# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'En-Qing Gao' _publ_contact_author_email EQGAO@CHEM.ECNU.EDU.CN _publ_section_title ; Ferromagnetic interactions through triple hydrogen bonds in the coordination polymers of a,a'- dihydroxy-bibenzyl-4,4'-dicarboxylate ; loop_ _publ_author_name 'En-Qing Gao' 'Ai-Ling Cheng' 'Yu Ma' # Attachment 'compound 1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 755125' #TrackingRef 'compound 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H24 Co O12' _chemical_formula_weight 467.28 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' 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 13.7575(2) _cell_length_b 14.2492(2) _cell_length_c 10.3048(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.2290(10) _cell_angle_gamma 90.00 _cell_volume 1907.38(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9980 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 27.55 _exptl_crystal_description patch _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 972 _exptl_absorpt_coefficient_mu 0.964 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7607 _exptl_absorpt_correction_T_max 0.9097 _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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.5 _diffrn_reflns_number 30877 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3753 _reflns_number_gt 3272 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0370P)^2^+0.5323P] 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 3753 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0302 _refine_ls_R_factor_gt 0.0244 _refine_ls_wR_factor_ref 0.0666 _refine_ls_wR_factor_gt 0.0630 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 Co1 Co 0.250371(15) 0.239407(14) 0.781029(19) 0.02350(8) Uani 1 1 d . . . C1 C 0.45577(11) 0.33037(11) 0.93883(15) 0.0246(3) Uani 1 1 d . . . C2 C 0.54332(11) 0.33856(11) 1.07210(15) 0.0240(3) Uani 1 1 d . . . C3 C 0.61378(12) 0.41151(11) 1.09567(15) 0.0287(3) Uani 1 1 d . . . H3A H 0.6101 0.4538 1.0255 0.034 Uiso 1 1 calc R . . C4 C 0.55269(12) 0.27394(11) 1.17671(16) 0.0278(3) Uani 1 1 d . . . H4A H 0.5070 0.2238 1.1618 0.033 Uiso 1 1 calc R . . C5 C 0.62873(13) 0.28354(12) 1.30176(16) 0.0295(3) Uani 1 1 d . . . H5A H 0.6347 0.2391 1.3701 0.035 Uiso 1 1 calc R . . C6 C 0.68981(12) 0.42213(12) 1.22277(16) 0.0299(3) Uani 1 1 d . . . H6A H 0.7360 0.4718 1.2374 0.036 Uiso 1 1 calc R . . C7 C 0.69718(11) 0.35904(11) 1.32786(15) 0.0256(3) Uani 1 1 d . . . C8 C 0.77658(11) 0.36680(12) 1.47010(15) 0.0276(3) Uani 1 1 d . . . H8A H 0.8176 0.3091 1.4875 0.033 Uiso 1 1 calc R . . C9 C 0.72485(11) 0.37464(11) 1.58114(15) 0.0264(3) Uani 1 1 d . . . H9A H 0.6769 0.3220 1.5692 0.032 Uiso 1 1 calc R . . C10 C 0.80375(11) 0.36797(11) 1.72492(15) 0.0253(3) Uani 1 1 d . . . C11 C 0.86878(12) 0.29016(12) 1.75705(16) 0.0283(3) Uani 1 1 d . . . H11A H 0.8613 0.2431 1.6919 0.034 Uiso 1 1 calc R . . C12 C 0.81214(12) 0.43451(12) 1.82631(15) 0.0296(3) Uani 1 1 d . . . H12A H 0.7678 0.4858 1.8078 0.036 Uiso 1 1 calc R . . C13 C 1.04115(11) 0.34393(11) 2.11824(15) 0.0251(3) Uani 1 1 d . . . C14 C 0.95454(11) 0.35039(11) 1.98405(15) 0.0250(3) Uani 1 1 d . . . C15 C 0.88621(12) 0.42525(12) 1.95528(16) 0.0297(3) Uani 1 1 d . . . H15A H 0.8900 0.4696 2.0230 0.036 Uiso 1 1 calc R . . C16 C 0.94393(12) 0.28189(11) 1.88380(16) 0.0274(3) Uani 1 1 d . . . H16A H 0.9878 0.2303 1.9025 0.033 Uiso 1 1 calc R . . O1 O 0.38308(9) 0.27550(8) 0.94021(11) 0.0329(3) Uani 1 1 d . . . OW1 O 0.52660(12) 0.50575(11) 0.68754(17) 0.0428(3) Uani 1 1 d . . . H1D H 0.5185(19) 0.4733(19) 0.743(3) 0.069(9) Uiso 1 1 d . . . H1C H 0.475(2) 0.520(2) 0.643(3) 0.078(11) Uiso 1 1 d . . . O2 O 0.45776(8) 0.37738(8) 0.83808(11) 0.0327(3) Uani 1 1 d . . . OW2 O -0.04417(11) -0.04126(10) 0.81393(14) 0.0402(3) Uani 1 1 d . . . H2D H -0.0282(18) 0.0049(18) 0.777(2) 0.062(8) Uiso 1 1 d . . . H2C H -0.085(2) -0.0232(19) 0.849(3) 0.078(9) Uiso 1 1 d . . . O3 O 0.84433(9) 0.44294(9) 1.47693(12) 0.0359(3) Uani 1 1 d . . . H3E H 0.8994(18) 0.4326(16) 1.539(2) 0.060(7) Uiso 1 1 d . . . O4 O 0.66641(9) 0.45965(9) 1.55847(11) 0.0308(3) Uani 1 1 d . . . H4E H 0.6295(17) 0.4623(16) 1.599(2) 0.054(7) Uiso 1 1 d . . . O5 O 1.11772(8) 0.29478(8) 2.11723(11) 0.0315(3) Uani 1 1 d . . . O6 O 1.03489(8) 0.38706(8) 2.22073(11) 0.0324(3) Uani 1 1 d . . . O7 O 0.26649(11) 0.35441(9) 0.67058(13) 0.0358(3) Uani 1 1 d . . . H7D H 0.3336(19) 0.3693(16) 0.707(2) 0.059(7) Uiso 1 1 d . . . H7C H 0.2525(18) 0.3582(17) 0.593(3) 0.062(8) Uiso 1 1 d . . . O8 O 0.33102(10) 0.15244(10) 0.68292(14) 0.0380(3) Uani 1 1 d . . . H8D H 0.3425(18) 0.1735(18) 0.621(3) 0.064(8) Uiso 1 1 d . . . H8C H 0.3791(18) 0.1188(16) 0.724(2) 0.052(7) Uiso 1 1 d . . . O9 O 0.22226(10) 0.12636(9) 0.89532(11) 0.0287(3) Uani 1 1 d . . . H9D H 0.2526(16) 0.0754(16) 0.906(2) 0.046(6) Uiso 1 1 d . . . H9C H 0.1572(18) 0.1165(15) 0.849(2) 0.052(6) Uiso 1 1 d . . . O10 O 0.16873(11) 0.32632(11) 0.87210(15) 0.0392(3) Uani 1 1 d . . . H10D H 0.1504(18) 0.3160(17) 0.931(3) 0.056(7) Uiso 1 1 d . . . H10C H 0.130(2) 0.3629(18) 0.823(3) 0.065(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.02331(12) 0.02911(13) 0.01492(12) 0.00014(8) 0.00201(9) -0.00299(8) C1 0.0245(8) 0.0276(8) 0.0194(7) -0.0035(6) 0.0041(6) 0.0007(6) C2 0.0236(7) 0.0289(8) 0.0178(7) -0.0028(6) 0.0044(6) 0.0021(6) C3 0.0306(8) 0.0309(9) 0.0211(7) 0.0022(6) 0.0039(6) -0.0012(6) C4 0.0269(8) 0.0297(8) 0.0243(8) -0.0019(6) 0.0051(7) -0.0034(6) C5 0.0333(9) 0.0327(9) 0.0194(7) 0.0026(6) 0.0046(7) 0.0002(7) C6 0.0277(8) 0.0322(9) 0.0257(8) -0.0014(7) 0.0031(7) -0.0049(6) C7 0.0232(7) 0.0326(8) 0.0188(7) -0.0034(6) 0.0040(6) 0.0023(6) C8 0.0214(7) 0.0370(9) 0.0212(8) -0.0012(6) 0.0028(6) 0.0008(6) C9 0.0227(7) 0.0330(8) 0.0210(7) 0.0004(6) 0.0038(6) 0.0010(6) C10 0.0231(8) 0.0320(8) 0.0188(7) 0.0025(6) 0.0043(6) -0.0031(6) C11 0.0312(8) 0.0305(8) 0.0202(7) -0.0023(6) 0.0045(6) -0.0019(6) C12 0.0282(8) 0.0336(9) 0.0230(8) 0.0015(7) 0.0029(6) 0.0059(7) C13 0.0236(8) 0.0285(8) 0.0205(7) 0.0042(6) 0.0035(6) -0.0011(6) C14 0.0233(7) 0.0315(8) 0.0183(7) 0.0032(6) 0.0041(6) -0.0017(6) C15 0.0321(9) 0.0322(9) 0.0207(7) -0.0019(6) 0.0033(7) 0.0026(7) C16 0.0261(8) 0.0290(8) 0.0246(8) 0.0023(6) 0.0049(6) 0.0021(6) O1 0.0277(6) 0.0438(7) 0.0203(5) 0.0028(5) -0.0012(5) -0.0093(5) OW1 0.0401(9) 0.0500(9) 0.0431(8) 0.0029(7) 0.0202(7) -0.0030(7) O2 0.0332(6) 0.0401(7) 0.0196(5) 0.0041(5) 0.0016(5) -0.0065(5) OW2 0.0381(7) 0.0448(8) 0.0390(7) -0.0012(6) 0.0144(6) -0.0036(6) O3 0.0252(6) 0.0514(8) 0.0264(6) 0.0021(5) 0.0020(5) -0.0086(5) O4 0.0257(6) 0.0423(7) 0.0235(6) 0.0007(5) 0.0068(5) 0.0062(5) O5 0.0259(6) 0.0443(7) 0.0191(5) -0.0001(5) 0.0003(4) 0.0086(5) O6 0.0303(6) 0.0420(7) 0.0206(5) -0.0027(5) 0.0027(5) 0.0054(5) O7 0.0391(8) 0.0418(7) 0.0200(6) 0.0061(5) 0.0008(5) -0.0102(5) O8 0.0377(7) 0.0483(8) 0.0301(7) 0.0038(6) 0.0142(6) 0.0084(6) O9 0.0298(7) 0.0315(7) 0.0203(6) 0.0011(5) 0.0023(5) -0.0026(5) O10 0.0425(8) 0.0492(8) 0.0287(7) 0.0057(6) 0.0154(6) 0.0135(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O7 2.0484(12) . ? Co1 O1 2.0774(11) . ? Co1 O10 2.0905(13) . ? Co1 O5 2.0947(10) 4_464 ? Co1 O9 2.1051(12) . ? Co1 O8 2.1279(13) . ? C1 O2 1.2434(19) . ? C1 O1 1.2732(18) . ? C1 C2 1.504(2) . ? C2 C3 1.387(2) . ? C2 C4 1.391(2) . ? C3 C6 1.389(2) . ? C3 H3A 0.9300 . ? C4 C5 1.373(2) . ? C4 H4A 0.9300 . ? C5 C7 1.396(2) . ? C5 H5A 0.9300 . ? C6 C7 1.385(2) . ? C6 H6A 0.9300 . ? C7 C8 1.516(2) . ? C8 O3 1.417(2) . ? C8 C9 1.538(2) . ? C8 H8A 0.9800 . ? C9 O4 1.4300(19) . ? C9 C10 1.524(2) . ? C9 H9A 0.9800 . ? C10 C12 1.387(2) . ? C10 C11 1.394(2) . ? C11 C16 1.378(2) . ? C11 H11A 0.9300 . ? C12 C15 1.389(2) . ? C12 H12A 0.9300 . ? C13 O6 1.2492(19) . ? C13 O5 1.2678(18) . ? C13 C14 1.502(2) . ? C14 C15 1.388(2) . ? C14 C16 1.394(2) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? OW1 H1D 0.78(3) . ? OW1 H1C 0.73(3) . ? OW2 H2D 0.82(3) . ? OW2 H2C 0.80(3) . ? O3 H3E 0.83(2) . ? O4 H4E 0.75(2) . ? O5 Co1 2.0947(10) 4_667 ? O7 H7D 0.90(2) . ? O7 H7C 0.76(3) . ? O8 H8D 0.77(3) . ? O8 H8C 0.81(2) . ? O9 H9D 0.83(2) . ? O9 H9C 0.88(2) . ? O10 H10D 0.75(2) . ? O10 H10C 0.80(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 Co1 O1 90.74(5) . . ? O7 Co1 O10 87.02(6) . . ? O1 Co1 O10 87.78(5) . . ? O7 Co1 O5 87.90(5) . 4_464 ? O1 Co1 O5 178.57(4) . 4_464 ? O10 Co1 O5 92.59(5) . 4_464 ? O7 Co1 O9 175.17(5) . . ? O1 Co1 O9 91.33(5) . . ? O10 Co1 O9 88.70(6) . . ? O5 Co1 O9 90.06(5) 4_464 . ? O7 Co1 O8 91.90(6) . . ? O1 Co1 O8 93.39(5) . . ? O10 Co1 O8 178.42(6) . . ? O5 Co1 O8 86.21(5) 4_464 . ? O9 Co1 O8 92.34(5) . . ? O2 C1 O1 124.99(14) . . ? O2 C1 C2 119.31(13) . . ? O1 C1 C2 115.68(13) . . ? C3 C2 C4 118.64(14) . . ? C3 C2 C1 121.43(14) . . ? C4 C2 C1 119.88(14) . . ? C2 C3 C6 120.83(14) . . ? C2 C3 H3A 119.6 . . ? C6 C3 H3A 119.6 . . ? C5 C4 C2 120.58(15) . . ? C5 C4 H4A 119.7 . . ? C2 C4 H4A 119.7 . . ? C4 C5 C7 120.96(15) . . ? C4 C5 H5A 119.5 . . ? C7 C5 H5A 119.5 . . ? C7 C6 C3 120.32(15) . . ? C7 C6 H6A 119.8 . . ? C3 C6 H6A 119.8 . . ? C6 C7 C5 118.58(14) . . ? C6 C7 C8 123.53(14) . . ? C5 C7 C8 117.89(14) . . ? O3 C8 C7 110.89(13) . . ? O3 C8 C9 111.44(13) . . ? C7 C8 C9 111.23(13) . . ? O3 C8 H8A 107.7 . . ? C7 C8 H8A 107.7 . . ? C9 C8 H8A 107.7 . . ? O4 C9 C10 113.19(12) . . ? O4 C9 C8 108.24(12) . . ? C10 C9 C8 111.28(12) . . ? O4 C9 H9A 108.0 . . ? C10 C9 H9A 108.0 . . ? C8 C9 H9A 108.0 . . ? C12 C10 C11 118.48(14) . . ? C12 C10 C9 123.06(14) . . ? C11 C10 C9 118.44(13) . . ? C16 C11 C10 121.03(15) . . ? C16 C11 H11A 119.5 . . ? C10 C11 H11A 119.5 . . ? C10 C12 C15 120.56(15) . . ? C10 C12 H12A 119.7 . . ? C15 C12 H12A 119.7 . . ? O6 C13 O5 124.58(14) . . ? O6 C13 C14 119.58(14) . . ? O5 C13 C14 115.84(13) . . ? C15 C14 C16 118.80(14) . . ? C15 C14 C13 121.34(14) . . ? C16 C14 C13 119.82(14) . . ? C14 C15 C12 120.61(15) . . ? C14 C15 H15A 119.7 . . ? C12 C15 H15A 119.7 . . ? C11 C16 C14 120.36(15) . . ? C11 C16 H16A 119.8 . . ? C14 C16 H16A 119.8 . . ? C1 O1 Co1 129.23(10) . . ? H1D OW1 H1C 107(3) . . ? H2D OW2 H2C 106(3) . . ? C8 O3 H3E 108.8(16) . . ? C9 O4 H4E 113.4(18) . . ? C13 O5 Co1 128.87(10) . 4_667 ? Co1 O7 H7D 103.8(14) . . ? Co1 O7 H7C 127.2(19) . . ? H7D O7 H7C 107(2) . . ? Co1 O8 H8D 116.8(19) . . ? Co1 O8 H8C 124.1(16) . . ? H8D O8 H8C 108(2) . . ? Co1 O9 H9D 124.8(15) . . ? Co1 O9 H9C 99.3(14) . . ? H9D O9 H9C 108(2) . . ? Co1 O10 H10D 128.7(19) . . ? Co1 O10 H10C 117.0(18) . . ? H10D O10 H10C 108(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.292 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.044 # Attachment 'compound 2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 755126' #TrackingRef 'compound 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H24 Mn O12' _chemical_formula_weight 463.29 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' _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 13.7420(4) _cell_length_b 14.5235(4) _cell_length_c 10.3594(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.0370(10) _cell_angle_gamma 90.00 _cell_volume 1954.47(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9871 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 27.63 _exptl_crystal_description patch _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 0.739 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8088 _exptl_absorpt_correction_T_max 0.9298 _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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.5 _diffrn_reflns_number 24025 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_sigmaI/netI 0.0111 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3829 _reflns_number_gt 3596 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0362P)^2^+0.5845P] 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 3829 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0246 _refine_ls_R_factor_gt 0.0228 _refine_ls_wR_factor_ref 0.0647 _refine_ls_wR_factor_gt 0.0626 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 0.252100(13) 0.237988(13) 0.782093(17) 0.02465(7) Uani 1 1 d . . . C1 C 0.46167(9) 0.33239(9) 0.94052(12) 0.0254(2) Uani 1 1 d . . . C2 C 0.54835(9) 0.34113(8) 1.07364(12) 0.0243(2) Uani 1 1 d . . . C3 C 0.61775(10) 0.41360(9) 1.09833(13) 0.0295(3) Uani 1 1 d . . . H3A H 0.6142 0.4555 1.0291 0.035 Uiso 1 1 calc R . . C4 C 0.55736(10) 0.27706(9) 1.17682(13) 0.0276(3) Uani 1 1 d . . . H4A H 0.5122 0.2275 1.1612 0.033 Uiso 1 1 calc R . . C5 C 0.63281(10) 0.28666(9) 1.30189(12) 0.0288(3) Uani 1 1 d . . . H5A H 0.6391 0.2425 1.3692 0.035 Uiso 1 1 calc R . . C6 C 0.69260(10) 0.42422(9) 1.22555(13) 0.0300(3) Uani 1 1 d . . . H6A H 0.7380 0.4737 1.2412 0.036 Uiso 1 1 calc R . . C7 C 0.69987(9) 0.36154(9) 1.32912(12) 0.0251(2) Uani 1 1 d . . . C8 C 0.77828(9) 0.36925(9) 1.47107(12) 0.0260(3) Uani 1 1 d . . . H8A H 0.8197 0.3129 1.4890 0.031 Uiso 1 1 calc R . . C9 C 0.72472(9) 0.37673(9) 1.58035(12) 0.0251(2) Uani 1 1 d . . . H9A H 0.6761 0.3254 1.5672 0.030 Uiso 1 1 calc R . . C10 C 0.80197(9) 0.36960(9) 1.72377(12) 0.0248(2) Uani 1 1 d . . . C11 C 0.86614(10) 0.29256(9) 1.75665(13) 0.0282(3) Uani 1 1 d . . . H11A H 0.8587 0.2461 1.6924 0.034 Uiso 1 1 calc R . . C12 C 0.81016(10) 0.43531(9) 1.82396(13) 0.0302(3) Uani 1 1 d . . . H12A H 0.7663 0.4859 1.8049 0.036 Uiso 1 1 calc R . . C13 C 1.03712(9) 0.34551(9) 2.11601(12) 0.0258(3) Uani 1 1 d . . . C14 C 0.95082(9) 0.35190(9) 1.98225(12) 0.0252(2) Uani 1 1 d . . . C15 C 0.88349(10) 0.42604(9) 1.95277(13) 0.0302(3) Uani 1 1 d . . . H15A H 0.8874 0.4699 2.0196 0.036 Uiso 1 1 calc R . . C16 C 0.94042(9) 0.28445(9) 1.88316(13) 0.0279(3) Uani 1 1 d . . . H16A H 0.9839 0.2336 1.9024 0.033 Uiso 1 1 calc R . . O1 O 0.38915(7) 0.27880(7) 0.94177(9) 0.0367(2) Uani 1 1 d . . . OW1 O 0.52641(9) 0.50387(9) 0.68657(14) 0.0425(3) Uani 1 1 d . . . H1D H 0.5171(17) 0.4725(16) 0.741(2) 0.069(7) Uiso 1 1 d . . . H1C H 0.474(2) 0.5159(18) 0.642(3) 0.085(9) Uiso 1 1 d . . . O2 O 0.46403(7) 0.37784(7) 0.83984(9) 0.0343(2) Uani 1 1 d . . . OW2 O -0.04430(9) -0.04007(8) 0.81314(12) 0.0407(2) Uani 1 1 d . . . H2D H -0.0277(16) 0.0056(15) 0.772(2) 0.062(6) Uiso 1 1 d . . . H2C H -0.0820(18) -0.0226(17) 0.847(3) 0.082(8) Uiso 1 1 d . . . O3 O 0.84556(7) 0.44467(7) 1.47884(10) 0.0338(2) Uani 1 1 d . . . H3E H 0.8987(15) 0.4350(14) 1.539(2) 0.054(5) Uiso 1 1 d . . . O4 O 0.66717(7) 0.46064(7) 1.55705(9) 0.0293(2) Uani 1 1 d . . . H4E H 0.6297(14) 0.4629(13) 1.5955(19) 0.047(5) Uiso 1 1 d . . . O5 O 1.11391(7) 0.29783(7) 2.11538(9) 0.0339(2) Uani 1 1 d . . . O6 O 1.03020(7) 0.38752(7) 2.21786(9) 0.0336(2) Uani 1 1 d . . . O7 O 0.27155(9) 0.35360(8) 0.66841(11) 0.0407(3) Uani 1 1 d . . . H7D H 0.3362(16) 0.3702(14) 0.701(2) 0.055(5) Uiso 1 1 d . . . H7C H 0.2523(15) 0.3601(14) 0.590(2) 0.057(6) Uiso 1 1 d . . . O8 O 0.33491(9) 0.14687(8) 0.68013(12) 0.0407(2) Uani 1 1 d . . . H8D H 0.3482(18) 0.1675(17) 0.616(3) 0.079(8) Uiso 1 1 d . . . H8C H 0.3823(16) 0.1124(14) 0.722(2) 0.053(6) Uiso 1 1 d . . . O9 O 0.21816(8) 0.12185(7) 0.89460(9) 0.0298(2) Uani 1 1 d . . . H9D H 0.2489(14) 0.0728(14) 0.9082(19) 0.047(5) Uiso 1 1 d . . . H9C H 0.1547(16) 0.1138(13) 0.849(2) 0.049(5) Uiso 1 1 d . . . O10 O 0.16692(9) 0.32909(9) 0.87508(12) 0.0418(3) Uani 1 1 d . . . H10D H 0.1475(14) 0.3183(14) 0.937(2) 0.051(5) Uiso 1 1 d . . . H10C H 0.1296(17) 0.3665(16) 0.827(2) 0.061(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.02466(11) 0.02948(12) 0.01661(11) -0.00004(7) 0.00236(8) -0.00413(7) C1 0.0243(6) 0.0299(6) 0.0196(6) -0.0030(5) 0.0041(5) 0.0002(5) C2 0.0231(5) 0.0290(6) 0.0185(6) -0.0028(5) 0.0036(4) 0.0013(5) C3 0.0315(6) 0.0319(6) 0.0214(6) 0.0026(5) 0.0037(5) -0.0020(5) C4 0.0280(6) 0.0286(6) 0.0237(6) -0.0022(5) 0.0048(5) -0.0036(5) C5 0.0333(6) 0.0304(6) 0.0198(6) 0.0025(5) 0.0048(5) 0.0006(5) C6 0.0288(6) 0.0319(6) 0.0257(6) -0.0012(5) 0.0039(5) -0.0055(5) C7 0.0226(5) 0.0314(6) 0.0190(6) -0.0033(5) 0.0036(4) 0.0030(5) C8 0.0223(5) 0.0326(6) 0.0203(6) -0.0008(5) 0.0030(4) 0.0015(5) C9 0.0220(5) 0.0307(6) 0.0201(6) 0.0007(5) 0.0035(5) 0.0000(5) C10 0.0233(6) 0.0306(6) 0.0184(6) 0.0024(5) 0.0041(5) -0.0025(5) C11 0.0315(6) 0.0287(6) 0.0214(6) -0.0021(5) 0.0046(5) -0.0018(5) C12 0.0303(6) 0.0332(7) 0.0235(6) 0.0019(5) 0.0037(5) 0.0071(5) C13 0.0247(6) 0.0301(6) 0.0199(6) 0.0037(5) 0.0033(5) -0.0005(5) C14 0.0229(5) 0.0318(6) 0.0186(6) 0.0038(5) 0.0035(5) -0.0011(5) C15 0.0330(6) 0.0330(7) 0.0207(6) -0.0026(5) 0.0032(5) 0.0027(5) C16 0.0273(6) 0.0286(6) 0.0249(6) 0.0034(5) 0.0046(5) 0.0026(5) O1 0.0304(5) 0.0497(6) 0.0225(5) 0.0034(4) -0.0016(4) -0.0128(4) OW1 0.0407(6) 0.0487(7) 0.0435(6) 0.0035(5) 0.0212(5) -0.0035(5) O2 0.0352(5) 0.0419(5) 0.0201(4) 0.0043(4) 0.0012(4) -0.0071(4) OW2 0.0385(6) 0.0453(6) 0.0392(6) -0.0007(5) 0.0140(5) -0.0029(5) O3 0.0246(4) 0.0480(6) 0.0246(5) 0.0009(4) 0.0020(4) -0.0087(4) O4 0.0245(4) 0.0397(5) 0.0228(4) 0.0017(4) 0.0066(4) 0.0070(4) O5 0.0279(4) 0.0479(6) 0.0205(4) -0.0006(4) 0.0006(3) 0.0096(4) O6 0.0319(5) 0.0439(5) 0.0207(4) -0.0025(4) 0.0026(4) 0.0065(4) O7 0.0454(6) 0.0460(6) 0.0220(5) 0.0092(4) -0.0009(4) -0.0135(5) O8 0.0405(6) 0.0493(6) 0.0357(6) 0.0046(5) 0.0173(5) 0.0096(5) O9 0.0332(5) 0.0307(5) 0.0205(4) 0.0019(4) 0.0021(4) -0.0028(4) O10 0.0454(6) 0.0524(7) 0.0308(6) 0.0056(5) 0.0171(5) 0.0150(5) _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 O7 2.1173(10) . ? Mn1 O1 2.1453(9) . ? Mn1 O5 2.1725(9) 4_464 ? Mn1 O9 2.1854(10) . ? Mn1 O10 2.1873(11) . ? Mn1 O8 2.2239(11) . ? C1 O2 1.2437(16) . ? C1 O1 1.2679(15) . ? C1 C2 1.5050(15) . ? C2 C3 1.3869(18) . ? C2 C4 1.3919(18) . ? C3 C6 1.3908(17) . ? C3 H3A 0.9300 . ? C4 C5 1.3773(17) . ? C4 H4A 0.9300 . ? C5 C7 1.3936(18) . ? C5 H5A 0.9300 . ? C6 C7 1.3856(18) . ? C6 H6A 0.9300 . ? C7 C8 1.5174(16) . ? C8 O3 1.4187(16) . ? C8 C9 1.5422(17) . ? C8 H8A 0.9800 . ? C9 O4 1.4297(15) . ? C9 C10 1.5219(16) . ? C9 H9A 0.9800 . ? C10 C12 1.3873(18) . ? C10 C11 1.3962(18) . ? C11 C16 1.3786(17) . ? C11 H11A 0.9300 . ? C12 C15 1.3917(17) . ? C12 H12A 0.9300 . ? C13 O6 1.2489(16) . ? C13 O5 1.2640(15) . ? C13 C14 1.5044(16) . ? C14 C15 1.3873(18) . ? C14 C16 1.3921(18) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? OW1 H1D 0.77(2) . ? OW1 H1C 0.74(3) . ? OW2 H2D 0.86(2) . ? OW2 H2C 0.76(3) . ? O3 H3E 0.81(2) . ? O4 H4E 0.747(19) . ? O5 Mn1 2.1725(9) 4_667 ? O7 H7D 0.87(2) . ? O7 H7C 0.78(2) . ? O8 H8D 0.81(3) . ? O8 H8C 0.82(2) . ? O9 H9D 0.82(2) . ? O9 H9C 0.85(2) . ? O10 H10D 0.79(2) . ? O10 H10C 0.80(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 Mn1 O1 88.36(4) . . ? O7 Mn1 O5 89.08(4) . 4_464 ? O1 Mn1 O5 177.44(4) . 4_464 ? O7 Mn1 O9 175.11(4) . . ? O1 Mn1 O9 95.07(4) . . ? O5 Mn1 O9 87.47(4) 4_464 . ? O7 Mn1 O10 87.02(5) . . ? O1 Mn1 O10 87.40(4) . . ? O5 Mn1 O10 92.31(4) 4_464 . ? O9 Mn1 O10 89.66(4) . . ? O7 Mn1 O8 91.76(5) . . ? O1 Mn1 O8 94.25(4) . . ? O5 Mn1 O8 85.98(4) 4_464 . ? O9 Mn1 O8 91.45(4) . . ? O10 Mn1 O8 177.92(4) . . ? O2 C1 O1 124.75(11) . . ? O2 C1 C2 119.62(11) . . ? O1 C1 C2 115.61(11) . . ? C3 C2 C4 118.83(11) . . ? C3 C2 C1 121.61(11) . . ? C4 C2 C1 119.52(11) . . ? C2 C3 C6 120.70(12) . . ? C2 C3 H3A 119.7 . . ? C6 C3 H3A 119.7 . . ? C5 C4 C2 120.39(12) . . ? C5 C4 H4A 119.8 . . ? C2 C4 H4A 119.8 . . ? C4 C5 C7 120.97(12) . . ? C4 C5 H5A 119.5 . . ? C7 C5 H5A 119.5 . . ? C7 C6 C3 120.34(12) . . ? C7 C6 H6A 119.8 . . ? C3 C6 H6A 119.8 . . ? C6 C7 C5 118.69(11) . . ? C6 C7 C8 123.44(11) . . ? C5 C7 C8 117.87(11) . . ? O3 C8 C7 110.83(10) . . ? O3 C8 C9 111.24(10) . . ? C7 C8 C9 111.01(10) . . ? O3 C8 H8A 107.9 . . ? C7 C8 H8A 107.9 . . ? C9 C8 H8A 107.9 . . ? O4 C9 C10 113.21(10) . . ? O4 C9 C8 107.83(10) . . ? C10 C9 C8 111.33(10) . . ? O4 C9 H9A 108.1 . . ? C10 C9 H9A 108.1 . . ? C8 C9 H9A 108.1 . . ? C12 C10 C11 118.56(11) . . ? C12 C10 C9 122.96(11) . . ? C11 C10 C9 118.47(11) . . ? C16 C11 C10 120.88(12) . . ? C16 C11 H11A 119.6 . . ? C10 C11 H11A 119.6 . . ? C10 C12 C15 120.49(12) . . ? C10 C12 H12A 119.8 . . ? C15 C12 H12A 119.8 . . ? O6 C13 O5 124.45(11) . . ? O6 C13 C14 119.58(11) . . ? O5 C13 C14 115.96(11) . . ? C15 C14 C16 118.89(11) . . ? C15 C14 C13 121.29(11) . . ? C16 C14 C13 119.76(11) . . ? C14 C15 C12 120.56(12) . . ? C14 C15 H15A 119.7 . . ? C12 C15 H15A 119.7 . . ? C11 C16 C14 120.46(12) . . ? C11 C16 H16A 119.8 . . ? C14 C16 H16A 119.8 . . ? C1 O1 Mn1 131.07(8) . . ? H1D OW1 H1C 104(2) . . ? H2D OW2 H2C 108(2) . . ? C8 O3 H3E 108.5(14) . . ? C9 O4 H4E 112.8(15) . . ? C13 O5 Mn1 129.93(8) . 4_667 ? Mn1 O7 H7D 107.5(13) . . ? Mn1 O7 H7C 128.3(15) . . ? H7D O7 H7C 109.0(19) . . ? Mn1 O8 H8D 117.5(18) . . ? Mn1 O8 H8C 123.4(14) . . ? H8D O8 H8C 108(2) . . ? Mn1 O9 H9D 125.2(13) . . ? Mn1 O9 H9C 99.7(13) . . ? H9D O9 H9C 110.8(18) . . ? Mn1 O10 H10D 127.7(15) . . ? Mn1 O10 H10C 117.3(15) . . ? H10D O10 H10C 109(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.292 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.039