# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_yci_ht8run_0m _database_code_depnum_ccdc_archive 'CCDC 893150' #TrackingRef 'web_deposit_cif_file_4_Chen-IYang_1343022745.JZR0003-8(Gd).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H22 Gd N O9' _chemical_formula_weight 481.56 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' Gd Gd -0.1653 3.9035 '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)/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 10.1940(13) _cell_length_b 13.2638(17) _cell_length_c 12.8106(16) _cell_angle_alpha 90.00 _cell_angle_beta 106.048(2) _cell_angle_gamma 90.00 _cell_volume 1664.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7644 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 28.34 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.921 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 948 _exptl_absorpt_coefficient_mu 4.028 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5765 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12103 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 28.35 _reflns_number_total 4156 _reflns_number_gt 3736 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+23.1684P] 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 4156 _refine_ls_number_parameters 207 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1163 _refine_ls_wR_factor_gt 0.1146 _refine_ls_goodness_of_fit_ref 1.256 _refine_ls_restrained_S_all 1.256 _refine_ls_shift/su_max 0.068 _refine_ls_shift/su_mean 0.002 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 Gd1 Gd 0.15474(3) 1.00286(3) -0.07757(3) 0.01993(10) Uani 1 1 d . . . O5 O 0.2092(7) 0.8559(5) -0.1838(5) 0.0439(16) Uani 1 1 d . . . O1 O 0.1125(8) 0.8601(6) 0.0094(6) 0.054(2) Uani 1 1 d . . . O6 O 0.3766(6) 0.9076(5) -0.0485(5) 0.0328(13) Uani 1 1 d . . . O7 O 0.3949(9) 0.7666(6) -0.1331(6) 0.060(2) Uani 1 1 d . . . C1 C 0.0476(8) 0.8095(6) 0.0588(6) 0.0250(15) Uani 1 1 d . . . O8 O 0.3447(6) 1.1208(5) -0.0643(5) 0.0374(15) Uani 1 1 d . . . N1 N 0.3290(8) 0.8410(6) -0.1224(6) 0.0341(16) Uani 1 1 d . . . O2 O 0.0508(6) 1.1589(5) -0.0902(6) 0.0442(16) Uani 1 1 d . . . O4 O -0.0610(7) 0.9625(5) -0.1808(8) 0.070(3) Uani 1 1 d . . . O9 O 0.1522(11) 1.0653(6) -0.2601(5) 0.058(2) Uani 1 1 d D . . C2 C 0.0900(8) 0.6996(6) 0.0849(6) 0.0277(16) Uani 1 1 d . . . O3 O 0.2299(11) 1.0423(6) 0.1026(5) 0.071(3) Uani 1 1 d . . . C6 C -0.0162(13) 0.6340(9) 0.1244(12) 0.069(4) Uani 1 1 d . . . H6A H -0.0658 0.6753 0.1630 0.083 Uiso 1 1 calc R . . H6B H -0.0810 0.6025 0.0630 0.083 Uiso 1 1 calc R . . C8 C 0.106(3) 0.6446(15) -0.0066(18) 0.052(5) Uani 0.50 1 d P . . H8A H 0.0180 0.6361 -0.0583 0.079 Uiso 0.50 1 calc PR . . H8B H 0.1443 0.5797 0.0166 0.079 Uiso 0.50 1 calc PR . . H8C H 0.1649 0.6810 -0.0398 0.079 Uiso 0.50 1 calc PR . . C7 C 0.1851(10) 1.0499(6) 0.1820(6) 0.034(2) Uani 1 1 d . . . C4 C 0.2802(8) 1.0762(6) 0.2904(6) 0.0265(16) Uani 1 1 d . . . C10 C 0.2050(16) 0.7520(8) 0.2805(8) 0.086(7) Uani 1.00(4) 1 d . . . H10A H 0.1924 0.8217 0.2600 0.129 Uiso 1 1 calc R . . H10B H 0.2877 0.7445 0.3382 0.129 Uiso 1 1 calc R . . H10C H 0.1290 0.7292 0.3048 0.129 Uiso 1 1 calc R . . C3 C 0.2142(12) 0.6906(8) 0.1847(8) 0.051(3) Uani 1 1 d . . . C12 C 0.1247(16) 1.0204(12) -0.3604(12) 0.081(4) Uiso 1 1 d . . . H12A H 0.2024 1.0274 -0.3885 0.121 Uiso 1 1 calc R . . H12B H 0.0470 1.0523 -0.4089 0.121 Uiso 1 1 calc R . . H12C H 0.1057 0.9502 -0.3539 0.121 Uiso 1 1 calc R . . C5 C 0.0702(13) 0.5525(11) 0.2013(11) 0.069(3) Uiso 1 1 d . . . H5A H 0.0540 0.5556 0.2724 0.083 Uiso 1 1 calc R . . H5B H 0.0465 0.4855 0.1715 0.083 Uiso 1 1 calc R . . C11 C 0.3456(15) 1.2267(11) -0.0819(12) 0.074(4) Uiso 1 1 d . . . H11A H 0.3139 1.2404 -0.1583 0.112 Uiso 1 1 calc R . . H11B H 0.4368 1.2520 -0.0538 0.112 Uiso 1 1 calc R . . H11C H 0.2866 1.2592 -0.0453 0.112 Uiso 1 1 calc R . . C9 C 0.3476(15) 0.7202(12) 0.1516(12) 0.079(4) Uiso 1 1 d . . . H9A H 0.3482 0.7916 0.1394 0.118 Uiso 1 1 calc R . . H9B H 0.3489 0.6851 0.0864 0.118 Uiso 1 1 calc R . . H9C H 0.4266 0.7018 0.2090 0.118 Uiso 1 1 calc R . . C8' C 0.258(3) 1.021(2) 0.384(2) 0.065(6) Uiso 0.50 1 d P . . H8'1 H 0.1657 1.0316 0.3869 0.098 Uiso 0.50 1 calc PR . . H8'2 H 0.3201 1.0453 0.4497 0.098 Uiso 0.50 1 calc PR . . H8'3 H 0.2728 0.9503 0.3760 0.098 Uiso 0.50 1 calc PR . . H8 H 0.431(15) 1.114(12) -0.016(12) 0.10(5) Uiso 1 1 d . . . H9 H 0.218(19) 1.07(2) -0.28(2) 0.29(17) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Gd1 0.01744(16) 0.02029(17) 0.02015(16) 0.00082(15) 0.00202(11) -0.00018(14) O5 0.050(4) 0.051(4) 0.029(3) -0.018(3) 0.007(3) 0.009(3) O1 0.071(5) 0.051(4) 0.035(4) 0.014(3) 0.007(3) -0.024(4) O6 0.028(3) 0.037(3) 0.031(3) -0.007(3) 0.005(2) 0.002(2) O7 0.075(5) 0.053(5) 0.049(4) -0.011(4) 0.010(4) 0.031(4) C1 0.028(4) 0.025(4) 0.015(3) 0.000(3) -0.007(3) -0.001(3) O8 0.022(3) 0.039(3) 0.044(4) 0.019(3) -0.001(3) -0.006(2) N1 0.039(4) 0.041(4) 0.025(3) -0.003(3) 0.013(3) 0.007(3) O2 0.030(3) 0.039(4) 0.054(4) -0.009(3) -0.003(3) 0.012(3) O4 0.029(3) 0.037(4) 0.117(7) -0.008(4) -0.025(4) -0.005(3) O9 0.108(7) 0.048(4) 0.022(3) -0.003(3) 0.021(4) -0.016(4) C2 0.034(4) 0.026(4) 0.018(3) -0.001(3) -0.001(3) 0.005(3) O3 0.141(8) 0.052(5) 0.021(3) -0.018(3) 0.022(4) -0.032(5) C6 0.053(7) 0.050(7) 0.100(11) 0.001(7) 0.014(7) -0.005(6) C8 0.077(15) 0.029(9) 0.053(12) -0.014(9) 0.021(11) -0.001(10) C7 0.052(5) 0.018(4) 0.021(4) -0.001(3) -0.011(4) -0.007(3) C4 0.033(4) 0.029(4) 0.015(3) -0.004(3) 0.002(3) -0.003(3) C10 0.151(14) 0.034(6) 0.025(5) -0.019(4) -0.055(7) 0.030(7) C3 0.060(6) 0.039(5) 0.037(5) 0.008(4) -0.014(5) -0.003(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 Gd1 O3 2.282(6) . ? Gd1 O4 2.294(6) . ? Gd1 O1 2.297(6) . ? Gd1 O2 2.310(6) . ? Gd1 O8 2.458(6) . ? Gd1 O9 2.474(7) . ? Gd1 O5 2.525(6) . ? Gd1 O6 2.527(6) . ? Gd1 N1 2.942(7) . ? O5 N1 1.272(9) . ? O1 C1 1.233(10) . ? O6 N1 1.287(9) . ? O7 N1 1.224(10) . ? C1 O2 1.252(10) 3_575 ? C1 C2 1.531(10) . ? O8 C11 1.424(15) . ? O2 C1 1.252(10) 3_575 ? O4 C7 1.272(12) 3_575 ? O9 C12 1.373(16) . ? C2 C8 1.43(2) . ? C2 C3 1.535(12) . ? C2 C6 1.577(15) . ? O3 C7 1.229(12) . ? C6 C5 1.560(18) . ? C7 O4 1.272(12) 3_575 ? C7 C4 1.499(10) . ? C4 C8' 1.47(3) . ? C4 C5 1.531(15) 2 ? C4 C3 1.549(12) 2 ? C10 C3 1.497(15) . ? C3 C4 1.549(12) 2_545 ? C3 C9 1.581(18) . ? C5 C4 1.531(15) 2_545 ? 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 Gd1 O4 129.5(4) . . ? O3 Gd1 O1 75.8(3) . . ? O4 Gd1 O1 79.0(3) . . ? O3 Gd1 O2 83.4(3) . . ? O4 Gd1 O2 79.7(2) . . ? O1 Gd1 O2 129.0(3) . . ? O3 Gd1 O8 75.3(3) . . ? O4 Gd1 O8 143.1(3) . . ? O1 Gd1 O8 137.8(2) . . ? O2 Gd1 O8 76.8(2) . . ? O3 Gd1 O9 142.4(3) . . ? O4 Gd1 O9 77.0(3) . . ? O1 Gd1 O9 141.3(3) . . ? O2 Gd1 O9 75.4(3) . . ? O8 Gd1 O9 69.8(3) . . ? O3 Gd1 O5 131.3(3) . . ? O4 Gd1 O5 80.1(3) . . ? O1 Gd1 O5 74.0(3) . . ? O2 Gd1 O5 144.9(2) . . ? O8 Gd1 O5 104.0(2) . . ? O9 Gd1 O5 72.3(3) . . ? O3 Gd1 O6 85.9(3) . . ? O4 Gd1 O6 130.2(2) . . ? O1 Gd1 O6 78.3(3) . . ? O2 Gd1 O6 146.4(2) . . ? O8 Gd1 O6 69.6(2) . . ? O9 Gd1 O6 94.7(3) . . ? O5 Gd1 O6 51.1(2) . . ? O3 Gd1 N1 108.2(3) . . ? O4 Gd1 N1 104.6(3) . . ? O1 Gd1 N1 72.4(3) . . ? O2 Gd1 N1 158.4(2) . . ? O8 Gd1 N1 88.4(2) . . ? O9 Gd1 N1 84.8(3) . . ? O5 Gd1 N1 25.5(2) . . ? O6 Gd1 N1 25.83(19) . . ? N1 O5 Gd1 95.9(4) . . ? C1 O1 Gd1 153.7(7) . . ? N1 O6 Gd1 95.4(4) . . ? O1 C1 O2 125.1(8) . 3_575 ? O1 C1 C2 118.1(8) . . ? O2 C1 C2 116.8(7) 3_575 . ? C11 O8 Gd1 131.0(7) . . ? O7 N1 O5 121.2(8) . . ? O7 N1 O6 122.0(8) . . ? O5 N1 O6 116.8(7) . . ? O7 N1 Gd1 172.2(7) . . ? O5 N1 Gd1 58.6(4) . . ? O6 N1 Gd1 58.8(4) . . ? C1 O2 Gd1 132.0(6) 3_575 . ? C7 O4 Gd1 146.0(8) 3_575 . ? C12 O9 Gd1 133.3(8) . . ? C8 C2 C1 113.3(10) . . ? C8 C2 C3 113.0(12) . . ? C1 C2 C3 112.0(7) . . ? C8 C2 C6 102.9(12) . . ? C1 C2 C6 114.7(8) . . ? C3 C2 C6 99.9(8) . . ? C7 O3 Gd1 139.3(8) . . ? C5 C6 C2 105.5(9) . . ? O3 C7 O4 125.1(9) . 3_575 ? O3 C7 C4 119.5(9) . . ? O4 C7 C4 115.3(9) 3_575 . ? C8' C4 C7 115.6(12) . . ? C8' C4 C5 102.5(12) . 2 ? C7 C4 C5 113.1(8) . 2 ? C8' C4 C3 108.9(12) . 2 ? C7 C4 C3 113.3(7) . 2 ? C5 C4 C3 102.0(8) 2 2 ? C10 C3 C2 114.6(9) . . ? C10 C3 C4 111.8(9) . 2_545 ? C2 C3 C4 102.9(7) . 2_545 ? C10 C3 C9 109.8(11) . . ? C2 C3 C9 109.2(9) . . ? C4 C3 C9 108.2(10) 2_545 . ? C4 C5 C6 106.2(10) 2_545 . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.357 _refine_diff_density_min -1.037 _refine_diff_density_rms 0.160 data_yci0006_11_run_0m _database_code_depnum_ccdc_archive 'CCDC 893151' #TrackingRef 'web_deposit_cif_file_5_Chen-IYang_1343022745.JZL-0006-11(Tb).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H22 N O9 Tb' _chemical_formula_weight 483.23 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' Tb Tb -0.1723 4.1537 '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)/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 10.2870(7) _cell_length_b 13.2402(9) _cell_length_c 12.8956(9) _cell_angle_alpha 90.00 _cell_angle_beta 106.5960(10) _cell_angle_gamma 90.00 _cell_volume 1683.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8166 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 30.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.907 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 4.245 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6167 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13752 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 30.50 _reflns_number_total 4896 _reflns_number_gt 4301 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0021P)^2^+8.6601P] 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 4896 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.0781 _refine_ls_wR_factor_gt 0.0765 _refine_ls_goodness_of_fit_ref 1.216 _refine_ls_restrained_S_all 1.216 _refine_ls_shift/su_max 0.004 _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 Tb1 Tb 0.653862(19) 1.003450(15) -0.076828(15) 0.01954(6) Uani 1 1 d . . . O6 O 0.7083(4) 0.8586(3) -0.1815(3) 0.0436(10) Uani 1 1 d . . . O1 O 0.6143(5) 0.8613(3) 0.0104(3) 0.0498(11) Uani 1 1 d . . . O9 O 0.8424(4) 1.1200(3) -0.0635(4) 0.0414(10) Uani 1 1 d . . . N1 N 0.8270(5) 0.8436(3) -0.1214(4) 0.0354(10) Uani 1 1 d . . . O8 O 0.6428(5) 1.0664(4) -0.2592(3) 0.0502(12) Uani 1 1 d . . . O5 O 0.8748(4) 0.9088(3) -0.0480(3) 0.0374(9) Uani 1 1 d . . . O3 O 0.7284(6) 1.0437(4) 0.1017(3) 0.0583(13) Uani 1 1 d . . . O7 O 0.8931(5) 0.7696(4) -0.1327(4) 0.0697(16) Uani 1 1 d . . . O2 O 0.4506(4) 0.8425(3) 0.0892(4) 0.0439(10) Uani 1 1 d . . . C1 C 0.5500(5) 0.8103(3) 0.0601(4) 0.0251(9) Uani 1 1 d . . . O4 O 0.4402(4) 0.9606(3) -0.1770(4) 0.0585(13) Uani 1 1 d . . . C2 C 0.5930(5) 0.7016(3) 0.0864(4) 0.0260(9) Uani 1 1 d . . . C4 C 0.7219(5) 0.5778(4) 0.2103(4) 0.0272(9) Uani 1 1 d . . . C7 C 0.6816(5) 1.0516(3) 0.1799(4) 0.0303(10) Uani 1 1 d . . . C3 C 0.7170(7) 0.6928(5) 0.1873(5) 0.0538(18) Uani 1 1 d . . . C10 C 0.7058(9) 0.7544(5) 0.2800(5) 0.073(3) Uani 1 1 d . . . H10A H 0.6968 0.8243 0.2595 0.109 Uiso 1 1 calc R . . H10B H 0.7858 0.7454 0.3397 0.109 Uiso 1 1 calc R . . H10C H 0.6276 0.7335 0.3010 0.109 Uiso 1 1 calc R . . C6 C 0.4879(8) 0.6347(6) 0.1214(8) 0.069(2) Uani 1 1 d . . . H6A H 0.4263 0.6025 0.0589 0.083 Uiso 1 1 calc R . . H6B H 0.4354 0.6753 0.1575 0.083 Uiso 1 1 calc R . . C12 C 0.8437(8) 1.2253(6) -0.0854(7) 0.073(3) Uani 1 1 d . . . H12A H 0.8296 1.2355 -0.1615 0.110 Uiso 1 1 calc R . . H12B H 0.9297 1.2534 -0.0461 0.110 Uiso 1 1 calc R . . H12C H 0.7726 1.2581 -0.0634 0.110 Uiso 1 1 calc R . . C5 C 0.5733(7) 0.5535(6) 0.2008(7) 0.066(2) Uani 1 1 d . . . H5A H 0.5565 0.5578 0.2709 0.080 Uiso 1 1 calc R . . H5B H 0.5504 0.4860 0.1720 0.080 Uiso 1 1 calc R . . C9 C 0.8500(8) 0.7240(8) 0.1564(9) 0.094(3) Uani 1 1 d . . . H9A H 0.8591 0.7961 0.1591 0.140 Uiso 1 1 calc R . . H9B H 0.8437 0.7006 0.0847 0.140 Uiso 1 1 calc R . . H9C H 0.9276 0.6940 0.2068 0.140 Uiso 1 1 calc R . . C11 C 0.6361(16) 1.0244(8) -0.3565(7) 0.128(5) Uani 1 1 d . . . H11A H 0.7222 1.0315 -0.3709 0.192 Uiso 1 1 calc R . . H11B H 0.5674 1.0580 -0.4121 0.192 Uiso 1 1 calc R . . H11C H 0.6140 0.9541 -0.3553 0.192 Uiso 1 1 calc R . . C8 C 0.6116(18) 0.6481(10) -0.0087(12) 0.063(4) Uani 0.50 1 d P . . H8A H 0.5282 0.6494 -0.0662 0.094 Uiso 0.50 1 calc PR . . H8B H 0.6372 0.5794 0.0103 0.094 Uiso 0.50 1 calc PR . . H8C H 0.6815 0.6808 -0.0322 0.094 Uiso 0.50 1 calc PR . . C8' C 0.7528(18) 0.5300(16) 0.1171(10) 0.083(6) Uani 0.50 1 d P . . H8'1 H 0.8461 0.5420 0.1209 0.124 Uiso 0.50 1 calc PR . . H8'2 H 0.6955 0.5582 0.0513 0.124 Uiso 0.50 1 calc PR . . H8'3 H 0.7371 0.4586 0.1183 0.124 Uiso 0.50 1 calc PR . . H9 H 0.900(7) 1.110(5) -0.027(5) 0.04(2) Uiso 1 1 d . . . H8 H 0.640(9) 1.128(7) -0.266(7) 0.09(3) 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 Tb1 0.01776(9) 0.02088(10) 0.01942(9) 0.00032(8) 0.00438(6) 0.00013(8) O6 0.044(2) 0.050(2) 0.032(2) -0.0153(18) 0.0045(17) 0.0104(19) O1 0.070(3) 0.039(2) 0.041(2) 0.0103(18) 0.017(2) -0.017(2) O9 0.0220(19) 0.044(2) 0.052(3) 0.018(2) 0.0011(18) -0.0058(16) N1 0.038(2) 0.037(2) 0.034(2) -0.0041(19) 0.0142(19) 0.0084(19) O8 0.084(4) 0.043(2) 0.027(2) 0.0037(18) 0.022(2) -0.004(2) O5 0.0273(18) 0.040(2) 0.043(2) -0.0106(17) 0.0072(16) 0.0027(15) O3 0.098(4) 0.054(3) 0.024(2) -0.0131(18) 0.020(2) -0.024(3) O7 0.074(3) 0.058(3) 0.069(3) -0.023(3) 0.006(3) 0.036(3) O2 0.031(2) 0.035(2) 0.061(3) -0.0056(19) 0.0053(18) 0.0114(16) C1 0.029(2) 0.0201(19) 0.019(2) 0.0011(15) -0.0038(17) 0.0010(16) O4 0.024(2) 0.046(2) 0.088(4) -0.010(2) -0.011(2) -0.0074(17) C2 0.031(2) 0.022(2) 0.022(2) 0.0025(16) 0.0026(18) 0.0041(17) C4 0.033(2) 0.026(2) 0.019(2) 0.0038(17) 0.0018(18) 0.0047(18) C7 0.038(3) 0.021(2) 0.024(2) -0.0005(17) -0.0030(19) -0.0060(18) C3 0.060(4) 0.036(3) 0.044(3) 0.008(3) -0.019(3) -0.001(3) C10 0.105(6) 0.040(3) 0.040(4) -0.012(3) -0.034(4) 0.017(4) C6 0.050(4) 0.053(4) 0.098(6) 0.008(4) 0.009(4) -0.005(3) C12 0.056(4) 0.056(4) 0.094(6) 0.038(4) -0.003(4) -0.020(3) C5 0.054(4) 0.066(5) 0.071(5) 0.010(4) 0.004(4) -0.013(4) C9 0.052(5) 0.097(7) 0.134(9) 0.053(7) 0.031(5) -0.007(5) C11 0.278(17) 0.071(6) 0.046(5) 0.012(4) 0.064(7) 0.023(8) C8 0.107(13) 0.033(6) 0.056(8) -0.012(6) 0.037(8) 0.008(7) C8' 0.084(12) 0.140(17) 0.021(6) -0.024(8) 0.010(6) -0.005(11) _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 Tb1 O3 2.272(4) . ? Tb1 O4 2.280(4) . ? Tb1 O1 2.288(4) . ? Tb1 O2 2.290(4) 3_675 ? Tb1 O9 2.446(4) . ? Tb1 O8 2.467(4) . ? Tb1 O6 2.499(4) . ? Tb1 O5 2.529(4) . ? Tb1 N1 2.927(4) . ? O6 N1 1.262(6) . ? O1 C1 1.243(6) . ? O9 C12 1.423(8) . ? N1 O7 1.224(6) . ? N1 O5 1.272(6) . ? O8 C11 1.356(9) . ? O3 C7 1.239(7) . ? O2 C1 1.260(6) . ? O2 Tb1 2.290(4) 3_675 ? C1 C2 1.515(6) . ? O4 C7 1.253(7) 3_675 ? C2 C8 1.476(13) . ? C2 C3 1.545(7) . ? C2 C6 1.560(9) . ? C4 C8' 1.471(14) . ? C4 C7 1.519(6) 2_645 ? C4 C5 1.532(9) . ? C4 C3 1.550(7) . ? C7 O4 1.253(7) 3_675 ? C7 C4 1.519(6) 2_655 ? C3 C10 1.479(10) . ? C3 C9 1.585(11) . ? C6 C5 1.570(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 O3 Tb1 O4 128.6(2) . . ? O3 Tb1 O1 75.54(16) . . ? O4 Tb1 O1 78.22(17) . . ? O3 Tb1 O2 82.96(17) . 3_675 ? O4 Tb1 O2 79.91(15) . 3_675 ? O1 Tb1 O2 128.40(17) . 3_675 ? O3 Tb1 O9 75.50(17) . . ? O4 Tb1 O9 144.45(17) . . ? O1 Tb1 O9 137.15(15) . . ? O2 Tb1 O9 77.86(15) 3_675 . ? O3 Tb1 O8 142.85(16) . . ? O4 Tb1 O8 76.69(19) . . ? O1 Tb1 O8 141.32(16) . . ? O2 Tb1 O8 74.91(16) 3_675 . ? O9 Tb1 O8 70.95(16) . . ? O3 Tb1 O6 131.63(16) . . ? O4 Tb1 O6 80.31(16) . . ? O1 Tb1 O6 74.51(16) . . ? O2 Tb1 O6 145.00(15) 3_675 . ? O9 Tb1 O6 103.12(16) . . ? O8 Tb1 O6 72.61(15) . . ? O3 Tb1 O5 86.47(17) . . ? O4 Tb1 O5 129.85(15) . . ? O1 Tb1 O5 78.39(16) . . ? O2 Tb1 O5 146.72(14) 3_675 . ? O9 Tb1 O5 68.95(14) . . ? O8 Tb1 O5 95.87(16) . . ? O6 Tb1 O5 50.83(12) . . ? O3 Tb1 N1 108.67(17) . . ? O4 Tb1 N1 104.55(15) . . ? O1 Tb1 N1 72.85(16) . . ? O2 Tb1 N1 158.50(15) 3_675 . ? O9 Tb1 N1 87.45(15) . . ? O8 Tb1 N1 85.55(15) . . ? O6 Tb1 N1 25.35(12) . . ? O5 Tb1 N1 25.64(12) . . ? N1 O6 Tb1 96.7(3) . . ? C1 O1 Tb1 153.6(4) . . ? C12 O9 Tb1 131.0(4) . . ? O7 N1 O6 121.7(5) . . ? O7 N1 O5 121.5(5) . . ? O6 N1 O5 116.8(4) . . ? O7 N1 Tb1 172.5(4) . . ? O6 N1 Tb1 58.0(2) . . ? O5 N1 Tb1 59.4(2) . . ? C11 O8 Tb1 136.0(5) . . ? N1 O5 Tb1 95.0(3) . . ? C7 O3 Tb1 138.3(4) . . ? C1 O2 Tb1 133.2(4) . 3_675 ? O1 C1 O2 124.5(5) . . ? O1 C1 C2 117.8(5) . . ? O2 C1 C2 117.6(4) . . ? C7 O4 Tb1 147.5(4) 3_675 . ? C8 C2 C1 111.6(6) . . ? C8 C2 C3 113.1(8) . . ? C1 C2 C3 112.3(4) . . ? C8 C2 C6 103.5(8) . . ? C1 C2 C6 115.0(5) . . ? C3 C2 C6 100.8(5) . . ? C8' C4 C7 115.3(8) . 2_645 ? C8' C4 C5 106.7(8) . . ? C7 C4 C5 113.5(5) 2_645 . ? C8' C4 C3 105.6(9) . . ? C7 C4 C3 112.3(4) 2_645 . ? C5 C4 C3 102.3(5) . . ? O3 C7 O4 125.6(5) . 3_675 ? O3 C7 C4 118.4(5) . 2_655 ? O4 C7 C4 116.1(5) 3_675 2_655 ? C10 C3 C2 113.8(6) . . ? C10 C3 C4 113.2(6) . . ? C2 C3 C4 102.1(4) . . ? C10 C3 C9 109.3(7) . . ? C2 C3 C9 109.5(6) . . ? C4 C3 C9 108.7(6) . . ? C2 C6 C5 105.8(6) . . ? C4 C5 C6 105.6(6) . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 1.542 _refine_diff_density_min -0.981 _refine_diff_density_rms 0.128 data_ic15274 _database_code_depnum_ccdc_archive 'CCDC 893152' #TrackingRef 'web_deposit_cif_file_6_Chen-IYang_1343022745.ic15274.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H22 Dy N O9' _chemical_formula_weight 486.81 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' Dy Dy -0.1892 4.4098 '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)/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 10.2267(8) _cell_length_b 13.2034(11) _cell_length_c 12.8125(11) _cell_angle_alpha 90.00 _cell_angle_beta 106.3912(16) _cell_angle_gamma 90.00 _cell_volume 1659.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3859 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 23.12 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.948 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 956 _exptl_absorpt_coefficient_mu 4.546 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5299 _exptl_absorpt_correction_T_max 0.5686 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'BRUKER SMART APEXCCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14688 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0460 _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 2.26 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3803 _reflns_number_gt 3013 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0236P)^2^+8.2924P] 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 3803 _refine_ls_number_parameters 199 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.0916 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.008 _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 Dy Dy 0.34559(2) 1.00370(2) 0.57743(2) 0.01790(9) Uani 1 1 d . . . O1 O 0.3846(6) 0.8609(4) 0.4916(4) 0.0440(13) Uani 1 1 d . . . O2 O 0.5497(5) 0.8428(4) 0.4117(4) 0.0378(12) Uani 1 1 d . . . O3 O 0.0593(5) 0.5376(4) 0.1775(5) 0.0550(17) Uani 1 1 d . . . O4 O 0.2270(7) 0.5434(5) 0.1004(4) 0.0571(17) Uani 1 1 d . . . O5 O 0.2911(5) 0.8601(4) 0.6840(4) 0.0349(11) Uani 1 1 d . . . O6 O 0.1247(5) 0.9093(4) 0.5484(4) 0.0312(11) Uani 1 1 d . . . O7 O 0.1071(6) 0.7692(5) 0.6328(5) 0.0592(18) Uani 1 1 d . . . O8 O 0.1575(4) 1.1198(4) 0.5629(4) 0.0333(12) Uani 1 1 d . . . H8 H 0.0817 1.1045 0.5204 0.050 Uiso 1 1 d R . . O9 O 0.3554(6) 1.0668(4) 0.7587(4) 0.0440(14) Uani 1 1 d . . . H9 H 0.3493 1.1290 0.7699 0.066 Uiso 1 1 d R . . N1 N 0.1728(6) 0.8442(4) 0.6224(5) 0.0307(13) Uani 1 1 d . . . C2 C 0.4077(6) 0.7005(5) 0.4136(5) 0.0257(14) Uani 1 1 d D . . H2 H 0.3941 0.6671 0.4798 0.031 Uiso 0.648(8) 1 calc PR A 1 C5 C 0.2796(6) 0.5769(5) 0.2896(5) 0.0236(13) Uani 1 1 d D . . H5' H 0.2566 0.5481 0.3545 0.028 Uiso 0.352(8) 1 calc PR A 2 C6 C 0.4495(6) 0.8105(4) 0.4408(5) 0.0221(13) Uani 1 1 d . A . C7 C 0.1815(7) 0.5504(4) 0.1804(5) 0.0278(15) Uani 1 1 d . A . C1 C 0.2750(11) 0.6902(8) 0.3194(9) 0.025(2) Uiso 0.648(8) 1 d P A 1 C3 C 0.5109(19) 0.6374(16) 0.3724(19) 0.063(4) Uiso 0.648(8) 1 d PD A 1 H3A H 0.5841 0.6109 0.4344 0.075 Uiso 0.648(8) 1 calc PR A 1 H3B H 0.5526 0.6795 0.3264 0.075 Uiso 0.648(8) 1 calc PR A 1 C4 C 0.4276(14) 0.5481(15) 0.3044(18) 0.058(4) Uiso 0.648(8) 1 d PD A 1 H4A H 0.4469 0.5419 0.2332 0.069 Uiso 0.648(8) 1 calc PR A 1 H4B H 0.4498 0.4832 0.3440 0.069 Uiso 0.648(8) 1 calc PR A 1 C8 C 0.2825(12) 0.7549(9) 0.2251(10) 0.033(2) Uiso 0.648(8) 1 d P A 1 H8A H 0.2793 0.8265 0.2444 0.050 Uiso 0.648(8) 1 calc PR A 1 H8B H 0.2051 0.7394 0.1619 0.050 Uiso 0.648(8) 1 calc PR A 1 H8C H 0.3678 0.7411 0.2072 0.050 Uiso 0.648(8) 1 calc PR A 1 C9 C 0.1479(13) 0.7200(10) 0.3516(11) 0.044(3) Uiso 0.648(8) 1 d P A 1 H9A H 0.1516 0.7923 0.3693 0.067 Uiso 0.648(8) 1 calc PR A 1 H9B H 0.1434 0.6806 0.4154 0.067 Uiso 0.648(8) 1 calc PR A 1 H9C H 0.0668 0.7062 0.2910 0.067 Uiso 0.648(8) 1 calc PR A 1 C10 C 0.2496(18) 0.5231(13) 0.3833(14) 0.073(4) Uiso 0.648(8) 1 d P A 1 H10A H 0.2311 0.4515 0.3648 0.110 Uiso 0.648(8) 1 calc PR A 1 H10B H 0.1698 0.5539 0.3985 0.110 Uiso 0.648(8) 1 calc PR A 1 H10C H 0.3284 0.5287 0.4477 0.110 Uiso 0.648(8) 1 calc PR A 1 C1' C 0.3173(18) 0.6944(14) 0.2969(15) 0.025(2) Uiso 0.352(8) 1 d PD A 2 C3' C 0.510(3) 0.627(3) 0.389(4) 0.063(4) Uiso 0.352(8) 1 d PD A 2 H3'A H 0.5483 0.5824 0.4525 0.075 Uiso 0.352(8) 1 calc PR A 2 H3'B H 0.5856 0.6649 0.3728 0.075 Uiso 0.352(8) 1 calc PR A 2 C4' C 0.430(2) 0.565(3) 0.289(3) 0.058(4) Uiso 0.352(8) 1 d PD A 2 H4'A H 0.4437 0.5926 0.2216 0.069 Uiso 0.352(8) 1 calc PR A 2 H4'B H 0.4576 0.4932 0.2969 0.069 Uiso 0.352(8) 1 calc PR A 2 C8' C 0.334(2) 0.7488(16) 0.2013(16) 0.033(2) Uiso 0.352(8) 1 d PD A 2 H8'A H 0.3536 0.8203 0.2198 0.050 Uiso 0.352(8) 1 calc PR A 2 H8'B H 0.2492 0.7437 0.1417 0.050 Uiso 0.352(8) 1 calc PR A 2 H8'C H 0.4088 0.7188 0.1785 0.050 Uiso 0.352(8) 1 calc PR A 2 C9' C 0.185(2) 0.7518(17) 0.291(2) 0.044(3) Uiso 0.352(8) 1 d PD A 2 H9'A H 0.2027 0.8248 0.2941 0.067 Uiso 0.352(8) 1 calc PR A 2 H9'B H 0.1508 0.7317 0.3519 0.067 Uiso 0.352(8) 1 calc PR A 2 H9'C H 0.1166 0.7354 0.2221 0.067 Uiso 0.352(8) 1 calc PR A 2 C10' C 0.388(3) 0.645(2) 0.513(3) 0.073(4) Uiso 0.352(8) 1 d P A 2 H10D H 0.3222 0.6817 0.5414 0.110 Uiso 0.352(8) 1 calc PR A 2 H10E H 0.4752 0.6401 0.5693 0.110 Uiso 0.352(8) 1 calc PR A 2 H10F H 0.3531 0.5762 0.4915 0.110 Uiso 0.352(8) 1 calc PR A 2 C11 C 0.1560(9) 1.2255(7) 0.5845(8) 0.059(3) Uani 1 1 d . . . H11A H 0.1690 1.2362 0.6625 0.088 Uiso 1 1 calc R . . H11B H 0.0682 1.2542 0.5434 0.088 Uiso 1 1 calc R . . H11C H 0.2296 1.2589 0.5625 0.088 Uiso 1 1 calc R . . C12 C 0.3728(14) 1.0247(9) 0.8585(9) 0.086(3) Uani 1 1 d U . . H12A H 0.2840 1.0177 0.8728 0.129 Uiso 1 1 calc R . . H12B H 0.4318 1.0683 0.9140 0.129 Uiso 1 1 calc R . . H12C H 0.4149 0.9578 0.8605 0.129 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 Dy 0.01549(13) 0.01886(14) 0.01890(14) -0.00032(12) 0.00415(9) 0.00005(12) O1 0.059(4) 0.035(3) 0.038(3) -0.007(2) 0.014(3) 0.014(3) O2 0.024(2) 0.033(3) 0.052(3) 0.009(2) 0.003(2) -0.006(2) O3 0.027(3) 0.037(3) 0.086(5) -0.006(3) -0.008(3) -0.003(2) O4 0.101(5) 0.048(3) 0.024(3) -0.011(2) 0.021(3) -0.026(3) O5 0.034(3) 0.040(3) 0.027(3) 0.009(2) 0.003(2) -0.010(2) O6 0.024(2) 0.034(3) 0.035(3) 0.011(2) 0.007(2) 0.000(2) O7 0.066(4) 0.048(4) 0.057(4) 0.020(3) 0.005(3) -0.027(3) O8 0.017(2) 0.037(3) 0.043(3) -0.014(2) 0.003(2) 0.003(2) O9 0.075(4) 0.037(3) 0.021(3) 0.001(2) 0.015(3) 0.008(3) N1 0.035(3) 0.033(3) 0.027(3) 0.002(3) 0.015(3) -0.006(3) C2 0.030(3) 0.024(3) 0.022(3) -0.003(3) 0.006(3) -0.003(3) C5 0.028(3) 0.023(3) 0.018(3) -0.002(2) 0.002(3) -0.005(3) C6 0.022(3) 0.017(3) 0.019(3) 0.002(2) -0.006(3) 0.003(2) C7 0.036(4) 0.013(3) 0.026(4) 0.000(2) -0.005(3) -0.007(3) C11 0.044(5) 0.048(5) 0.078(7) -0.029(5) 0.005(5) 0.012(4) C12 0.132(8) 0.071(6) 0.053(5) -0.006(5) 0.024(6) -0.002(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 Dy O4 2.250(5) 2 ? Dy O3 2.267(5) 4_676 ? Dy O1 2.274(5) . ? Dy O2 2.278(5) 3_676 ? Dy O8 2.425(4) . ? Dy O9 2.442(5) . ? Dy O5 2.489(5) . ? Dy O6 2.514(5) . ? O1 C6 1.246(8) . ? O2 C6 1.259(8) . ? O2 Dy 2.278(5) 3_676 ? O3 C7 1.251(9) . ? O3 Dy 2.267(5) 4_575 ? O4 C7 1.243(9) . ? O4 Dy 2.250(5) 2_545 ? O5 N1 1.262(7) . ? O6 N1 1.271(7) . ? O7 N1 1.225(7) . ? O8 C11 1.424(9) . ? O9 C12 1.359(11) . ? C2 C10' 1.53(3) . ? C2 C3' 1.518(18) . ? C2 C1' 1.522(19) . ? C2 C6 1.526(8) . ? C2 C3 1.549(14) . ? C2 C1 1.547(12) . ? C5 C10 1.498(17) . ? C5 C7 1.515(8) . ? C5 C4 1.520(14) . ? C5 C4' 1.542(18) . ? C5 C1 1.548(12) . ? C5 C1' 1.596(19) . ? C1 C8 1.499(15) . ? C1 C9 1.523(16) . ? C3 C4 1.567(16) . ? C1' C8' 1.470(17) . ? C1' C9' 1.533(17) . ? C3' C4' 1.548(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Dy O3 128.2(3) 2 4_676 ? O4 Dy O1 75.9(2) 2 . ? O3 Dy O1 78.5(2) 4_676 . ? O4 Dy O2 82.5(2) 2 3_676 ? O3 Dy O2 79.50(19) 4_676 3_676 ? O1 Dy O2 128.6(2) . 3_676 ? O4 Dy O8 75.4(2) 2 . ? O3 Dy O8 144.4(2) 4_676 . ? O1 Dy O8 136.93(18) . . ? O2 Dy O8 77.96(16) 3_676 . ? O4 Dy O9 142.80(19) 2 . ? O3 Dy O9 76.7(2) 4_676 . ? O1 Dy O9 140.97(18) . . ? O2 Dy O9 75.30(19) 3_676 . ? O8 Dy O9 71.11(18) . . ? O4 Dy O5 132.2(2) 2 . ? O3 Dy O5 80.57(19) 4_676 . ? O1 Dy O5 74.38(19) . . ? O2 Dy O5 144.90(18) 3_676 . ? O8 Dy O5 103.16(17) . . ? O9 Dy O5 72.16(17) . . ? O4 Dy O6 86.6(2) 2 . ? O3 Dy O6 130.34(18) 4_676 . ? O1 Dy O6 77.91(19) . . ? O2 Dy O6 146.86(16) 3_676 . ? O8 Dy O6 69.01(16) . . ? O9 Dy O6 95.95(18) . . ? O5 Dy O6 51.15(15) . . ? C6 O1 Dy 152.6(5) . . ? C6 O2 Dy 133.7(4) . 3_676 ? C7 O3 Dy 147.7(6) . 4_575 ? C7 O4 Dy 139.4(5) . 2_545 ? N1 O5 Dy 96.2(4) . . ? N1 O6 Dy 94.7(4) . . ? C11 O8 Dy 131.0(5) . . ? C12 O9 Dy 135.6(6) . . ? O7 N1 O5 121.7(6) . . ? O7 N1 O6 121.3(6) . . ? O5 N1 O6 117.1(5) . . ? C10' C2 C3' 97(2) . . ? C10' C2 C1' 127.1(15) . . ? C3' C2 C1' 91.7(17) . . ? C10' C2 C6 111.3(13) . . ? C3' C2 C6 119.1(17) . . ? C1' C2 C6 109.1(8) . . ? C10' C2 C3 106.7(16) . . ? C3' C2 C3 10(3) . . ? C1' C2 C3 85.4(11) . . ? C6 C2 C3 114.5(10) . . ? C10' C2 C1 108.2(13) . . ? C3' C2 C1 106.7(15) . . ? C1' C2 C1 22.0(7) . . ? C6 C2 C1 112.9(6) . . ? C3 C2 C1 102.6(10) . . ? C10 C5 C7 113.5(8) . . ? C10 C5 C4 101.8(11) . . ? C7 C5 C4 115.7(9) . . ? C10 C5 C4' 112.5(18) . . ? C7 C5 C4' 112.0(14) . . ? C4 C5 C4' 11(2) . . ? C10 C5 C1 103.5(9) . . ? C7 C5 C1 113.1(6) . . ? C4 C5 C1 108.0(9) . . ? C4' C5 C1 101.3(15) . . ? C10 C5 C1' 121.0(10) . . ? C7 C5 C1' 111.4(8) . . ? C4 C5 C1' 91.2(10) . . ? C4' C5 C1' 82.7(16) . . ? C1 C5 C1' 21.4(6) . . ? O1 C6 O2 124.9(6) . . ? O1 C6 C2 118.1(6) . . ? O2 C6 C2 117.0(6) . . ? O4 C7 O3 124.7(7) . . ? O4 C7 C5 118.3(6) . . ? O3 C7 C5 117.0(7) . . ? C8 C1 C9 108.2(9) . . ? C8 C1 C5 109.9(8) . . ? C9 C1 C5 113.8(9) . . ? C8 C1 C2 110.3(9) . . ? C9 C1 C2 113.2(9) . . ? C5 C1 C2 101.3(7) . . ? C2 C3 C4 106.2(13) . . ? C5 C4 C3 104.3(13) . . ? C8' C1' C2 127.8(16) . . ? C8' C1' C9' 91.3(16) . . ? C2 C1' C9' 107.9(15) . . ? C8' C1' C5 120.6(15) . . ? C2 C1' C5 100.3(10) . . ? C9' C1' C5 106.4(14) . . ? C2 C3' C4' 106(2) . . ? C5 C4' C3' 104(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.174 _refine_diff_density_min -0.788 _refine_diff_density_rms 0.145 data_a13499a _database_code_depnum_ccdc_archive 'CCDC 893153' #TrackingRef 'web_deposit_cif_file_7_Chen-IYang_1343022745.a13499a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H44 Ho2 N2 O18' _chemical_formula_sum 'C24 H44 Ho2 N2 O18' _chemical_formula_weight 978.47 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' Ho Ho -0.2175 4.6783 '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 10.2606(5) _cell_length_b 13.2388(7) _cell_length_c 12.8502(7) _cell_angle_alpha 90.00 _cell_angle_beta 106.6290(10) _cell_angle_gamma 90.00 _cell_volume 1672.54(15) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.943 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 4.774 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3284 _exptl_absorpt_correction_T_max 0.7013 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9370 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2928 _reflns_number_gt 2502 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0466P)^2^+8.4120P] 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 2928 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.1150 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.288 _refine_ls_restrained_S_all 1.288 _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 C1 C -0.0497(7) 0.3113(5) 0.9417(6) 0.0241(16) Uani 1 1 d . . . C2 C -0.0929(7) 0.2020(5) 0.9134(6) 0.0273(17) Uani 1 1 d . . . C3 C -0.113(2) 0.1480(14) 1.0082(17) 0.056(5) Uani 0.50 1 d P . . H3A H -0.0327 0.1565 1.0706 0.083 Uiso 0.50 1 calc PR . . H3B H -0.1277 0.0759 0.9911 0.083 Uiso 0.50 1 calc PR . . H3C H -0.1930 0.1756 1.0257 0.083 Uiso 0.50 1 calc PR . . C4 C 0.0131(11) 0.1359(8) 0.8787(10) 0.066(3) Uani 1 1 d . . . H4A H 0.0777 0.1046 0.9430 0.079 Uiso 1 1 calc R . . H4B H 0.0650 0.1773 0.8402 0.079 Uiso 1 1 calc R . . C5 C -0.2168(11) 0.1927(7) 0.8124(8) 0.054(3) Uani 1 1 d . . . C6 C -0.2069(15) 0.2555(8) 0.7198(9) 0.083(4) Uani 1 1 d . . . H6A H -0.2878 0.2450 0.6582 0.124 Uiso 1 1 calc R . . H6B H -0.1256 0.2362 0.6990 0.124 Uiso 1 1 calc R . . H6C H -0.2007 0.3268 0.7410 0.124 Uiso 1 1 calc R . . C7 C -0.3514(12) 0.2239(11) 0.8418(13) 0.089(5) Uani 1 1 d . . . H7A H -0.3599 0.1833 0.9033 0.134 Uiso 1 1 calc R . . H7B H -0.4305 0.2122 0.7789 0.134 Uiso 1 1 calc R . . H7C H -0.3468 0.2957 0.8615 0.134 Uiso 1 1 calc R . . C8 C 0.1805(8) 0.4486(6) 1.1791(6) 0.0278(17) Uani 1 1 d . . . C9 C 0.2783(7) 0.4218(6) 1.2896(6) 0.0262(16) Uani 1 1 d . . . C10 C 0.250(3) 0.468(2) 1.3840(17) 0.077(7) Uani 0.50 1 d P . . H10A H 0.3183 0.4446 1.4502 0.116 Uiso 0.50 1 calc PR . . H10B H 0.1595 0.4477 1.3867 0.116 Uiso 0.50 1 calc PR . . H10C H 0.2548 0.5413 1.3788 0.116 Uiso 0.50 1 calc PR . . C11 C -0.0723(11) 0.0521(9) 0.8007(10) 0.067(3) Uani 1 1 d . . . H11A H -0.0543 0.0540 0.7290 0.081 Uiso 1 1 calc R . . H11B H -0.0495 -0.0160 0.8326 0.081 Uiso 1 1 calc R . . C12 C 0.132(3) 0.4751(11) 0.6427(11) 0.138(9) Uani 1 1 d . . . H12A H 0.1306 0.4210 0.5902 0.207 Uiso 1 1 calc R . . H12B H 0.2107 0.5190 0.6480 0.207 Uiso 1 1 calc R . . H12C H 0.0483 0.5148 0.6186 0.207 Uiso 1 1 calc R . . C13 C 0.3422(11) 0.2763(9) 0.9139(12) 0.080(4) Uani 1 1 d . . . H13A H 0.4362 0.2524 0.9289 0.121 Uiso 1 1 calc R . . H13B H 0.2936 0.2639 0.8374 0.121 Uiso 1 1 calc R . . H13C H 0.2969 0.2400 0.9602 0.121 Uiso 1 1 calc R . . N1 N 0.3262(7) 0.6550(5) 0.8789(6) 0.0362(16) Uani 1 1 d . . . O1 O 0.0485(5) 0.3446(4) 0.9111(5) 0.0419(15) Uani 1 1 d . . . O2 O -0.1161(7) 0.3618(5) 0.9897(5) 0.0470(16) Uani 1 1 d . . . O3 O 0.0584(6) 0.4610(5) 1.1763(6) 0.0537(18) Uani 1 1 d . . . O4 O 0.2277(7) 0.4554(5) 1.1000(5) 0.0530(18) Uani 1 1 d . . . O5 O 0.3740(5) 0.5900(4) 0.9530(5) 0.0383(14) Uani 1 1 d . . . O6 O 0.2075(6) 0.6404(5) 0.8175(5) 0.0409(14) Uani 1 1 d . . . O7 O 0.3932(8) 0.7292(6) 0.8676(6) 0.064(2) Uani 1 1 d . . . O8 O 0.1421(7) 0.4341(5) 0.7414(5) 0.0480(16) Uani 1 1 d . . . H8 H 0.1451 0.3624 0.7396 0.058 Uiso 1 1 calc R . . O9 O 0.3421(5) 0.3814(4) 0.9357(5) 0.0394(14) Uani 1 1 d . . . H9 H 0.4297 0.4115 0.9593 0.047 Uiso 1 1 calc R . . Ho1 Ho 0.15391(3) 0.49689(2) 0.92257(2) 0.01975(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.027(4) 0.021(4) 0.015(4) -0.002(3) -0.008(3) 0.000(3) C2 0.030(4) 0.023(4) 0.023(4) -0.001(3) -0.002(3) -0.004(3) C3 0.092(16) 0.030(10) 0.055(13) 0.016(9) 0.039(12) 0.000(10) C4 0.051(6) 0.055(7) 0.086(9) -0.005(6) 0.012(6) 0.004(5) C5 0.066(6) 0.035(5) 0.039(6) -0.007(4) -0.020(5) 0.002(5) C6 0.122(10) 0.032(6) 0.052(7) 0.008(5) -0.042(7) -0.011(6) C7 0.051(7) 0.091(10) 0.122(12) -0.045(9) 0.019(7) 0.016(7) C8 0.034(4) 0.021(4) 0.022(4) -0.001(3) -0.002(3) 0.005(3) C9 0.031(4) 0.029(4) 0.014(4) 0.009(3) -0.001(3) 0.004(3) C10 0.084(18) 0.12(2) 0.028(11) -0.019(13) 0.010(11) 0.000(16) C11 0.050(6) 0.071(8) 0.073(8) -0.012(7) 0.006(6) 0.015(6) C12 0.31(3) 0.071(9) 0.043(8) -0.010(7) 0.073(13) -0.015(13) C13 0.048(6) 0.063(7) 0.110(11) -0.047(7) -0.010(6) 0.021(5) N1 0.042(4) 0.038(4) 0.031(4) 0.007(3) 0.014(3) -0.006(3) O1 0.029(3) 0.036(3) 0.056(4) 0.008(3) 0.004(3) -0.007(2) O2 0.066(4) 0.039(3) 0.036(4) -0.010(3) 0.014(3) 0.015(3) O3 0.025(3) 0.043(4) 0.079(5) 0.011(4) -0.008(3) 0.006(3) O4 0.085(5) 0.048(4) 0.026(3) 0.010(3) 0.017(3) 0.020(4) O5 0.029(3) 0.041(3) 0.044(4) 0.004(3) 0.010(3) -0.004(2) O6 0.040(3) 0.047(4) 0.030(3) 0.013(3) 0.001(3) -0.011(3) O7 0.070(5) 0.062(5) 0.056(5) 0.017(4) 0.009(4) -0.035(4) O8 0.079(5) 0.043(4) 0.024(3) -0.003(3) 0.017(3) 0.005(3) O9 0.022(3) 0.042(3) 0.052(4) -0.019(3) 0.007(3) 0.004(2) Ho1 0.0171(2) 0.0221(2) 0.0194(2) -0.00034(14) 0.00410(14) -0.00036(12) _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 1.238(9) . ? C1 O1 1.261(9) . ? C1 C2 1.527(10) . ? C2 C3 1.478(18) . ? C2 C5 1.540(11) . ? C2 C4 1.557(13) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C11 1.581(15) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.478(16) . ? C5 C9 1.541(11) 4_565 ? C5 C7 1.588(15) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 O4 1.247(9) . ? C8 O3 1.254(10) . ? C8 C9 1.528(10) . ? C9 C10 1.46(2) . ? C9 C11 1.538(12) 4_666 ? C9 C5 1.541(12) 4_666 ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C9 1.538(12) 4_565 ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O8 1.356(14) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 O9 1.420(12) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? N1 O7 1.231(9) . ? N1 O6 1.262(9) . ? N1 O5 1.273(9) . ? N1 Ho1 2.897(7) . ? O1 Ho1 2.273(5) . ? O2 Ho1 2.274(6) 3_567 ? O3 Ho1 2.255(6) 3_567 ? O4 Ho1 2.255(6) . ? O5 Ho1 2.504(5) . ? O6 Ho1 2.483(5) . ? O8 Ho1 2.442(6) . ? O8 H8 0.9500 . ? O9 Ho1 2.430(5) . ? O9 H9 0.9500 . ? Ho1 O3 2.255(6) 3_567 ? Ho1 O2 2.274(6) 3_567 ? 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 124.7(7) . . ? O2 C1 C2 117.9(7) . . ? O1 C1 C2 117.4(7) . . ? C3 C2 C1 111.2(10) . . ? C3 C2 C5 112.2(11) . . ? C1 C2 C5 112.9(6) . . ? C3 C2 C4 103.9(11) . . ? C1 C2 C4 115.0(7) . . ? C5 C2 C4 100.9(7) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 C11 105.7(8) . . ? C2 C4 H4A 110.6 . . ? C11 C4 H4A 110.6 . . ? C2 C4 H4B 110.6 . . ? C11 C4 H4B 110.6 . . ? H4A C4 H4B 108.7 . . ? C6 C5 C2 113.8(9) . . ? C6 C5 C9 114.0(9) . 4_565 ? C2 C5 C9 102.3(7) . 4_565 ? C6 C5 C7 108.0(10) . . ? C2 C5 C7 110.0(9) . . ? C9 C5 C7 108.5(9) 4_565 . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O4 C8 O3 125.8(8) . . ? O4 C8 C9 118.0(7) . . ? O3 C8 C9 116.2(7) . . ? C10 C9 C8 116.4(12) . . ? C10 C9 C11 104.9(13) . 4_666 ? C8 C9 C11 113.9(7) . 4_666 ? C10 C9 C5 104.8(13) . 4_666 ? C8 C9 C5 112.5(7) . 4_666 ? C11 C9 C5 103.1(8) 4_666 4_666 ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 C4 104.9(8) 4_565 . ? C9 C11 H11A 110.8 4_565 . ? C4 C11 H11A 110.8 . . ? C9 C11 H11B 110.8 4_565 . ? C4 C11 H11B 110.8 . . ? H11A C11 H11B 108.8 . . ? O8 C12 H12A 109.5 . . ? O8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O9 C13 H13A 109.5 . . ? O9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O7 N1 O6 121.3(7) . . ? O7 N1 O5 121.2(7) . . ? O6 N1 O5 117.4(6) . . ? O7 N1 Ho1 172.6(6) . . ? O6 N1 Ho1 58.5(4) . . ? O5 N1 Ho1 59.5(4) . . ? C1 O1 Ho1 134.2(5) . . ? C1 O2 Ho1 152.6(6) . 3_567 ? C8 O3 Ho1 147.6(6) . 3_567 ? C8 O4 Ho1 138.1(6) . . ? N1 O5 Ho1 94.5(4) . . ? N1 O6 Ho1 95.8(4) . . ? C12 O8 Ho1 136.5(7) . . ? C12 O8 H8 111.8 . . ? Ho1 O8 H8 111.8 . . ? C13 O9 Ho1 130.4(6) . . ? C13 O9 H9 114.8 . . ? Ho1 O9 H9 114.8 . . ? O3 Ho1 O4 128.3(3) 3_567 . ? O3 Ho1 O1 79.5(2) 3_567 . ? O4 Ho1 O1 82.3(2) . . ? O3 Ho1 O2 78.5(2) 3_567 3_567 ? O4 Ho1 O2 75.8(2) . 3_567 ? O1 Ho1 O2 128.0(2) . 3_567 ? O3 Ho1 O9 144.6(2) 3_567 . ? O4 Ho1 O9 75.3(2) . . ? O1 Ho1 O9 78.50(19) . . ? O2 Ho1 O9 136.7(2) 3_567 . ? O3 Ho1 O8 76.7(3) 3_567 . ? O4 Ho1 O8 142.4(2) . . ? O1 Ho1 O8 75.1(2) . . ? O2 Ho1 O8 141.6(2) 3_567 . ? O9 Ho1 O8 71.0(2) . . ? O3 Ho1 O6 80.4(2) 3_567 . ? O4 Ho1 O6 132.4(2) . . ? O1 Ho1 O6 145.0(2) . . ? O2 Ho1 O6 74.7(2) 3_567 . ? O9 Ho1 O6 102.9(2) . . ? O8 Ho1 O6 72.6(2) . . ? O3 Ho1 O5 130.5(2) 3_567 . ? O4 Ho1 O5 86.3(2) . . ? O1 Ho1 O5 147.0(2) . . ? O2 Ho1 O5 78.0(2) 3_567 . ? O9 Ho1 O5 68.6(2) . . ? O8 Ho1 O5 96.5(2) . . ? O6 Ho1 O5 51.50(19) . . ? O3 Ho1 N1 104.9(2) 3_567 . ? O4 Ho1 N1 109.0(2) . . ? O1 Ho1 N1 159.1(2) . . ? O2 Ho1 N1 72.6(2) 3_567 . ? O9 Ho1 N1 87.2(2) . . ? O8 Ho1 N1 85.9(2) . . ? O6 Ho1 N1 25.69(19) . . ? O5 Ho1 N1 25.98(19) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.036 _refine_diff_density_min -1.088 _refine_diff_density_rms 0.392 data_a13448 _database_code_depnum_ccdc_archive 'CCDC 893154' #TrackingRef 'web_deposit_cif_file_8_Chen-IYang_1343022745.a13448.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H44 Er2 N2 O18' _chemical_formula_sum 'C24 H44 Er2 N2 O18' _chemical_formula_weight 983.13 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' 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' Er Er -0.2586 4.9576 '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 10.2427(4) _cell_length_b 13.2007(4) _cell_length_c 12.8252(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.646(2) _cell_angle_gamma 90.00 _cell_volume 1661.43(10) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour 'pale pink' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.965 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 5.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2076 _exptl_absorpt_correction_T_max 0.4607 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9549 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2897 _reflns_number_gt 2576 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0141P)^2^+35.4312P] 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 2897 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0788 _refine_ls_wR_factor_gt 0.0765 _refine_ls_goodness_of_fit_ref 0.884 _refine_ls_restrained_S_all 0.884 _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 0.1802(7) 0.0517(5) 0.6780(5) 0.0233(15) Uani 1 1 d . . . C2 C 0.2791(7) 0.0785(5) 0.7889(5) 0.0253(16) Uani 1 1 d . . . C3 C 0.4283(10) 0.0531(9) 0.7968(10) 0.066(3) Uani 1 1 d . . . H3A H 0.4449 0.0580 0.7246 0.079 Uiso 1 1 calc R . . H3B H 0.4521 -0.0160 0.8261 0.079 Uiso 1 1 calc R . . C4 C 0.5142(11) 0.1367(9) 0.8785(11) 0.070(3) Uani 1 1 d . . . H4A H 0.5779 0.1040 0.9426 0.083 Uiso 1 1 calc R . . H4B H 0.5675 0.1789 0.8416 0.083 Uiso 1 1 calc R . . C5 C 0.4087(7) 0.2020(5) 0.9135(5) 0.0228(15) Uani 1 1 d . . . C6 C 0.387(3) 0.1477(14) 1.0063(17) 0.061(6) Uani 0.50 1 d P . . H6A H 0.3620 0.0773 0.9855 0.091 Uiso 0.50 1 calc PR . . H6B H 0.3139 0.1804 1.0290 0.091 Uiso 0.50 1 calc PR . . H6C H 0.4713 0.1489 1.0667 0.091 Uiso 0.50 1 calc PR . . C7 C 0.2854(10) 0.1935(7) 0.8108(7) 0.052(3) Uani 1 1 d . . . C8 C 0.2949(13) 0.2549(7) 0.7184(8) 0.072(4) Uani 1 1 d . . . H8A H 0.2981 0.3268 0.7381 0.107 Uiso 1 1 calc R . . H8B H 0.2150 0.2423 0.6561 0.107 Uiso 1 1 calc R . . H8C H 0.3778 0.2368 0.6991 0.107 Uiso 1 1 calc R . . C9 C 0.1490(11) 0.2267(10) 0.8413(12) 0.090(5) Uani 1 1 d . . . H9A H 0.1514 0.2997 0.8554 0.135 Uiso 1 1 calc R . . H9B H 0.1440 0.1900 0.9065 0.135 Uiso 1 1 calc R . . H9C H 0.0689 0.2104 0.7806 0.135 Uiso 1 1 calc R . . C10 C 0.4496(7) 0.3123(5) 0.9411(5) 0.0209(15) Uani 1 1 d . . . C11 C 0.3428(11) 0.2231(8) 0.4133(10) 0.069(4) Uani 1 1 d . . . H11A H 0.4371 0.2460 0.4267 0.103 Uiso 1 1 calc R . . H11B H 0.2999 0.2601 0.4610 0.103 Uiso 1 1 calc R . . H11C H 0.2922 0.2359 0.3372 0.103 Uiso 1 1 calc R . . C12 C 0.133(2) 0.0252(10) 0.1438(9) 0.119(7) Uani 1 1 d . . . H12A H 0.1276 0.0796 0.0908 0.179 Uiso 1 1 calc R . . H12B H 0.0517 -0.0176 0.1202 0.179 Uiso 1 1 calc R . . H12C H 0.2144 -0.0159 0.1492 0.179 Uiso 1 1 calc R . . C13 C 0.248(2) 0.030(2) 0.8829(13) 0.073(7) Uani 0.50 1 d P . . H13A H 0.3166 0.0505 0.9502 0.109 Uiso 0.50 1 calc PR . . H13B H 0.2504 -0.0438 0.8752 0.109 Uiso 0.50 1 calc PR . . H13C H 0.1577 0.0510 0.8858 0.109 Uiso 0.50 1 calc PR . . N1 N 0.3269(7) -0.1551(5) 0.3799(5) 0.0327(15) Uani 1 1 d . . . O1 O 0.3737(5) -0.0895(4) 0.4547(4) 0.0338(13) Uani 1 1 d . . . O2 O 0.2080(6) -0.1389(4) 0.3180(4) 0.0368(13) Uani 1 1 d . . . O3 O 0.3931(7) -0.2290(5) 0.3679(6) 0.063(2) Uani 1 1 d . . . O4 O 0.2262(7) 0.0437(5) 0.5990(4) 0.0482(16) Uani 1 1 d . . . O5 O 0.0588(5) 0.0395(4) 0.6754(5) 0.0470(16) Uani 1 1 d . . . O6 O 0.5489(5) 0.3460(4) 0.9122(5) 0.0390(14) Uani 1 1 d . . . O7 O 0.3845(6) 0.3617(4) 0.9910(5) 0.0419(14) Uani 1 1 d . . . O8 O 0.3414(5) 0.1178(4) 0.4352(4) 0.0346(13) Uani 1 1 d . . . H8 H 0.4290 0.0873 0.4589 0.042 Uiso 1 1 calc R . . O9 O 0.1405(6) 0.0655(4) 0.2415(4) 0.0411(14) Uani 1 1 d . . . H9 H 0.1407 0.1375 0.2393 0.049 Uiso 1 1 calc R . . Er1 Er 0.15356(3) 0.00282(2) 0.42232(2) 0.01514(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.030(4) 0.016(3) 0.019(4) 0.001(3) -0.001(3) -0.004(3) C2 0.030(4) 0.025(4) 0.015(3) -0.005(3) -0.002(3) 0.000(3) C3 0.045(6) 0.072(8) 0.073(7) -0.003(6) 0.005(5) 0.012(5) C4 0.050(6) 0.058(7) 0.096(9) -0.007(6) 0.015(6) 0.007(5) C5 0.026(4) 0.022(4) 0.018(3) -0.002(3) 0.003(3) -0.003(3) C6 0.104(18) 0.034(10) 0.061(13) 0.018(9) 0.051(13) 0.004(11) C7 0.065(6) 0.028(5) 0.039(5) -0.005(4) -0.025(5) -0.002(4) C8 0.102(9) 0.036(5) 0.043(6) 0.010(4) -0.034(6) -0.017(6) C9 0.047(6) 0.088(10) 0.130(12) -0.053(9) 0.018(7) 0.010(6) C10 0.022(3) 0.021(4) 0.012(3) -0.001(3) -0.009(3) 0.000(3) C11 0.047(6) 0.053(6) 0.091(8) 0.040(6) -0.006(6) -0.014(5) C12 0.27(2) 0.064(8) 0.039(6) 0.008(6) 0.066(10) 0.014(11) C13 0.076(15) 0.13(2) 0.014(8) 0.027(11) 0.011(9) 0.000(14) N1 0.034(4) 0.036(4) 0.030(4) -0.007(3) 0.013(3) 0.009(3) O1 0.025(3) 0.038(3) 0.039(3) -0.008(3) 0.010(2) 0.002(2) O2 0.037(3) 0.045(3) 0.026(3) -0.012(2) 0.005(2) 0.011(3) O3 0.067(5) 0.056(4) 0.058(4) -0.019(3) 0.005(4) 0.036(4) O4 0.080(5) 0.047(4) 0.020(3) -0.012(3) 0.019(3) -0.018(3) O5 0.020(3) 0.036(3) 0.072(4) -0.011(3) -0.007(3) -0.007(2) O6 0.025(3) 0.036(3) 0.054(4) 0.009(3) 0.008(3) -0.009(2) O7 0.061(4) 0.032(3) 0.035(3) -0.009(3) 0.017(3) 0.014(3) O8 0.019(2) 0.039(3) 0.045(3) 0.016(3) 0.007(2) -0.006(2) O9 0.070(4) 0.037(3) 0.021(3) 0.002(2) 0.022(3) -0.003(3) Er1 0.01274(15) 0.01842(17) 0.01509(15) 0.00048(12) 0.00534(10) 0.00025(12) _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 O5 1.245(9) . ? C1 O4 1.238(9) . ? C1 C2 1.532(9) . ? C2 C13 1.477(19) . ? C2 C3 1.539(12) . ? C2 C7 1.542(11) . ? C3 C4 1.600(15) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.547(13) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.459(18) . ? C5 C10 1.528(9) . ? C5 C7 1.545(10) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.462(14) . ? C7 C9 1.615(15) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 O7 1.234(9) . ? C10 O6 1.259(9) . ? C11 O8 1.419(11) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O9 1.343(12) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? N1 O3 1.223(8) . ? N1 O2 1.267(8) . ? N1 O1 1.279(8) . ? N1 Er1 2.890(6) . ? O1 Er1 2.492(5) . ? O2 Er1 2.455(5) . ? O4 Er1 2.239(5) . ? O5 Er1 2.248(5) 3_556 ? O6 Er1 2.252(5) 4_666 ? O7 Er1 2.260(5) 2_556 ? O8 Er1 2.419(5) . ? O8 H8 0.9500 . ? O9 Er1 2.430(5) . ? O9 H9 0.9500 . ? Er1 O5 2.248(5) 3_556 ? Er1 O6 2.252(5) 4_565 ? Er1 O7 2.260(5) 2_546 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 C1 O4 125.3(7) . . ? O5 C1 C2 116.4(7) . . ? O4 C1 C2 118.3(7) . . ? C13 C2 C1 114.8(11) . . ? C13 C2 C3 107.0(11) . . ? C1 C2 C3 113.0(7) . . ? C13 C2 C7 106.6(12) . . ? C1 C2 C7 112.3(6) . . ? C3 C2 C7 102.3(8) . . ? C2 C3 C4 104.0(8) . . ? C2 C3 H3A 110.9 . . ? C4 C3 H3A 110.9 . . ? C2 C3 H3B 110.9 . . ? C4 C3 H3B 110.9 . . ? H3A C3 H3B 109.0 . . ? C5 C4 C3 106.0(8) . . ? C5 C4 H4A 110.5 . . ? C3 C4 H4A 110.5 . . ? C5 C4 H4B 110.5 . . ? C3 C4 H4B 110.5 . . ? H4A C4 H4B 108.7 . . ? C6 C5 C10 112.0(10) . . ? C6 C5 C4 104.1(11) . . ? C10 C5 C4 115.5(7) . . ? C6 C5 C7 112.5(12) . . ? C10 C5 C7 111.7(6) . . ? C4 C5 C7 100.4(7) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C2 114.0(8) . . ? C8 C7 C5 115.0(8) . . ? C2 C7 C5 102.0(6) . . ? C8 C7 C9 108.0(10) . . ? C2 C7 C9 108.4(9) . . ? C5 C7 C9 109.0(8) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O7 C10 O6 124.6(7) . . ? O7 C10 C5 118.1(7) . . ? O6 C10 C5 117.4(6) . . ? O8 C11 H11A 109.5 . . ? O8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O9 C12 H12A 109.5 . . ? O9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C2 C13 H13A 109.5 . . ? C2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O3 N1 O2 121.6(7) . . ? O3 N1 O1 122.2(7) . . ? O2 N1 O1 116.2(6) . . ? O3 N1 Er1 172.8(6) . . ? O2 N1 Er1 57.6(3) . . ? O1 N1 Er1 59.3(3) . . ? N1 O1 Er1 94.5(4) . . ? N1 O2 Er1 96.6(4) . . ? C1 O4 Er1 139.0(6) . . ? C1 O5 Er1 147.9(6) . 3_556 ? C10 O6 Er1 135.1(5) . 4_666 ? C10 O7 Er1 152.3(6) . 2_556 ? C11 O8 Er1 130.8(5) . . ? C11 O8 H8 114.6 . . ? Er1 O8 H8 114.6 . . ? C12 O9 Er1 136.7(7) . . ? C12 O9 H9 111.6 . . ? Er1 O9 H9 111.6 . . ? O4 Er1 O5 127.7(3) . 3_556 ? O4 Er1 O6 81.9(2) . 4_565 ? O5 Er1 O6 79.6(2) 3_556 4_565 ? O4 Er1 O7 75.8(2) . 2_546 ? O5 Er1 O7 78.1(2) 3_556 2_546 ? O6 Er1 O7 127.8(2) 4_565 2_546 ? O4 Er1 O8 75.7(2) . . ? O5 Er1 O8 144.9(2) 3_556 . ? O6 Er1 O8 78.70(19) 4_565 . ? O7 Er1 O8 136.9(2) 2_546 . ? O4 Er1 O9 142.7(2) . . ? O5 Er1 O9 76.8(2) 3_556 . ? O6 Er1 O9 75.4(2) 4_565 . ? O7 Er1 O9 141.3(2) 2_546 . ? O8 Er1 O9 71.14(19) . . ? O4 Er1 O2 132.3(2) . . ? O5 Er1 O2 80.9(2) 3_556 . ? O6 Er1 O2 145.4(2) 4_565 . ? O7 Er1 O2 74.8(2) 2_546 . ? O8 Er1 O2 102.4(2) . . ? O9 Er1 O2 72.46(19) . . ? O4 Er1 O1 85.8(2) . . ? O5 Er1 O1 131.0(2) 3_556 . ? O6 Er1 O1 146.79(19) 4_565 . ? O7 Er1 O1 77.9(2) 2_546 . ? O8 Er1 O1 68.38(18) . . ? O9 Er1 O1 97.2(2) . . ? O2 Er1 O1 51.83(17) . . ? O4 Er1 N1 108.7(2) . . ? O5 Er1 N1 105.3(2) 3_556 . ? O6 Er1 N1 159.5(2) 4_565 . ? O7 Er1 N1 72.5(2) 2_546 . ? O8 Er1 N1 86.90(19) . . ? O9 Er1 N1 86.26(19) . . ? O2 Er1 N1 25.82(17) . . ? O1 Er1 N1 26.19(17) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.906 _refine_diff_density_min -1.753 _refine_diff_density_rms 0.134 data_i14000 _database_code_depnum_ccdc_archive 'CCDC 907298' #TrackingRef 'web_deposit_cif_file_0_Chen-IYang_1351001845.i14000.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H15 O6 Tb' _chemical_formula_weight 402.15 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' Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.2558(17) _cell_length_b 10.820(2) _cell_length_c 14.719(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1314.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 2.031 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 5.394 _exptl_absorpt_correction_type multi_scan _exptl_absorpt_correction_T_min 0.7996 _exptl_absorpt_correction_T_max 0.9703 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41498 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 30.55 _reflns_number_total 4019 _reflns_number_gt 3814 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0217P)^2^+5.7838P] 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 SHELXL _refine_ls_extinction_coef 0.00040(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.001(18) _refine_ls_number_reflns 4019 _refine_ls_number_parameters 171 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0270 _refine_ls_R_factor_gt 0.0246 _refine_ls_wR_factor_ref 0.0610 _refine_ls_wR_factor_gt 0.0597 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 C1 C 0.3256(5) 0.2448(4) 0.3236(3) 0.0146(7) Uani 1 1 d . . . C2 C 0.3247(5) 0.2341(4) 0.2212(3) 0.0147(8) Uani 1 1 d . . . H2 H 0.2783 0.3109 0.1975 0.018 Uiso 1 1 calc R . . O3 O 0.4082(4) 0.0513(3) 0.5498(2) 0.0187(6) Uani 1 1 d . . . O1 O 0.4478(4) 0.2087(3) 0.3666(2) 0.0212(6) Uani 1 1 d . . . O2 O 0.7017(4) 0.2104(3) 0.6384(2) 0.0210(6) Uani 1 1 d . . . C9 C 0.2311(9) 0.0128(6) 0.2490(4) 0.0284(15) Uani 1 1 d . . . H9A H 0.3324 -0.0275 0.2368 0.043 Uiso 1 1 calc R . . H9B H 0.1436 -0.0432 0.2367 0.043 Uiso 1 1 calc R . . H9C H 0.2275 0.0375 0.3116 0.043 Uiso 1 1 calc R . . O5 O 0.3571(4) 0.3166(3) 0.5595(2) 0.0154(6) Uani 1 1 d . . . O4 O 0.6494(4) 0.4019(3) 0.4755(2) 0.0220(7) Uani 1 1 d . . . Tb1 Tb 0.578635(17) 0.201429(13) 0.501333(16) 0.01037(5) Uani 1 1 d . . . C4 C 0.7086(5) 0.5979(4) 0.4086(3) 0.0137(7) Uani 1 1 d . . . C7 C 0.7593(5) 0.4737(4) 0.4458(3) 0.0150(7) Uani 1 1 d . . . C8 C 0.7560(9) 0.6923(5) 0.4785(4) 0.0380(13) Uani 1 1 d . . . H8A H 0.7123 0.6691 0.5365 0.057 Uiso 1 1 calc R . . H8B H 0.7141 0.7716 0.4612 0.057 Uiso 1 1 calc R . . H8C H 0.8719 0.6964 0.4824 0.057 Uiso 1 1 calc R . . C11 C 0.3383(6) 0.4309(4) 0.5760(3) 0.0195(9) Uani 1 1 d . . . C6 C 0.4940(8) 0.2198(7) 0.1781(4) 0.0419(16) Uani 1 1 d . . . H6A H 0.5757 0.2050 0.2242 0.050 Uiso 1 1 calc R . . H6B H 0.5233 0.2929 0.1437 0.050 Uiso 1 1 calc R . . C3 C 0.2149(7) 0.1274(5) 0.1881(4) 0.0285(11) Uani 1 1 d . . . C5 C 0.5255(7) 0.6043(6) 0.3860(4) 0.0313(11) Uani 1 1 d . . . H5A H 0.4620 0.6147 0.4410 0.038 Uiso 1 1 calc R . . H5B H 0.4904 0.5296 0.3555 0.038 Uiso 1 1 calc R . . O6 O 0.2068(4) 0.4841(3) 0.5604(3) 0.0268(8) Uani 1 1 d . . . C10 C 0.0388(8) 0.1698(9) 0.1853(6) 0.053(2) Uani 1 1 d . . . H10A H -0.0298 0.1007 0.1716 0.079 Uiso 1 1 calc R . . H10B H 0.0262 0.2320 0.1393 0.079 Uiso 1 1 calc R . . H10C H 0.0092 0.2036 0.2433 0.079 Uiso 1 1 calc R . . H11 H 0.419(7) 0.475(5) 0.606(4) 0.016(13) 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 C1 0.0158(19) 0.0180(18) 0.0098(16) -0.0019(14) -0.0026(14) 0.0003(15) C2 0.0171(19) 0.0189(19) 0.0082(16) -0.0042(14) -0.0010(13) 0.0018(15) O3 0.0135(14) 0.0167(14) 0.0259(16) 0.0058(12) -0.0004(13) -0.0026(12) O1 0.0193(15) 0.0284(17) 0.0161(13) -0.0014(13) -0.0052(12) 0.0033(14) O2 0.0195(15) 0.0304(17) 0.0130(13) -0.0015(13) -0.0034(11) -0.0036(14) C9 0.038(4) 0.023(3) 0.0243(19) 0.0113(18) -0.002(2) -0.014(3) O5 0.0098(12) 0.0182(15) 0.0182(13) -0.0024(12) -0.0007(10) -0.0004(11) O4 0.0163(13) 0.0149(13) 0.035(2) 0.0077(12) 0.0071(12) 0.0002(12) Tb1 0.00696(7) 0.01168(7) 0.01246(7) 0.00124(12) -0.00081(11) -0.00055(5) C4 0.0117(16) 0.0124(16) 0.0168(18) 0.0031(15) 0.0011(14) 0.0013(14) C7 0.0164(19) 0.0128(17) 0.0159(17) 0.0026(13) -0.0012(15) 0.0033(15) C8 0.051(3) 0.030(2) 0.033(3) -0.001(2) -0.009(2) 0.004(3) C11 0.0148(19) 0.018(2) 0.025(2) -0.0046(17) -0.0032(17) -0.0016(16) C6 0.036(3) 0.063(4) 0.027(3) -0.016(3) 0.004(2) -0.017(3) C3 0.025(2) 0.032(3) 0.028(2) -0.004(2) 0.001(2) -0.002(2) C5 0.024(2) 0.040(3) 0.031(3) 0.006(2) 0.005(2) 0.005(2) O6 0.0169(16) 0.0161(15) 0.047(2) -0.0051(15) -0.0061(15) 0.0013(13) C10 0.028(3) 0.076(6) 0.055(4) -0.021(4) -0.007(3) 0.014(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 1.254(5) . ? C1 O2 1.263(5) 4_456 ? C1 C2 1.512(6) . ? C2 C6 1.543(8) . ? C2 C3 1.546(7) . ? O3 C7 1.261(5) 4_456 ? O3 Tb1 2.264(3) . ? O1 Tb1 2.259(3) . ? O2 C1 1.263(5) 4_556 ? O2 Tb1 2.261(3) . ? C9 C3 1.536(8) . ? O5 C11 1.269(5) . ? O5 Tb1 2.373(3) . ? O5 Tb1 2.475(3) 4_456 ? O4 C7 1.272(5) . ? O4 Tb1 2.278(3) . ? Tb1 O6 2.445(3) 4_556 ? Tb1 O5 2.475(3) 4_556 ? Tb1 C11 2.818(5) 4_556 ? C4 C8 1.501(7) . ? C4 C7 1.510(6) . ? C4 C5 1.550(7) . ? C4 C3 1.590(7) 3_655 ? C7 O3 1.261(5) 4_556 ? C11 O6 1.250(6) . ? C11 Tb1 2.818(5) 4_456 ? C6 C5 1.574(9) 3_645 ? C3 C10 1.525(8) . ? C3 C4 1.590(7) 3_645 ? C5 C6 1.574(9) 3_655 ? O6 Tb1 2.445(3) 4_456 ? 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 123.2(4) . 4_456 ? O1 C1 C2 119.0(4) . . ? O2 C1 C2 117.8(4) 4_456 . ? C1 C2 C6 114.4(4) . . ? C1 C2 C3 112.0(4) . . ? C6 C2 C3 109.1(4) . . ? C7 O3 Tb1 140.9(3) 4_456 . ? C1 O1 Tb1 147.0(3) . . ? C1 O2 Tb1 140.9(3) 4_556 . ? C11 O5 Tb1 132.5(3) . . ? C11 O5 Tb1 91.9(3) . 4_456 ? Tb1 O5 Tb1 122.94(13) . 4_456 ? C7 O4 Tb1 145.3(3) . . ? O1 Tb1 O2 175.17(14) . . ? O1 Tb1 O3 90.27(13) . . ? O2 Tb1 O3 91.64(12) . . ? O1 Tb1 O4 86.71(13) . . ? O2 Tb1 O4 89.60(13) . . ? O3 Tb1 O4 153.49(12) . . ? O1 Tb1 O5 85.98(11) . . ? O2 Tb1 O5 90.10(12) . . ? O3 Tb1 O5 77.53(12) . . ? O4 Tb1 O5 75.99(11) . . ? O1 Tb1 O6 84.82(13) . 4_556 ? O2 Tb1 O6 99.92(14) . 4_556 ? O3 Tb1 O6 78.28(12) . 4_556 ? O4 Tb1 O6 127.51(12) . 4_556 ? O5 Tb1 O6 154.03(11) . 4_556 ? O1 Tb1 O5 97.42(11) . 4_556 ? O2 Tb1 O5 84.77(11) . 4_556 ? O3 Tb1 O5 129.40(11) . 4_556 ? O4 Tb1 O5 77.08(11) . 4_556 ? O5 Tb1 O5 152.61(5) . 4_556 ? O6 Tb1 O5 53.04(11) 4_556 4_556 ? O1 Tb1 C11 91.53(13) . 4_556 ? O2 Tb1 C11 92.33(14) . 4_556 ? O3 Tb1 C11 103.63(13) . 4_556 ? O4 Tb1 C11 102.77(13) . 4_556 ? O5 Tb1 C11 177.27(13) . 4_556 ? O6 Tb1 C11 26.28(12) 4_556 4_556 ? O5 Tb1 C11 26.76(12) 4_556 4_556 ? C8 C4 C7 106.5(4) . . ? C8 C4 C5 111.8(4) . . ? C7 C4 C5 112.8(4) . . ? C8 C4 C3 111.9(4) . 3_655 ? C7 C4 C3 113.2(4) . 3_655 ? C5 C4 C3 100.8(4) . 3_655 ? O3 C7 O4 123.1(4) 4_556 . ? O3 C7 C4 118.7(4) 4_556 . ? O4 C7 C4 118.1(4) . . ? O6 C11 O5 121.3(4) . . ? O6 C11 Tb1 60.0(2) . 4_456 ? O5 C11 Tb1 61.4(2) . 4_456 ? C2 C6 C5 103.5(4) . 3_645 ? C10 C3 C9 110.0(6) . . ? C10 C3 C2 110.0(5) . . ? C9 C3 C2 111.5(5) . . ? C10 C3 C4 114.5(5) . 3_645 ? C9 C3 C4 109.0(5) . 3_645 ? C2 C3 C4 101.5(4) . 3_645 ? C4 C5 C6 105.3(5) . 3_655 ? C11 O6 Tb1 93.8(3) . 4_456 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.55 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.936 _refine_diff_density_min -0.866 _refine_diff_density_rms 0.146 data_i13902 _database_code_depnum_ccdc_archive 'CCDC 907299' #TrackingRef 'web_deposit_cif_file_1_Chen-IYang_1351001845.i13902.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H15 Er O6' _chemical_formula_sum 'C11 H15 Er O6' _chemical_formula_weight 410.49 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' Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.1149(16) _cell_length_b 10.823(2) _cell_length_c 14.712(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1292.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.02 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_max 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.110 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 6.511 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.739 _exptl_absorpt_correction_T_max 0.878 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10876 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 27.09 _reflns_number_total 2788 _reflns_number_gt 2583 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0455P)^2^+14.3683P] 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 CONST _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 0.99(3) _refine_ls_number_reflns 2788 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0960 _refine_ls_wR_factor_gt 0.0939 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.080 _refine_ls_shift/su_mean 0.005 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 C10 C 0.2310(19) 0.5132(11) 0.7503(7) 0.029(3) Uani 1 1 d . . . H10A H 0.1376 0.4601 0.7589 0.035 Uiso 1 1 calc R . . H10B H 0.3300 0.4693 0.7656 0.035 Uiso 1 1 calc R . . H10C H 0.2358 0.5391 0.6879 0.035 Uiso 1 1 calc R . . C1 C 0.3244(11) 0.7443(8) 0.6751(6) 0.0185(18) Uani 1 1 d . . . C2 C 0.3260(11) 0.7326(8) 0.7781(6) 0.0180(18) Uani 1 1 d . . . H2 H 0.2723 0.8078 0.8006 0.022 Uiso 1 1 calc R . . C5 C 0.2588(12) 0.5295(8) 0.4440(6) 0.0184(18) Uani 1 1 d . . . C11 C 0.3366(11) 0.9305(9) 0.4265(6) 0.0208(19) Uani 1 1 d . . . C4 C 0.2077(11) 0.4026(8) 0.4071(6) 0.0196(18) Uani 1 1 d . . . C7 C 0.490(2) 0.732(2) 0.8206(9) 0.102(9) Uani 1 1 d . . . H7A H 0.5079 0.8049 0.8577 0.122 Uiso 1 1 calc R . . H7B H 0.5772 0.7261 0.7755 0.122 Uiso 1 1 calc R . . C6 C 0.0210(15) 0.3947(13) 0.3834(8) 0.043(3) Uani 1 1 d . . . H6A H -0.0146 0.4667 0.3494 0.052 Uiso 1 1 calc R . . H6B H -0.0456 0.3872 0.4379 0.052 Uiso 1 1 calc R . . C9 C 0.046(3) 0.681(3) 0.8152(13) 0.169(16) Uani 1 1 d . . . H9A H 0.0064 0.6969 0.7548 0.203 Uiso 1 1 calc R . . H9B H 0.0508 0.7569 0.8486 0.203 Uiso 1 1 calc R . . H9C H -0.0280 0.6247 0.8452 0.203 Uiso 1 1 calc R . . C3 C 0.2146(15) 0.6245(12) 0.8104(7) 0.040(3) Uani 1 1 d . . . C8 C 0.2572(19) 0.3106(11) 0.4769(8) 0.052(3) Uani 1 1 d . . . H8A H 0.3752 0.3089 0.4817 0.063 Uiso 1 1 calc R . . H8B H 0.2179 0.2303 0.4596 0.063 Uiso 1 1 calc R . . H8C H 0.2105 0.3331 0.5345 0.063 Uiso 1 1 calc R . . Er1 Er 0.07655(3) 0.79670(3) 0.50159(3) 0.01231(11) Uani 1 1 d . . . O2 O -0.0503(8) 0.7915(6) 0.3677(4) 0.0240(14) Uani 1 1 d . . . O5 O -0.1444(7) 0.6845(6) 0.5588(4) 0.0190(13) Uani 1 1 d . . . O4 O -0.0911(8) 0.9453(6) 0.5521(5) 0.0231(14) Uani 1 1 d . . . O1 O 0.1987(8) 0.7891(7) 0.6371(4) 0.0251(14) Uani 1 1 d . . . O3 O 0.1460(7) 0.5990(6) 0.4734(4) 0.0242(16) Uani 1 1 d . . . O6 O 0.2023(8) 0.9823(6) 0.4439(5) 0.0305(16) Uani 1 1 d . . . H11 H 0.4174 0.9733 0.3974 0.050 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 C10 0.040(7) 0.021(5) 0.028(4) -0.007(4) 0.004(4) -0.009(5) C1 0.019(5) 0.022(5) 0.014(4) 0.000(3) -0.002(3) 0.001(4) C2 0.020(5) 0.019(4) 0.016(4) 0.003(3) -0.001(3) 0.001(4) C5 0.021(5) 0.017(4) 0.018(4) -0.003(3) -0.001(4) -0.002(4) C11 0.014(4) 0.027(5) 0.022(4) 0.006(4) 0.000(4) -0.005(4) C4 0.025(5) 0.015(4) 0.019(4) -0.006(3) 0.003(4) -0.003(4) C7 0.052(9) 0.24(3) 0.018(6) 0.007(10) 0.006(6) -0.066(14) C6 0.042(7) 0.049(7) 0.038(6) -0.002(6) 0.008(5) -0.004(6) C9 0.21(3) 0.25(3) 0.050(10) 0.044(15) 0.038(14) 0.21(3) C3 0.040(7) 0.049(7) 0.031(5) 0.016(5) -0.004(5) -0.002(6) C8 0.064(8) 0.044(7) 0.049(8) -0.003(5) -0.010(6) -0.003(6) Er1 0.00801(16) 0.01452(17) 0.01440(17) -0.0009(2) -0.0006(2) 0.00051(11) O2 0.023(3) 0.030(4) 0.019(3) 0.003(3) -0.003(3) -0.005(3) O5 0.012(3) 0.022(3) 0.023(3) 0.003(3) 0.001(2) 0.000(2) O4 0.015(3) 0.020(3) 0.034(4) -0.005(3) 0.004(3) 0.005(3) O1 0.024(3) 0.035(4) 0.016(3) 0.002(3) -0.001(3) 0.001(3) O3 0.017(3) 0.018(3) 0.038(4) -0.007(3) 0.007(3) -0.001(2) O6 0.020(3) 0.018(3) 0.053(4) 0.006(3) 0.001(3) 0.001(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 C10 C3 1.500(17) . ? C1 O2 1.259(11) 4_566 ? C1 O1 1.260(11) . ? C1 C2 1.520(12) . ? C2 C7 1.473(18) . ? C2 C3 1.553(14) . ? C5 O4 1.250(11) 4_566 ? C5 O3 1.262(11) . ? C5 C4 1.534(12) . ? C11 O6 1.251(11) . ? C11 O5 1.273(11) 4_566 ? C11 Er1 2.788(9) . ? C4 C8 1.485(15) . ? C4 C6 1.558(15) . ? C4 C3 1.583(13) 2_564 ? C7 C6 1.66(2) 2_565 ? C6 C7 1.66(2) 2_564 ? C9 C3 1.50(2) . ? C3 C4 1.583(13) 2_565 ? Er1 O2 2.223(6) . ? Er1 O1 2.228(6) . ? Er1 O4 2.234(6) . ? Er1 O3 2.251(6) . ? Er1 O5 2.323(6) . ? Er1 O6 2.407(7) . ? Er1 O5 2.441(6) 4_566 ? O2 C1 1.259(11) 4_466 ? O5 C11 1.273(11) 4_466 ? O5 Er1 2.441(6) 4_466 ? O4 C5 1.250(11) 4_466 ? 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 123.4(9) 4_566 . ? O2 C1 C2 117.8(8) 4_566 . ? O1 C1 C2 118.8(8) . . ? C7 C2 C1 115.5(8) . . ? C7 C2 C3 113.2(11) . . ? C1 C2 C3 111.2(8) . . ? O4 C5 O3 124.1(8) 4_566 . ? O4 C5 C4 118.4(8) 4_566 . ? O3 C5 C4 117.4(8) . . ? O6 C11 O5 120.5(8) . 4_566 ? O6 C11 Er1 59.5(5) . . ? O5 C11 Er1 61.1(4) 4_566 . ? C8 C4 C5 106.5(8) . . ? C8 C4 C6 112.4(10) . . ? C5 C4 C6 113.0(8) . . ? C8 C4 C3 112.9(9) . 2_564 ? C5 C4 C3 112.1(8) . 2_564 ? C6 C4 C3 100.1(8) . 2_564 ? C2 C7 C6 100.9(11) . 2_565 ? C4 C6 C7 103.0(10) . 2_564 ? C10 C3 C9 115.7(16) . . ? C10 C3 C2 111.9(10) . . ? C9 C3 C2 103.9(15) . . ? C10 C3 C4 110.2(9) . 2_565 ? C9 C3 C4 113.4(11) . 2_565 ? C2 C3 C4 100.5(8) . 2_565 ? O2 Er1 O1 176.3(3) . . ? O2 Er1 O4 91.8(2) . . ? O1 Er1 O4 90.0(2) . . ? O2 Er1 O3 85.9(2) . . ? O1 Er1 O3 91.1(2) . . ? O4 Er1 O3 153.9(2) . . ? O2 Er1 O5 87.1(2) . . ? O1 Er1 O5 90.0(2) . . ? O4 Er1 O5 77.6(2) . . ? O3 Er1 O5 76.3(2) . . ? O2 Er1 O6 84.5(3) . . ? O1 Er1 O6 99.1(3) . . ? O4 Er1 O6 77.0(2) . . ? O3 Er1 O6 128.5(2) . . ? O5 Er1 O6 153.0(2) . . ? O2 Er1 O5 96.3(2) . 4_566 ? O1 Er1 O5 85.2(2) . 4_566 ? O4 Er1 O5 128.8(2) . 4_566 ? O3 Er1 O5 77.3(2) . 4_566 ? O5 Er1 O5 153.04(10) . 4_566 ? O6 Er1 O5 53.8(2) . 4_566 ? O2 Er1 C11 90.7(3) . . ? O1 Er1 C11 92.1(3) . . ? O4 Er1 C11 102.6(3) . . ? O3 Er1 C11 103.4(3) . . ? O5 Er1 C11 177.8(2) . . ? O6 Er1 C11 26.6(3) . . ? O5 Er1 C11 27.2(2) 4_566 . ? C1 O2 Er1 145.7(6) 4_466 . ? C11 O5 Er1 131.8(6) 4_466 . ? C11 O5 Er1 91.8(5) 4_466 4_466 ? Er1 O5 Er1 122.7(3) . 4_466 ? C5 O4 Er1 140.0(6) 4_466 . ? C1 O1 Er1 140.4(6) . . ? C5 O3 Er1 144.3(6) . . ? C11 O6 Er1 93.9(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.09 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.762 _refine_diff_density_min -1.275 _refine_diff_density_rms 0.168 data_i13974 _database_code_depnum_ccdc_archive 'CCDC 907300' #TrackingRef 'web_deposit_cif_file_2_Chen-IYang_1351001845.i13974.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H15 Ho O6' _chemical_formula_weight 408.16 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' Ho Ho -0.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.1597(16) _cell_length_b 10.818(2) _cell_length_c 14.716(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1299.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 2.087 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 6.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8400 _exptl_absorpt_correction_T_max 0.9703 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6344 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 27.10 _reflns_number_total 2858 _reflns_number_gt 2623 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0243P)^2^+6.6725P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(2) _refine_ls_number_reflns 2858 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0337 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0720 _refine_ls_wR_factor_gt 0.0700 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.033 _refine_ls_shift/su_mean 0.002 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 Ho1 Ho 0.07677(3) 0.70291(2) 0.00160(3) 0.01235(8) Uani 1 1 d . . . O3 O 0.1467(5) 0.9016(4) -0.0263(3) 0.0232(13) Uani 1 1 d . . . O1 O -0.0514(6) 0.7095(5) -0.1327(3) 0.0230(11) Uani 1 1 d . . . O5 O 0.2029(6) 0.5175(5) -0.0573(4) 0.0286(13) Uani 1 1 d . . . O2 O 0.1996(6) 0.7104(5) 0.1372(3) 0.0246(11) Uani 1 1 d . . . O4 O -0.0915(6) 0.5540(4) 0.0513(4) 0.0228(11) Uani 1 1 d . . . O6 O 0.3555(5) 0.6841(4) -0.0592(3) 0.0178(10) Uani 1 1 d . . . C1 C 0.3247(8) 0.7547(6) 0.1756(5) 0.0177(14) Uani 1 1 d . . . C2 C 0.3244(8) 0.7654(6) 0.2780(5) 0.0163(14) Uani 1 1 d . . . H2 H 0.2730 0.6898 0.3010 0.020 Uiso 1 1 calc R . . C7 C 0.2583(8) 0.9713(6) -0.0552(5) 0.0181(14) Uani 1 1 d . . . C5 C 0.2080(8) 1.0973(6) -0.0923(5) 0.0175(14) Uani 1 1 d . . . C11 C 0.3362(8) 0.5694(7) -0.0744(6) 0.0236(17) Uani 1 1 d . . . C8 C 0.2601(14) 1.1918(8) -0.0239(7) 0.057(3) Uani 1 1 d . . . H8A H 0.2198 1.1689 0.0350 0.085 Uiso 1 1 calc R . . H8B H 0.2164 1.2711 -0.0405 0.085 Uiso 1 1 calc R . . H8C H 0.3776 1.1962 -0.0223 0.085 Uiso 1 1 calc R . . C3 C 0.4949(13) 0.7712(13) 0.3203(7) 0.068(4) Uani 1 1 d . . . H3A H 0.5796 0.7794 0.2745 0.082 Uiso 1 1 calc R . . H3B H 0.5172 0.6992 0.3576 0.082 Uiso 1 1 calc R . . C4 C 0.0225(12) 1.1033(10) -0.1182(7) 0.050(3) Uani 1 1 d . . . H4A H -0.0453 1.1085 -0.0642 0.060 Uiso 1 1 calc R . . H4B H -0.0095 1.0309 -0.1528 0.060 Uiso 1 1 calc R . . C10 C 0.2302(14) 0.9864(9) 0.2504(6) 0.030(2) Uani 1 1 d . . . H10A H 0.1528 1.0484 0.2688 0.045 Uiso 1 1 calc R . . H10B H 0.2092 0.9629 0.1886 0.045 Uiso 1 1 calc R . . H10C H 0.3393 1.0189 0.2553 0.045 Uiso 1 1 calc R . . C6 C 0.2137(12) 0.8757(9) 0.3106(7) 0.042(2) Uiso 1 1 d . . . C9 C 0.0353(15) 0.8297(12) 0.3150(9) 0.067(3) Uiso 1 1 d . . . H9A H -0.0355 0.8972 0.3312 0.100 Uiso 1 1 calc R . . H9B H 0.0264 0.7656 0.3598 0.100 Uiso 1 1 calc R . . H9C H 0.0036 0.7978 0.2567 0.100 Uiso 1 1 calc R . . H11 H 0.416(14) 0.524(11) -0.110(8) 0.080 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 Ho1 0.00853(11) 0.01428(13) 0.01425(13) 0.0009(2) -0.0006(2) -0.00051(9) O3 0.016(2) 0.020(2) 0.033(3) 0.007(2) 0.0054(19) 0.0013(19) O1 0.022(2) 0.028(3) 0.020(3) -0.001(2) -0.004(2) 0.003(2) O5 0.017(2) 0.016(3) 0.053(4) -0.005(2) 0.002(2) 0.001(2) O2 0.022(2) 0.034(3) 0.018(3) -0.001(2) -0.002(2) -0.001(2) O4 0.015(2) 0.021(3) 0.032(3) 0.002(2) -0.002(2) -0.002(2) O6 0.013(2) 0.019(3) 0.021(3) -0.003(2) 0.0023(19) -0.0019(19) C1 0.021(3) 0.019(3) 0.013(3) -0.002(3) 0.000(3) -0.001(3) C2 0.019(3) 0.017(3) 0.013(3) -0.004(3) 0.000(3) 0.000(3) C7 0.018(3) 0.016(3) 0.019(3) 0.003(3) 0.002(3) 0.001(3) C5 0.024(3) 0.012(3) 0.017(3) 0.003(3) 0.006(3) 0.002(3) C11 0.011(3) 0.028(4) 0.031(5) -0.007(3) 0.002(3) 0.004(3) C8 0.069(6) 0.036(5) 0.065(8) -0.004(5) -0.026(6) 0.010(5) C3 0.050(6) 0.129(12) 0.024(5) -0.014(6) -0.001(5) 0.039(7) C4 0.040(5) 0.055(6) 0.056(7) 0.023(6) 0.018(5) 0.012(5) C10 0.038(6) 0.023(5) 0.029(4) 0.007(3) -0.004(4) 0.010(4) _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 Ho1 O2 2.234(5) . ? Ho1 O1 2.237(5) . ? Ho1 O4 2.240(5) . ? Ho1 O3 2.262(5) . ? Ho1 O6 2.339(5) 4_465 ? Ho1 O5 2.416(5) . ? Ho1 O6 2.453(4) . ? Ho1 C11 2.796(7) . ? O3 C7 1.257(8) . ? O1 C1 1.253(8) 4_465 ? O5 C11 1.249(9) . ? O2 C1 1.262(8) . ? O4 C7 1.257(8) 4_465 ? O6 C11 1.271(9) . ? O6 Ho1 2.339(5) 4_565 ? C1 O1 1.253(8) 4_565 ? C1 C2 1.511(10) . ? C2 C3 1.526(12) . ? C2 C6 1.572(11) . ? C7 O4 1.257(8) 4_565 ? C7 C5 1.525(9) . ? C5 C8 1.496(11) . ? C5 C4 1.562(12) . ? C5 C6 1.593(11) 2_574 ? C3 C4 1.638(14) 2_575 ? C4 C3 1.638(14) 2_574 ? C10 C6 1.495(13) . ? C6 C9 1.540(15) . ? C6 C5 1.593(11) 2_575 ? 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 Ho1 O1 175.9(2) . . ? O2 Ho1 O4 90.52(19) . . ? O1 Ho1 O4 91.43(19) . . ? O2 Ho1 O3 90.85(19) . . ? O1 Ho1 O3 85.82(18) . . ? O4 Ho1 O3 153.85(17) . . ? O2 Ho1 O6 90.20(18) . 4_465 ? O1 Ho1 O6 86.71(17) . 4_465 ? O4 Ho1 O6 77.54(18) . 4_465 ? O3 Ho1 O6 76.34(16) . 4_465 ? O2 Ho1 O5 99.18(19) . . ? O1 Ho1 O5 84.76(19) . . ? O4 Ho1 O5 77.36(18) . . ? O3 Ho1 O5 128.07(18) . . ? O6 Ho1 O5 153.23(17) 4_465 . ? O2 Ho1 O6 85.01(17) . . ? O1 Ho1 O6 96.54(17) . . ? O4 Ho1 O6 128.91(17) . . ? O3 Ho1 O6 77.21(15) . . ? O6 Ho1 O6 153.04(8) 4_465 . ? O5 Ho1 O6 53.49(16) . . ? O2 Ho1 C11 92.1(2) . . ? O1 Ho1 C11 91.0(2) . . ? O4 Ho1 C11 102.9(2) . . ? O3 Ho1 C11 103.1(2) . . ? O6 Ho1 C11 177.7(2) 4_465 . ? O5 Ho1 C11 26.48(19) . . ? O6 Ho1 C11 27.02(19) . . ? C7 O3 Ho1 144.6(4) . . ? C1 O1 Ho1 146.3(5) 4_465 . ? C11 O5 Ho1 94.0(4) . . ? C1 O2 Ho1 141.0(5) . . ? C7 O4 Ho1 140.2(5) 4_465 . ? C11 O6 Ho1 132.1(5) . 4_565 ? C11 O6 Ho1 91.7(4) . . ? Ho1 O6 Ho1 122.7(2) 4_565 . ? O1 C1 O2 123.0(7) 4_565 . ? O1 C1 C2 118.7(6) 4_565 . ? O2 C1 C2 118.3(6) . . ? C1 C2 C3 114.1(6) . . ? C1 C2 C6 111.3(6) . . ? C3 C2 C6 111.6(7) . . ? O4 C7 O3 124.1(6) 4_565 . ? O4 C7 C5 118.2(6) 4_565 . ? O3 C7 C5 117.5(6) . . ? C8 C5 C7 107.1(6) . . ? C8 C5 C4 114.3(8) . . ? C7 C5 C4 112.7(6) . . ? C8 C5 C6 111.4(7) . 2_574 ? C7 C5 C6 112.2(6) . 2_574 ? C4 C5 C6 99.3(6) . 2_574 ? O5 C11 O6 120.8(7) . . ? O5 C11 Ho1 59.5(4) . . ? O6 C11 Ho1 61.3(4) . . ? C2 C3 C4 100.4(7) . 2_575 ? C5 C4 C3 104.6(8) . 2_574 ? C10 C6 C9 111.6(9) . . ? C10 C6 C2 112.1(8) . . ? C9 C6 C2 108.1(8) . . ? C10 C6 C5 110.4(7) . 2_575 ? C9 C6 C5 113.6(8) . 2_575 ? C2 C6 C5 100.5(6) . 2_575 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.555 _refine_diff_density_min -1.042 _refine_diff_density_rms 0.155 data_yci_2_1_full_0m _database_code_depnum_ccdc_archive 'CCDC 907301' #TrackingRef 'web_deposit_cif_file_3_Chen-IYang_1351001845.yci_2_1_full_0m.cif' _audit_creation_method SHELXL-97 _audit_creation_date 2012-09-26 _audit_update_record 2012-09-26 _chemical_formula_sum 'C11 H15 Dy O6' _chemical_formula_weight 405.730 _refine_ls_R_factor_all 0.040 _cell_length_a 8.1878(8) _cell_length_b 10.8856(11) _cell_length_c 14.7371(15) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 1313.5(2) _cell_formula_units_Z 4 _symmetry_int_tables_number 19 _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall P_2ac_2ab loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_radius_bond Dy ? 1.200 O ? 1.200 C ? 1.200 H ? 1.200 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_Wyckoff_symbol _atom_site_attached_hydrogens _atom_site_calc_flag _atom_site_thermal_displace_type _atom_site_u_iso_or_equiv Dy1 Dy 0.5755(0) 0.2966(0) -0.0014(0) 1.000 4 a ? d Uani 0.02186(8) O5 O 0.3551(5) 0.1829(4) -0.0591(3) 1.000 4 a ? d Uani 0.0313(11) O2 O 0.6989(6) 0.2872(5) -0.1377(3) 1.000 4 a ? d Uani 0.0406(12) O3 O 0.6469(6) 0.0994(4) 0.0285(3) 1.000 4 a ? d Uani 0.0403(14) O6 O 0.7032(6) 0.4826(5) 0.0561(5) 1.000 4 a ? d Uani 0.0516(15) C9 C 0.2355(17) 0.4864(10) 0.2505(7) 1.000 4 a ? d Uani 0.051(3) H9A H 0.2033 0.4663 0.1897 1.000 4 a ? calc Uiso 0.07600 H9B H 0.3479 0.5113 0.2510 1.000 4 a ? calc Uiso 0.07600 H9C H 0.1687 0.5524 0.2728 1.000 4 a ? calc Uiso 0.07600 O1 O 0.4467(6) 0.2906(5) 0.1326(3) 1.000 4 a ? d Uani 0.0400(12) O4 O 0.9074(6) 0.0554(5) 0.0517(4) 1.000 4 a ? d Uani 0.0381(12) C2 C 0.3237(8) 0.2694(6) 0.2773(4) 1.000 4 a ? d Uani 0.0292(15) H2 H 0.2698 0.1948 0.2992 1.000 4 a ? calc Uiso 0.03500 C1 C 0.3244(8) 0.2571(6) 0.1755(5) 1.000 4 a ? d Uani 0.0294(14) C6 C 0.7093(8) -0.0955(6) 0.0927(4) 1.000 4 a ? d Uani 0.0273(13) C7 C 0.7581(8) 0.0305(6) 0.0566(4) 1.000 4 a ? d Uani 0.0284(14) C10 C 0.045(2) 0.320(2) 0.318(1) 1.000 4 a ? d Uani 0.178(11) H10A H -0.0197 0.3682 0.3590 1.000 4 a ? calc Uiso 0.26700 H10B H 0.0537 0.2376 0.3405 1.000 4 a ? calc Uiso 0.26700 H10C H -0.0057 0.3192 0.2593 1.000 4 a ? calc Uiso 0.26700 C11 C 0.8360(9) 0.4307(7) 0.0731(6) 1.000 4 a ? d Uani 0.0412(19) C4 C 0.2142(11) 0.3757(9) 0.3104(6) 1.000 4 a ? d Uani 0.055(2) C3 C 0.4864(16) 0.267(2) 0.3185(7) 1.000 4 a ? d Uani 0.169(11) H3A H 0.5722 0.2704 0.2732 1.000 4 a ? calc Uiso 0.20200 H3B H 0.5017 0.1946 0.3563 1.000 4 a ? calc Uiso 0.20200 C5 C 0.5227(12) -0.1021(11) 0.1186(7) 1.000 4 a ? d Uani 0.069(3) H5A H 0.4545 -0.1079 0.0649 1.000 4 a ? calc Uiso 0.08300 H5B H 0.4898 -0.0311 0.1539 1.000 4 a ? calc Uiso 0.08300 C8 C 0.771(2) -0.1891(9) 0.0272(11) 1.000 4 a ? d Uani 0.141(8) H8A H 0.7380 -0.1670 -0.0332 1.000 4 a ? calc Uiso 0.21200 H8B H 0.7262 -0.2681 0.0423 1.000 4 a ? calc Uiso 0.21200 H8C H 0.8878 -0.1926 0.0303 1.000 4 a ? calc Uiso 0.21200 H11 H 0.9046 0.4842 0.0888 1.000 4 a ? d Uiso 0.04800 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Dy1 0.01642(11) 0.02492(13) 0.02424(12) 0.00115(10) 0.0014(2) 0.0018(3) O5 0.021(2) 0.033(3) 0.040(3) -0.004(2) 0.0017(19) -0.008(2) O2 0.037(3) 0.055(3) 0.030(2) 0.003(3) 0.005(2) -0.003(3) O3 0.034(2) 0.030(3) 0.057(4) -0.001(2) -0.011(2) 0.014(2) O6 0.033(3) 0.030(3) 0.091(4) 0.000(2) -0.008(3) -0.014(3) C9 0.079(6) 0.036(5) 0.036(3) 0.020(5) 0.005(4) 0.013(3) O1 0.040(3) 0.051(3) 0.029(2) -0.004(3) 0.011(2) -0.002(2) O4 0.028(3) 0.032(3) 0.055(3) -0.008(2) 0.002(2) 0.010(2) C2 0.035(4) 0.032(4) 0.020(3) 0.005(3) 0.002(2) -0.003(3) C1 0.032(3) 0.033(4) 0.023(3) -0.001(3) 0.001(3) -0.001(3) C6 0.025(3) 0.024(3) 0.032(3) 0.000(3) 0.003(3) 0.001(3) C7 0.030(3) 0.026(3) 0.029(3) 0.000(3) 0.000(3) 0.007(3) C10 0.150(15) 0.30(3) 0.088(10) -0.181(17) 0.011(10) -0.033(13) C11 0.031(4) 0.039(4) 0.054(5) -0.007(3) -0.006(3) -0.017(4) C4 0.059(5) 0.067(6) 0.039(4) 0.015(5) -0.009(4) -0.020(4) C3 0.089(9) 0.38(3) 0.032(5) 0.154(15) -0.002(5) -0.025(10) C5 0.054(5) 0.073(7) 0.081(7) -0.022(5) -0.017(5) 0.035(6) C8 0.184(14) 0.043(6) 0.197(19) -0.024(7) 0.141(14) -0.025(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Dy1 O1 . . 2.241(5) no Dy1 O4 . 3_455 2.245(5) no Dy1 O2 . . 2.250(5) no Dy1 O3 . . 2.268(5) no Dy1 O5 . . 2.348(5) no Dy1 O6 . . 2.432(5) no Dy1 O5 . 3 2.467(4) no Dy1 C11 . . 2.808(7) no O5 C11 . 3_455 1.263(9) no O5 Dy1 . 3_455 2.467(4) no O2 C1 . 3 1.264(8) no O3 C7 . . 1.250(8) no O6 C11 . . 1.250(9) no C9 C4 . . 1.503(14) no O1 C1 . . 1.239(8) no O4 C7 . . 1.254(8) no O4 Dy1 . 3 2.245(5) no C2 C3 . . 1.464(14) no C2 C1 . . 1.506(9) no C2 C4 . . 1.543(11) no C1 O2 . 3_455 1.264(8) no C6 C8 . . 1.491(12) no C6 C7 . . 1.525(9) no C6 C5 . . 1.576(11) no C6 C4 . 4_645 1.592(10) no C10 C4 . . 1.515(15) no C11 O5 . 3 1.263(9) no C4 C6 . 4_655 1.592(10) no C3 C5 . 4_655 1.70(2) no C5 C3 . 4_645 1.70(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 Dy1 O4 . . 3_455 91.3(2) no O1 Dy1 O2 . . . 175.5(2) no O4 Dy1 O2 3_455 . . 90.8(2) no O1 Dy1 O3 . . . 85.6(2) no O4 Dy1 O3 3_455 . . 154.37(18) no O2 Dy1 O3 . . . 90.9(2) no O1 Dy1 O5 . . . 86.68(18) no O4 Dy1 O5 3_455 . . 77.72(18) no O2 Dy1 O5 . . . 89.91(18) no O3 Dy1 O5 . . . 76.70(17) no O1 Dy1 O6 . . . 85.3(2) no O4 Dy1 O6 3_455 . . 77.35(19) no O2 Dy1 O6 . . . 99.0(2) no O3 Dy1 O6 . . . 127.54(19) no O5 Dy1 O6 . . . 153.60(17) no O1 Dy1 O5 . . 3 96.91(17) no O4 Dy1 O5 3_455 . 3 128.55(18) no O2 Dy1 O5 . . 3 84.85(17) no O3 Dy1 O5 . . 3 77.07(16) no O5 Dy1 O5 . . 3 153.15(8) no O6 Dy1 O5 . . 3 53.08(17) no O1 Dy1 C11 . . . 91.6(2) no O4 Dy1 C11 3_455 . . 102.8(2) no O2 Dy1 C11 . . . 91.8(2) no O3 Dy1 C11 . . . 102.7(2) no O5 Dy1 C11 . . . 178.2(2) no O6 Dy1 C11 . . . 26.4(2) no O5 Dy1 C11 3 . . 26.71(19) no C11 O5 Dy1 3_455 . . 132.1(5) no C11 O5 Dy1 3_455 . 3_455 91.9(4) no Dy1 O5 Dy1 . . 3_455 122.3(2) no C1 O2 Dy1 3 . . 140.9(5) no C7 O3 Dy1 . . . 145.1(4) no C11 O6 Dy1 . . . 93.8(4) no C1 O1 Dy1 . . . 147.0(5) no C7 O4 Dy1 . . 3 140.5(5) no C3 C2 C1 . . . 114.1(6) no C3 C2 C4 . . . 114.4(9) no C1 C2 C4 . . . 112.6(6) no O1 C1 O2 . . 3_455 123.0(7) no O1 C1 C2 . . . 119.0(6) no O2 C1 C2 3_455 . . 118.0(6) no C8 C6 C7 . . . 107.5(6) no C8 C6 C5 . . . 117.0(9) no C7 C6 C5 . . . 112.3(6) no C8 C6 C4 . . 4_645 108.3(9) no C7 C6 C4 . . 4_645 112.7(6) no C5 C6 C4 . . 4_645 98.9(6) no O3 C7 O4 . . . 124.1(6) no O3 C7 C6 . . . 117.6(6) no O4 C7 C6 . . . 118.1(6) no O6 C11 O5 . . 3 121.2(6) no O6 C11 Dy1 . . . 59.8(4) no O5 C11 Dy1 3 . . 61.4(3) no C9 C4 C10 . . . 118.0(12) no C9 C4 C2 . . . 110.4(8) no C10 C4 C2 . . . 104.7(11) no C9 C4 C6 . . 4_655 108.9(8) no C10 C4 C6 . . 4_655 111.8(9) no C2 C4 C6 . . 4_655 101.7(6) no C2 C3 C5 . . 4_655 99.7(8) no C6 C5 C3 . . 4_645 102.2(8) no