Electronic Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _audit_creation_method maXus _journal_coden_Cambridge 177 loop_ _publ_author_name 'Joern B. Christensen' 'Ulrik Boas' 'Knud J. Jensen' 'Mikkel Jessing' 'Michael Pittelkow' _publ_contact_author_name 'Jorn B. Christensen' _publ_contact_author_address ; Associate Professor Jorn B. Christensen The H. C. Orsted Institute Department of Chemistry University of Copenhagen Universitetsparken 5 DK-2100 Denmark. ; _publ_contact_author_email jbc@kiku.dk _publ_contact_author_fax '++ 45 35320112 ' _publ_contact_author_phone '++ 45 35320194' _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Role of the peri-effect in synthesis and reactivity of highly substituted naphthaldehydes: a novel backbone amide linker for solid-phase synthesis ; _publ_section_abstract ; ? ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All diagrams and calculations were performed using maXus (Bruker Nonius, Delft & MacScience, Japan). ; _publ_section_acknowledgements ; The authers acknowledge Peter Hammersh?j and Magnus Magnussen for their help with the crystal structures. ; _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of Gottingen, Germany. ; data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 248480' _chemical_compound_source 'Local laboratory' _exptl_crystal_description Needles _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_F_000 520 _cell_measurement_temperature 122 _refine_ls_hydrogen_treatment constr _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'EvalCCD(Duisberg, 2003)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 246.262 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z '-X,+Y+ 1/2,-Z+ 1/2' '+X,-Y+ 1/2,+Z+ 1/2' _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_cell_setting Monoclinic _chemical_formula_moiety 'C14 H14 O4 ' _chemical_formula_sum 'C14 H14 O4 ' _chemical_name_systematic ; ? ; _cell_length_a 3.9763(3) _cell_length_b 11.8245(10) _cell_length_c 24.323(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.353(7) _cell_angle_gamma 90.00 _cell_volume 1139.2(2) _diffrn_reflns_number 30841 _diffrn_reflns_theta_max 31.98 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_full 31.98 _cell_measurement_reflns_used 10359 _cell_measurement_theta_min 1.68 _cell_measurement_theta_max 31.98 _diffrn_measurement_method CCD _computing_cell_refinement 'COLLECT (Nonius, 1999)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' _exptl_absorpt_coefficient_mu 0.105 _reflns_number_total 3800 _reflns_number_gt 2620 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3800 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1029 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1900 _refine_ls_wR_factor_gt 0.1606 _refine_ls_goodness_of_fit_ref 1.255 _refine_ls_restrained_S_all 1.255 _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 0.9889(3) 0.27485(9) 0.82596(4) 0.0197(3) Uani 1 1 d . . . O2 O 0.3792(3) 0.01267(9) 0.56449(4) 0.0180(3) Uani 1 1 d . . . O3 O 0.1800(3) 0.40078(9) 0.60043(4) 0.0171(3) Uani 1 1 d . . . C4 C 0.6417(4) 0.18727(12) 0.68648(6) 0.0128(3) Uani 1 1 d . . . O5 O -0.0558(3) 0.28229(10) 0.50325(5) 0.0249(3) Uani 1 1 d . . . C6 C 0.6070(4) 0.09187(12) 0.65128(6) 0.0139(3) Uani 1 1 d . . . C7 C 0.8397(4) 0.27290(13) 0.77344(6) 0.0153(3) Uani 1 1 d . . . C8 C 0.4266(4) 0.09992(13) 0.60089(6) 0.0139(3) Uani 1 1 d . . . C9 C 0.3205(4) 0.29867(13) 0.61535(6) 0.0143(3) Uani 1 1 d . . . C10 C 0.5371(4) 0.38651(13) 0.70386(6) 0.0159(3) Uani 1 1 d . . . C11 C 0.8132(4) 0.17932(13) 0.73999(6) 0.0145(3) Uani 1 1 d . . . C12 C 0.4988(4) 0.29186(12) 0.66834(6) 0.0134(3) Uani 1 1 d . . . C13 C 0.2744(4) 0.20403(12) 0.58177(6) 0.0137(3) Uani 1 1 d . . . C14 C 1.1320(4) 0.17273(13) 0.84818(6) 0.0210(4) Uani 1 1 d . . . C15 C 0.3581(4) 0.46303(13) 0.56119(6) 0.0206(3) Uani 1 1 d . . . C16 C 0.0515(4) 0.20211(13) 0.53007(6) 0.0178(3) Uani 1 1 d . . . C17 C 0.7022(4) 0.37733(13) 0.75498(6) 0.0172(3) Uani 1 1 d . . . C18 C 0.5300(4) -0.09312(12) 0.58076(6) 0.0185(3) Uani 1 1 d . . . H6 H 0.7354 0.0217 0.6623 0.017 Uiso 1 1 d R . . H10 H 0.4235 0.4533 0.6923 0.019 Uiso 1 1 d R . . H11 H 0.9057 0.1068 0.7528 0.017 Uiso 1 1 d R . . H14A H 1.2847 0.1466 0.8306 0.025 Uiso 1 1 d R . . H14B H 1.1935 0.1862 0.8860 0.025 Uiso 1 1 d R . . H14C H 0.9728 0.1111 0.8473 0.025 Uiso 1 1 d R . . H15A H 0.2211 0.5254 0.5517 0.025 Uiso 1 1 d R . . H15B H 0.5572 0.4800 0.5752 0.025 Uiso 1 1 d R . . H15C H 0.3765 0.4265 0.5362 0.025 Uiso 1 1 d R . . H16 H -0.0013 0.1386 0.5198 0.021 Uiso 1 1 d R . . H17 H 0.7410 0.4390 0.7784 0.021 Uiso 1 1 d R . . H18A H 0.4616 -0.1169 0.6106 0.022 Uiso 1 1 d R . . H18B H 0.4601 -0.1432 0.5517 0.022 Uiso 1 1 d R . . H18C H 0.7873 -0.0848 0.5879 0.022 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 O1 0.0263(6) 0.0175(6) 0.0140(5) -0.0019(4) -0.0054(4) 0.0015(5) O2 0.0230(6) 0.0149(5) 0.0149(5) -0.0022(4) -0.0042(4) 0.0036(4) O3 0.0193(6) 0.0144(5) 0.0180(5) 0.0048(4) 0.0038(4) 0.0040(4) C4 0.0117(6) 0.0135(7) 0.0133(7) 0.0017(5) 0.0010(5) 0.0004(5) O5 0.0292(7) 0.0227(7) 0.0211(6) 0.0044(5) -0.0080(5) 0.0029(5) C6 0.0142(7) 0.0136(7) 0.0137(6) 0.0014(5) 0.0009(5) 0.0010(6) C7 0.0150(7) 0.0185(8) 0.0123(7) 0.0003(5) 0.0004(5) -0.0020(6) C8 0.0143(7) 0.0151(7) 0.0125(6) 0.0002(5) 0.0022(5) -0.0007(5) C9 0.0126(7) 0.0156(7) 0.0150(7) 0.0032(5) 0.0029(5) 0.0020(5) C10 0.0168(7) 0.0135(7) 0.0179(7) 0.0010(5) 0.0035(6) 0.0011(6) C11 0.0155(7) 0.0144(7) 0.0133(7) 0.0012(5) 0.0001(5) 0.0002(6) C12 0.0133(7) 0.0136(7) 0.0137(7) 0.0029(5) 0.0037(5) 0.0007(5) C13 0.0135(7) 0.0147(7) 0.0128(6) 0.0033(5) 0.0005(5) 0.0008(5) C14 0.0259(8) 0.0182(8) 0.0177(7) 0.0027(6) -0.0043(6) -0.0012(6) C15 0.0206(8) 0.0184(8) 0.0232(8) 0.0052(6) 0.0030(6) 0.0007(6) C16 0.0167(7) 0.0201(8) 0.0163(7) -0.0010(6) -0.0005(6) 0.0007(6) C17 0.0198(8) 0.0152(7) 0.0167(7) -0.0023(5) 0.0021(6) -0.0007(6) C18 0.0216(8) 0.0153(7) 0.0179(7) -0.0024(6) -0.0021(6) 0.0029(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.3607(17) . ? O1 C14 1.4212(18) . ? O2 C8 1.3617(17) . ? O2 C18 1.4281(17) . ? O3 C9 1.3661(17) . ? O3 C15 1.4398(18) . ? C4 C12 1.4153(19) . ? C4 C6 1.416(2) . ? C4 C11 1.4184(19) . ? O5 C16 1.2073(18) . ? C6 C8 1.3680(19) . ? C7 C11 1.372(2) . ? C7 C17 1.408(2) . ? C8 C13 1.431(2) . ? C9 C13 1.388(2) . ? C9 C12 1.418(2) . ? C10 C17 1.358(2) . ? C10 C12 1.414(2) . ? C13 C16 1.4739(19) . ? C6 H6 0.9990 . ? C10 H10 0.9406 . ? C11 H11 0.9734 . ? C14 H14A 0.8323 . ? C14 H14B 0.9449 . ? C14 H14C 0.9641 . ? C15 H15A 0.9337 . ? C15 H15B 0.8573 . ? C15 H15C 0.7552 . ? C16 H16 0.8129 . ? C17 H17 0.9308 . ? C18 H18A 0.8445 . ? C18 H18B 0.9453 . ? C18 H18C 1.0271 . ? 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 C7 O1 C14 118.02(12) . . ? C8 O2 C18 116.91(11) . . ? C9 O3 C15 114.49(11) . . ? C12 C4 C6 119.51(13) . . ? C12 C4 C11 119.44(13) . . ? C6 C4 C11 121.05(13) . . ? C8 C6 C4 120.15(13) . . ? O1 C7 C11 125.09(13) . . ? O1 C7 C17 114.19(13) . . ? C11 C7 C17 120.71(13) . . ? O2 C8 C6 124.17(13) . . ? O2 C8 C13 114.21(12) . . ? C6 C8 C13 121.62(13) . . ? O3 C9 C13 121.77(13) . . ? O3 C9 C12 116.87(13) . . ? C13 C9 C12 121.25(13) . . ? C17 C10 C12 120.89(14) . . ? C7 C11 C4 119.76(13) . . ? C4 C12 C10 118.85(13) . . ? C4 C12 C9 119.21(13) . . ? C10 C12 C9 121.94(13) . . ? C9 C13 C8 118.18(13) . . ? C9 C13 C16 123.56(13) . . ? C8 C13 C16 117.99(13) . . ? O5 C16 C13 127.33(15) . . ? C10 C17 C7 120.33(14) . . ? C8 C6 H6 121.0 . . ? C4 C6 H6 118.6 . . ? C17 C10 H10 121.5 . . ? C12 C10 H10 117.3 . . ? C7 C11 H11 120.8 . . ? C4 C11 H11 119.4 . . ? O1 C14 H14A 113.9 . . ? O1 C14 H14B 106.7 . . ? H14A C14 H14B 115.2 . . ? O1 C14 H14C 113.2 . . ? H14A C14 H14C 102.4 . . ? H14B C14 H14C 105.1 . . ? O3 C15 H15A 104.9 . . ? O3 C15 H15B 110.3 . . ? H15A C15 H15B 114.3 . . ? O3 C15 H15C 109.2 . . ? H15A C15 H15C 110.3 . . ? H15B C15 H15C 107.6 . . ? O5 C16 H16 119.3 . . ? C13 C16 H16 113.3 . . ? C10 C17 H17 122.6 . . ? C7 C17 H17 116.9 . . ? O2 C18 H18A 111.7 . . ? O2 C18 H18B 104.6 . . ? H18A C18 H18B 109.8 . . ? O2 C18 H18C 110.5 . . ? H18A C18 H18C 106.1 . . ? H18B C18 H18C 114.2 . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.422 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.077 data_compound_2 _database_code_depnum_ccdc_archive 'CCDC 248481' _chemical_compound_source 'Local laboratory' _exptl_crystal_description Needles _exptl_crystal_colour Yellow _cell_measurement_temperature 122 _refine_ls_hydrogen_treatment constr _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 # Submission details _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'EvalCCD (Duisenberg, 2003)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 232.235 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z '-X,+Y+ 1/2,-Z+ 1/2' '+X,-Y+ 1/2,+Z+ 1/2' _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_cell_setting Monoclinic _chemical_formula_moiety 'C13 H12 O4 ' _chemical_formula_sum 'C13 H12 O4 ' _chemical_name_systematic ; ? ; _cell_length_a 18.985(3) _cell_length_b 3.9181(6) _cell_length_c 14.504(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.443(11) _cell_angle_gamma 90.00 _cell_volume 1049.3(3) _diffrn_reflns_number 38108 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 1.10 _diffrn_reflns_theta_full 30.00 _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.10 _cell_measurement_theta_max 30.00 _diffrn_measurement_method CCD _computing_cell_refinement 'COLLECT (Nonius. 1999)' _computing_structure_solution 'SIR97 (ALTOMARE, 1999)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' _exptl_absorpt_coefficient_mu 0.109 _reflns_number_total 3077 _reflns_number_gt 2159 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3077 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0875 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1729 _refine_ls_wR_factor_gt 0.1476 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.176 _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 O1 O 0.23490(5) -0.2771(3) 0.49990(7) 0.0210(3) Uani 1 1 d . . . O2 O 0.06153(5) 0.1543(3) 0.09177(7) 0.0192(3) Uani 1 1 d . . . O3 O 0.36472(6) -0.2504(3) 0.60069(8) 0.0282(3) Uani 1 1 d . . . O4 O 0.42443(5) 0.2755(3) 0.39717(7) 0.0215(3) Uani 1 1 d . . . C5 C 0.11303(7) 0.1012(4) 0.17281(10) 0.0151(3) Uani 1 1 d . . . C6 C 0.23311(7) 0.1353(4) 0.27448(10) 0.0144(3) Uani 1 1 d . . . C7 C 0.13518(8) -0.1443(4) 0.32870(10) 0.0165(3) Uani 1 1 d . . . C8 C 0.18405(7) 0.2036(4) 0.18701(10) 0.0154(3) Uani 1 1 d . . . C9 C 0.35347(7) 0.1785(4) 0.37446(10) 0.0171(3) Uani 1 1 d . . . C10 C 0.08821(7) -0.0742(4) 0.24398(10) 0.0169(3) Uani 1 1 d . . . C11 C 0.33093(7) -0.0029(4) 0.44832(10) 0.0169(3) Uani 1 1 d . . . C12 C 0.30659(8) 0.2439(4) 0.28986(10) 0.0165(3) Uani 1 1 d . . . C13 C 0.08405(8) 0.3187(4) 0.01540(10) 0.0195(3) Uani 1 1 d . . . C14 C 0.25863(7) -0.1081(4) 0.43266(10) 0.0158(3) Uani 1 1 d . . . C15 C 0.38125(8) -0.0909(5) 0.53500(11) 0.0232(4) Uani 1 1 d . . . C16 C 0.45085(8) 0.4420(4) 0.32463(11) 0.0239(4) Uani 1 1 d . . . C17 C 0.20834(7) -0.0394(4) 0.34611(10) 0.0148(3) Uani 1 1 d . . . H1 H 0.2730 -0.3107 0.5502 0.025 Uiso 1 1 d R . . H7 H 0.1193 -0.2754 0.3776 0.020 Uiso 1 1 d R . . H8 H 0.2028 0.3172 0.1386 0.019 Uiso 1 1 d R . . H10 H 0.0385 -0.1403 0.2318 0.020 Uiso 1 1 d R . . H12 H 0.3224 0.3719 0.2424 0.020 Uiso 1 1 d R . . H13A H 0.1189 0.2072 0.0023 0.023 Uiso 1 1 d R . . H13B H 0.1019 0.5445 0.0300 0.023 Uiso 1 1 d R . . H13C H 0.0440 0.3203 -0.0382 0.023 Uiso 1 1 d R . . H15 H 0.4314 -0.0033 0.5425 0.028 Uiso 1 1 d R . . H16A H 0.4445 0.3003 0.2696 0.029 Uiso 1 1 d R . . H16B H 0.4330 0.6366 0.3085 0.029 Uiso 1 1 d R . . H16C H 0.5018 0.4781 0.3501 0.029 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 O1 0.0190(5) 0.0286(6) 0.0155(5) 0.0046(5) 0.0043(4) -0.0001(5) O2 0.0148(5) 0.0257(6) 0.0154(5) 0.0014(4) 0.0001(4) -0.0016(4) O3 0.0246(6) 0.0400(7) 0.0181(6) 0.0066(5) 0.0011(4) -0.0015(5) O4 0.0126(5) 0.0282(6) 0.0223(6) 0.0033(5) 0.0010(4) -0.0037(4) C5 0.0145(6) 0.0147(7) 0.0152(6) -0.0024(6) 0.0018(5) 0.0018(5) C6 0.0131(6) 0.0149(7) 0.0148(7) -0.0020(6) 0.0024(5) 0.0009(5) C7 0.0168(7) 0.0166(7) 0.0174(7) -0.0007(6) 0.0066(5) -0.0007(5) C8 0.0145(6) 0.0173(7) 0.0147(6) -0.0005(6) 0.0037(5) -0.0003(5) C9 0.0127(6) 0.0191(7) 0.0190(7) -0.0026(6) 0.0027(5) -0.0001(5) C10 0.0129(6) 0.0185(7) 0.0193(7) -0.0027(6) 0.0036(5) -0.0011(6) C11 0.0151(6) 0.0190(7) 0.0155(7) -0.0019(6) 0.0015(5) 0.0007(6) C12 0.0153(7) 0.0182(7) 0.0162(7) 0.0004(6) 0.0042(5) -0.0015(5) C13 0.0185(7) 0.0238(8) 0.0156(7) 0.0004(6) 0.0027(5) -0.0006(6) C14 0.0158(7) 0.0168(7) 0.0157(7) -0.0001(6) 0.0054(5) 0.0005(5) C15 0.0191(7) 0.0293(9) 0.0193(7) 0.0002(7) 0.0009(6) -0.0005(6) C16 0.0152(7) 0.0268(9) 0.0293(8) 0.0067(7) 0.0043(6) -0.0013(6) C17 0.0146(6) 0.0145(7) 0.0152(6) -0.0021(5) 0.0035(5) 0.0010(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 C14 1.3405(17) . ? O2 C5 1.3588(16) . ? O2 C13 1.4299(17) . ? O3 C15 1.2394(19) . ? O4 C9 1.3645(16) . ? O4 C16 1.4244(18) . ? C5 C8 1.3758(19) . ? C5 C10 1.409(2) . ? C6 C17 1.413(2) . ? C6 C8 1.4139(19) . ? C6 C12 1.4255(19) . ? C7 C10 1.368(2) . ? C7 C17 1.4137(19) . ? C9 C12 1.362(2) . ? C9 C11 1.431(2) . ? C11 C14 1.4003(19) . ? C11 C15 1.4329(19) . ? C14 C17 1.4151(19) . ? O1 H1 0.9093 . ? C7 H7 0.9775 . ? C8 H8 0.9659 . ? C10 H10 0.9538 . ? C12 H12 0.9551 . ? C13 H13A 0.8508 . ? C13 H13B 0.9538 . ? C13 H13C 0.9525 . ? C15 H15 0.9943 . ? C16 H16A 0.9572 . ? C16 H16B 0.8455 . ? C16 H16C 0.9617 . ? 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 C5 O2 C13 117.04(11) . . ? C9 O4 C16 116.53(11) . . ? O2 C5 C8 124.60(13) . . ? O2 C5 C10 114.36(12) . . ? C8 C5 C10 121.04(13) . . ? C17 C6 C8 119.28(12) . . ? C17 C6 C12 120.70(12) . . ? C8 C6 C12 120.02(13) . . ? C10 C7 C17 120.68(13) . . ? C5 C8 C6 119.82(13) . . ? C12 C9 O4 124.52(14) . . ? C12 C9 C11 121.41(13) . . ? O4 C9 C11 114.07(12) . . ? C7 C10 C5 119.79(13) . . ? C14 C11 C9 118.49(12) . . ? C14 C11 C15 120.01(13) . . ? C9 C11 C15 121.44(13) . . ? C9 C12 C6 119.70(14) . . ? O1 C14 C11 120.66(12) . . ? O1 C14 C17 117.90(12) . . ? C11 C14 C17 121.45(13) . . ? O3 C15 C11 124.01(14) . . ? C6 C17 C7 119.39(12) . . ? C6 C17 C14 118.24(12) . . ? C7 C17 C14 122.36(13) . . ? C14 O1 H1 108.4 . . ? C10 C7 H7 120.7 . . ? C17 C7 H7 118.6 . . ? C5 C8 H8 122.6 . . ? C6 C8 H8 117.6 . . ? C7 C10 H10 121.5 . . ? C5 C10 H10 118.8 . . ? C9 C12 H12 120.0 . . ? C6 C12 H12 120.2 . . ? O2 C13 H13A 109.3 . . ? O2 C13 H13B 113.7 . . ? H13A C13 H13B 105.7 . . ? O2 C13 H13C 108.1 . . ? H13A C13 H13C 109.6 . . ? H13B C13 H13C 110.5 . . ? O3 C15 H15 119.9 . . ? C11 C15 H15 116.0 . . ? O4 C16 H16A 110.7 . . ? O4 C16 H16B 115.5 . . ? H16A C16 H16B 109.1 . . ? O4 C16 H16C 106.2 . . ? H16A C16 H16C 109.0 . . ? H16B C16 H16C 106.0 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.432 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.066