Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Anthony K. Cheetham' _publ_contact_author_address ; Materials Research Laboratory University of California Santa Barbara, Ca. 93106 ; _publ_contact_author_email cheetham@mrl.ucsb.edu _publ_contact_author_phone '(805) 893-8767' _publ_contact_author_fax '(805) 893-8797' _publ_section_title ; Polytypism, Homochirality, Interpenetration, and Hydrogen-Bonding in Transition Metal (Mn(II), Ni(II), Cu(II), Zn(II)) 5-Hydroxyisophthalate Coordination Polymers Containing 4,4'-Bipyridyl ; loop_ _publ_author_name R.K.Feller A.K.Cheetham data_mnyeloam _database_code_depnum_ccdc_archive 'CCDC 657326' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 Mn N2 O8' _chemical_formula_weight 445.28 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/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 10.1726(11) _cell_length_b 11.6397(13) _cell_length_c 16.2535(18) _cell_angle_alpha 90.00 _cell_angle_beta 103.310(3) _cell_angle_gamma 90.00 _cell_volume 1872.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour 'Pale Yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 916 _exptl_absorpt_coefficient_mu 0.756 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2446 _exptl_absorpt_correction_T_max 0.3412 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15276 _diffrn_reflns_av_R_equivalents 0.0971 _diffrn_reflns_av_sigmaI/netI 0.0950 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 26.91 _reflns_number_total 3893 _reflns_number_gt 2234 _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^)+(0.0766P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3893 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1083 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1486 _refine_ls_wR_factor_gt 0.1313 _refine_ls_goodness_of_fit_ref 0.929 _refine_ls_restrained_S_all 0.929 _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 Mn1 Mn 0.38258(5) 0.65341(4) 0.83323(4) 0.0300(2) Uani 1 1 d . . . N1 N 0.3854(4) 0.8500(2) 0.8285(2) 0.0431(8) Uani 1 1 d . . . N2 N 0.3953(3) 0.4595(2) 0.83034(19) 0.0344(7) Uani 1 1 d . . . O1 O 0.1574(3) 0.6275(3) 0.82769(19) 0.0563(8) Uani 1 1 d . . . O2 O 0.2902(3) 0.6712(3) 0.94757(19) 0.0571(8) Uani 1 1 d . . . O3 O -0.3424(3) 0.6544(2) 0.79949(17) 0.0439(7) Uani 1 1 d . . . O4 O -0.4195(2) 0.6562(2) 0.91502(17) 0.0396(6) Uani 1 1 d . . . C3 C 0.3875(4) 1.0907(3) 0.8291(2) 0.0343(9) Uani 1 1 d . . . C6 C 0.3100(4) 0.4005(3) 0.7703(3) 0.0437(11) Uani 1 1 d . B . H6 H 0.2512 0.4413 0.7281 0.052 Uiso 1 1 calc R . . C7 C 0.3048(4) 0.2815(3) 0.7677(3) 0.0436(11) Uani 1 1 d . . . H7 H 0.2433 0.2443 0.7247 0.052 Uiso 1 1 calc R B . C8 C 0.3911(4) 0.2184(3) 0.8292(2) 0.0355(9) Uani 1 1 d . . . C9 C 0.4794(4) 0.2796(3) 0.8911(3) 0.0419(10) Uani 1 1 d . . . H9 H 0.5395 0.2407 0.9338 0.050 Uiso 1 1 calc R B . C10 C 0.4785(4) 0.3974(3) 0.8896(2) 0.0385(10) Uani 1 1 d . B . H10 H 0.5391 0.4362 0.9321 0.046 Uiso 1 1 calc R . . C11 C 0.0551(4) 0.6530(4) 0.9432(3) 0.0449(10) Uani 1 1 d . . . C15 C -0.1842(4) 0.6525(3) 0.9308(2) 0.0411(9) Uani 1 1 d . . . C16 C -0.0752(4) 0.6535(3) 0.8932(2) 0.0346(8) Uani 1 1 d . A . H16 H -0.0893 0.6545 0.8346 0.041 Uiso 1 1 calc R . . C17 C 0.1751(4) 0.6513(3) 0.9040(3) 0.0363(9) Uani 1 1 d . A . C18 C -0.3252(4) 0.6546(3) 0.8776(2) 0.0287(8) Uani 1 1 d . A . C12A C 0.0758(8) 0.6296(5) 1.0312(6) 0.0424(17) Uani 0.616(3) 1 d P A 1 H12A H 0.1632 0.6212 1.0640 0.051 Uiso 0.616(3) 1 calc PR A 1 C14A C -0.1615(8) 0.6258(5) 1.0178(5) 0.0389(15) Uani 0.616(3) 1 d P A 1 H14A H -0.2351 0.6124 1.0414 0.047 Uiso 0.616(3) 1 calc PR A 1 C13A C -0.0330(7) 0.6192(6) 1.0682(4) 0.0399(14) Uani 0.616(3) 1 d P A 1 O5A O -0.0049(5) 0.6018(5) 1.1539(3) 0.0610(13) Uani 0.616(3) 1 d P A 1 H5A H -0.0758 0.5961 1.1695 0.092 Uiso 0.616(3) 1 calc PR A 1 OWA O -0.0103(16) 0.8801(13) 1.2035(11) 0.131(8) Uani 0.3082(15) 1 d P . 1 C12B C 0.0762(15) 0.6905(10) 1.0262(10) 0.0424(17) Uani 0.384(3) 1 d P A 2 H12B H 0.1627 0.7092 1.0564 0.051 Uiso 0.384(3) 1 calc PR A 2 C14B C -0.1604(13) 0.6898(9) 1.0150(9) 0.0389(15) Uani 0.384(3) 1 d P A 2 H14B H -0.2330 0.7081 1.0385 0.047 Uiso 0.384(3) 1 calc PR A 2 C13B C -0.0304(11) 0.6997(10) 1.0633(7) 0.0399(14) Uani 0.384(3) 1 d P A 2 O5B O -0.0082(8) 0.7233(8) 1.1500(5) 0.0610(13) Uani 0.384(3) 1 d P A 2 H5B H 0.0731 0.7291 1.1703 0.092 Uiso 0.384(3) 1 calc PR A 2 OWB O 0.0000 0.5368(10) 1.2500 0.072(4) Uani 0.384(3) 2 d SP A 2 C4A C 0.5048(9) 1.0285(7) 0.8674(6) 0.050(2) Uani 0.552(4) 1 d P B 3 H4A H 0.5834 1.0668 0.8938 0.060 Uiso 0.552(4) 1 calc PR B 3 C5A C 0.5013(10) 0.9105(8) 0.8651(6) 0.053(2) Uani 0.552(4) 1 d P B 3 H5A1 H 0.5794 0.8698 0.8890 0.063 Uiso 0.552(4) 1 calc PR B 3 C2A C 0.2747(9) 1.0289(7) 0.7948(6) 0.056(2) Uani 0.552(4) 1 d P B 3 H2A H 0.1950 1.0669 0.7698 0.067 Uiso 0.552(4) 1 calc PR B 3 C1A C 0.2773(10) 0.9109(7) 0.7968(6) 0.056(3) Uani 0.552(4) 1 d P B 3 H1A H 0.1974 0.8718 0.7742 0.068 Uiso 0.552(4) 1 calc PR B 3 C4B C 0.4422(11) 1.0269(9) 0.8975(8) 0.050(2) Uani 0.448(4) 1 d P B 4 H4B H 0.4831 1.0625 0.9482 0.060 Uiso 0.448(4) 1 calc PR B 4 C5B C 0.4376(13) 0.9094(11) 0.8923(9) 0.053(2) Uani 0.448(4) 1 d P B 4 H5B1 H 0.4773 0.8693 0.9412 0.063 Uiso 0.448(4) 1 calc PR B 4 C2B C 0.3311(10) 1.0332(9) 0.7551(8) 0.056(2) Uani 0.448(4) 1 d P B 4 H2B H 0.2935 1.0737 0.7060 0.067 Uiso 0.448(4) 1 calc PR B 4 C1B C 0.3315(12) 0.9106(9) 0.7551(9) 0.056(3) Uani 0.448(4) 1 d P B 4 H1B H 0.2953 0.8710 0.7053 0.068 Uiso 0.448(4) 1 calc PR B 4 OW1 O -0.0155(17) 1.0701(19) 1.1973(12) 0.282(14) Uani 0.50 1 d P . . OW2 O -0.0154(16) 0.9795(10) 1.1377(17) 0.234(12) Uani 0.50 1 d P . . OW3 O -0.010(7) 0.991(5) 1.072(3) 0.48(4) Uani 0.50 1 d P . . OW4 O -0.184(3) 1.056(4) 0.973(2) 0.45(2) Uani 0.50 1 d P . . OW5 O 0.082(4) 1.0648(17) 1.023(4) 0.37(2) Uani 0.50 1 d P . . 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 Mn1 0.0244(3) 0.0264(3) 0.0386(4) 0.0004(3) 0.0062(2) -0.0006(3) N1 0.048(2) 0.0275(15) 0.053(2) 0.0009(18) 0.0094(17) -0.0001(18) N2 0.0306(17) 0.0287(15) 0.0420(18) -0.0007(16) 0.0042(15) -0.0017(14) O1 0.0288(16) 0.098(3) 0.0425(18) -0.0061(16) 0.0096(14) 0.0021(15) O2 0.0227(16) 0.095(2) 0.0528(18) -0.0137(16) 0.0066(14) -0.0081(15) O3 0.0373(16) 0.0532(16) 0.0376(16) -0.0010(13) 0.0010(13) 0.0052(13) O4 0.0238(14) 0.0489(15) 0.0462(16) -0.0007(13) 0.0081(12) -0.0019(12) C3 0.036(2) 0.0294(18) 0.038(2) -0.0030(19) 0.0081(18) 0.0022(18) C6 0.043(3) 0.034(2) 0.046(3) 0.0084(19) -0.006(2) 0.0018(18) C7 0.045(3) 0.032(2) 0.046(3) -0.0026(19) -0.005(2) -0.0050(18) C8 0.040(2) 0.0259(18) 0.043(2) -0.0010(18) 0.0136(19) 0.0016(18) C9 0.043(3) 0.031(2) 0.047(3) 0.0055(18) -0.001(2) 0.0035(18) C10 0.039(2) 0.037(2) 0.036(2) 0.0004(18) 0.001(2) -0.0022(18) C11 0.025(2) 0.068(3) 0.042(2) -0.003(2) 0.0084(18) -0.004(2) C15 0.027(2) 0.064(3) 0.031(2) -0.003(2) 0.0058(17) 0.000(2) C16 0.027(2) 0.045(2) 0.032(2) -0.0016(18) 0.0059(16) 0.0018(18) C17 0.029(2) 0.042(2) 0.040(2) 0.0025(19) 0.0131(18) 0.0005(18) C18 0.0254(19) 0.0207(16) 0.038(2) -0.0011(17) 0.0042(16) -0.0013(15) C12A 0.027(3) 0.051(5) 0.045(3) -0.001(5) 0.000(2) -0.001(4) C14A 0.029(3) 0.047(4) 0.043(3) 0.003(5) 0.012(2) 0.002(4) C13A 0.033(3) 0.058(4) 0.028(3) -0.001(4) 0.007(2) -0.006(4) O5A 0.036(2) 0.109(3) 0.037(2) 0.004(3) 0.0068(19) 0.001(3) OWA 0.052(8) 0.079(9) 0.24(2) -0.035(10) -0.012(15) -0.013(8) C12B 0.027(3) 0.051(5) 0.045(3) -0.001(5) 0.000(2) -0.001(4) C14B 0.029(3) 0.047(4) 0.043(3) 0.003(5) 0.012(2) 0.002(4) C13B 0.033(3) 0.058(4) 0.028(3) -0.001(4) 0.007(2) -0.006(4) O5B 0.036(2) 0.109(3) 0.037(2) 0.004(3) 0.0068(19) 0.001(3) OWB 0.079(9) 0.067(8) 0.074(9) 0.000 0.025(7) 0.000 C4A 0.045(5) 0.037(3) 0.066(6) -0.014(4) 0.006(3) -0.006(4) C5A 0.054(7) 0.033(3) 0.063(6) 0.001(4) -0.003(4) 0.005(4) C2A 0.030(5) 0.039(3) 0.090(7) 0.000(4) -0.002(3) -0.001(4) C1A 0.044(6) 0.027(3) 0.086(8) -0.003(4) -0.009(4) 0.000(4) C4B 0.045(5) 0.037(3) 0.066(6) -0.014(4) 0.006(3) -0.006(4) C5B 0.054(7) 0.033(3) 0.063(6) 0.001(4) -0.003(4) 0.005(4) C2B 0.030(5) 0.039(3) 0.090(7) 0.000(4) -0.002(3) -0.001(4) C1B 0.044(6) 0.027(3) 0.086(8) -0.003(4) -0.009(4) 0.000(4) OW1 0.129(13) 0.30(2) 0.37(4) 0.16(2) -0.04(2) -0.038(16) OW2 0.167(13) 0.058(7) 0.45(3) -0.086(13) 0.005(17) 0.009(8) OW3 0.75(8) 0.46(5) 0.42(5) 0.00(4) 0.50(6) 0.07(5) OW4 0.34(4) 0.60(6) 0.38(4) -0.07(4) 0.01(4) -0.21(4) OW5 0.46(4) 0.138(14) 0.58(6) -0.01(2) 0.26(4) 0.092(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 Mn1 O3 2.101(3) 2_556 ? Mn1 O4 2.142(3) 1_655 ? Mn1 N2 2.261(3) . ? Mn1 O2 2.277(3) . ? Mn1 N1 2.290(3) . ? Mn1 O1 2.291(3) . ? Mn1 C17 2.626(4) . ? N1 C5B 1.258(14) . ? N1 C1A 1.309(9) . ? N1 C5A 1.384(10) . ? N1 C1B 1.385(13) . ? N2 C6 1.338(4) . ? N2 C10 1.339(4) . ? O1 C17 1.243(5) . ? O2 C17 1.242(5) . ? O3 C18 1.242(4) . ? O3 Mn1 2.101(3) 2_556 ? O4 C18 1.249(4) . ? O4 Mn1 2.142(3) 1_455 ? C3 C4B 1.347(12) . ? C3 C2A 1.360(9) . ? C3 C2B 1.380(12) . ? C3 C4A 1.412(9) . ? C3 C8 1.487(5) 1_565 ? C6 C7 1.386(5) . ? C6 H6 0.9300 . ? C7 C8 1.380(5) . ? C7 H7 0.9300 . ? C8 C9 1.382(5) . ? C8 C3 1.487(5) 1_545 ? C9 C10 1.372(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C16 1.386(5) . ? C11 C12B 1.387(17) . ? C11 C12A 1.423(10) . ? C11 C17 1.502(6) . ? C15 C16 1.384(5) . ? C15 C14B 1.403(15) . ? C15 C14A 1.413(9) . ? C15 C18 1.494(5) . ? C16 H16 0.9300 . ? C12A C13A 1.382(11) . ? C12A H12A 0.9300 . ? C14A C13A 1.376(10) . ? C14A H14A 0.9300 . ? C13A O5A 1.371(8) . ? O5A H5A 0.8200 . ? OWA OWA 1.48(4) 2_557 ? OWA OW2 1.57(3) . ? C12B C13B 1.361(19) . ? C12B H12B 0.9300 . ? C14B C13B 1.379(17) . ? C14B H14B 0.9300 . ? C13B O5B 1.403(13) . ? O5B H5B 0.8200 . ? C4A C5A 1.374(12) . ? C4A H4A 0.9300 . ? C5A H5A1 0.9300 . ? C2A C1A 1.375(11) . ? C2A H2A 0.9300 . ? C1A H1A 0.9300 . ? C4B C5B 1.370(15) . ? C4B H4B 0.9300 . ? C5B H5B1 0.9300 . ? C2B C1B 1.427(15) . ? C2B H2B 0.9300 . ? C1B H1B 0.9300 . ? OW1 OW2 1.43(3) . ? OW1 OW1 1.67(4) 2_557 ? OW2 OW3 1.09(4) . ? OW3 OW5 1.61(4) . ? OW3 OW5 1.67(6) 3_577 ? OW4 OW5 1.74(5) 3_577 ? OW5 OW3 1.67(6) 3_577 ? OW5 OW4 1.74(5) 3_577 ? 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 Mn1 O4 124.75(11) 2_556 1_655 ? O3 Mn1 N2 89.01(10) 2_556 . ? O4 Mn1 N2 88.73(10) 1_655 . ? O3 Mn1 O2 144.90(11) 2_556 . ? O4 Mn1 O2 89.86(10) 1_655 . ? N2 Mn1 O2 98.28(11) . . ? O3 Mn1 N1 87.75(11) 2_556 . ? O4 Mn1 N1 89.35(11) 1_655 . ? N2 Mn1 N1 174.39(12) . . ? O2 Mn1 N1 86.98(12) . . ? O3 Mn1 O1 90.22(11) 2_556 . ? O4 Mn1 O1 144.54(11) 1_655 . ? N2 Mn1 O1 85.96(11) . . ? O2 Mn1 O1 56.45(10) . . ? N1 Mn1 O1 98.63(12) . . ? O3 Mn1 C17 117.63(12) 2_556 . ? O4 Mn1 C17 117.61(12) 1_655 . ? N2 Mn1 C17 93.16(11) . . ? O2 Mn1 C17 28.22(11) . . ? N1 Mn1 C17 92.39(12) . . ? O1 Mn1 C17 28.25(11) . . ? C5B N1 C1A 100.6(7) . . ? C5B N1 C5A 37.8(6) . . ? C1A N1 C5A 116.7(6) . . ? C5B N1 C1B 116.0(8) . . ? C1A N1 C1B 42.0(5) . . ? C5A N1 C1B 103.9(7) . . ? C5B N1 Mn1 121.8(6) . . ? C1A N1 Mn1 122.5(5) . . ? C5A N1 Mn1 120.6(4) . . ? C1B N1 Mn1 122.1(5) . . ? C6 N2 C10 116.4(3) . . ? C6 N2 Mn1 119.8(2) . . ? C10 N2 Mn1 123.6(2) . . ? C17 O1 Mn1 91.0(2) . . ? C17 O2 Mn1 91.7(2) . . ? C18 O3 Mn1 177.0(3) . 2_556 ? C18 O4 Mn1 114.6(2) . 1_455 ? C4B C3 C2A 101.3(7) . . ? C4B C3 C2B 117.5(7) . . ? C2A C3 C2B 40.9(5) . . ? C4B C3 C4A 37.5(5) . . ? C2A C3 C4A 117.2(5) . . ? C2B C3 C4A 105.9(6) . . ? C4B C3 C8 123.0(6) . 1_565 ? C2A C3 C8 123.2(5) . 1_565 ? C2B C3 C8 119.4(6) . 1_565 ? C4A C3 C8 119.6(5) . 1_565 ? N2 C6 C7 123.3(3) . . ? N2 C6 H6 118.3 . . ? C7 C6 H6 118.3 . . ? C8 C7 C6 119.8(4) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 116.8(3) . . ? C7 C8 C3 121.3(4) . 1_545 ? C9 C8 C3 121.8(4) . 1_545 ? C10 C9 C8 120.1(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? N2 C10 C9 123.6(4) . . ? N2 C10 H10 118.2 . . ? C9 C10 H10 118.2 . . ? C16 C11 C12B 118.8(7) . . ? C16 C11 C12A 119.4(5) . . ? C12B C11 C12A 29.4(5) . . ? C16 C11 C17 120.9(4) . . ? C12B C11 C17 117.3(7) . . ? C12A C11 C17 118.5(5) . . ? C16 C15 C14B 116.9(6) . . ? C16 C15 C14A 118.7(4) . . ? C14B C15 C14A 30.8(4) . . ? C16 C15 C18 120.3(3) . . ? C14B C15 C18 119.1(6) . . ? C14A C15 C18 119.8(5) . . ? C15 C16 C11 119.8(4) . . ? C15 C16 H16 120.1 . . ? C11 C16 H16 120.1 . . ? O2 C17 O1 120.7(4) . . ? O2 C17 C11 120.5(4) . . ? O1 C17 C11 118.8(3) . . ? O2 C17 Mn1 60.1(2) . . ? O1 C17 Mn1 60.7(2) . . ? C11 C17 Mn1 178.4(3) . . ? O3 C18 O4 123.7(3) . . ? O3 C18 C15 118.8(3) . . ? O4 C18 C15 117.5(3) . . ? C13A C12A C11 120.4(7) . . ? C13A C12A H12A 119.8 . . ? C11 C12A H12A 119.8 . . ? C13A C14A C15 121.5(7) . . ? C13A C14A H14A 119.2 . . ? C15 C14A H14A 119.2 . . ? O5A C13A C14A 124.1(7) . . ? O5A C13A C12A 117.1(6) . . ? C14A C13A C12A 118.8(7) . . ? C13A O5A H5A 109.5 . . ? OWA OWA OW2 132.3(9) 2_557 . ? C13B C12B C11 119.7(12) . . ? C13B C12B H12B 120.2 . . ? C11 C12B H12B 120.2 . . ? C13B C14B C15 120.6(11) . . ? C13B C14B H14B 119.7 . . ? C15 C14B H14B 119.7 . . ? C12B C13B C14B 119.9(12) . . ? C12B C13B O5B 120.0(11) . . ? C14B C13B O5B 120.0(11) . . ? C13B O5B H5B 109.5 . . ? C5A C4A C3 119.1(8) . . ? C5A C4A H4A 120.4 . . ? C3 C4A H4A 120.4 . . ? C4A C5A N1 122.3(8) . . ? C4A C5A H5A1 118.9 . . ? N1 C5A H5A1 118.9 . . ? C3 C2A C1A 120.6(8) . . ? C3 C2A H2A 119.7 . . ? C1A C2A H2A 119.7 . . ? N1 C1A C2A 124.1(8) . . ? N1 C1A H1A 118.0 . . ? C2A C1A H1A 118.0 . . ? C3 C4B C5B 119.8(11) . . ? C3 C4B H4B 120.1 . . ? C5B C4B H4B 120.1 . . ? N1 C5B C4B 127.0(12) . . ? N1 C5B H5B1 116.5 . . ? C4B C5B H5B1 116.5 . . ? C3 C2B C1B 119.0(11) . . ? C3 C2B H2B 120.5 . . ? C1B C2B H2B 120.5 . . ? N1 C1B C2B 120.6(11) . . ? N1 C1B H1B 119.7 . . ? C2B C1B H1B 119.7 . . ? OW2 OW1 OW1 131.7(13) . 2_557 ? OW3 OW2 OW1 126(4) . . ? OW3 OW2 OWA 139(3) . . ? OW1 OW2 OWA 95(2) . . ? OW2 OW3 OW5 136(7) . . ? OW2 OW3 OW5 138(7) . 3_577 ? OW5 OW3 OW5 86(2) . 3_577 ? OW3 OW5 OW3 94(2) . 3_577 ? OW3 OW5 OW4 87(2) . 3_577 ? OW3 OW5 OW4 82(2) 3_577 3_577 ? 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 Mn1 N1 C5B -162.5(7) 2_556 . . . ? O4 Mn1 N1 C5B -37.7(7) 1_655 . . . ? N2 Mn1 N1 C5B -107.7(14) . . . . ? O2 Mn1 N1 C5B 52.2(7) . . . . ? O1 Mn1 N1 C5B 107.6(7) . . . . ? C17 Mn1 N1 C5B 79.9(7) . . . . ? O3 Mn1 N1 C1A 66.7(6) 2_556 . . . ? O4 Mn1 N1 C1A -168.5(6) 1_655 . . . ? N2 Mn1 N1 C1A 121.5(13) . . . . ? O2 Mn1 N1 C1A -78.6(6) . . . . ? O1 Mn1 N1 C1A -23.2(6) . . . . ? C17 Mn1 N1 C1A -50.9(6) . . . . ? O3 Mn1 N1 C5A -118.0(5) 2_556 . . . ? O4 Mn1 N1 C5A 6.8(5) 1_655 . . . ? N2 Mn1 N1 C5A -63.2(14) . . . . ? O2 Mn1 N1 C5A 96.7(5) . . . . ? O1 Mn1 N1 C5A 152.1(5) . . . . ? C17 Mn1 N1 C5A 124.4(5) . . . . ? O3 Mn1 N1 C1B 16.5(7) 2_556 . . . ? O4 Mn1 N1 C1B 141.4(7) 1_655 . . . ? N2 Mn1 N1 C1B 71.4(14) . . . . ? O2 Mn1 N1 C1B -128.7(7) . . . . ? O1 Mn1 N1 C1B -73.3(7) . . . . ? C17 Mn1 N1 C1B -101.0(7) . . . . ? O3 Mn1 N2 C6 -38.6(3) 2_556 . . . ? O4 Mn1 N2 C6 -163.4(3) 1_655 . . . ? O2 Mn1 N2 C6 107.0(3) . . . . ? N1 Mn1 N2 C6 -93.4(12) . . . . ? O1 Mn1 N2 C6 51.7(3) . . . . ? C17 Mn1 N2 C6 79.0(3) . . . . ? O3 Mn1 N2 C10 146.3(3) 2_556 . . . ? O4 Mn1 N2 C10 21.5(3) 1_655 . . . ? O2 Mn1 N2 C10 -68.1(3) . . . . ? N1 Mn1 N2 C10 91.5(12) . . . . ? O1 Mn1 N2 C10 -123.4(3) . . . . ? C17 Mn1 N2 C10 -96.1(3) . . . . ? O3 Mn1 O1 C17 -166.6(2) 2_556 . . . ? O4 Mn1 O1 C17 22.3(3) 1_655 . . . ? N2 Mn1 O1 C17 104.4(2) . . . . ? O2 Mn1 O1 C17 1.7(2) . . . . ? N1 Mn1 O1 C17 -78.9(2) . . . . ? O3 Mn1 O2 C17 19.0(3) 2_556 . . . ? O4 Mn1 O2 C17 -169.9(2) 1_655 . . . ? N2 Mn1 O2 C17 -81.2(2) . . . . ? N1 Mn1 O2 C17 100.8(2) . . . . ? O1 Mn1 O2 C17 -1.7(2) . . . . ? C10 N2 C6 C7 0.2(6) . . . . ? Mn1 N2 C6 C7 -175.2(3) . . . . ? N2 C6 C7 C8 -0.3(6) . . . . ? C6 C7 C8 C9 0.1(6) . . . . ? C6 C7 C8 C3 179.3(4) . . . 1_545 ? C7 C8 C9 C10 0.0(6) . . . . ? C3 C8 C9 C10 -179.2(4) 1_545 . . . ? C6 N2 C10 C9 -0.1(6) . . . . ? Mn1 N2 C10 C9 175.2(3) . . . . ? C8 C9 C10 N2 0.0(6) . . . . ? C14B C15 C16 C11 21.1(7) . . . . ? C14A C15 C16 C11 -13.7(6) . . . . ? C18 C15 C16 C11 179.2(3) . . . . ? C12B C11 C16 C15 -21.9(8) . . . . ? C12A C11 C16 C15 11.9(6) . . . . ? C17 C11 C16 C15 178.6(3) . . . . ? Mn1 O2 C17 O1 3.0(4) . . . . ? Mn1 O2 C17 C11 -178.3(3) . . . . ? Mn1 O1 C17 O2 -3.0(4) . . . . ? Mn1 O1 C17 C11 178.3(3) . . . . ? C16 C11 C17 O2 167.2(4) . . . . ? C12B C11 C17 O2 7.3(8) . . . . ? C12A C11 C17 O2 -26.0(6) . . . . ? C16 C11 C17 O1 -14.1(6) . . . . ? C12B C11 C17 O1 -173.9(6) . . . . ? C12A C11 C17 O1 152.8(4) . . . . ? C16 C11 C17 Mn1 57(11) . . . . ? C12B C11 C17 Mn1 -103(11) . . . . ? C12A C11 C17 Mn1 -137(11) . . . . ? O3 Mn1 C17 O2 -167.8(2) 2_556 . . . ? O4 Mn1 C17 O2 11.4(3) 1_655 . . . ? N2 Mn1 C17 O2 101.7(2) . . . . ? N1 Mn1 C17 O2 -79.1(2) . . . . ? O1 Mn1 C17 O2 177.1(4) . . . . ? O3 Mn1 C17 O1 15.1(3) 2_556 . . . ? O4 Mn1 C17 O1 -165.6(2) 1_655 . . . ? N2 Mn1 C17 O1 -75.4(2) . . . . ? O2 Mn1 C17 O1 -177.1(4) . . . . ? N1 Mn1 C17 O1 103.9(2) . . . . ? O3 Mn1 C17 C11 -56(11) 2_556 . . . ? O4 Mn1 C17 C11 123(11) 1_655 . . . ? N2 Mn1 C17 C11 -147(11) . . . . ? O2 Mn1 C17 C11 111(11) . . . . ? N1 Mn1 C17 C11 32(11) . . . . ? O1 Mn1 C17 C11 -71(11) . . . . ? Mn1 O3 C18 O4 -5(5) 2_556 . . . ? Mn1 O3 C18 C15 175(4) 2_556 . . . ? Mn1 O4 C18 O3 1.8(4) 1_455 . . . ? Mn1 O4 C18 C15 -178.0(2) 1_455 . . . ? C16 C15 C18 O3 1.7(5) . . . . ? C14B C15 C18 O3 159.3(6) . . . . ? C14A C15 C18 O3 -165.2(4) . . . . ? C16 C15 C18 O4 -178.4(3) . . . . ? C14B C15 C18 O4 -20.9(7) . . . . ? C14A C15 C18 O4 14.6(6) . . . . ? C16 C11 C12A C13A -6.7(8) . . . . ? C12B C11 C12A C13A 90.7(18) . . . . ? C17 C11 C12A C13A -173.7(5) . . . . ? C16 C15 C14A C13A 10.6(8) . . . . ? C14B C15 C14A C13A -84.5(15) . . . . ? C18 C15 C14A C13A 177.8(5) . . . . ? C15 C14A C13A O5A 175.2(6) . . . . ? C15 C14A C13A C12A -5.5(10) . . . . ? C11 C12A C13A O5A -177.2(5) . . . . ? C11 C12A C13A C14A 3.4(10) . . . . ? C16 C11 C12B C13B 16.2(13) . . . . ? C12A C11 C12B C13B -83.3(19) . . . . ? C17 C11 C12B C13B 176.4(9) . . . . ? C16 C15 C14B C13B -15.3(12) . . . . ? C14A C15 C14B C13B 86.3(16) . . . . ? C18 C15 C14B C13B -173.6(8) . . . . ? C11 C12B C13B C14B -10.4(17) . . . . ? C11 C12B C13B O5B 171.9(9) . . . . ? C15 C14B C13B C12B 10.1(17) . . . . ? C15 C14B C13B O5B -172.1(9) . . . . ? C4B C3 C4A C5A 74.8(12) . . . . ? C2A C3 C4A C5A 2.7(11) . . . . ? C2B C3 C4A C5A -39.9(10) . . . . ? C8 C3 C4A C5A -178.4(7) 1_565 . . . ? C3 C4A C5A N1 -1.8(13) . . . . ? C5B N1 C5A C4A -72.9(14) . . . . ? C1A N1 C5A C4A -1.0(12) . . . . ? C1B N1 C5A C4A 41.9(11) . . . . ? Mn1 N1 C5A C4A -176.6(7) . . . . ? C4B C3 C2A C1A -37.2(11) . . . . ? C2B C3 C2A C1A 82.0(12) . . . . ? C4A C3 C2A C1A -1.0(12) . . . . ? C8 C3 C2A C1A -179.8(7) 1_565 . . . ? C5B N1 C1A C2A 39.2(12) . . . . ? C5A N1 C1A C2A 2.9(13) . . . . ? C1B N1 C1A C2A -78.1(13) . . . . ? Mn1 N1 C1A C2A 178.4(7) . . . . ? C3 C2A C1A N1 -1.9(15) . . . . ? C2A C3 C4B C5B 38.6(11) . . . . ? C2B C3 C4B C5B -1.5(13) . . . . ? C4A C3 C4B C5B -81.7(13) . . . . ? C8 C3 C4B C5B -178.6(8) 1_565 . . . ? C1A N1 C5B C4B -38.8(14) . . . . ? C5A N1 C5B C4B 81.5(17) . . . . ? C1B N1 C5B C4B 2.6(16) . . . . ? Mn1 N1 C5B C4B -178.3(9) . . . . ? C3 C4B C5B N1 -0.4(18) . . . . ? C4B C3 C2B C1B 1.1(13) . . . . ? C2A C3 C2B C1B -73.7(13) . . . . ? C4A C3 C2B C1B 39.6(12) . . . . ? C8 C3 C2B C1B 178.3(8) 1_565 . . . ? C5B N1 C1B C2B -2.9(14) . . . . ? C1A N1 C1B C2B 73.4(13) . . . . ? C5A N1 C1B C2B -41.2(12) . . . . ? Mn1 N1 C1B C2B 178.0(8) . . . . ? C3 C2B C1B N1 1.2(16) . . . . ? OW1 OW1 OW2 OW3 -162(5) 2_557 . . . ? OW1 OW1 OW2 OWA 12(3) 2_557 . . . ? OWA OWA OW2 OW3 164(7) 2_557 . . . ? OWA OWA OW2 OW1 -9(3) 2_557 . . . ? OW1 OW2 OW3 OW5 47(8) . . . . ? OWA OW2 OW3 OW5 -125(5) . . . . ? OW1 OW2 OW3 OW5 -138(5) . . . 3_577 ? OWA OW2 OW3 OW5 50(11) . . . 3_577 ? OW2 OW3 OW5 OW3 177(8) . . . 3_577 ? OW5 OW3 OW5 OW3 0.000(1) 3_577 . . 3_577 ? OW2 OW3 OW5 OW4 95(7) . . . 3_577 ? OW5 OW3 OW5 OW4 -81.6(18) 3_577 . . 3_577 ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 26.91 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.698 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.088 #===END data_yeltestm _database_code_depnum_ccdc_archive 'CCDC 657327' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20.50 H18 Mn N2.50 O7' _chemical_formula_weight 466.31 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 11.6900(8) _cell_length_b 10.1772(7) _cell_length_c 17.9098(12) _cell_angle_alpha 90.00 _cell_angle_beta 102.326(2) _cell_angle_gamma 90.00 _cell_volume 2081.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 958 _exptl_absorpt_coefficient_mu 0.681 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2766 _exptl_absorpt_correction_T_max 0.3058 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16826 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.0519 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 26.73 _reflns_number_total 4239 _reflns_number_gt 2770 _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^)+(0.1250P)^2^+4.5000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4239 _refine_ls_number_parameters 327 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.1040 _refine_ls_R_factor_gt 0.0728 _refine_ls_wR_factor_ref 0.2428 _refine_ls_wR_factor_gt 0.2284 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.093 _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 Mn1 Mn 0.46478(7) 0.34742(7) 0.42333(4) 0.0319(3) Uani 1 1 d . . . N1 N 0.6606(4) 0.3521(5) 0.4208(3) 0.0422(11) Uani 1 1 d D . . C1 C 0.7413(5) 0.3102(7) 0.4792(4) 0.0524(16) Uani 1 1 d D . . H1 H 0.7168 0.2814 0.5225 0.063 Uiso 1 1 calc R . . C2 C 0.8584(5) 0.3065(7) 0.4801(4) 0.0515(16) Uani 1 1 d D . . H2 H 0.9107 0.2749 0.5230 0.062 Uiso 1 1 calc R . . C3 C 0.8989(5) 0.3493(5) 0.4181(3) 0.0397(13) Uani 1 1 d D . . C4 C 0.8170(6) 0.3979(9) 0.3579(4) 0.072(2) Uani 1 1 d D . . H4 H 0.8403 0.4324 0.3154 0.086 Uiso 1 1 calc R . . C5 C 0.7000(6) 0.3953(9) 0.3608(4) 0.070(2) Uani 1 1 d D . . H5 H 0.6457 0.4253 0.3185 0.084 Uiso 1 1 calc R . . N2 N 0.2684(4) 0.3551(4) 0.4219(3) 0.0398(11) Uani 1 1 d . . . C10 C 0.1888(6) 0.3550(8) 0.3569(4) 0.0610(19) Uani 1 1 d . . . H10 H 0.2152 0.3561 0.3114 0.073 Uiso 1 1 calc R . . C9 C 0.0713(6) 0.3534(8) 0.3524(4) 0.065(2) Uani 1 1 d . . . H9 H 0.0202 0.3530 0.3048 0.078 Uiso 1 1 calc R . . C8 C 0.0271(5) 0.3522(5) 0.4183(3) 0.0403(13) Uani 1 1 d . . . C7 C 0.1099(6) 0.3476(6) 0.4874(4) 0.0509(15) Uani 1 1 d . . . H7 H 0.0859 0.3425 0.5336 0.061 Uiso 1 1 calc R . . C6 C 0.2265(5) 0.3506(6) 0.4861(4) 0.0474(14) Uani 1 1 d . . . H6 H 0.2801 0.3495 0.5327 0.057 Uiso 1 1 calc R . . O1 O 0.4561(4) 0.1296(4) 0.4289(2) 0.0478(11) Uani 1 1 d . . . O2 O 0.4300(4) 0.2167(4) 0.3153(2) 0.0493(11) Uani 1 1 d . . . O3 O 0.4904(4) -0.3596(4) 0.4563(2) 0.0475(10) Uani 1 1 d . . . O4 O 0.4433(4) -0.4826(3) 0.3529(2) 0.0452(10) Uani 1 1 d . . . O5 O 0.3566(6) -0.1741(5) 0.1353(3) 0.090(2) Uani 1 1 d . . . H5A H 0.3451 -0.1029 0.1135 0.135 Uiso 1 1 calc R . . C11 C 0.4232(6) -0.0175(5) 0.3235(3) 0.0415(13) Uani 1 1 d . . . C12 C 0.3923(6) -0.0302(6) 0.2447(3) 0.0511(16) Uani 1 1 d . . . H12 H 0.3770 0.0440 0.2139 0.061 Uiso 1 1 calc R . . C13 C 0.3843(7) -0.1547(6) 0.2122(3) 0.0583(19) Uani 1 1 d . . . C14 C 0.4046(6) -0.2640(5) 0.2579(3) 0.0493(15) Uani 1 1 d . . . H14 H 0.3987 -0.3470 0.2357 0.059 Uiso 1 1 calc R . . C15 C 0.4337(5) -0.2525(5) 0.3370(3) 0.0347(12) Uani 1 1 d . . . C16 C 0.4421(5) -0.1271(5) 0.3699(3) 0.0362(12) Uani 1 1 d . . . H16 H 0.4603 -0.1178 0.4227 0.043 Uiso 1 1 calc R . . C17 C 0.4362(5) 0.1180(5) 0.3572(3) 0.0371(12) Uani 1 1 d . . . C18 C 0.4571(5) -0.3737(5) 0.3862(3) 0.0343(12) Uani 1 1 d . . . N3 N 0.7332(12) -0.0450(15) 0.4117(7) 0.099(6) Uani 0.50 1 d PD A 1 C21 C 0.7570(12) -0.0268(14) 0.4886(8) 0.057(4) Uani 0.50 1 d PD A 1 H21 H 0.6964 -0.0283 0.5148 0.069 Uiso 0.50 1 calc PR A 1 C22 C 0.8654(11) -0.0072(11) 0.5264(6) 0.051(3) Uani 0.50 1 d PD A 1 H22 H 0.8851 0.0019 0.5793 0.061 Uiso 0.50 1 calc PR A 1 C23 C 0.9427(8) -0.0015(11) 0.4838(7) 0.073(5) Uani 0.50 1 d PD . 1 C24 C 0.9289(11) -0.0108(14) 0.4076(7) 0.060(3) Uani 0.50 1 d PD A 1 H24 H 0.9898 -0.0016 0.3820 0.071 Uiso 0.50 1 calc PR A 1 C25 C 0.8124(10) -0.0359(13) 0.3710(7) 0.039(3) Uani 0.50 1 d PDU A 1 H25 H 0.7922 -0.0459 0.3182 0.047 Uiso 0.50 1 calc PR A 1 OW1 O 0.7568(10) -0.0250(9) 0.5372(6) 0.065(3) Uani 0.50 1 d P B 2 OW2 O 0.7877(11) -0.087(3) 0.2698(10) 0.200(11) Uani 0.50 1 d PU . 2 OW3 O 0.6698(14) 0.0358(19) 0.2626(11) 0.142(6) Uani 0.50 1 d P . 2 OW4 O 0.764(3) -0.041(3) 0.3589(12) 0.227(14) Uani 0.50 1 d PU C 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0360(5) 0.0272(4) 0.0323(5) 0.0002(3) 0.0070(3) 0.0008(3) N1 0.034(2) 0.052(3) 0.040(3) 0.000(2) 0.007(2) -0.001(2) C1 0.046(4) 0.064(4) 0.049(4) 0.022(3) 0.014(3) 0.008(3) C2 0.039(3) 0.068(4) 0.046(4) 0.022(3) 0.005(3) 0.007(3) C3 0.038(3) 0.044(3) 0.036(3) -0.004(2) 0.006(2) 0.001(2) C4 0.045(4) 0.134(7) 0.037(3) 0.025(4) 0.012(3) 0.008(4) C5 0.042(4) 0.133(7) 0.034(3) 0.021(4) 0.004(3) 0.013(4) N2 0.037(3) 0.042(3) 0.041(3) -0.001(2) 0.010(2) 0.000(2) C10 0.047(4) 0.104(6) 0.034(3) 0.004(3) 0.013(3) 0.006(4) C9 0.047(4) 0.112(6) 0.034(3) -0.006(4) 0.005(3) 0.005(4) C8 0.034(3) 0.044(3) 0.041(3) -0.002(2) 0.006(2) 0.001(2) C7 0.049(4) 0.067(4) 0.038(3) 0.004(3) 0.013(3) -0.006(3) C6 0.040(3) 0.061(4) 0.040(3) 0.003(3) 0.006(3) 0.002(3) O1 0.077(3) 0.031(2) 0.036(2) -0.0037(16) 0.013(2) -0.0008(18) O2 0.081(3) 0.0262(19) 0.040(2) 0.0022(17) 0.012(2) -0.0018(19) O3 0.063(3) 0.043(2) 0.034(2) 0.0067(17) 0.0046(19) 0.0084(19) O4 0.060(3) 0.0271(19) 0.047(2) 0.0017(17) 0.008(2) -0.0023(17) O5 0.192(7) 0.044(3) 0.027(2) -0.0014(19) 0.010(3) -0.006(3) C11 0.060(4) 0.029(3) 0.036(3) -0.001(2) 0.012(3) -0.003(2) C12 0.083(5) 0.034(3) 0.034(3) 0.003(2) 0.007(3) -0.004(3) C13 0.111(6) 0.036(3) 0.025(3) 0.002(2) 0.009(3) -0.004(3) C14 0.082(4) 0.029(3) 0.034(3) -0.004(2) 0.006(3) -0.004(3) C15 0.042(3) 0.030(3) 0.032(3) 0.004(2) 0.007(2) -0.003(2) C16 0.049(3) 0.030(3) 0.029(3) -0.003(2) 0.006(2) -0.001(2) C17 0.044(3) 0.030(3) 0.036(3) -0.002(2) 0.006(2) -0.002(2) C18 0.031(3) 0.035(3) 0.038(3) 0.002(2) 0.009(2) 0.002(2) N3 0.086(11) 0.080(10) 0.104(13) 0.036(9) -0.038(10) -0.027(8) C21 0.071(10) 0.063(9) 0.043(8) -0.012(7) 0.021(8) -0.013(7) C22 0.085(10) 0.045(7) 0.025(6) -0.012(5) 0.019(7) -0.006(6) C23 0.113(14) 0.051(8) 0.047(9) -0.009(7) 0.003(9) -0.006(9) C24 0.056(8) 0.074(9) 0.052(8) -0.010(7) 0.019(6) 0.006(7) C25 0.031(6) 0.052(6) 0.023(6) -0.015(5) -0.019(5) 0.016(6) OW1 0.095(8) 0.059(6) 0.043(6) -0.022(5) 0.021(6) -0.030(5) OW2 0.049(8) 0.40(3) 0.135(14) 0.183(17) -0.016(7) 0.000(11) OW3 0.112(12) 0.137(14) 0.169(16) -0.013(12) 0.013(12) 0.032(10) OW4 0.25(3) 0.34(3) 0.095(15) -0.044(17) 0.047(17) -0.20(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O3 2.111(4) 3_656 ? Mn1 O4 2.124(4) 1_565 ? Mn1 O1 2.222(4) . ? Mn1 N2 2.292(5) . ? Mn1 N1 2.299(5) . ? Mn1 O2 2.311(4) . ? Mn1 C17 2.607(5) . ? N1 C1 1.321(7) . ? N1 C5 1.331(7) . ? C1 C2 1.367(8) . ? C1 H1 0.9300 . ? C2 C3 1.368(8) . ? C2 H2 0.9300 . ? C3 C4 1.372(8) . ? C3 C8 1.499(8) 1_655 ? C4 C5 1.381(9) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? N2 C10 1.327(8) . ? N2 C6 1.344(7) . ? C10 C9 1.359(10) . ? C10 H10 0.9300 . ? C9 C8 1.385(9) . ? C9 H9 0.9300 . ? C8 C7 1.401(9) . ? C8 C3 1.499(8) 1_455 ? C7 C6 1.368(9) . ? C7 H7 0.9300 . ? C6 H6 0.9300 . ? O1 C17 1.260(6) . ? O2 C17 1.246(7) . ? O3 C18 1.241(7) . ? O3 Mn1 2.111(4) 3_656 ? O4 C18 1.252(6) . ? O4 Mn1 2.124(4) 1_545 ? O5 C13 1.360(7) . ? O5 H5A 0.8200 . ? C11 C16 1.380(7) . ? C11 C12 1.386(8) . ? C11 C17 1.500(7) . ? C12 C13 1.390(8) . ? C12 H12 0.9300 . ? C13 C14 1.371(8) . ? C14 C15 1.389(8) . ? C14 H14 0.9300 . ? C15 C16 1.399(7) . ? C15 C18 1.506(7) . ? C16 H16 0.9300 . ? N3 C25 1.299(14) . ? N3 C21 1.359(13) . ? C21 C22 1.318(15) . ? C21 H21 0.9300 . ? C22 C23 1.303(14) . ? C22 H22 0.9300 . ? C23 C23 1.342(17) 3_756 ? C23 C24 1.343(14) . ? C24 C25 1.403(14) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? OW2 OW2 1.01(2) 2_655 ? OW2 OW3 1.50(2) 2_655 ? OW2 OW4 1.74(3) . ? OW3 OW2 1.50(2) 2_655 ? 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 Mn1 O4 122.03(15) 3_656 1_565 ? O3 Mn1 O1 90.98(14) 3_656 . ? O4 Mn1 O1 146.96(15) 1_565 . ? O3 Mn1 N2 92.21(17) 3_656 . ? O4 Mn1 N2 88.53(16) 1_565 . ? O1 Mn1 N2 88.83(16) . . ? O3 Mn1 N1 89.31(17) 3_656 . ? O4 Mn1 N1 87.91(17) 1_565 . ? O1 Mn1 N1 94.40(17) . . ? N2 Mn1 N1 176.41(17) . . ? O3 Mn1 O2 148.19(14) 3_656 . ? O4 Mn1 O2 89.69(14) 1_565 . ? O1 Mn1 O2 57.42(14) . . ? N2 Mn1 O2 90.80(16) . . ? N1 Mn1 O2 89.62(17) . . ? O3 Mn1 C17 119.78(16) 3_656 . ? O4 Mn1 C17 118.19(16) 1_565 . ? O1 Mn1 C17 28.86(15) . . ? N2 Mn1 C17 89.72(17) . . ? N1 Mn1 C17 92.35(17) . . ? O2 Mn1 C17 28.55(15) . . ? C1 N1 C5 115.7(5) . . ? C1 N1 Mn1 121.6(4) . . ? C5 N1 Mn1 122.7(4) . . ? N1 C1 C2 124.3(6) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C1 C2 C3 120.0(5) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C2 C3 C4 116.7(5) . . ? C2 C3 C8 121.6(5) . 1_655 ? C4 C3 C8 121.5(5) . 1_655 ? C3 C4 C5 119.6(6) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 123.6(6) . . ? N1 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? C10 N2 C6 115.9(5) . . ? C10 N2 Mn1 121.5(4) . . ? C6 N2 Mn1 122.5(4) . . ? N2 C10 C9 124.2(6) . . ? N2 C10 H10 117.9 . . ? C9 C10 H10 117.9 . . ? C10 C9 C8 120.4(6) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C8 C7 116.1(5) . . ? C9 C8 C3 123.6(5) . 1_455 ? C7 C8 C3 120.2(5) . 1_455 ? C6 C7 C8 119.2(6) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? N2 C6 C7 124.2(6) . . ? N2 C6 H6 117.9 . . ? C7 C6 H6 117.9 . . ? C17 O1 Mn1 92.8(3) . . ? C17 O2 Mn1 89.0(3) . . ? C18 O3 Mn1 174.9(4) . 3_656 ? C18 O4 Mn1 116.8(4) . 1_545 ? C13 O5 H5A 109.5 . . ? C16 C11 C12 120.7(5) . . ? C16 C11 C17 120.8(5) . . ? C12 C11 C17 118.5(5) . . ? C11 C12 C13 119.5(5) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? O5 C13 C14 117.5(5) . . ? O5 C13 C12 122.5(5) . . ? C14 C13 C12 120.1(5) . . ? C13 C14 C15 120.9(5) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C14 C15 C16 119.0(5) . . ? C14 C15 C18 120.1(5) . . ? C16 C15 C18 120.9(5) . . ? C11 C16 C15 119.8(5) . . ? C11 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? O2 C17 O1 120.8(5) . . ? O2 C17 C11 120.7(5) . . ? O1 C17 C11 118.5(5) . . ? O2 C17 Mn1 62.4(3) . . ? O1 C17 Mn1 58.4(3) . . ? C11 C17 Mn1 176.7(4) . . ? O3 C18 O4 124.3(5) . . ? O3 C18 C15 118.4(5) . . ? O4 C18 C15 117.2(5) . . ? C25 N3 C21 122.9(12) . . ? C22 C21 N3 120.5(12) . . ? C22 C21 H21 119.7 . . ? N3 C21 H21 119.7 . . ? C23 C22 C21 114.6(10) . . ? C23 C22 H22 122.7 . . ? C21 C22 H22 122.7 . . ? C22 C23 C23 120.1(15) . 3_756 ? C22 C23 C24 130.1(10) . . ? C23 C23 C24 109.4(14) 3_756 . ? C23 C24 C25 112.4(11) . . ? C23 C24 H24 123.8 . . ? C25 C24 H24 123.8 . . ? N3 C25 C24 119.2(11) . . ? N3 C25 H25 120.4 . . ? C24 C25 H25 120.4 . . ? OW2 OW2 OW3 92.3(15) 2_655 2_655 ? OW2 OW2 OW4 111(2) 2_655 . ? OW3 OW2 OW4 105(2) 2_655 . ? 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 Mn1 N1 C1 26.4(5) 3_656 . . . ? O4 Mn1 N1 C1 148.5(5) 1_565 . . . ? O1 Mn1 N1 C1 -64.5(5) . . . . ? N2 Mn1 N1 C1 141(3) . . . . ? O2 Mn1 N1 C1 -121.8(5) . . . . ? C17 Mn1 N1 C1 -93.3(5) . . . . ? O3 Mn1 N1 C5 -154.4(6) 3_656 . . . ? O4 Mn1 N1 C5 -32.3(6) 1_565 . . . ? O1 Mn1 N1 C5 114.7(6) . . . . ? N2 Mn1 N1 C5 -39(3) . . . . ? O2 Mn1 N1 C5 57.4(6) . . . . ? C17 Mn1 N1 C5 85.8(6) . . . . ? C5 N1 C1 C2 -1.5(10) . . . . ? Mn1 N1 C1 C2 177.7(5) . . . . ? N1 C1 C2 C3 0.7(11) . . . . ? C1 C2 C3 C4 1.7(10) . . . . ? C1 C2 C3 C8 177.3(6) . . . 1_655 ? C2 C3 C4 C5 -3.3(12) . . . . ? C8 C3 C4 C5 -178.9(7) 1_655 . . . ? C1 N1 C5 C4 -0.2(12) . . . . ? Mn1 N1 C5 C4 -179.4(7) . . . . ? C3 C4 C5 N1 2.7(14) . . . . ? O3 Mn1 N2 C10 177.8(5) 3_656 . . . ? O4 Mn1 N2 C10 55.8(5) 1_565 . . . ? O1 Mn1 N2 C10 -91.3(5) . . . . ? N1 Mn1 N2 C10 63(3) . . . . ? O2 Mn1 N2 C10 -33.9(5) . . . . ? C17 Mn1 N2 C10 -62.4(5) . . . . ? O3 Mn1 N2 C6 -7.0(4) 3_656 . . . ? O4 Mn1 N2 C6 -129.0(4) 1_565 . . . ? O1 Mn1 N2 C6 83.9(4) . . . . ? N1 Mn1 N2 C6 -122(3) . . . . ? O2 Mn1 N2 C6 141.3(4) . . . . ? C17 Mn1 N2 C6 112.8(4) . . . . ? C6 N2 C10 C9 1.4(10) . . . . ? Mn1 N2 C10 C9 176.9(6) . . . . ? N2 C10 C9 C8 0.2(12) . . . . ? C10 C9 C8 C7 -2.4(10) . . . . ? C10 C9 C8 C3 -179.5(6) . . . 1_455 ? C9 C8 C7 C6 3.0(9) . . . . ? C3 C8 C7 C6 -179.9(5) 1_455 . . . ? C10 N2 C6 C7 -0.8(9) . . . . ? Mn1 N2 C6 C7 -176.2(5) . . . . ? C8 C7 C6 N2 -1.4(10) . . . . ? O3 Mn1 O1 C17 -176.3(4) 3_656 . . . ? O4 Mn1 O1 C17 6.0(5) 1_565 . . . ? N2 Mn1 O1 C17 91.5(4) . . . . ? N1 Mn1 O1 C17 -86.9(4) . . . . ? O2 Mn1 O1 C17 -0.2(3) . . . . ? O3 Mn1 O2 C17 7.6(5) 3_656 . . . ? O4 Mn1 O2 C17 -176.5(3) 1_565 . . . ? O1 Mn1 O2 C17 0.2(3) . . . . ? N2 Mn1 O2 C17 -87.9(4) . . . . ? N1 Mn1 O2 C17 95.6(4) . . . . ? C16 C11 C12 C13 -2.2(11) . . . . ? C17 C11 C12 C13 177.4(6) . . . . ? C11 C12 C13 O5 -178.7(7) . . . . ? C11 C12 C13 C14 1.3(12) . . . . ? O5 C13 C14 C15 179.8(7) . . . . ? C12 C13 C14 C15 -0.3(12) . . . . ? C13 C14 C15 C16 0.1(10) . . . . ? C13 C14 C15 C18 -179.2(6) . . . . ? C12 C11 C16 C15 2.1(10) . . . . ? C17 C11 C16 C15 -177.6(5) . . . . ? C14 C15 C16 C11 -1.0(9) . . . . ? C18 C15 C16 C11 178.3(5) . . . . ? Mn1 O2 C17 O1 -0.3(6) . . . . ? Mn1 O2 C17 C11 -178.8(5) . . . . ? Mn1 O1 C17 O2 0.3(6) . . . . ? Mn1 O1 C17 C11 178.8(5) . . . . ? C16 C11 C17 O2 173.2(6) . . . . ? C12 C11 C17 O2 -6.5(9) . . . . ? C16 C11 C17 O1 -5.3(9) . . . . ? C12 C11 C17 O1 175.0(6) . . . . ? C16 C11 C17 Mn1 12(8) . . . . ? C12 C11 C17 Mn1 -167(7) . . . . ? O3 Mn1 C17 O2 -175.4(3) 3_656 . . . ? O4 Mn1 C17 O2 4.0(4) 1_565 . . . ? O1 Mn1 C17 O2 -179.7(6) . . . . ? N2 Mn1 C17 O2 92.2(4) . . . . ? N1 Mn1 C17 O2 -84.9(4) . . . . ? O3 Mn1 C17 O1 4.3(4) 3_656 . . . ? O4 Mn1 C17 O1 -176.3(3) 1_565 . . . ? N2 Mn1 C17 O1 -88.1(4) . . . . ? N1 Mn1 C17 O1 94.9(4) . . . . ? O2 Mn1 C17 O1 179.7(6) . . . . ? O3 Mn1 C17 C11 -14(7) 3_656 . . . ? O4 Mn1 C17 C11 165(7) 1_565 . . . ? O1 Mn1 C17 C11 -18(7) . . . . ? N2 Mn1 C17 C11 -106(7) . . . . ? N1 Mn1 C17 C11 77(7) . . . . ? O2 Mn1 C17 C11 161(8) . . . . ? Mn1 O3 C18 O4 -52(5) 3_656 . . . ? Mn1 O3 C18 C15 129(4) 3_656 . . . ? Mn1 O4 C18 O3 5.5(8) 1_545 . . . ? Mn1 O4 C18 C15 -175.8(3) 1_545 . . . ? C14 C15 C18 O3 175.3(6) . . . . ? C16 C15 C18 O3 -4.0(8) . . . . ? C14 C15 C18 O4 -3.5(8) . . . . ? C16 C15 C18 O4 177.2(5) . . . . ? C25 N3 C21 C22 -5(2) . . . . ? N3 C21 C22 C23 3(2) . . . . ? C21 C22 C23 C23 -171.5(15) . . . 3_756 ? C21 C22 C23 C24 1(2) . . . . ? C22 C23 C24 C25 -2.9(19) . . . . ? C23 C23 C24 C25 170.2(14) 3_756 . . . ? C21 N3 C25 C24 2(2) . . . . ? C23 C24 C25 N3 1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 26.73 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 1.234 _refine_diff_density_min -0.616 _refine_diff_density_rms 0.107 #===END data_niblueam _database_code_depnum_ccdc_archive 'CCDC 657328' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 N2 Ni O6' _chemical_formula_weight 413.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 11.2217(7) _cell_length_b 11.2217(7) _cell_length_c 25.0290(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2729.6(3) _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 Pyramid _exptl_crystal_colour Blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 1.103 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15724 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.68 _reflns_number_total 3553 _reflns_number_gt 3057 _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^)+(0.0691P)^2^+1.5051P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(2) _refine_ls_number_reflns 3553 _refine_ls_number_parameters 257 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1193 _refine_ls_wR_factor_gt 0.1137 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.054 _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 Ni1 Ni 0.97636(5) 0.58381(5) 0.10331(2) 0.02551(15) Uani 1 1 d . . . C3 C 0.9835(5) 1.0210(5) 0.0986(2) 0.0396(11) Uani 1 1 d . . . O2 O 0.3722(3) 0.4655(3) 0.36255(14) 0.0365(8) Uani 1 1 d . . . N2 N 0.9750(4) 0.3988(4) 0.1036(2) 0.0355(9) Uani 1 1 d . . . O1 O 1.1072(4) 0.6388(4) 0.16742(17) 0.0431(9) Uani 1 1 d D . . O5 O 0.8064(3) 0.5108(3) 0.14801(13) 0.0351(7) Uani 1 1 d . . . O3 O 0.4770(3) 0.3446(3) 0.36556(12) 0.0330(7) Uani 1 1 d . . . C7 C 1.0969(5) 0.2751(5) 0.0987(4) 0.072(2) Uani 1 1 d . . . H7 H 1.1818 0.2796 0.0965 0.086 Uiso 1 1 calc R . . N1 N 0.9858(4) 0.7733(3) 0.09975(19) 0.0342(8) Uani 1 1 d . . . C17 C 0.4392(4) 0.4178(4) 0.33932(19) 0.0297(10) Uani 1 1 d . . . C12 C 0.4118(5) 0.4850(5) 0.2471(2) 0.0348(10) Uani 1 1 d . . . H12 H 0.3341 0.4874 0.2584 0.042 Uiso 1 1 calc R . . C9 C 0.8592(5) 0.1566(5) 0.1010(5) 0.083(2) Uani 1 1 d . . . H9 H 0.7750 0.0751 0.1013 0.099 Uiso 1 1 calc R . . O6 O 0.3795(4) 0.5416(5) 0.15998(17) 0.0557(11) Uani 1 1 d D . . C13 C 0.4543(5) 0.5132(5) 0.1942(2) 0.0388(11) Uani 1 1 d . . . C15 C 0.6494(5) 0.4848(5) 0.21500(18) 0.0320(10) Uani 1 1 d . . . O4 O 0.8676(4) 0.5020(5) 0.23121(16) 0.0571(10) Uani 1 1 d . . . C11 C 0.4862(5) 0.4530(5) 0.28320(19) 0.0334(10) Uani 1 1 d . . . C2 C 1.1019(6) 1.0172(5) 0.0980(5) 0.088(3) Uani 1 1 d . . . H2 H 1.1861 1.0986 0.0971 0.106 Uiso 1 1 calc R . . C5 C 0.8686(5) 0.7766(5) 0.0983(3) 0.0615(18) Uani 1 1 d . . . H5 H 0.7860 0.6935 0.0972 0.074 Uiso 1 1 calc R . . C4 C 0.8636(5) 0.8960(5) 0.0984(4) 0.0615(18) Uani 1 1 d . . . H4 H 0.7791 0.8925 0.0984 0.074 Uiso 1 1 calc R . . C10 C 0.8607(5) 0.2789(5) 0.1024(4) 0.074(2) Uani 1 1 d . . . H10 H 0.7771 0.2774 0.1025 0.089 Uiso 1 1 calc R . . C14 C 0.5720(5) 0.5103(5) 0.1788(2) 0.0383(11) Uani 1 1 d . . . H14 H 0.5992 0.5259 0.1432 0.046 Uiso 1 1 calc R . . C18 C 0.7851(5) 0.4973(5) 0.19685(19) 0.0357(10) Uani 1 1 d . . . C8 C 0.9783(5) 0.1502(5) 0.0992(3) 0.0441(12) Uani 1 1 d . . . C16 C 0.6037(5) 0.4533(5) 0.2674(2) 0.0351(9) Uani 1 1 d . . . H16 H 0.6528 0.4322 0.2919 0.042 Uiso 1 1 calc R . . C6 C 1.0900(6) 0.3969(5) 0.1015(4) 0.073(2) Uani 1 1 d . . . H6 H 1.1721 0.4806 0.1018 0.088 Uiso 1 1 calc R . . C1 C 1.0976(6) 0.8921(6) 0.0989(4) 0.073(2) Uani 1 1 d . . . H1 H 1.1810 0.8931 0.0989 0.088 Uiso 1 1 calc R . . H21 H 0.417(5) 0.570(5) 0.1329(16) 0.037(16) Uiso 1 1 d D . . HW1 H 1.065(5) 0.611(5) 0.1934(18) 0.036(11) Uiso 1 1 d D . . HW2 H 1.186(3) 0.671(5) 0.169(2) 0.036(11) Uiso 1 1 d 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 Ni1 0.0305(3) 0.0248(3) 0.0238(3) -0.0029(2) -0.0022(2) 0.0157(2) C3 0.042(3) 0.027(2) 0.052(3) -0.007(2) -0.004(2) 0.0193(18) O2 0.0431(19) 0.0439(18) 0.0302(19) 0.0048(14) 0.0053(14) 0.0273(16) N2 0.0318(18) 0.0263(18) 0.049(2) -0.0080(19) -0.008(2) 0.0150(15) O1 0.039(2) 0.040(2) 0.040(2) -0.0007(17) -0.0093(18) 0.0124(18) O5 0.0410(18) 0.0438(18) 0.0235(17) 0.0043(13) 0.0049(13) 0.0234(15) O3 0.0441(18) 0.0372(17) 0.0231(17) 0.0017(13) 0.0024(14) 0.0243(15) C7 0.037(3) 0.031(3) 0.158(7) -0.007(4) -0.014(4) 0.027(2) N1 0.0389(19) 0.0316(19) 0.039(2) 0.0023(18) 0.0008(19) 0.0230(16) C17 0.034(2) 0.028(2) 0.024(2) -0.0013(17) 0.0006(18) 0.0136(18) C12 0.034(2) 0.038(3) 0.033(3) 0.0060(19) 0.0029(19) 0.019(2) C9 0.033(3) 0.025(2) 0.187(8) -0.004(4) -0.008(4) 0.012(2) O6 0.052(2) 0.089(3) 0.037(2) 0.024(2) 0.0049(19) 0.043(2) C13 0.042(3) 0.045(3) 0.033(3) 0.006(2) 0.000(2) 0.023(2) C15 0.034(2) 0.039(2) 0.025(2) 0.0022(18) 0.0017(18) 0.020(2) O4 0.047(2) 0.101(3) 0.033(2) 0.011(2) 0.0037(17) 0.044(2) C11 0.033(2) 0.030(2) 0.034(3) 0.0016(18) -0.0009(19) 0.0134(19) C2 0.029(3) 0.021(2) 0.207(10) -0.002(4) 0.000(4) 0.007(2) C5 0.037(3) 0.029(2) 0.119(6) -0.007(3) -0.007(3) 0.016(2) C4 0.032(3) 0.035(3) 0.122(6) -0.001(4) -0.002(3) 0.020(2) C10 0.036(3) 0.035(3) 0.156(7) -0.003(4) 0.001(4) 0.021(2) C14 0.040(3) 0.049(3) 0.026(3) 0.007(2) 0.004(2) 0.022(2) C18 0.037(2) 0.041(3) 0.029(3) 0.002(2) 0.000(2) 0.020(2) C8 0.036(2) 0.030(2) 0.071(4) -0.003(3) -0.005(3) 0.020(2) C16 0.039(2) 0.044(2) 0.027(2) 0.006(2) 0.001(2) 0.025(2) C6 0.038(3) 0.031(3) 0.155(7) -0.011(4) -0.015(4) 0.021(2) C1 0.042(3) 0.041(3) 0.147(7) -0.006(4) -0.001(4) 0.028(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O5 2.000(3) . ? Ni1 O1 2.050(4) . ? Ni1 N2 2.068(3) . ? Ni1 O3 2.071(3) 3_664 ? Ni1 N1 2.077(3) . ? Ni1 O2 2.181(3) 3_664 ? Ni1 C17 2.451(5) 3_664 ? C3 C2 1.351(7) . ? C3 C4 1.375(7) . ? C3 C8 1.480(6) 1_565 ? O2 C17 1.262(5) . ? O2 Ni1 2.181(3) 2_655 ? N2 C6 1.302(7) . ? N2 C10 1.316(6) . ? O1 HW1 0.77(3) . ? O1 HW2 0.77(3) . ? O5 C18 1.240(6) . ? O3 C17 1.278(6) . ? O3 Ni1 2.071(3) 2_655 ? C7 C8 1.368(7) . ? C7 C6 1.409(7) . ? C7 H7 0.9300 . ? N1 C1 1.296(7) . ? N1 C5 1.335(6) . ? C17 C11 1.483(7) . ? C17 Ni1 2.451(5) 2_655 ? C12 C13 1.390(7) . ? C12 C11 1.393(6) . ? C12 H12 0.9300 . ? C9 C10 1.364(7) . ? C9 C8 1.375(7) . ? C9 H9 0.9300 . ? O6 C13 1.345(6) . ? O6 H21 0.78(3) . ? C13 C14 1.392(7) . ? C15 C14 1.381(7) . ? C15 C16 1.388(7) . ? C15 C18 1.527(7) . ? O4 C18 1.245(6) . ? C11 C16 1.376(6) . ? C2 C1 1.380(7) . ? C2 H2 0.9300 . ? C5 C4 1.368(7) . ? C5 H5 0.9300 . ? C4 H4 0.9300 . ? C10 H10 0.9300 . ? C14 H14 0.9300 . ? C8 C3 1.480(6) 1_545 ? C16 H16 0.9300 . ? C6 H6 0.9300 . ? C1 H1 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 O5 Ni1 O1 94.48(15) . . ? O5 Ni1 N2 93.41(16) . . ? O1 Ni1 N2 86.78(17) . . ? O5 Ni1 O3 93.52(13) . 3_664 ? O1 Ni1 O3 170.69(15) . 3_664 ? N2 Ni1 O3 88.00(16) . 3_664 ? O5 Ni1 N1 89.63(14) . . ? O1 Ni1 N1 93.62(17) . . ? N2 Ni1 N1 176.89(18) . . ? O3 Ni1 N1 91.18(16) 3_664 . ? O5 Ni1 O2 155.67(13) . 3_664 ? O1 Ni1 O2 109.75(14) . 3_664 ? N2 Ni1 O2 86.11(17) . 3_664 ? O3 Ni1 O2 62.15(12) 3_664 3_664 ? N1 Ni1 O2 90.86(15) . 3_664 ? O5 Ni1 C17 124.80(14) . 3_664 ? O1 Ni1 C17 139.99(15) . 3_664 ? N2 Ni1 C17 83.90(18) . 3_664 ? O3 Ni1 C17 31.43(13) 3_664 3_664 ? N1 Ni1 C17 93.85(16) . 3_664 ? O2 Ni1 C17 30.93(13) 3_664 3_664 ? C2 C3 C4 116.3(4) . . ? C2 C3 C8 123.5(4) . 1_565 ? C4 C3 C8 120.1(4) . 1_565 ? C17 O2 Ni1 86.4(3) . 2_655 ? C6 N2 C10 116.7(4) . . ? C6 N2 Ni1 120.4(3) . . ? C10 N2 Ni1 122.7(3) . . ? Ni1 O1 HW1 110(4) . . ? Ni1 O1 HW2 131(4) . . ? HW1 O1 HW2 119(6) . . ? C18 O5 Ni1 133.4(3) . . ? C17 O3 Ni1 90.9(3) . 2_655 ? C8 C7 C6 119.8(5) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C1 N1 C5 115.6(4) . . ? C1 N1 Ni1 125.5(3) . . ? C5 N1 Ni1 118.9(3) . . ? O2 C17 O3 119.7(4) . . ? O2 C17 C11 122.1(4) . . ? O3 C17 C11 118.0(4) . . ? O2 C17 Ni1 62.7(2) . 2_655 ? O3 C17 Ni1 57.6(2) . 2_655 ? C11 C17 Ni1 167.2(3) . 2_655 ? C13 C12 C11 119.7(4) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C10 C9 C8 122.0(5) . . ? C10 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? C13 O6 H21 112(4) . . ? O6 C13 C12 118.5(5) . . ? O6 C13 C14 122.8(5) . . ? C12 C13 C14 118.7(4) . . ? C14 C15 C16 118.8(4) . . ? C14 C15 C18 119.2(4) . . ? C16 C15 C18 122.0(4) . . ? C16 C11 C12 120.7(5) . . ? C16 C11 C17 119.1(4) . . ? C12 C11 C17 120.3(4) . . ? C3 C2 C1 119.8(5) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? N1 C5 C4 123.4(5) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? C5 C4 C3 120.1(4) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? N2 C10 C9 123.0(5) . . ? N2 C10 H10 118.5 . . ? C9 C10 H10 118.5 . . ? C15 C14 C13 121.7(4) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? O5 C18 O4 125.6(5) . . ? O5 C18 C15 115.3(4) . . ? O4 C18 C15 119.0(4) . . ? C7 C8 C9 114.8(4) . . ? C7 C8 C3 120.6(4) . 1_545 ? C9 C8 C3 124.6(4) . 1_545 ? C11 C16 C15 120.3(4) . . ? C11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? N2 C6 C7 123.6(5) . . ? N2 C6 H6 118.2 . . ? C7 C6 H6 118.2 . . ? N1 C1 C2 124.7(5) . . ? N1 C1 H1 117.6 . . ? C2 C1 H1 117.6 . . ? 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 O5 Ni1 N2 C6 -148.8(6) . . . . ? O1 Ni1 N2 C6 -54.5(6) . . . . ? O3 Ni1 N2 C6 117.8(6) 3_664 . . . ? N1 Ni1 N2 C6 43(3) . . . . ? O2 Ni1 N2 C6 55.6(6) 3_664 . . . ? C17 Ni1 N2 C6 86.6(6) 3_664 . . . ? O5 Ni1 N2 C10 35.8(7) . . . . ? O1 Ni1 N2 C10 130.1(7) . . . . ? O3 Ni1 N2 C10 -57.6(7) 3_664 . . . ? N1 Ni1 N2 C10 -132(3) . . . . ? O2 Ni1 N2 C10 -119.8(7) 3_664 . . . ? C17 Ni1 N2 C10 -88.8(7) 3_664 . . . ? O1 Ni1 O5 C18 -2.7(4) . . . . ? N2 Ni1 O5 C18 84.3(4) . . . . ? O3 Ni1 O5 C18 172.5(4) 3_664 . . . ? N1 Ni1 O5 C18 -96.3(5) . . . . ? O2 Ni1 O5 C18 172.4(4) 3_664 . . . ? C17 Ni1 O5 C18 169.3(4) 3_664 . . . ? O5 Ni1 N1 C1 145.3(7) . . . . ? O1 Ni1 N1 C1 50.9(7) . . . . ? N2 Ni1 N1 C1 -46(3) . . . . ? O3 Ni1 N1 C1 -121.2(7) 3_664 . . . ? O2 Ni1 N1 C1 -59.0(7) 3_664 . . . ? C17 Ni1 N1 C1 -89.8(7) 3_664 . . . ? O5 Ni1 N1 C5 -34.5(5) . . . . ? O1 Ni1 N1 C5 -128.9(5) . . . . ? N2 Ni1 N1 C5 134(3) . . . . ? O3 Ni1 N1 C5 59.1(5) 3_664 . . . ? O2 Ni1 N1 C5 121.2(5) 3_664 . . . ? C17 Ni1 N1 C5 90.4(5) 3_664 . . . ? Ni1 O2 C17 O3 8.6(4) 2_655 . . . ? Ni1 O2 C17 C11 -166.3(4) 2_655 . . . ? Ni1 O3 C17 O2 -9.0(4) 2_655 . . . ? Ni1 O3 C17 C11 166.0(4) 2_655 . . . ? C11 C12 C13 O6 179.0(5) . . . . ? C11 C12 C13 C14 -0.7(7) . . . . ? C13 C12 C11 C16 2.0(7) . . . . ? C13 C12 C11 C17 -177.8(4) . . . . ? O2 C17 C11 C16 151.0(5) . . . . ? O3 C17 C11 C16 -23.9(6) . . . . ? Ni1 C17 C11 C16 43.0(16) 2_655 . . . ? O2 C17 C11 C12 -29.2(7) . . . . ? O3 C17 C11 C12 155.9(4) . . . . ? Ni1 C17 C11 C12 -137.2(13) 2_655 . . . ? C4 C3 C2 C1 -1.8(15) . . . . ? C8 C3 C2 C1 178.3(9) 1_565 . . . ? C1 N1 C5 C4 -2.9(12) . . . . ? Ni1 N1 C5 C4 176.9(7) . . . . ? N1 C5 C4 C3 1.7(14) . . . . ? C2 C3 C4 C5 0.7(13) . . . . ? C8 C3 C4 C5 -179.4(7) 1_565 . . . ? C6 N2 C10 C9 2.5(14) . . . . ? Ni1 N2 C10 C9 178.0(8) . . . . ? C8 C9 C10 N2 -1.9(17) . . . . ? C16 C15 C14 C13 3.9(7) . . . . ? C18 C15 C14 C13 -173.8(4) . . . . ? O6 C13 C14 C15 178.1(5) . . . . ? C12 C13 C14 C15 -2.2(7) . . . . ? Ni1 O5 C18 O4 -16.0(8) . . . . ? Ni1 O5 C18 C15 159.2(3) . . . . ? C14 C15 C18 O5 -9.9(6) . . . . ? C16 C15 C18 O5 172.4(4) . . . . ? C14 C15 C18 O4 165.6(5) . . . . ? C16 C15 C18 O4 -12.1(7) . . . . ? C6 C7 C8 C9 1.8(13) . . . . ? C6 C7 C8 C3 -177.5(7) . . . 1_545 ? C10 C9 C8 C7 -0.3(15) . . . . ? C10 C9 C8 C3 178.9(9) . . . 1_545 ? C12 C11 C16 C15 -0.3(7) . . . . ? C17 C11 C16 C15 179.5(4) . . . . ? C14 C15 C16 C11 -2.6(7) . . . . ? C18 C15 C16 C11 175.1(4) . . . . ? C10 N2 C6 C7 -0.9(13) . . . . ? Ni1 N2 C6 C7 -176.5(7) . . . . ? C8 C7 C6 N2 -1.3(14) . . . . ? C5 N1 C1 C2 1.7(14) . . . . ? Ni1 N1 C1 C2 -178.1(8) . . . . ? C3 C2 C1 N1 0.6(18) . . . . ? 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 H21 O4 0.78(3) 1.92(4) 2.692(6) 178(6) 5_564 O1 HW1 O4 0.77(3) 2.14(4) 2.829(6) 148(6) . O1 HW2 O3 0.77(3) 2.16(5) 2.734(5) 131(5) 5_664 _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 27.68 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 1.375 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.096 #===END data_cupurpbm _database_code_depnum_ccdc_archive 'CCDC 657329' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H18 Cu N2 O10' _chemical_formula_weight 581.96 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.118(3) _cell_length_b 11.051(3) _cell_length_c 21.051(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.029(5) _cell_angle_gamma 90.00 _cell_volume 2324.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Purple _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1188 _exptl_absorpt_coefficient_mu 1.007 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9477 _diffrn_reflns_av_R_equivalents 0.0533 _diffrn_reflns_av_sigmaI/netI 0.0533 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.73 _reflns_number_total 2364 _reflns_number_gt 1630 _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^)+(0.0613P)^2^+3.8083P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2364 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0851 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1316 _refine_ls_wR_factor_gt 0.1152 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 Cu1 Cu 0.0000 0.25545(5) 0.2500 0.0258(2) Uani 1 2 d S . . O1 O 0.4010(3) 0.0419(3) 0.04890(13) 0.0494(8) Uani 1 1 d . . . O2 O 0.3415(3) 0.0171(3) -0.05651(14) 0.0482(8) Uani 1 1 d . . . H2A H 0.419(5) -0.007(4) -0.050(2) 0.050(15) Uiso 1 1 d . . . O3 O 0.0809(2) 0.2469(2) 0.17112(11) 0.0286(6) Uani 1 1 d . . . O4 O -0.1328(3) 0.2426(2) 0.12932(13) 0.0356(6) Uani 1 1 d . . . O5 O -0.1134(4) 0.1767(4) -0.11065(15) 0.0651(11) Uani 1 1 d . . . H5 H -0.183(6) 0.206(5) -0.108(3) 0.077(19) Uiso 1 1 d . . . N1 N 0.0000 0.0744(3) 0.2500 0.0280(10) Uani 1 2 d S . . N2 N 0.0000 0.4364(3) 0.2500 0.0264(10) Uani 1 2 d S . . C1 C -0.0482(5) 0.4996(3) 0.1976(2) 0.0444(11) Uani 1 1 d . . . H1 H -0.0825 0.4575 0.1604 0.053 Uiso 1 1 calc R . . C2 C -0.0495(4) 0.6238(3) 0.19571(19) 0.0428(11) Uani 1 1 d . . . H2 H -0.0839 0.6639 0.1579 0.051 Uiso 1 1 calc R . . C3 C 0.0000 0.6888(4) 0.2500 0.0281(12) Uani 1 2 d S . . C4 C 0.0000 -0.1764(4) 0.2500 0.0258(11) Uani 1 2 d S . . C5 C -0.1151(4) -0.1116(3) 0.22745(19) 0.0351(9) Uani 1 1 d . . . H5A H -0.1942 -0.1517 0.2115 0.042 Uiso 1 1 calc R . . C6 C -0.1111(4) 0.0122(3) 0.22892(19) 0.0347(9) Uani 1 1 d . . . H6 H -0.1894 0.0548 0.2146 0.042 Uiso 1 1 calc R . . C7 C -0.0303(4) 0.1669(4) -0.05350(19) 0.0398(10) Uani 1 1 d . . . C8 C -0.0630(4) 0.2064(4) 0.00448(19) 0.0372(9) Uani 1 1 d . . . H8 H -0.1458 0.2423 0.0056 0.045 Uiso 1 1 calc R . . C9 C 0.0268(4) 0.1927(3) 0.06100(18) 0.0287(8) Uani 1 1 d . . . C10 C 0.1500(4) 0.1414(3) 0.05934(18) 0.0311(8) Uani 1 1 d . . . H10 H 0.2111 0.1331 0.0970 0.037 Uiso 1 1 calc R . . C11 C 0.1830(4) 0.1019(3) 0.00108(17) 0.0302(8) Uani 1 1 d . . . C12 C 0.0931(4) 0.1137(4) -0.05489(18) 0.0365(9) Uani 1 1 d . . . H12 H 0.1152 0.0859 -0.0936 0.044 Uiso 1 1 calc R . . C13 C 0.3179(4) 0.0506(3) 0.00031(18) 0.0342(9) Uani 1 1 d . . . C14 C -0.0129(4) 0.2315(3) 0.12390(17) 0.0277(8) 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 Cu1 0.0334(4) 0.0200(3) 0.0244(4) 0.000 0.0059(3) 0.000 O1 0.0409(17) 0.079(2) 0.0281(16) -0.0020(15) 0.0041(14) 0.0199(16) O2 0.0386(18) 0.074(2) 0.0323(17) -0.0123(15) 0.0069(14) 0.0152(16) O3 0.0327(14) 0.0300(13) 0.0239(13) -0.0033(11) 0.0071(11) -0.0003(11) O4 0.0302(15) 0.0430(15) 0.0355(15) -0.0020(12) 0.0107(12) 0.0059(12) O5 0.041(2) 0.123(3) 0.0302(18) -0.0051(18) -0.0002(16) 0.025(2) N1 0.034(3) 0.024(2) 0.027(2) 0.000 0.007(2) 0.000 N2 0.042(3) 0.0199(19) 0.019(2) 0.000 0.009(2) 0.000 C1 0.069(3) 0.0259(19) 0.032(2) -0.0036(17) -0.008(2) -0.0009(19) C2 0.067(3) 0.0238(19) 0.033(2) 0.0052(16) -0.007(2) 0.0010(19) C3 0.034(3) 0.024(2) 0.027(3) 0.000 0.005(2) 0.000 C4 0.039(3) 0.022(2) 0.017(3) 0.000 0.005(2) 0.000 C5 0.039(2) 0.0261(18) 0.039(2) 0.0004(16) 0.0012(19) -0.0036(17) C6 0.034(2) 0.0310(19) 0.038(2) 0.0042(16) 0.0013(19) 0.0074(17) C7 0.036(2) 0.051(2) 0.030(2) -0.0036(18) -0.0028(18) 0.0033(19) C8 0.029(2) 0.051(2) 0.032(2) 0.0003(18) 0.0067(18) 0.0038(18) C9 0.029(2) 0.0264(17) 0.031(2) -0.0013(15) 0.0061(17) -0.0013(15) C10 0.034(2) 0.0320(19) 0.026(2) -0.0001(15) 0.0019(16) 0.0011(16) C11 0.030(2) 0.036(2) 0.026(2) -0.0005(16) 0.0093(16) 0.0010(17) C12 0.036(2) 0.053(2) 0.021(2) -0.0041(18) 0.0079(17) 0.0004(19) C13 0.037(2) 0.039(2) 0.027(2) -0.0025(17) 0.0068(18) 0.0025(18) C14 0.033(2) 0.0239(17) 0.027(2) 0.0031(14) 0.0077(17) 0.0001(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 Cu1 O3 1.965(2) . ? Cu1 O3 1.965(2) 2 ? Cu1 N2 2.000(4) . ? Cu1 N1 2.001(4) . ? O1 C13 1.221(5) . ? O2 C13 1.309(4) . ? O2 H2A 0.82(5) . ? O3 C14 1.274(4) . ? O4 C14 1.242(4) . ? O5 C7 1.360(5) . ? O5 H5 0.79(6) . ? N1 C6 1.333(4) . ? N1 C6 1.333(4) 2 ? N2 C1 1.332(4) 2 ? N2 C1 1.332(4) . ? C1 C2 1.373(5) . ? C1 H1 0.9300 . ? C2 C3 1.376(5) . ? C2 H2 0.9300 . ? C3 C2 1.376(5) 2 ? C3 C4 1.489(6) 1_565 ? C4 C5 1.386(4) 2 ? C4 C5 1.386(4) . ? C4 C3 1.489(6) 1_545 ? C5 C6 1.368(5) . ? C5 H5A 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.384(6) . ? C7 C12 1.385(6) . ? C8 C9 1.388(5) . ? C8 H8 0.9300 . ? C9 C10 1.375(5) . ? C9 C14 1.505(5) . ? C10 C11 1.391(5) . ? C10 H10 0.9300 . ? C11 C12 1.377(5) . ? C11 C13 1.480(5) . ? C12 H12 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 O3 Cu1 O3 174.50(13) . 2 ? O3 Cu1 N2 92.75(7) . . ? O3 Cu1 N2 92.75(7) 2 . ? O3 Cu1 N1 87.25(7) . . ? O3 Cu1 N1 87.25(7) 2 . ? N2 Cu1 N1 180.000(1) . . ? C13 O2 H2A 104(3) . . ? C14 O3 Cu1 107.9(2) . . ? C7 O5 H5 114(4) . . ? C6 N1 C6 117.9(4) . 2 ? C6 N1 Cu1 121.1(2) . . ? C6 N1 Cu1 121.1(2) 2 . ? C1 N2 C1 116.8(4) 2 . ? C1 N2 Cu1 121.6(2) 2 . ? C1 N2 Cu1 121.6(2) . . ? N2 C1 C2 123.2(4) . . ? N2 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C1 C2 C3 119.8(4) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C2 117.0(5) . 2 ? C2 C3 C4 121.5(2) . 1_565 ? C2 C3 C4 121.5(2) 2 1_565 ? C5 C4 C5 117.8(4) 2 . ? C5 C4 C3 121.1(2) 2 1_545 ? C5 C4 C3 121.1(2) . 1_545 ? C6 C5 C4 119.2(4) . . ? C6 C5 H5A 120.4 . . ? C4 C5 H5A 120.4 . . ? N1 C6 C5 122.9(4) . . ? N1 C6 H6 118.5 . . ? C5 C6 H6 118.5 . . ? O5 C7 C8 123.7(4) . . ? O5 C7 C12 116.7(4) . . ? C8 C7 C12 119.6(4) . . ? C7 C8 C9 120.4(4) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 119.8(4) . . ? C10 C9 C14 120.6(3) . . ? C8 C9 C14 119.6(3) . . ? C9 C10 C11 119.7(4) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 120.5(4) . . ? C12 C11 C13 120.9(3) . . ? C10 C11 C13 118.6(3) . . ? C11 C12 C7 119.9(4) . . ? C11 C12 H12 120.0 . . ? C7 C12 H12 120.0 . . ? O1 C13 O2 122.9(4) . . ? O1 C13 C11 122.4(3) . . ? O2 C13 C11 114.8(3) . . ? O4 C14 O3 122.3(3) . . ? O4 C14 C9 120.6(3) . . ? O3 C14 C9 117.1(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 O3 Cu1 O3 C14 82.82(19) 2 . . . ? N2 Cu1 O3 C14 -97.18(19) . . . . ? N1 Cu1 O3 C14 82.82(19) . . . . ? O3 Cu1 N1 C6 -100.8(2) . . . . ? O3 Cu1 N1 C6 79.2(2) 2 . . . ? N2 Cu1 N1 C6 -157(100) . . . . ? O3 Cu1 N1 C6 79.2(2) . . . 2 ? O3 Cu1 N1 C6 -100.8(2) 2 . . 2 ? N2 Cu1 N1 C6 23(100) . . . 2 ? O3 Cu1 N2 C1 -130.6(2) . . . 2 ? O3 Cu1 N2 C1 49.4(2) 2 . . 2 ? N1 Cu1 N2 C1 -74(100) . . . 2 ? O3 Cu1 N2 C1 49.4(2) . . . . ? O3 Cu1 N2 C1 -130.6(2) 2 . . . ? N1 Cu1 N2 C1 106(100) . . . . ? C1 N2 C1 C2 0.1(3) 2 . . . ? Cu1 N2 C1 C2 -179.9(3) . . . . ? N2 C1 C2 C3 -0.3(7) . . . . ? C1 C2 C3 C2 0.1(3) . . . 2 ? C1 C2 C3 C4 -179.9(3) . . . 1_565 ? C5 C4 C5 C6 -0.7(3) 2 . . . ? C3 C4 C5 C6 179.3(3) 1_545 . . . ? C6 N1 C6 C5 -0.7(3) 2 . . . ? Cu1 N1 C6 C5 179.3(3) . . . . ? C4 C5 C6 N1 1.4(5) . . . . ? O5 C7 C8 C9 179.7(4) . . . . ? C12 C7 C8 C9 -0.1(6) . . . . ? C7 C8 C9 C10 1.0(6) . . . . ? C7 C8 C9 C14 -177.4(4) . . . . ? C8 C9 C10 C11 -0.9(5) . . . . ? C14 C9 C10 C11 177.6(3) . . . . ? C9 C10 C11 C12 -0.1(6) . . . . ? C9 C10 C11 C13 178.1(3) . . . . ? C10 C11 C12 C7 1.0(6) . . . . ? C13 C11 C12 C7 -177.1(4) . . . . ? O5 C7 C12 C11 179.3(4) . . . . ? C8 C7 C12 C11 -0.9(6) . . . . ? C12 C11 C13 O1 178.1(4) . . . . ? C10 C11 C13 O1 -0.1(6) . . . . ? C12 C11 C13 O2 -1.0(5) . . . . ? C10 C11 C13 O2 -179.2(3) . . . . ? Cu1 O3 C14 O4 11.3(4) . . . . ? Cu1 O3 C14 C9 -165.7(2) . . . . ? C10 C9 C14 O4 -157.9(3) . . . . ? C8 C9 C14 O4 20.6(5) . . . . ? C10 C9 C14 O3 19.2(5) . . . . ? C8 C9 C14 O3 -162.3(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 O2 H2A O1 0.82(5) 1.86(5) 2.667(4) 168(5) 5_655 O5 H5 O4 0.79(6) 1.93(6) 2.688(4) 161(6) 7_455 _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 26.73 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.877 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.095 #===END data_znhipam _database_code_depnum_ccdc_archive 'CCDC 657330' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H22 N2 O13 Zn2' _chemical_formula_weight 701.20 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4720(14) _cell_length_b 9.6175(18) _cell_length_c 10.1060(19) _cell_angle_alpha 100.587(3) _cell_angle_beta 97.165(3) _cell_angle_gamma 112.381(3) _cell_volume 644.8(2) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 980 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 25.93 _exptl_crystal_description Block _exptl_crystal_colour 'Pale Yellow' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.806 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 1.938 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5163 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 26.02 _reflns_number_total 2485 _reflns_number_gt 2033 _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^)+(0.0544P)^2^+0.9004P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2485 _refine_ls_number_parameters 240 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1119 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.95757(6) 0.68083(5) 1.03226(4) 0.03980(19) Uani 1 1 d . . . N1 N 0.8025(4) 0.6177(3) 0.8348(3) 0.0308(6) Uani 1 1 d . . . O3 O 1.8461(4) 1.4829(3) 1.0836(2) 0.0361(6) Uani 1 1 d . . . O4 O 1.1971(4) 0.9759(3) 0.9942(3) 0.0379(6) Uani 1 1 d . . . O5 O 1.2216(4) 0.8238(3) 1.1280(3) 0.0369(6) Uani 1 1 d . . . O2 O 1.9261(4) 1.6059(3) 1.3051(3) 0.0481(7) Uani 1 1 d . . . O1 O 1.7713(4) 1.1471(3) 1.5245(3) 0.0436(7) Uani 1 1 d . . . O6 O 0.7951(5) 0.7936(4) 1.1165(3) 0.0477(7) Uani 1 1 d D . . O7 O 0.9193(18) 0.9411(12) 1.3952(9) 0.105(4) Uani 0.50 1 d PD . . HWC H 1.036(5) 0.967(11) 1.399(13) 0.08(3) Uiso 0.50 1 d PD . . HWD H 0.903(13) 1.005(9) 1.449(9) 0.08(3) Uiso 0.50 1 d PD . . C8 C 1.2847(5) 0.9530(4) 1.0950(3) 0.0273(7) Uani 1 1 d . . . C6 C 1.5692(5) 1.2173(4) 1.1508(3) 0.0259(7) Uani 1 1 d D . . C2 C 0.7091(6) 0.6734(4) 0.6230(4) 0.0345(8) Uani 1 1 d D . . C10 C 1.7062(5) 1.1756(4) 1.4027(3) 0.0308(8) Uani 1 1 d . . . C9 C 1.5426(5) 1.0570(4) 1.3122(3) 0.0302(8) Uani 1 1 d D . . C7 C 1.4716(5) 1.0783(4) 1.1869(3) 0.0266(7) Uani 1 1 d . . . C3 C 0.5649(5) 0.5246(4) 0.5702(3) 0.0289(7) Uani 1 1 d . . . C13 C 1.8427(5) 1.4871(4) 1.2106(3) 0.0289(7) Uani 1 1 d . . . C12 C 1.7328(5) 1.3359(4) 1.2434(3) 0.0271(7) Uani 1 1 d . . . C11 C 1.7994(5) 1.3141(4) 1.3698(3) 0.0310(8) Uani 1 1 d D . . C1 C 0.8245(6) 0.7156(4) 0.7554(4) 0.0349(8) Uani 1 1 d D . . C4 C 0.5442(7) 0.4233(5) 0.6542(4) 0.0481(11) Uani 1 1 d D . . C5 C 0.6624(7) 0.4735(5) 0.7843(4) 0.0504(11) Uani 1 1 d D . . HWA H 0.837(8) 0.828(6) 1.196(2) 0.082(14) Uiso 1 1 d D . . H1 H 0.920(6) 0.816(4) 0.791(5) 0.055(7) Uiso 1 1 d D . . H6 H 1.528(6) 1.235(4) 1.069(3) 0.033(6) Uiso 1 1 d D . . H11 H 1.904(5) 1.385(4) 1.439(3) 0.033(6) Uiso 1 1 d D . . H2 H 0.739(7) 0.753(5) 0.578(4) 0.055(7) Uiso 1 1 d D . . H9 H 1.477(5) 0.964(3) 1.335(4) 0.033(6) Uiso 1 1 d D . . H4 H 0.458(6) 0.319(4) 0.626(5) 0.055(7) Uiso 1 1 d D . . HWB H 0.804(9) 0.860(5) 1.079(6) 0.082(14) Uiso 1 1 d D . . H3 H 1.850(8) 1.226(6) 1.581(5) 0.062(16) Uiso 1 1 d . . . H5 H 0.655(7) 0.400(5) 0.834(4) 0.055(7) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0384(3) 0.0270(3) 0.0332(3) 0.01284(18) -0.01168(18) -0.00502(19) N1 0.0292(15) 0.0301(15) 0.0250(14) 0.0071(12) -0.0039(12) 0.0066(12) O3 0.0434(15) 0.0281(13) 0.0278(13) 0.0136(10) 0.0017(11) 0.0038(11) O4 0.0347(14) 0.0298(13) 0.0364(14) 0.0085(11) -0.0056(11) 0.0038(11) O5 0.0342(14) 0.0234(13) 0.0379(14) 0.0099(11) -0.0040(11) -0.0016(11) O2 0.0546(18) 0.0284(14) 0.0350(14) 0.0035(12) 0.0015(13) -0.0064(13) O1 0.0506(17) 0.0322(15) 0.0291(14) 0.0122(12) -0.0085(12) 0.0004(13) O6 0.0530(18) 0.0451(18) 0.0406(16) 0.0177(14) 0.0025(14) 0.0147(15) O7 0.144(9) 0.119(8) 0.057(5) -0.019(5) -0.025(6) 0.093(8) C8 0.0245(17) 0.0235(17) 0.0242(16) 0.0027(13) 0.0012(13) 0.0022(14) C6 0.0264(17) 0.0230(16) 0.0230(16) 0.0071(13) 0.0022(13) 0.0050(14) C2 0.036(2) 0.034(2) 0.0286(18) 0.0162(15) -0.0006(15) 0.0070(16) C10 0.0336(19) 0.0278(18) 0.0246(17) 0.0089(14) 0.0008(14) 0.0064(15) C9 0.0331(19) 0.0256(17) 0.0267(17) 0.0118(14) 0.0028(14) 0.0053(15) C7 0.0259(17) 0.0227(16) 0.0255(16) 0.0037(13) 0.0029(13) 0.0059(14) C3 0.0260(17) 0.0312(18) 0.0259(17) 0.0058(14) 0.0003(14) 0.0102(14) C13 0.0247(17) 0.0226(17) 0.0299(18) 0.0063(14) -0.0006(14) 0.0018(14) C12 0.0262(17) 0.0241(17) 0.0253(16) 0.0075(13) 0.0048(13) 0.0040(14) C11 0.0307(18) 0.0284(18) 0.0231(17) 0.0053(14) -0.0013(14) 0.0035(15) C1 0.035(2) 0.0310(19) 0.0306(18) 0.0095(15) 0.0001(15) 0.0063(16) C4 0.051(3) 0.028(2) 0.041(2) 0.0099(17) -0.0157(19) -0.0028(18) C5 0.052(3) 0.034(2) 0.044(2) 0.0169(18) -0.0157(19) -0.0002(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 Zn1 O5 1.920(2) . ? Zn1 O3 1.962(2) 1_445 ? Zn1 N1 2.034(3) . ? Zn1 O6 2.072(3) . ? N1 C1 1.322(5) . ? N1 C5 1.335(5) . ? O3 C13 1.280(4) . ? O3 Zn1 1.962(2) 1_665 ? O4 C8 1.241(4) . ? O5 C8 1.274(4) . ? O2 C13 1.230(4) . ? O1 C10 1.380(4) . ? O1 H3 0.82(5) . ? O6 HWA 0.78(2) . ? O6 HWB 0.78(2) . ? O7 HWC 0.80(2) . ? O7 HWD 0.80(2) . ? C8 C7 1.500(4) . ? C6 C12 1.390(5) . ? C6 C7 1.398(5) . ? C6 H6 0.92(3) . ? C2 C3 1.376(5) . ? C2 C1 1.395(5) . ? C2 H2 0.93(3) . ? C10 C11 1.373(5) . ? C10 C9 1.381(5) . ? C9 C7 1.392(5) . ? C9 H9 0.93(3) . ? C3 C4 1.384(5) . ? C3 C3 1.496(7) 2_666 ? C13 C12 1.495(5) . ? C12 C11 1.394(5) . ? C11 H11 0.92(3) . ? C1 H1 0.93(4) . ? C4 C5 1.376(6) . ? C4 H4 0.93(4) . ? C5 H5 0.93(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 O5 Zn1 O3 117.03(11) . 1_445 ? O5 Zn1 N1 134.68(11) . . ? O3 Zn1 N1 100.40(11) 1_445 . ? O5 Zn1 O6 100.57(12) . . ? O3 Zn1 O6 101.15(12) 1_445 . ? N1 Zn1 O6 95.96(12) . . ? C1 N1 C5 117.6(3) . . ? C1 N1 Zn1 123.2(2) . . ? C5 N1 Zn1 119.1(2) . . ? C13 O3 Zn1 118.1(2) . 1_665 ? C8 O5 Zn1 114.8(2) . . ? C10 O1 H3 113(4) . . ? Zn1 O6 HWA 111(5) . . ? Zn1 O6 HWB 107(5) . . ? HWA O6 HWB 111(6) . . ? HWC O7 HWD 109(4) . . ? O4 C8 O5 122.7(3) . . ? O4 C8 C7 121.4(3) . . ? O5 C8 C7 115.9(3) . . ? C12 C6 C7 119.4(3) . . ? C12 C6 H6 118(3) . . ? C7 C6 H6 123(3) . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2 126(3) . . ? C1 C2 H2 114(3) . . ? C11 C10 O1 122.4(3) . . ? C11 C10 C9 120.5(3) . . ? O1 C10 C9 117.1(3) . . ? C10 C9 C7 119.7(3) . . ? C10 C9 H9 121(2) . . ? C7 C9 H9 119(2) . . ? C9 C7 C6 120.2(3) . . ? C9 C7 C8 118.9(3) . . ? C6 C7 C8 120.9(3) . . ? C2 C3 C4 116.6(3) . . ? C2 C3 C3 121.7(4) . 2_666 ? C4 C3 C3 121.6(4) . 2_666 ? O2 C13 O3 124.2(3) . . ? O2 C13 C12 119.2(3) . . ? O3 C13 C12 116.6(3) . . ? C6 C12 C11 119.8(3) . . ? C6 C12 C13 121.8(3) . . ? C11 C12 C13 118.5(3) . . ? C10 C11 C12 120.4(3) . . ? C10 C11 H11 113(2) . . ? C12 C11 H11 127(2) . . ? N1 C1 C2 122.7(3) . . ? N1 C1 H1 118(3) . . ? C2 C1 H1 119(3) . . ? C5 C4 C3 120.2(4) . . ? C5 C4 H4 117(3) . . ? C3 C4 H4 123(3) . . ? N1 C5 C4 122.9(4) . . ? N1 C5 H5 119(3) . . ? C4 C5 H5 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 O5 Zn1 N1 C1 -34.8(4) . . . . ? O3 Zn1 N1 C1 178.9(3) 1_445 . . . ? O6 Zn1 N1 C1 76.4(3) . . . . ? O5 Zn1 N1 C5 149.5(3) . . . . ? O3 Zn1 N1 C5 3.3(4) 1_445 . . . ? O6 Zn1 N1 C5 -99.2(3) . . . . ? O3 Zn1 O5 C8 -177.4(2) 1_445 . . . ? N1 Zn1 O5 C8 40.5(3) . . . . ? O6 Zn1 O5 C8 -69.0(3) . . . . ? Zn1 O5 C8 O4 -11.2(4) . . . . ? Zn1 O5 C8 C7 168.1(2) . . . . ? C11 C10 C9 C7 -0.1(6) . . . . ? O1 C10 C9 C7 -179.3(3) . . . . ? C10 C9 C7 C6 2.0(5) . . . . ? C10 C9 C7 C8 -175.3(3) . . . . ? C12 C6 C7 C9 -2.5(5) . . . . ? C12 C6 C7 C8 174.8(3) . . . . ? O4 C8 C7 C9 167.8(3) . . . . ? O5 C8 C7 C9 -11.4(5) . . . . ? O4 C8 C7 C6 -9.5(5) . . . . ? O5 C8 C7 C6 171.3(3) . . . . ? C1 C2 C3 C4 -0.4(6) . . . . ? C1 C2 C3 C3 178.7(4) . . . 2_666 ? Zn1 O3 C13 O2 -9.2(5) 1_665 . . . ? Zn1 O3 C13 C12 172.1(2) 1_665 . . . ? C7 C6 C12 C11 1.0(5) . . . . ? C7 C6 C12 C13 -179.8(3) . . . . ? O2 C13 C12 C6 150.2(4) . . . . ? O3 C13 C12 C6 -31.0(5) . . . . ? O2 C13 C12 C11 -30.6(5) . . . . ? O3 C13 C12 C11 148.2(3) . . . . ? O1 C10 C11 C12 177.7(3) . . . . ? C9 C10 C11 C12 -1.4(6) . . . . ? C6 C12 C11 C10 1.0(5) . . . . ? C13 C12 C11 C10 -178.3(3) . . . . ? C5 N1 C1 C2 -0.4(6) . . . . ? Zn1 N1 C1 C2 -176.1(3) . . . . ? C3 C2 C1 N1 0.1(6) . . . . ? C2 C3 C4 C5 0.9(7) . . . . ? C3 C3 C4 C5 -178.2(5) 2_666 . . . ? C1 N1 C5 C4 0.9(7) . . . . ? Zn1 N1 C5 C4 176.8(4) . . . . ? C3 C4 C5 N1 -1.3(8) . . . . ? 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 HWA O7 0.78(2) 2.00(2) 2.772(9) 170(6) . O6 HWB O4 0.78(2) 1.87(2) 2.645(4) 172(6) 2_777 O1 H3 O2 0.82(5) 1.87(5) 2.675(4) 167(5) 2_988 O7 HWD O1 0.80(2) 2.06(4) 2.817(9) 158(10) 1_455 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.703 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.090 #===END