# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Zhu, Guangshan' _publ_contact_author_email zhugs@mail.jlu.edu.cn loop_ _publ_author_name G.Zhu F.Sun J.Jia B.Zheng L.Gao T.Borjigin H.Ren T.Zhang data_JUC-101 _database_code_depnum_ccdc_archive 'CCDC 851215' #TrackingRef '- JUC-101.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measure' _chemical_formula_moiety 'C66 H42 In3 O16' _chemical_formula_sum 'C66 H42 In3 O16' _chemical_formula_weight 1435.41 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' In In -0.7276 1.3100 '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 Hexagonal _symmetry_space_group_name_H-M P-62c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+y, -x, -z+1/2' '-y, x-y, z' 'x, y, -z+1/2' '-x+y, -x, z' '-y, x-y, -z+1/2' 'y, x, z+1/2' 'x-y, -y, -z' '-x, -x+y, z+1/2' 'y, x, -z' 'x-y, -y, z+1/2' '-x, -x+y, -z' _cell_length_a 19.4356(9) _cell_length_b 19.4356(9) _cell_length_c 27.893(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 9124.8(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9922 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 24.96 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1414 _exptl_absorpt_coefficient_mu 0.399 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.826 _exptl_absorpt_correction_T_max 0.852 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _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 6.00cm _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 56282 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 28.39 _reflns_number_total 7764 _reflns_number_gt 6834 _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. loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.014 0.259 0.004 7054 2226 ' ' _platon_squeeze_details ; _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^)+(0.0186P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.007(12) _refine_ls_number_reflns 7764 _refine_ls_number_parameters 135 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0262 _refine_ls_R_factor_gt 0.0217 _refine_ls_wR_factor_ref 0.0422 _refine_ls_wR_factor_gt 0.0416 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _refine_ls_shift/su_max 0.002 _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 C1 C 0.78367(8) 0.49270(9) 0.68060(5) 0.0517(3) Uani 1 1 d . . . C2 C 0.82703(9) 0.55059(8) 0.64187(5) 0.0553(3) Uani 1 1 d . . . C3 C 0.79790(10) 0.59675(10) 0.62256(6) 0.0699(5) Uani 1 1 d . . . H3A H 0.7500 0.5903 0.6337 0.084 Uiso 1 1 calc R . . C4 C 0.83805(11) 0.65142(11) 0.58751(6) 0.0699(5) Uani 1 1 d . . . H4A H 0.8172 0.6816 0.5752 0.084 Uiso 1 1 calc R . . C5 C 0.90876(9) 0.66227(9) 0.57022(6) 0.0606(4) Uani 1 1 d . . . C6 C 0.93911(11) 0.61701(11) 0.58959(7) 0.0817(6) Uani 1 1 d . . . H6A H 0.9882 0.6253 0.5794 0.098 Uiso 1 1 calc R . . C7 C 0.89671(10) 0.55955(10) 0.62406(6) 0.0761(5) Uani 1 1 d . . . H7A H 0.9157 0.5270 0.6351 0.091 Uiso 1 1 calc R . . C8 C 1.0000 0.71007(10) 0.5000 0.0630(6) Uani 1 2 d S . . H8 H 1.0000 0.6622 0.5000 0.076 Uiso 1 2 calc SR . . C9 C 0.95475(9) 0.72309(8) 0.53377(5) 0.0592(4) Uani 1 1 d . . . C10 C 0.95445(9) 0.79370(8) 0.53314(5) 0.0524(4) Uani 1 1 d . . . H10A H 0.9234 0.8020 0.5552 0.063 Uiso 1 1 calc R . . C11 C 1.0000 0.85303(9) 0.5000 0.0467(5) Uani 1 2 d S . . C12 C 1.0000 0.92933(11) 0.5000 0.0418(4) Uani 1 2 d S . . C13 C 1.07034(10) 1.0000 0.5000 0.0449(4) Uani 1 2 d S . . H13 H 1.1182 1.0000 0.5000 0.054 Uiso 1 2 calc SR . . In1 In 0.635989(7) 0.418818(7) 0.7500 0.03691(4) Uani 1 2 d S . . O1 O 0.72109(7) 0.48823(6) 0.69530(4) 0.0663(3) Uani 1 1 d . . . O2 O 0.81421(6) 0.45354(7) 0.69541(4) 0.0681(3) Uani 1 1 d . . . O3 O 0.60153(9) 0.51049(9) 0.7500 0.0671(4) Uani 1 2 d S . . O4 O 0.6667 0.3333 0.7500 0.0379(5) Uani 1 6 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0596(9) 0.0465(9) 0.0432(8) 0.0106(7) 0.0104(7) 0.0221(8) C2 0.0623(9) 0.0489(8) 0.0522(8) 0.0159(7) 0.0186(7) 0.0260(8) C3 0.0690(11) 0.0762(11) 0.0768(12) 0.0329(10) 0.0353(9) 0.0455(10) C4 0.0750(11) 0.0717(11) 0.0805(12) 0.0345(10) 0.0337(10) 0.0497(9) C5 0.0775(11) 0.0516(8) 0.0583(10) 0.0201(7) 0.0349(8) 0.0363(8) C6 0.0931(13) 0.0841(12) 0.0921(13) 0.0421(11) 0.0515(11) 0.0625(11) C7 0.0847(12) 0.0739(11) 0.0873(12) 0.0435(10) 0.0430(10) 0.0528(10) C8 0.0743(15) 0.0497(8) 0.0732(15) 0.0207(6) 0.0414(13) 0.0371(7) C9 0.0706(10) 0.0498(8) 0.0635(9) 0.0197(7) 0.0342(8) 0.0347(8) C10 0.0613(9) 0.0530(8) 0.0522(9) 0.0144(7) 0.0269(7) 0.0357(7) C11 0.0501(11) 0.0416(8) 0.0512(12) 0.0085(5) 0.0171(9) 0.0250(5) C12 0.0415(10) 0.0428(7) 0.0406(10) 0.0052(4) 0.0104(8) 0.0208(5) C13 0.0429(7) 0.0463(12) 0.0465(10) 0.0077(9) 0.0038(4) 0.0232(6) In1 0.03716(7) 0.03831(7) 0.03441(6) 0.000 0.000 0.01823(6) O1 0.0708(7) 0.0615(6) 0.0665(7) 0.0274(5) 0.0286(6) 0.0331(6) O2 0.0687(7) 0.0689(7) 0.0667(7) 0.0329(6) 0.0196(6) 0.0345(6) O3 0.0720(10) 0.0627(9) 0.0766(11) 0.000 0.000 0.0411(8) O4 0.0356(7) 0.0356(7) 0.0425(13) 0.000 0.000 0.0178(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2448(16) . ? C1 O2 1.2466(18) . ? C1 C2 1.4815(18) . ? C2 C7 1.369(2) . ? C2 C3 1.387(2) . ? C3 C4 1.366(2) . ? C3 H3A 0.9300 . ? C4 C5 1.370(2) . ? C4 H4A 0.9300 . ? C5 C6 1.390(2) . ? C5 C9 1.4742(19) . ? C6 C7 1.389(2) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C9 1.3954(17) 12_766 ? C8 C9 1.3954(16) . ? C8 H8 0.9300 . ? C9 C10 1.3753(19) . ? C10 C11 1.3954(15) . ? C10 H10A 0.9300 . ? C11 C10 1.3953(15) 12_766 ? C11 C12 1.483(3) . ? C12 C13 1.3703(13) . ? C12 C13 1.3704(13) 5_675 ? C13 C12 1.3702(13) 3_765 ? C13 H13 0.9300 . ? In1 O4 2.02645(15) . ? In1 O1 2.1568(10) 4_556 ? In1 O1 2.1568(10) . ? In1 O2 2.1580(10) 3_655 ? In1 O2 2.1580(10) 6_656 ? In1 O3 2.1945(15) . ? O2 In1 2.1581(10) 2_666 ? O4 In1 2.02651(16) 3_655 ? O4 In1 2.02651(15) 2_666 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 126.52(13) . . ? O1 C1 C2 117.28(14) . . ? O2 C1 C2 116.20(13) . . ? C7 C2 C3 118.32(13) . . ? C7 C2 C1 120.80(14) . . ? C3 C2 C1 120.88(14) . . ? C4 C3 C2 121.48(15) . . ? C4 C3 H3A 119.3 . . ? C2 C3 H3A 119.3 . . ? C3 C4 C5 120.72(16) . . ? C3 C4 H4A 119.6 . . ? C5 C4 H4A 119.6 . . ? C4 C5 C6 118.44(14) . . ? C4 C5 C9 121.72(14) . . ? C6 C5 C9 119.77(14) . . ? C7 C6 C5 120.59(15) . . ? C7 C6 H6A 119.7 . . ? C5 C6 H6A 119.7 . . ? C2 C7 C6 120.31(15) . . ? C2 C7 H7A 119.8 . . ? C6 C7 H7A 119.8 . . ? C9 C8 C9 120.47(18) 12_766 . ? C9 C8 H8 119.8 12_766 . ? C9 C8 H8 119.8 . . ? C10 C9 C8 119.33(13) . . ? C10 C9 C5 120.36(12) . . ? C8 C9 C5 120.30(13) . . ? C9 C10 C11 121.03(13) . . ? C9 C10 H10A 119.5 . . ? C11 C10 H10A 119.5 . . ? C10 C11 C10 118.78(17) 12_766 . ? C10 C11 C12 120.61(8) 12_766 . ? C10 C11 C12 120.61(8) . . ? C13 C12 C13 119.5(2) . 5_675 ? C13 C12 C11 120.23(11) . . ? C13 C12 C11 120.23(11) 5_675 . ? C12 C13 C12 120.5(2) 3_765 . ? C12 C13 H13 119.8 3_765 . ? C12 C13 H13 119.8 . . ? O4 In1 O1 93.72(3) . 4_556 ? O4 In1 O1 93.72(3) . . ? O1 In1 O1 90.04(7) 4_556 . ? O4 In1 O2 93.52(3) . 3_655 ? O1 In1 O2 172.76(4) 4_556 3_655 ? O1 In1 O2 89.65(5) . 3_655 ? O4 In1 O2 93.52(3) . 6_656 ? O1 In1 O2 89.65(5) 4_556 6_656 ? O1 In1 O2 172.76(4) . 6_656 ? O2 In1 O2 89.75(7) 3_655 6_656 ? O4 In1 O3 179.44(4) . . ? O1 In1 O3 86.68(4) 4_556 . ? O1 In1 O3 86.68(4) . . ? O2 In1 O3 86.09(4) 3_655 . ? O2 In1 O3 86.09(4) 6_656 . ? C1 O1 In1 133.92(10) . . ? C1 O2 In1 134.21(9) . 2_666 ? In1 O4 In1 120.0 . 3_655 ? In1 O4 In1 120.0 . 2_666 ? In1 O4 In1 120.0 3_655 2_666 ? 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 O1 C1 C2 C7 179.40(16) . . . . ? O2 C1 C2 C7 -0.2(2) . . . . ? O1 C1 C2 C3 -0.9(2) . . . . ? O2 C1 C2 C3 179.50(16) . . . . ? C7 C2 C3 C4 -1.6(3) . . . . ? C1 C2 C3 C4 178.70(17) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C3 C4 C5 C9 -177.55(17) . . . . ? C4 C5 C6 C7 3.0(3) . . . . ? C9 C5 C6 C7 179.84(17) . . . . ? C3 C2 C7 C6 3.8(3) . . . . ? C1 C2 C7 C6 -176.49(16) . . . . ? C5 C6 C7 C2 -4.6(3) . . . . ? C9 C8 C9 C10 0.71(11) 12_766 . . . ? C9 C8 C9 C5 -178.32(18) 12_766 . . . ? C4 C5 C9 C10 33.5(3) . . . . ? C6 C5 C9 C10 -143.26(18) . . . . ? C4 C5 C9 C8 -147.49(16) . . . . ? C6 C5 C9 C8 35.8(2) . . . . ? C8 C9 C10 C11 -1.4(2) . . . . ? C5 C9 C10 C11 177.59(13) . . . . ? C9 C10 C11 C10 0.73(11) . . . 12_766 ? C9 C10 C11 C12 -179.27(11) . . . . ? C10 C11 C12 C13 -50.33(7) 12_766 . . . ? C10 C11 C12 C13 129.67(7) . . . . ? C10 C11 C12 C13 129.67(7) 12_766 . . 5_675 ? C10 C11 C12 C13 -50.33(7) . . . 5_675 ? C13 C12 C13 C12 0.0 5_675 . . 3_765 ? C11 C12 C13 C12 180.0 . . . 3_765 ? O2 C1 O1 In1 0.7(3) . . . . ? C2 C1 O1 In1 -178.80(10) . . . . ? O4 In1 O1 C1 -22.19(15) . . . . ? O1 In1 O1 C1 71.54(15) 4_556 . . . ? O2 In1 O1 C1 -115.69(15) 3_655 . . . ? O2 In1 O1 C1 159.1(3) 6_656 . . . ? O3 In1 O1 C1 158.21(15) . . . . ? O1 C1 O2 In1 -0.6(3) . . . 2_666 ? C2 C1 O2 In1 178.96(10) . . . 2_666 ? O1 In1 O4 In1 134.86(3) 4_556 . . 3_655 ? O1 In1 O4 In1 -134.86(3) . . . 3_655 ? O2 In1 O4 In1 -44.98(3) 3_655 . . 3_655 ? O2 In1 O4 In1 44.98(3) 6_656 . . 3_655 ? O3 In1 O4 In1 0.0 . . . 3_655 ? O1 In1 O4 In1 -45.14(3) 4_556 . . 2_666 ? O1 In1 O4 In1 45.14(3) . . . 2_666 ? O2 In1 O4 In1 135.02(3) 3_655 . . 2_666 ? O2 In1 O4 In1 -135.02(3) 6_656 . . 2_666 ? O3 In1 O4 In1 180.0 . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.368 _refine_diff_density_min -0.531 _refine_diff_density_rms 0.030 # Attachment '- JUC-102.cif' data_JUC-102 _database_code_depnum_ccdc_archive 'CCDC 851216' #TrackingRef '- JUC-102.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measure' _chemical_formula_moiety 'C66 H43 Mn3 O16' _chemical_formula_sum 'C66 H43 Mn3 O16' _chemical_formula_weight 1256.77 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' Mn Mn 0.3368 0.7283 '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 Hexagonal _symmetry_space_group_name_H-M P-62c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+y, -x, -z+1/2' '-y, x-y, z' 'x, y, -z+1/2' '-x+y, -x, z' '-y, x-y, -z+1/2' 'y, x, z+1/2' 'x-y, -y, -z' '-x, -x+y, z+1/2' 'y, x, -z' 'x-y, -y, z+1/2' '-x, -x+y, -z' _cell_length_a 20.0962(3) _cell_length_b 20.0962(3) _cell_length_c 26.9145(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 9413.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9271 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 21.70 _exptl_crystal_description polyhedra _exptl_crystal_colour 'pale pink' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1270 _exptl_absorpt_coefficient_mu 0.220 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.896 _exptl_absorpt_correction_T_max 0.896 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _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 6.00cm _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 58035 _diffrn_reflns_av_R_equivalents 0.0624 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 28.34 _reflns_number_total 8015 _reflns_number_gt 5907 _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. loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.015 0.250 0.005 7313 2176 ' ' _platon_squeeze_details ; _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^)+(0.0180P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.042(11) _refine_ls_number_reflns 8015 _refine_ls_number_parameters 135 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0514 _refine_ls_wR_factor_gt 0.0488 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 1.162 _refine_ls_shift/su_max 0.006 _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 C1 C 0.77785(9) 0.49157(8) 0.67988(5) 0.0551(4) Uani 1 1 d U . . C2 C 0.82245(8) 0.55355(8) 0.64156(5) 0.0568(4) Uani 1 1 d . . . C3 C 0.79655(9) 0.59943(9) 0.62253(6) 0.0671(5) Uani 1 1 d . . . H3A H 0.7491 0.5919 0.6330 0.081 Uiso 1 1 calc R . . C4 C 0.83822(9) 0.65662(9) 0.58836(6) 0.0682(5) Uani 1 1 d . . . H4A H 0.8190 0.6873 0.5768 0.082 Uiso 1 1 calc R . . C5 C 0.90802(8) 0.66874(7) 0.57126(6) 0.0558(4) Uani 1 1 d . . . C6 C 0.93659(9) 0.62325(9) 0.59070(7) 0.0829(6) Uani 1 1 d U . . H6A H 0.9839 0.6309 0.5800 0.099 Uiso 1 1 calc R . . C7 C 0.89439(9) 0.56644(9) 0.62605(6) 0.0807(5) Uani 1 1 d U . . H7A H 0.9142 0.5372 0.6393 0.097 Uiso 1 1 calc R . . C8 C 1.0000 0.71868(9) 0.5000 0.0625(6) Uani 1 2 d SU . . H8 H 1.0000 0.6724 0.5000 0.075 Uiso 1 2 calc SR . . C9 C 0.95499(8) 0.72951(7) 0.53433(5) 0.0527(4) Uani 1 1 d U . . C10 C 0.95415(7) 0.79852(7) 0.53343(5) 0.0482(4) Uani 1 1 d . . . H10A H 0.9227 0.8059 0.5554 0.058 Uiso 1 1 calc R . . C11 C 1.0000 0.85655(8) 0.5000 0.0430(5) Uani 1 2 d S . . C12 C 1.0000 0.92988(9) 0.5000 0.0404(4) Uani 1 2 d S . . C13 C 1.06898(8) 1.0000 0.5000 0.0397(4) Uani 1 2 d S . . H13 H 1.1153 1.0000 0.5000 0.048 Uiso 1 2 calc SR . . Mn1 Mn 0.632776(14) 0.416134(14) 0.7500 0.03741(7) Uani 1 2 d S . . O1 O 0.71583(6) 0.48497(5) 0.69350(4) 0.0676(3) Uani 1 1 d U . . O2 O 0.80679(6) 0.45252(6) 0.69355(4) 0.0706(3) Uani 1 1 d U . . O3 O 0.59505(10) 0.50306(10) 0.7500 0.1037(6) Uani 1 2 d SU . . O4 O 0.6667 0.3333 0.7500 0.0259(4) Uani 1 6 d SU . . 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 C1 0.0579(10) 0.0452(9) 0.0523(9) 0.0110(8) 0.0134(8) 0.0184(8) C2 0.0616(10) 0.0466(8) 0.0566(9) 0.0182(7) 0.0192(8) 0.0229(8) C3 0.0681(11) 0.0696(10) 0.0757(11) 0.0350(9) 0.0380(9) 0.0434(9) C4 0.0730(10) 0.0668(11) 0.0814(12) 0.0351(10) 0.0357(10) 0.0473(9) C5 0.0655(9) 0.0428(8) 0.0628(10) 0.0186(7) 0.0281(8) 0.0298(7) C6 0.0781(11) 0.0787(11) 0.1111(14) 0.0452(11) 0.0511(11) 0.0537(10) C7 0.0852(12) 0.0793(11) 0.0983(13) 0.0533(10) 0.0478(10) 0.0565(10) C8 0.0716(14) 0.0418(8) 0.0840(17) 0.0167(7) 0.0334(13) 0.0358(7) C9 0.0545(9) 0.0463(8) 0.0611(9) 0.0176(7) 0.0298(8) 0.0281(7) C10 0.0479(8) 0.0444(8) 0.0556(9) 0.0116(7) 0.0218(7) 0.0255(7) C11 0.0442(11) 0.0369(7) 0.0504(12) 0.0065(5) 0.0130(9) 0.0221(5) C12 0.0411(10) 0.0380(7) 0.0432(11) 0.0040(4) 0.0081(8) 0.0205(5) C13 0.0326(6) 0.0401(11) 0.0488(11) 0.0074(9) 0.0037(4) 0.0200(5) Mn1 0.03418(14) 0.03568(15) 0.04048(13) 0.000 0.000 0.01606(13) O1 0.0679(6) 0.0639(6) 0.0673(6) 0.0253(5) 0.0193(5) 0.0303(5) O2 0.0777(7) 0.0653(6) 0.0739(7) 0.0298(5) 0.0209(5) 0.0397(5) O3 0.1086(10) 0.0960(10) 0.1369(11) 0.000 0.000 0.0739(8) O4 0.0233(5) 0.0233(5) 0.0310(8) 0.000 0.000 0.0116(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 C1 O2 1.2433(17) . ? C1 O1 1.2410(16) . ? C1 C2 1.5173(18) . ? C2 C3 1.3648(19) . ? C2 C7 1.3990(19) . ? C3 C4 1.3804(18) . ? C3 H3A 0.9300 . ? C4 C5 1.3774(18) . ? C4 H4A 0.9300 . ? C5 C6 1.4017(19) . ? C5 C9 1.4890(17) . ? C6 C7 1.3997(19) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C9 1.3842(15) . ? C8 C9 1.3843(15) 12_766 ? C8 H8 0.9300 . ? C9 C10 1.3956(16) . ? C10 C11 1.3943(14) . ? C10 H10A 0.9300 . ? C11 C10 1.3943(14) 12_766 ? C11 C12 1.474(2) . ? C12 C13 1.3978(11) 5_675 ? C12 C13 1.3979(11) . ? C13 C12 1.3978(11) 3_765 ? C13 H13 0.9300 . ? Mn1 O4 2.0895(2) . ? Mn1 O2 2.1589(10) 3_655 ? Mn1 O2 2.1589(10) 6_656 ? Mn1 O1 2.1687(10) 4_556 ? Mn1 O1 2.1687(10) . ? Mn1 O3 2.2251(15) . ? O2 Mn1 2.1589(10) 2_666 ? O4 Mn1 2.0894(2) 2_666 ? O4 Mn1 2.0895(3) 3_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 O2 C1 O1 127.36(13) . . ? O2 C1 C2 116.66(14) . . ? O1 C1 C2 115.97(14) . . ? C3 C2 C7 118.08(13) . . ? C3 C2 C1 122.78(14) . . ? C7 C2 C1 119.10(14) . . ? C2 C3 C4 122.34(14) . . ? C2 C3 H3A 118.8 . . ? C4 C3 H3A 118.8 . . ? C5 C4 C3 120.67(14) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C4 C5 C6 118.23(13) . . ? C4 C5 C9 122.69(13) . . ? C6 C5 C9 119.06(12) . . ? C7 C6 C5 120.46(13) . . ? C7 C6 H6A 119.8 . . ? C5 C6 H6A 119.8 . . ? C2 C7 C6 120.16(14) . . ? C2 C7 H7A 119.9 . . ? C6 C7 H7A 119.9 . . ? C9 C8 C9 122.12(17) . 12_766 ? C9 C8 H8 118.9 . . ? C9 C8 H8 118.9 12_766 . ? C8 C9 C10 118.57(13) . . ? C8 C9 C5 120.84(12) . . ? C10 C9 C5 120.58(12) . . ? C11 C10 C9 120.73(13) . . ? C11 C10 H10A 119.6 . . ? C9 C10 H10A 119.6 . . ? C10 C11 C10 119.22(16) 12_766 . ? C10 C11 C12 120.39(8) 12_766 . ? C10 C11 C12 120.39(8) . . ? C13 C12 C13 118.38(18) 5_675 . ? C13 C12 C11 120.81(9) 5_675 . ? C13 C12 C11 120.81(9) . . ? C12 C13 C12 121.62(18) 3_765 . ? C12 C13 H13 119.2 3_765 . ? C12 C13 H13 119.2 . . ? O4 Mn1 O2 91.29(3) . 3_655 ? O4 Mn1 O2 91.29(3) . 6_656 ? O2 Mn1 O2 89.45(6) 3_655 6_656 ? O4 Mn1 O1 93.13(3) . 4_556 ? O2 Mn1 O1 175.58(4) 3_655 4_556 ? O2 Mn1 O1 90.58(4) 6_656 4_556 ? O4 Mn1 O1 93.13(3) . . ? O2 Mn1 O1 90.58(4) 3_655 . ? O2 Mn1 O1 175.58(4) 6_656 . ? O1 Mn1 O1 89.05(6) 4_556 . ? O4 Mn1 O3 179.23(5) . . ? O2 Mn1 O3 88.17(4) 3_655 . ? O2 Mn1 O3 88.17(4) 6_656 . ? O1 Mn1 O3 87.41(4) 4_556 . ? O1 Mn1 O3 87.41(4) . . ? C1 O1 Mn1 133.38(9) . . ? C1 O2 Mn1 136.41(10) . 2_666 ? Mn1 O4 Mn1 120.0 2_666 3_655 ? Mn1 O4 Mn1 120.0 2_666 . ? Mn1 O4 Mn1 120.0 3_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 O2 C1 C2 C3 178.54(15) . . . . ? O1 C1 C2 C3 -0.5(2) . . . . ? O2 C1 C2 C7 -3.7(2) . . . . ? O1 C1 C2 C7 177.32(15) . . . . ? C7 C2 C3 C4 1.0(2) . . . . ? C1 C2 C3 C4 178.77(14) . . . . ? C2 C3 C4 C5 1.2(3) . . . . ? C3 C4 C5 C6 -2.1(2) . . . . ? C3 C4 C5 C9 179.83(14) . . . . ? C4 C5 C6 C7 0.9(3) . . . . ? C9 C5 C6 C7 179.00(14) . . . . ? C3 C2 C7 C6 -2.2(3) . . . . ? C1 C2 C7 C6 179.93(14) . . . . ? C5 C6 C7 C2 1.3(3) . . . . ? C9 C8 C9 C10 1.25(9) 12_766 . . . ? C9 C8 C9 C5 -179.14(15) 12_766 . . . ? C4 C5 C9 C8 -147.02(14) . . . . ? C6 C5 C9 C8 34.9(2) . . . . ? C4 C5 C9 C10 32.6(2) . . . . ? C6 C5 C9 C10 -145.48(16) . . . . ? C8 C9 C10 C11 -2.54(19) . . . . ? C5 C9 C10 C11 177.86(12) . . . . ? C9 C10 C11 C10 1.29(10) . . . 12_766 ? C9 C10 C11 C12 -178.71(10) . . . . ? C10 C11 C12 C13 131.57(7) 12_766 . . 5_675 ? C10 C11 C12 C13 -48.43(7) . . . 5_675 ? C10 C11 C12 C13 -48.43(7) 12_766 . . . ? C10 C11 C12 C13 131.57(7) . . . . ? C13 C12 C13 C12 0.0 5_675 . . 3_765 ? C11 C12 C13 C12 180.0 . . . 3_765 ? O2 C1 O1 Mn1 7.1(2) . . . . ? C2 C1 O1 Mn1 -173.99(9) . . . . ? O4 Mn1 O1 C1 -24.15(14) . . . . ? O2 Mn1 O1 C1 -115.47(14) 3_655 . . . ? O2 Mn1 O1 C1 154.2(5) 6_656 . . . ? O1 Mn1 O1 C1 68.94(14) 4_556 . . . ? O3 Mn1 O1 C1 156.39(14) . . . . ? O1 C1 O2 Mn1 -9.3(3) . . . 2_666 ? C2 C1 O2 Mn1 171.86(10) . . . 2_666 ? O2 Mn1 O4 Mn1 135.26(3) 3_655 . . 2_666 ? O2 Mn1 O4 Mn1 -135.26(3) 6_656 . . 2_666 ? O1 Mn1 O4 Mn1 -44.61(3) 4_556 . . 2_666 ? O1 Mn1 O4 Mn1 44.61(3) . . . 2_666 ? O3 Mn1 O4 Mn1 180.0 . . . 2_666 ? O2 Mn1 O4 Mn1 -44.74(3) 3_655 . . 3_655 ? O2 Mn1 O4 Mn1 44.74(3) 6_656 . . 3_655 ? O1 Mn1 O4 Mn1 135.39(3) 4_556 . . 3_655 ? O1 Mn1 O4 Mn1 -135.39(3) . . . 3_655 ? O3 Mn1 O4 Mn1 0.0 . . . 3_655 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.412 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.019