# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_1 #------------------------------------------------------------------------------ _Attachment Dy.cif _database_code_depnum_ccdc_archive 'CCDC 740834' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H15 Dy O6' _chemical_formula_sum 'C11 H15 Dy O6' _chemical_formula_weight 405.73 _chemical_absolute_configuration rm 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' Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.152(3) _cell_length_b 10.886(4) _cell_length_c 14.782(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1311.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3887 _cell_measurement_theta_min 3.1209 _cell_measurement_theta_max 27.4797 _exptl_crystal_description Prism _exptl_crystal_colour white _exptl_crystal_size_max 0.2500 _exptl_crystal_size_mid 0.1500 _exptl_crystal_size_min 0.1100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.054 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 5.712 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.6739 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 9823 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2994 _reflns_number_gt 2783 _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^)+(0.0416P)^2^+0.8646P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(2) _refine_ls_number_reflns 2994 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0754 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 Dy1 Dy 0.07406(2) 0.795484(19) -0.001836(19) 0.02013(9) Uani 1 1 d . . . O1 O 0.1447(6) 0.6000(4) 0.0280(4) 0.0469(14) Uani 1 1 d . . . O2 O 0.4064(5) 0.5570(4) 0.0540(4) 0.0400(12) Uani 1 1 d . . . O3 O 0.3037(6) 0.2144(5) 0.3623(3) 0.0423(12) Uani 1 1 d . . . O4 O 0.0545(6) 0.2914(5) 0.3690(3) 0.0433(12) Uani 1 1 d . . . O5 O 0.1979(6) 0.9814(5) 0.0555(4) 0.0556(15) Uani 1 1 d . . . O6 O 0.3541(5) 0.8190(4) 0.0581(3) 0.0315(10) Uani 1 1 d . . . C1 C 0.2082(8) 0.4064(5) 0.0945(4) 0.0285(13) Uani 1 1 d . . . C2 C 0.2895(10) 0.3804(8) 0.1909(5) 0.0510(19) Uani 1 1 d . . . C3 C 0.1777(7) 0.2690(5) 0.2232(4) 0.0259(13) Uani 1 1 d . . . H3A H 0.2274 0.1938 0.1992 0.031 Uiso 1 1 calc R . . C4 C 0.0055(12) 0.2787(10) 0.1819(7) 0.072(2) Uani 1 1 d . . . H4A H -0.0773 0.2908 0.2282 0.086 Uiso 1 1 calc R . . H4B H -0.0216 0.2063 0.1468 0.086 Uiso 1 1 calc R . . C5 C 0.0239(11) 0.3986(11) 0.1183(6) 0.072(2) Uani 1 1 d . . . H5A H -0.0417 0.3900 0.0639 0.086 Uiso 1 1 calc R . . H5B H -0.0112 0.4719 0.1503 0.086 Uiso 1 1 calc R . . C6 C 0.2586(8) 0.5308(5) 0.0575(4) 0.0285(13) Uani 1 1 d . . . C7 C 0.2601(15) 0.3125(7) 0.0236(6) 0.072(3) Uani 1 1 d . . . H7A H 0.2089 0.3318 -0.0331 0.108 Uiso 1 1 calc R . . H7B H 0.2271 0.2319 0.0426 0.108 Uiso 1 1 calc R . . H7C H 0.3772 0.3147 0.0166 0.108 Uiso 1 1 calc R . . C8 C 0.2719(14) 0.4904(10) 0.2509(6) 0.0618(17) Uani 1 1 d . . . H8A H 0.1591 0.5156 0.2524 0.093 Uiso 1 1 calc R . . H8B H 0.3381 0.5562 0.2278 0.093 Uiso 1 1 calc R . . H8C H 0.3073 0.4698 0.3110 0.093 Uiso 1 1 calc R . . C9 C 0.4679(12) 0.3381(9) 0.1883(6) 0.0618(17) Uani 1 1 d . . . H9A H 0.5364 0.4048 0.1691 0.093 Uiso 1 1 calc R . . H9B H 0.4787 0.2709 0.1467 0.093 Uiso 1 1 calc R . . H9C H 0.5008 0.3118 0.2476 0.093 Uiso 1 1 calc R . . C10 C 0.1784(7) 0.2577(5) 0.3257(5) 0.0308(14) Uani 1 1 d . . . C11 C 0.3304(9) 0.9321(6) 0.0736(5) 0.0398(16) Uani 1 1 d . . . H11A H 0.4141 0.9787 0.0990 0.048 Uiso 1 1 d 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 Dy1 0.01501(12) 0.02329(12) 0.02208(13) 0.00181(17) 0.00140(17) 0.00099(8) O1 0.039(2) 0.029(2) 0.072(4) 0.011(2) -0.013(2) -0.004(2) O2 0.026(2) 0.036(2) 0.059(3) 0.013(2) 0.005(2) -0.008(2) O3 0.041(3) 0.062(3) 0.024(2) 0.006(2) -0.011(2) 0.002(3) O4 0.045(3) 0.062(3) 0.023(2) 0.006(2) 0.012(2) 0.006(3) O5 0.037(3) 0.033(2) 0.097(4) -0.013(3) -0.003(3) 0.000(2) O6 0.020(2) 0.033(2) 0.041(3) -0.0088(19) 0.0009(19) 0.0002(18) C1 0.034(3) 0.024(3) 0.027(3) 0.004(2) -0.003(3) -0.005(3) C2 0.051(5) 0.056(4) 0.046(4) 0.016(4) -0.008(4) -0.012(4) C3 0.029(3) 0.029(3) 0.020(3) 0.006(2) 0.004(2) -0.002(3) C4 0.059(4) 0.103(5) 0.053(4) 0.029(4) -0.016(3) -0.031(4) C5 0.059(4) 0.103(5) 0.053(4) 0.029(4) -0.016(3) -0.031(4) C6 0.032(3) 0.027(3) 0.026(3) 0.005(2) -0.002(3) -0.001(3) C7 0.114(8) 0.049(5) 0.052(5) 0.000(4) 0.021(5) -0.004(5) C8 0.073(5) 0.064(4) 0.049(3) -0.001(3) -0.006(3) -0.011(3) C9 0.073(5) 0.064(4) 0.049(3) -0.001(3) -0.006(3) -0.011(3) C10 0.036(4) 0.032(3) 0.024(3) 0.001(2) -0.001(2) -0.003(3) C11 0.029(4) 0.040(4) 0.050(4) -0.014(3) -0.002(3) -0.006(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 Dy1 O4 2.226(5) 4 ? Dy1 O3 2.245(5) 2_564 ? Dy1 O2 2.245(4) 3_465 ? Dy1 O1 2.249(4) . ? Dy1 O6 2.337(4) 3_465 ? Dy1 O5 2.416(5) . ? Dy1 O6 2.462(4) . ? Dy1 C11 2.796(7) . ? O1 C6 1.272(7) . ? O2 C6 1.240(7) . ? O2 Dy1 2.245(4) 3_565 ? O3 C10 1.248(7) . ? O3 Dy1 2.245(5) 2_565 ? O4 C10 1.251(8) . ? O4 Dy1 2.226(5) 4_545 ? O5 C11 1.235(9) . ? O6 C11 1.267(8) . ? O6 Dy1 2.337(4) 3_565 ? C1 C6 1.516(8) . ? C1 C7 1.524(10) . ? C1 C5 1.545(11) . ? C1 C2 1.596(9) . ? C2 C8 1.497(12) . ? C2 C9 1.526(12) . ? C2 C3 1.590(9) . ? C3 C10 1.521(9) . ? C3 C4 1.534(11) . ? C3 H3A 0.9800 . ? C4 C5 1.616(12) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C11 H11A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Dy1 O3 175.7(2) 4 2_564 ? O4 Dy1 O2 91.75(19) 4 3_465 ? O3 Dy1 O2 89.86(19) 2_564 3_465 ? O4 Dy1 O1 85.9(2) 4 . ? O3 Dy1 O1 90.9(2) 2_564 . ? O2 Dy1 O1 154.20(18) 3_465 . ? O4 Dy1 O6 86.68(17) 4 3_465 ? O3 Dy1 O6 89.79(17) 2_564 3_465 ? O2 Dy1 O6 78.01(17) 3_465 3_465 ? O1 Dy1 O6 76.21(16) . 3_465 ? O4 Dy1 O5 84.5(2) 4 . ? O3 Dy1 O5 99.7(2) 2_564 . ? O2 Dy1 O5 77.02(19) 3_465 . ? O1 Dy1 O5 128.11(19) . . ? O6 Dy1 O5 153.19(16) 3_465 . ? O4 Dy1 O6 96.96(17) 4 . ? O3 Dy1 O6 85.16(17) 2_564 . ? O2 Dy1 O6 127.85(16) 3_465 . ? O1 Dy1 O6 77.89(15) . . ? O6 Dy1 O6 153.51(8) 3_465 . ? O5 Dy1 O6 53.07(16) . . ? O4 Dy1 C11 90.6(2) 4 . ? O3 Dy1 C11 92.9(2) 2_564 . ? O2 Dy1 C11 102.2(2) 3_465 . ? O1 Dy1 C11 103.51(19) . . ? O6 Dy1 C11 177.29(19) 3_465 . ? O5 Dy1 C11 26.13(19) . . ? O6 Dy1 C11 26.93(17) . . ? C6 O1 Dy1 144.5(4) . . ? C6 O2 Dy1 140.4(4) . 3_565 ? C10 O3 Dy1 140.3(5) . 2_565 ? C10 O4 Dy1 146.9(5) . 4_545 ? C11 O5 Dy1 94.4(4) . . ? C11 O6 Dy1 134.4(5) . 3_565 ? C11 O6 Dy1 91.4(4) . . ? Dy1 O6 Dy1 121.86(18) 3_565 . ? C6 C1 C7 106.0(5) . . ? C6 C1 C5 113.2(6) . . ? C7 C1 C5 113.0(7) . . ? C6 C1 C2 111.6(5) . . ? C7 C1 C2 112.3(6) . . ? C5 C1 C2 101.0(5) . . ? C8 C2 C9 110.3(8) . . ? C8 C2 C3 112.1(7) . . ? C9 C2 C3 108.9(7) . . ? C8 C2 C1 110.3(7) . . ? C9 C2 C1 115.3(7) . . ? C3 C2 C1 99.6(5) . . ? C10 C3 C4 113.9(6) . . ? C10 C3 C2 111.1(5) . . ? C4 C3 C2 110.6(6) . . ? C10 C3 H3A 107.0 . . ? C4 C3 H3A 107.0 . . ? C2 C3 H3A 107.0 . . ? C3 C4 C5 101.7(6) . . ? C3 C4 H4A 111.4 . . ? C5 C4 H4A 111.4 . . ? C3 C4 H4B 111.4 . . ? C5 C4 H4B 111.4 . . ? H4A C4 H4B 109.3 . . ? C1 C5 C4 105.5(7) . . ? C1 C5 H5A 110.6 . . ? C4 C5 H5A 110.6 . . ? C1 C5 H5B 110.6 . . ? C4 C5 H5B 110.6 . . ? H5A C5 H5B 108.8 . . ? O2 C6 O1 123.9(6) . . ? O2 C6 C1 118.9(6) . . ? O1 C6 C1 117.0(5) . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C9 H9A 109.5 . . ? C2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O3 C10 O4 123.4(7) . . ? O3 C10 C3 117.7(6) . . ? O4 C10 C3 118.9(5) . . ? O5 C11 O6 121.1(6) . . ? O5 C11 Dy1 59.5(4) . . ? O6 C11 Dy1 61.7(3) . . ? O5 C11 H11A 119.4 . . ? O6 C11 H11A 119.4 . . ? Dy1 C11 H11A 178.8 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.599 _refine_diff_density_min -0.779 _refine_diff_density_rms 0.137 ####################################################################### # # 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_a _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 _chemical_absolute_configuration rm 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' Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.1178(5) _cell_length_b 10.9087(7) _cell_length_c 14.7493(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1306.12(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3542 _cell_measurement_theta_min 2.3217 _cell_measurement_theta_max 27.4758 _exptl_crystal_description Block _exptl_crystal_colour pink _exptl_crystal_size_max 0.2370 _exptl_crystal_size_mid 0.1080 _exptl_crystal_size_min 0.0810 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.088 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 6.441 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.5584 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 9979 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2985 _reflns_number_gt 2775 _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. Due to somewhat flexibility of the D-cam and especially high thermal libration of its three terminal methyl groups, the restraints EADP,SIMU,DELU are applied for refinement. ; _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^)+(0.0369P)^2^+3.2277P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 2985 _refine_ls_number_parameters 152 _refine_ls_number_restraints 42 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0844 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.173 _refine_ls_restrained_S_all 1.172 _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 Er1 Er -0.42633(3) -0.79498(2) -0.49821(2) 0.02260(10) Uani 1 1 d . . . C1 C -0.2911(12) -0.4072(8) -0.5946(6) 0.0438(8) Uani 1 1 d U . . C2 C -0.2107(11) -0.3810(8) -0.6915(6) 0.0435(9) Uani 1 1 d U . . C3 C -0.3194(11) -0.2702(8) -0.7235(6) 0.0424(10) Uani 1 1 d U . . H3A H -0.2676 -0.1958 -0.6995 0.051 Uiso 1 1 calc R . . C4 C -0.4928(12) -0.2781(9) -0.6804(6) 0.0457(9) Uani 1 1 d . . . H4A H -0.5775 -0.2886 -0.7261 0.055 Uiso 1 1 calc R . . H4B H -0.5173 -0.2058 -0.6445 0.055 Uiso 1 1 calc R . . C5 C -0.4753(11) -0.3979(9) -0.6179(6) 0.0457(9) Uani 1 1 d U . . H5A H -0.5406 -0.3894 -0.5632 0.055 Uiso 1 1 calc R . . H5B H -0.5118 -0.4703 -0.6503 0.055 Uiso 1 1 calc R . . C6 C -0.2406(12) -0.5319(9) -0.5577(6) 0.0431(9) Uani 1 1 d U . . C7 C -0.2399(12) -0.3145(8) -0.5250(5) 0.0470(11) Uani 1 1 d U . . H7A H -0.2903 -0.3339 -0.4679 0.070 Uiso 1 1 calc R . . H7B H -0.2744 -0.2343 -0.5440 0.070 Uiso 1 1 calc R . . H7C H -0.1223 -0.3158 -0.5185 0.070 Uiso 1 1 calc R . . C8 C -0.2288(18) -0.4914(12) -0.7511(8) 0.063(2) Uani 1 1 d . . . H8A H -0.1814 -0.4747 -0.8094 0.095 Uiso 1 1 calc R . . H8B H -0.3435 -0.5106 -0.7581 0.095 Uiso 1 1 calc R . . H8C H -0.1731 -0.5598 -0.7239 0.095 Uiso 1 1 calc R . . C9 C -0.0292(15) -0.3401(11) -0.6897(8) 0.063(2) Uani 1 1 d . . . H9A H 0.0087 -0.3273 -0.7506 0.095 Uiso 1 1 calc R . . H9B H 0.0365 -0.4025 -0.6614 0.095 Uiso 1 1 calc R . . H9C H -0.0195 -0.2651 -0.6561 0.095 Uiso 1 1 calc R . . C10 C -0.3199(9) -0.2581(6) -0.8253(5) 0.0305(16) Uani 1 1 d . . . C11 C -0.1703(11) -0.9298(8) -0.5732(6) 0.0391(19) Uani 1 1 d . . . H11C H -0.0841 -0.9781 -0.5999 0.047 Uiso 1 1 d R . . O1 O -0.3545(7) -0.6005(5) -0.5284(4) 0.0432(16) Uani 1 1 d . . . O2 O -0.0934(7) -0.5578(5) -0.5532(4) 0.0410(14) Uani 1 1 d . . . O3 O -0.1959(7) -0.2152(6) -0.8628(4) 0.0422(14) Uani 1 1 d . . . O4 O -0.4467(7) -0.2914(6) -0.8691(4) 0.0423(14) Uani 1 1 d . . . O5 O -0.3032(8) -0.9810(6) -0.5550(5) 0.0547(18) Uani 1 1 d . . . O6 O -0.1471(6) -0.8180(5) -0.5577(4) 0.0315(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 Er1 0.01560(13) 0.02674(15) 0.02547(15) 0.0015(2) -0.0011(2) -0.00104(9) C1 0.047(2) 0.0477(19) 0.0367(18) 0.0064(15) 0.0023(15) 0.0077(17) C2 0.047(2) 0.047(2) 0.0368(18) 0.0068(16) 0.0018(16) 0.0076(18) C3 0.046(2) 0.046(2) 0.036(2) 0.0061(16) 0.0016(17) 0.0071(19) C4 0.048(2) 0.051(2) 0.0391(19) 0.0070(16) 0.0027(16) 0.0086(18) C5 0.048(2) 0.051(2) 0.0391(19) 0.0070(16) 0.0027(16) 0.0086(18) C6 0.046(2) 0.0471(19) 0.0357(19) 0.0063(16) 0.0029(17) 0.0072(18) C7 0.053(2) 0.049(2) 0.039(2) 0.0040(18) 0.0008(19) 0.008(2) C8 0.074(6) 0.062(4) 0.053(4) -0.004(3) -0.002(4) 0.012(4) C9 0.074(6) 0.062(4) 0.053(4) -0.004(3) -0.002(4) 0.012(4) C10 0.033(4) 0.033(4) 0.026(4) 0.001(3) 0.004(3) -0.002(3) C11 0.030(4) 0.039(4) 0.048(5) -0.009(4) 0.001(4) 0.007(4) O1 0.038(3) 0.024(2) 0.067(5) 0.012(2) 0.007(3) -0.002(2) O2 0.024(3) 0.038(3) 0.062(4) 0.015(3) -0.006(3) 0.003(2) O3 0.041(3) 0.063(4) 0.022(3) 0.003(3) 0.008(2) 0.002(3) O4 0.042(3) 0.060(4) 0.025(3) 0.001(3) -0.014(2) -0.008(3) O5 0.033(3) 0.033(3) 0.098(5) -0.008(3) 0.005(3) -0.002(3) O6 0.021(2) 0.034(3) 0.040(3) -0.009(2) 0.002(2) -0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Er1 O4 2.212(5) 4_443 ? Er1 O3 2.233(5) 2_445 ? Er1 O2 2.235(5) 3_434 ? Er1 O1 2.245(5) . ? Er1 O6 2.327(5) 3_434 ? Er1 O5 2.412(6) . ? Er1 O6 2.444(5) . ? Er1 C11 2.776(8) . ? C1 C7 1.501(12) . ? C1 C6 1.521(12) . ? C1 C5 1.537(13) . ? C1 C2 1.596(12) . ? C2 C8 1.499(15) . ? C2 C9 1.540(15) . ? C2 C3 1.569(12) . ? C3 C10 1.507(12) . ? C3 C4 1.547(13) . ? C3 H3A 0.9800 . ? C4 C5 1.605(12) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O2 1.230(10) . ? C6 O1 1.266(10) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 O3 1.241(9) . ? C10 O4 1.269(9) . ? C11 O5 1.244(10) . ? C11 O6 1.255(9) . ? C11 H11C 0.9602 . ? O2 Er1 2.235(5) 3_534 ? O3 Er1 2.233(5) 2_444 ? O4 Er1 2.212(5) 4_453 ? O6 Er1 2.327(5) 3_534 ? 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 Er1 O3 175.9(2) 4_443 2_445 ? O4 Er1 O2 91.7(2) 4_443 3_434 ? O3 Er1 O2 90.1(2) 2_445 3_434 ? O4 Er1 O1 85.9(2) 4_443 . ? O3 Er1 O1 90.9(2) 2_445 . ? O2 Er1 O1 154.7(2) 3_434 . ? O4 Er1 O6 86.9(2) 4_443 3_434 ? O3 Er1 O6 89.9(2) 2_445 3_434 ? O2 Er1 O6 78.0(2) 3_434 3_434 ? O1 Er1 O6 76.7(2) . 3_434 ? O4 Er1 O5 84.3(2) 4_443 . ? O3 Er1 O5 99.7(2) 2_445 . ? O2 Er1 O5 76.4(2) 3_434 . ? O1 Er1 O5 128.2(2) . . ? O6 Er1 O5 152.6(2) 3_434 . ? O4 Er1 O6 96.6(2) 4_443 . ? O3 Er1 O6 85.1(2) 2_445 . ? O2 Er1 O6 127.7(2) 3_434 . ? O1 Er1 O6 77.58(19) . . ? O6 Er1 O6 153.70(9) 3_434 . ? O5 Er1 O6 53.44(19) . . ? O4 Er1 C11 90.3(2) 4_443 . ? O3 Er1 C11 92.9(2) 2_445 . ? O2 Er1 C11 102.0(2) 3_434 . ? O1 Er1 C11 103.1(2) . . ? O6 Er1 C11 177.2(2) 3_434 . ? O5 Er1 C11 26.6(2) . . ? O6 Er1 C11 26.9(2) . . ? C7 C1 C6 106.4(7) . . ? C7 C1 C5 112.2(8) . . ? C6 C1 C5 113.7(8) . . ? C7 C1 C2 112.2(8) . . ? C6 C1 C2 111.7(7) . . ? C5 C1 C2 100.7(7) . . ? C8 C2 C9 109.6(9) . . ? C8 C2 C3 112.8(8) . . ? C9 C2 C3 108.7(8) . . ? C8 C2 C1 109.9(8) . . ? C9 C2 C1 115.4(8) . . ? C3 C2 C1 100.2(7) . . ? C10 C3 C4 114.3(7) . . ? C10 C3 C2 111.6(7) . . ? C4 C3 C2 110.2(7) . . ? C10 C3 H3A 106.7 . . ? C4 C3 H3A 106.7 . . ? C2 C3 H3A 106.7 . . ? C3 C4 C5 101.6(7) . . ? C3 C4 H4A 111.5 . . ? C5 C4 H4A 111.5 . . ? C3 C4 H4B 111.5 . . ? C5 C4 H4B 111.5 . . ? H4A C4 H4B 109.3 . . ? C1 C5 C4 105.6(8) . . ? C1 C5 H5A 110.6 . . ? C4 C5 H5A 110.6 . . ? C1 C5 H5B 110.6 . . ? C4 C5 H5B 110.6 . . ? H5A C5 H5B 108.8 . . ? O2 C6 O1 123.8(8) . . ? O2 C6 C1 119.1(8) . . ? O1 C6 C1 117.0(8) . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C9 H9A 109.5 . . ? C2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O3 C10 O4 122.6(8) . . ? O3 C10 C3 118.4(7) . . ? O4 C10 C3 119.0(7) . . ? O5 C11 O6 121.8(8) . . ? O5 C11 Er1 60.2(4) . . ? O6 C11 Er1 61.6(4) . . ? O5 C11 H11C 118.3 . . ? O6 C11 H11C 119.9 . . ? Er1 C11 H11C 178.3 . . ? C6 O1 Er1 144.7(5) . . ? C6 O2 Er1 140.6(6) . 3_534 ? C10 O3 Er1 141.1(6) . 2_444 ? C10 O4 Er1 146.5(5) . 4_453 ? C11 O5 Er1 93.3(5) . . ? C11 O6 Er1 134.0(6) . 3_534 ? C11 O6 Er1 91.5(5) . . ? Er1 O6 Er1 122.2(2) 3_534 . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.617 _refine_diff_density_min -1.114 _refine_diff_density_rms 0.163 _database_code_depnum_ccdc_archive 'CCDC 740835' ####################################################################### # # 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_2 #------------------------------------------------------------------------------ _Attachment Ho.cif _database_code_depnum_ccdc_archive 'CCDC 740836' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H15 Ho O6' _chemical_formula_sum 'C11 H15 Ho O6' _chemical_formula_weight 408.16 _chemical_absolute_configuration rm 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) _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 8.1824(3) _cell_length_b 10.8837(5) _cell_length_c 14.7894(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1317.07(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3823 _cell_measurement_theta_min 3.1143 _cell_measurement_theta_max 27.4758 _exptl_crystal_description Prism _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.3000 _exptl_crystal_size_mid 0.1500 _exptl_crystal_size_min 0.1200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.058 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 6.023 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.7573 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 10145 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2996 _reflns_number_gt 2798 _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^)+(0.0348P)^2^+2.5430P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(2) _refine_ls_number_reflns 2996 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0341 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0747 _refine_ls_wR_factor_gt 0.0731 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 Ho1 Ho 0.42563(3) -0.79602(2) -0.50184(2) 0.02083(9) Uani 1 1 d . . . C1 C 0.2915(8) -0.4055(5) -0.4056(4) 0.0248(13) Uani 1 1 d . . . C2 C 0.2122(11) -0.3789(8) -0.3095(5) 0.047(2) Uani 1 1 d . . . C3 C 0.3235(7) -0.2683(6) -0.2769(4) 0.0257(14) Uani 1 1 d . . . H3A H 0.2744 -0.1929 -0.3009 0.031 Uiso 1 1 calc R . . C4 C 0.4923(13) -0.2796(11) -0.3192(7) 0.069(2) Uani 1 1 d . . . H4A H 0.5756 -0.2913 -0.2734 0.083 Uiso 1 1 calc R . . H4B H 0.5189 -0.2074 -0.3547 0.083 Uiso 1 1 calc R . . C5 C 0.4756(12) -0.3982(11) -0.3819(6) 0.069(2) Uani 1 1 d . . . H5A H 0.5410 -0.3895 -0.4362 0.083 Uiso 1 1 calc R . . H5B H 0.5104 -0.4714 -0.3498 0.083 Uiso 1 1 calc R . . C6 C 0.2423(8) -0.5307(6) -0.4426(4) 0.0263(13) Uani 1 1 d . . . C7 C 0.2409(15) -0.3125(8) -0.4741(7) 0.074(3) Uani 1 1 d . . . H7A H 0.2904 -0.3317 -0.5313 0.111 Uiso 1 1 calc R . . H7B H 0.2757 -0.2324 -0.4550 0.111 Uiso 1 1 calc R . . H7C H 0.1241 -0.3135 -0.4803 0.111 Uiso 1 1 calc R . . C8 C 0.2284(14) -0.4902(11) -0.2502(6) 0.0571(17) Uani 1 1 d . . . H8A H 0.1809 -0.4735 -0.1922 0.086 Uiso 1 1 calc R . . H8B H 0.3419 -0.5102 -0.2429 0.086 Uiso 1 1 calc R . . H8C H 0.1726 -0.5583 -0.2777 0.086 Uiso 1 1 calc R . . C9 C 0.0348(12) -0.3365(9) -0.3128(6) 0.0571(17) Uani 1 1 d . . . H9A H -0.0038 -0.3221 -0.2524 0.086 Uiso 1 1 calc R . . H9B H -0.0309 -0.3988 -0.3408 0.086 Uiso 1 1 calc R . . H9C H 0.0274 -0.2619 -0.3471 0.086 Uiso 1 1 calc R . . C10 C 0.3227(8) -0.2570(5) -0.1752(5) 0.0280(15) Uani 1 1 d . . . C11 C 0.1699(10) -0.9336(7) -0.4261(6) 0.0401(18) Uani 1 1 d . . . H11A H 0.0862 -0.9805 -0.4012 0.048 Uiso 1 1 d R . . O1 O 0.3538(6) -0.5996(4) -0.4720(4) 0.0448(15) Uani 1 1 d . . . O2 O 0.0943(6) -0.5569(5) -0.4467(4) 0.0380(12) Uani 1 1 d . . . O3 O 0.1973(7) -0.2143(5) -0.1375(3) 0.0412(12) Uani 1 1 d . . . O4 O 0.4450(7) -0.2910(5) -0.1314(3) 0.0419(13) Uani 1 1 d . . . O5 O 0.3002(7) -0.9822(5) -0.4435(5) 0.0530(15) Uani 1 1 d . . . O6 O 0.1460(6) -0.8197(4) -0.4411(3) 0.0303(10) 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 Ho1 0.01605(13) 0.02248(13) 0.02397(13) -0.00149(17) -0.00132(18) 0.00099(9) C1 0.030(3) 0.019(3) 0.026(3) -0.005(2) 0.005(3) -0.002(3) C2 0.050(5) 0.054(5) 0.037(4) -0.011(4) 0.003(4) -0.015(4) C3 0.030(4) 0.031(3) 0.016(3) -0.006(2) -0.003(2) -0.003(3) C4 0.056(4) 0.099(6) 0.053(4) -0.032(4) 0.014(3) -0.031(4) C5 0.056(4) 0.099(6) 0.053(4) -0.032(4) 0.014(3) -0.031(4) C6 0.028(4) 0.023(3) 0.028(3) -0.003(2) -0.001(3) -0.003(3) C7 0.110(9) 0.040(5) 0.071(7) -0.005(4) -0.028(6) 0.000(5) C8 0.061(5) 0.061(4) 0.049(3) 0.002(3) -0.001(3) -0.010(3) C9 0.061(5) 0.061(4) 0.049(3) 0.002(3) -0.001(3) -0.010(3) C10 0.033(4) 0.028(3) 0.022(3) -0.003(2) 0.001(3) -0.002(3) C11 0.030(4) 0.033(4) 0.058(5) 0.017(3) 0.000(4) -0.006(3) O1 0.042(3) 0.023(2) 0.070(4) -0.016(2) 0.009(3) -0.003(2) O2 0.026(3) 0.033(3) 0.055(3) -0.016(2) -0.003(2) -0.005(2) O3 0.042(3) 0.054(3) 0.027(2) -0.006(2) 0.011(2) 0.001(3) O4 0.045(3) 0.058(3) 0.023(2) -0.003(2) -0.012(2) 0.004(3) O5 0.035(3) 0.031(3) 0.093(5) 0.012(3) 0.006(3) 0.002(3) O6 0.023(2) 0.029(2) 0.038(3) 0.0076(19) 0.000(2) 0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ho1 O4 2.238(5) 3_644 ? Ho1 O2 2.246(5) 4_534 ? Ho1 O3 2.248(5) 2_544 ? Ho1 O1 2.260(5) . ? Ho1 O6 2.355(5) 4_534 ? Ho1 O5 2.431(5) . ? Ho1 O6 2.472(5) . ? Ho1 C11 2.806(7) . ? C1 C7 1.491(11) . ? C1 C6 1.523(8) . ? C1 C5 1.549(12) . ? C1 C2 1.589(10) . ? C2 C8 1.501(13) . ? C2 C9 1.524(13) . ? C2 C3 1.585(10) . ? C3 C10 1.508(9) . ? C3 C4 1.522(12) . ? C3 H3A 0.9800 . ? C4 C5 1.594(13) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O2 1.246(8) . ? C6 O1 1.259(8) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 O4 1.248(8) . ? C10 O3 1.257(8) . ? C11 O5 1.217(9) . ? C11 O6 1.274(8) . ? C11 H11A 0.9301 . ? O2 Ho1 2.246(5) 4_434 ? O3 Ho1 2.248(5) 2_545 ? O4 Ho1 2.238(5) 3_654 ? O6 Ho1 2.355(5) 4_434 ? 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 Ho1 O2 91.4(2) 3_644 4_534 ? O4 Ho1 O3 175.4(2) 3_644 2_544 ? O2 Ho1 O3 90.5(2) 4_534 2_544 ? O4 Ho1 O1 85.9(2) 3_644 . ? O2 Ho1 O1 154.13(19) 4_534 . ? O3 Ho1 O1 90.6(2) 2_544 . ? O4 Ho1 O6 86.57(18) 3_644 4_534 ? O2 Ho1 O6 77.85(18) 4_534 4_534 ? O3 Ho1 O6 89.77(18) 2_544 4_534 ? O1 Ho1 O6 76.31(17) . 4_534 ? O4 Ho1 O5 84.7(2) 3_644 . ? O2 Ho1 O5 77.6(2) 4_534 . ? O3 Ho1 O5 99.8(2) 2_544 . ? O1 Ho1 O5 127.5(2) . . ? O6 Ho1 O5 153.69(18) 4_534 . ? O4 Ho1 O6 96.93(18) 3_644 . ? O2 Ho1 O6 128.14(17) 4_534 . ? O3 Ho1 O6 85.14(18) 2_544 . ? O1 Ho1 O6 77.70(16) . . ? O6 Ho1 O6 153.44(8) 4_534 . ? O5 Ho1 O6 52.63(17) . . ? O4 Ho1 C11 90.8(2) 3_644 . ? O2 Ho1 C11 102.3(2) 4_534 . ? O3 Ho1 C11 92.8(2) 2_544 . ? O1 Ho1 C11 103.5(2) . . ? O6 Ho1 C11 177.4(2) 4_534 . ? O5 Ho1 C11 25.6(2) . . ? O6 Ho1 C11 27.00(18) . . ? C7 C1 C6 106.8(6) . . ? C7 C1 C5 112.9(8) . . ? C6 C1 C5 112.6(6) . . ? C7 C1 C2 111.8(7) . . ? C6 C1 C2 112.1(5) . . ? C5 C1 C2 100.7(6) . . ? C8 C2 C9 110.3(8) . . ? C8 C2 C3 112.7(7) . . ? C9 C2 C3 109.1(7) . . ? C8 C2 C1 109.8(7) . . ? C9 C2 C1 114.5(7) . . ? C3 C2 C1 100.1(6) . . ? C10 C3 C4 114.9(6) . . ? C10 C3 C2 111.2(5) . . ? C4 C3 C2 109.5(6) . . ? C10 C3 H3A 106.9 . . ? C4 C3 H3A 106.9 . . ? C2 C3 H3A 106.9 . . ? C3 C4 C5 103.1(7) . . ? C3 C4 H4A 111.1 . . ? C5 C4 H4A 111.1 . . ? C3 C4 H4B 111.1 . . ? C5 C4 H4B 111.1 . . ? H4A C4 H4B 109.1 . . ? C1 C5 C4 104.9(8) . . ? C1 C5 H5A 110.8 . . ? C4 C5 H5A 110.8 . . ? C1 C5 H5B 110.8 . . ? C4 C5 H5B 110.8 . . ? H5A C5 H5B 108.9 . . ? O2 C6 O1 123.5(6) . . ? O2 C6 C1 118.7(6) . . ? O1 C6 C1 117.8(6) . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C9 H9A 109.5 . . ? C2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O4 C10 O3 122.3(7) . . ? O4 C10 C3 119.3(6) . . ? O3 C10 C3 118.4(6) . . ? O5 C11 O6 121.4(7) . . ? O5 C11 Ho1 59.7(4) . . ? O6 C11 Ho1 61.7(4) . . ? O5 C11 H11A 119.3 . . ? O6 C11 H11A 119.3 . . ? Ho1 C11 H11A 178.9 . . ? C6 O1 Ho1 145.0(4) . . ? C6 O2 Ho1 141.0(5) . 4_434 ? C10 O3 Ho1 141.3(5) . 2_545 ? C10 O4 Ho1 147.5(5) . 3_654 ? C11 O5 Ho1 94.7(4) . . ? C11 O6 Ho1 134.5(5) . 4_434 ? C11 O6 Ho1 91.3(4) . . ? Ho1 O6 Ho1 121.52(18) 4_434 . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.319 _refine_diff_density_min -1.197 _refine_diff_density_rms 0.148