# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'John Gordon' _publ_contact_author_email jgordon@lanl.gov loop_ _publ_author_name K.Vasudevan N.Smith B.Scott B.Bennett R.Muenchausen J.Gordon data_apx1167 _database_code_depnum_ccdc_archive 'CCDC 845795' #TrackingRef '- 845795.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H42 Br6 Ce2 O9' _chemical_formula_weight 1162.22 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 9.1670(6) _cell_length_b 24.8802(15) _cell_length_c 15.4087(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.2750(10) _cell_angle_gamma 90.00 _cell_volume 3468.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 140(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description cube _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2192 _exptl_absorpt_coefficient_mu 9.540 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2785 _exptl_absorpt_correction_T_max 0.2785 _exptl_absorpt_process_details 'SADABS v. 1 (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker D8 with APEXII CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 37881 _diffrn_reflns_av_R_equivalents 0.0543 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 27.03 _reflns_number_total 7583 _reflns_number_gt 6106 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, v. 7.0 (Bruker AXS, 2009)' _computing_cell_refinement 'SAINT+, v. 7.66a (Bruker AXS, 2009)' _computing_data_reduction 'SAINT+, v. 7.66a (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, v. 6.14, (Bruker AXS, 2000)' _computing_publication_material 'SHELXTL, v. 6.14, (Bruker AXS, 2000)' _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^)+(0.0357P)^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_number_reflns 7583 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0696 _refine_ls_wR_factor_gt 0.0639 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _refine_ls_shift/su_max 0.003 _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 Ce1 Ce 1.01694(3) 0.751255(9) 0.564145(16) 0.01277(6) Uani 1 1 d . . . Ce2 Ce 0.56900(3) 0.003640(9) 0.253233(15) 0.01215(6) Uani 1 1 d . . . Br1 Br 1.29825(5) 0.751149(19) 0.50542(3) 0.02186(11) Uani 1 1 d . . . Br2 Br 0.83315(5) 0.705151(18) 0.41217(3) 0.02046(11) Uani 1 1 d . . . Br3 Br 0.79981(5) -0.024024(19) 0.39845(3) 0.02496(12) Uani 1 1 d . . . Br4 Br 0.82294(5) 0.011368(19) 0.16041(3) 0.02203(11) Uani 1 1 d . . . Br5 Br 0.54757(5) 0.111448(17) 0.31731(3) 0.01844(10) Uani 1 1 d . . . Br6 Br 0.47496(5) -0.100280(18) 0.18920(3) 0.02729(12) Uani 1 1 d . . . O1 O 1.0050(3) 0.83944(11) 0.47727(19) 0.0157(6) Uani 1 1 d . . . O2 O 1.0651(3) 0.83499(11) 0.65260(18) 0.0184(7) Uani 1 1 d . . . O3 O 1.1650(3) 0.74259(12) 0.7192(2) 0.0205(7) Uani 1 1 d . . . O4 O 0.7683(3) 0.79552(12) 0.5763(2) 0.0208(7) Uani 1 1 d . . . O5 O 0.8494(3) 0.69733(11) 0.64992(19) 0.0172(7) Uani 1 1 d . . . O6 O 1.0829(3) 0.65314(12) 0.58759(19) 0.0204(7) Uani 1 1 d . . . O7 O 0.4754(3) 0.04844(13) 0.10446(19) 0.0225(7) Uani 1 1 d . . . O8 O 0.2871(3) 0.01972(11) 0.21651(19) 0.0172(7) Uani 1 1 d . . . O9 O 0.4083(3) -0.02208(12) 0.3734(2) 0.0211(7) Uani 1 1 d . . . C1 C 1.0135(6) 0.84187(19) 0.3850(3) 0.0259(11) Uani 1 1 d . . . H1A H 0.9729 0.8753 0.3613 0.039 Uiso 1 1 calc R . . H1B H 0.9584 0.8126 0.3552 0.039 Uiso 1 1 calc R . . H1C H 1.1149 0.8393 0.3769 0.039 Uiso 1 1 calc R . . C2 C 1.0844(5) 0.88419(17) 0.5232(3) 0.0183(10) Uani 1 1 d . . . H2A H 1.0600 0.9174 0.4910 0.022 Uiso 1 1 calc R . . H2B H 1.1902 0.8784 0.5292 0.022 Uiso 1 1 calc R . . C3 C 1.0384(5) 0.88727(17) 0.6114(3) 0.0198(10) Uani 1 1 d . . . H3A H 1.0952 0.9146 0.6469 0.024 Uiso 1 1 calc R . . H3B H 0.9345 0.8964 0.6055 0.024 Uiso 1 1 calc R . . C4 C 1.1061(6) 0.83494(18) 0.7461(3) 0.0233(11) Uani 1 1 d . . . H4A H 1.0369 0.8562 0.7732 0.028 Uiso 1 1 calc R . . H4B H 1.2042 0.8500 0.7628 0.028 Uiso 1 1 calc R . . C5 C 1.1034(6) 0.7778(2) 0.7748(3) 0.0319(12) Uani 1 1 d . . . H5A H 1.1578 0.7746 0.8340 0.038 Uiso 1 1 calc R . . H5B H 1.0020 0.7672 0.7762 0.038 Uiso 1 1 calc R . . C6 C 1.3220(6) 0.7365(2) 0.7409(3) 0.0361(13) Uani 1 1 d . . . H6A H 1.3692 0.7697 0.7299 0.054 Uiso 1 1 calc R . . H6B H 1.3543 0.7086 0.7055 0.054 Uiso 1 1 calc R . . H6C H 1.3478 0.7272 0.8020 0.054 Uiso 1 1 calc R . . C7 C 0.6680(5) 0.8198(2) 0.5066(3) 0.0307(12) Uani 1 1 d . . . H7A H 0.6075 0.7925 0.4748 0.046 Uiso 1 1 calc R . . H7B H 0.7229 0.8380 0.4674 0.046 Uiso 1 1 calc R . . H7C H 0.6064 0.8451 0.5307 0.046 Uiso 1 1 calc R . . C8 C 0.6955(5) 0.77412(19) 0.6453(3) 0.0231(10) Uani 1 1 d . . . H8A H 0.5944 0.7870 0.6379 0.028 Uiso 1 1 calc R . . H8B H 0.7462 0.7863 0.7021 0.028 Uiso 1 1 calc R . . C9 C 0.6968(5) 0.71447(18) 0.6420(3) 0.0256(11) Uani 1 1 d . . . H9A H 0.6521 0.6997 0.6898 0.031 Uiso 1 1 calc R . . H9B H 0.6410 0.7020 0.5868 0.031 Uiso 1 1 calc R . . C10 C 0.8629(5) 0.63935(17) 0.6501(3) 0.0236(11) Uani 1 1 d . . . H10A H 0.8087 0.6245 0.5962 0.028 Uiso 1 1 calc R . . H10B H 0.8234 0.6242 0.6994 0.028 Uiso 1 1 calc R . . C11 C 1.0228(5) 0.62671(18) 0.6574(3) 0.0226(10) Uani 1 1 d . . . H11A H 1.0746 0.6387 0.7139 0.027 Uiso 1 1 calc R . . H11B H 1.0361 0.5882 0.6535 0.027 Uiso 1 1 calc R . . C12 C 1.1233(5) 0.61685(19) 0.5222(3) 0.0246(11) Uani 1 1 d . . . H12A H 1.2002 0.5932 0.5493 0.037 Uiso 1 1 calc R . . H12B H 1.1580 0.6372 0.4766 0.037 Uiso 1 1 calc R . . H12C H 1.0386 0.5960 0.4974 0.037 Uiso 1 1 calc R . . C13 C 0.5224(5) 0.10052(19) 0.0770(3) 0.0275(12) Uani 1 1 d . . . H13A H 0.5130 0.1014 0.0140 0.041 Uiso 1 1 calc R . . H13B H 0.6237 0.1065 0.1025 0.041 Uiso 1 1 calc R . . H13C H 0.4617 0.1281 0.0962 0.041 Uiso 1 1 calc R . . C14 C 0.3219(6) 0.0378(2) 0.0721(3) 0.0315(12) Uani 1 1 d . . . H14A H 0.3081 -0.0001 0.0579 0.038 Uiso 1 1 calc R . . H14B H 0.2898 0.0584 0.0190 0.038 Uiso 1 1 calc R . . C15 C 0.2330(5) 0.0531(2) 0.1412(3) 0.0297(12) Uani 1 1 d . . . H15A H 0.2464 0.0908 0.1561 0.036 Uiso 1 1 calc R . . H15B H 0.1287 0.0464 0.1211 0.036 Uiso 1 1 calc R . . C16 C 0.2132(5) 0.02877(19) 0.2903(3) 0.0270(11) Uani 1 1 d . . . H16A H 0.1073 0.0310 0.2712 0.032 Uiso 1 1 calc R . . H16B H 0.2468 0.0621 0.3194 0.032 Uiso 1 1 calc R . . C17 C 0.2497(5) -0.0177(2) 0.3517(3) 0.0261(11) Uani 1 1 d . . . H17A H 0.2073 -0.0120 0.4047 0.031 Uiso 1 1 calc R . . H17B H 0.2088 -0.0505 0.3239 0.031 Uiso 1 1 calc R . . C18 C 0.4452(6) -0.0643(2) 0.4374(3) 0.0339(13) Uani 1 1 d . . . H18A H 0.3964 -0.0577 0.4870 0.051 Uiso 1 1 calc R . . H18B H 0.5502 -0.0649 0.4563 0.051 Uiso 1 1 calc R . . H18C H 0.4134 -0.0982 0.4114 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ce1 0.01249(12) 0.01254(12) 0.01402(13) -0.00118(9) 0.00434(9) -0.00161(9) Ce2 0.01073(12) 0.01137(12) 0.01376(12) -0.00040(9) 0.00015(9) 0.00085(9) Br1 0.0137(2) 0.0335(3) 0.0194(2) -0.0011(2) 0.00567(18) -0.00121(19) Br2 0.0213(2) 0.0216(2) 0.0182(2) -0.00446(18) 0.00215(19) -0.00454(19) Br3 0.0211(2) 0.0232(3) 0.0265(3) 0.0058(2) -0.0082(2) 0.0013(2) Br4 0.0140(2) 0.0266(3) 0.0265(3) -0.0031(2) 0.00648(19) -0.00047(19) Br5 0.0194(2) 0.0135(2) 0.0226(2) -0.00384(18) 0.00425(19) -0.00050(18) Br6 0.0240(3) 0.0147(2) 0.0420(3) -0.0090(2) 0.0020(2) -0.00084(19) O1 0.0182(16) 0.0138(15) 0.0158(16) -0.0007(12) 0.0049(13) -0.0029(12) O2 0.0270(18) 0.0158(16) 0.0124(15) -0.0037(12) 0.0031(13) -0.0031(13) O3 0.0205(17) 0.0219(17) 0.0195(17) -0.0010(13) 0.0041(14) 0.0003(14) O4 0.0137(16) 0.0247(18) 0.0251(18) 0.0042(14) 0.0064(13) 0.0023(13) O5 0.0167(16) 0.0113(15) 0.0251(17) -0.0007(13) 0.0079(13) 0.0000(12) O6 0.0264(18) 0.0168(16) 0.0201(17) -0.0003(13) 0.0096(14) 0.0030(14) O7 0.0214(17) 0.0258(18) 0.0194(17) 0.0070(14) 0.0009(14) 0.0014(14) O8 0.0145(16) 0.0166(16) 0.0194(17) 0.0019(13) -0.0003(13) 0.0023(13) O9 0.0172(17) 0.0290(18) 0.0172(17) 0.0051(14) 0.0032(13) -0.0026(14) C1 0.038(3) 0.025(3) 0.018(2) 0.001(2) 0.012(2) 0.002(2) C2 0.016(2) 0.016(2) 0.022(2) 0.0022(18) 0.0020(19) -0.0012(18) C3 0.021(2) 0.013(2) 0.025(3) -0.0059(19) 0.000(2) -0.0024(19) C4 0.038(3) 0.021(2) 0.013(2) -0.0058(19) 0.010(2) -0.006(2) C5 0.043(3) 0.034(3) 0.020(3) -0.001(2) 0.008(2) 0.009(3) C6 0.029(3) 0.055(4) 0.025(3) -0.003(3) 0.004(2) 0.013(3) C7 0.022(3) 0.036(3) 0.035(3) 0.012(2) 0.009(2) 0.008(2) C8 0.016(2) 0.026(3) 0.029(3) 0.002(2) 0.006(2) 0.004(2) C9 0.018(2) 0.024(3) 0.036(3) 0.005(2) 0.009(2) 0.001(2) C10 0.027(3) 0.014(2) 0.031(3) -0.001(2) 0.008(2) -0.001(2) C11 0.024(3) 0.017(2) 0.027(3) 0.000(2) 0.004(2) 0.002(2) C12 0.026(3) 0.023(3) 0.025(3) -0.010(2) 0.003(2) 0.010(2) C13 0.029(3) 0.027(3) 0.029(3) 0.014(2) 0.012(2) 0.004(2) C14 0.032(3) 0.034(3) 0.024(3) 0.012(2) -0.009(2) -0.004(2) C15 0.016(2) 0.028(3) 0.042(3) 0.022(2) -0.002(2) 0.005(2) C16 0.023(3) 0.026(3) 0.034(3) -0.005(2) 0.008(2) -0.001(2) C17 0.021(3) 0.036(3) 0.023(3) 0.002(2) 0.007(2) -0.011(2) C18 0.031(3) 0.038(3) 0.031(3) 0.022(2) 0.002(2) -0.009(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 Ce1 O2 2.490(3) . ? Ce1 O6 2.527(3) . ? Ce1 O3 2.560(3) . ? Ce1 O5 2.561(3) . ? Ce1 O1 2.563(3) . ? Ce1 O4 2.565(3) . ? Ce1 Br1 2.8673(5) . ? Ce1 Br2 2.8924(5) . ? Ce2 O7 2.569(3) . ? Ce2 O8 2.586(3) . ? Ce2 O9 2.624(3) . ? Ce2 Br6 2.8509(5) . ? Ce2 Br5 2.8759(5) . ? Ce2 Br3 2.9036(5) . ? Ce2 Br4 2.9283(5) . ? O1 C1 1.438(5) . ? O1 C2 1.451(5) . ? O2 C4 1.430(5) . ? O2 C3 1.451(5) . ? O3 C5 1.404(5) . ? O3 C6 1.432(6) . ? O4 C7 1.430(5) . ? O4 C8 1.445(5) . ? O5 C10 1.448(5) . ? O5 C9 1.449(5) . ? O6 C11 1.444(5) . ? O6 C12 1.445(5) . ? O7 C14 1.440(6) . ? O7 C13 1.450(5) . ? O8 C16 1.432(5) . ? O8 C15 1.447(5) . ? O9 C18 1.442(5) . ? O9 C17 1.443(5) . ? C2 C3 1.488(6) . ? C4 C5 1.491(6) . ? C8 C9 1.485(6) . ? C10 C11 1.485(6) . ? C14 C15 1.491(7) . ? C16 C17 1.496(7) . ? 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 Ce1 O6 135.47(10) . . ? O2 Ce1 O3 62.55(9) . . ? O6 Ce1 O3 72.93(9) . . ? O2 Ce1 O5 102.94(9) . . ? O6 Ce1 O5 64.51(9) . . ? O3 Ce1 O5 75.28(10) . . ? O2 Ce1 O1 63.80(9) . . ? O6 Ce1 O1 152.95(9) . . ? O3 Ce1 O1 122.08(9) . . ? O5 Ce1 O1 137.67(9) . . ? O2 Ce1 O4 71.46(10) . . ? O6 Ce1 O4 126.82(10) . . ? O3 Ce1 O4 108.16(10) . . ? O5 Ce1 O4 64.76(9) . . ? O1 Ce1 O4 72.96(9) . . ? O2 Ce1 Br1 94.85(7) . . ? O6 Ce1 Br1 80.65(7) . . ? O3 Ce1 Br1 85.76(7) . . ? O5 Ce1 Br1 143.80(6) . . ? O1 Ce1 Br1 78.51(6) . . ? O4 Ce1 Br1 151.44(7) . . ? O2 Ce1 Br2 143.49(7) . . ? O6 Ce1 Br2 80.06(7) . . ? O3 Ce1 Br2 150.96(7) . . ? O5 Ce1 Br2 83.72(7) . . ? O1 Ce1 Br2 86.93(6) . . ? O4 Ce1 Br2 79.68(7) . . ? Br1 Ce1 Br2 100.385(15) . . ? O7 Ce2 O8 63.85(9) . . ? O7 Ce2 O9 126.20(10) . . ? O8 Ce2 O9 62.44(9) . . ? O7 Ce2 Br6 92.62(7) . . ? O8 Ce2 Br6 80.14(6) . . ? O9 Ce2 Br6 81.38(7) . . ? O7 Ce2 Br5 82.54(7) . . ? O8 Ce2 Br5 79.03(6) . . ? O9 Ce2 Br5 84.73(7) . . ? Br6 Ce2 Br5 158.611(16) . . ? O7 Ce2 Br3 152.57(7) . . ? O8 Ce2 Br3 141.60(7) . . ? O9 Ce2 Br3 79.67(7) . . ? Br6 Ce2 Br3 101.178(16) . . ? Br5 Ce2 Br3 92.185(15) . . ? O7 Ce2 Br4 73.33(7) . . ? O8 Ce2 Br4 136.72(7) . . ? O9 Ce2 Br4 160.29(7) . . ? Br6 Ce2 Br4 96.335(15) . . ? Br5 Ce2 Br4 102.130(15) . . ? Br3 Ce2 Br4 81.608(16) . . ? C1 O1 C2 110.3(3) . . ? C1 O1 Ce1 123.2(2) . . ? C2 O1 Ce1 115.2(2) . . ? C4 O2 C3 116.1(3) . . ? C4 O2 Ce1 123.1(2) . . ? C3 O2 Ce1 120.6(2) . . ? C5 O3 C6 114.2(4) . . ? C5 O3 Ce1 108.2(3) . . ? C6 O3 Ce1 126.0(3) . . ? C7 O4 C8 113.0(3) . . ? C7 O4 Ce1 126.7(3) . . ? C8 O4 Ce1 114.6(2) . . ? C10 O5 C9 112.0(3) . . ? C10 O5 Ce1 117.7(2) . . ? C9 O5 Ce1 117.0(2) . . ? C11 O6 C12 114.0(3) . . ? C11 O6 Ce1 115.8(2) . . ? C12 O6 Ce1 125.9(3) . . ? C14 O7 C13 112.5(3) . . ? C14 O7 Ce2 113.4(3) . . ? C13 O7 Ce2 125.2(3) . . ? C16 O8 C15 113.7(3) . . ? C16 O8 Ce2 115.8(3) . . ? C15 O8 Ce2 117.8(2) . . ? C18 O9 C17 109.3(3) . . ? C18 O9 Ce2 124.3(3) . . ? C17 O9 Ce2 118.5(2) . . ? O1 C2 C3 107.0(3) . . ? O2 C3 C2 107.5(3) . . ? O2 C4 C5 106.6(4) . . ? O3 C5 C4 112.7(4) . . ? O4 C8 C9 109.6(4) . . ? O5 C9 C8 107.7(4) . . ? O5 C10 C11 107.1(4) . . ? O6 C11 C10 109.7(4) . . ? O7 C14 C15 108.7(4) . . ? O8 C15 C14 105.7(4) . . ? O8 C16 C17 107.1(4) . . ? O9 C17 C16 108.6(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.199 _refine_diff_density_min -0.664 _refine_diff_density_rms 0.152 # Attachment '- 845796.cif' data_apx1168a _database_code_depnum_ccdc_archive 'CCDC 845796' #TrackingRef '- 845796.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H34 Br4 Ce N O3' _chemical_formula_weight 736.19 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 15.7138(11) _cell_length_b 10.3798(7) _cell_length_c 15.0842(11) _cell_angle_alpha 90.00 _cell_angle_beta 103.6910(10) _cell_angle_gamma 90.00 _cell_volume 2390.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 140(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.046 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1412 _exptl_absorpt_coefficient_mu 8.603 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2132 _exptl_absorpt_correction_T_max 0.4800 _exptl_absorpt_process_details 'SADABS v. 1 (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker D8 with APEXII CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 25357 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 26.90 _reflns_number_total 5153 _reflns_number_gt 4128 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, v. 7.0 (Bruker AXS, 2009)' _computing_cell_refinement 'SAINT+, v. 7.66a (Bruker AXS, 2009)' _computing_data_reduction 'SAINT+, v. 7.66a (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, v. 6.14, (Bruker AXS, 2000)' _computing_publication_material 'SHELXTL, v. 6.14, (Bruker AXS, 2000)' _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^)+(0.0493P)^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_number_reflns 5153 _refine_ls_number_parameters 196 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1204 _refine_ls_wR_factor_gt 0.1137 _refine_ls_goodness_of_fit_ref 1.423 _refine_ls_restrained_S_all 1.438 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ce1 Ce 0.68934(2) 0.52537(3) 0.23883(2) 0.01854(12) Uani 1 1 d . . . Br1 Br 0.61727(4) 0.74180(6) 0.12433(4) 0.02437(17) Uani 1 1 d . . . Br2 Br 0.69809(5) 0.27572(7) 0.32643(5) 0.02925(18) Uani 1 1 d . . . Br3 Br 0.87256(5) 0.48603(7) 0.24187(5) 0.0350(2) Uani 1 1 d . . . Br4 Br 0.75138(5) 0.69172(8) 0.39198(5) 0.0412(2) Uani 1 1 d . . . O1 O 0.6866(3) 0.4298(4) 0.0773(3) 0.0229(10) Uani 1 1 d . . . O2 O 0.5468(3) 0.4188(4) 0.1511(3) 0.0201(9) Uani 1 1 d . . . O3 O 0.5527(3) 0.5452(4) 0.3096(3) 0.0240(10) Uani 1 1 d . . . C1 C 0.7337(5) 0.4947(7) 0.0188(5) 0.0307(16) Uani 1 1 d . . . H1A H 0.7376 0.4390 -0.0310 0.046 Uiso 1 1 calc R . . H1B H 0.7916 0.5158 0.0532 0.046 Uiso 1 1 calc R . . H1C H 0.7033 0.5722 -0.0047 0.046 Uiso 1 1 calc R . . C2 C 0.6057(4) 0.3803(7) 0.0253(4) 0.0242(14) Uani 1 1 d . . . H2A H 0.6166 0.3165 -0.0177 0.029 Uiso 1 1 calc R . . H2B H 0.5712 0.4493 -0.0088 0.029 Uiso 1 1 calc R . . C3 C 0.5573(4) 0.3208(6) 0.0880(4) 0.0254(15) Uani 1 1 d . . . H3A H 0.5006 0.2899 0.0542 0.030 Uiso 1 1 calc R . . H3B H 0.5900 0.2486 0.1200 0.030 Uiso 1 1 calc R . . C4 C 0.4811(4) 0.3902(6) 0.2003(4) 0.0231(14) Uani 1 1 d . . . H4A H 0.5000 0.3200 0.2429 0.028 Uiso 1 1 calc R . . H4B H 0.4264 0.3662 0.1586 0.028 Uiso 1 1 calc R . . C5 C 0.4704(4) 0.5101(6) 0.2495(5) 0.0261(15) Uani 1 1 d . . . H5A H 0.4505 0.5789 0.2060 0.031 Uiso 1 1 calc R . . H5B H 0.4267 0.4973 0.2845 0.031 Uiso 1 1 calc R . . C6 C 0.5581(5) 0.5099(7) 0.4040(5) 0.0296(16) Uani 1 1 d . . . H6A H 0.5094 0.5465 0.4234 0.044 Uiso 1 1 calc R . . H6B H 0.6118 0.5422 0.4417 0.044 Uiso 1 1 calc R . . H6C H 0.5567 0.4178 0.4091 0.044 Uiso 1 1 calc R . . N1 N 0.1688(9) 0.5298(13) 0.3538(8) 0.046(4) Uiso 0.50 1 d PD A 1 N1' N 0.1325(7) 0.5838(10) 0.3557(7) 0.021(2) Uiso 0.50 1 d PD . . C7 C 0.1284(10) 0.5847(14) 0.2560(9) 0.114(5) Uiso 1 1 d D A . C8 C 0.155(2) 0.473(2) 0.2066(13) 0.134(14) Uiso 0.50 1 d PD A 1 C9 C 0.1104(12) 0.3710(19) 0.2468(13) 0.062(5) Uiso 0.50 1 d PD A 1 C10 C 0.1578(15) 0.3842(17) 0.3484(13) 0.078(7) Uiso 0.50 1 d PD A 1 C11 C 0.2608(13) 0.5739(18) 0.3978(12) 0.044(5) Uiso 0.50 1 d P A 1 C12 C 0.0990(17) 0.615(2) 0.3878(14) 0.094(6) Uiso 0.50 1 d PD A 1 C13 C 0.0884(17) 0.692(3) 0.465(2) 0.093(10) Uiso 0.50 1 d PD A 1 C8' C 0.1685(16) 0.4515(17) 0.2522(19) 0.081(7) Uiso 0.50 1 d PD A 2 C9' C 0.1277(17) 0.352(2) 0.3051(17) 0.080(7) Uiso 0.50 1 d PD A 2 C10' C 0.1115(11) 0.4427(13) 0.3753(11) 0.043(4) Uiso 0.50 1 d PD A 2 C11' C 0.2317(10) 0.6083(17) 0.4023(11) 0.037(4) Uiso 0.50 1 d PD A 2 C12' C 0.0804(17) 0.687(2) 0.3893(18) 0.094(6) Uiso 0.50 1 d PD A 2 C13' C 0.084(2) 0.649(3) 0.486(2) 0.133(17) Uiso 0.50 1 d PD A 2 C14 C 0.0156(12) 0.741(2) 0.5069(14) 0.154(7) Uiso 1 1 d D . . C15 C 0.0199(19) 0.874(2) 0.5407(19) 0.261(14) Uiso 1 1 d D A . 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 Ce1 0.0231(2) 0.0176(2) 0.01477(19) -0.00155(14) 0.00414(14) -0.00034(14) Br1 0.0330(4) 0.0199(3) 0.0213(3) 0.0023(3) 0.0086(3) 0.0031(3) Br2 0.0328(4) 0.0250(4) 0.0268(4) 0.0087(3) 0.0009(3) -0.0004(3) Br3 0.0225(4) 0.0384(4) 0.0409(5) -0.0082(3) 0.0012(3) 0.0029(3) Br4 0.0448(5) 0.0451(5) 0.0347(4) -0.0227(4) 0.0115(4) -0.0129(4) O1 0.028(2) 0.026(2) 0.016(2) -0.0025(18) 0.0070(18) -0.0048(19) O2 0.028(2) 0.017(2) 0.015(2) -0.0028(18) 0.0052(18) -0.0015(18) O3 0.029(2) 0.028(3) 0.017(2) 0.0000(19) 0.0087(19) -0.0018(19) C1 0.041(4) 0.034(4) 0.021(4) -0.009(3) 0.016(3) -0.007(3) C2 0.028(4) 0.028(4) 0.016(3) -0.002(3) 0.003(3) 0.004(3) C3 0.028(4) 0.023(4) 0.021(3) -0.002(3) -0.002(3) 0.000(3) C4 0.021(3) 0.025(4) 0.022(3) 0.006(3) 0.001(3) -0.006(3) C5 0.026(4) 0.023(4) 0.031(4) 0.006(3) 0.011(3) 0.001(3) C6 0.041(4) 0.030(4) 0.019(3) 0.002(3) 0.011(3) 0.003(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 Ce1 O2 2.567(4) . ? Ce1 O3 2.623(4) . ? Ce1 O1 2.621(4) . ? Ce1 Br4 2.8640(8) . ? Ce1 Br1 2.8959(7) . ? Ce1 Br2 2.8972(8) . ? Ce1 Br3 2.8975(8) . ? O1 C2 1.422(8) . ? O1 C1 1.446(8) . ? O2 C3 1.430(7) . ? O2 C4 1.438(7) . ? O3 C5 1.439(8) . ? O3 C6 1.452(7) . ? C2 C3 1.481(9) . ? C4 C5 1.478(9) . ? N1 C10 1.521(17) . ? N1 C11 1.51(2) . ? N1 C12 1.584(16) . ? N1 C7 1.569(14) . ? N1' C7 1.491(16) . ? N1' C12' 1.507(17) . ? N1' C10' 1.544(14) . ? N1' C11' 1.573(14) . ? C7 C8 1.486(17) . ? C7 C8' 1.526(17) . ? C8 C9 1.477(18) . ? C9 C10 1.542(17) . ? C12 C13 1.456(17) . ? C13 C14 1.520(17) . ? C8' C9' 1.538(18) . ? C9' C10' 1.485(17) . ? C12' C13' 1.496(19) . ? C13' C14 1.533(18) . ? C14 C15 1.462(10) . ? 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 Ce1 O3 62.94(13) . . ? O2 Ce1 O1 62.43(13) . . ? O3 Ce1 O1 124.95(14) . . ? O2 Ce1 Br4 139.87(9) . . ? O3 Ce1 Br4 77.27(10) . . ? O1 Ce1 Br4 154.88(10) . . ? O2 Ce1 Br1 81.74(9) . . ? O3 Ce1 Br1 86.53(10) . . ? O1 Ce1 Br1 79.69(10) . . ? Br4 Ce1 Br1 91.36(2) . . ? O2 Ce1 Br2 77.95(9) . . ? O3 Ce1 Br2 80.77(10) . . ? O1 Ce1 Br2 94.25(10) . . ? Br4 Ce1 Br2 101.59(3) . . ? Br1 Ce1 Br2 159.31(2) . . ? O2 Ce1 Br3 133.63(9) . . ? O3 Ce1 Br3 155.63(10) . . ? O1 Ce1 Br3 76.07(10) . . ? Br4 Ce1 Br3 85.70(2) . . ? Br1 Ce1 Br3 111.45(2) . . ? Br2 Ce1 Br3 85.81(2) . . ? C2 O1 C1 110.6(5) . . ? C2 O1 Ce1 117.7(3) . . ? C1 O1 Ce1 119.6(3) . . ? C3 O2 C4 114.0(5) . . ? C3 O2 Ce1 115.2(4) . . ? C4 O2 Ce1 117.9(3) . . ? C5 O3 C6 112.9(5) . . ? C5 O3 Ce1 115.1(4) . . ? C6 O3 Ce1 121.0(4) . . ? O1 C2 C3 109.0(5) . . ? O2 C3 C2 106.6(5) . . ? O2 C4 C5 105.4(5) . . ? O3 C5 C4 109.8(5) . . ? C10 N1 C11 114.2(14) . . ? C10 N1 C12 119.4(16) . . ? C11 N1 C12 110.7(15) . . ? C10 N1 C7 107.1(11) . . ? C11 N1 C7 115.8(12) . . ? C12 N1 C7 86.9(10) . . ? C7 N1' C12' 116.0(13) . . ? C7 N1' C10' 103.8(10) . . ? C12' N1' C10' 116.9(14) . . ? C7 N1' C11' 104.6(11) . . ? C12' N1' C11' 107.1(14) . . ? C10' N1' C11' 107.6(11) . . ? N1' C7 C8 123.4(12) . . ? N1' C7 C8' 96.5(13) . . ? C8 C7 C8' 27.1(12) . . ? N1' C7 N1 30.4(6) . . ? C8 C7 N1 95.2(11) . . ? C8' C7 N1 68.1(12) . . ? C9 C8 C7 98.0(16) . . ? C8 C9 C10 100.4(13) . . ? N1 C10 C9 99.4(12) . . ? C13 C12 N1 142(2) . . ? C12 C13 C14 139(2) . . ? C7 C8' C9' 111.3(17) . . ? C10' C9' C8' 96.0(16) . . ? C9' C10' N1' 112.7(13) . . ? C13' C12' N1' 103.7(17) . . ? C12' C13' C14 99.6(19) . . ? C15 C14 C13 119(2) . . ? C15 C14 C13' 133(3) . . ? C13 C14 C13' 21(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.770 _refine_diff_density_min -2.181 _refine_diff_density_rms 0.192 # Attachment '- 845797.cif' data_apx1333 _database_code_depnum_ccdc_archive 'CCDC 845797' #TrackingRef '- 845797.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H20 Br3 Ce O4' _chemical_formula_weight 560.09 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.0605(19) _cell_length_b 13.140(3) _cell_length_c 12.781(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.348(2) _cell_angle_gamma 90.00 _cell_volume 1675.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 140(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1052 _exptl_absorpt_coefficient_mu 9.867 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1687 _exptl_absorpt_correction_T_max 0.5058 _exptl_absorpt_process_details 'SADABS v. 1 (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker D8 with APEXII CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18332 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 28.27 _reflns_number_total 3937 _reflns_number_gt 3362 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, v. 7.0 (Bruker AXS, 2009)' _computing_cell_refinement 'SAINT+, v. 7.66a (Bruker AXS, 2009)' _computing_data_reduction 'SAINT+, v. 7.66a (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, v. 6.14, (Bruker AXS, 2000)' _computing_publication_material 'SHELXTL, v. 6.14, (Bruker AXS, 2000)' _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. The ethyl group containing atoms C6 and C7 modeled as two positions, with site occupancy factors tied to 1.0. Site occupancy refined to 0.38(1). Bond distances constrained to reasonable values. ; _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^)+(0.0200P)^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_number_reflns 3937 _refine_ls_number_parameters 168 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0227 _refine_ls_wR_factor_ref 0.0485 _refine_ls_wR_factor_gt 0.0468 _refine_ls_goodness_of_fit_ref 1.259 _refine_ls_restrained_S_all 1.261 _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 Ce1 Ce 0.131525(16) 0.771101(13) 0.918079(12) 0.01969(5) Uani 1 1 d . A . Br1 Br 0.40107(3) 0.81556(2) 0.87809(2) 0.02738(8) Uani 1 1 d . . . Br2 Br -0.12365(3) 0.68314(3) 0.94973(2) 0.03163(8) Uani 1 1 d . . . Br3 Br 0.00201(3) 0.92823(3) 0.78535(3) 0.03586(9) Uani 1 1 d . . . O1 O 0.1868(2) 0.91404(16) 1.04766(17) 0.0352(5) Uani 1 1 d . . . O2 O 0.1763(2) 0.71732(15) 1.10859(15) 0.0267(5) Uani 1 1 d . . . O3 O 0.1148(2) 0.68293(16) 0.73972(16) 0.0349(6) Uani 1 1 d D . . O4 O 0.2204(2) 0.59147(16) 0.92374(16) 0.0280(5) Uani 1 1 d D . . C1 C 0.2319(4) 1.0132(3) 1.0175(3) 0.0475(10) Uani 1 1 d . . . H1A H 0.2120 1.0629 1.0683 0.071 Uiso 1 1 calc R . . H1B H 0.1867 1.0311 0.9493 0.071 Uiso 1 1 calc R . . H1C H 0.3268 1.0114 1.0150 0.071 Uiso 1 1 calc R . . C2 C 0.2508(4) 0.8843(3) 1.1502(3) 0.0415(9) Uani 1 1 d . . . H2A H 0.2499 0.9405 1.1993 0.050 Uiso 1 1 calc R . . H2B H 0.3433 0.8655 1.1462 0.050 Uiso 1 1 calc R . . C3 C 0.1769(4) 0.7964(3) 1.1869(2) 0.0381(9) Uani 1 1 d . . . H3A H 0.2206 0.7725 1.2544 0.046 Uiso 1 1 calc R . . H3B H 0.0859 0.8161 1.1950 0.046 Uiso 1 1 calc R . . C4 C 0.1336(4) 0.6224(2) 1.1514(3) 0.0354(8) Uani 1 1 d . . . H4A H 0.2013 0.5989 1.2059 0.053 Uiso 1 1 calc R . . H4B H 0.1201 0.5723 1.0964 0.053 Uiso 1 1 calc R . . H4C H 0.0513 0.6329 1.1804 0.053 Uiso 1 1 calc R . . C5 C 0.1541(4) 0.7269(3) 0.6461(3) 0.0454(9) Uani 1 1 d . A . H5A H 0.2498 0.7231 0.6488 0.068 Uiso 1 1 calc R . . H5B H 0.1264 0.7968 0.6411 0.068 Uiso 1 1 calc R . . H5C H 0.1126 0.6902 0.5856 0.068 Uiso 1 1 calc R . . C6 C 0.0881(10) 0.5722(6) 0.7548(7) 0.034(3) Uani 0.409(11) 1 d PD A 1 H6A H 0.0096 0.5625 0.7906 0.041 Uiso 0.409(11) 1 calc PR A 1 H6B H 0.0747 0.5368 0.6877 0.041 Uiso 0.409(11) 1 calc PR A 1 C7 C 0.2097(11) 0.5361(8) 0.8201(8) 0.030(3) Uani 0.409(11) 1 d PD A 1 H7A H 0.2879 0.5499 0.7852 0.036 Uiso 0.409(11) 1 calc PR A 1 H7B H 0.2042 0.4633 0.8314 0.036 Uiso 0.409(11) 1 calc PR A 1 C6' C 0.1794(7) 0.5825(4) 0.7394(4) 0.0268(17) Uani 0.591(11) 1 d PD A 2 H6'1 H 0.2751 0.5897 0.7379 0.032 Uiso 0.591(11) 1 calc PR A 2 H6'2 H 0.1418 0.5432 0.6785 0.032 Uiso 0.591(11) 1 calc PR A 2 C7' C 0.1516(8) 0.5318(6) 0.8397(5) 0.0281(17) Uani 0.591(11) 1 d PD A 2 H7'1 H 0.0560 0.5306 0.8442 0.034 Uiso 0.591(11) 1 calc PR A 2 H7'2 H 0.1848 0.4624 0.8429 0.034 Uiso 0.591(11) 1 calc PR A 2 C8 C 0.3478(3) 0.5579(3) 0.9747(3) 0.0349(8) Uani 1 1 d . A . H8A H 0.3411 0.4883 0.9964 0.052 Uiso 1 1 calc R . . H8B H 0.3746 0.5997 1.0353 0.052 Uiso 1 1 calc R . . H8C H 0.4132 0.5630 0.9264 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ce1 0.02087(9) 0.02016(9) 0.01927(8) 0.00141(6) 0.00725(6) 0.00228(7) Br1 0.02290(16) 0.03165(17) 0.02925(16) 0.00274(12) 0.00974(12) -0.00028(13) Br2 0.02358(17) 0.0440(2) 0.02871(17) 0.00706(13) 0.00884(13) -0.00194(14) Br3 0.03331(19) 0.03447(19) 0.04075(19) 0.01472(15) 0.00836(15) 0.01015(14) O1 0.0560(16) 0.0249(12) 0.0285(12) -0.0040(9) 0.0194(11) -0.0035(11) O2 0.0339(12) 0.0273(12) 0.0204(10) 0.0005(9) 0.0092(9) 0.0000(9) O3 0.0589(16) 0.0260(12) 0.0201(11) 0.0011(9) 0.0061(10) 0.0052(11) O4 0.0286(12) 0.0259(12) 0.0285(11) -0.0018(9) -0.0010(9) 0.0057(9) C1 0.076(3) 0.0273(19) 0.044(2) -0.0077(16) 0.0265(19) -0.0101(19) C2 0.051(2) 0.036(2) 0.0369(19) -0.0126(15) 0.0007(17) -0.0030(17) C3 0.057(2) 0.040(2) 0.0171(15) -0.0031(13) 0.0070(15) 0.0026(17) C4 0.044(2) 0.0339(19) 0.0307(17) 0.0124(14) 0.0128(15) 0.0026(16) C5 0.045(2) 0.071(3) 0.0215(17) -0.0021(17) 0.0118(15) -0.004(2) C6 0.041(7) 0.023(4) 0.039(5) -0.007(3) 0.013(4) 0.004(4) C7 0.028(6) 0.019(4) 0.041(6) -0.005(4) 0.002(5) 0.003(5) C6' 0.029(4) 0.028(3) 0.024(3) -0.008(2) 0.007(2) 0.000(2) C7' 0.028(4) 0.027(3) 0.030(3) -0.003(2) 0.007(3) -0.004(3) C8 0.0283(18) 0.038(2) 0.0394(19) 0.0075(15) 0.0066(15) 0.0121(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 Ce1 O2 2.520(2) . ? Ce1 O1 2.519(2) . ? Ce1 O4 2.522(2) . ? Ce1 O3 2.544(2) . ? Ce1 Br3 2.8764(5) . ? Ce1 Br1 2.8828(6) . ? Ce1 Br2 2.8907(6) . ? O1 C2 1.438(4) . ? O1 C1 1.448(4) . ? O2 C4 1.449(4) . ? O2 C3 1.442(4) . ? O3 C5 1.429(4) . ? O3 C6' 1.471(6) . ? O3 C6 1.497(8) . ? O4 C8 1.432(3) . ? O4 C7' 1.434(7) . ? O4 C7 1.503(10) . ? C2 C3 1.481(5) . ? C6 C7 1.468(12) . ? C6' C7' 1.503(9) . ? 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 Ce1 O1 64.95(7) . . ? O2 Ce1 O4 71.99(6) . . ? O1 Ce1 O4 129.16(7) . . ? O2 Ce1 O3 136.17(7) . . ? O1 Ce1 O3 155.88(7) . . ? O4 Ce1 O3 65.28(7) . . ? O2 Ce1 Br3 141.50(5) . . ? O1 Ce1 Br3 84.13(6) . . ? O4 Ce1 Br3 145.19(5) . . ? O3 Ce1 Br3 79.94(5) . . ? O2 Ce1 Br1 99.92(5) . . ? O1 Ce1 Br1 80.32(5) . . ? O4 Ce1 Br1 81.77(5) . . ? O3 Ce1 Br1 83.64(6) . . ? Br3 Ce1 Br1 96.627(13) . . ? O2 Ce1 Br2 78.74(5) . . ? O1 Ce1 Br2 109.36(5) . . ? O4 Ce1 Br2 86.54(5) . . ? O3 Ce1 Br2 89.15(6) . . ? Br3 Ce1 Br2 91.498(15) . . ? Br1 Ce1 Br2 168.021(11) . . ? C2 O1 C1 111.6(3) . . ? C2 O1 Ce1 115.57(18) . . ? C1 O1 Ce1 123.13(18) . . ? C4 O2 C3 109.5(2) . . ? C4 O2 Ce1 125.56(18) . . ? C3 O2 Ce1 116.90(17) . . ? C5 O3 C6' 101.0(3) . . ? C5 O3 C6 125.1(4) . . ? C6' O3 C6 38.3(4) . . ? C5 O3 Ce1 124.9(2) . . ? C6' O3 Ce1 115.6(2) . . ? C6 O3 Ce1 108.6(3) . . ? C8 O4 C7' 119.4(4) . . ? C8 O4 C7 102.2(4) . . ? C7' O4 C7 26.1(3) . . ? C8 O4 Ce1 126.54(19) . . ? C7' O4 Ce1 110.8(3) . . ? C7 O4 Ce1 116.3(4) . . ? O1 C2 C3 108.4(3) . . ? O2 C3 C2 107.5(3) . . ? C7 C6 O3 103.7(8) . . ? C6 C7 O4 107.8(7) . . ? O3 C6' C7' 105.4(5) . . ? O4 C7' C6' 105.8(5) . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.191 _refine_diff_density_min -0.804 _refine_diff_density_rms 0.103 # Attachment '- 845798.cif' data_apx1339 _database_code_depnum_ccdc_archive 'CCDC 845798' #TrackingRef '- 845798.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H22 Br3 Ce O4' _chemical_formula_weight 586.13 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.493(2) _cell_length_b 19.263(5) _cell_length_c 12.710(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.926(3) _cell_angle_gamma 90.00 _cell_volume 1780.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 140(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1108 _exptl_absorpt_coefficient_mu 9.291 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2856 _exptl_absorpt_correction_T_max 0.8360 _exptl_absorpt_process_details 'SADABS v. 1 (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker D8 with APEXII CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17540 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.76 _reflns_number_total 3402 _reflns_number_gt 2615 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II, v. 7.0 (Bruker AXS, 2009)' _computing_cell_refinement 'SAINT+, v. 7.66a (Bruker AXS, 2009)' _computing_data_reduction 'SAINT+, v. 7.66a (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, v. 6.14, (Bruker AXS, 2000)' _computing_publication_material 'SHELXTL, v. 6.14, (Bruker AXS, 2000)' _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^)+(0.0403P)^2^+6.6447P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3402 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0544 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0743 _refine_ls_wR_factor_gt 0.0647 _refine_ls_goodness_of_fit_ref 0.849 _refine_ls_restrained_S_all 0.849 _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 Ce1 Ce 0.29825(4) 0.111174(17) 0.77095(3) 0.01261(10) Uani 1 1 d . . . Br1 Br 0.33186(10) 0.13866(3) 0.55056(5) 0.02737(17) Uani 1 1 d . . . Br2 Br 0.18682(8) 0.15418(3) 0.96605(5) 0.01644(15) Uani 1 1 d . . . Br3 Br 0.12091(8) -0.02089(3) 0.79125(5) 0.01918(15) Uani 1 1 d . . . O1 O 0.5193(6) 0.0148(2) 0.7311(3) 0.0174(9) Uani 1 1 d . . . O2 O 0.5892(5) 0.0807(2) 0.9218(3) 0.0172(9) Uani 1 1 d . . . O3 O 0.5330(5) 0.2075(2) 0.8277(3) 0.0209(10) Uani 1 1 d . . . O4 O 0.1959(5) 0.2402(2) 0.7272(3) 0.0183(9) Uani 1 1 d . . . O5 O -0.0427(5) 0.1341(2) 0.6676(3) 0.0197(10) Uani 1 1 d . . . C1 C 0.4677(10) -0.0312(3) 0.6408(5) 0.0251(15) Uani 1 1 d . . . H1A H 0.5760 -0.0514 0.6257 0.038 Uiso 1 1 calc R . . H1B H 0.4019 -0.0058 0.5785 0.038 Uiso 1 1 calc R . . H1C H 0.3905 -0.0673 0.6574 0.038 Uiso 1 1 calc R . . C2 C 0.6187(8) -0.0225(3) 0.8257(5) 0.0194(14) Uani 1 1 d . . . H2A H 0.7027 -0.0556 0.8061 0.023 Uiso 1 1 calc R . . H2B H 0.5340 -0.0474 0.8590 0.023 Uiso 1 1 calc R . . C3 C 0.7227(8) 0.0308(3) 0.9023(5) 0.0196(14) Uani 1 1 d . . . H3A H 0.7864 0.0091 0.9698 0.024 Uiso 1 1 calc R . . H3B H 0.8128 0.0537 0.8707 0.024 Uiso 1 1 calc R . . C4 C 0.6818(8) 0.1413(3) 0.9794(5) 0.0169(13) Uani 1 1 d . . . H4A H 0.7988 0.1278 1.0263 0.020 Uiso 1 1 calc R . . H4B H 0.6068 0.1616 1.0239 0.020 Uiso 1 1 calc R . . C5 C 0.7115(8) 0.1931(3) 0.8972(5) 0.0211(14) Uani 1 1 d . . . H5A H 0.7662 0.2352 0.9327 0.025 Uiso 1 1 calc R . . H5B H 0.7927 0.1741 0.8554 0.025 Uiso 1 1 calc R . . C6 C 0.5041(8) 0.2760(3) 0.7842(5) 0.0218(14) Uani 1 1 d . . . H6A H 0.5212 0.2771 0.7110 0.026 Uiso 1 1 calc R . . H6B H 0.5900 0.3082 0.8284 0.026 Uiso 1 1 calc R . . C7 C 0.3098(8) 0.2951(3) 0.7847(5) 0.0203(14) Uani 1 1 d . . . H7A H 0.2957 0.2986 0.8584 0.024 Uiso 1 1 calc R . . H7B H 0.2766 0.3393 0.7486 0.024 Uiso 1 1 calc R . . C8 C 0.0042(8) 0.2541(3) 0.7133(5) 0.0201(14) Uani 1 1 d . . . H8A H -0.0241 0.3011 0.6873 0.024 Uiso 1 1 calc R . . H8B H -0.0307 0.2488 0.7815 0.024 Uiso 1 1 calc R . . C9 C -0.0973(8) 0.2025(3) 0.6313(5) 0.0243(15) Uani 1 1 d . . . H9A H -0.2288 0.2078 0.6225 0.029 Uiso 1 1 calc R . . H9B H -0.0694 0.2107 0.5617 0.029 Uiso 1 1 calc R . . C10 C -0.1390(9) 0.0859(3) 0.5872(6) 0.0296(17) Uani 1 1 d . . . H10A H -0.2682 0.0961 0.5702 0.044 Uiso 1 1 calc R . . H10B H -0.1191 0.0394 0.6149 0.044 Uiso 1 1 calc R . . H10C H -0.0940 0.0900 0.5228 0.044 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ce1 0.01416(18) 0.00978(17) 0.01251(17) 0.00025(14) 0.00050(13) 0.00032(14) Br1 0.0427(4) 0.0235(4) 0.0181(3) 0.0057(3) 0.0115(3) 0.0111(3) Br2 0.0168(3) 0.0162(3) 0.0152(3) -0.0018(2) 0.0017(2) 0.0007(2) Br3 0.0209(3) 0.0125(3) 0.0237(3) 0.0005(3) 0.0046(3) -0.0014(2) O1 0.025(2) 0.014(2) 0.012(2) -0.0017(17) 0.0027(18) -0.0023(18) O2 0.018(2) 0.016(2) 0.017(2) -0.0034(18) 0.0028(18) -0.0021(18) O3 0.016(2) 0.013(2) 0.029(3) 0.0014(19) -0.0046(19) -0.0031(17) O4 0.018(2) 0.015(2) 0.019(2) -0.0009(18) -0.0007(18) -0.0009(18) O5 0.019(2) 0.016(2) 0.018(2) 0.0031(18) -0.0077(18) -0.0012(18) C1 0.042(4) 0.015(3) 0.019(3) -0.006(3) 0.008(3) 0.001(3) C2 0.018(3) 0.019(3) 0.019(3) 0.005(3) -0.001(3) 0.004(3) C3 0.012(3) 0.017(3) 0.028(4) -0.005(3) 0.002(3) 0.002(3) C4 0.018(3) 0.015(3) 0.015(3) -0.004(3) -0.003(3) 0.005(3) C5 0.018(3) 0.023(3) 0.023(3) -0.001(3) 0.005(3) -0.006(3) C6 0.025(3) 0.013(3) 0.025(4) 0.003(3) 0.002(3) -0.008(3) C7 0.024(3) 0.011(3) 0.022(3) 0.001(3) -0.001(3) -0.001(3) C8 0.019(3) 0.017(3) 0.024(3) 0.002(3) 0.003(3) 0.001(3) C9 0.018(3) 0.020(4) 0.031(4) 0.003(3) -0.002(3) 0.004(3) C10 0.026(4) 0.022(4) 0.032(4) -0.004(3) -0.010(3) -0.003(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 Ce1 O3 2.540(4) . ? Ce1 O2 2.600(4) . ? Ce1 O4 2.620(4) . ? Ce1 O5 2.613(4) . ? Ce1 O1 2.618(4) . ? Ce1 Br3 2.9102(9) . ? Ce1 Br2 2.9205(9) . ? Ce1 Br1 2.9206(10) . ? O1 C1 1.428(7) . ? O1 C2 1.443(7) . ? O2 C3 1.451(7) . ? O2 C4 1.461(7) . ? O3 C6 1.426(7) . ? O3 C5 1.441(7) . ? O4 C8 1.430(7) . ? O4 C7 1.443(7) . ? O5 C9 1.423(7) . ? O5 C10 1.441(7) . ? C2 C3 1.498(8) . ? C4 C5 1.499(8) . ? C6 C7 1.503(8) . ? C8 C9 1.507(9) . ? 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 Ce1 O2 63.58(13) . . ? O3 Ce1 O4 60.95(12) . . ? O2 Ce1 O4 121.40(12) . . ? O3 Ce1 O5 123.07(13) . . ? O2 Ce1 O5 162.41(13) . . ? O4 Ce1 O5 62.12(12) . . ? O3 Ce1 O1 98.40(13) . . ? O2 Ce1 O1 61.65(12) . . ? O4 Ce1 O1 142.97(12) . . ? O5 Ce1 O1 127.61(13) . . ? O3 Ce1 Br3 156.01(9) . . ? O2 Ce1 Br3 93.27(9) . . ? O4 Ce1 Br3 136.99(9) . . ? O5 Ce1 Br3 77.31(9) . . ? O1 Ce1 Br3 73.78(9) . . ? O3 Ce1 Br2 82.62(10) . . ? O2 Ce1 Br2 78.36(9) . . ? O4 Ce1 Br2 77.42(9) . . ? O5 Ce1 Br2 86.22(10) . . ? O1 Ce1 Br2 133.54(9) . . ? Br3 Ce1 Br2 86.72(2) . . ? O3 Ce1 Br1 85.76(10) . . ? O2 Ce1 Br1 119.84(9) . . ? O4 Ce1 Br1 73.32(9) . . ? O5 Ce1 Br1 77.70(10) . . ? O1 Ce1 Br1 74.85(9) . . ? Br3 Ce1 Br1 112.96(2) . . ? Br2 Ce1 Br1 150.60(2) . . ? C1 O1 C2 110.3(5) . . ? C1 O1 Ce1 122.3(4) . . ? C2 O1 Ce1 114.5(3) . . ? C3 O2 C4 110.6(4) . . ? C3 O2 Ce1 120.9(3) . . ? C4 O2 Ce1 113.7(3) . . ? C6 O3 C5 116.6(4) . . ? C6 O3 Ce1 122.4(3) . . ? C5 O3 Ce1 120.6(3) . . ? C8 O4 C7 112.3(4) . . ? C8 O4 Ce1 116.0(3) . . ? C7 O4 Ce1 118.7(3) . . ? C9 O5 C10 108.1(4) . . ? C9 O5 Ce1 119.3(3) . . ? C10 O5 Ce1 120.7(4) . . ? O1 C2 C3 106.5(5) . . ? O2 C3 C2 107.0(5) . . ? O2 C4 C5 108.3(5) . . ? O3 C5 C4 106.5(5) . . ? O3 C6 C7 106.4(5) . . ? O4 C7 C6 105.9(5) . . ? O4 C8 C9 106.6(5) . . ? O5 C9 C8 109.2(5) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.733 _refine_diff_density_min -0.825 _refine_diff_density_rms 0.163