# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Doyle, Michael' 'Jaber, Deana' 'Burgin, Ryan' 'Helper, Matthew' 'Zavalij, Peter' _publ_contact_author_name 'Doyle, Michael' _publ_contact_author_email mdoyle3@umd.edu _publ_section_title ; Control of Selectivity in the Generation and Reactions of Oxonium Ylides ; # Attachment '- anti-8a.cif' data_1972 _database_code_depnum_ccdc_archive 'CCDC 826314' #TrackingRef '- anti-8a.cif' _audit_creation_method 'SHELXL-97 & ZCIF' _chemical_name_systematic ; Phenyl-Mirror ; _chemical_name_common Phenyl-Mirror _chemical_formula_moiety 'C16 H16 O5' _chemical_formula_sum 'C16 H16 O5' _chemical_formula_weight 288.29 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 Orthorhombic _symmetry_space_group_name_H-M P212121 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 8.4520(9) _cell_length_b 9.9029(11) _cell_length_c 16.5155(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1382.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12995 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 32.2 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.365 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.886 _exptl_absorpt_correction_T_max 0.963 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'three-circle diffractometer' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 11.198 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17271 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0147 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4018 _reflns_number_gt 3955 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker, 2005)' _computing_cell_refinement Apex2 _computing_data_reduction Apex2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker, 2004)' _computing_publication_material SHELXL-97 _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 'w=1/[\s^2^(Fo^2^)+(0.03P)^2^+0.3615P], P=(max(Fo^2^,0)+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details '(Flack, 1983)' _refine_ls_abs_structure_Flack -0.1(5) _refine_ls_number_reflns 4018 # 2300 w/o Fiedel pairs _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0287 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0671 _refine_ls_wR_factor_gt 0.0669 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.63633(13) 0.34498(11) 0.12104(6) 0.02255(19) Uani 1 1 d . . . H1 H 0.6588(18) 0.3682(15) 0.0667(9) 0.027(4) Uiso 1 1 d . . . C2 C 0.50744(13) 0.40226(11) 0.16110(7) 0.0265(2) Uani 1 1 d . . . H2 H 0.4400(18) 0.4682(15) 0.1337(9) 0.031(4) Uiso 1 1 d . . . C3 C 0.47345(13) 0.36522(11) 0.24027(7) 0.0253(2) Uani 1 1 d . . . H3 H 0.3851(18) 0.4029(15) 0.2652(9) 0.029(3) Uiso 1 1 d . . . C4 C 0.56858(12) 0.27075(11) 0.27916(7) 0.02292(19) Uani 1 1 d . . . H4 H 0.5471(17) 0.2455(15) 0.3343(9) 0.030(4) Uiso 1 1 d . . . C5 C 0.69707(12) 0.21306(10) 0.23912(6) 0.01947(18) Uani 1 1 d . . . H5 H 0.7570(17) 0.1476(14) 0.2639(8) 0.021(3) Uiso 1 1 d . . . C6 C 0.73282(11) 0.24987(10) 0.15942(6) 0.01721(16) Uani 1 1 d . . . C7 C 0.86764(11) 0.18466(9) 0.11182(6) 0.01645(16) Uani 1 1 d . . . H7 H 0.8560(15) 0.2051(13) 0.0562(7) 0.015(3) Uiso 1 1 d . . . C8 C 0.86164(11) 0.02867(9) 0.12065(6) 0.01841(17) Uani 1 1 d . . . H8A H 0.8851(16) 0.0003(14) 0.1741(8) 0.021(2) Uiso 1 1 d . . . H8B H 0.7556(17) 0.0034(14) 0.1080(8) 0.021(2) Uiso 1 1 d . . . C9 C 0.96906(12) -0.04768(9) 0.06277(6) 0.01963(17) Uani 1 1 d . . . O9 O 0.91467(10) -0.10121(9) 0.00272(5) 0.03078(18) Uani 1 1 d . . . C10 C 1.14397(12) -0.06139(10) 0.08107(6) 0.02168(18) Uani 1 1 d . . . H10A H 1.1910(18) -0.0848(16) 0.0318(9) 0.034(3) Uiso 1 1 d . . . H10B H 1.1598(19) -0.1351(16) 0.1159(10) 0.034(3) Uiso 1 1 d . . . C11 C 1.22046(11) 0.06390(10) 0.11875(6) 0.01985(17) Uani 1 1 d . . . H11 H 1.3320(17) 0.0626(15) 0.1039(8) 0.022(3) Uiso 1 1 d . . . O11 O 1.15204(8) 0.18456(7) 0.08136(4) 0.01903(14) Uani 1 1 d . . . C12 C 1.19917(13) 0.08142(11) 0.20999(6) 0.02264(19) Uani 1 1 d . . . H12A H 1.1550(19) 0.0071(16) 0.2369(9) 0.034(3) Uiso 1 1 d . . . H12B H 1.3027(18) 0.1031(16) 0.2358(9) 0.034(3) Uiso 1 1 d . . . C13 C 1.08724(11) 0.19942(10) 0.21929(6) 0.01819(17) Uani 1 1 d . . . O13 O 1.04734(9) 0.25237(8) 0.28150(4) 0.02343(15) Uani 1 1 d . . . C14 C 1.03392(11) 0.24102(9) 0.13351(5) 0.01601(16) Uani 1 1 d . . . C15 C 1.04838(11) 0.39433(9) 0.12199(6) 0.01749(17) Uani 1 1 d . . . O15 O 1.10301(11) 0.46903(8) 0.17182(5) 0.02799(17) Uani 1 1 d . . . O16 O 0.99901(9) 0.43324(7) 0.04917(4) 0.02421(15) Uani 1 1 d . . . C16 C 1.01805(13) 0.57755(11) 0.03409(7) 0.0249(2) Uani 1 1 d . . . H16A H 0.9537(18) 0.6268(15) 0.0727(9) 0.030(2) Uiso 1 1 d . . . H16B H 0.9819(18) 0.5928(15) -0.0202(9) 0.030(2) Uiso 1 1 d . . . H16C H 1.1252(19) 0.5994(16) 0.0386(9) 0.030(2) 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 0.0231(5) 0.0239(4) 0.0206(4) 0.0011(4) -0.0017(4) 0.0030(4) C2 0.0226(5) 0.0254(5) 0.0316(5) 0.0006(4) -0.0027(4) 0.0071(4) C3 0.0190(5) 0.0251(5) 0.0317(5) -0.0046(4) 0.0038(4) 0.0032(4) C4 0.0216(5) 0.0232(5) 0.0239(5) -0.0008(4) 0.0049(4) -0.0008(4) C5 0.0193(4) 0.0183(4) 0.0208(4) 0.0015(3) 0.0013(3) 0.0010(3) C6 0.0166(4) 0.0158(4) 0.0192(4) -0.0021(3) -0.0001(3) -0.0006(3) C7 0.0170(4) 0.0156(4) 0.0168(4) -0.0004(3) 0.0002(3) 0.0000(3) C8 0.0182(4) 0.0153(4) 0.0217(4) -0.0017(3) 0.0019(3) -0.0019(3) C9 0.0230(4) 0.0143(4) 0.0216(4) -0.0001(3) 0.0025(3) -0.0011(3) O9 0.0309(4) 0.0323(4) 0.0291(4) -0.0116(3) -0.0025(3) 0.0008(3) C10 0.0217(4) 0.0185(4) 0.0249(4) -0.0035(4) 0.0021(4) 0.0022(4) C11 0.0173(4) 0.0188(4) 0.0235(4) -0.0017(4) 0.0014(3) 0.0021(3) O11 0.0194(3) 0.0179(3) 0.0198(3) 0.0000(3) 0.0045(3) 0.0018(3) C12 0.0231(5) 0.0225(5) 0.0223(4) -0.0005(4) -0.0037(4) 0.0040(4) C13 0.0176(4) 0.0177(4) 0.0193(4) 0.0005(3) -0.0009(3) -0.0026(3) O13 0.0277(4) 0.0237(3) 0.0188(3) -0.0020(3) 0.0013(3) -0.0021(3) C14 0.0174(4) 0.0149(4) 0.0157(4) -0.0014(3) 0.0012(3) 0.0002(3) C15 0.0155(4) 0.0167(4) 0.0203(4) -0.0004(3) 0.0020(3) 0.0007(3) O15 0.0392(4) 0.0189(3) 0.0259(4) -0.0018(3) -0.0074(3) -0.0045(3) O16 0.0335(4) 0.0175(3) 0.0217(3) 0.0023(3) -0.0050(3) -0.0054(3) C16 0.0279(5) 0.0174(4) 0.0294(5) 0.0046(4) -0.0034(4) -0.0037(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 C1 C2 1.3951(15) . ? C1 C6 1.3979(14) . ? C1 H1 0.945(14) . ? C2 C3 1.3880(16) . ? C2 H2 0.978(15) . ? C3 C4 1.3907(15) . ? C3 H3 0.931(15) . ? C4 C5 1.3940(14) . ? C4 H4 0.962(15) . ? C5 C6 1.3988(13) . ? C5 H5 0.919(14) . ? C6 C7 1.5276(13) . ? C7 C8 1.5525(13) . ? C7 C14 1.5540(13) . ? C7 H7 0.946(12) . ? C8 C9 1.5198(13) . ? C8 H8A 0.948(14) . ? C8 H8B 0.954(14) . ? C9 O9 1.2147(13) . ? C9 C10 1.5151(15) . ? C10 C11 1.5313(14) . ? C10 H10A 0.934(15) . ? C10 H10B 0.939(16) . ? C11 O11 1.4641(12) . ? C11 C12 1.5275(14) . ? C11 H11 0.974(14) . ? O11 C14 1.4321(11) . ? C12 C13 1.5114(14) . ? C12 H12A 0.937(16) . ? C12 H12B 0.997(16) . ? C13 O13 1.2018(12) . ? C13 C14 1.5427(13) . ? C14 C15 1.5349(13) . ? C15 O15 1.1991(12) . ? C15 O16 1.3300(12) . ? O16 C16 1.4596(12) . ? C16 H16A 0.969(15) . ? C16 H16B 0.959(15) . ? C16 H16C 0.934(16) . ? 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 C2 C1 C6 120.96(10) . . ? C2 C1 H1 120.5(9) . . ? C6 C1 H1 118.5(9) . . ? C3 C2 C1 120.06(10) . . ? C3 C2 H2 119.5(9) . . ? C1 C2 H2 120.5(9) . . ? C2 C3 C4 119.55(10) . . ? C2 C3 H3 118.5(9) . . ? C4 C3 H3 121.9(9) . . ? C3 C4 C5 120.46(10) . . ? C3 C4 H4 120.2(9) . . ? C5 C4 H4 119.3(9) . . ? C4 C5 C6 120.52(9) . . ? C4 C5 H5 120.5(9) . . ? C6 C5 H5 118.9(9) . . ? C1 C6 C5 118.44(9) . . ? C1 C6 C7 119.12(9) . . ? C5 C6 C7 122.36(9) . . ? C6 C7 C8 110.36(8) . . ? C6 C7 C14 113.84(7) . . ? C8 C7 C14 111.42(7) . . ? C6 C7 H7 109.3(8) . . ? C8 C7 H7 107.5(8) . . ? C14 C7 H7 104.0(8) . . ? C9 C8 C7 114.61(8) . . ? C9 C8 H8A 108.3(8) . . ? C7 C8 H8A 112.1(8) . . ? C9 C8 H8B 107.1(8) . . ? C7 C8 H8B 105.7(9) . . ? H8A C8 H8B 108.8(12) . . ? O9 C9 C10 119.54(9) . . ? O9 C9 C8 120.30(10) . . ? C10 C9 C8 120.13(8) . . ? C9 C10 C11 114.86(8) . . ? C9 C10 H10A 105.3(9) . . ? C11 C10 H10A 112.0(10) . . ? C9 C10 H10B 109.3(10) . . ? C11 C10 H10B 108.7(10) . . ? H10A C10 H10B 106.3(14) . . ? O11 C11 C12 106.07(8) . . ? O11 C11 C10 108.85(8) . . ? C12 C11 C10 116.31(9) . . ? O11 C11 H11 106.6(8) . . ? C12 C11 H11 111.4(8) . . ? C10 C11 H11 107.2(8) . . ? C14 O11 C11 109.90(7) . . ? C13 C12 C11 105.18(8) . . ? C13 C12 H12A 108.0(10) . . ? C11 C12 H12A 115.1(9) . . ? C13 C12 H12B 109.8(9) . . ? C11 C12 H12B 110.0(9) . . ? H12A C12 H12B 108.5(13) . . ? O13 C13 C12 126.86(9) . . ? O13 C13 C14 125.92(9) . . ? C12 C13 C14 107.22(8) . . ? O11 C14 C15 104.84(7) . . ? O11 C14 C13 104.14(7) . . ? C15 C14 C13 110.77(7) . . ? O11 C14 C7 110.59(7) . . ? C15 C14 C7 113.50(8) . . ? C13 C14 C7 112.33(7) . . ? O15 C15 O16 124.24(9) . . ? O15 C15 C14 123.77(9) . . ? O16 C15 C14 111.94(8) . . ? C15 O16 C16 113.79(8) . . ? O16 C16 H16A 108.6(9) . . ? O16 C16 H16B 106.2(9) . . ? H16A C16 H16B 110.9(13) . . ? O16 C16 H16C 108.7(10) . . ? H16A C16 H16C 112.0(13) . . ? H16B C16 H16C 110.3(13) . . ? 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 C6 C1 C2 C3 0.09(17) . . . . ? C1 C2 C3 C4 -0.05(17) . . . . ? C2 C3 C4 C5 -0.18(16) . . . . ? C3 C4 C5 C6 0.38(16) . . . . ? C2 C1 C6 C5 0.11(15) . . . . ? C2 C1 C6 C7 176.98(9) . . . . ? C4 C5 C6 C1 -0.34(15) . . . . ? C4 C5 C6 C7 -177.11(9) . . . . ? C1 C6 C7 C8 -129.84(9) . . . . ? C5 C6 C7 C8 46.91(12) . . . . ? C1 C6 C7 C14 104.01(10) . . . . ? C5 C6 C7 C14 -79.24(11) . . . . ? C6 C7 C8 C9 168.33(8) . . . . ? C14 C7 C8 C9 -64.18(10) . . . . ? C7 C8 C9 O9 -101.74(11) . . . . ? C7 C8 C9 C10 80.26(11) . . . . ? O9 C9 C10 C11 143.90(10) . . . . ? C8 C9 C10 C11 -38.08(13) . . . . ? C9 C10 C11 O11 -37.79(11) . . . . ? C9 C10 C11 C12 81.89(11) . . . . ? C12 C11 O11 C14 -25.74(10) . . . . ? C10 C11 O11 C14 100.12(9) . . . . ? O11 C11 C12 C13 11.76(10) . . . . ? C10 C11 C12 C13 -109.41(10) . . . . ? C11 C12 C13 O13 -174.76(10) . . . . ? C11 C12 C13 C14 4.74(10) . . . . ? C11 O11 C14 C15 144.60(7) . . . . ? C11 O11 C14 C13 28.17(9) . . . . ? C11 O11 C14 C7 -92.71(9) . . . . ? O13 C13 C14 O11 159.74(9) . . . . ? C12 C13 C14 O11 -19.77(10) . . . . ? O13 C13 C14 C15 47.52(12) . . . . ? C12 C13 C14 C15 -131.98(8) . . . . ? O13 C13 C14 C7 -80.56(12) . . . . ? C12 C13 C14 C7 99.94(9) . . . . ? C6 C7 C14 O11 -174.56(7) . . . . ? C8 C7 C14 O11 59.86(10) . . . . ? C6 C7 C14 C15 -57.07(10) . . . . ? C8 C7 C14 C15 177.35(8) . . . . ? C6 C7 C14 C13 69.56(10) . . . . ? C8 C7 C14 C13 -56.02(10) . . . . ? O11 C14 C15 O15 -107.58(10) . . . . ? C13 C14 C15 O15 4.18(13) . . . . ? C7 C14 C15 O15 131.63(10) . . . . ? O11 C14 C15 O16 69.94(10) . . . . ? C13 C14 C15 O16 -178.30(8) . . . . ? C7 C14 C15 O16 -50.85(10) . . . . ? O15 C15 O16 C16 0.41(14) . . . . ? C14 C15 O16 C16 -177.09(8) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.279 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.036 _chemical_absolute_configuration un _diffrn_orient_matrix_type standard _diffrn_orient_matrix_UB_11 0.0278152 _diffrn_orient_matrix_UB_12 -0.0855284 _diffrn_orient_matrix_UB_13 -0.0289054 _diffrn_orient_matrix_UB_21 -0.1148151 _diffrn_orient_matrix_UB_22 -0.0235366 _diffrn_orient_matrix_UB_23 -0.0039512 _diffrn_orient_matrix_UB_31 -0.0065540 _diffrn_orient_matrix_UB_32 0.0482483 _diffrn_orient_matrix_UB_33 -0.0530565 _symmetry_space_group_name_Hall 'P 2ac 2ab' _exptl_crystal_id 'Doyle/Jaber Phenyl-Mirror product 150K' _diffrn_measurement_frame_width-CCD -0.30 _diffrn_measurement_details 610,610,610,210 _diffrn_measurement_total_frames-CCD 2040 _diffrn_measurement_frame_time-CCD 5 _diffrn_measurement_total_time-CCD 6.3 _diffrn_source_voltage 50.00 _diffrn_source_current 30.00 _diffrn_detector_distance-CCD 5.000 _diffrn_measurement_frame_size-CCD 512 _diffrn_measurement_specimen_support 'MiTeGen grip' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker Smart Apex II' _reflns_Friedel_coverage 1.00 #_______________________________________________________________________________ # _publ_section_references ; Bruker (2005). Apex2. Bruker AXS Inc., Madison, Wisconsin, USA. Flack, H.D. (1983), Acta Cryst. A39, 876-881. Sheldrick, G. M. (1990). Acta Cryst. A46, 467-473. Sheldrick, G. M. (1996). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (1997). SHELXL-97. University of G\"ottingen, Germany. Spek, A. L. (1990). Acta Cryst., A46, C-34. ; # Attachment '- syn-8a.cif' data_1906 _database_code_depnum_ccdc_archive 'CCDC 826315' #TrackingRef '- syn-8a.cif' _audit_creation_method 'SHELXL-97 & ZCIF' _chemical_name_systematic ; Diazo Decomp-Major product ; _chemical_name_common 'Diazo Decomp-Major product' _chemical_formula_moiety 'C16 H16 O5' _chemical_formula_sum 'C16 H16 O5' _chemical_formula_weight 288.29 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3115(11) _cell_length_b 11.0094(12) _cell_length_c 13.2743(14) _cell_angle_alpha 89.6028(14) _cell_angle_beta 67.7337(13) _cell_angle_gamma 80.3302(14) _cell_volume 1372.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8296 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 28.3 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.095 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.945 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _diffrn_ambient_temperature 120(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 'three-circle diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.667 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6300 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6300 _reflns_number_gt 5367 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker, 2005)' _computing_cell_refinement Apex2 _computing_data_reduction Apex2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker, 2004)' _computing_publication_material SHELXL-97 _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 'w=1/[\s^2^(Fo^2^)+(0.02P)^2^+0.562P], P=(max(Fo^2^,0)+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6300 _refine_ls_number_parameters 498 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0779 _refine_ls_wR_factor_gt 0.0748 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.000 _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 C1A C 0.22635(16) 0.32619(14) 0.25043(12) 0.0206(3) Uani 1 1 d . . . H1A H 0.2612(19) 0.2561(17) 0.2840(15) 0.026(5) Uiso 1 1 d . . . C2A C 0.10385(16) 0.32845(15) 0.22948(13) 0.0231(3) Uani 1 1 d . . . H2A H 0.0540(19) 0.2605(16) 0.2497(15) 0.027(5) Uiso 1 1 d . . . C3A C 0.05685(16) 0.42586(16) 0.17739(13) 0.0248(3) Uani 1 1 d . . . H3A H -0.027(2) 0.4264(17) 0.1620(15) 0.030(5) Uiso 1 1 d . . . C4A C 0.13135(17) 0.52299(15) 0.14907(13) 0.0256(3) Uani 1 1 d . . . H4A H 0.100(2) 0.5921(18) 0.1124(16) 0.032(5) Uiso 1 1 d . . . C5A C 0.25254(16) 0.52239(14) 0.17139(13) 0.0212(3) Uani 1 1 d . . . H5A H 0.3014(18) 0.5917(16) 0.1536(14) 0.024(4) Uiso 1 1 d . . . C6A C 0.30221(15) 0.42319(13) 0.22102(12) 0.0176(3) Uani 1 1 d . . . C7A C 0.44285(15) 0.41846(13) 0.23378(12) 0.0171(3) Uani 1 1 d . . . H7A H 0.4636(16) 0.5008(15) 0.2304(13) 0.014(4) Uiso 1 1 d . . . C8A C 0.55910(16) 0.33459(15) 0.13711(13) 0.0213(3) Uani 1 1 d . . . H8A H 0.5252(18) 0.2558(16) 0.1366(15) 0.025(3) Uiso 1 1 d . . . H8B H 0.5689(18) 0.3734(16) 0.0710(15) 0.025(3) Uiso 1 1 d . . . C9A C 0.70306(16) 0.30808(15) 0.14566(12) 0.0218(3) Uani 1 1 d . . . O9A O 0.79052(12) 0.37467(12) 0.10687(10) 0.0323(3) Uani 1 1 d . . . C10A C 0.73173(17) 0.19566(15) 0.20587(14) 0.0235(3) Uani 1 1 d . . . H10A H 0.8335(19) 0.1817(16) 0.1959(14) 0.025(3) Uiso 1 1 d . . . H10B H 0.7126(18) 0.1247(17) 0.1729(15) 0.025(3) Uiso 1 1 d . . . C11A C 0.63514(16) 0.21148(14) 0.32752(13) 0.0221(3) Uani 1 1 d . . . H11A H 0.6451(18) 0.1326(16) 0.3624(15) 0.025(4) Uiso 1 1 d . . . O11A O 0.48554(10) 0.24223(9) 0.34222(9) 0.0196(2) Uani 1 1 d . . . C12A C 0.65908(17) 0.31795(15) 0.38644(14) 0.0235(3) Uani 1 1 d . . . H12A H 0.625(2) 0.3082(17) 0.4661(16) 0.032(4) Uiso 1 1 d . . . H12B H 0.757(2) 0.3350(17) 0.3586(15) 0.032(4) Uiso 1 1 d . . . C13A C 0.55991(16) 0.42593(14) 0.37052(12) 0.0190(3) Uani 1 1 d . . . O13A O 0.56593(12) 0.53390(10) 0.37454(9) 0.0239(2) Uani 1 1 d . . . C14A C 0.44513(15) 0.37263(12) 0.34424(12) 0.0172(3) Uani 1 1 d . . . C15A C 0.30217(15) 0.41986(13) 0.43701(12) 0.0186(3) Uani 1 1 d . . . O15A O 0.24458(12) 0.52596(10) 0.44725(9) 0.0255(2) Uani 1 1 d . . . O16A O 0.25329(12) 0.33268(10) 0.50378(9) 0.0235(2) Uani 1 1 d . . . C16A C 0.1223(2) 0.37689(18) 0.59645(16) 0.0351(4) Uani 1 1 d . . . H16A H 0.136(2) 0.440(2) 0.6374(17) 0.040(3) Uiso 1 1 d . . . H16B H 0.099(2) 0.305(2) 0.6394(17) 0.040(3) Uiso 1 1 d . . . H16C H 0.048(2) 0.4117(19) 0.5728(17) 0.040(3) Uiso 1 1 d . . . C1B C 0.75571(16) 0.17931(14) 0.59334(13) 0.0189(3) Uani 1 1 d . . . H1B H 0.7235(18) 0.2463(16) 0.6444(14) 0.021(4) Uiso 1 1 d . . . C2B C 0.87838(16) 0.17725(14) 0.50000(13) 0.0221(3) Uani 1 1 d . . . H2B H 0.9319(19) 0.2444(17) 0.4890(15) 0.029(5) Uiso 1 1 d . . . C3B C 0.92517(16) 0.07956(15) 0.42193(13) 0.0227(3) Uani 1 1 d . . . H3B H 1.0141(19) 0.0769(16) 0.3563(15) 0.025(5) Uiso 1 1 d . . . C4B C 0.84949(17) -0.01639(15) 0.43792(13) 0.0236(3) Uani 1 1 d . . . H4B H 0.8782(19) -0.0849(17) 0.3842(15) 0.027(5) Uiso 1 1 d . . . C5B C 0.72800(16) -0.01621(14) 0.53176(12) 0.0200(3) Uani 1 1 d . . . H5B H 0.6777(19) -0.0857(17) 0.5412(15) 0.029(5) Uiso 1 1 d . . . C6B C 0.67989(15) 0.08222(13) 0.61008(12) 0.0169(3) Uani 1 1 d . . . C7B C 0.54159(15) 0.08455(13) 0.70790(12) 0.0165(3) Uani 1 1 d . . . H7B H 0.5236(17) 0.0018(15) 0.7187(13) 0.016(4) Uiso 1 1 d . . . C8B C 0.41969(16) 0.16512(15) 0.68290(13) 0.0209(3) Uani 1 1 d . . . H8C H 0.4046(19) 0.1212(17) 0.6253(15) 0.028(3) Uiso 1 1 d . . . H8D H 0.4496(19) 0.2411(17) 0.6556(15) 0.028(3) Uiso 1 1 d . . . C9B C 0.28052(16) 0.19378(15) 0.78089(13) 0.0221(3) Uani 1 1 d . . . O9B O 0.19379(12) 0.12532(11) 0.80412(10) 0.0312(3) Uani 1 1 d . . . C10B C 0.25798(17) 0.30945(15) 0.85096(14) 0.0236(3) Uani 1 1 d . . . H10C H 0.2769(19) 0.3763(17) 0.8047(15) 0.025(3) Uiso 1 1 d . . . H10D H 0.1607(19) 0.3261(16) 0.9036(15) 0.025(3) Uiso 1 1 d . . . C11B C 0.35803(15) 0.29395(14) 0.91300(13) 0.0203(3) Uani 1 1 d . . . H11B H 0.3524(18) 0.3729(16) 0.9486(14) 0.022(4) Uiso 1 1 d . . . O11B O 0.50630(10) 0.26108(9) 0.83760(9) 0.0186(2) Uani 1 1 d . . . C12B C 0.33458(17) 0.18785(14) 0.98812(13) 0.0213(3) Uani 1 1 d . . . H12C H 0.2373(19) 0.1752(16) 1.0226(14) 0.023(3) Uiso 1 1 d . . . H12D H 0.3718(18) 0.1969(16) 1.0446(15) 0.023(3) Uiso 1 1 d . . . C13B C 0.42953(14) 0.07910(13) 0.91426(11) 0.0163(3) Uani 1 1 d . . . O13B O 0.42212(11) -0.02891(9) 0.92336(9) 0.0203(2) Uani 1 1 d . . . C14B C 0.54361(14) 0.13076(13) 0.81785(11) 0.0157(3) Uani 1 1 d . . . C15B C 0.68689(14) 0.08060(13) 0.82595(11) 0.0162(3) Uani 1 1 d . . . O15B O 0.74416(11) -0.02539(9) 0.80080(9) 0.0209(2) Uani 1 1 d . . . O16B O 0.73513(11) 0.16505(9) 0.86709(9) 0.0210(2) Uani 1 1 d . . . C16B C 0.86695(17) 0.11881(17) 0.88156(15) 0.0278(4) Uani 1 1 d . . . H16D H 0.941(2) 0.0859(18) 0.8126(18) 0.040(3) Uiso 1 1 d . . . H16E H 0.892(2) 0.1892(19) 0.9091(17) 0.040(3) Uiso 1 1 d . . . H16F H 0.850(2) 0.0550(19) 0.9367(17) 0.040(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 C1A 0.0239(8) 0.0183(7) 0.0202(7) -0.0005(6) -0.0089(6) -0.0041(6) C2A 0.0197(7) 0.0237(8) 0.0242(8) -0.0041(6) -0.0053(6) -0.0064(6) C3A 0.0168(7) 0.0329(9) 0.0227(8) -0.0054(7) -0.0075(6) 0.0007(6) C4A 0.0249(8) 0.0273(8) 0.0234(8) 0.0021(7) -0.0101(6) 0.0008(6) C5A 0.0231(7) 0.0189(7) 0.0210(7) 0.0027(6) -0.0076(6) -0.0038(6) C6A 0.0185(7) 0.0184(7) 0.0154(7) -0.0026(5) -0.0067(6) -0.0015(5) C7A 0.0205(7) 0.0153(7) 0.0173(7) 0.0012(5) -0.0082(6) -0.0056(5) C8A 0.0210(7) 0.0256(8) 0.0187(7) -0.0018(6) -0.0088(6) -0.0046(6) C9A 0.0207(7) 0.0264(8) 0.0169(7) -0.0056(6) -0.0054(6) -0.0046(6) O9A 0.0274(6) 0.0427(7) 0.0315(6) 0.0075(5) -0.0123(5) -0.0162(5) C10A 0.0195(7) 0.0223(8) 0.0283(8) -0.0043(7) -0.0098(6) -0.0010(6) C11A 0.0223(7) 0.0178(7) 0.0276(8) 0.0027(6) -0.0118(6) -0.0018(6) O11A 0.0200(5) 0.0128(5) 0.0254(5) 0.0010(4) -0.0082(4) -0.0020(4) C12A 0.0254(8) 0.0243(8) 0.0245(8) 0.0010(6) -0.0138(7) -0.0037(6) C13A 0.0240(7) 0.0204(7) 0.0142(7) 0.0007(5) -0.0084(6) -0.0057(6) O13A 0.0332(6) 0.0186(5) 0.0244(6) 0.0005(4) -0.0141(5) -0.0091(4) C14A 0.0222(7) 0.0111(6) 0.0195(7) 0.0008(5) -0.0090(6) -0.0037(5) C15A 0.0233(7) 0.0173(7) 0.0168(7) -0.0006(5) -0.0091(6) -0.0047(6) O15A 0.0306(6) 0.0167(5) 0.0252(6) -0.0008(4) -0.0080(5) -0.0001(4) O16A 0.0263(6) 0.0178(5) 0.0201(5) 0.0006(4) -0.0018(4) -0.0039(4) C16A 0.0352(10) 0.0267(9) 0.0283(9) -0.0001(7) 0.0044(8) -0.0049(8) C1B 0.0206(7) 0.0159(7) 0.0200(7) 0.0009(6) -0.0082(6) -0.0013(5) C2B 0.0211(7) 0.0200(7) 0.0256(8) 0.0077(6) -0.0093(6) -0.0042(6) C3B 0.0181(7) 0.0249(8) 0.0201(7) 0.0052(6) -0.0041(6) 0.0016(6) C4B 0.0269(8) 0.0212(8) 0.0192(7) -0.0014(6) -0.0076(6) 0.0021(6) C5B 0.0234(7) 0.0171(7) 0.0201(7) 0.0017(6) -0.0096(6) -0.0026(6) C6B 0.0186(7) 0.0166(7) 0.0157(7) 0.0025(5) -0.0075(5) -0.0017(5) C7B 0.0176(7) 0.0150(7) 0.0170(7) 0.0017(5) -0.0063(6) -0.0043(5) C8B 0.0220(7) 0.0233(8) 0.0192(7) 0.0023(6) -0.0105(6) -0.0030(6) C9B 0.0185(7) 0.0262(8) 0.0240(8) 0.0033(6) -0.0120(6) -0.0011(6) O9B 0.0229(6) 0.0367(7) 0.0369(7) 0.0015(5) -0.0125(5) -0.0104(5) C10B 0.0191(7) 0.0216(8) 0.0269(8) 0.0021(7) -0.0070(6) 0.0001(6) C11B 0.0183(7) 0.0172(7) 0.0224(7) -0.0030(6) -0.0052(6) -0.0016(5) O11B 0.0166(5) 0.0137(5) 0.0236(5) -0.0008(4) -0.0056(4) -0.0021(4) C12B 0.0208(7) 0.0222(8) 0.0183(7) -0.0018(6) -0.0054(6) -0.0015(6) C13B 0.0166(6) 0.0202(7) 0.0148(7) 0.0009(5) -0.0085(5) -0.0044(5) O13B 0.0233(5) 0.0189(5) 0.0204(5) 0.0030(4) -0.0086(4) -0.0075(4) C14B 0.0168(7) 0.0136(6) 0.0167(7) 0.0001(5) -0.0061(5) -0.0031(5) C15B 0.0174(7) 0.0176(7) 0.0127(6) 0.0016(5) -0.0038(5) -0.0051(5) O15B 0.0212(5) 0.0183(5) 0.0212(5) 0.0001(4) -0.0071(4) -0.0002(4) O16B 0.0187(5) 0.0213(5) 0.0253(6) -0.0009(4) -0.0102(4) -0.0053(4) C16B 0.0197(8) 0.0337(9) 0.0329(9) -0.0028(8) -0.0135(7) -0.0045(7) _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 C1A C2A 1.389(2) . ? C1A C6A 1.396(2) . ? C1A H1A 0.973(18) . ? C2A C3A 1.390(2) . ? C2A H2A 0.959(18) . ? C3A C4A 1.388(2) . ? C3A H3A 0.963(19) . ? C4A C5A 1.388(2) . ? C4A H4A 0.977(19) . ? C5A C6A 1.395(2) . ? C5A H5A 0.963(17) . ? C6A C7A 1.515(2) . ? C7A C8A 1.554(2) . ? C7A C14A 1.555(2) . ? C7A H7A 0.962(16) . ? C8A C9A 1.511(2) . ? C8A H8A 0.990(18) . ? C8A H8B 0.951(18) . ? C9A O9A 1.2170(19) . ? C9A C10A 1.517(2) . ? C10A C11A 1.535(2) . ? C10A H10A 0.991(18) . ? C10A H10B 0.981(19) . ? C11A O11A 1.4593(18) . ? C11A C12A 1.517(2) . ? C11A H11A 0.990(18) . ? O11A C14A 1.4235(16) . ? C12A C13A 1.502(2) . ? C12A H12A 0.99(2) . ? C12A H12B 0.982(19) . ? C13A O13A 1.2032(18) . ? C13A C14A 1.554(2) . ? C14A C15A 1.528(2) . ? C15A O15A 1.2015(18) . ? C15A O16A 1.3316(17) . ? O16A C16A 1.450(2) . ? C16A H16A 0.94(2) . ? C16A H16B 0.98(2) . ? C16A H16C 0.96(2) . ? C1B C2B 1.392(2) . ? C1B C6B 1.396(2) . ? C1B H1B 0.931(18) . ? C2B C3B 1.388(2) . ? C2B H2B 0.974(18) . ? C3B C4B 1.385(2) . ? C3B H3B 0.993(18) . ? C4B C5B 1.392(2) . ? C4B H4B 0.969(19) . ? C5B C6B 1.395(2) . ? C5B H5B 0.976(18) . ? C6B C7B 1.5183(19) . ? C7B C8B 1.554(2) . ? C7B C14B 1.558(2) . ? C7B H7B 0.959(16) . ? C8B C9B 1.513(2) . ? C8B H8C 0.98(2) . ? C8B H8D 0.961(19) . ? C9B O9B 1.2155(19) . ? C9B C10B 1.515(2) . ? C10B C11B 1.534(2) . ? C10B H10C 0.953(18) . ? C10B H10D 0.968(18) . ? C11B O11B 1.4594(17) . ? C11B C12B 1.521(2) . ? C11B H11B 0.975(18) . ? O11B C14B 1.4207(16) . ? C12B C13B 1.499(2) . ? C12B H12C 0.966(18) . ? C12B H12D 0.976(19) . ? C13B O13B 1.2067(17) . ? C13B C14B 1.5553(19) . ? C14B C15B 1.5313(19) . ? C15B O15B 1.2026(17) . ? C15B O16B 1.3336(17) . ? O16B C16B 1.4518(19) . ? C16B H16D 0.97(2) . ? C16B H16E 0.97(2) . ? C16B H16F 1.00(2) . ? 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 C2A C1A C6A 120.16(15) . . ? C2A C1A H1A 120.3(11) . . ? C6A C1A H1A 119.5(11) . . ? C1A C2A C3A 120.55(15) . . ? C1A C2A H2A 118.8(11) . . ? C3A C2A H2A 120.7(11) . . ? C4A C3A C2A 119.35(15) . . ? C4A C3A H3A 120.4(11) . . ? C2A C3A H3A 120.3(11) . . ? C3A C4A C5A 120.41(15) . . ? C3A C4A H4A 120.3(11) . . ? C5A C4A H4A 119.3(11) . . ? C4A C5A C6A 120.39(14) . . ? C4A C5A H5A 119.6(10) . . ? C6A C5A H5A 120.0(10) . . ? C5A C6A C1A 119.10(14) . . ? C5A C6A C7A 119.29(13) . . ? C1A C6A C7A 121.44(13) . . ? C6A C7A C8A 107.42(12) . . ? C6A C7A C14A 114.90(12) . . ? C8A C7A C14A 110.42(12) . . ? C6A C7A H7A 108.6(9) . . ? C8A C7A H7A 109.8(10) . . ? C14A C7A H7A 105.7(10) . . ? C9A C8A C7A 113.75(12) . . ? C9A C8A H8A 108.9(10) . . ? C7A C8A H8A 106.8(10) . . ? C9A C8A H8B 108.7(11) . . ? C7A C8A H8B 108.8(11) . . ? H8A C8A H8B 109.8(15) . . ? O9A C9A C8A 121.31(15) . . ? O9A C9A C10A 122.05(15) . . ? C8A C9A C10A 116.63(13) . . ? C9A C10A C11A 111.75(13) . . ? C9A C10A H10A 108.3(10) . . ? C11A C10A H10A 110.8(10) . . ? C9A C10A H10B 107.6(11) . . ? C11A C10A H10B 108.8(11) . . ? H10A C10A H10B 109.5(15) . . ? O11A C11A C12A 104.56(12) . . ? O11A C11A C10A 110.79(13) . . ? C12A C11A C10A 112.79(13) . . ? O11A C11A H11A 105.8(10) . . ? C12A C11A H11A 112.4(11) . . ? C10A C11A H11A 110.1(10) . . ? C14A O11A C11A 109.51(11) . . ? C13A C12A C11A 102.82(12) . . ? C13A C12A H12A 106.2(11) . . ? C11A C12A H12A 111.2(11) . . ? C13A C12A H12B 109.8(11) . . ? C11A C12A H12B 115.7(11) . . ? H12A C12A H12B 110.5(15) . . ? O13A C13A C12A 128.28(14) . . ? O13A C13A C14A 124.80(13) . . ? C12A C13A C14A 106.90(12) . . ? O11A C14A C15A 111.72(11) . . ? O11A C14A C13A 104.75(11) . . ? C15A C14A C13A 106.84(12) . . ? O11A C14A C7A 113.17(12) . . ? C15A C14A C7A 110.41(12) . . ? C13A C14A C7A 109.60(11) . . ? O15A C15A O16A 125.26(14) . . ? O15A C15A C14A 121.76(13) . . ? O16A C15A C14A 112.96(12) . . ? C15A O16A C16A 114.05(12) . . ? O16A C16A H16A 109.8(13) . . ? O16A C16A H16B 106.2(12) . . ? H16A C16A H16B 111.4(18) . . ? O16A C16A H16C 110.8(13) . . ? H16A C16A H16C 107.5(18) . . ? H16B C16A H16C 111.3(17) . . ? C2B C1B C6B 120.33(14) . . ? C2B C1B H1B 119.8(10) . . ? C6B C1B H1B 119.9(10) . . ? C3B C2B C1B 120.29(14) . . ? C3B C2B H2B 119.5(11) . . ? C1B C2B H2B 120.2(11) . . ? C4B C3B C2B 119.49(14) . . ? C4B C3B H3B 120.1(10) . . ? C2B C3B H3B 120.3(10) . . ? C3B C4B C5B 120.69(15) . . ? C3B C4B H4B 121.4(11) . . ? C5B C4B H4B 117.9(11) . . ? C4B C5B C6B 120.05(14) . . ? C4B C5B H5B 118.8(11) . . ? C6B C5B H5B 121.1(11) . . ? C5B C6B C1B 119.15(14) . . ? C5B C6B C7B 119.03(13) . . ? C1B C6B C7B 121.72(13) . . ? C6B C7B C8B 108.16(12) . . ? C6B C7B C14B 114.57(12) . . ? C8B C7B C14B 110.65(12) . . ? C6B C7B H7B 108.7(10) . . ? C8B C7B H7B 109.6(10) . . ? C14B C7B H7B 105.0(10) . . ? C9B C8B C7B 113.56(12) . . ? C9B C8B H8C 109.0(10) . . ? C7B C8B H8C 108.3(11) . . ? C9B C8B H8D 109.3(11) . . ? C7B C8B H8D 108.5(11) . . ? H8C C8B H8D 108.1(15) . . ? O9B C9B C8B 121.69(15) . . ? O9B C9B C10B 121.85(15) . . ? C8B C9B C10B 116.41(13) . . ? C9B C10B C11B 111.02(12) . . ? C9B C10B H10C 108.4(11) . . ? C11B C10B H10C 109.3(11) . . ? C9B C10B H10D 109.4(11) . . ? C11B C10B H10D 108.5(11) . . ? H10C C10B H10D 110.3(15) . . ? O11B C11B C12B 104.49(11) . . ? O11B C11B C10B 110.75(12) . . ? C12B C11B C10B 112.21(13) . . ? O11B C11B H11B 104.7(10) . . ? C12B C11B H11B 114.6(10) . . ? C10B C11B H11B 109.7(10) . . ? C14B O11B C11B 109.46(10) . . ? C13B C12B C11B 102.67(12) . . ? C13B C12B H12C 112.1(11) . . ? C11B C12B H12C 115.7(10) . . ? C13B C12B H12D 106.3(10) . . ? C11B C12B H12D 110.9(10) . . ? H12C C12B H12D 108.6(14) . . ? O13B C13B C12B 128.67(13) . . ? O13B C13B C14B 124.43(13) . . ? C12B C13B C14B 106.89(12) . . ? O11B C14B C15B 111.85(11) . . ? O11B C14B C13B 104.85(11) . . ? C15B C14B C13B 105.96(11) . . ? O11B C14B C7B 113.47(11) . . ? C15B C14B C7B 110.72(11) . . ? C13B C14B C7B 109.53(11) . . ? O15B C15B O16B 125.27(13) . . ? O15B C15B C14B 121.94(13) . . ? O16B C15B C14B 112.74(12) . . ? C15B O16B C16B 114.22(12) . . ? O16B C16B H16D 110.3(12) . . ? O16B C16B H16E 105.9(12) . . ? H16D C16B H16E 110.2(17) . . ? O16B C16B H16F 108.9(12) . . ? H16D C16B H16F 111.5(16) . . ? H16E C16B H16F 109.8(17) . . ? 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 C6A C1A C2A C3A 1.2(2) . . . . ? C1A C2A C3A C4A -1.8(2) . . . . ? C2A C3A C4A C5A 0.7(2) . . . . ? C3A C4A C5A C6A 1.0(2) . . . . ? C4A C5A C6A C1A -1.6(2) . . . . ? C4A C5A C6A C7A 173.67(14) . . . . ? C2A C1A C6A C5A 0.6(2) . . . . ? C2A C1A C6A C7A -174.65(14) . . . . ? C5A C6A C7A C8A -96.87(16) . . . . ? C1A C6A C7A C8A 78.33(17) . . . . ? C5A C6A C7A C14A 139.84(14) . . . . ? C1A C6A C7A C14A -44.95(19) . . . . ? C6A C7A C8A C9A -173.00(13) . . . . ? C14A C7A C8A C9A -47.00(17) . . . . ? C7A C8A C9A O9A -90.04(18) . . . . ? C7A C8A C9A C10A 89.29(17) . . . . ? O9A C9A C10A C11A 113.11(17) . . . . ? C8A C9A C10A C11A -66.22(18) . . . . ? C9A C10A C11A O11A 54.44(17) . . . . ? C9A C10A C11A C12A -62.38(17) . . . . ? C12A C11A O11A C14A 33.33(15) . . . . ? C10A C11A O11A C14A -88.45(14) . . . . ? O11A C11A C12A C13A -32.55(15) . . . . ? C10A C11A C12A C13A 87.91(15) . . . . ? C11A C12A C13A O13A -157.51(16) . . . . ? C11A C12A C13A C14A 21.19(16) . . . . ? C11A O11A C14A C15A -134.58(12) . . . . ? C11A O11A C14A C13A -19.29(14) . . . . ? C11A O11A C14A C7A 100.05(14) . . . . ? O13A C13A C14A O11A 176.63(14) . . . . ? C12A C13A C14A O11A -2.13(15) . . . . ? O13A C13A C14A C15A -64.72(18) . . . . ? C12A C13A C14A C15A 116.52(13) . . . . ? O13A C13A C14A C7A 54.92(19) . . . . ? C12A C13A C14A C7A -123.84(13) . . . . ? C6A C7A C14A O11A 89.18(15) . . . . ? C8A C7A C14A O11A -32.49(16) . . . . ? C6A C7A C14A C15A -36.88(16) . . . . ? C8A C7A C14A C15A -158.55(12) . . . . ? C6A C7A C14A C13A -154.31(12) . . . . ? C8A C7A C14A C13A 84.02(14) . . . . ? O11A C14A C15A O15A -174.18(13) . . . . ? C13A C14A C15A O15A 71.81(17) . . . . ? C7A C14A C15A O15A -47.30(19) . . . . ? O11A C14A C15A O16A 7.28(17) . . . . ? C13A C14A C15A O16A -106.73(13) . . . . ? C7A C14A C15A O16A 134.16(13) . . . . ? O15A C15A O16A C16A -2.2(2) . . . . ? C14A C15A O16A C16A 176.27(14) . . . . ? C6B C1B C2B C3B 1.0(2) . . . . ? C1B C2B C3B C4B -0.5(2) . . . . ? C2B C3B C4B C5B -0.6(2) . . . . ? C3B C4B C5B C6B 1.1(2) . . . . ? C4B C5B C6B C1B -0.5(2) . . . . ? C4B C5B C6B C7B 175.83(13) . . . . ? C2B C1B C6B C5B -0.5(2) . . . . ? C2B C1B C6B C7B -176.75(14) . . . . ? C5B C6B C7B C8B -95.75(15) . . . . ? C1B C6B C7B C8B 80.51(17) . . . . ? C5B C6B C7B C14B 140.34(14) . . . . ? C1B C6B C7B C14B -43.41(19) . . . . ? C6B C7B C8B C9B -169.83(13) . . . . ? C14B C7B C8B C9B -43.59(17) . . . . ? C7B C8B C9B O9B -88.13(18) . . . . ? C7B C8B C9B C10B 89.41(17) . . . . ? O9B C9B C10B C11B 107.94(17) . . . . ? C8B C9B C10B C11B -69.60(17) . . . . ? C9B C10B C11B O11B 56.28(17) . . . . ? C9B C10B C11B C12B -60.05(17) . . . . ? C12B C11B O11B C14B 33.45(15) . . . . ? C10B C11B O11B C14B -87.57(14) . . . . ? O11B C11B C12B C13B -32.87(15) . . . . ? C10B C11B C12B C13B 87.17(14) . . . . ? C11B C12B C13B O13B -157.40(15) . . . . ? C11B C12B C13B C14B 21.58(15) . . . . ? C11B O11B C14B C15B -133.57(12) . . . . ? C11B O11B C14B C13B -19.19(14) . . . . ? C11B O11B C14B C7B 100.30(13) . . . . ? O13B C13B C14B O11B 176.56(13) . . . . ? C12B C13B C14B O11B -2.48(14) . . . . ? O13B C13B C14B C15B -65.00(17) . . . . ? C12B C13B C14B C15B 115.97(12) . . . . ? O13B C13B C14B C7B 54.46(18) . . . . ? C12B C13B C14B C7B -124.57(12) . . . . ? C6B C7B C14B O11B 86.99(14) . . . . ? C8B C7B C14B O11B -35.60(15) . . . . ? C6B C7B C14B C15B -39.74(16) . . . . ? C8B C7B C14B C15B -162.32(11) . . . . ? C6B C7B C14B C13B -156.23(12) . . . . ? C8B C7B C14B C13B 81.18(14) . . . . ? O11B C14B C15B O15B -172.05(12) . . . . ? C13B C14B C15B O15B 74.25(16) . . . . ? C7B C14B C15B O15B -44.43(18) . . . . ? O11B C14B C15B O16B 10.44(16) . . . . ? C13B C14B C15B O16B -103.26(13) . . . . ? C7B C14B C15B O16B 138.06(12) . . . . ? O15B C15B O16B C16B -0.6(2) . . . . ? C14B C15B O16B C16B 176.77(12) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.354 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.043 _diffrn_orient_matrix_type standard _diffrn_orient_matrix_UB_11 0.1060969 _diffrn_orient_matrix_UB_12 -0.0236176 _diffrn_orient_matrix_UB_13 -0.0339294 _diffrn_orient_matrix_UB_21 0.0012428 _diffrn_orient_matrix_UB_22 -0.0279975 _diffrn_orient_matrix_UB_23 0.0715073 _diffrn_orient_matrix_UB_31 -0.0092487 _diffrn_orient_matrix_UB_32 -0.0847421 _diffrn_orient_matrix_UB_33 -0.0196926 _symmetry_space_group_name_Hall '-P 1' _exptl_crystal_id 'Doyle/DeanaJaber Diazo Decomp-Major product @ 120K' _diffrn_measurement_frame_width-CCD -0.3 _diffrn_measurement_details 610,610,610 _diffrn_measurement_total_frames-CCD 1830 _diffrn_measurement_frame_time-CCD 60 _diffrn_measurement_total_time-CCD 33.5 _diffrn_source_voltage 50.00 _diffrn_source_current 30.00 _diffrn_detector_distance-CCD 5.0000 _diffrn_measurement_frame_size-CCD 1024 _diffrn_measurement_specimen_support 'MiTeGen loop' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker Smart Apex II' #_______________________________________________________________________________ # _publ_section_references ; Bruker (2005). Apex2. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (1990). Acta Cryst. A46, 467-473. Sheldrick, G. M. (1996). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (1997). SHELXL-97. University of G\"ottingen, Germany. Spek, A. L. (1990). Acta Cryst., A46, C-34. ;