# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_e _database_code_depnum_ccdc_archive 'CCDC 917727' #TrackingRef 'polymer 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H9 Co N3 O6' _chemical_formula_weight 338.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 10.510(4) _cell_length_b 8.418(3) _cell_length_c 14.039(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.052(5) _cell_angle_gamma 90.00 _cell_volume 1232.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1498 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 26.53 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.822 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 1.426 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7538 _exptl_absorpt_correction_T_max 0.8145 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8935 _diffrn_reflns_av_R_equivalents 0.0643 _diffrn_reflns_av_sigmaI/netI 0.0597 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 25.49 _reflns_number_total 2291 _reflns_number_gt 1770 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.8298P] 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 2291 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1079 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.005 _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 Co1 Co 0.80418(5) 1.02330(6) 0.25579(4) 0.01888(18) Uani 1 1 d . . . O1 O 0.8586(3) 1.2221(3) 0.18707(18) 0.0218(6) Uani 1 1 d . . . O2 O 0.9177(3) 1.3069(4) 0.0495(2) 0.0383(8) Uani 1 1 d . . . O3 O 0.8442(3) 0.8897(4) -0.2234(2) 0.0383(8) Uani 1 1 d . . . O4 O 0.7366(3) 0.6740(3) -0.1862(2) 0.0286(7) Uani 1 1 d . . . O5 O 0.9462(3) 0.8927(3) 0.19476(19) 0.0266(7) Uani 1 1 d . . . H1W H 1.0201 0.9244 0.2185 0.040 Uiso 1 1 d R . . H2W H 0.9549 0.7956 0.2108 0.040 Uiso 1 1 d R . . O6 O 0.9423(3) 1.0624(4) 0.37383(19) 0.0314(7) Uani 1 1 d . . . H3W H 0.9117 1.1228 0.4139 0.047 Uiso 1 1 d R . . H4W H 0.9947 0.9865 0.3876 0.047 Uiso 1 1 d R . . N1 N 0.7051(3) 1.0015(4) 0.0972(2) 0.0185(7) Uani 1 1 d . . . N2 N 0.6563(3) 0.8237(4) -0.0342(2) 0.0222(8) Uani 1 1 d . . . N3 N 0.3351(3) 0.6570(4) 0.1806(2) 0.0204(7) Uani 1 1 d . . . C1 C 0.7895(4) 1.0746(4) 0.0471(3) 0.0171(8) Uani 1 1 d . . . C2 C 0.8117(4) 1.0251(5) -0.0428(3) 0.0223(9) Uani 1 1 d . . . H2 H 0.8679 1.0794 -0.0775 0.027 Uiso 1 1 calc R . . C3 C 0.7468(4) 0.8910(5) -0.0793(3) 0.0182(8) Uani 1 1 d . . . C4 C 0.6360(4) 0.8831(5) 0.0509(3) 0.0196(8) Uani 1 1 d . . . C5 C 0.8615(4) 1.2129(5) 0.0981(3) 0.0202(9) Uani 1 1 d . . . C6 C 0.7786(4) 0.8136(5) -0.1723(3) 0.0224(9) Uani 1 1 d . . . C7 C 0.3709(4) 0.6080(5) 0.0966(3) 0.0312(11) Uani 1 1 d . . . H7 H 0.3291 0.5207 0.0665 0.037 Uiso 1 1 calc R . . C8 C 0.4661(4) 0.6801(5) 0.0528(3) 0.0296(10) Uani 1 1 d . . . H8 H 0.4878 0.6415 -0.0052 0.036 Uiso 1 1 calc R . . C9 C 0.5295(4) 0.8114(5) 0.0964(3) 0.0206(9) Uani 1 1 d . . . C10 C 0.4891(4) 0.8670(5) 0.1804(3) 0.0242(9) Uani 1 1 d . . . H10 H 0.5265 0.9572 0.2102 0.029 Uiso 1 1 calc R . . C11 C 0.3933(4) 0.7880(5) 0.2196(3) 0.0256(9) Uani 1 1 d . . . H11 H 0.3674 0.8273 0.2761 0.031 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 Co1 0.0229(3) 0.0180(3) 0.0168(3) 0.0021(2) 0.0068(2) 0.0028(2) O1 0.0296(16) 0.0209(15) 0.0149(14) -0.0005(11) 0.0032(11) -0.0056(12) O2 0.061(2) 0.038(2) 0.0164(15) 0.0005(13) 0.0063(14) -0.0305(17) O3 0.056(2) 0.0300(18) 0.0346(18) -0.0078(14) 0.0285(16) -0.0161(16) O4 0.0336(17) 0.0248(17) 0.0303(16) -0.0106(13) 0.0157(13) -0.0090(13) O5 0.0267(16) 0.0281(17) 0.0259(15) 0.0009(13) 0.0065(12) 0.0067(13) O6 0.0380(17) 0.0369(19) 0.0187(15) -0.0046(13) 0.0005(13) 0.0168(14) N1 0.0239(17) 0.0148(18) 0.0172(16) 0.0013(13) 0.0039(13) -0.0022(14) N2 0.0277(19) 0.0208(19) 0.0198(17) -0.0042(14) 0.0103(14) -0.0058(15) N3 0.0227(18) 0.0175(18) 0.0220(17) -0.0036(14) 0.0067(14) -0.0029(14) C1 0.0200(19) 0.014(2) 0.0167(19) 0.0018(15) 0.0000(15) -0.0042(16) C2 0.027(2) 0.023(2) 0.018(2) 0.0027(17) 0.0054(16) -0.0043(18) C3 0.021(2) 0.017(2) 0.017(2) -0.0002(16) 0.0057(15) 0.0002(16) C4 0.025(2) 0.017(2) 0.019(2) -0.0029(16) 0.0063(16) -0.0016(17) C5 0.024(2) 0.018(2) 0.018(2) -0.0012(16) 0.0024(16) -0.0039(17) C6 0.023(2) 0.023(2) 0.022(2) -0.0070(17) 0.0042(17) -0.0014(18) C7 0.039(3) 0.029(3) 0.028(2) -0.012(2) 0.013(2) -0.012(2) C8 0.038(3) 0.028(3) 0.027(2) -0.0085(19) 0.0173(19) -0.009(2) C9 0.019(2) 0.018(2) 0.024(2) 0.0008(17) 0.0033(16) -0.0034(17) C10 0.025(2) 0.026(2) 0.023(2) -0.0056(18) 0.0065(17) -0.0056(18) C11 0.029(2) 0.027(2) 0.022(2) -0.0053(18) 0.0090(18) -0.0013(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O4 2.017(3) 4_576 ? Co1 O1 2.048(3) . ? Co1 O6 2.091(3) . ? Co1 O5 2.118(3) . ? Co1 N3 2.128(3) 2_655 ? Co1 N1 2.347(3) . ? O1 C5 1.256(4) . ? O2 C5 1.241(5) . ? O3 C6 1.233(5) . ? O4 C6 1.262(5) . ? O4 Co1 2.017(3) 4_575 ? O5 H1W 0.8500 . ? O5 H2W 0.8501 . ? O6 H3W 0.8500 . ? O6 H4W 0.8500 . ? N1 C1 1.347(5) . ? N1 C4 1.351(5) . ? N2 C3 1.332(5) . ? N2 C4 1.337(5) . ? N3 C11 1.344(5) . ? N3 C7 1.346(5) . ? N3 Co1 2.128(3) 2_645 ? C1 C2 1.376(5) . ? C1 C5 1.518(5) . ? C2 C3 1.385(5) . ? C2 H2 0.9300 . ? C3 C6 1.532(5) . ? C4 C9 1.484(5) . ? C7 C8 1.378(6) . ? C7 H7 0.9300 . ? C8 C9 1.393(6) . ? C8 H8 0.9300 . ? C9 C10 1.384(5) . ? C10 C11 1.377(5) . ? 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 Co1 O1 174.65(11) 4_576 . ? O4 Co1 O6 93.12(12) 4_576 . ? O1 Co1 O6 92.17(11) . . ? O4 Co1 O5 92.09(11) 4_576 . ? O1 Co1 O5 88.99(11) . . ? O6 Co1 O5 86.97(11) . . ? O4 Co1 N3 88.37(12) 4_576 2_655 ? O1 Co1 N3 90.67(12) . 2_655 ? O6 Co1 N3 91.75(12) . 2_655 ? O5 Co1 N3 178.66(12) . 2_655 ? O4 Co1 N1 100.45(11) 4_576 . ? O1 Co1 N1 74.57(10) . . ? O6 Co1 N1 161.53(11) . . ? O5 Co1 N1 80.11(11) . . ? N3 Co1 N1 101.04(12) 2_655 . ? C5 O1 Co1 117.4(2) . . ? C6 O4 Co1 134.0(3) . 4_575 ? Co1 O5 H1W 109.5 . . ? Co1 O5 H2W 116.8 . . ? H1W O5 H2W 97.7 . . ? Co1 O6 H3W 109.7 . . ? Co1 O6 H4W 115.4 . . ? H3W O6 H4W 125.8 . . ? C1 N1 C4 115.8(3) . . ? C1 N1 Co1 102.4(2) . . ? C4 N1 Co1 131.6(2) . . ? C3 N2 C4 117.8(3) . . ? C11 N3 C7 116.5(3) . . ? C11 N3 Co1 124.4(3) . 2_645 ? C7 N3 Co1 119.1(3) . 2_645 ? N1 C1 C2 122.5(3) . . ? N1 C1 C5 115.3(3) . . ? C2 C1 C5 122.2(3) . . ? C1 C2 C3 117.1(4) . . ? C1 C2 H2 121.5 . . ? C3 C2 H2 121.5 . . ? N2 C3 C2 121.3(3) . . ? N2 C3 C6 117.8(3) . . ? C2 C3 C6 120.9(3) . . ? N2 C4 N1 124.8(3) . . ? N2 C4 C9 116.3(3) . . ? N1 C4 C9 118.8(3) . . ? O2 C5 O1 125.4(4) . . ? O2 C5 C1 118.3(3) . . ? O1 C5 C1 116.4(3) . . ? O3 C6 O4 127.1(4) . . ? O3 C6 C3 118.1(4) . . ? O4 C6 C3 114.8(3) . . ? N3 C7 C8 123.5(4) . . ? N3 C7 H7 118.2 . . ? C8 C7 H7 118.2 . . ? C7 C8 C9 119.2(4) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C8 117.6(4) . . ? C10 C9 C4 123.7(3) . . ? C8 C9 C4 118.7(3) . . ? C11 C10 C9 119.6(4) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? N3 C11 C10 123.5(4) . . ? N3 C11 H11 118.3 . . ? C10 C11 H11 118.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Co1 O1 C5 -48.5(13) 4_576 . . . ? O6 Co1 O1 C5 140.2(3) . . . . ? O5 Co1 O1 C5 53.3(3) . . . . ? N3 Co1 O1 C5 -128.0(3) 2_655 . . . ? N1 Co1 O1 C5 -26.8(3) . . . . ? O4 Co1 N1 C1 -150.4(2) 4_576 . . . ? O1 Co1 N1 C1 31.6(2) . . . . ? O6 Co1 N1 C1 -13.8(5) . . . . ? O5 Co1 N1 C1 -60.1(2) . . . . ? N3 Co1 N1 C1 119.2(2) 2_655 . . . ? O4 Co1 N1 C4 -8.1(4) 4_576 . . . ? O1 Co1 N1 C4 173.9(4) . . . . ? O6 Co1 N1 C4 128.5(4) . . . . ? O5 Co1 N1 C4 82.2(3) . . . . ? N3 Co1 N1 C4 -98.5(3) 2_655 . . . ? C4 N1 C1 C2 -4.7(5) . . . . ? Co1 N1 C1 C2 144.8(3) . . . . ? C4 N1 C1 C5 177.0(3) . . . . ? Co1 N1 C1 C5 -33.6(4) . . . . ? N1 C1 C2 C3 -2.6(6) . . . . ? C5 C1 C2 C3 175.7(3) . . . . ? C4 N2 C3 C2 -4.5(6) . . . . ? C4 N2 C3 C6 174.5(3) . . . . ? C1 C2 C3 N2 7.4(6) . . . . ? C1 C2 C3 C6 -171.6(4) . . . . ? C3 N2 C4 N1 -3.6(6) . . . . ? C3 N2 C4 C9 176.6(3) . . . . ? C1 N1 C4 N2 8.1(6) . . . . ? Co1 N1 C4 N2 -130.4(4) . . . . ? C1 N1 C4 C9 -172.1(3) . . . . ? Co1 N1 C4 C9 49.4(5) . . . . ? Co1 O1 C5 O2 -163.2(3) . . . . ? Co1 O1 C5 C1 16.9(4) . . . . ? N1 C1 C5 O2 -163.8(4) . . . . ? C2 C1 C5 O2 17.8(6) . . . . ? N1 C1 C5 O1 16.1(5) . . . . ? C2 C1 C5 O1 -162.3(4) . . . . ? Co1 O4 C6 O3 33.8(7) 4_575 . . . ? Co1 O4 C6 C3 -143.9(3) 4_575 . . . ? N2 C3 C6 O3 167.0(4) . . . . ? C2 C3 C6 O3 -14.0(6) . . . . ? N2 C3 C6 O4 -15.1(5) . . . . ? C2 C3 C6 O4 163.9(4) . . . . ? C11 N3 C7 C8 3.1(6) . . . . ? Co1 N3 C7 C8 -175.6(4) 2_645 . . . ? N3 C7 C8 C9 -0.3(7) . . . . ? C7 C8 C9 C10 -2.7(6) . . . . ? C7 C8 C9 C4 177.1(4) . . . . ? N2 C4 C9 C10 -174.7(4) . . . . ? N1 C4 C9 C10 5.5(6) . . . . ? N2 C4 C9 C8 5.6(6) . . . . ? N1 C4 C9 C8 -174.2(4) . . . . ? C8 C9 C10 C11 2.8(6) . . . . ? C4 C9 C10 C11 -177.0(4) . . . . ? C7 N3 C11 C10 -3.0(6) . . . . ? Co1 N3 C11 C10 175.7(3) 2_645 . . . ? C9 C10 C11 N3 0.1(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H4W O2 0.85 1.93 2.750(4) 162.5 2_745 O6 H3W O2 0.85 1.99 2.741(4) 147.4 4_586 O5 H2W O6 0.85 2.60 3.210(4) 130.0 2_745 O5 H2W O1 0.85 2.36 2.862(4) 117.8 2_745 O5 H2W O3 0.85 2.21 2.902(4) 138.0 4_576 O5 H2W O1 0.85 2.36 2.862(4) 117.8 2_745 O5 H1W O3 0.85 2.11 2.856(4) 145.7 3_775 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.685 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.091 data_20101131a _database_code_depnum_ccdc_archive 'CCDC 917728' #TrackingRef 'polymer 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H9 N3 Ni O6' _chemical_formula_weight 337.92 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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 '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' _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 10.4369(3) _cell_length_b 8.4152(2) _cell_length_c 13.9080(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.836(3) _cell_angle_gamma 90.00 _cell_volume 1212.83(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3089 _cell_measurement_theta_min 3.1976 _cell_measurement_theta_max 66.9631 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.851 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 2.671 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6450 _exptl_absorpt_correction_T_max 0.6746 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _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 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4448 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.27 _diffrn_reflns_theta_max 67.08 _reflns_number_total 2157 _reflns_number_gt 1987 _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^)+(0.0547P)^2^+1.0831P] 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 2157 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0989 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 Ni1 Ni 0.80341(4) -0.02271(5) 0.75360(3) 0.01709(16) Uani 1 1 d . . . O1 O 0.86239(16) -0.2209(2) 0.68931(12) 0.0198(4) Uani 1 1 d . . . O2 O 0.9192(2) -0.3065(3) 0.54941(14) 0.0383(6) Uani 1 1 d . . . O3 O 0.8442(2) 0.1120(3) 0.27596(16) 0.0388(5) Uani 1 1 d . . . O4 O 0.73658(19) 0.3271(2) 0.31500(14) 0.0278(4) Uani 1 1 d . . . O5 O 0.94509(17) 0.1047(2) 0.69497(13) 0.0252(4) Uani 1 1 d . . . H5A H 0.9357 0.2035 0.7047 0.038 Uiso 1 1 d R . . H5B H 1.0183 0.0693 0.7187 0.038 Uiso 1 1 d R . . O6 O 0.93867(19) -0.0604(2) 0.87194(13) 0.0297(4) Uani 1 1 d . . . H6A H 0.9192 -0.1156 0.9193 0.045 Uiso 1 1 d R . . H6B H 0.9845 0.0193 0.8916 0.045 Uiso 1 1 d R . . N1 N 0.7060(2) -0.0008(2) 0.59997(14) 0.0166(4) Uani 1 1 d . . . N2 N 0.6551(2) 0.1751(2) 0.46692(15) 0.0208(4) Uani 1 1 d . . . N3 N 0.33392(19) 0.3457(2) 0.68376(15) 0.0188(4) Uani 1 1 d . . . C1 C 0.8639(2) -0.2133(3) 0.59918(17) 0.0192(5) Uani 1 1 d . . . C2 C 0.7896(2) -0.0751(3) 0.54840(17) 0.0165(5) Uani 1 1 d . . . C3 C 0.8106(2) -0.0266(3) 0.45730(18) 0.0189(5) Uani 1 1 d . . . H3 H 0.8660 -0.0819 0.4216 0.023 Uiso 1 1 calc R . . C4 C 0.7457(2) 0.1082(3) 0.42089(17) 0.0184(5) Uani 1 1 d . . . C5 C 0.7784(2) 0.1876(3) 0.32775(18) 0.0204(5) Uani 1 1 d . . . C6 C 0.6363(2) 0.1164(3) 0.55322(18) 0.0173(5) Uani 1 1 d . . . C7 C 0.3912(2) 0.2152(3) 0.72388(18) 0.0230(5) Uani 1 1 d . . . H7 H 0.3643 0.1766 0.7809 0.028 Uiso 1 1 calc R . . C8 C 0.4882(2) 0.1354(3) 0.68473(18) 0.0226(5) Uani 1 1 d . . . H8 H 0.5257 0.0456 0.7153 0.027 Uiso 1 1 calc R . . C9 C 0.5292(2) 0.1901(3) 0.59950(18) 0.0185(5) Uani 1 1 d . . . C10 C 0.4640(3) 0.3204(3) 0.55488(19) 0.0260(6) Uani 1 1 d . . . H10 H 0.4849 0.3572 0.4956 0.031 Uiso 1 1 calc R . . C11 C 0.3688(3) 0.3941(3) 0.59894(19) 0.0253(6) Uani 1 1 d . . . H11 H 0.3269 0.4813 0.5685 0.030 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 Ni1 0.0207(2) 0.0155(2) 0.0163(2) -0.00193(15) 0.00697(16) -0.00283(15) O1 0.0261(8) 0.0188(8) 0.0149(8) 0.0012(7) 0.0043(6) 0.0075(7) O2 0.0604(14) 0.0351(12) 0.0194(9) -0.0017(8) 0.0043(9) 0.0338(11) O3 0.0584(14) 0.0277(11) 0.0364(11) 0.0084(9) 0.0303(10) 0.0157(10) O4 0.0358(10) 0.0198(10) 0.0310(10) 0.0096(8) 0.0173(8) 0.0071(8) O5 0.0260(9) 0.0263(10) 0.0245(9) -0.0021(7) 0.0085(7) -0.0077(8) O6 0.0361(10) 0.0325(11) 0.0194(8) 0.0043(8) -0.0016(7) -0.0136(8) N1 0.0198(10) 0.0146(9) 0.0162(9) 0.0001(7) 0.0056(8) 0.0038(8) N2 0.0243(10) 0.0178(10) 0.0220(10) 0.0044(8) 0.0095(8) 0.0059(8) N3 0.0206(10) 0.0175(10) 0.0196(10) -0.0015(8) 0.0078(8) 0.0049(8) C1 0.0218(12) 0.0184(12) 0.0176(11) -0.0002(9) 0.0030(9) 0.0056(9) C2 0.0199(11) 0.0132(11) 0.0165(11) -0.0022(9) 0.0023(9) 0.0030(9) C3 0.0210(12) 0.0181(12) 0.0189(12) -0.0004(9) 0.0073(9) 0.0046(9) C4 0.0219(11) 0.0162(12) 0.0179(11) 0.0000(9) 0.0061(9) 0.0010(9) C5 0.0232(12) 0.0182(12) 0.0210(12) 0.0038(9) 0.0081(9) 0.0031(10) C6 0.0183(11) 0.0140(11) 0.0207(11) -0.0007(9) 0.0065(9) 0.0023(9) C7 0.0268(13) 0.0249(13) 0.0188(11) 0.0042(10) 0.0096(10) 0.0042(10) C8 0.0241(12) 0.0208(12) 0.0241(12) 0.0073(10) 0.0076(10) 0.0092(10) C9 0.0190(11) 0.0160(12) 0.0216(12) -0.0010(9) 0.0075(9) 0.0023(9) C10 0.0339(14) 0.0216(13) 0.0252(13) 0.0063(10) 0.0146(11) 0.0079(11) C11 0.0307(13) 0.0211(13) 0.0263(13) 0.0069(10) 0.0116(11) 0.0119(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 Ni1 O4 2.0166(18) 4_566 ? Ni1 O1 2.0226(17) . ? Ni1 O6 2.0614(19) . ? Ni1 O5 2.0706(18) . ? Ni1 N3 2.083(2) 2_646 ? Ni1 N1 2.262(2) . ? O1 C1 1.257(3) . ? O2 C1 1.234(3) . ? O3 C5 1.230(3) . ? O4 C5 1.258(3) . ? O4 Ni1 2.0166(18) 4_565 ? O5 H5A 0.8500 . ? O5 H5B 0.8499 . ? O6 H6A 0.8501 . ? O6 H6B 0.8500 . ? N1 C6 1.346(3) . ? N1 C2 1.348(3) . ? N2 C4 1.328(3) . ? N2 C6 1.334(3) . ? N3 C11 1.339(3) . ? N3 C7 1.339(3) . ? N3 Ni1 2.083(2) 2_656 ? C1 C2 1.523(3) . ? C2 C3 1.373(3) . ? C3 C4 1.387(3) . ? C3 H3 0.9300 . ? C4 C5 1.532(3) . ? C6 C9 1.490(3) . ? C7 C8 1.380(4) . ? C7 H7 0.9300 . ? C8 C9 1.386(3) . ? C8 H8 0.9300 . ? C9 C10 1.396(4) . ? C10 C11 1.376(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 Ni1 O1 177.47(8) 4_566 . ? O4 Ni1 O6 91.50(9) 4_566 . ? O1 Ni1 O6 90.60(8) . . ? O4 Ni1 O5 92.49(8) 4_566 . ? O1 Ni1 O5 89.06(7) . . ? O6 Ni1 O5 86.61(8) . . ? O4 Ni1 N3 88.11(8) 4_566 2_646 ? O1 Ni1 N3 90.42(8) . 2_646 ? O6 Ni1 N3 91.38(8) . 2_646 ? O5 Ni1 N3 177.92(8) . 2_646 ? O4 Ni1 N1 101.21(8) 4_566 . ? O1 Ni1 N1 77.04(7) . . ? O6 Ni1 N1 162.72(8) . . ? O5 Ni1 N1 81.23(7) . . ? N3 Ni1 N1 100.61(8) 2_646 . ? C1 O1 Ni1 116.05(15) . . ? C5 O4 Ni1 133.61(17) . 4_565 ? Ni1 O5 H5A 110.0 . . ? Ni1 O5 H5B 108.5 . . ? H5A O5 H5B 113.3 . . ? Ni1 O6 H6A 119.9 . . ? Ni1 O6 H6B 116.2 . . ? H6A O6 H6B 111.0 . . ? C6 N1 C2 115.5(2) . . ? C6 N1 Ni1 132.24(16) . . ? C2 N1 Ni1 102.60(15) . . ? C4 N2 C6 117.8(2) . . ? C11 N3 C7 117.5(2) . . ? C11 N3 Ni1 118.64(17) . 2_656 ? C7 N3 Ni1 123.83(17) . 2_656 ? O2 C1 O1 126.1(2) . . ? O2 C1 C2 118.1(2) . . ? O1 C1 C2 115.8(2) . . ? N1 C2 C3 122.5(2) . . ? N1 C2 C1 115.7(2) . . ? C3 C2 C1 121.8(2) . . ? C2 C3 C4 117.1(2) . . ? C2 C3 H3 121.5 . . ? C4 C3 H3 121.5 . . ? N2 C4 C3 121.1(2) . . ? N2 C4 C5 117.8(2) . . ? C3 C4 C5 121.1(2) . . ? O3 C5 O4 127.5(2) . . ? O3 C5 C4 117.8(2) . . ? O4 C5 C4 114.7(2) . . ? N2 C6 N1 125.2(2) . . ? N2 C6 C9 115.6(2) . . ? N1 C6 C9 119.1(2) . . ? N3 C7 C8 123.1(2) . . ? N3 C7 H7 118.4 . . ? C8 C7 H7 118.4 . . ? C7 C8 C9 119.4(2) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C8 C9 C10 117.2(2) . . ? C8 C9 C6 123.7(2) . . ? C10 C9 C6 119.1(2) . . ? C11 C10 C9 119.7(2) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? N3 C11 C10 122.8(2) . . ? N3 C11 H11 118.6 . . ? C10 C11 H11 118.6 . . ? 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 O4 Ni1 O1 C1 72.0(17) 4_566 . . . ? O6 Ni1 O1 C1 -142.29(18) . . . . ? O5 Ni1 O1 C1 -55.70(18) . . . . ? N3 Ni1 O1 C1 126.32(18) 2_646 . . . ? N1 Ni1 O1 C1 25.52(17) . . . . ? O4 Ni1 N1 C6 8.4(2) 4_566 . . . ? O1 Ni1 N1 C6 -173.5(2) . . . . ? O6 Ni1 N1 C6 -128.2(3) . . . . ? O5 Ni1 N1 C6 -82.4(2) . . . . ? N3 Ni1 N1 C6 98.6(2) 2_646 . . . ? O4 Ni1 N1 C2 151.36(15) 4_566 . . . ? O1 Ni1 N1 C2 -30.52(15) . . . . ? O6 Ni1 N1 C2 14.8(3) . . . . ? O5 Ni1 N1 C2 60.54(15) . . . . ? N3 Ni1 N1 C2 -118.48(16) 2_646 . . . ? Ni1 O1 C1 O2 164.9(2) . . . . ? Ni1 O1 C1 C2 -15.3(3) . . . . ? C6 N1 C2 C3 5.2(3) . . . . ? Ni1 N1 C2 C3 -145.2(2) . . . . ? C6 N1 C2 C1 -177.1(2) . . . . ? Ni1 N1 C2 C1 32.6(2) . . . . ? O2 C1 C2 N1 164.2(2) . . . . ? O1 C1 C2 N1 -15.7(3) . . . . ? O2 C1 C2 C3 -18.0(4) . . . . ? O1 C1 C2 C3 162.1(2) . . . . ? N1 C2 C3 C4 2.7(4) . . . . ? C1 C2 C3 C4 -174.9(2) . . . . ? C6 N2 C4 C3 5.5(4) . . . . ? C6 N2 C4 C5 -172.9(2) . . . . ? C2 C3 C4 N2 -8.4(4) . . . . ? C2 C3 C4 C5 170.0(2) . . . . ? Ni1 O4 C5 O3 -31.2(4) 4_565 . . . ? Ni1 O4 C5 C4 146.61(19) 4_565 . . . ? N2 C4 C5 O3 -167.1(3) . . . . ? C3 C4 C5 O3 14.5(4) . . . . ? N2 C4 C5 O4 14.8(3) . . . . ? C3 C4 C5 O4 -163.6(2) . . . . ? C4 N2 C6 N1 3.4(4) . . . . ? C4 N2 C6 C9 -177.0(2) . . . . ? C2 N1 C6 N2 -8.6(4) . . . . ? Ni1 N1 C6 N2 130.7(2) . . . . ? C2 N1 C6 C9 171.8(2) . . . . ? Ni1 N1 C6 C9 -48.9(3) . . . . ? C11 N3 C7 C8 3.7(4) . . . . ? Ni1 N3 C7 C8 -175.5(2) 2_656 . . . ? N3 C7 C8 C9 -0.5(4) . . . . ? C7 C8 C9 C10 -3.3(4) . . . . ? C7 C8 C9 C6 177.6(2) . . . . ? N2 C6 C9 C8 174.1(2) . . . . ? N1 C6 C9 C8 -6.3(4) . . . . ? N2 C6 C9 C10 -5.0(3) . . . . ? N1 C6 C9 C10 174.7(2) . . . . ? C8 C9 C10 C11 3.8(4) . . . . ? C6 C9 C10 C11 -177.1(2) . . . . ? C7 N3 C11 C10 -3.2(4) . . . . ? Ni1 N3 C11 C10 176.1(2) 2_656 . . . ? C9 C10 C11 N3 -0.6(4) . . . . ? 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 O5 H5A O3 0.85 2.13 2.889(3) 148.7 4_566 O5 H5B O3 0.85 2.09 2.848(3) 148.4 3_756 O6 H6A O2 0.85 1.92 2.740(3) 160.3 4_556 O6 H6B O2 0.85 1.91 2.753(3) 173.1 2_756 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 67.08 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.802 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.078 data_b _database_code_depnum_ccdc_archive 'CCDC 917729' #TrackingRef 'polymer 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H7 Mn N3 O5' _chemical_formula_weight 316.14 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.4084(16) _cell_length_b 11.1150(16) _cell_length_c 8.8184(12) _cell_angle_alpha 90.00 _cell_angle_beta 92.036(2) _cell_angle_gamma 90.00 _cell_volume 1117.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2212 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 27.87 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.879 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 636 _exptl_absorpt_coefficient_mu 1.207 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7943 _exptl_absorpt_correction_T_max 0.8303 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7742 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0279 _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 -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 25.49 _reflns_number_total 2079 _reflns_number_gt 1763 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0769P)^2^+1.9312P] 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 2079 _refine_ls_number_parameters 177 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1340 _refine_ls_wR_factor_gt 0.1271 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 N3 N -0.1639(3) 0.1153(4) 0.3534(6) 0.0231(7) Uani 0.503(3) 1 d PG . 1 C7 C -0.0947(4) 0.2183(4) 0.3581(6) 0.0322(14) Uani 0.503(3) 1 d PG . 1 H7 H -0.1203 0.2867 0.4078 0.039 Uiso 0.503(3) 1 calc PR . 1 C8 C 0.0127(4) 0.2189(4) 0.2884(6) 0.0274(13) Uani 0.503(3) 1 d PG . 1 H8 H 0.0590 0.2878 0.2915 0.033 Uiso 0.503(3) 1 calc PR . 1 C9 C 0.0509(3) 0.1166(4) 0.2142(6) 0.0202(8) Uani 0.503(3) 1 d PGD . 1 C10 C -0.0183(4) 0.0137(4) 0.2095(6) 0.0250(12) Uani 0.503(3) 1 d PG . 1 H10 H 0.0073 -0.0548 0.1599 0.030 Uiso 0.503(3) 1 calc PR . 1 C11 C -0.1257(4) 0.0130(4) 0.2792(6) 0.0288(14) Uani 0.503(3) 1 d PG . 1 H11 H -0.1720 -0.0559 0.2761 0.035 Uiso 0.503(3) 1 calc PR . 1 N3' N -0.1648(4) 0.1241(4) 0.3466(6) 0.0231(7) Uani 0.497(3) 1 d PG . 2 C7' C -0.1300(4) 0.2204(4) 0.2603(6) 0.0322(14) Uani 0.497(3) 1 d PG . 2 H7' H -0.1795 0.2862 0.2458 0.039 Uiso 0.497(3) 1 calc PR . 2 C8' C -0.0216(4) 0.2191(4) 0.1956(6) 0.0274(13) Uani 0.497(3) 1 d PG . 2 H8' H 0.0019 0.2840 0.1374 0.033 Uiso 0.497(3) 1 calc PR . 2 C9' C 0.0519(4) 0.1216(4) 0.2172(6) 0.0202(8) Uani 0.497(3) 1 d PGD . 2 C10' C 0.0170(4) 0.0253(4) 0.3035(6) 0.0250(12) Uani 0.497(3) 1 d PG . 2 H10' H 0.0666 -0.0405 0.3180 0.030 Uiso 0.497(3) 1 calc PR . 2 C11' C -0.0913(4) 0.0266(4) 0.3682(6) 0.0288(14) Uani 0.497(3) 1 d PG . 2 H11' H -0.1148 -0.0383 0.4264 0.035 Uiso 0.497(3) 1 calc PR . 2 Mn1 Mn 0.36522(4) -0.38162(4) 0.09875(6) 0.0169(2) Uani 1 1 d . . . O1 O 0.3436(2) -0.1894(2) 0.0717(3) 0.0229(5) Uani 1 1 d . . . O2 O 0.3906(2) -0.1276(2) -0.1586(3) 0.0264(6) Uani 1 1 d . . . O3 O 0.3552(2) 0.4242(2) 0.1029(3) 0.0264(6) Uani 1 1 d . . . O4 O 0.4436(2) 0.3513(2) -0.0997(3) 0.0242(6) Uani 1 1 d . . . O5 O 0.3589(3) -0.4125(3) -0.1414(3) 0.0395(7) Uani 1 1 d . . . H1W H 0.3611 -0.3604 -0.2117 0.059 Uiso 1 1 d R . . H2W H 0.3877 -0.4820 -0.1553 0.059 Uiso 1 1 d R . . N1 N 0.2056(2) 0.0112(2) 0.0914(3) 0.0201(6) Uani 1 1 d . . . N2 N 0.2175(2) 0.2249(2) 0.1129(3) 0.0200(6) Uani 1 1 d . . . C1 C 0.3019(3) 0.0116(3) 0.0078(4) 0.0170(7) Uani 1 1 d . . . C2 C 0.3566(3) 0.1180(3) -0.0320(4) 0.0181(7) Uani 1 1 d . . . H2 H 0.4189 0.1186 -0.0972 0.022 Uiso 1 1 calc R . . C3 C 0.3139(3) 0.2236(3) 0.0302(4) 0.0178(7) Uani 1 1 d . . . C4 C 0.1658(3) 0.1189(3) 0.1346(4) 0.0185(7) Uani 1 1 d D . . C5 C 0.3489(3) -0.1123(3) -0.0328(4) 0.0158(7) Uani 1 1 d . . . C6 C 0.3768(3) 0.3432(3) 0.0099(4) 0.0198(7) 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 N3 0.0179(15) 0.0189(17) 0.0333(18) 0.0017(12) 0.0089(13) -0.0004(11) C7 0.020(3) 0.024(3) 0.054(4) -0.004(3) 0.015(3) 0.002(2) C8 0.021(3) 0.021(3) 0.041(4) 0.001(3) 0.011(3) -0.003(2) C9 0.0187(17) 0.0163(18) 0.0261(19) -0.0004(13) 0.0073(14) -0.0001(12) C10 0.024(3) 0.017(2) 0.035(3) 0.003(3) 0.015(3) 0.001(2) C11 0.018(3) 0.025(3) 0.045(4) 0.005(3) 0.011(3) -0.001(2) N3' 0.0179(15) 0.0189(17) 0.0333(18) 0.0017(12) 0.0089(13) -0.0004(11) C7' 0.020(3) 0.024(3) 0.054(4) -0.004(3) 0.015(3) 0.002(2) C8' 0.021(3) 0.021(3) 0.041(4) 0.001(3) 0.011(3) -0.003(2) C9' 0.0187(17) 0.0163(18) 0.0261(19) -0.0004(13) 0.0073(14) -0.0001(12) C10' 0.024(3) 0.017(2) 0.035(3) 0.003(3) 0.015(3) 0.001(2) C11' 0.018(3) 0.025(3) 0.045(4) 0.005(3) 0.011(3) -0.001(2) Mn1 0.0182(3) 0.0128(3) 0.0203(3) -0.00072(18) 0.0073(2) -0.00051(18) O1 0.0304(13) 0.0137(12) 0.0255(13) 0.0027(10) 0.0116(10) 0.0016(10) O2 0.0371(15) 0.0247(13) 0.0182(13) 0.0000(10) 0.0097(11) 0.0071(11) O3 0.0340(14) 0.0132(12) 0.0328(14) -0.0023(10) 0.0143(11) -0.0017(10) O4 0.0224(12) 0.0224(12) 0.0285(13) -0.0010(10) 0.0120(11) -0.0030(10) O5 0.065(2) 0.0281(14) 0.0249(14) 0.0037(12) -0.0023(13) 0.0095(14) N1 0.0186(14) 0.0143(14) 0.0280(15) 0.0011(11) 0.0082(12) 0.0005(11) N2 0.0173(14) 0.0145(14) 0.0288(16) 0.0005(11) 0.0084(12) 0.0001(11) C1 0.0183(15) 0.0153(16) 0.0177(16) -0.0025(12) 0.0025(13) -0.0007(13) C2 0.0180(16) 0.0165(17) 0.0203(17) 0.0000(12) 0.0060(14) 0.0007(12) C3 0.0176(15) 0.0135(16) 0.0225(17) 0.0025(12) 0.0032(13) 0.0004(13) C4 0.0156(16) 0.0175(17) 0.0228(17) 0.0024(13) 0.0053(14) 0.0010(12) C5 0.0142(15) 0.0136(16) 0.0196(17) -0.0015(12) 0.0026(13) -0.0019(12) C6 0.0187(16) 0.0147(16) 0.0263(18) -0.0004(13) 0.0053(14) 0.0010(13) _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 N3 C7 1.3900 . ? N3 C11 1.3900 . ? N3 Mn1 2.350(3) 2 ? C7 C8 1.3900 . ? C7 H7 0.9300 . ? C8 C9 1.3900 . ? C8 H8 0.9300 . ? C9 C10 1.3900 . ? C9 C4 1.509(4) . ? C10 C11 1.3900 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? N3' C7' 1.380(3) . ? N3' C11' 1.380(3) . ? N3' Mn1 2.354(4) 2 ? C7' C8' 1.380(3) . ? C7' H7' 0.9300 . ? C8' C9' 1.380(3) . ? C8' H8' 0.9300 . ? C9' C10' 1.380(3) . ? C9' C4 1.512(5) . ? C10' C11' 1.380(3) . ? C10' H10' 0.9300 . ? C11' H11' 0.9300 . ? Mn1 O5 2.144(3) . ? Mn1 O2 2.152(3) 4_556 ? Mn1 O3 2.161(3) 1_545 ? Mn1 O1 2.163(2) . ? Mn1 O4 2.206(2) 3_655 ? Mn1 N3 2.350(3) 2_545 ? Mn1 N3' 2.354(4) 2_545 ? O1 C5 1.262(4) . ? O2 C5 1.234(4) . ? O2 Mn1 2.152(3) 4 ? O3 C6 1.248(4) . ? O3 Mn1 2.161(3) 1_565 ? O4 C6 1.255(4) . ? O4 Mn1 2.206(2) 3_655 ? O5 H1W 0.8500 . ? O5 H2W 0.8500 . ? N1 C4 1.341(4) . ? N1 C1 1.345(4) . ? N2 C4 1.334(4) . ? N2 C3 1.342(4) . ? C1 C2 1.388(4) . ? C1 C5 1.525(4) . ? C2 C3 1.391(4) . ? C2 H2 0.9300 . ? C3 C6 1.525(4) . ? 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 C7 N3 C11 120.0 . . ? C7 N3 Mn1 122.7(2) . 2 ? C11 N3 Mn1 114.9(2) . 2 ? N3 C7 C8 120.0 . . ? N3 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C9 120.0 . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.0 . . ? C10 C9 C4 120.1(3) . . ? C8 C9 C4 119.9(3) . . ? C11 C10 C9 120.0 . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 N3 120.0 . . ? C10 C11 H11 120.0 . . ? N3 C11 H11 120.0 . . ? C7' N3' C11' 120.0 . . ? C7' N3' Mn1 115.8(2) . 2 ? C11' N3' Mn1 122.7(2) . 2 ? N3' C7' C8' 120.0 . . ? N3' C7' H7' 120.0 . . ? C8' C7' H7' 120.0 . . ? C9' C8' C7' 120.0 . . ? C9' C8' H8' 120.0 . . ? C7' C8' H8' 120.0 . . ? C10' C9' C8' 120.0 . . ? C10' C9' C4 121.3(3) . . ? C8' C9' C4 118.5(3) . . ? C9' C10' C11' 120.0 . . ? C9' C10' H10' 120.0 . . ? C11' C10' H10' 120.0 . . ? C10' C11' N3' 120.0 . . ? C10' C11' H11' 120.0 . . ? N3' C11' H11' 120.0 . . ? O5 Mn1 O2 171.32(11) . 4_556 ? O5 Mn1 O3 81.76(10) . 1_545 ? O2 Mn1 O3 92.07(9) 4_556 1_545 ? O5 Mn1 O1 92.85(10) . . ? O2 Mn1 O1 94.21(9) 4_556 . ? O3 Mn1 O1 169.17(10) 1_545 . ? O5 Mn1 O4 91.52(11) . 3_655 ? O2 Mn1 O4 83.74(10) 4_556 3_655 ? O3 Mn1 O4 101.86(9) 1_545 3_655 ? O1 Mn1 O4 87.60(9) . 3_655 ? O5 Mn1 N3 100.15(16) . 2_545 ? O2 Mn1 N3 85.42(15) 4_556 2_545 ? O3 Mn1 N3 85.97(13) 1_545 2_545 ? O1 Mn1 N3 85.75(13) . 2_545 ? O4 Mn1 N3 166.83(15) 3_655 2_545 ? O5 Mn1 N3' 101.99(16) . 2_545 ? O2 Mn1 N3' 83.84(15) 4_556 2_545 ? O3 Mn1 N3' 88.35(14) 1_545 2_545 ? O1 Mn1 N3' 83.57(14) . 2_545 ? O4 Mn1 N3' 164.17(14) 3_655 2_545 ? N3 Mn1 N3' 2.8(2) 2_545 2_545 ? C5 O1 Mn1 138.0(2) . . ? C5 O2 Mn1 147.6(2) . 4 ? C6 O3 Mn1 134.2(2) . 1_565 ? C6 O4 Mn1 129.5(2) . 3_655 ? Mn1 O5 H1W 127.6 . . ? Mn1 O5 H2W 106.8 . . ? H1W O5 H2W 119.5 . . ? C4 N1 C1 116.3(3) . . ? C4 N2 C3 116.3(3) . . ? N1 C1 C2 121.7(3) . . ? N1 C1 C5 115.2(3) . . ? C2 C1 C5 123.0(3) . . ? C1 C2 C3 116.9(3) . . ? C1 C2 H2 121.6 . . ? C3 C2 H2 121.6 . . ? N2 C3 C2 121.9(3) . . ? N2 C3 C6 116.9(3) . . ? C2 C3 C6 121.1(3) . . ? N2 C4 N1 126.3(3) . . ? N2 C4 C9 118.5(3) . . ? N1 C4 C9 115.2(3) . . ? N2 C4 C9' 116.3(3) . . ? N1 C4 C9' 117.4(3) . . ? C9 C4 C9' 2.3(3) . . ? O2 C5 O1 126.3(3) . . ? O2 C5 C1 119.0(3) . . ? O1 C5 C1 114.6(3) . . ? O3 C6 O4 126.4(3) . . ? O3 C6 C3 116.6(3) . . ? O4 C6 C3 117.0(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N3 C7 C8 0.0 . . . . ? Mn1 N3 C7 C8 -161.6(4) 2 . . . ? N3 C7 C8 C9 0.0 . . . . ? C7 C8 C9 C10 0.0 . . . . ? C7 C8 C9 C4 178.1(5) . . . . ? C8 C9 C10 C11 0.0 . . . . ? C4 C9 C10 C11 -178.1(5) . . . . ? C9 C10 C11 N3 0.0 . . . . ? C7 N3 C11 C10 0.0 . . . . ? Mn1 N3 C11 C10 163.0(3) 2 . . . ? C11' N3' C7' C8' 0.0 . . . . ? Mn1 N3' C7' C8' -166.3(3) 2 . . . ? N3' C7' C8' C9' 0.0 . . . . ? C7' C8' C9' C10' 0.0 . . . . ? C7' C8' C9' C4 175.3(5) . . . . ? C8' C9' C10' C11' 0.0 . . . . ? C4 C9' C10' C11' -175.1(5) . . . . ? C9' C10' C11' N3' 0.0 . . . . ? C7' N3' C11' C10' 0.0 . . . . ? Mn1 N3' C11' C10' 165.3(4) 2 . . . ? O5 Mn1 O1 C5 -13.8(3) . . . . ? O2 Mn1 O1 C5 161.2(3) 4_556 . . . ? O3 Mn1 O1 C5 -73.5(6) 1_545 . . . ? O4 Mn1 O1 C5 77.6(3) 3_655 . . . ? N3 Mn1 O1 C5 -113.7(4) 2_545 . . . ? N3' Mn1 O1 C5 -115.5(3) 2_545 . . . ? C4 N1 C1 C2 -0.2(5) . . . . ? C4 N1 C1 C5 177.0(3) . . . . ? N1 C1 C2 C3 5.8(5) . . . . ? C5 C1 C2 C3 -171.2(3) . . . . ? C4 N2 C3 C2 1.2(5) . . . . ? C4 N2 C3 C6 -177.6(3) . . . . ? C1 C2 C3 N2 -6.3(5) . . . . ? C1 C2 C3 C6 172.4(3) . . . . ? C3 N2 C4 N1 5.2(5) . . . . ? C3 N2 C4 C9 -174.4(3) . . . . ? C3 N2 C4 C9' -175.3(3) . . . . ? C1 N1 C4 N2 -5.7(5) . . . . ? C1 N1 C4 C9 173.9(3) . . . . ? C1 N1 C4 C9' 174.9(3) . . . . ? C10 C9 C4 N2 165.7(3) . . . . ? C8 C9 C4 N2 -12.4(5) . . . . ? C10 C9 C4 N1 -13.9(5) . . . . ? C8 C9 C4 N1 168.0(3) . . . . ? C10 C9 C4 C9' -172(8) . . . . ? C8 C9 C4 C9' 10(8) . . . . ? C10' C9' C4 N2 -151.2(3) . . . . ? C8' C9' C4 N2 33.6(5) . . . . ? C10' C9' C4 N1 28.3(5) . . . . ? C8' C9' C4 N1 -146.9(3) . . . . ? C10' C9' C4 C9 50(8) . . . . ? C8' C9' C4 C9 -125(8) . . . . ? Mn1 O2 C5 O1 125.4(4) 4 . . . ? Mn1 O2 C5 C1 -56.9(5) 4 . . . ? Mn1 O1 C5 O2 -13.4(6) . . . . ? Mn1 O1 C5 C1 168.8(2) . . . . ? N1 C1 C5 O2 143.3(3) . . . . ? C2 C1 C5 O2 -39.5(5) . . . . ? N1 C1 C5 O1 -38.7(4) . . . . ? C2 C1 C5 O1 138.4(3) . . . . ? Mn1 O3 C6 O4 22.7(6) 1_565 . . . ? Mn1 O3 C6 C3 -156.2(2) 1_565 . . . ? Mn1 O4 C6 O3 64.0(5) 3_655 . . . ? Mn1 O4 C6 C3 -117.1(3) 3_655 . . . ? N2 C3 C6 O3 19.4(5) . . . . ? C2 C3 C6 O3 -159.4(3) . . . . ? N2 C3 C6 O4 -159.6(3) . . . . ? C2 C3 C6 O4 21.6(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 O5 H1W O1 0.85 1.99 2.772(4) 152.2 4 O5 H1W O2 0.85 2.65 3.192(4) 122.9 . O5 H2W O4 0.85 2.01 2.817(4) 157.1 1_545 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.071 _refine_diff_density_min -0.590 _refine_diff_density_rms 0.105 data_aa _database_code_depnum_ccdc_archive 'CCDC 917730' #TrackingRef 'polymer 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 N3 O7 Zn' _chemical_formula_weight 362.60 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 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 17.422(2) _cell_length_b 9.8240(14) _cell_length_c 15.803(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.435(2) _cell_angle_gamma 90.00 _cell_volume 2607.2(6) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5627 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 28.15 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.848 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 1.927 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6444 _exptl_absorpt_correction_T_max 0.7609 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9616 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0141 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2417 _reflns_number_gt 2200 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+3.5705P] 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 2417 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0253 _refine_ls_R_factor_gt 0.0221 _refine_ls_wR_factor_ref 0.0629 _refine_ls_wR_factor_gt 0.0607 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 0.358521(12) 0.42721(2) 0.228417(14) 0.02241(9) Uani 1 1 d . . . O1 O 0.41942(8) 0.27509(13) 0.29784(9) 0.0251(3) Uani 1 1 d . . . O2 O 0.32853(8) 0.13730(15) 0.21504(10) 0.0321(3) Uani 1 1 d . . . O3 O 0.39762(9) -0.38008(14) 0.24965(9) 0.0304(3) Uani 1 1 d . . . O4 O 0.45904(11) -0.42403(15) 0.38901(11) 0.0452(4) Uani 1 1 d . . . O5 O 0.28331(9) 0.43038(15) 0.31872(10) 0.0337(4) Uani 1 1 d . . . H1W H 0.3122 0.4350 0.3712 0.051 Uiso 1 1 d R . . H2W H 0.2526 0.4989 0.3132 0.051 Uiso 1 1 d R . . O6 O 0.42089(9) 0.37607(15) 0.13373(9) 0.0331(3) Uani 1 1 d . . . H3W H 0.4686 0.3546 0.1597 0.050 Uiso 1 1 d R . . H4W H 0.4182 0.4337 0.0929 0.050 Uiso 1 1 d R . . O7 O 0.38765(11) 0.43351(17) 0.49217(11) 0.0474(4) Uani 1 1 d . . . H5W H 0.4140 0.4793 0.4639 0.071 Uiso 1 1 d R . . H6W H 0.4163 0.3743 0.5253 0.071 Uiso 1 1 d R . . N1 N 0.50804(9) 0.06454(15) 0.37804(10) 0.0206(3) Uani 1 1 d . . . N2 N 0.53008(9) -0.17404(16) 0.40313(10) 0.0204(3) Uani 1 1 d . . . N3 N 0.75919(9) 0.04247(16) 0.62538(10) 0.0228(3) Uani 1 1 d . . . C1 C 0.44083(10) 0.03710(19) 0.31611(11) 0.0180(4) Uani 1 1 d . . . C2 C 0.41661(11) -0.09562(18) 0.29271(12) 0.0194(4) Uani 1 1 d . . . H2 H 0.3713 -0.1141 0.2476 0.023 Uiso 1 1 calc R . . C3 C 0.46320(10) -0.19947(18) 0.33972(11) 0.0187(4) Uani 1 1 d . . . C4 C 0.55007(11) -0.04255(19) 0.41786(12) 0.0193(4) Uani 1 1 d . . . C5 C 0.39153(10) 0.15823(19) 0.27202(12) 0.0203(4) Uani 1 1 d . . . C6 C 0.43817(11) -0.34746(19) 0.32538(13) 0.0229(4) Uani 1 1 d . . . C7 C 0.71552(12) 0.1426(2) 0.57945(13) 0.0298(5) Uani 1 1 d . . . H7 H 0.7308 0.2320 0.5943 0.036 Uiso 1 1 calc R . . C8 C 0.64857(12) 0.1199(2) 0.51086(13) 0.0297(5) Uani 1 1 d . . . H8 H 0.6199 0.1928 0.4806 0.036 Uiso 1 1 calc R . . C9 C 0.62471(11) -0.01220(19) 0.48760(12) 0.0212(4) Uani 1 1 d . . . C10 C 0.67108(13) -0.1163(2) 0.53421(16) 0.0401(6) Uani 1 1 d . . . H10 H 0.6578 -0.2066 0.5198 0.048 Uiso 1 1 calc R . . C11 C 0.73684(14) -0.0852(2) 0.60189(16) 0.0393(6) Uani 1 1 d . . . H11 H 0.7671 -0.1563 0.6326 0.047 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 0.01970(14) 0.01381(14) 0.02581(14) 0.00003(8) -0.00776(9) 0.00125(8) O1 0.0229(7) 0.0142(7) 0.0319(7) 0.0017(5) -0.0038(6) 0.0013(5) O2 0.0224(7) 0.0244(8) 0.0386(8) 0.0066(6) -0.0109(6) -0.0025(6) O3 0.0338(8) 0.0176(7) 0.0308(8) -0.0037(6) -0.0073(6) -0.0062(6) O4 0.0572(11) 0.0246(9) 0.0392(9) 0.0114(7) -0.0127(8) -0.0099(7) O5 0.0274(8) 0.0350(9) 0.0335(8) -0.0001(6) -0.0011(6) 0.0076(6) O6 0.0310(8) 0.0307(8) 0.0350(8) 0.0051(6) 0.0042(6) 0.0058(6) O7 0.0532(11) 0.0425(11) 0.0404(10) 0.0067(7) 0.0019(8) -0.0008(8) N1 0.0181(8) 0.0166(8) 0.0228(8) -0.0002(6) -0.0021(6) -0.0010(6) N2 0.0185(7) 0.0168(8) 0.0212(8) -0.0006(6) -0.0030(6) -0.0002(6) N3 0.0175(8) 0.0198(8) 0.0252(8) 0.0008(6) -0.0048(6) -0.0017(6) C1 0.0162(9) 0.0165(9) 0.0186(9) 0.0017(7) -0.0004(7) 0.0006(7) C2 0.0158(9) 0.0182(9) 0.0200(9) -0.0004(7) -0.0027(7) -0.0008(7) C3 0.0179(9) 0.0167(9) 0.0187(8) -0.0003(7) 0.0002(7) -0.0008(7) C4 0.0182(9) 0.0170(9) 0.0194(9) -0.0008(7) -0.0009(7) -0.0008(7) C5 0.0173(9) 0.0181(9) 0.0232(9) 0.0039(7) 0.0011(7) 0.0010(7) C6 0.0190(9) 0.0162(9) 0.0290(10) -0.0005(8) -0.0016(8) -0.0001(7) C7 0.0286(11) 0.0183(10) 0.0323(11) -0.0004(8) -0.0095(9) -0.0044(8) C8 0.0293(11) 0.0178(10) 0.0312(11) 0.0043(8) -0.0108(8) -0.0005(8) C9 0.0175(9) 0.0200(10) 0.0213(9) 0.0003(7) -0.0029(7) -0.0006(7) C10 0.0342(12) 0.0158(10) 0.0521(14) -0.0023(10) -0.0205(10) -0.0006(9) C11 0.0332(12) 0.0205(11) 0.0470(14) 0.0034(9) -0.0194(10) 0.0032(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.9857(13) . ? Zn1 O3 2.0098(14) 1_565 ? Zn1 N3 2.0579(15) 8_455 ? Zn1 O6 2.1301(15) . ? Zn1 O5 2.1794(16) . ? O1 C5 1.271(2) . ? O2 C5 1.238(2) . ? O3 C6 1.258(2) . ? O3 Zn1 2.0098(14) 1_545 ? O4 C6 1.231(2) . ? O5 H1W 0.8500 . ? O5 H2W 0.8499 . ? O6 H3W 0.8500 . ? O6 H4W 0.8500 . ? O7 H5W 0.8500 . ? O7 H6W 0.8501 . ? N1 C1 1.339(2) . ? N1 C4 1.339(2) . ? N2 C4 1.342(2) . ? N2 C3 1.343(2) . ? N3 C11 1.336(3) . ? N3 C7 1.334(3) . ? N3 Zn1 2.0579(15) 8_556 ? C1 C2 1.390(3) . ? C1 C5 1.523(2) . ? C2 C3 1.389(3) . ? C2 H2 0.9300 . ? C3 C6 1.517(3) . ? C4 C9 1.494(2) . ? C7 C8 1.383(3) . ? C7 H7 0.9300 . ? C8 C9 1.382(3) . ? C8 H8 0.9300 . ? C9 C10 1.387(3) . ? C10 C11 1.377(3) . ? 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 O1 Zn1 O3 120.61(5) . 1_565 ? O1 Zn1 N3 139.40(6) . 8_455 ? O3 Zn1 N3 99.91(6) 1_565 8_455 ? O1 Zn1 O6 85.02(6) . . ? O3 Zn1 O6 97.23(6) 1_565 . ? N3 Zn1 O6 87.54(6) 8_455 . ? O1 Zn1 O5 88.57(6) . . ? O3 Zn1 O5 96.51(6) 1_565 . ? N3 Zn1 O5 89.46(6) 8_455 . ? O6 Zn1 O5 166.25(6) . . ? C5 O1 Zn1 113.58(11) . . ? C6 O3 Zn1 118.56(13) . 1_545 ? Zn1 O5 H1W 109.7 . . ? Zn1 O5 H2W 114.6 . . ? H1W O5 H2W 104.5 . . ? Zn1 O6 H3W 109.6 . . ? Zn1 O6 H4W 116.1 . . ? H3W O6 H4W 112.4 . . ? H5W O7 H6W 112.0 . . ? C1 N1 C4 116.60(15) . . ? C4 N2 C3 116.24(15) . . ? C11 N3 C7 117.32(16) . . ? C11 N3 Zn1 118.51(13) . 8_556 ? C7 N3 Zn1 124.17(13) . 8_556 ? N1 C1 C2 121.87(16) . . ? N1 C1 C5 117.01(16) . . ? C2 C1 C5 121.12(15) . . ? C1 C2 C3 116.99(16) . . ? C1 C2 H2 121.5 . . ? C3 C2 H2 121.5 . . ? N2 C3 C2 121.99(16) . . ? N2 C3 C6 116.59(15) . . ? C2 C3 C6 121.32(16) . . ? N1 C4 N2 126.19(16) . . ? N1 C4 C9 116.71(16) . . ? N2 C4 C9 117.06(16) . . ? O2 C5 O1 124.96(17) . . ? O2 C5 C1 119.07(16) . . ? O1 C5 C1 115.97(15) . . ? O4 C6 O3 126.18(18) . . ? O4 C6 C3 116.93(17) . . ? O3 C6 C3 116.89(16) . . ? N3 C7 C8 123.21(18) . . ? N3 C7 H7 118.4 . . ? C8 C7 H7 118.4 . . ? C7 C8 C9 119.42(18) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C8 C9 C10 117.34(18) . . ? C8 C9 C4 121.65(16) . . ? C10 C9 C4 120.95(17) . . ? C11 C10 C9 119.7(2) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? N3 C11 C10 123.00(19) . . ? N3 C11 H11 118.5 . . ? C10 C11 H11 118.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Zn1 O1 C5 -174.04(12) 1_565 . . . ? N3 Zn1 O1 C5 1.75(18) 8_455 . . . ? O6 Zn1 O1 C5 -78.58(13) . . . . ? O5 Zn1 O1 C5 89.24(13) . . . . ? C4 N1 C1 C2 -1.4(3) . . . . ? C4 N1 C1 C5 178.51(16) . . . . ? N1 C1 C2 C3 3.3(3) . . . . ? C5 C1 C2 C3 -176.68(16) . . . . ? C4 N2 C3 C2 -0.8(3) . . . . ? C4 N2 C3 C6 -177.36(16) . . . . ? C1 C2 C3 N2 -2.1(3) . . . . ? C1 C2 C3 C6 174.30(16) . . . . ? C1 N1 C4 N2 -1.9(3) . . . . ? C1 N1 C4 C9 -179.45(16) . . . . ? C3 N2 C4 N1 3.0(3) . . . . ? C3 N2 C4 C9 -179.44(16) . . . . ? Zn1 O1 C5 O2 -6.6(2) . . . . ? Zn1 O1 C5 C1 173.53(12) . . . . ? N1 C1 C5 O2 -179.25(17) . . . . ? C2 C1 C5 O2 0.7(3) . . . . ? N1 C1 C5 O1 0.6(2) . . . . ? C2 C1 C5 O1 -179.45(17) . . . . ? Zn1 O3 C6 O4 2.4(3) 1_545 . . . ? Zn1 O3 C6 C3 -177.19(12) 1_545 . . . ? N2 C3 C6 O4 27.4(3) . . . . ? C2 C3 C6 O4 -149.1(2) . . . . ? N2 C3 C6 O3 -153.00(17) . . . . ? C2 C3 C6 O3 30.5(3) . . . . ? C11 N3 C7 C8 1.1(3) . . . . ? Zn1 N3 C7 C8 -179.46(17) 8_556 . . . ? N3 C7 C8 C9 -0.1(3) . . . . ? C7 C8 C9 C10 -1.2(3) . . . . ? C7 C8 C9 C4 176.08(19) . . . . ? N1 C4 C9 C8 1.0(3) . . . . ? N2 C4 C9 C8 -176.81(19) . . . . ? N1 C4 C9 C10 178.2(2) . . . . ? N2 C4 C9 C10 0.4(3) . . . . ? C8 C9 C10 C11 1.4(4) . . . . ? C4 C9 C10 C11 -175.9(2) . . . . ? C7 N3 C11 C10 -0.9(4) . . . . ? Zn1 N3 C11 C10 179.6(2) 8_556 . . . ? C9 C10 C11 N3 -0.4(4) . . . . ? 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 O5 H1W O7 0.85 2.01 2.858(2) 174.6 . O5 H2W O2 0.85 1.93 2.768(2) 170.4 4 O6 H3W O1 0.85 2.04 2.880(2) 168.4 2_655 O6 H4W O7 0.85 2.02 2.855(2) 168.4 6_565 O6 H4W O4 0.85 2.51 2.960(2) 114.3 2_665 O7 H5W O4 0.85 1.85 2.691(3) 172.0 1_565 O7 H6W O4 0.85 2.29 2.828(2) 121.9 5_656 O7 H6W N2 0.85 2.34 3.167(2) 165.5 5_656 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.412 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.055