# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email amassa@unisa.it _publ_contact_author_name 'Antonio Massa' loop_ _publ_author_name 'Vijaykumar More' 'Antonia Di Mola' 'Gianluca Croce' 'Consiglia Tedesco' 'Carmen Petronzi' 'Paolo De Caprariis' 'Rosanna Filosa' 'Antonio Massa' data_dcm_long _database_code_depnum_ccdc_archive 'CCDC 837214' #TrackingRef '- compound 3e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 N0 O2 Si' _chemical_formula_weight 202.28 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' Si Si 0.0817 0.0704 '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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 9.8157(4) _cell_length_b 15.5367(5) _cell_length_c 14.1068(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.289(4) _cell_angle_gamma 90.00 _cell_volume 2128.86(15) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.191 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _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 29674 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.20 _diffrn_reflns_theta_max 30.38 _reflns_number_total 5512 _reflns_number_gt 2820 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1080P)^2^+0.5919P] 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 5512 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1271 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.2241 _refine_ls_wR_factor_gt 0.1751 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _refine_ls_shift/su_max 0.100 _refine_ls_shift/su_mean 0.011 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 Si01 Si 0.27335(9) -0.13539(6) 1.01982(6) 0.0787(3) Uani 1 1 d . . . O002 O 0.14029(18) -0.08747(10) 0.95838(12) 0.0634(5) Uani 1 1 d . . . O004 O -0.17581(17) -0.00576(11) 0.69847(12) 0.0652(5) Uani 1 1 d . . . O005 O 0.0088(2) -0.07639(18) 0.66100(14) 0.0997(8) Uani 1 1 d . . . O003 O -0.0157(3) -0.22773(14) 0.8315(2) 0.1215(10) Uani 1 1 d . . . C007 C 0.1765(2) 0.01905(14) 0.84001(17) 0.0557(6) Uani 1 1 d . . . C008 C 0.1322(3) 0.09030(15) 0.8857(2) 0.0687(7) Uani 1 1 d . . . H008 H 0.0704 0.0834 0.9293 0.082 Uiso 1 1 calc R . . C010 C 0.1215(2) -0.06942(14) 0.85890(17) 0.0547(6) Uani 1 1 d . . . H010 H 0.1698 -0.1128 0.8259 0.066 Uiso 1 1 calc R . . C011 C -0.0323(2) -0.07495(15) 0.82353(18) 0.0574(6) Uani 1 1 d . . . H011 H -0.0812 -0.0345 0.8600 0.069 Uiso 1 1 calc R . . C012 C -0.0878(3) -0.16588(19) 0.8348(2) 0.0771(8) Uani 1 1 d . . . C013 C -0.2243(3) 0.02485(18) 0.5996(2) 0.0713(7) Uani 1 1 d . . . C014 C 0.2696(3) 0.03209(16) 0.77489(19) 0.0624(6) Uani 1 1 d . . . C015 C -0.0621(3) -0.05258(17) 0.71804(19) 0.0645(7) Uani 1 1 d . . . C016 C 0.1789(4) 0.17181(18) 0.8674(2) 0.0874(9) Uani 1 1 d . . . H016 H 0.1486 0.2191 0.8990 0.105 Uiso 1 1 calc R . . C017 C -0.2360(4) -0.1728(2) 0.8461(3) 0.1007(11) Uani 1 1 d . . . H01A H -0.2602 -0.2323 0.8512 0.151 Uiso 1 1 calc R . . H01B H -0.2914 -0.1477 0.7913 0.151 Uiso 1 1 calc R . . H01C H -0.2519 -0.1427 0.9029 0.151 Uiso 1 1 calc R . . C018 C 0.2705(4) 0.1835(2) 0.8024(3) 0.0899(10) Uani 1 1 d . . . H018 H 0.3010 0.2385 0.7902 0.108 Uiso 1 1 calc R . . C019 C 0.3156(3) 0.11463(19) 0.7564(2) 0.0801(8) Uani 1 1 d . . . H019 H 0.3770 0.1224 0.7127 0.096 Uiso 1 1 calc R . . C020 C -0.1197(4) 0.0872(2) 0.5702(3) 0.1018(11) Uani 1 1 d . . . H02A H -0.0365 0.0568 0.5633 0.153 Uiso 1 1 calc R . . H02B H -0.1000 0.1309 0.6184 0.153 Uiso 1 1 calc R . . H02C H -0.1560 0.1135 0.5103 0.153 Uiso 1 1 calc R . . C021 C -0.2529(4) -0.0508(3) 0.5320(3) 0.1029(11) Uani 1 1 d . . . H02D H -0.1679 -0.0793 0.5255 0.154 Uiso 1 1 calc R . . H02E H -0.2953 -0.0306 0.4704 0.154 Uiso 1 1 calc R . . H02F H -0.3135 -0.0905 0.5572 0.154 Uiso 1 1 calc R . . C022 C -0.3579(3) 0.0697(2) 0.6115(3) 0.1012(11) Uani 1 1 d . . . H02G H -0.4208 0.0288 0.6322 0.152 Uiso 1 1 calc R . . H02H H -0.3978 0.0942 0.5514 0.152 Uiso 1 1 calc R . . H02I H -0.3399 0.1145 0.6585 0.152 Uiso 1 1 calc R . . C023 C 0.3737(5) -0.1974(3) 0.9448(3) 0.1280(17) Uani 1 1 d . . . H02J H 0.4039 -0.1603 0.8975 0.192 Uiso 1 1 calc R . . H02K H 0.3178 -0.2426 0.9134 0.192 Uiso 1 1 calc R . . H02L H 0.4524 -0.2219 0.9838 0.192 Uiso 1 1 calc R . . C024 C 0.2092(7) -0.1992(4) 1.1121(4) 0.183(3) Uani 1 1 d . . . H02M H 0.1585 -0.1628 1.1495 0.275 Uiso 1 1 calc R . . H02N H 0.2853 -0.2246 1.1528 0.275 Uiso 1 1 calc R . . H02O H 0.1499 -0.2437 1.0825 0.275 Uiso 1 1 calc R . . C025 C 0.3781(6) -0.0507(5) 1.0855(5) 0.210(3) Uani 1 1 d . . . H02P H 0.4153 -0.0140 1.0409 0.315 Uiso 1 1 calc R . . H02Q H 0.4520 -0.0766 1.1280 0.315 Uiso 1 1 calc R . . H02R H 0.3217 -0.0174 1.1220 0.315 Uiso 1 1 calc R . . N100 N 0.3730(3) -0.0938(2) 0.6894(2) 0.1059(10) Uani 1 1 d . . . C100 C 0.3248(3) -0.03909(19) 0.7274(2) 0.0740(8) 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 Si01 0.0858(6) 0.0843(5) 0.0640(6) 0.0123(4) 0.0034(5) 0.0284(4) O002 0.0681(11) 0.0692(10) 0.0533(11) 0.0112(7) 0.0101(9) 0.0113(8) O004 0.0543(10) 0.0782(10) 0.0636(12) 0.0037(8) 0.0097(9) 0.0093(8) O005 0.0771(13) 0.162(2) 0.0600(13) -0.0163(13) 0.0091(11) 0.0418(14) O003 0.0960(17) 0.0627(12) 0.212(3) -0.0143(14) 0.0426(19) -0.0027(11) C007 0.0550(13) 0.0612(12) 0.0486(14) 0.0076(10) -0.0005(11) 0.0032(10) C008 0.0793(18) 0.0617(14) 0.0649(17) -0.0001(12) 0.0094(14) 0.0028(12) C010 0.0561(13) 0.0551(11) 0.0530(15) 0.0020(10) 0.0077(11) 0.0048(9) C011 0.0545(13) 0.0584(12) 0.0601(15) -0.0066(10) 0.0109(12) 0.0059(10) C012 0.0685(17) 0.0734(16) 0.091(2) -0.0124(15) 0.0170(16) -0.0097(14) C013 0.0667(17) 0.0842(17) 0.0608(18) 0.0087(13) 0.0022(14) 0.0093(13) C014 0.0586(14) 0.0666(14) 0.0610(16) 0.0131(11) 0.0048(13) 0.0024(11) C015 0.0541(15) 0.0793(16) 0.0589(17) -0.0092(12) 0.0039(13) 0.0059(11) C016 0.112(2) 0.0565(14) 0.093(2) -0.0002(14) 0.014(2) 0.0009(15) C017 0.084(2) 0.099(2) 0.124(3) -0.007(2) 0.035(2) -0.0203(18) C018 0.103(2) 0.0674(17) 0.097(2) 0.0202(16) 0.007(2) -0.0147(16) C019 0.0802(19) 0.0789(18) 0.082(2) 0.0207(15) 0.0146(17) -0.0036(15) C020 0.101(3) 0.106(2) 0.102(3) 0.016(2) 0.028(2) -0.009(2) C021 0.100(3) 0.115(3) 0.085(2) -0.0118(19) -0.018(2) 0.000(2) C022 0.076(2) 0.120(3) 0.107(3) 0.024(2) 0.010(2) 0.0298(19) C023 0.136(3) 0.156(4) 0.089(3) -0.003(2) 0.009(2) 0.087(3) C024 0.219(6) 0.186(5) 0.159(5) 0.107(4) 0.078(5) 0.106(5) C025 0.136(4) 0.225(6) 0.234(7) -0.096(6) -0.087(5) 0.051(4) N100 0.108(2) 0.101(2) 0.121(2) 0.0068(17) 0.057(2) 0.0161(17) C100 0.0706(17) 0.0809(18) 0.0736(19) 0.0155(14) 0.0207(16) 0.0042(14) _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 Si01 O002 1.6386(18) . ? Si01 C024 1.819(5) . ? Si01 C023 1.822(3) . ? Si01 C025 1.836(6) . ? O002 C010 1.417(3) . ? O004 C015 1.328(3) . ? O004 C013 1.485(3) . ? O005 C015 1.195(3) . ? O003 C012 1.198(3) . ? C007 C008 1.383(3) . ? C007 C014 1.400(3) . ? C007 C010 1.515(3) . ? C008 C016 1.383(4) . ? C010 C011 1.522(3) . ? C011 C015 1.515(4) . ? C011 C012 1.531(4) . ? C012 C017 1.490(4) . ? C013 C020 1.512(4) . ? C013 C021 1.514(5) . ? C013 C022 1.516(4) . ? C014 C019 1.397(4) . ? C014 C100 1.439(4) . ? C016 C018 1.386(5) . ? C018 C019 1.358(5) . ? N100 C100 1.143(4) . ? 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 O002 Si01 C024 107.1(2) . . ? O002 Si01 C023 112.91(14) . . ? C024 Si01 C023 113.6(2) . . ? O002 Si01 C025 106.7(2) . . ? C024 Si01 C025 104.8(4) . . ? C023 Si01 C025 111.2(3) . . ? C010 O002 Si01 126.45(14) . . ? C015 O004 C013 121.1(2) . . ? C008 C007 C014 118.0(2) . . ? C008 C007 C010 120.0(2) . . ? C014 C007 C010 122.0(2) . . ? C007 C008 C016 120.7(3) . . ? O002 C010 C007 110.80(19) . . ? O002 C010 C011 107.16(18) . . ? C007 C010 C011 110.84(19) . . ? C015 C011 C010 110.53(19) . . ? C015 C011 C012 107.0(2) . . ? C010 C011 C012 111.7(2) . . ? O003 C012 C017 122.5(3) . . ? O003 C012 C011 121.0(2) . . ? C017 C012 C011 116.4(3) . . ? O004 C013 C020 108.9(2) . . ? O004 C013 C021 110.4(2) . . ? C020 C013 C021 113.3(3) . . ? O004 C013 C022 102.0(2) . . ? C020 C013 C022 111.6(3) . . ? C021 C013 C022 110.0(3) . . ? C019 C014 C007 120.9(2) . . ? C019 C014 C100 117.7(2) . . ? C007 C014 C100 121.3(2) . . ? O005 C015 O004 125.7(3) . . ? O005 C015 C011 122.8(2) . . ? O004 C015 C011 111.5(2) . . ? C008 C016 C018 120.5(3) . . ? C019 C018 C016 120.0(3) . . ? C018 C019 C014 119.9(3) . . ? N100 C100 C014 177.5(3) . . ? _diffrn_measured_fraction_theta_max 0.859 _diffrn_reflns_theta_full 30.38 _diffrn_measured_fraction_theta_full 0.859 _refine_diff_density_max 0.403 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.039 # Attachment '- compound 6.cif' data_va122lastlast _database_code_depnum_ccdc_archive 'CCDC 837215' #TrackingRef '- compound 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7.50 H8.50 O2' _chemical_formula_weight 130.64 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.155(5) _cell_length_b 9.280(5) _cell_length_c 14.021(5) _cell_angle_alpha 80.620(5) _cell_angle_beta 86.561(5) _cell_angle_gamma 70.941(5) _cell_volume 746.8(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 139 _exptl_absorpt_coefficient_mu 0.042 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _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 6039 _diffrn_reflns_av_R_equivalents 0.1379 _diffrn_reflns_av_sigmaI/netI 0.3394 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.35 _diffrn_reflns_theta_max 29.78 _reflns_number_total 3684 _reflns_number_gt 856 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0721P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3684 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3505 _refine_ls_R_factor_gt 0.1109 _refine_ls_wR_factor_ref 0.3031 _refine_ls_wR_factor_gt 0.1906 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.918 _refine_ls_shift/su_max 0.014 _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 O001 O 1.0591(7) 0.1673(5) 0.8209(3) 0.0631(13) Uani 1 1 d . . . O002 O 0.6987(6) 0.1996(4) 0.7783(3) 0.0540(12) Uani 1 1 d . . . O100 O 1.0934(7) 0.4109(5) 0.9037(3) 0.0655(13) Uani 1 1 d . . . H100 H 1.1018 0.3741 0.9612 0.098 Uiso 1 1 calc R . . C004 C 0.7777(11) 0.2587(7) 0.9988(5) 0.0564(17) Uani 1 1 d . . . H004 H 0.9411 0.2010 1.0095 0.068 Uiso 1 1 calc R . . O101 O 0.7061(7) 0.3603(5) 1.0669(3) 0.0660(14) Uani 1 1 d . . . H101 H 0.7777 0.4220 1.0583 0.099 Uiso 1 1 calc R . . C006 C 0.7497(10) 0.3396(6) 0.8957(4) 0.0457(15) Uani 1 1 d . . . H006 H 0.5849 0.3842 0.8821 0.055 Uiso 1 1 calc R . . C007 C 0.7633(11) 0.0949(8) 0.7057(5) 0.0599(18) Uani 1 1 d . . . C008 C 1.0241(12) 0.5244(7) 0.7100(5) 0.0638(19) Uani 1 1 d . . . H008 H 1.1703 0.4730 0.7352 0.077 Uiso 1 1 calc R . . C009 C 0.8560(10) 0.4694(7) 0.8747(5) 0.0552(17) Uani 1 1 d . . . H009 H 0.7733 0.5506 0.9128 0.066 Uiso 1 1 calc R . . C010 C 0.8531(12) 0.2279(7) 0.8288(5) 0.0556(18) Uani 1 1 d . . . C011 C 0.8384(12) 0.5377(7) 0.7702(5) 0.0491(16) Uani 1 1 d . . . C012 C 1.0032(15) 0.5829(9) 0.6156(6) 0.078(2) Uani 1 1 d . . . H012 H 1.1323 0.5692 0.5757 0.094 Uiso 1 1 calc R . . C013 C 0.6456(11) 0.1457(8) 1.0184(5) 0.079(2) Uani 1 1 d . . . H01A H 0.6709 0.0939 1.0838 0.118 Uiso 1 1 calc R . . H01B H 0.6970 0.0713 0.9748 0.118 Uiso 1 1 calc R . . H01C H 0.4845 0.2000 1.0089 0.118 Uiso 1 1 calc R . . C101 C 0.5998(15) 0.6806(8) 0.6369(6) 0.081(2) Uani 1 1 d . . . H101 H 0.4546 0.7341 0.6113 0.097 Uiso 1 1 calc R . . C102 C 0.6225(12) 0.6196(7) 0.7332(5) 0.0610(19) Uani 1 1 d . . . H102 H 0.4935 0.6333 0.7732 0.073 Uiso 1 1 calc R . . C100 C 0.7877(18) 0.6634(9) 0.5790(6) 0.090(3) Uani 1 1 d . . . H100 H 0.7710 0.7064 0.5141 0.109 Uiso 1 1 calc R . . C103 C 0.8900(13) 0.1572(10) 0.6245(5) 0.101(3) Uani 1 1 d . . . H10A H 0.7972 0.2592 0.5975 0.151 Uiso 1 1 calc R . . H10B H 0.9236 0.0915 0.5756 0.151 Uiso 1 1 calc R . . H10C H 1.0310 0.1610 0.6480 0.151 Uiso 1 1 calc R . . C104 C 0.8946(14) -0.0632(9) 0.7520(6) 0.103(3) Uani 1 1 d . . . H10D H 0.8044 -0.0975 0.8034 0.155 Uiso 1 1 calc R . . H10E H 1.0353 -0.0624 0.7777 0.155 Uiso 1 1 calc R . . H10F H 0.9290 -0.1320 0.7048 0.155 Uiso 1 1 calc R . . C105 C 0.5305(11) 0.1005(9) 0.6725(6) 0.096(3) Uani 1 1 d . . . H10G H 0.4514 0.0597 0.7257 0.143 Uiso 1 1 calc R . . H10H H 0.5509 0.0400 0.6213 0.143 Uiso 1 1 calc R . . H10I H 0.4418 0.2054 0.6495 0.143 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 O001 0.047(3) 0.057(3) 0.086(4) -0.025(2) -0.004(2) -0.011(2) O002 0.052(3) 0.051(3) 0.062(3) -0.019(2) 0.000(2) -0.016(2) O100 0.067(3) 0.074(3) 0.061(3) 0.001(2) -0.014(2) -0.033(3) C004 0.065(4) 0.056(4) 0.042(4) 0.007(4) -0.013(3) -0.016(4) O101 0.068(3) 0.064(3) 0.075(3) -0.022(3) 0.007(2) -0.028(3) C006 0.045(4) 0.031(3) 0.061(5) -0.017(3) -0.002(3) -0.007(3) C007 0.061(5) 0.058(5) 0.067(5) -0.023(4) -0.002(4) -0.021(4) C008 0.073(5) 0.060(5) 0.061(5) -0.012(4) 0.002(4) -0.023(4) C009 0.048(4) 0.046(4) 0.075(5) -0.013(4) -0.005(3) -0.018(3) C010 0.057(4) 0.049(4) 0.068(5) -0.005(4) -0.007(4) -0.027(4) C011 0.067(4) 0.043(4) 0.040(4) -0.007(3) 0.000(4) -0.021(3) C012 0.105(7) 0.081(6) 0.052(6) -0.004(4) 0.012(5) -0.040(5) C013 0.089(5) 0.061(5) 0.093(6) 0.001(4) 0.000(4) -0.041(4) C101 0.116(7) 0.074(5) 0.055(6) 0.013(4) -0.023(5) -0.042(5) C102 0.076(5) 0.053(4) 0.053(5) 0.009(4) -0.014(4) -0.026(4) C100 0.132(8) 0.084(7) 0.059(6) 0.003(5) 0.000(6) -0.046(6) C103 0.120(7) 0.139(8) 0.069(6) -0.029(5) 0.012(5) -0.073(6) C104 0.120(7) 0.062(6) 0.136(8) -0.036(5) -0.025(6) -0.026(5) C105 0.063(5) 0.126(7) 0.118(7) -0.059(6) -0.002(5) -0.037(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 O001 C010 1.214(7) . ? O002 C010 1.333(7) . ? O002 C007 1.469(7) . ? O100 C009 1.441(6) . ? C004 O101 1.402(7) . ? C004 C013 1.508(7) . ? C004 C006 1.508(7) . ? C006 C010 1.475(8) . ? C006 C009 1.531(7) . ? C007 C103 1.487(8) . ? C007 C104 1.485(9) . ? C007 C105 1.515(8) . ? C008 C012 1.343(8) . ? C008 C011 1.364(7) . ? C009 C011 1.493(8) . ? C011 C102 1.381(8) . ? C012 C100 1.375(10) . ? C101 C100 1.353(9) . ? C101 C102 1.373(8) . ? 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 C010 O002 C007 122.8(5) . . ? O101 C004 C013 107.7(5) . . ? O101 C004 C006 113.2(5) . . ? C013 C004 C006 111.5(5) . . ? C010 C006 C004 110.2(5) . . ? C010 C006 C009 108.3(5) . . ? C004 C006 C009 113.9(5) . . ? O002 C007 C103 109.9(6) . . ? O002 C007 C104 110.0(6) . . ? C103 C007 C104 113.2(7) . . ? O002 C007 C105 101.8(5) . . ? C103 C007 C105 110.6(6) . . ? C104 C007 C105 110.8(6) . . ? C012 C008 C011 122.3(7) . . ? O100 C009 C011 110.0(5) . . ? O100 C009 C006 109.5(5) . . ? C011 C009 C006 111.6(5) . . ? O001 C010 O002 123.4(6) . . ? O001 C010 C006 123.0(6) . . ? O002 C010 C006 113.5(6) . . ? C008 C011 C102 118.5(7) . . ? C008 C011 C009 123.5(7) . . ? C102 C011 C009 118.0(6) . . ? C008 C012 C100 118.9(8) . . ? C100 C101 C102 120.3(8) . . ? C101 C102 C011 119.5(7) . . ? C101 C100 C012 120.4(8) . . ? _diffrn_measured_fraction_theta_max 0.863 _diffrn_reflns_theta_full 29.78 _diffrn_measured_fraction_theta_full 0.863 _refine_diff_density_max 0.262 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.051