# Electronic Supplementary Material (ESI) for Polymer Chemistry # 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_global data_buch13 #TrackingRef '17440_web_deposit_cif_file_0_JoergUnold_1359907429.buch13.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 O4' _chemical_formula_sum 'C10 H10 O4' _chemical_formula_weight 194.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8784(5) _cell_length_b 8.2785(6) _cell_length_c 8.5427(6) _cell_angle_alpha 78.119(3) _cell_angle_beta 87.930(3) _cell_angle_gamma 88.399(3) _cell_volume 475.61(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1461 _cell_measurement_theta_min 5.29 _cell_measurement_theta_max 66.62 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.892 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4696 _exptl_absorpt_correction_T_max 0.7428 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source I\mS _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEX II Duo' _diffrn_measurement_method 'Omega + Phi Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7314 _diffrn_reflns_av_R_equivalents 0.0573 _diffrn_reflns_av_sigmaI/netI 0.0860 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 5.29 _diffrn_reflns_theta_max 66.62 _reflns_number_total 1583 _reflns_number_gt 1461 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II Software Suite, 2008' _computing_cell_refinement 'Bruker APEX II Software Suite, 2008' _computing_data_reduction 'Bruker APEX II Software Suite, 2008' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-plus, XP (Sheldrick, 1991)' _computing_publication_material ? _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^)+(0.0238P)^2^+0.1988P] 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 0.023(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1583 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0765 _refine_ls_wR_factor_gt 0.0758 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 O1 O 0.37811(12) 0.42049(10) 0.66875(11) 0.0207(3) Uani 1 1 d . . . C1 C 0.30364(17) 0.34053(14) 0.58217(16) 0.0163(3) Uani 1 1 d . . . O2 O 0.34555(13) 0.35831(11) 0.42805(11) 0.0210(3) Uani 1 1 d . . . H2A H 0.445(3) 0.445(3) 0.396(3) 0.056(6) Uiso 1 1 d . . . C2 C 0.08333(17) 0.32746(15) 0.89541(16) 0.0168(3) Uani 1 1 d . . . O3 O 0.15373(13) 0.34169(11) 1.02160(12) 0.0225(3) Uani 1 1 d . . . C3 C 0.15213(17) 0.21118(14) 0.64126(15) 0.0160(3) Uani 1 1 d . . . H3 H 0.2057 0.1063 0.6144 0.019 Uiso 1 1 calc R . . O4 O -0.04007(13) 0.43458(11) 0.81564(12) 0.0230(3) Uani 1 1 d . . . H4A H -0.078(3) 0.522(3) 0.880(3) 0.064(6) Uiso 1 1 d . . . C4 C 0.12190(17) 0.17641(14) 0.82410(15) 0.0161(3) Uani 1 1 d . . . H4 H 0.0028 0.1080 0.8488 0.019 Uiso 1 1 calc R . . C5 C -0.03573(18) 0.25430(15) 0.54461(16) 0.0191(3) Uani 1 1 d . . . H5A H -0.0887 0.3625 0.5601 0.023 Uiso 1 1 calc R . . H5B H -0.0035 0.2637 0.4293 0.023 Uiso 1 1 calc R . . C6 C -0.18363(18) 0.12875(16) 0.59466(16) 0.0189(3) Uani 1 1 d . . . C7 C -0.29998(19) 0.02424(17) 0.63831(17) 0.0229(3) Uani 1 1 d . . . H7 H -0.3930 -0.0593 0.6732 0.027 Uiso 1 1 calc R . . C8 C 0.28980(17) 0.07073(15) 0.90913(16) 0.0175(3) Uani 1 1 d . . . H8A H 0.4146 0.1250 0.8730 0.021 Uiso 1 1 calc R . . H8B H 0.2740 0.0639 1.0259 0.021 Uiso 1 1 calc R . . C9 C 0.29673(17) -0.09685(15) 0.87687(16) 0.0185(3) Uani 1 1 d . . . C10 C 0.30436(19) -0.23260(16) 0.85118(18) 0.0247(3) Uani 1 1 d . . . H10 H 0.3105 -0.3412 0.8306 0.030 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 O1 0.0229(5) 0.0209(5) 0.0196(6) -0.0071(4) 0.0025(4) -0.0072(4) C1 0.0161(6) 0.0152(6) 0.0179(7) -0.0047(5) -0.0006(5) 0.0024(5) O2 0.0233(5) 0.0232(5) 0.0171(6) -0.0048(4) 0.0029(4) -0.0084(4) C2 0.0146(6) 0.0172(6) 0.0177(7) -0.0015(5) 0.0031(5) -0.0035(4) O3 0.0222(5) 0.0250(5) 0.0230(6) -0.0107(4) -0.0019(4) 0.0006(4) C3 0.0165(6) 0.0147(6) 0.0172(7) -0.0041(5) 0.0006(5) -0.0012(5) O4 0.0278(5) 0.0196(5) 0.0214(6) -0.0046(4) -0.0003(4) 0.0056(4) C4 0.0157(6) 0.0155(6) 0.0171(7) -0.0034(5) 0.0003(5) -0.0027(5) C5 0.0187(6) 0.0190(6) 0.0195(8) -0.0028(5) -0.0018(5) -0.0031(5) C6 0.0190(6) 0.0226(7) 0.0168(7) -0.0076(5) -0.0020(5) 0.0001(5) C7 0.0220(7) 0.0267(7) 0.0223(8) -0.0103(6) 0.0038(5) -0.0076(5) C8 0.0181(6) 0.0165(6) 0.0179(7) -0.0035(5) -0.0005(5) -0.0017(5) C9 0.0155(6) 0.0212(7) 0.0178(7) -0.0017(5) 0.0008(5) -0.0014(5) C10 0.0240(7) 0.0190(7) 0.0315(9) -0.0064(6) 0.0049(6) -0.0028(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 O1 C1 1.2229(15) . ? C1 O2 1.3166(16) . ? C1 C3 1.5130(17) . ? O2 H2A 1.00(2) . ? C2 O3 1.2263(16) . ? C2 O4 1.3123(16) . ? C2 C4 1.5128(18) . ? C3 C4 1.5364(18) . ? C3 C5 1.5520(17) . ? C3 H3 1.0000 . ? O4 H4A 1.02(2) . ? C4 C8 1.5392(17) . ? C4 H4 1.0000 . ? C5 C6 1.4638(18) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.1884(19) . ? C7 H7 0.9500 . ? C8 C9 1.4682(18) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.1880(19) . ? C10 H10 0.9500 . ? 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 123.77(11) . . ? O1 C1 C3 123.33(11) . . ? O2 C1 C3 112.90(11) . . ? C1 O2 H2A 109.4(12) . . ? O3 C2 O4 123.86(12) . . ? O3 C2 C4 122.04(11) . . ? O4 C2 C4 113.97(11) . . ? C1 C3 C4 112.54(10) . . ? C1 C3 C5 109.98(10) . . ? C4 C3 C5 115.28(10) . . ? C1 C3 H3 106.1 . . ? C4 C3 H3 106.1 . . ? C5 C3 H3 106.1 . . ? C2 O4 H4A 110.0(13) . . ? C2 C4 C3 115.16(10) . . ? C2 C4 C8 110.50(10) . . ? C3 C4 C8 111.77(10) . . ? C2 C4 H4 106.3 . . ? C3 C4 H4 106.3 . . ? C8 C4 H4 106.3 . . ? C6 C5 C3 111.60(10) . . ? C6 C5 H5A 109.3 . . ? C3 C5 H5A 109.3 . . ? C6 C5 H5B 109.3 . . ? C3 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? C7 C6 C5 178.09(14) . . ? C6 C7 H7 180.0 . . ? C9 C8 C4 112.22(11) . . ? C9 C8 H8A 109.2 . . ? C4 C8 H8A 109.2 . . ? C9 C8 H8B 109.2 . . ? C4 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C10 C9 C8 179.30(14) . . ? C9 C10 H10 180.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C3 C4 -7.24(16) . . . . ? O2 C1 C3 C4 173.14(10) . . . . ? O1 C1 C3 C5 122.77(13) . . . . ? O2 C1 C3 C5 -56.85(13) . . . . ? O3 C2 C4 C3 -140.35(11) . . . . ? O4 C2 C4 C3 43.64(14) . . . . ? O3 C2 C4 C8 -12.53(16) . . . . ? O4 C2 C4 C8 171.46(10) . . . . ? C1 C3 C4 C2 51.60(13) . . . . ? C5 C3 C4 C2 -75.65(13) . . . . ? C1 C3 C4 C8 -75.58(12) . . . . ? C5 C3 C4 C8 157.18(10) . . . . ? C1 C3 C5 C6 178.03(11) . . . . ? C4 C3 C5 C6 -53.45(14) . . . . ? C3 C5 C6 C7 -3(4) . . . . ? C2 C4 C8 C9 163.90(10) . . . . ? C3 C4 C8 C9 -66.45(13) . . . . ? C4 C8 C9 C10 158(12) . . . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 66.62 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.209 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 923151' ####################################################################### # # 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_global # Attachment '17441_web_deposit_cif_file_1_JoergUnold_1359907429.buch18.cif' data_buch18 #TrackingRef '17441_web_deposit_cif_file_1_JoergUnold_1359907429.buch18.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H14 O2' _chemical_absolute_configuration syn _chemical_formula_sum 'C10 H14 O2' _chemical_formula_weight 166.21 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 14.8047(19) _cell_length_b 24.843(3) _cell_length_c 5.0851(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.707(6) _cell_angle_gamma 90.00 _cell_volume 1831.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1804 _cell_measurement_theta_min 1.63 _cell_measurement_theta_max 30.67 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9430 _exptl_absorpt_correction_T_max 0.9749 _exptl_absorpt_process_details 'Blessing, 1995' _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 Triumph _diffrn_measurement_device_type 'Bruker Kappa' _diffrn_measurement_method 'Omega + Phi Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10773 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 3 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 30.67 _reflns_number_total 3955 _reflns_number_gt 1804 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II' _computing_cell_refinement 'APEX II' _computing_data_reduction 'APEX II' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP ' _computing_publication_material ? _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^)+(0.0510P)^2^+0.8175P] 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 3(3) _refine_ls_number_reflns 3955 _refine_ls_number_parameters 221 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0707 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.1120 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.004 _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 O1A O 0.22813(13) 0.27314(8) 0.9015(4) 0.0156(5) Uani 1 1 d . . . H1A H 0.2447 0.2604 1.0569 0.023 Uiso 1 1 calc R . . C1A C 0.16481(17) 0.35226(11) 0.6642(5) 0.0119(6) Uani 1 1 d . . . H1A1 H 0.1468 0.3291 0.5013 0.014 Uiso 1 1 calc R . . O2A O 0.02947(15) 0.47669(9) 0.4038(4) 0.0165(6) Uani 1 1 d . . . H2A H 0.0305 0.4971 0.2729 0.025 Uiso 1 1 calc R . . C2A C 0.09169(19) 0.39725(13) 0.6455(5) 0.0112(6) Uani 1 1 d . . . H2A1 H 0.1091 0.4203 0.8092 0.013 Uiso 1 1 calc R . . C3A C 0.1659(2) 0.31708(11) 0.9070(6) 0.0156(7) Uani 1 1 d . . . H3A1 H 0.1860 0.3384 1.0732 0.019 Uiso 1 1 calc R . . H3A2 H 0.1031 0.3032 0.9052 0.019 Uiso 1 1 calc R . . C4A C 0.0919(2) 0.43295(13) 0.4001(6) 0.0139(7) Uani 1 1 d . . . H4A1 H 0.1549 0.4469 0.4049 0.017 Uiso 1 1 calc R . . H4A2 H 0.0726 0.4117 0.2334 0.017 Uiso 1 1 calc R . . C5A C 0.26280(19) 0.37376(11) 0.6678(6) 0.0153(7) Uani 1 1 d . . . H5A1 H 0.3070 0.3434 0.7014 0.018 Uiso 1 1 calc R . . H5A2 H 0.2649 0.3889 0.4890 0.018 Uiso 1 1 calc R . . C6A C 0.29191(19) 0.41552(12) 0.8736(6) 0.0174(7) Uani 1 1 d . . . C7A C 0.3142(2) 0.44851(13) 1.0419(7) 0.0246(8) Uani 1 1 d . . . H7A H 0.3321 0.4750 1.1771 0.029 Uiso 1 1 calc R . . C8A C -0.0064(2) 0.37579(12) 0.6367(6) 0.0142(7) Uani 1 1 d . . . H8A1 H -0.0093 0.3602 0.8140 0.017 Uiso 1 1 calc R . . H8A2 H -0.0503 0.4063 0.6039 0.017 Uiso 1 1 calc R . . C9A C -0.0351(2) 0.33508(13) 0.4304(7) 0.0167(8) Uani 1 1 d . . . C10A C -0.0580(3) 0.30145(15) 0.2627(8) 0.0244(9) Uani 1 1 d . . . H10A H -0.0764 0.2747 0.1292 0.029 Uiso 1 1 calc R . . O1B O 0.22820(16) 0.22686(9) 0.4015(4) 0.0158(6) Uani 1 1 d . . . H1B H 0.2436 0.2400 0.5562 0.024 Uiso 1 1 calc R . . C1B C 0.1644(2) 0.14758(14) 0.1636(6) 0.0121(7) Uani 1 1 d . . . H1B1 H 0.1461 0.1707 0.0004 0.015 Uiso 1 1 calc R . . O2B O 0.02939(16) 0.02330(9) -0.0964(5) 0.0171(6) Uani 1 1 d . . . H2B H 0.0318 0.0022 -0.2241 0.026 Uiso 1 1 calc R . . C2B C 0.0928(2) 0.10224(15) 0.1447(6) 0.0121(7) Uani 1 1 d . . . H2B1 H 0.1105 0.0792 0.3081 0.015 Uiso 1 1 calc R . . C3B C 0.1660(2) 0.18283(14) 0.4066(7) 0.0152(8) Uani 1 1 d . . . H3B1 H 0.1033 0.1967 0.4056 0.018 Uiso 1 1 calc R . . H3B2 H 0.1863 0.1615 0.5726 0.018 Uiso 1 1 calc R . . C4B C 0.0921(2) 0.06705(13) -0.1001(6) 0.0139(7) Uani 1 1 d . . . H4B1 H 0.0725 0.0885 -0.2660 0.017 Uiso 1 1 calc R . . H4B2 H 0.1549 0.0530 -0.0972 0.017 Uiso 1 1 calc R . . C5B C 0.2628(2) 0.12631(13) 0.1677(6) 0.0152(8) Uani 1 1 d . . . H5B1 H 0.2651 0.1112 -0.0109 0.018 Uiso 1 1 calc R . . H5B2 H 0.3068 0.1568 0.2014 0.018 Uiso 1 1 calc R . . C6B C 0.2920(2) 0.08461(15) 0.3740(7) 0.0179(8) Uani 1 1 d . . . C7B C 0.3141(3) 0.05128(15) 0.5413(9) 0.0248(9) Uani 1 1 d . . . H7B H 0.3318 0.0246 0.6754 0.030 Uiso 1 1 calc R . . C8B C -0.0061(2) 0.12416(13) 0.1365(7) 0.0148(8) Uani 1 1 d . . . H8B1 H -0.0502 0.0938 0.1045 0.018 Uiso 1 1 calc R . . H8B2 H -0.0087 0.1398 0.3139 0.018 Uiso 1 1 calc R . . C9B C -0.0349(2) 0.16478(15) -0.0695(8) 0.0173(8) Uani 1 1 d . . . C10B C -0.0582(3) 0.19856(16) -0.2372(8) 0.0253(9) Uani 1 1 d . . . H10B H -0.0766 0.2254 -0.3705 0.030 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 O1A 0.0191(10) 0.0138(9) 0.0132(10) 0.0016(7) 0.0016(8) 0.0037(8) C1A 0.0096(11) 0.0114(12) 0.0153(12) -0.0014(9) 0.0037(10) 0.0014(9) O2A 0.0224(12) 0.0126(11) 0.0149(12) 0.0016(8) 0.0044(10) 0.0037(9) C2A 0.0196(14) 0.0104(13) 0.0043(10) 0.0043(9) 0.0041(11) 0.0028(10) C3A 0.0175(13) 0.0139(13) 0.0167(14) 0.0021(11) 0.0063(12) -0.0001(10) C4A 0.0170(15) 0.0148(14) 0.0109(13) 0.0021(11) 0.0050(12) 0.0021(12) C5A 0.0144(12) 0.0176(13) 0.0154(13) 0.0002(10) 0.0063(11) 0.0008(10) C6A 0.0148(12) 0.0191(14) 0.0172(14) 0.0034(11) 0.0007(11) -0.0034(11) C7A 0.0265(15) 0.0211(15) 0.0244(17) 0.0011(13) 0.0011(14) -0.0089(13) C8A 0.0106(13) 0.0151(15) 0.0176(15) 0.0017(12) 0.0041(13) -0.0014(11) C9A 0.0138(15) 0.0159(15) 0.0202(17) 0.0041(12) 0.0030(14) -0.0006(12) C10A 0.0238(17) 0.0282(19) 0.0197(18) -0.0009(15) 0.0006(15) -0.0072(16) O1B 0.0198(12) 0.0139(12) 0.0131(11) -0.0014(9) 0.0020(10) -0.0036(10) C1B 0.0112(15) 0.0128(15) 0.0128(14) 0.0006(11) 0.0032(13) 0.0018(12) O2B 0.0225(13) 0.0126(12) 0.0162(13) -0.0021(9) 0.0041(11) -0.0041(10) C2B 0.0098(13) 0.0170(16) 0.0101(12) 0.0024(11) 0.0032(12) 0.0048(11) C3B 0.0157(16) 0.0151(16) 0.0157(16) -0.0010(13) 0.0050(14) -0.0009(13) C4B 0.0166(15) 0.0138(15) 0.0125(14) -0.0033(12) 0.0055(13) -0.0039(13) C5B 0.0144(16) 0.0170(17) 0.0154(15) 0.0005(13) 0.0061(14) -0.0006(13) C6B 0.0154(16) 0.0184(17) 0.0192(17) -0.0034(14) 0.0021(14) 0.0025(14) C7B 0.0278(18) 0.0184(18) 0.028(2) 0.0001(16) 0.0043(17) 0.0073(16) C8B 0.0124(15) 0.0154(16) 0.0169(16) -0.0016(13) 0.0039(14) 0.0008(12) C9B 0.0132(16) 0.0176(17) 0.0209(18) -0.0048(13) 0.0032(15) 0.0014(13) C10B 0.0242(18) 0.030(2) 0.0191(19) 0.0006(16) -0.0012(16) 0.0079(17) _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 O1A C3A 1.432(3) . ? O1A H1A 0.8400 . ? C1A C3A 1.510(4) . ? C1A C5A 1.543(4) . ? C1A C2A 1.545(3) . ? C1A H1A1 1.0000 . ? O2A C4A 1.429(4) . ? O2A H2A 0.8400 . ? C2A C4A 1.532(4) . ? C2A C8A 1.539(4) . ? C2A H2A1 1.0000 . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C5A C6A 1.475(4) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C6A C7A 1.183(5) . ? C7A H7A 0.9500 . ? C8A C9A 1.457(5) . ? C8A H8A1 0.9900 . ? C8A H8A2 0.9900 . ? C9A C10A 1.193(5) . ? C10A H10A 0.9500 . ? O1B C3B 1.433(4) . ? O1B H1B 0.8400 . ? C1B C3B 1.511(5) . ? C1B C2B 1.536(4) . ? C1B C5B 1.546(5) . ? C1B H1B1 1.0000 . ? O2B C4B 1.432(4) . ? O2B H2B 0.8400 . ? C2B C4B 1.519(5) . ? C2B C8B 1.555(5) . ? C2B H2B1 1.0000 . ? C3B H3B1 0.9900 . ? C3B H3B2 0.9900 . ? C4B H4B1 0.9900 . ? C4B H4B2 0.9900 . ? C5B C6B 1.476(5) . ? C5B H5B1 0.9900 . ? C5B H5B2 0.9900 . ? C6B C7B 1.184(5) . ? C7B H7B 0.9500 . ? C8B C9B 1.455(5) . ? C8B H8B1 0.9900 . ? C8B H8B2 0.9900 . ? C9B C10B 1.196(6) . ? C10B H10B 0.9500 . ? 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 C3A O1A H1A 109.5 . . ? C3A C1A C5A 109.7(2) . . ? C3A C1A C2A 111.1(2) . . ? C5A C1A C2A 113.3(2) . . ? C3A C1A H1A1 107.5 . . ? C5A C1A H1A1 107.5 . . ? C2A C1A H1A1 107.5 . . ? C4A O2A H2A 109.5 . . ? C4A C2A C8A 109.6(2) . . ? C4A C2A C1A 110.6(2) . . ? C8A C2A C1A 113.4(2) . . ? C4A C2A H2A1 107.7 . . ? C8A C2A H2A1 107.7 . . ? C1A C2A H2A1 107.7 . . ? O1A C3A C1A 109.0(2) . . ? O1A C3A H3A1 109.9 . . ? C1A C3A H3A1 109.9 . . ? O1A C3A H3A2 109.9 . . ? C1A C3A H3A2 109.9 . . ? H3A1 C3A H3A2 108.3 . . ? O2A C4A C2A 108.7(2) . . ? O2A C4A H4A1 109.9 . . ? C2A C4A H4A1 109.9 . . ? O2A C4A H4A2 109.9 . . ? C2A C4A H4A2 109.9 . . ? H4A1 C4A H4A2 108.3 . . ? C6A C5A C1A 113.0(2) . . ? C6A C5A H5A1 109.0 . . ? C1A C5A H5A1 109.0 . . ? C6A C5A H5A2 109.0 . . ? C1A C5A H5A2 109.0 . . ? H5A1 C5A H5A2 107.8 . . ? C7A C6A C5A 178.7(4) . . ? C6A C7A H7A 180.0 . . ? C9A C8A C2A 113.4(3) . . ? C9A C8A H8A1 108.9 . . ? C2A C8A H8A1 108.9 . . ? C9A C8A H8A2 108.9 . . ? C2A C8A H8A2 108.9 . . ? H8A1 C8A H8A2 107.7 . . ? C10A C9A C8A 179.5(4) . . ? C9A C10A H10A 180.0 . . ? C3B O1B H1B 109.5 . . ? C3B C1B C2B 111.9(2) . . ? C3B C1B C5B 109.2(3) . . ? C2B C1B C5B 112.7(2) . . ? C3B C1B H1B1 107.6 . . ? C2B C1B H1B1 107.6 . . ? C5B C1B H1B1 107.6 . . ? C4B O2B H2B 109.5 . . ? C4B C2B C1B 111.3(2) . . ? C4B C2B C8B 109.3(3) . . ? C1B C2B C8B 112.3(2) . . ? C4B C2B H2B1 108.0 . . ? C1B C2B H2B1 108.0 . . ? C8B C2B H2B1 108.0 . . ? O1B C3B C1B 109.3(3) . . ? O1B C3B H3B1 109.8 . . ? C1B C3B H3B1 109.8 . . ? O1B C3B H3B2 109.8 . . ? C1B C3B H3B2 109.8 . . ? H3B1 C3B H3B2 108.3 . . ? O2B C4B C2B 108.8(3) . . ? O2B C4B H4B1 109.9 . . ? C2B C4B H4B1 109.9 . . ? O2B C4B H4B2 109.9 . . ? C2B C4B H4B2 109.9 . . ? H4B1 C4B H4B2 108.3 . . ? C6B C5B C1B 112.9(3) . . ? C6B C5B H5B1 109.0 . . ? C1B C5B H5B1 109.0 . . ? C6B C5B H5B2 109.0 . . ? C1B C5B H5B2 109.0 . . ? H5B1 C5B H5B2 107.8 . . ? C7B C6B C5B 178.8(4) . . ? C6B C7B H7B 180.0 . . ? C9B C8B C2B 113.5(3) . . ? C9B C8B H8B1 108.9 . . ? C2B C8B H8B1 108.9 . . ? C9B C8B H8B2 108.9 . . ? C2B C8B H8B2 108.9 . . ? H8B1 C8B H8B2 107.7 . . ? C10B C9B C8B 179.3(4) . . ? C9B C10B H10B 180.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3A C1A C2A C4A 179.4(3) . . . . ? C5A C1A C2A C4A 55.4(3) . . . . ? C3A C1A C2A C8A -57.0(3) . . . . ? C5A C1A C2A C8A 178.9(3) . . . . ? C5A C1A C3A O1A -59.4(3) . . . . ? C2A C1A C3A O1A 174.5(2) . . . . ? C8A C2A C4A O2A 59.5(3) . . . . ? C1A C2A C4A O2A -174.9(2) . . . . ? C3A C1A C5A C6A -72.7(3) . . . . ? C2A C1A C5A C6A 52.1(3) . . . . ? C1A C5A C6A C7A 32(16) . . . . ? C4A C2A C8A C9A 71.9(3) . . . . ? C1A C2A C8A C9A -52.2(3) . . . . ? C2A C8A C9A C10A 73(50) . . . . ? C3B C1B C2B C4B -179.8(3) . . . . ? C5B C1B C2B C4B -56.4(3) . . . . ? C3B C1B C2B C8B 57.3(3) . . . . ? C5B C1B C2B C8B -179.2(3) . . . . ? C2B C1B C3B O1B -175.2(2) . . . . ? C5B C1B C3B O1B 59.3(4) . . . . ? C1B C2B C4B O2B 175.7(2) . . . . ? C8B C2B C4B O2B -59.8(3) . . . . ? C3B C1B C5B C6B 72.9(4) . . . . ? C2B C1B C5B C6B -52.1(3) . . . . ? C1B C5B C6B C7B -6(21) . . . . ? C4B C2B C8B C9B -71.5(4) . . . . ? C1B C2B C8B C9B 52.5(3) . . . . ? C2B C8B C9B C10B -79(41) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.67 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.225 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 923152'