# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Girard, Emeline' 'Desvergnes, Valerie' 'Tarnus, Celine' 'Landais, Yannick' _publ_contact_author_name 'Landais, Yannick' _publ_contact_author_email y.landais@ism.u-bordeaux1.fr _publ_section_title ; Desymmetrization of 7-Silylcycloheptatrienes: Towards The Synthesis of New Aminocycloheptitols ; # Attachment '- 11.cif' data_eg141f2_0m _database_code_depnum_ccdc_archive 'CCDC 787046' #TrackingRef '- 11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H33 N O7 Si' _chemical_formula_weight 475.60 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' N N 0.0311 0.0180 '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' Si Si 0.2541 0.3302 '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 9.0179(10) _cell_length_b 9.5313(11) _cell_length_c 15.0553(16) _cell_angle_alpha 86.959(3) _cell_angle_beta 78.879(2) _cell_angle_gamma 80.525(3) _cell_volume 1252.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 1.190 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _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 12802 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 55.35 _reflns_number_total 2996 _reflns_number_gt 2955 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROTEUM2 SUITE' _computing_cell_refinement 'PROTEUM2 SUITE' _computing_data_reduction 'PROTEUM2 SUITE' _computing_structure_solution 'SHELXD-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SXGRAPH _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^)+(0.0529P)^2^+0.8066P] 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 SHELXL _refine_ls_extinction_coef 0.0145(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2996 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1045 _refine_ls_wR_factor_gt 0.1043 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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 Si01 Si 0.81342(6) 0.99334(6) 0.25796(4) 0.0234(2) Uani 1 1 d . . . O6 O 0.71148(16) 1.33376(15) -0.05016(9) 0.0264(4) Uani 1 1 d . . . O7 O 0.81885(16) 1.41314(14) 0.07389(9) 0.0274(4) Uani 1 1 d . . . O1 O 0.77804(16) 1.27663(14) 0.34638(9) 0.0266(4) Uani 1 1 d . . . O5 O 0.77827(17) 1.09721(16) -0.02027(10) 0.0321(4) Uani 1 1 d . . . N1 N 0.82292(19) 1.26191(17) 0.06916(11) 0.0237(4) Uani 1 1 d . . . O2 O 1.01010(16) 1.42879(15) 0.26549(9) 0.0282(4) Uani 1 1 d . . . O3 O 0.55131(19) 1.42117(18) 0.35341(11) 0.0422(5) Uani 1 1 d . . . O4 O 0.8662(2) 1.56463(18) 0.37842(11) 0.0439(5) Uani 1 1 d . . . C010 C 1.0928(2) 1.2281(2) 0.07508(13) 0.0254(5) Uani 1 1 d . . . H010 H 1.1835 1.1701 0.0508 0.030 Uiso 1 1 calc R . . C011 C 0.8084(2) 1.2946(2) 0.24802(13) 0.0233(5) Uani 1 1 d . . . H011 H 0.7105 1.3067 0.2272 0.028 Uiso 1 1 calc R . . C012 C 0.9040(2) 1.1558(2) 0.21062(13) 0.0223(5) Uani 1 1 d . . . H012 H 1.0006 1.1470 0.2326 0.027 Uiso 1 1 calc R . . C013 C 0.9463(2) 1.1693(2) 0.10532(13) 0.0226(5) Uani 1 1 d . . . H013 H 0.9589 1.0745 0.0801 0.027 Uiso 1 1 calc R . . C014 C 0.7725(2) 1.2216(2) -0.00485(13) 0.0241(5) Uani 1 1 d . . . C015 C 0.5998(2) 1.0419(2) 0.28450(14) 0.0264(5) Uani 1 1 d . . . C016 C 0.8780(2) 1.4298(2) 0.22358(14) 0.0246(5) Uani 1 1 d . . . H016 H 0.8010 1.5119 0.2451 0.030 Uiso 1 1 calc R . . C017 C 0.9338(2) 1.4483(2) 0.12041(14) 0.0253(5) Uani 1 1 d . . . H017 H 0.9406 1.5493 0.1080 0.030 Uiso 1 1 calc R . . C018 C 0.2810(3) 1.1209(3) 0.32342(18) 0.0418(6) Uani 1 1 d . . . H018 H 0.1754 1.1477 0.3366 0.050 Uiso 1 1 calc R . . C019 C 1.0870(2) 1.3657(2) 0.08449(13) 0.0256(5) Uani 1 1 d . . . H019 H 1.1740 1.4089 0.0695 0.031 Uiso 1 1 calc R . . C020 C 0.6168(2) 1.3147(2) -0.11809(15) 0.0315(6) Uani 1 1 d . . . C021 C 0.9880(3) 1.5005(2) 0.34407(15) 0.0331(6) Uani 1 1 d . . . C022 C 0.7147(3) 1.2306(3) -0.19734(16) 0.0438(7) Uani 1 1 d . . . H02A H 0.7978 1.2796 -0.2243 0.066 Uiso 1 1 calc R . . H02B H 0.6534 1.2212 -0.2416 0.066 Uiso 1 1 calc R . . H02C H 0.7548 1.1379 -0.1763 0.066 Uiso 1 1 calc R . . C023 C 0.5668(3) 1.4663(3) -0.14727(16) 0.0407(6) Uani 1 1 d . . . H02D H 0.6549 1.5070 -0.1763 0.061 Uiso 1 1 calc R . . H02E H 0.5157 1.5207 -0.0952 0.061 Uiso 1 1 calc R . . H02F H 0.4982 1.4677 -0.1889 0.061 Uiso 1 1 calc R . . C024 C 0.6423(3) 1.3466(2) 0.39060(15) 0.0315(6) Uani 1 1 d . . . C025 C 0.5146(3) 1.0183(3) 0.36993(15) 0.0379(6) Uani 1 1 d . . . H025 H 0.5646 0.9757 0.4153 0.045 Uiso 1 1 calc R . . C026 C 0.8924(3) 0.9282(2) 0.36118(15) 0.0310(5) Uani 1 1 d . . . H02G H 0.8671 1.0017 0.4053 0.047 Uiso 1 1 calc R . . H02H H 1.0016 0.9035 0.3453 0.047 Uiso 1 1 calc R . . H02I H 0.8491 0.8459 0.3861 0.047 Uiso 1 1 calc R . . C027 C 0.4830(3) 1.2444(3) -0.07240(19) 0.0512(7) Uani 1 1 d . . . H02J H 0.4244 1.3016 -0.0232 0.077 Uiso 1 1 calc R . . H02K H 0.5199 1.1520 -0.0495 0.077 Uiso 1 1 calc R . . H02L H 0.4194 1.2350 -0.1154 0.077 Uiso 1 1 calc R . . C028 C 0.8620(3) 0.8507(2) 0.17266(15) 0.0320(6) Uani 1 1 d . . . H02M H 0.8215 0.8842 0.1196 0.048 Uiso 1 1 calc R . . H02N H 0.8185 0.7686 0.1977 0.048 Uiso 1 1 calc R . . H02O H 0.9712 0.8257 0.1567 0.048 Uiso 1 1 calc R . . C029 C 0.6240(3) 1.3169(3) 0.49047(16) 0.0452(7) Uani 1 1 d . . . H02P H 0.7132 1.2552 0.5033 0.068 Uiso 1 1 calc R . . H02Q H 0.5354 1.2718 0.5106 0.068 Uiso 1 1 calc R . . H02R H 0.6118 1.4047 0.5215 0.068 Uiso 1 1 calc R . . C030 C 0.3615(3) 1.1454(3) 0.23824(17) 0.0416(6) Uani 1 1 d . . . H030 H 0.3105 1.1890 0.1935 0.050 Uiso 1 1 calc R . . C031 C 1.1318(3) 1.4876(3) 0.38021(17) 0.0472(7) Uani 1 1 d . . . H03A H 1.2129 1.4307 0.3405 0.071 Uiso 1 1 calc R . . H03B H 1.1177 1.4432 0.4393 0.071 Uiso 1 1 calc R . . H03C H 1.1577 1.5805 0.3842 0.071 Uiso 1 1 calc R . . C032 C 0.5185(3) 1.1049(3) 0.21927(16) 0.0353(6) Uani 1 1 d . . . H032 H 0.5714 1.1203 0.1611 0.042 Uiso 1 1 calc R . . C033 C 0.3574(3) 1.0569(3) 0.38872(17) 0.0460(7) Uani 1 1 d . . . H033 H 0.3031 1.0393 0.4462 0.055 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 Si01 0.0274(4) 0.0206(4) 0.0213(4) -0.0013(3) -0.0035(3) -0.0019(3) O6 0.0295(8) 0.0278(9) 0.0238(8) -0.0026(7) -0.0112(6) -0.0015(6) O7 0.0379(9) 0.0183(8) 0.0284(8) -0.0026(6) -0.0140(7) -0.0012(6) O1 0.0346(9) 0.0252(8) 0.0180(8) -0.0037(6) -0.0022(6) -0.0009(7) O5 0.0413(9) 0.0242(9) 0.0331(9) -0.0071(7) -0.0123(7) -0.0036(7) N1 0.0332(10) 0.0162(9) 0.0225(9) -0.0031(7) -0.0086(8) -0.0016(8) O2 0.0353(9) 0.0296(8) 0.0219(8) -0.0051(7) -0.0081(6) -0.0066(7) O3 0.0414(10) 0.0452(10) 0.0325(9) -0.0084(8) -0.0014(8) 0.0104(8) O4 0.0584(12) 0.0402(10) 0.0336(10) -0.0152(8) -0.0086(9) -0.0040(9) C010 0.0272(12) 0.0298(13) 0.0181(11) -0.0019(9) -0.0039(9) -0.0016(10) C011 0.0292(12) 0.0235(12) 0.0165(11) -0.0023(9) -0.0047(9) -0.0011(9) C012 0.0250(11) 0.0219(11) 0.0201(11) -0.0017(9) -0.0056(9) -0.0017(9) C013 0.0284(12) 0.0179(11) 0.0207(11) -0.0030(9) -0.0047(9) -0.0002(9) C014 0.0232(11) 0.0272(14) 0.0204(11) -0.0022(10) -0.0008(9) -0.0031(9) C015 0.0332(13) 0.0205(11) 0.0262(12) -0.0033(9) -0.0054(10) -0.0050(9) C016 0.0284(12) 0.0223(11) 0.0240(12) -0.0042(9) -0.0084(9) -0.0011(9) C017 0.0353(13) 0.0196(11) 0.0239(12) -0.0015(9) -0.0099(10) -0.0071(9) C018 0.0274(13) 0.0488(16) 0.0495(16) -0.0091(13) -0.0095(12) -0.0015(11) C019 0.0307(12) 0.0296(13) 0.0176(11) 0.0016(9) -0.0051(9) -0.0081(10) C020 0.0269(12) 0.0416(14) 0.0280(12) -0.0087(11) -0.0123(10) -0.0003(10) C021 0.0498(16) 0.0276(13) 0.0241(13) -0.0026(11) -0.0082(11) -0.0106(12) C022 0.0497(16) 0.0512(16) 0.0295(13) -0.0134(12) -0.0147(11) 0.0076(13) C023 0.0404(14) 0.0478(16) 0.0336(14) -0.0073(12) -0.0165(11) 0.0075(12) C024 0.0372(14) 0.0275(13) 0.0274(13) -0.0078(11) -0.0003(11) -0.0028(11) C025 0.0313(14) 0.0532(16) 0.0274(13) 0.0023(11) -0.0059(10) -0.0025(11) C026 0.0338(13) 0.0283(12) 0.0286(12) 0.0014(10) -0.0045(10) -0.0002(10) C027 0.0349(15) 0.0674(19) 0.0559(17) -0.0070(15) -0.0137(13) -0.0140(13) C028 0.0387(13) 0.0252(12) 0.0309(13) -0.0036(10) -0.0021(10) -0.0058(10) C029 0.0594(17) 0.0443(16) 0.0257(13) -0.0067(12) 0.0037(12) -0.0021(13) C030 0.0365(15) 0.0474(15) 0.0450(16) 0.0081(12) -0.0198(12) -0.0073(12) C031 0.0590(17) 0.0574(17) 0.0329(14) -0.0070(13) -0.0178(13) -0.0190(14) C032 0.0368(14) 0.0420(14) 0.0286(13) 0.0066(11) -0.0083(10) -0.0109(11) C033 0.0317(14) 0.0726(19) 0.0303(14) -0.0019(13) 0.0005(11) -0.0057(13) _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 C028 1.861(2) . ? Si01 C026 1.867(2) . ? Si01 C015 1.875(2) . ? Si01 C012 1.910(2) . ? O6 C014 1.336(3) . ? O6 C020 1.488(3) . ? O7 N1 1.441(2) . ? O7 C017 1.448(3) . ? O1 C024 1.360(3) . ? O1 C011 1.459(2) . ? O5 C014 1.211(3) . ? N1 C014 1.376(3) . ? N1 C013 1.474(3) . ? O2 C021 1.363(3) . ? O2 C016 1.450(3) . ? O3 C024 1.198(3) . ? O4 C021 1.200(3) . ? C010 C019 1.318(3) . ? C010 C013 1.500(3) . ? C011 C016 1.522(3) . ? C011 C012 1.525(3) . ? C012 C013 1.561(3) . ? C015 C032 1.390(3) . ? C015 C025 1.393(3) . ? C016 C017 1.548(3) . ? C017 C019 1.490(3) . ? C018 C033 1.369(4) . ? C018 C030 1.375(4) . ? C020 C027 1.509(4) . ? C020 C023 1.510(3) . ? C020 C022 1.519(3) . ? C021 C031 1.485(3) . ? C024 C029 1.497(3) . ? C025 C033 1.381(3) . ? C030 C032 1.382(3) . ? 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 C028 Si01 C026 109.47(10) . . ? C028 Si01 C015 107.89(10) . . ? C026 Si01 C015 111.54(10) . . ? C028 Si01 C012 110.07(10) . . ? C026 Si01 C012 107.82(10) . . ? C015 Si01 C012 110.06(9) . . ? C014 O6 C020 120.49(16) . . ? N1 O7 C017 112.63(14) . . ? C024 O1 C011 116.10(16) . . ? C014 N1 O7 114.00(16) . . ? C014 N1 C013 120.31(16) . . ? O7 N1 C013 116.72(15) . . ? C021 O2 C016 117.32(17) . . ? C019 C010 C013 116.89(19) . . ? O1 C011 C016 108.66(16) . . ? O1 C011 C012 106.47(16) . . ? C016 C011 C012 116.97(17) . . ? C011 C012 C013 109.35(16) . . ? C011 C012 Si01 112.28(14) . . ? C013 C012 Si01 116.24(14) . . ? N1 C013 C010 108.93(17) . . ? N1 C013 C012 110.51(16) . . ? C010 C013 C012 111.90(16) . . ? O5 C014 O6 127.01(19) . . ? O5 C014 N1 121.05(19) . . ? O6 C014 N1 111.81(18) . . ? C032 C015 C025 116.6(2) . . ? C032 C015 Si01 121.15(16) . . ? C025 C015 Si01 122.23(16) . . ? O2 C016 C011 110.97(16) . . ? O2 C016 C017 106.48(16) . . ? C011 C016 C017 112.64(16) . . ? O7 C017 C019 110.93(16) . . ? O7 C017 C016 108.53(16) . . ? C019 C017 C016 114.73(17) . . ? C033 C018 C030 119.6(2) . . ? C010 C019 C017 116.53(19) . . ? O6 C020 C027 109.06(19) . . ? O6 C020 C023 102.06(17) . . ? C027 C020 C023 112.0(2) . . ? O6 C020 C022 110.07(17) . . ? C027 C020 C022 112.6(2) . . ? C023 C020 C022 110.6(2) . . ? O4 C021 O2 123.0(2) . . ? O4 C021 C031 125.6(2) . . ? O2 C021 C031 111.4(2) . . ? O3 C024 O1 123.7(2) . . ? O3 C024 C029 125.6(2) . . ? O1 C024 C029 110.7(2) . . ? C033 C025 C015 121.5(2) . . ? C018 C030 C032 119.8(2) . . ? C030 C032 C015 122.0(2) . . ? C018 C033 C025 120.5(2) . . ? 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 C017 O7 N1 C014 -151.56(17) . . . . ? C017 O7 N1 C013 -4.1(2) . . . . ? C024 O1 C011 C016 85.2(2) . . . . ? C024 O1 C011 C012 -148.02(17) . . . . ? O1 C011 C012 C013 -177.89(15) . . . . ? C016 C011 C012 C013 -56.2(2) . . . . ? O1 C011 C012 Si01 51.54(19) . . . . ? C016 C011 C012 Si01 173.19(14) . . . . ? C028 Si01 C012 C011 148.88(15) . . . . ? C026 Si01 C012 C011 -91.76(16) . . . . ? C015 Si01 C012 C011 30.10(17) . . . . ? C028 Si01 C012 C013 21.93(18) . . . . ? C026 Si01 C012 C013 141.28(15) . . . . ? C015 Si01 C012 C013 -96.86(15) . . . . ? C014 N1 C013 C010 102.5(2) . . . . ? O7 N1 C013 C010 -42.8(2) . . . . ? C014 N1 C013 C012 -134.22(19) . . . . ? O7 N1 C013 C012 80.5(2) . . . . ? C019 C010 C013 N1 46.9(2) . . . . ? C019 C010 C013 C012 -75.6(2) . . . . ? C011 C012 C013 N1 -32.7(2) . . . . ? Si01 C012 C013 N1 95.66(17) . . . . ? C011 C012 C013 C010 88.8(2) . . . . ? Si01 C012 C013 C010 -142.76(15) . . . . ? C020 O6 C014 O5 10.8(3) . . . . ? C020 O6 C014 N1 -165.10(16) . . . . ? O7 N1 C014 O5 175.54(17) . . . . ? C013 N1 C014 O5 29.4(3) . . . . ? O7 N1 C014 O6 -8.2(2) . . . . ? C013 N1 C014 O6 -154.39(17) . . . . ? C028 Si01 C015 C032 -65.6(2) . . . . ? C026 Si01 C015 C032 174.14(17) . . . . ? C012 Si01 C015 C032 54.5(2) . . . . ? C028 Si01 C015 C025 114.99(19) . . . . ? C026 Si01 C015 C025 -5.3(2) . . . . ? C012 Si01 C015 C025 -124.89(19) . . . . ? C021 O2 C016 C011 -97.8(2) . . . . ? C021 O2 C016 C017 139.30(18) . . . . ? O1 C011 C016 O2 53.3(2) . . . . ? C012 C011 C016 O2 -67.2(2) . . . . ? O1 C011 C016 C017 172.58(16) . . . . ? C012 C011 C016 C017 52.1(2) . . . . ? N1 O7 C017 C019 49.2(2) . . . . ? N1 O7 C017 C016 -77.68(19) . . . . ? O2 C016 C017 O7 165.27(15) . . . . ? C011 C016 C017 O7 43.4(2) . . . . ? O2 C016 C017 C019 40.6(2) . . . . ? C011 C016 C017 C019 -81.3(2) . . . . ? C013 C010 C019 C017 -2.6(3) . . . . ? O7 C017 C019 C010 -47.3(2) . . . . ? C016 C017 C019 C010 76.2(2) . . . . ? C014 O6 C020 C027 58.5(2) . . . . ? C014 O6 C020 C023 177.10(17) . . . . ? C014 O6 C020 C022 -65.5(2) . . . . ? C016 O2 C021 O4 -1.0(3) . . . . ? C016 O2 C021 C031 178.67(18) . . . . ? C011 O1 C024 O3 -1.0(3) . . . . ? C011 O1 C024 C029 178.81(18) . . . . ? C032 C015 C025 C033 -0.5(3) . . . . ? Si01 C015 C025 C033 178.9(2) . . . . ? C033 C018 C030 C032 0.2(4) . . . . ? C018 C030 C032 C015 -1.3(4) . . . . ? C025 C015 C032 C030 1.4(3) . . . . ? Si01 C015 C032 C030 -178.01(18) . . . . ? C030 C018 C033 C025 0.7(4) . . . . ? C015 C025 C033 C018 -0.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 55.35 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.438 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.051 # Attachment '- 18.cif' data_eg162f1 _database_code_depnum_ccdc_archive 'CCDC 787047' #TrackingRef '- 18.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H27 N O9' _chemical_formula_weight 401.41 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' N N 0.0311 0.0180 '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 monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.432(2) _cell_length_b 9.9220(13) _cell_length_c 10.8403(14) _cell_angle_alpha 90.00 _cell_angle_beta 95.081(4) _cell_angle_gamma 90.00 _cell_volume 1974.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.921 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9136 _exptl_absorpt_correction_T_max 0.9136 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _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 10670 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 55.34 _reflns_number_total 2341 _reflns_number_gt 2247 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.1064P)^2^+4.8190P] 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 SHELXL _refine_ls_extinction_coef 0.0101(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2341 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.1997 _refine_ls_wR_factor_gt 0.1768 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.129 _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 O3 O 0.20402(14) 0.0082(3) 0.0271(2) 0.0244(7) Uani 1 1 d . . . O2 O 0.36039(14) -0.3706(3) 0.2512(3) 0.0281(8) Uani 1 1 d . . . O4 O 0.08476(14) 0.0284(3) 0.1717(2) 0.0261(8) Uani 1 1 d . . . O1 O 0.40967(15) -0.1810(3) 0.1757(3) 0.0326(8) Uani 1 1 d . . . O8 O 0.00315(15) -0.1398(3) 0.1712(3) 0.0322(8) Uani 1 1 d . . . O5 O 0.14597(15) 0.0153(3) 0.4061(2) 0.0279(8) Uani 1 1 d . . . O6 O 0.23738(14) -0.2621(3) 0.2649(2) 0.0274(8) Uani 1 1 d . . . N1 N 0.28931(17) -0.1895(3) 0.2006(3) 0.0240(9) Uani 1 1 d . . . C009 C 0.3591(2) -0.2443(4) 0.2107(3) 0.0252(10) Uani 1 1 d . . . O9 O 0.26829(16) 0.2011(3) 0.0256(3) 0.0362(8) Uani 1 1 d . . . O7 O 0.0839(2) -0.0933(3) 0.5442(3) 0.0541(11) Uani 1 1 d . . . C012 C 0.2174(2) -0.1906(4) 0.3743(4) 0.0275(10) Uani 1 1 d . . . H012 H 0.2035 -0.2597 0.4351 0.033 Uiso 1 1 calc R . . C013 C 0.2852(2) -0.0420(4) 0.2135(4) 0.0224(9) Uani 1 1 d . . . H013 H 0.3228 -0.0016 0.1635 0.027 Uiso 1 1 calc R . . C014 C 0.2108(2) 0.0107(4) 0.1611(3) 0.0228(10) Uani 1 1 d . . . H014 H 0.2064 0.1065 0.1881 0.027 Uiso 1 1 calc R . . C015 C 0.1489(2) -0.1073(4) 0.3347(4) 0.0236(10) Uani 1 1 d . . . H015 H 0.1051 -0.1630 0.3484 0.028 Uiso 1 1 calc R . . C016 C 0.1063(2) 0.0108(5) 0.5058(4) 0.0308(11) Uani 1 1 d . . . C017 C 0.1444(2) -0.0660(4) 0.1988(4) 0.0238(10) Uani 1 1 d . . . H017 H 0.1362 -0.1478 0.1455 0.029 Uiso 1 1 calc R . . C018 C 0.2818(2) -0.1130(4) 0.4351(4) 0.0295(10) Uani 1 1 d . . . H01A H 0.3231 -0.1754 0.4549 0.035 Uiso 1 1 calc R . . H01B H 0.2685 -0.0726 0.5135 0.035 Uiso 1 1 calc R . . C019 C 0.0159(2) -0.0212(4) 0.1640(3) 0.0256(10) Uani 1 1 d . . . C020 C 0.2337(2) 0.1142(5) -0.0291(4) 0.0290(11) Uani 1 1 d . . . C021 C 0.3047(2) -0.0024(4) 0.3497(4) 0.0269(10) Uani 1 1 d . . . H02A H 0.3579 0.0126 0.3643 0.032 Uiso 1 1 calc R . . H02B H 0.2798 0.0827 0.3679 0.032 Uiso 1 1 calc R . . C022 C -0.0380(2) 0.0893(4) 0.1453(4) 0.0284(10) Uani 1 1 d . . . H02C H -0.0125 0.1756 0.1410 0.043 Uiso 1 1 calc R . . H02D H -0.0687 0.0911 0.2146 0.043 Uiso 1 1 calc R . . H02E H -0.0686 0.0744 0.0678 0.043 Uiso 1 1 calc R . . C023 C 0.4606(3) -0.4636(5) 0.1425(4) 0.0401(12) Uani 1 1 d . . . H02F H 0.4242 -0.5093 0.0857 0.060 Uiso 1 1 calc R . . H02G H 0.5050 -0.5182 0.1526 0.060 Uiso 1 1 calc R . . H02H H 0.4718 -0.3753 0.1086 0.060 Uiso 1 1 calc R . . C024 C 0.0965(2) 0.1483(5) 0.5557(4) 0.0343(11) Uani 1 1 d . . . H02I H 0.1211 0.2139 0.5061 0.051 Uiso 1 1 calc R . . H02J H 0.1176 0.1523 0.6418 0.051 Uiso 1 1 calc R . . H02K H 0.0445 0.1696 0.5521 0.051 Uiso 1 1 calc R . . C025 C 0.4306(2) -0.4453(4) 0.2674(4) 0.0297(11) Uani 1 1 d . . . C026 C 0.4827(2) -0.3758(5) 0.3609(4) 0.0374(12) Uani 1 1 d . . . H02L H 0.4963 -0.2880 0.3284 0.056 Uiso 1 1 calc R . . H02M H 0.5265 -0.4313 0.3776 0.056 Uiso 1 1 calc R . . H02N H 0.4594 -0.3627 0.4379 0.056 Uiso 1 1 calc R . . C027 C 0.4070(2) -0.5811(4) 0.3162(5) 0.0387(12) Uani 1 1 d . . . H02O H 0.3732 -0.6246 0.2536 0.058 Uiso 1 1 calc R . . H02P H 0.3827 -0.5673 0.3920 0.058 Uiso 1 1 calc R . . H02Q H 0.4499 -0.6385 0.3342 0.058 Uiso 1 1 calc R . . C028 C 0.2159(3) 0.1064(5) -0.1669(4) 0.0380(12) Uani 1 1 d . . . H02R H 0.1887 0.0233 -0.1875 0.057 Uiso 1 1 calc R . . H02S H 0.2611 0.1062 -0.2081 0.057 Uiso 1 1 calc R . . H02T H 0.1863 0.1844 -0.1948 0.057 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 O3 0.0253(15) 0.0253(15) 0.0226(15) 0.0064(12) 0.0019(12) -0.0022(12) O2 0.0231(15) 0.0248(16) 0.0370(17) 0.0040(13) 0.0049(12) 0.0065(13) O4 0.0170(15) 0.0278(16) 0.0336(16) 0.0033(13) 0.0025(12) 0.0011(12) O1 0.0224(16) 0.0333(17) 0.0428(18) 0.0078(14) 0.0073(13) 0.0035(14) O8 0.0262(16) 0.0274(18) 0.0424(18) -0.0017(14) 0.0004(13) -0.0015(13) O5 0.0280(16) 0.0278(16) 0.0291(16) -0.0030(13) 0.0091(13) -0.0015(12) O6 0.0231(15) 0.0248(16) 0.0344(16) 0.0004(13) 0.0037(12) 0.0008(12) N1 0.0197(18) 0.0257(19) 0.0272(18) 0.0032(15) 0.0054(14) -0.0012(15) C009 0.022(2) 0.032(3) 0.021(2) -0.0006(19) 0.0004(17) 0.001(2) O9 0.0373(18) 0.0313(18) 0.0397(18) 0.0005(15) 0.0023(14) -0.0099(15) O7 0.084(3) 0.040(2) 0.043(2) -0.0009(16) 0.0327(19) -0.0171(19) C012 0.031(2) 0.025(2) 0.026(2) 0.0027(19) 0.0038(18) 0.0021(19) C013 0.020(2) 0.020(2) 0.027(2) 0.0020(17) 0.0051(17) 0.0032(17) C014 0.025(2) 0.021(2) 0.022(2) -0.0011(17) 0.0011(17) 0.0008(17) C015 0.024(2) 0.022(2) 0.026(2) -0.0031(18) 0.0058(17) -0.0017(17) C016 0.027(2) 0.040(3) 0.026(2) 0.001(2) 0.0007(19) 0.001(2) C017 0.021(2) 0.022(2) 0.028(2) 0.0012(18) 0.0012(17) 0.0014(18) C018 0.028(2) 0.036(2) 0.024(2) 0.000(2) -0.0004(18) 0.0029(19) C019 0.024(2) 0.033(3) 0.019(2) -0.0031(18) 0.0010(17) -0.001(2) C020 0.020(2) 0.033(3) 0.034(2) 0.005(2) 0.0068(19) 0.008(2) C021 0.024(2) 0.029(2) 0.027(2) -0.0022(19) -0.0011(18) -0.0016(18) C022 0.022(2) 0.029(2) 0.034(2) 0.0013(19) 0.0030(18) 0.0020(19) C023 0.038(3) 0.042(3) 0.040(3) 0.002(2) 0.003(2) 0.013(2) C024 0.039(3) 0.037(3) 0.028(2) -0.008(2) 0.0050(19) 0.000(2) C025 0.023(2) 0.032(2) 0.033(2) 0.003(2) 0.0001(18) 0.0091(19) C026 0.030(2) 0.039(3) 0.041(3) 0.006(2) -0.005(2) 0.004(2) C027 0.028(2) 0.031(3) 0.057(3) 0.011(2) 0.009(2) 0.009(2) C028 0.033(3) 0.045(3) 0.036(2) 0.009(2) 0.003(2) -0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C020 1.355(5) . ? O3 C014 1.447(5) . ? O2 C009 1.328(5) . ? O2 C025 1.488(5) . ? O4 C019 1.358(5) . ? O4 C017 1.454(5) . ? O1 C009 1.212(5) . ? O8 C019 1.204(5) . ? O5 C016 1.357(5) . ? O5 C015 1.445(5) . ? O6 N1 1.428(4) . ? O6 C012 1.457(5) . ? N1 C009 1.392(5) . ? N1 C013 1.473(5) . ? O9 C020 1.197(5) . ? O7 C016 1.200(5) . ? C012 C018 1.516(6) . ? C012 C015 1.538(6) . ? C013 C014 1.530(6) . ? C013 C021 1.540(6) . ? C014 C017 1.528(6) . ? C015 C017 1.524(6) . ? C016 C024 1.485(6) . ? C018 C021 1.519(6) . ? C019 C022 1.481(6) . ? C020 C028 1.503(6) . ? C023 C025 1.518(6) . ? C025 C026 1.501(6) . ? C025 C027 1.525(6) . ? 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 C020 O3 C014 115.8(3) . . ? C009 O2 C025 119.9(3) . . ? C019 O4 C017 117.7(3) . . ? C016 O5 C015 116.5(3) . . ? N1 O6 C012 112.3(3) . . ? C009 N1 O6 114.8(3) . . ? C009 N1 C013 115.8(3) . . ? O6 N1 C013 114.4(3) . . ? O1 C009 O2 126.9(4) . . ? O1 C009 N1 120.3(4) . . ? O2 C009 N1 112.6(3) . . ? O6 C012 C018 110.9(3) . . ? O6 C012 C015 107.1(3) . . ? C018 C012 C015 116.2(3) . . ? N1 C013 C014 110.9(3) . . ? N1 C013 C021 109.5(3) . . ? C014 C013 C021 113.3(3) . . ? O3 C014 C017 105.1(3) . . ? O3 C014 C013 111.2(3) . . ? C017 C014 C013 116.3(3) . . ? O5 C015 C017 106.9(3) . . ? O5 C015 C012 111.8(3) . . ? C017 C015 C012 112.8(3) . . ? O7 C016 O5 122.1(4) . . ? O7 C016 C024 127.4(4) . . ? O5 C016 C024 110.6(4) . . ? O4 C017 C015 110.1(3) . . ? O4 C017 C014 103.5(3) . . ? C015 C017 C014 114.6(3) . . ? C012 C018 C021 110.6(3) . . ? O8 C019 O4 122.5(4) . . ? O8 C019 C022 126.9(4) . . ? O4 C019 C022 110.6(4) . . ? O9 C020 O3 123.8(4) . . ? O9 C020 C028 126.1(4) . . ? O3 C020 C028 110.2(4) . . ? C018 C021 C013 110.3(3) . . ? O2 C025 C026 110.4(3) . . ? O2 C025 C023 109.6(3) . . ? C026 C025 C023 113.3(4) . . ? O2 C025 C027 102.0(3) . . ? C026 C025 C027 110.9(4) . . ? C023 C025 C027 109.9(4) . . ? 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 C012 O6 N1 C009 108.4(3) . . . . ? C012 O6 N1 C013 -29.0(4) . . . . ? C025 O2 C009 O1 5.4(6) . . . . ? C025 O2 C009 N1 179.9(3) . . . . ? O6 N1 C009 O1 -169.1(3) . . . . ? C013 N1 C009 O1 -32.3(5) . . . . ? O6 N1 C009 O2 16.0(4) . . . . ? C013 N1 C009 O2 152.8(3) . . . . ? N1 O6 C012 C018 -34.4(4) . . . . ? N1 O6 C012 C015 93.3(3) . . . . ? C009 N1 C013 C014 161.9(3) . . . . ? O6 N1 C013 C014 -61.1(4) . . . . ? C009 N1 C013 C021 -72.4(4) . . . . ? O6 N1 C013 C021 64.6(4) . . . . ? C020 O3 C014 C017 150.9(3) . . . . ? C020 O3 C014 C013 -82.4(4) . . . . ? N1 C013 C014 O3 -74.0(4) . . . . ? C021 C013 C014 O3 162.4(3) . . . . ? N1 C013 C014 C017 46.3(4) . . . . ? C021 C013 C014 C017 -77.3(4) . . . . ? C016 O5 C015 C017 140.6(3) . . . . ? C016 O5 C015 C012 -95.6(4) . . . . ? O6 C012 C015 O5 -149.0(3) . . . . ? C018 C012 C015 O5 -24.5(5) . . . . ? O6 C012 C015 C017 -28.6(4) . . . . ? C018 C012 C015 C017 96.0(4) . . . . ? C015 O5 C016 O7 10.8(6) . . . . ? C015 O5 C016 C024 -169.3(3) . . . . ? C019 O4 C017 C015 -74.1(4) . . . . ? C019 O4 C017 C014 162.9(3) . . . . ? O5 C015 C017 O4 -48.4(4) . . . . ? C012 C015 C017 O4 -171.6(3) . . . . ? O5 C015 C017 C014 67.9(4) . . . . ? C012 C015 C017 C014 -55.4(5) . . . . ? O3 C014 C017 O4 -74.6(3) . . . . ? C013 C014 C017 O4 161.9(3) . . . . ? O3 C014 C017 C015 165.4(3) . . . . ? C013 C014 C017 C015 42.0(5) . . . . ? O6 C012 C018 C021 64.8(4) . . . . ? C015 C012 C018 C021 -57.8(5) . . . . ? C017 O4 C019 O8 -4.7(5) . . . . ? C017 O4 C019 C022 175.8(3) . . . . ? C014 O3 C020 O9 5.2(5) . . . . ? C014 O3 C020 C028 -173.9(3) . . . . ? C012 C018 C021 C013 -28.0(5) . . . . ? N1 C013 C021 C018 -31.1(4) . . . . ? C014 C013 C021 C018 93.2(4) . . . . ? C009 O2 C025 C026 61.1(5) . . . . ? C009 O2 C025 C023 -64.5(5) . . . . ? C009 O2 C025 C027 179.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 55.34 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.522 _refine_diff_density_min -0.678 _refine_diff_density_rms 0.094 # Attachment '- 19isomer.CIF' data_eg167p1 _database_code_depnum_ccdc_archive 'CCDC 787048' #TrackingRef '- 19isomer.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N O8' _chemical_formula_weight 376.33 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' N N 0.0311 0.0180 '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 monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 10.5098(10) _cell_length_b 10.1045(10) _cell_length_c 19.7591(19) _cell_angle_alpha 90.00 _cell_angle_beta 98.871(4) _cell_angle_gamma 90.00 _cell_volume 2073.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 0.817 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _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 8479 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.50 _diffrn_reflns_theta_max 46.08 _reflns_number_total 1723 _reflns_number_gt 1603 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXD-97 (Sheldrick, 2008)' _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^)+(0.2000P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0014(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1723 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0818 _refine_ls_R_factor_gt 0.1296 _refine_ls_wR_factor_ref 0.1822 _refine_ls_wR_factor_gt 0.2501 _refine_ls_goodness_of_fit_ref 1.463 _refine_ls_restrained_S_all 1.463 _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 O3 O 0.3812(5) 0.9684(6) 0.1395(3) 0.029(2) Uani 1 1 d . . . O5 O 0.5568(5) 0.8403(6) 0.2283(3) 0.032(2) Uani 1 1 d . . . O8 O 0.5517(5) 1.0876(6) 0.3409(3) 0.035(2) Uani 1 1 d . . . O1 O 0.0081(5) 0.9198(6) 0.1425(3) 0.032(2) Uani 1 1 d . . . O2 O 0.0518(7) 1.1128(6) 0.0950(3) 0.039(2) Uani 1 1 d . . . O10 O 0.6423(6) 0.9385(6) 0.4194(3) 0.034(2) Uani 1 1 d . . . O4 O 0.5260(7) 0.9065(7) 0.0723(4) 0.053(2) Uani 1 1 d . . . N1 N 0.4690(7) 0.8800(8) 0.3488(3) 0.030(2) Uani 1 1 d . . . O6 O 0.6244(6) 0.6466(7) 0.2769(4) 0.053(2) Uani 1 1 d . . . C011 C 0.1239(8) 0.8775(9) 0.2522(5) 0.035(3) Uani 1 1 d . . . H01A H 0.0626 0.8053 0.2502 0.042 Uiso 1 1 calc R . . H01B H 0.0860 0.9530 0.2719 0.042 Uiso 1 1 calc R . . C77 C 0.3752(8) 0.8883(9) 0.2851(4) 0.031(3) Uani 1 1 d . . . H77 H 0.3652 0.9808 0.2704 0.037 Uiso 1 1 calc R . . C013 C 0.4246(7) 0.8077(8) 0.2301(4) 0.026(3) Uani 1 1 d . . . H013 H 0.4184 0.7134 0.2409 0.032 Uiso 1 1 calc R . . C014 C 0.1389(8) 0.9123(8) 0.1807(4) 0.029(3) Uani 1 1 d . . . H014 H 0.1803 0.9991 0.1802 0.035 Uiso 1 1 calc R . . C015 C 0.3577(7) 0.8320(9) 0.1566(4) 0.028(3) Uani 1 1 d . . . H015 H 0.3962 0.7738 0.1256 0.034 Uiso 1 1 calc R . . C76 C 0.2124(8) 0.8126(9) 0.1441(4) 0.030(3) Uani 1 1 d . . . H76 H 0.1829 0.8218 0.0948 0.037 Uiso 1 1 calc R . . C017 C 0.7341(8) 1.0332(9) 0.4566(4) 0.031(3) Uani 1 1 d . . . C018 C 0.6476(8) 0.7527(11) 0.2542(5) 0.035(3) Uani 1 1 d . . . C019 C 0.6602(9) 1.1440(10) 0.4849(5) 0.050(3) Uani 1 1 d . . . H01C H 0.6147 1.1947 0.4477 0.075 Uiso 1 1 calc R . . H01D H 0.7193 1.2005 0.5134 0.075 Uiso 1 1 calc R . . H01E H 0.5998 1.1070 0.5115 0.075 Uiso 1 1 calc R . . C020 C -0.1575(9) 1.0197(10) 0.0665(5) 0.046(3) Uani 1 1 d . . . H02A H -0.1988 0.9416 0.0803 0.069 Uiso 1 1 calc R . . H02B H -0.1580 1.0176 0.0179 0.069 Uiso 1 1 calc R . . H02C H -0.2029 1.0966 0.0783 0.069 Uiso 1 1 calc R . . C021 C 0.8264(9) 1.0810(11) 0.4119(6) 0.054(3) Uani 1 1 d . . . H02D H 0.7814 1.1337 0.3754 0.081 Uiso 1 1 calc R . . H02E H 0.8654 1.0065 0.3929 0.081 Uiso 1 1 calc R . . H02F H 0.8921 1.1335 0.4385 0.081 Uiso 1 1 calc R . . C022 C -0.0225(9) 1.0245(10) 0.1022(5) 0.032(3) Uani 1 1 d . . . C023 C 0.2467(8) 0.8365(9) 0.3022(4) 0.032(3) Uani 1 1 d . . . H02G H 0.2375 0.8671 0.3478 0.038 Uiso 1 1 calc R . . H02H H 0.2507 0.7406 0.3038 0.038 Uiso 1 1 calc R . . C024 C 0.4931(10) 1.1366(10) 0.0933(5) 0.046(3) Uani 1 1 d . . . H02I H 0.4373 1.1832 0.1192 0.069 Uiso 1 1 calc R . . H02J H 0.4751 1.1635 0.0462 0.069 Uiso 1 1 calc R . . H02K H 0.5812 1.1566 0.1112 0.069 Uiso 1 1 calc R . . C025 C 0.5529(9) 0.9757(10) 0.3666(4) 0.025(3) Uani 1 1 d . . . C026 C 0.7779(9) 0.8063(10) 0.2510(5) 0.047(3) Uani 1 1 d . . . H02L H 0.7704 0.8931 0.2310 0.070 Uiso 1 1 calc R . . H02M H 0.8220 0.7491 0.2235 0.070 Uiso 1 1 calc R . . H02N H 0.8257 0.8114 0.2964 0.070 Uiso 1 1 calc R . . C027 C 0.4713(10) 0.9921(10) 0.0983(5) 0.035(3) Uani 1 1 d . . . C028 C 0.8026(11) 0.9504(11) 0.5145(5) 0.053(3) Uani 1 1 d . . . H02O H 0.8470 0.8790 0.4962 0.080 Uiso 1 1 calc R . . H02P H 0.7409 0.9152 0.5408 0.080 Uiso 1 1 calc R . . H02Q H 0.8636 1.0044 0.5435 0.080 Uiso 1 1 calc R . . O20 O 0.1919(5) 0.6802(6) 0.1623(3) 0.037(2) Uani 1 1 d . . . H20 H 0.1717 0.6360 0.1274 0.056 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 O3 0.024(4) 0.028(4) 0.037(4) 0.005(3) 0.007(4) -0.001(3) O5 0.021(4) 0.031(4) 0.042(4) 0.003(3) 0.002(3) 0.001(3) O8 0.028(4) 0.040(5) 0.034(4) 0.000(3) 0.000(3) -0.001(3) O1 0.025(4) 0.027(4) 0.041(4) 0.003(3) -0.001(3) 0.003(3) O2 0.041(4) 0.032(4) 0.043(5) 0.007(3) 0.007(3) -0.002(4) O10 0.030(4) 0.032(4) 0.038(4) 0.001(3) -0.003(4) -0.001(3) O4 0.057(5) 0.050(5) 0.059(5) 0.004(4) 0.034(4) 0.005(4) N1 0.023(5) 0.041(5) 0.024(5) -0.006(4) -0.003(4) -0.012(4) O6 0.035(5) 0.043(5) 0.082(6) 0.018(4) 0.018(4) 0.010(4) C011 0.022(5) 0.044(6) 0.041(7) 0.002(5) 0.009(5) -0.005(4) C77 0.024(6) 0.029(6) 0.038(7) -0.002(4) 0.004(5) 0.003(4) C013 0.015(5) 0.024(5) 0.041(6) 0.001(4) 0.006(4) -0.007(4) C014 0.020(6) 0.036(6) 0.031(6) -0.007(4) -0.001(5) -0.003(4) C015 0.018(6) 0.032(6) 0.035(6) -0.003(4) 0.001(5) 0.000(4) C76 0.028(6) 0.025(6) 0.036(6) 0.007(4) 0.001(4) 0.000(4) C017 0.022(6) 0.040(6) 0.027(6) -0.007(5) -0.005(5) -0.005(5) C018 0.031(7) 0.034(7) 0.044(6) -0.009(5) 0.021(5) -0.002(6) C019 0.053(7) 0.049(7) 0.046(7) -0.007(5) -0.002(6) 0.003(5) C020 0.039(7) 0.048(7) 0.048(6) 0.002(5) -0.001(6) 0.008(5) C021 0.029(6) 0.079(9) 0.051(7) 0.004(6) -0.003(6) -0.012(6) C022 0.027(7) 0.034(7) 0.035(6) -0.006(5) 0.005(5) 0.012(6) C023 0.022(6) 0.029(6) 0.044(6) 0.002(4) 0.005(5) -0.003(4) C024 0.044(6) 0.050(8) 0.047(7) 0.004(5) 0.020(6) -0.008(5) C025 0.024(6) 0.031(7) 0.018(6) 0.013(5) 0.001(5) 0.003(5) C026 0.033(6) 0.061(7) 0.046(6) 0.003(5) 0.007(5) 0.009(5) C027 0.034(7) 0.039(7) 0.033(6) 0.002(5) 0.009(6) -0.001(5) C028 0.056(7) 0.054(7) 0.047(7) 0.005(6) -0.002(6) -0.005(6) O20 0.040(4) 0.028(4) 0.043(4) -0.010(3) 0.002(3) -0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C027 1.362(12) . ? O3 C015 1.450(10) . ? O5 C018 1.344(11) . ? O5 C013 1.433(9) . ? O8 C025 1.238(10) . ? O1 C022 1.334(11) . ? O1 C014 1.465(11) . ? O2 C022 1.208(11) . ? O10 C025 1.345(11) . ? O10 C017 1.472(11) . ? O4 C027 1.198(11) . ? N1 C025 1.319(12) . ? N1 C77 1.477(11) . ? O6 C018 1.201(11) . ? C011 C014 1.489(13) . ? C011 C023 1.556(12) . ? C77 C013 1.513(12) . ? C77 C023 1.534(12) . ? C013 C015 1.533(12) . ? C014 C76 1.517(13) . ? C015 C76 1.522(11) . ? C76 O20 1.411(11) . ? C017 C021 1.489(14) . ? C017 C028 1.509(14) . ? C017 C019 1.519(13) . ? C018 C026 1.483(13) . ? C020 C022 1.484(14) . ? C024 C027 1.484(13) . ? 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 C027 O3 C015 117.7(7) . . ? C018 O5 C013 118.3(7) . . ? C022 O1 C014 118.0(7) . . ? C025 O10 C017 122.1(7) . . ? C025 N1 C77 121.1(7) . . ? C014 C011 C023 117.9(7) . . ? N1 C77 C013 108.9(7) . . ? N1 C77 C023 106.7(7) . . ? C013 C77 C023 112.7(7) . . ? O5 C013 C77 109.6(6) . . ? O5 C013 C015 104.1(6) . . ? C77 C013 C015 115.9(7) . . ? O1 C014 C011 105.8(7) . . ? O1 C014 C76 107.2(6) . . ? C011 C014 C76 115.5(7) . . ? O3 C015 C76 106.7(6) . . ? O3 C015 C013 107.6(6) . . ? C76 C015 C013 115.7(7) . . ? O20 C76 C014 113.6(7) . . ? O20 C76 C015 105.6(7) . . ? C014 C76 C015 114.2(7) . . ? O10 C017 C021 110.6(7) . . ? O10 C017 C028 102.6(7) . . ? C021 C017 C028 110.6(8) . . ? O10 C017 C019 109.2(7) . . ? C021 C017 C019 113.4(8) . . ? C028 C017 C019 109.9(8) . . ? O6 C018 O5 123.8(8) . . ? O6 C018 C026 125.8(9) . . ? O5 C018 C026 110.5(9) . . ? O2 C022 O1 123.7(8) . . ? O2 C022 C020 123.8(9) . . ? O1 C022 C020 112.5(9) . . ? C77 C023 C011 116.2(7) . . ? O8 C025 N1 126.6(8) . . ? O8 C025 O10 122.3(8) . . ? N1 C025 O10 111.1(8) . . ? O4 C027 O3 123.6(9) . . ? O4 C027 C024 126.3(9) . . ? O3 C027 C024 110.0(9) . . ? 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 C025 N1 C77 C013 99.2(9) . . . . ? C025 N1 C77 C023 -138.9(8) . . . . ? C018 O5 C013 C77 105.7(8) . . . . ? C018 O5 C013 C015 -129.7(7) . . . . ? N1 C77 C013 O5 -48.0(9) . . . . ? C023 C77 C013 O5 -166.2(7) . . . . ? N1 C77 C013 C015 -165.4(7) . . . . ? C023 C77 C013 C015 76.4(9) . . . . ? C022 O1 C014 C011 132.7(7) . . . . ? C022 O1 C014 C76 -103.5(8) . . . . ? C023 C011 C014 O1 168.8(7) . . . . ? C023 C011 C014 C76 50.4(11) . . . . ? C027 O3 C015 C76 -131.8(7) . . . . ? C027 O3 C015 C013 103.4(8) . . . . ? O5 C013 C015 O3 -57.3(8) . . . . ? C77 C013 C015 O3 63.1(9) . . . . ? O5 C013 C015 C76 -176.5(7) . . . . ? C77 C013 C015 C76 -56.1(10) . . . . ? O1 C014 C76 O20 -83.0(8) . . . . ? C011 C014 C76 O20 34.6(10) . . . . ? O1 C014 C76 C015 155.8(7) . . . . ? C011 C014 C76 C015 -86.6(9) . . . . ? O3 C015 C76 O20 -178.9(6) . . . . ? C013 C015 C76 O20 -59.2(9) . . . . ? O3 C015 C76 C014 -53.4(9) . . . . ? C013 C015 C76 C014 66.3(10) . . . . ? C025 O10 C017 C021 -68.0(10) . . . . ? C025 O10 C017 C028 174.0(7) . . . . ? C025 O10 C017 C019 57.5(10) . . . . ? C013 O5 C018 O6 2.5(12) . . . . ? C013 O5 C018 C026 -177.1(6) . . . . ? C014 O1 C022 O2 0.5(12) . . . . ? C014 O1 C022 C020 179.9(7) . . . . ? N1 C77 C023 C011 160.3(7) . . . . ? C013 C77 C023 C011 -80.2(9) . . . . ? C014 C011 C023 C77 24.5(12) . . . . ? C77 N1 C025 O8 12.3(13) . . . . ? C77 N1 C025 O10 -169.6(7) . . . . ? C017 O10 C025 O8 8.5(12) . . . . ? C017 O10 C025 N1 -169.7(7) . . . . ? C015 O3 C027 O4 4.6(12) . . . . ? C015 O3 C027 C024 -173.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 46.08 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 1.095 _refine_diff_density_min -0.599 _refine_diff_density_rms 0.180 # Attachment '- 20isomer.CIF' data_eg193 _database_code_depnum_ccdc_archive 'CCDC 787049' #TrackingRef '- 20isomer.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H29 N O9' _chemical_formula_weight 403.42 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' N N 0.0311 0.0180 '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 orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.652(3) _cell_length_b 10.174(2) _cell_length_c 28.070(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4469.7(15) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.814 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9231 _exptl_absorpt_correction_T_max 0.9760 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _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 14661 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 49.11 _reflns_number_total 2079 _reflns_number_gt 1691 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0421P)^2^+9.7491P] 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 SHELXL _refine_ls_extinction_coef 0.00004(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2079 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1310 _refine_ls_wR_factor_gt 0.1226 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 O4 O 0.26826(18) 0.2659(3) 0.09240(10) 0.0366(8) Uani 1 1 d . . . O1 O 0.13863(19) 0.5693(3) 0.01767(10) 0.0416(8) Uani 1 1 d . . . H1 H 0.1253 0.5901 0.0457 0.062 Uiso 1 1 calc R . . O2 O 0.12521(17) 0.2692(3) -0.05158(9) 0.0305(7) Uani 1 1 d . . . O3 O 0.09970(19) 0.3441(3) 0.08834(9) 0.0391(8) Uani 1 1 d . . . O6 O 0.29624(19) 0.4387(3) -0.17613(10) 0.0407(8) Uani 1 1 d . . . C006 C 0.1428(3) 0.4068(4) -0.04156(14) 0.0296(11) Uani 1 1 d . . . H006 H 0.1076 0.4624 -0.0635 0.036 Uiso 1 1 calc R . . O7 O -0.0096(2) 0.3185(3) -0.07274(11) 0.0441(9) Uani 1 1 d . . . N1 N 0.2531(2) 0.3959(3) -0.10329(12) 0.0331(9) Uani 1 1 d . . . H1A H 0.2567 0.3131 -0.1121 0.040 Uiso 1 1 calc R . . O5 O 0.2452(2) 0.6055(3) -0.13006(10) 0.0441(9) Uani 1 1 d . . . O8 O 0.0140(2) 0.1981(3) 0.05228(14) 0.0575(10) Uani 1 1 d . . . O9 O 0.3431(2) 0.3932(4) 0.14238(11) 0.0561(10) Uani 1 1 d . . . C012 C 0.1166(3) 0.4358(4) 0.00942(14) 0.0305(11) Uani 1 1 d . . . H012 H 0.0530 0.4282 0.0114 0.037 Uiso 1 1 calc R . . C013 C 0.1549(2) 0.3438(4) 0.04639(14) 0.0302(11) Uani 1 1 d . . . H013 H 0.1577 0.2528 0.0330 0.036 Uiso 1 1 calc R . . C014 C 0.2417(3) 0.3817(4) 0.06534(14) 0.0326(11) Uani 1 1 d . . . H014 H 0.2356 0.4581 0.0875 0.039 Uiso 1 1 calc R . . C015 C 0.2368(3) 0.4270(4) -0.05337(13) 0.0289(11) Uani 1 1 d . . . H015 H 0.2490 0.5227 -0.0492 0.035 Uiso 1 1 calc R . . C016 C 0.3186(3) 0.2857(6) 0.13051(16) 0.0422(13) Uani 1 1 d . . . C017 C 0.2629(3) 0.4907(5) -0.13598(15) 0.0317(11) Uani 1 1 d . . . C018 C 0.0384(3) 0.0948(4) -0.07540(16) 0.0432(13) Uani 1 1 d . . . H01A H 0.0930 0.0520 -0.0681 0.065 Uiso 1 1 calc R . . H01B H 0.0235 0.0788 -0.1088 0.065 Uiso 1 1 calc R . . H01C H -0.0063 0.0587 -0.0547 0.065 Uiso 1 1 calc R . . C019 C 0.3101(4) 0.5193(5) -0.21908(15) 0.0496(14) Uani 1 1 d . . . C020 C 0.3084(3) 0.4138(4) 0.02764(14) 0.0361(12) Uani 1 1 d . . . H02A H 0.3095 0.5105 0.0236 0.043 Uiso 1 1 calc R . . H02B H 0.3648 0.3875 0.0403 0.043 Uiso 1 1 calc R . . C021 C 0.2987(3) 0.3529(4) -0.02144(14) 0.0329(11) Uani 1 1 d . . . H02C H 0.2785 0.2612 -0.0178 0.039 Uiso 1 1 calc R . . H02D H 0.3554 0.3502 -0.0371 0.039 Uiso 1 1 calc R . . C022 C 0.0308(3) 0.2637(5) 0.08652(18) 0.0464(14) Uani 1 1 d . . . C023 C 0.0461(3) 0.2384(5) -0.06704(14) 0.0332(12) Uani 1 1 d . . . C024 C 0.3396(3) 0.1603(5) 0.15485(16) 0.0538(14) Uani 1 1 d . . . H02E H 0.3112 0.0874 0.1384 0.081 Uiso 1 1 calc R . . H02F H 0.3199 0.1640 0.1880 0.081 Uiso 1 1 calc R . . H02G H 0.4016 0.1466 0.1543 0.081 Uiso 1 1 calc R . . C025 C 0.3501(4) 0.4229(5) -0.25326(17) 0.0660(16) Uani 1 1 d . . . H02H H 0.4055 0.3942 -0.2408 0.099 Uiso 1 1 calc R . . H02I H 0.3584 0.4654 -0.2843 0.099 Uiso 1 1 calc R . . H02J H 0.3125 0.3466 -0.2570 0.099 Uiso 1 1 calc R . . C026 C -0.0200(4) 0.2707(6) 0.13138(19) 0.0770(18) Uani 1 1 d . . . H02K H 0.0080 0.3308 0.1538 0.116 Uiso 1 1 calc R . . H02L H -0.0237 0.1830 0.1456 0.116 Uiso 1 1 calc R . . H02M H -0.0776 0.3029 0.1242 0.116 Uiso 1 1 calc R . . C027 C 0.2242(4) 0.5659(5) -0.23697(17) 0.0742(18) Uani 1 1 d . . . H02N H 0.1875 0.4898 -0.2432 0.111 Uiso 1 1 calc R . . H02O H 0.2319 0.6162 -0.2664 0.111 Uiso 1 1 calc R . . H02P H 0.1974 0.6220 -0.2128 0.111 Uiso 1 1 calc R . . C028 C 0.3704(4) 0.6320(5) -0.20833(19) 0.086(2) Uani 1 1 d . . . H02Q H 0.4250 0.5970 -0.1968 0.129 Uiso 1 1 calc R . . H02R H 0.3452 0.6886 -0.1838 0.129 Uiso 1 1 calc R . . H02S H 0.3801 0.6833 -0.2374 0.129 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 O4 0.0361(19) 0.038(2) 0.0358(17) -0.0012(15) -0.0053(15) 0.0015(16) O1 0.051(2) 0.026(2) 0.0477(19) -0.0044(14) 0.0105(15) -0.0018(16) O2 0.0251(19) 0.0246(19) 0.0416(17) -0.0025(14) -0.0011(13) 0.0015(15) O3 0.0317(19) 0.042(2) 0.0430(19) 0.0009(15) 0.0069(14) -0.0077(18) O6 0.056(2) 0.0300(18) 0.0358(19) 0.0051(16) 0.0033(16) 0.0024(16) C006 0.032(3) 0.018(3) 0.039(3) -0.001(2) -0.003(2) 0.007(2) O7 0.030(2) 0.044(2) 0.058(2) -0.0057(16) -0.0049(15) 0.0122(19) N1 0.043(2) 0.019(2) 0.037(2) -0.001(2) 0.0059(18) -0.0007(18) O5 0.069(2) 0.019(2) 0.0433(19) 0.0006(16) -0.0049(17) 0.0039(18) O8 0.043(2) 0.057(2) 0.073(3) 0.002(2) -0.0005(19) -0.0172(19) O9 0.064(3) 0.056(2) 0.048(2) -0.0154(19) -0.0138(17) 0.000(2) C012 0.028(3) 0.020(3) 0.043(3) -0.002(2) 0.004(2) -0.001(2) C013 0.025(3) 0.028(3) 0.037(3) -0.001(2) 0.007(2) -0.002(2) C014 0.033(3) 0.025(3) 0.040(3) -0.002(2) 0.001(2) -0.002(2) C015 0.029(3) 0.019(3) 0.039(3) -0.004(2) 0.002(2) 0.003(2) C016 0.041(3) 0.054(4) 0.031(3) -0.008(3) 0.003(2) 0.001(3) C017 0.031(3) 0.030(3) 0.035(3) -0.001(3) -0.005(2) -0.004(2) C018 0.028(3) 0.040(3) 0.062(3) -0.008(2) -0.002(2) -0.002(2) C019 0.077(4) 0.037(3) 0.035(3) 0.012(3) 0.003(3) -0.002(3) C020 0.026(3) 0.037(3) 0.046(3) 0.001(2) -0.003(2) -0.005(2) C021 0.026(3) 0.027(3) 0.045(3) 0.000(2) 0.008(2) 0.001(2) C022 0.037(3) 0.053(4) 0.049(3) 0.011(3) 0.002(3) -0.003(3) C023 0.028(3) 0.037(4) 0.034(3) -0.004(2) 0.004(2) -0.004(3) C024 0.061(4) 0.064(4) 0.036(3) 0.007(3) -0.005(2) 0.004(3) C025 0.094(4) 0.058(4) 0.046(3) 0.006(3) 0.015(3) 0.008(3) C026 0.055(4) 0.101(5) 0.075(4) 0.013(4) 0.022(3) -0.019(4) C027 0.112(5) 0.067(4) 0.044(3) 0.003(3) -0.010(3) 0.026(4) C028 0.131(6) 0.063(4) 0.064(4) 0.010(3) 0.022(4) -0.042(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 O4 C016 1.344(5) . ? O4 C014 1.462(5) . ? O1 C012 1.420(4) . ? O2 C023 1.348(5) . ? O2 C006 1.454(5) . ? O3 C022 1.354(6) . ? O3 C013 1.461(5) . ? O6 C017 1.350(5) . ? O6 C019 1.474(5) . ? C006 C012 1.517(5) . ? C006 C015 1.522(6) . ? O7 C023 1.205(5) . ? N1 C017 1.339(5) . ? N1 C015 1.459(5) . ? O5 C017 1.212(5) . ? O8 C022 1.200(5) . ? O9 C016 1.205(5) . ? C012 C013 1.521(6) . ? C013 C014 1.509(6) . ? C014 C020 1.521(6) . ? C015 C021 1.520(5) . ? C016 C024 1.485(7) . ? C018 C023 1.485(6) . ? C019 C025 1.508(6) . ? C019 C027 1.512(7) . ? C019 C028 1.515(7) . ? C020 C021 1.518(5) . ? C022 C026 1.491(7) . ? 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 C016 O4 C014 117.3(3) . . ? C023 O2 C006 117.4(3) . . ? C022 O3 C013 116.1(3) . . ? C017 O6 C019 121.5(4) . . ? O2 C006 C012 108.6(3) . . ? O2 C006 C015 105.7(3) . . ? C012 C006 C015 116.1(3) . . ? C017 N1 C015 121.5(3) . . ? O1 C012 C006 105.9(3) . . ? O1 C012 C013 112.4(3) . . ? C006 C012 C013 114.7(3) . . ? O3 C013 C014 104.4(3) . . ? O3 C013 C012 108.4(3) . . ? C014 C013 C012 116.0(3) . . ? O4 C014 C013 103.5(3) . . ? O4 C014 C020 109.9(3) . . ? C013 C014 C020 115.3(3) . . ? N1 C015 C021 110.3(3) . . ? N1 C015 C006 110.5(3) . . ? C021 C015 C006 114.9(3) . . ? O9 C016 O4 122.9(4) . . ? O9 C016 C024 125.6(4) . . ? O4 C016 C024 111.5(5) . . ? O5 C017 N1 125.0(4) . . ? O5 C017 O6 125.4(4) . . ? N1 C017 O6 109.5(4) . . ? O6 C019 C025 102.7(4) . . ? O6 C019 C027 108.3(4) . . ? C025 C019 C027 111.2(4) . . ? O6 C019 C028 110.5(4) . . ? C025 C019 C028 111.1(5) . . ? C027 C019 C028 112.5(4) . . ? C021 C020 C014 118.4(3) . . ? C020 C021 C015 113.3(3) . . ? O8 C022 O3 122.8(4) . . ? O8 C022 C026 125.9(5) . . ? O3 C022 C026 111.3(5) . . ? O7 C023 O2 123.4(4) . . ? O7 C023 C018 125.9(4) . . ? O2 C023 C018 110.7(4) . . ? 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 C023 O2 C006 C012 86.9(4) . . . . ? C023 O2 C006 C015 -147.9(3) . . . . ? O2 C006 C012 O1 177.6(3) . . . . ? C015 C006 C012 O1 58.7(4) . . . . ? O2 C006 C012 C013 52.9(5) . . . . ? C015 C006 C012 C013 -65.9(5) . . . . ? C022 O3 C013 C014 -153.0(4) . . . . ? C022 O3 C013 C012 82.8(4) . . . . ? O1 C012 C013 O3 82.8(4) . . . . ? C006 C012 C013 O3 -156.1(3) . . . . ? O1 C012 C013 C014 -34.2(5) . . . . ? C006 C012 C013 C014 86.9(4) . . . . ? C016 O4 C014 C013 -148.9(3) . . . . ? C016 O4 C014 C020 87.5(4) . . . . ? O3 C013 C014 O4 71.0(4) . . . . ? C012 C013 C014 O4 -169.8(3) . . . . ? O3 C013 C014 C020 -169.0(3) . . . . ? C012 C013 C014 C020 -49.9(5) . . . . ? C017 N1 C015 C021 -129.3(4) . . . . ? C017 N1 C015 C006 102.5(4) . . . . ? O2 C006 C015 N1 59.7(4) . . . . ? C012 C006 C015 N1 -179.9(3) . . . . ? O2 C006 C015 C021 -65.9(4) . . . . ? C012 C006 C015 C021 54.5(5) . . . . ? C014 O4 C016 O9 -1.2(6) . . . . ? C014 O4 C016 C024 179.3(3) . . . . ? C015 N1 C017 O5 -13.2(6) . . . . ? C015 N1 C017 O6 166.0(3) . . . . ? C019 O6 C017 O5 -3.7(6) . . . . ? C019 O6 C017 N1 177.1(4) . . . . ? C017 O6 C019 C025 178.2(4) . . . . ? C017 O6 C019 C027 -64.1(5) . . . . ? C017 O6 C019 C028 59.6(6) . . . . ? O4 C014 C020 C021 90.6(4) . . . . ? C013 C014 C020 C021 -25.7(6) . . . . ? C014 C020 C021 C015 82.3(5) . . . . ? N1 C015 C021 C020 159.2(3) . . . . ? C006 C015 C021 C020 -75.2(4) . . . . ? C013 O3 C022 O8 -1.9(6) . . . . ? C013 O3 C022 C026 179.2(4) . . . . ? C006 O2 C023 O7 -0.1(5) . . . . ? C006 O2 C023 C018 -179.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 49.11 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.350 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.045