 C5 C6 C1 0.0(4) . . . . ? C7 C5 C6 C1 -178.3(3) . . . . ? C4 C5 C7 C11 -160.1(3) . . . . ? C6 C5 C7 C11 18.1(4) . . . . ? C4 C5 C7 C8 19.5(4) . . . . ? C6 C5 C7 C8 -162.2(3) . . . . ? C11 C7 C8 N1 2.3(4) . . . . ? C5 C7 C8 N1 -177.4(3) . . . . ? N1 C9 C10 C11 2.1(5) . . . . ? C8 C7 C11 C10 -0.4(4) . . . . ? C5 C7 C11 C10 179.2(3) . . . . ? C9 C10 C11 C7 -1.6(5) . . . . ? C6 C1 C12 O2 172.2(3) . . . . ? C2 C1 C12 O2 -10.2(4) . . . . ? C6 C1 C12 O1 -8.9(4) . . . . ? C2 C1 C12 O1 168.7(3) . . . . ? O3 Cd1 C12 O2 -177.27(16) 5_665 . . . ? O1W Cd1 C12 O2 -85.21(17) . . . . ? N1 Cd1 C12 O2 5.8(2) 5 . . . ? O1 Cd1 C12 O2 -175.8(3) . . . . ? O2W Cd1 C12 O2 90.68(17) . . . . ? O3 Cd1 C12 O1 -1.5(2) 5_665 . . . ? O1W Cd1 C12 O1 90.54(18) . . . . ? N1 Cd1 C12 O1 -178.43(17) 5 . . . ? O2W Cd1 C12 O1 -93.57(18) . . . . ? O2 Cd1 C12 O1 175.8(3) . . . . ? C2 C3 C13 O3 -23.4(4) . . . . ? C4 C3 C13 O3 152.0(3) . . . . ? C2 C3 C13 O4 160.1(3) . . . . ? C4 C3 C13 O4 -24.5(4) . . . . ? O2 C12 O1 Cd1 4.5(3) . . . . ? C1 C12 O1 Cd1 -174.4(2) . . . . ? O3 Cd1 O1 C12 178.88(18) 5_665 . . . ? O1W Cd1 O1 C12 -89.34(18) . . . . ? N1 Cd1 O1 C12 3.0(3) 5 . . . ? O2W Cd1 O1 C12 85.83(18) . . . . ? O2 Cd1 O1 C12 -2.40(16) . . . . ? O1 C12 O2 Cd1 -4.3(3) . . . . ? C1 C12 O2 Cd1 174.5(2) . . . . ? O3 Cd1 O2 C12 6.5(4) 5_665 . . . ? O1W Cd1 O2 C12 94.08(17) . . . . ? N1 Cd1 O2 C12 -175.36(17) 5 . . . ? O1 Cd1 O2 C12 2.40(16) . . . . ? O2W Cd1 O2 C12 -88.38(17) . . . . ? O4 C13 O3 Cd1 -28.1(7) . . . 6_544 ? C3 C13 O3 Cd1 155.8(4) . . . 6_544 ? C10 C9 N1 C8 -0.4(5) . . . . ? C10 C9 N1 Cd1 -177.3(2) . . . 6_554 ? C7 C8 N1 C9 -1.9(4) . . . . ? C7 C8 N1 Cd1 175.2(2) . . . 6_554 ? 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 O1W H1WA O4 0.85 1.85 2.687(3) 167.2 3_665 O1W H1WB O1 0.85 1.92 2.762(3) 170.9 5_565 O2W H2WA O2 0.85 1.94 2.781(3) 169.8 6_654 O2W H2WB O4 0.85 1.95 2.788(3) 169.1 1_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.318 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.067 #=======================================# data_P-Cd _database_code_depnum_ccdc_archive 'CCDC 836381' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H11 Cd N O6' _chemical_formula_sum 'C13 H11 Cd N O6' _chemical_formula_weight 389.63 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(1) _symmetry_space_group_name_Hall P61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' 'y, -x+y, z+5/6' 'x-y, x, z+1/6' _cell_length_a 10.5544(2) _cell_length_b 10.5544(2) _cell_length_c 20.4446(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1972.31(8) _cell_formula_units_Z 6 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1206 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 28.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.968 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 1.689 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7288 _exptl_absorpt_correction_T_max 0.8493 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7819 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.41 _reflns_number_total 2933 _reflns_number_gt 2759 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0136P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.026(16) _refine_ls_number_reflns 2933 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0207 _refine_ls_R_factor_gt 0.0177 _refine_ls_wR_factor_ref 0.0346 _refine_ls_wR_factor_gt 0.0337 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 Cd1 Cd 1.445024(17) 0.206589(16) 1.031443(12) 0.02589(5) Uani 1 1 d . . . O2W O 1.5172(2) 0.2437(2) 0.92256(9) 0.0476(5) Uani 1 1 d . . . H2WA H 1.6066 0.2822 0.9116 0.071 Uiso 1 1 d R . . H2WB H 1.4634 0.1838 0.8932 0.071 Uiso 1 1 d R . . O1W O 1.3727(2) 0.1881(2) 1.13757(9) 0.0372(4) Uani 1 1 d . . . H1WA H 1.2908 0.1834 1.1439 0.056 Uiso 1 1 d R . . H1WB H 1.4367 0.2508 1.1632 0.056 Uiso 1 1 d R . . O3 O 0.80774(19) 0.42305(18) 0.88528(8) 0.0369(4) Uani 1 1 d . . . O4 O 1.04931(19) 0.52953(18) 0.87967(10) 0.0471(5) Uani 1 1 d . . . N1 N 0.4117(2) -0.2534(2) 0.88828(9) 0.0276(4) Uani 1 1 d . . . C1 C 1.0514(2) 0.1758(2) 0.96575(10) 0.0239(5) Uani 1 1 d . . . C2 C 1.0491(2) 0.3015(2) 0.94784(10) 0.0260(5) Uani 1 1 d . . . H2 H 1.1310 0.3929 0.9550 0.031 Uiso 1 1 calc R . . C3 C 0.9247(2) 0.2912(2) 0.91924(10) 0.0234(4) Uani 1 1 d . . . C4 C 0.8020(2) 0.1541(2) 0.90974(10) 0.0249(5) Uani 1 1 d . . . H4 H 0.7182 0.1475 0.8914 0.030 Uiso 1 1 calc R . . C5 C 0.8021(2) 0.0258(2) 0.92730(10) 0.0225(4) Uani 1 1 d . . . C6 C 0.9288(2) 0.0390(2) 0.95505(10) 0.0239(5) Uani 1 1 d . . . H6 H 0.9314 -0.0449 0.9666 0.029 Uiso 1 1 calc R . . C7 C 0.6694(2) -0.1191(2) 0.91359(10) 0.0245(5) Uani 1 1 d . . . C12 C 1.1907(3) 0.1902(3) 0.99337(11) 0.0259(5) Uani 1 1 d . . . C8 C 0.5346(2) -0.1289(2) 0.90301(10) 0.0277(5) Uani 1 1 d . . . H8 H 0.5295 -0.0438 0.9064 0.033 Uiso 1 1 calc R . . C9 C 0.4177(3) -0.3769(3) 0.88516(11) 0.0329(5) Uani 1 1 d . . . H9 H 0.3333 -0.4639 0.8746 0.039 Uiso 1 1 calc R . . C10 C 0.5459(3) -0.3795(3) 0.89711(13) 0.0399(6) Uani 1 1 d . . . H10 H 0.5466 -0.4672 0.8962 0.048 Uiso 1 1 calc R . . O1 O 1.29443(17) 0.31556(18) 1.00820(7) 0.0327(4) Uani 1 1 d . . . O2 O 1.20130(18) 0.07762(19) 0.99896(8) 0.0364(4) Uani 1 1 d . . . C11 C 0.6720(3) -0.2497(3) 0.91029(11) 0.0336(5) Uani 1 1 d . . . H11 H 0.7594 -0.2492 0.9170 0.040 Uiso 1 1 calc R . . C13 C 0.9267(2) 0.4263(2) 0.89369(10) 0.0268(5) 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 Cd1 0.02091(8) 0.02055(8) 0.03837(8) -0.00432(8) -0.00581(7) 0.01199(7) O2W 0.0308(11) 0.0569(13) 0.0400(10) -0.0078(9) 0.0002(8) 0.0106(9) O1W 0.0301(10) 0.0420(11) 0.0411(9) -0.0093(8) -0.0019(8) 0.0191(9) O3 0.0314(9) 0.0319(9) 0.0491(10) 0.0110(7) -0.0001(8) 0.0170(8) O4 0.0307(10) 0.0221(9) 0.0789(14) 0.0088(9) -0.0020(10) 0.0061(8) N1 0.0200(9) 0.0244(10) 0.0353(9) -0.0017(8) -0.0031(8) 0.0088(8) C1 0.0215(11) 0.0267(12) 0.0245(10) -0.0017(9) -0.0016(9) 0.0128(10) C2 0.0214(11) 0.0242(12) 0.0279(11) -0.0042(9) -0.0029(10) 0.0081(10) C3 0.0218(11) 0.0224(11) 0.0247(10) -0.0008(9) -0.0007(9) 0.0102(9) C4 0.0192(11) 0.0245(12) 0.0303(11) 0.0001(9) -0.0024(9) 0.0103(9) C5 0.0208(11) 0.0216(11) 0.0239(9) -0.0010(9) -0.0003(8) 0.0098(9) C6 0.0220(11) 0.0213(11) 0.0289(10) 0.0014(9) 0.0013(9) 0.0112(9) C7 0.0213(11) 0.0231(11) 0.0275(11) 0.0004(9) -0.0008(9) 0.0099(10) C12 0.0187(11) 0.0332(13) 0.0275(11) -0.0052(10) -0.0045(9) 0.0143(11) C8 0.0237(11) 0.0211(12) 0.0383(12) -0.0017(10) -0.0022(10) 0.0112(10) C9 0.0261(12) 0.0269(13) 0.0410(13) -0.0048(10) -0.0029(10) 0.0097(11) C10 0.0371(15) 0.0239(13) 0.0608(16) -0.0071(12) -0.0051(13) 0.0170(12) O1 0.0221(8) 0.0291(9) 0.0474(10) -0.0058(7) -0.0093(7) 0.0131(8) O2 0.0268(9) 0.0291(9) 0.0565(10) -0.0103(8) -0.0140(8) 0.0162(8) C11 0.0268(13) 0.0318(14) 0.0464(14) -0.0035(11) -0.0044(11) 0.0177(11) C13 0.0261(12) 0.0192(11) 0.0307(11) -0.0015(9) -0.0032(10) 0.0080(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 Cd1 O4 2.1864(17) 6_645 ? Cd1 O1W 2.2759(18) . ? Cd1 N1 2.2989(19) 6_655 ? Cd1 O2W 2.3218(19) . ? Cd1 O2 2.3259(16) . ? Cd1 O1 2.4296(16) . ? Cd1 C12 2.716(2) . ? O2W H2WA 0.8500 . ? O2W H2WB 0.8502 . ? O1W H1WA 0.8500 . ? O1W H1WB 0.8502 . ? O3 C13 1.251(3) . ? O4 C13 1.238(3) . ? O4 Cd1 2.1864(17) 5_674 ? N1 C9 1.338(3) . ? N1 C8 1.340(3) . ? N1 Cd1 2.2989(19) 5_564 ? C1 C2 1.388(3) . ? C1 C6 1.392(3) . ? C1 C12 1.510(3) . ? C2 C3 1.391(3) . ? C2 H2 0.9300 . ? C3 C4 1.391(3) . ? C3 C13 1.509(3) . ? C4 C5 1.402(3) . ? C4 H4 0.9300 . ? C5 C6 1.394(3) . ? C5 C7 1.496(3) . ? C6 H6 0.9300 . ? C7 C8 1.390(3) . ? C7 C11 1.395(3) . ? C12 O2 1.253(3) . ? C12 O1 1.262(3) . ? C8 H8 0.9300 . ? C9 C10 1.388(4) . ? C9 H9 0.9300 . ? C10 C11 1.377(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cd1 O1W 92.01(7) 6_645 . ? O4 Cd1 N1 96.18(7) 6_645 6_655 ? O1W Cd1 N1 91.10(7) . 6_655 ? O4 Cd1 O2W 92.80(8) 6_645 . ? O1W Cd1 O2W 175.02(7) . . ? N1 Cd1 O2W 87.12(7) 6_655 . ? O4 Cd1 O2 107.98(6) 6_645 . ? O1W Cd1 O2 89.80(6) . . ? N1 Cd1 O2 155.77(6) 6_655 . ? O2W Cd1 O2 89.92(7) . . ? O4 Cd1 O1 163.03(6) 6_645 . ? O1W Cd1 O1 87.49(6) . . ? N1 Cd1 O1 100.79(6) 6_655 . ? O2W Cd1 O1 88.28(6) . . ? O2 Cd1 O1 55.06(6) . . ? O4 Cd1 C12 135.39(7) 6_645 . ? O1W Cd1 C12 89.38(7) . . ? N1 Cd1 C12 128.38(7) 6_655 . ? O2W Cd1 C12 88.08(7) . . ? O2 Cd1 C12 27.41(7) . . ? O1 Cd1 C12 27.68(6) . . ? Cd1 O2W H2WA 121.7 . . ? Cd1 O2W H2WB 120.7 . . ? H2WA O2W H2WB 109.8 . . ? Cd1 O1W H1WA 116.0 . . ? Cd1 O1W H1WB 114.8 . . ? H1WA O1W H1WB 109.9 . . ? C13 O4 Cd1 153.10(17) . 5_674 ? C9 N1 C8 118.1(2) . . ? C9 N1 Cd1 124.19(15) . 5_564 ? C8 N1 Cd1 117.60(15) . 5_564 ? C2 C1 C6 119.9(2) . . ? C2 C1 C12 118.9(2) . . ? C6 C1 C12 121.1(2) . . ? C1 C2 C3 120.2(2) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C4 119.5(2) . . ? C2 C3 C13 120.3(2) . . ? C4 C3 C13 120.00(19) . . ? C3 C4 C5 121.2(2) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 118.2(2) . . ? C6 C5 C7 122.6(2) . . ? C4 C5 C7 119.14(19) . . ? C1 C6 C5 121.0(2) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C8 C7 C11 116.3(2) . . ? C8 C7 C5 120.4(2) . . ? C11 C7 C5 123.3(2) . . ? O2 C12 O1 122.0(2) . . ? O2 C12 C1 118.9(2) . . ? O1 C12 C1 119.1(2) . . ? O2 C12 Cd1 58.68(11) . . ? O1 C12 Cd1 63.42(11) . . ? C1 C12 Cd1 174.34(15) . . ? N1 C8 C7 124.2(2) . . ? N1 C8 H8 117.9 . . ? C7 C8 H8 117.9 . . ? N1 C9 C10 122.1(2) . . ? N1 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C11 C10 C9 118.8(2) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C12 O1 Cd1 88.90(13) . . ? C12 O2 Cd1 93.90(14) . . ? C10 C11 C7 120.3(2) . . ? C10 C11 H11 119.8 . . ? C7 C11 H11 119.8 . . ? O4 C13 O3 125.8(2) . . ? O4 C13 C3 115.2(2) . . ? O3 C13 C3 118.8(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 O1W H1WA O2 0.85 1.92 2.761(2) 170.9 6_545 O1W H1WB O3 0.85 1.84 2.688(2) 179.0 2_755 O2W H2WA O3 0.85 1.96 2.786(3) 163.0 1_655 O2W H2WB O1 0.85 1.95 2.792(3) 167.8 5_664 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.275 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.054 #=======================================# data_M-Zn _database_code_depnum_ccdc_archive 'CCDC 836382' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 N O6 Zn' _chemical_formula_weight 342.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(5) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z+1/2' 'y, -x+y, z+1/6' 'x-y, x, z+5/6' _cell_length_a 10.2531(2) _cell_length_b 10.2531(2) _cell_length_c 20.2456(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1843.20(7) _cell_formula_units_Z 6 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2260 _cell_measurement_theta_min 4.3641 _cell_measurement_theta_max 63.0065 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.852 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1044 _exptl_absorpt_coefficient_mu 3.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5778 _exptl_absorpt_correction_T_max 0.7481 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'multiwire proportional' _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 3178 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.98 _diffrn_reflns_theta_max 63.10 _reflns_number_total 1313 _reflns_number_gt 1292 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0394P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 1313 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0240 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0597 _refine_ls_wR_factor_gt 0.0595 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.075 _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 0.79297(5) 1.23642(5) 0.07936(2) 0.01693(14) Uani 1 1 d . . . O4 O 0.5593(3) 0.3671(3) 0.22496(12) 0.0220(5) Uani 1 1 d . . . N1 N 1.2503(3) 0.6500(3) 0.22342(14) 0.0172(6) Uani 1 1 d . . . C8 C 0.8147(4) 0.8729(4) 0.14426(16) 0.0163(7) Uani 1 1 d . . . C9 C 0.6842(4) 0.7401(4) 0.16220(16) 0.0177(7) Uani 1 1 d . . . H9 H 0.5880 0.7288 0.1538 0.021 Uiso 1 1 calc R . . C2 C 1.3848(4) 0.9185(4) 0.2159(2) 0.0245(8) Uani 1 1 d . . . H2 H 1.4783 1.0102 0.2172 0.029 Uiso 1 1 calc R . . C4 C 1.1172(4) 0.7826(4) 0.19783(16) 0.0172(7) Uani 1 1 d . . . C5 C 1.1237(4) 0.6514(4) 0.20773(17) 0.0200(7) Uani 1 1 d . . . H5 H 1.0333 0.5575 0.2031 0.024 Uiso 1 1 calc R . . C1 C 1.3787(4) 0.7836(4) 0.22765(17) 0.0212(8) Uani 1 1 d . . . H1 H 1.4689 0.7846 0.2393 0.025 Uiso 1 1 calc R . . C3 C 1.2513(4) 0.9190(4) 0.20195(18) 0.0227(8) Uani 1 1 d . . . H3 H 1.2524 1.0113 0.1954 0.027 Uiso 1 1 calc R . . C6 C 0.9685(4) 0.7706(4) 0.18408(16) 0.0165(7) Uani 1 1 d . . . C7 C 0.9560(4) 0.8889(4) 0.15559(17) 0.0163(7) Uani 1 1 d . . . H7 H 1.0443 0.9802 0.1440 0.020 Uiso 1 1 calc R . . C10 C 0.6960(4) 0.6247(4) 0.19237(16) 0.0159(7) Uani 1 1 d . . . O3 O 0.4549(3) 0.5110(3) 0.23640(13) 0.0254(6) Uani 1 1 d . . . O1 O 0.9118(3) 1.1301(3) 0.11357(12) 0.0213(5) Uani 1 1 d . . . O1W O 0.8213(3) 1.1878(3) -0.01736(13) 0.0224(5) Uani 1 1 d . . . H1WA H 0.8211 1.1060 -0.0246 0.034 Uiso 1 1 d R . . H1WB H 0.7728 1.2017 -0.0479 0.034 Uiso 1 1 d R . . O2 O 0.6706(3) 0.9753(3) 0.09821(12) 0.0204(5) Uani 1 1 d . . . O2W O 0.7461(3) 1.2588(3) 0.18062(12) 0.0233(6) Uani 1 1 d . . . H2WA H 0.8215 1.2828 0.2055 0.035 Uiso 1 1 d R . . H2WB H 0.7028 1.3079 0.1916 0.035 Uiso 1 1 d R . . C12 C 0.7975(4) 0.9992(4) 0.11633(16) 0.0174(7) Uani 1 1 d . . . C13 C 0.5582(4) 0.4888(4) 0.21892(17) 0.0174(7) Uani 1 1 d . . . C11 C 0.8370(4) 0.6403(4) 0.20211(17) 0.0167(7) Uani 1 1 d . . . H11 H 0.8440 0.5597 0.2216 0.020 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 0.0141(2) 0.0131(2) 0.0229(2) 0.00064(18) -0.00170(19) 0.00634(19) O4 0.0210(12) 0.0200(13) 0.0267(13) 0.0050(10) 0.0060(10) 0.0116(11) N1 0.0166(14) 0.0137(15) 0.0214(14) -0.0011(12) -0.0005(12) 0.0076(12) C8 0.0186(18) 0.0147(16) 0.0152(15) -0.0019(13) -0.0020(14) 0.0079(15) C9 0.0186(17) 0.0193(17) 0.0188(17) -0.0022(14) -0.0009(14) 0.0122(14) C2 0.0191(18) 0.0194(18) 0.033(2) -0.0019(16) 0.0004(16) 0.0081(15) C4 0.0172(17) 0.0181(17) 0.0155(16) -0.0010(13) 0.0008(13) 0.0081(14) C5 0.0142(17) 0.0213(18) 0.0242(18) -0.0016(15) 0.0004(14) 0.0087(15) C1 0.0172(17) 0.0248(19) 0.0228(18) -0.0006(15) -0.0019(15) 0.0114(15) C3 0.0231(19) 0.0193(18) 0.027(2) -0.0022(15) -0.0018(15) 0.0111(16) C6 0.0181(17) 0.0171(17) 0.0166(15) -0.0037(13) -0.0010(13) 0.0106(15) C7 0.0156(16) 0.0154(16) 0.0165(16) 0.0007(13) 0.0020(13) 0.0067(15) C10 0.0179(17) 0.0145(16) 0.0161(15) -0.0017(13) 0.0004(14) 0.0087(14) O3 0.0128(11) 0.0244(13) 0.0388(15) 0.0041(12) 0.0028(11) 0.0093(10) O1 0.0217(13) 0.0154(13) 0.0268(13) -0.0001(10) -0.0044(11) 0.0092(11) O1W 0.0234(13) 0.0216(13) 0.0248(12) -0.0027(10) -0.0028(11) 0.0132(11) O2 0.0191(13) 0.0186(12) 0.0266(13) 0.0006(10) -0.0036(10) 0.0117(11) O2W 0.0235(13) 0.0283(14) 0.0233(14) -0.0030(10) -0.0036(10) 0.0169(11) C12 0.0230(18) 0.0152(19) 0.0150(16) -0.0008(13) -0.0011(15) 0.0104(16) C13 0.0138(16) 0.0190(18) 0.0196(18) 0.0010(14) -0.0003(14) 0.0084(14) C11 0.0178(18) 0.0163(17) 0.0195(16) -0.0014(13) -0.0010(14) 0.0112(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 O3 1.996(2) 6_664 ? Zn1 O1W 2.077(3) . ? Zn1 N1 2.100(3) 6_554 ? Zn1 O1 2.117(2) . ? Zn1 O2W 2.144(2) . ? Zn1 O2 2.351(2) . ? Zn1 C12 2.567(3) . ? O4 C13 1.260(4) . ? N1 C5 1.344(4) . ? N1 C1 1.346(5) . ? N1 Zn1 2.100(3) 5 ? C8 C7 1.393(5) . ? C8 C9 1.398(5) . ? C8 C12 1.503(5) . ? C9 C10 1.389(5) . ? C9 H9 0.9500 . ? C2 C1 1.374(5) . ? C2 C3 1.400(5) . ? C2 H2 0.9500 . ? C4 C3 1.389(5) . ? C4 C5 1.394(5) . ? C4 C6 1.494(5) . ? C5 H5 0.9500 . ? C1 H1 0.9500 . ? C3 H3 0.9500 . ? C6 C11 1.391(5) . ? C6 C7 1.406(5) . ? C7 H7 0.9500 . ? C10 C11 1.387(5) . ? C10 C13 1.503(5) . ? O3 C13 1.241(4) . ? O3 Zn1 1.996(2) 5_455 ? O1 C12 1.267(4) . ? O1W H1WA 0.8503 . ? O1W H1WB 0.8496 . ? O2 C12 1.252(4) . ? O2W H2WA 0.8500 . ? O2W H2WB 0.8502 . ? C11 H11 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 O1W 93.12(10) 6_664 . ? O3 Zn1 N1 97.49(11) 6_664 6_554 ? O1W Zn1 N1 93.44(10) . 6_554 ? O3 Zn1 O1 106.67(10) 6_664 . ? O1W Zn1 O1 89.95(10) . . ? N1 Zn1 O1 155.38(10) 6_554 . ? O3 Zn1 O2W 93.60(10) 6_664 . ? O1W Zn1 O2W 173.27(10) . . ? N1 Zn1 O2W 86.12(11) 6_554 . ? O1 Zn1 O2W 87.70(10) . . ? O3 Zn1 O2 165.14(9) 6_664 . ? O1W Zn1 O2 86.48(9) . . ? N1 Zn1 O2 97.36(10) 6_554 . ? O1 Zn1 O2 58.49(9) . . ? O2W Zn1 O2 86.92(9) . . ? O3 Zn1 C12 136.10(11) 6_664 . ? O1W Zn1 C12 88.65(10) . . ? N1 Zn1 C12 126.21(11) 6_554 . ? O1 Zn1 C12 29.43(10) . . ? O2W Zn1 C12 86.21(11) . . ? O2 Zn1 C12 29.08(10) . . ? C5 N1 C1 117.5(3) . . ? C5 N1 Zn1 118.9(2) . 5 ? C1 N1 Zn1 123.4(2) . 5 ? C7 C8 C9 120.3(3) . . ? C7 C8 C12 121.6(3) . . ? C9 C8 C12 118.0(3) . . ? C10 C9 C8 119.7(3) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C1 C2 C3 119.1(3) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C3 C4 C5 117.5(3) . . ? C3 C4 C6 123.4(3) . . ? C5 C4 C6 119.1(3) . . ? N1 C5 C4 123.8(3) . . ? N1 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? N1 C1 C2 122.9(3) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C4 C3 C2 119.1(3) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C11 C6 C7 118.3(3) . . ? C11 C6 C4 119.3(3) . . ? C7 C6 C4 122.4(3) . . ? C8 C7 C6 120.3(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C11 C10 C9 119.6(3) . . ? C11 C10 C13 119.9(3) . . ? C9 C10 C13 120.4(3) . . ? C13 O3 Zn1 151.3(2) . 5_455 ? C12 O1 Zn1 95.4(2) . . ? Zn1 O1W H1WA 117.9 . . ? Zn1 O1W H1WB 118.8 . . ? H1WA O1W H1WB 109.1 . . ? C12 O2 Zn1 85.1(2) . . ? Zn1 O2W H2WA 112.2 . . ? Zn1 O2W H2WB 121.6 . . ? H2WA O2W H2WB 110.0 . . ? O2 C12 O1 121.0(3) . . ? O2 C12 C8 120.0(3) . . ? O1 C12 C8 119.0(3) . . ? O2 C12 Zn1 65.86(18) . . ? O1 C12 Zn1 55.19(17) . . ? C8 C12 Zn1 172.8(2) . . ? O3 C13 O4 125.8(3) . . ? O3 C13 C10 115.2(3) . . ? O4 C13 C10 118.9(3) . . ? C10 C11 C6 121.8(3) . . ? C10 C11 H11 119.1 . . ? C6 C11 H11 119.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 C8 C9 C10 1.0(5) . . . . ? C12 C8 C9 C10 -175.6(3) . . . . ? C1 N1 C5 C4 -2.2(5) . . . . ? Zn1 N1 C5 C4 173.9(3) 5 . . . ? C3 C4 C5 N1 2.7(5) . . . . ? C6 C4 C5 N1 -176.8(3) . . . . ? C5 N1 C1 C2 -0.8(5) . . . . ? Zn1 N1 C1 C2 -176.7(3) 5 . . . ? C3 C2 C1 N1 3.2(6) . . . . ? C5 C4 C3 C2 -0.2(5) . . . . ? C6 C4 C3 C2 179.2(3) . . . . ? C1 C2 C3 C4 -2.6(6) . . . . ? C3 C4 C6 C11 -158.6(3) . . . . ? C5 C4 C6 C11 20.8(5) . . . . ? C3 C4 C6 C7 19.0(5) . . . . ? C5 C4 C6 C7 -161.6(3) . . . . ? C9 C8 C7 C6 1.1(5) . . . . ? C12 C8 C7 C6 177.6(3) . . . . ? C11 C6 C7 C8 -1.8(5) . . . . ? C4 C6 C7 C8 -179.4(3) . . . . ? C8 C9 C10 C11 -2.4(5) . . . . ? C8 C9 C10 C13 173.0(3) . . . . ? O3 Zn1 O1 C12 179.4(2) 6_664 . . . ? O1W Zn1 O1 C12 -87.3(2) . . . . ? N1 Zn1 O1 C12 10.8(4) 6_554 . . . ? O2W Zn1 O1 C12 86.4(2) . . . . ? O2 Zn1 O1 C12 -1.43(18) . . . . ? O3 Zn1 O2 C12 4.7(5) 6_664 . . . ? O1W Zn1 O2 C12 93.6(2) . . . . ? N1 Zn1 O2 C12 -173.4(2) 6_554 . . . ? O1 Zn1 O2 C12 1.45(18) . . . . ? O2W Zn1 O2 C12 -87.74(19) . . . . ? Zn1 O2 C12 O1 -2.4(3) . . . . ? Zn1 O2 C12 C8 175.2(3) . . . . ? Zn1 O1 C12 O2 2.7(3) . . . . ? Zn1 O1 C12 C8 -175.0(3) . . . . ? C7 C8 C12 O2 170.1(3) . . . . ? C9 C8 C12 O2 -13.3(5) . . . . ? C7 C8 C12 O1 -12.2(5) . . . . ? C9 C8 C12 O1 164.4(3) . . . . ? O3 Zn1 C12 O2 -178.28(17) 6_664 . . . ? O1W Zn1 C12 O2 -85.19(19) . . . . ? N1 Zn1 C12 O2 8.1(2) 6_554 . . . ? O1 Zn1 C12 O2 -177.5(3) . . . . ? O2W Zn1 C12 O2 90.47(19) . . . . ? O3 Zn1 C12 O1 -0.8(3) 6_664 . . . ? O1W Zn1 C12 O1 92.3(2) . . . . ? N1 Zn1 C12 O1 -174.43(19) 6_554 . . . ? O2W Zn1 C12 O1 -92.0(2) . . . . ? O2 Zn1 C12 O1 177.5(3) . . . . ? Zn1 O3 C13 O4 -39.2(7) 5_455 . . . ? Zn1 O3 C13 C10 144.8(4) 5_455 . . . ? C11 C10 C13 O3 147.6(3) . . . . ? C9 C10 C13 O3 -27.8(5) . . . . ? C11 C10 C13 O4 -28.6(5) . . . . ? C9 C10 C13 O4 155.9(3) . . . . ? C9 C10 C11 C6 1.8(5) . . . . ? C13 C10 C11 C6 -173.7(3) . . . . ? C7 C6 C11 C10 0.3(5) . . . . ? C4 C6 C11 C10 178.0(3) . . . . ? 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 O1W H1WA O1 0.85 1.91 2.747(3) 166.9 6_654 O1W H1WB O4 0.85 1.85 2.686(3) 167.5 2_664 O2W H2WA O2 0.85 1.90 2.747(3) 171.3 5_565 O2W H2WB O4 0.85 1.97 2.798(3) 164.3 1_565 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 63.10 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.314 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.054 #=======================================# data_P-Zn _database_code_depnum_ccdc_archive 'CCDC 836383' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 N O6 Zn' _chemical_formula_weight 342.60 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 Hexagonal _symmetry_space_group_name_H-M P6(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' 'y, -x+y, z+5/6' 'x-y, x, z+1/6' _cell_length_a 10.2723(4) _cell_length_b 10.2723(4) _cell_length_c 20.4692(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1870.54(13) _cell_formula_units_Z 6 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.825 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1044 _exptl_absorpt_coefficient_mu 1.999 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6906 _exptl_absorpt_correction_T_max 0.6906 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5821 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0550 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2703 _reflns_number_gt 2499 _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^)+(0.0070P)^2^+0.3368P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.013(12) _refine_ls_number_reflns 2703 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0635 _refine_ls_wR_factor_gt 0.0539 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _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 O1W O 0.2541(3) 1.5146(3) 0.10676(10) 0.0360(6) Uani 1 1 d . . . H1WA H 0.1862 1.4613 0.1343 0.054 Uiso 1 1 d R . . H1WB H 0.2925 1.6072 0.1163 0.054 Uiso 1 1 d R . . O2W O 0.1813(2) 1.3666(3) -0.08996(11) 0.0311(5) Uani 1 1 d . . . H2WA H 0.1807 1.2850 -0.0977 0.047 Uiso 1 1 d R . . H2WB H 0.2386 1.4344 -0.1168 0.047 Uiso 1 1 d R . . Zn1 Zn 0.20876(4) 1.44379(4) 0.005906(17) 0.02324(9) Uani 1 1 d . . . C1 C 0.1878(3) 1.0598(3) 0.07148(13) 0.0204(6) Uani 1 1 d . . . C2 C 0.0465(3) 0.9337(3) 0.08276(14) 0.0227(6) Uani 1 1 d . . . H2 H -0.0416 0.9363 0.0709 0.027 Uiso 1 1 calc R . . C3 C 0.0333(3) 0.8036(3) 0.11138(13) 0.0204(6) Uani 1 1 d . . . C4 C 0.1646(3) 0.8047(3) 0.12945(14) 0.0225(6) Uani 1 1 d . . . H4 H 0.1578 0.7176 0.1490 0.027 Uiso 1 1 calc R . . C5 C 0.3061(3) 0.9311(3) 0.11952(13) 0.0231(6) Uani 1 1 d . . . C6 C 0.3166(3) 1.0572(3) 0.08992(13) 0.0224(6) Uani 1 1 d . . . H6 H 0.4127 1.1426 0.0822 0.027 Uiso 1 1 calc R . . C7 C -0.1145(3) 0.6671(3) 0.12544(13) 0.0207(6) Uani 1 1 d . . . C8 C -0.2485(4) 0.6697(4) 0.12952(15) 0.0300(7) Uani 1 1 d . . . H8 H -0.2495 0.7606 0.1225 0.036 Uiso 1 1 calc R . . C9 C -0.3811(4) 0.5374(4) 0.14405(17) 0.0359(8) Uani 1 1 d . . . H9A H -0.4737 0.5369 0.1464 0.043 Uiso 1 1 calc R . . C10 C -0.3767(3) 0.4066(4) 0.15509(14) 0.0287(7) Uani 1 1 d . . . H10 H -0.4672 0.3176 0.1663 0.034 Uiso 1 1 calc R . . C11 C -0.1218(3) 0.5299(3) 0.13480(14) 0.0261(6) Uani 1 1 d . . . H11A H -0.0317 0.5262 0.1298 0.031 Uiso 1 1 calc R . . C12 C 0.2031(4) 1.2015(3) 0.04308(14) 0.0253(7) Uani 1 1 d . . . C13 C 0.4439(3) 0.9316(3) 0.14581(13) 0.0222(6) Uani 1 1 d . . . N1 N -0.2485(3) 0.4011(3) 0.15057(11) 0.0244(5) Uani 1 1 d . . . O1 O 0.0907(3) 1.2198(2) 0.04019(11) 0.0314(5) Uani 1 1 d . . . O2 O 0.3310(2) 1.3051(2) 0.02529(10) 0.0304(5) Uani 1 1 d . . . O3 O 0.5484(2) 1.0586(2) 0.16264(11) 0.0364(5) Uani 1 1 d . . . O4 O 0.4417(2) 0.8097(2) 0.15247(10) 0.0314(5) 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 O1W 0.0395(14) 0.0246(12) 0.0355(12) 0.0004(10) 0.0039(10) 0.0097(11) O2W 0.0308(12) 0.0255(12) 0.0346(11) 0.0021(10) 0.0049(10) 0.0122(10) Zn1 0.01855(18) 0.01967(18) 0.03323(15) 0.00491(14) 0.00327(15) 0.01084(15) C1 0.0220(15) 0.0181(14) 0.0222(12) 0.0023(11) 0.0018(11) 0.0109(13) C2 0.0188(15) 0.0242(16) 0.0269(13) -0.0014(12) -0.0012(12) 0.0122(13) C3 0.0206(15) 0.0162(14) 0.0246(12) 0.0005(11) -0.0002(11) 0.0093(12) C4 0.0186(15) 0.0193(14) 0.0271(13) 0.0018(12) 0.0008(12) 0.0075(12) C5 0.0244(16) 0.0239(15) 0.0221(12) -0.0026(12) -0.0018(12) 0.0129(13) C6 0.0198(14) 0.0140(13) 0.0263(13) 0.0008(12) 0.0021(12) 0.0031(12) C7 0.0170(14) 0.0152(14) 0.0268(13) 0.0000(12) 0.0000(11) 0.0058(12) C8 0.0248(17) 0.0196(15) 0.0443(18) 0.0037(14) 0.0023(14) 0.0102(13) C9 0.0223(16) 0.0333(19) 0.0527(19) 0.0053(16) 0.0086(15) 0.0144(15) C10 0.0224(15) 0.0259(16) 0.0341(16) 0.0034(14) 0.0050(13) 0.0094(14) C11 0.0197(15) 0.0257(16) 0.0329(15) -0.0009(13) -0.0003(12) 0.0113(13) C12 0.0384(19) 0.0171(15) 0.0218(13) -0.0002(12) 0.0019(13) 0.0149(15) C13 0.0174(14) 0.0230(15) 0.0259(13) 0.0024(12) 0.0013(12) 0.0098(13) N1 0.0201(13) 0.0189(12) 0.0321(12) 0.0018(10) 0.0024(10) 0.0082(11) O1 0.0308(12) 0.0274(12) 0.0429(11) 0.0106(10) 0.0062(10) 0.0197(11) O2 0.0298(12) 0.0224(12) 0.0372(11) 0.0077(9) 0.0063(9) 0.0116(10) O3 0.0163(10) 0.0236(11) 0.0592(14) -0.0001(11) -0.0053(10) 0.0023(9) O4 0.0273(12) 0.0253(12) 0.0439(12) -0.0004(10) -0.0093(10) 0.0150(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 O1W Zn1 2.161(2) . ? O1W H1WA 0.8497 . ? O1W H1WB 0.8501 . ? O2W Zn1 2.082(2) . ? O2W H2WA 0.8502 . ? O2W H2WB 0.8499 . ? Zn1 O3 1.985(2) 5_464 ? Zn1 N1 2.097(3) 5_564 ? Zn1 O1 2.114(2) . ? Zn1 O2 2.356(2) . ? Zn1 C12 2.576(3) . ? C1 C6 1.389(4) . ? C1 C2 1.399(4) . ? C1 C12 1.501(4) . ? C2 C3 1.402(4) . ? C2 H2 0.9500 . ? C3 C4 1.394(4) . ? C3 C7 1.491(4) . ? C4 C5 1.397(4) . ? C4 H4 0.9500 . ? C5 C6 1.384(4) . ? C5 C13 1.512(4) . ? C6 H6 0.9500 . ? C7 C11 1.387(4) . ? C7 C8 1.393(4) . ? C8 C9 1.392(4) . ? C8 H8 0.9500 . ? C9 C10 1.385(5) . ? C9 H9A 0.9500 . ? C10 N1 1.349(4) . ? C10 H10 0.9500 . ? C11 N1 1.352(4) . ? C11 H11A 0.9500 . ? C12 O1 1.261(4) . ? C12 O2 1.263(4) . ? C13 O4 1.248(4) . ? C13 O3 1.254(3) . ? N1 Zn1 2.097(3) 6_655 ? O3 Zn1 1.985(2) 6_765 ? 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 Zn1 O1W H1WA 116.6 . . ? Zn1 O1W H1WB 119.8 . . ? H1WA O1W H1WB 109.9 . . ? Zn1 O2W H2WA 118.9 . . ? Zn1 O2W H2WB 112.9 . . ? H2WA O2W H2WB 110.4 . . ? O3 Zn1 O2W 93.09(9) 5_464 . ? O3 Zn1 N1 97.67(9) 5_464 5_564 ? O2W Zn1 N1 93.52(9) . 5_564 ? O3 Zn1 O1 106.68(9) 5_464 . ? O2W Zn1 O1 90.21(9) . . ? N1 Zn1 O1 155.13(9) 5_564 . ? O3 Zn1 O1W 93.19(10) 5_464 . ? O2W Zn1 O1W 173.71(9) . . ? N1 Zn1 O1W 85.98(9) 5_564 . ? O1 Zn1 O1W 87.66(9) . . ? O3 Zn1 O2 165.00(9) 5_464 . ? O2W Zn1 O2 86.57(8) . . ? N1 Zn1 O2 97.32(9) 5_564 . ? O1 Zn1 O2 58.34(8) . . ? O1W Zn1 O2 87.27(8) . . ? O3 Zn1 C12 135.79(10) 5_464 . ? O2W Zn1 C12 88.69(9) . . ? N1 Zn1 C12 126.32(10) 5_564 . ? O1 Zn1 C12 29.12(9) . . ? O1W Zn1 C12 86.57(9) . . ? O2 Zn1 C12 29.23(9) . . ? C6 C1 C2 119.7(3) . . ? C6 C1 C12 119.0(3) . . ? C2 C1 C12 121.3(3) . . ? C1 C2 C3 120.8(3) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 118.1(3) . . ? C4 C3 C7 118.8(3) . . ? C2 C3 C7 123.0(3) . . ? C3 C4 C5 121.4(3) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C6 C5 C4 119.4(3) . . ? C6 C5 C13 121.1(3) . . ? C4 C5 C13 119.2(3) . . ? C5 C6 C1 120.5(3) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? C11 C7 C8 117.3(3) . . ? C11 C7 C3 119.6(3) . . ? C8 C7 C3 123.0(3) . . ? C9 C8 C7 119.2(3) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C10 C9 C8 119.4(3) . . ? C10 C9 H9A 120.3 . . ? C8 C9 H9A 120.3 . . ? N1 C10 C9 122.4(3) . . ? N1 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? N1 C11 C7 124.3(3) . . ? N1 C11 H11A 117.8 . . ? C7 C11 H11A 117.8 . . ? O1 C12 O2 120.4(3) . . ? O1 C12 C1 120.2(3) . . ? O2 C12 C1 119.3(3) . . ? O1 C12 Zn1 54.67(15) . . ? O2 C12 Zn1 65.72(16) . . ? C1 C12 Zn1 173.0(2) . . ? O4 C13 O3 126.2(3) . . ? O4 C13 C5 119.2(3) . . ? O3 C13 C5 114.5(3) . . ? C10 N1 C11 117.2(3) . . ? C10 N1 Zn1 123.4(2) . 6_655 ? C11 N1 Zn1 119.2(2) . 6_655 ? C12 O1 Zn1 96.21(19) . . ? C12 O2 Zn1 85.05(18) . . ? C13 O3 Zn1 151.7(2) . 6_765 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.2(4) . . . . ? C12 C1 C2 C3 -177.8(3) . . . . ? C1 C2 C3 C4 1.3(4) . . . . ? C1 C2 C3 C7 179.0(3) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? C7 C3 C4 C5 -177.9(3) . . . . ? C3 C4 C5 C6 -1.3(4) . . . . ? C3 C4 C5 C13 174.2(3) . . . . ? C4 C5 C6 C1 1.4(4) . . . . ? C13 C5 C6 C1 -174.0(3) . . . . ? C2 C1 C6 C5 -0.2(4) . . . . ? C12 C1 C6 C5 176.5(3) . . . . ? C4 C3 C7 C11 -21.8(4) . . . . ? C2 C3 C7 C11 160.5(3) . . . . ? C4 C3 C7 C8 158.5(3) . . . . ? C2 C3 C7 C8 -19.2(4) . . . . ? C11 C7 C8 C9 1.5(4) . . . . ? C3 C7 C8 C9 -178.8(3) . . . . ? C7 C8 C9 C10 0.9(5) . . . . ? C8 C9 C10 N1 -1.8(5) . . . . ? C8 C7 C11 N1 -3.3(4) . . . . ? C3 C7 C11 N1 177.0(3) . . . . ? C6 C1 C12 O1 -163.3(3) . . . . ? C2 C1 C12 O1 13.3(4) . . . . ? C6 C1 C12 O2 13.0(4) . . . . ? C2 C1 C12 O2 -170.3(3) . . . . ? O3 Zn1 C12 O1 0.3(2) 5_464 . . . ? O2W Zn1 C12 O1 -92.78(18) . . . . ? N1 Zn1 C12 O1 173.82(16) 5_564 . . . ? O1W Zn1 C12 O1 91.36(18) . . . . ? O2 Zn1 C12 O1 -178.1(3) . . . . ? O3 Zn1 C12 O2 178.40(15) 5_464 . . . ? O2W Zn1 C12 O2 85.31(16) . . . . ? N1 Zn1 C12 O2 -8.1(2) 5_564 . . . ? O1 Zn1 C12 O2 178.1(3) . . . . ? O1W Zn1 C12 O2 -90.55(16) . . . . ? C6 C5 C13 O4 -157.0(3) . . . . ? C4 C5 C13 O4 27.6(4) . . . . ? C6 C5 C13 O3 27.1(4) . . . . ? C4 C5 C13 O3 -148.3(3) . . . . ? C9 C10 N1 C11 0.2(4) . . . . ? C9 C10 N1 Zn1 176.1(2) . . . 6_655 ? C7 C11 N1 C10 2.4(4) . . . . ? C7 C11 N1 Zn1 -173.6(2) . . . 6_655 ? O2 C12 O1 Zn1 -2.0(3) . . . . ? C1 C12 O1 Zn1 174.3(2) . . . . ? O3 Zn1 O1 C12 -179.78(17) 5_464 . . . ? O2W Zn1 O1 C12 86.94(18) . . . . ? N1 Zn1 O1 C12 -11.9(3) 5_564 . . . ? O1W Zn1 O1 C12 -87.14(18) . . . . ? O2 Zn1 O1 C12 1.10(16) . . . . ? O1 C12 O2 Zn1 1.8(3) . . . . ? C1 C12 O2 Zn1 -174.6(2) . . . . ? O3 Zn1 O2 C12 -4.3(4) 5_464 . . . ? O2W Zn1 O2 C12 -93.45(17) . . . . ? N1 Zn1 O2 C12 173.43(17) 5_564 . . . ? O1 Zn1 O2 C12 -1.09(16) . . . . ? O1W Zn1 O2 C12 87.84(17) . . . . ? O4 C13 O3 Zn1 38.3(6) . . . 6_765 ? C5 C13 O3 Zn1 -146.1(4) . . . 6_765 ? 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 O1W H1WA O2 0.85 1.92 2.770(3) 176.1 6_665 O1W H1WB O4 0.85 2.01 2.817(3) 158.4 1_565 O2W H2WA O1 0.85 1.93 2.763(3) 167.0 5_454 O2W H2WB O4 0.85 1.85 2.691(3) 170.8 3_574 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.343 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.078 #=========================END