data_global #data_New_Global_Publ_Block _audit_creation_method ; manual editing of the CIF file created by SHELXTL Ver. 6.10 and processed with modiCIfer-09152005. ; # 1. SUBMISSION DETAILS _publ_contact_author_name ; Guzei, Ilia A. ; _publ_contact_author_address ; Department of Chemistry University of Wisconsin-Madison 1101 University Ave Madison, WI 53706 USA ; _publ_contact_author_phone '608-263-4694' _publ_contact_author_fax '608-262-0381' _publ_contact_author_email iguzei@chem.wisc.edu _publ_contact_letter ; Please consider this CIF submission for publication in ; _publ_requested_journal ; ; _publ_requested_category FA # FA 'Full article' # FI 'Full submission - inorganic (Acta C)' # FO 'Full submission - organic (Acta C)' # FM 'Full submission - metal-organic (Acta C)' # CI 'CIF-access paper - inorganic (Acta C)' # CO 'CIF-access paper - organic (Acta C)' # CM 'CIF-access paper - metal-organic (Acta C)' # 2. TITLE AND AUTHOR LIST _publ_section_title ; Title (type here to add) ; loop_ _publ_author_name _publ_author_address 'Guzei, Ilia A.' ; Department of Chemistry University of Wisconsin-Madison 1101 University Ave Madison, WI 53706 USA ; '' ; Department of Chemistry University of Wisconsin-Madison 1101 University Ave Madison, WI 53706 USA ; _publ_section_synopsis . _publ_section_abstract ; (type here to add abstract) ; _publ_section_comment ; (type here to add) ; _publ_section_references ; Allen, F. H. (2002). Acta Cryst. B58, 380--388. Bruker-AXS. (2003). SADABS (Version 2.05), SAINT (Version 6.22), SHELXTL (Version 6.10), and SMART (Version 5.622). Bruker-AXS Inc., Madison, WI, USA. Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389--397. Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1358--1367. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A. Jr, Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., et al. (2004). Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford, CT, USA. ; _publ_section_acknowledgements ; We thank the National Science Foundation for financial support. The manuscript was prepared with the beta test version 1.0.0. of program publCIF to be released by the IUCr and Ilia A. Guzei's program modiCIFer to be released by University of Wisconsin-Madison. ; _publ_section_figure_captions ; Figure 1. Molecular structure of (I). The thermal ellipsoids are shown at 50% probability level. ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; All H-atoms were placed in idealized locations and refined as riding with appropriate thermal displacement coefficients U~iso~(H) = 1.2 or 1.5 times U~eq~(bearing atom). Default effective X---H distances for T = -173.0 C AFIX m = C1 C2 C3 C4 4[N] 3[N] 15[B] 8[O] 9 9[N] 16 d(X---H) = 1.00 0.99 0.98 0.95 0.88 0.91 1.12 0.84 0.95 0.88 0.95 ; #3. data data_raines09 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H19 N O5' _chemical_formula_weight 245.27 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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall 'P 2yb ' _symmetry_int_tables_number 4 _chemical_absolute_configuration 'syn' # Options are 'rm', 'ad', 'rmad', 'syn', 'unk' or '.' # # rm : absolute configuration established by the structure determination # of a compound containing a chiral reference molecule of known # absolute configuration. # ad : absolute configuration established by anomalous dispersion effects # in diffraction measurements on the crystal. # rmad : absolute configuration established by the structure determination # of a compound containing a chiral reference molecule of known # absolute configuration and confirmed by anomalous dispersion # effects in diffraction measurements on the crystal. # syn : absolute configuration has not been established by anomalous # dispersion effects in diffraction measurements on the crystal. # The enantiomer has been assigned by reference to an unchanging # chiral centre in the synthetic procedure. # unk : absolute configuration is unknown, there being no firm chemical # evidence for its assignment to hand and it having not been # established by anomalous dispersion effects in diffraction # measurements on the crystal. An arbitrary choice of enantiomer # has been made. # . : inapplicable. loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.3770(16) _cell_length_b 9.552(2) _cell_length_c 10.158(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.190(3) _cell_angle_gamma 90.00 _cell_volume 618.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 6766 _cell_measurement_theta_min 2.9272 _cell_measurement_theta_max 29.0060 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details ; SADABS (Bruker-AXS, 2003) ; _exptl_absorpt_correction_T_min 0.9481 _exptl_absorpt_correction_T_max 0.9897 _exptl_special_details ; ? ; _diffrn_ambient_temperature 105(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD-1000 area detector' _diffrn_measurement_method '0.30\% \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10263 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 29.02 _reflns_number_total 1727 _reflns_number_gt 1695 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART Ver. 5.622 (Bruker-AXS, 2003)' _computing_cell_refinement 'SAINT Ver. 6.22 (Bruker-AXS, 2003)' _computing_data_reduction 'SAINT Ver. 6.22' _computing_structure_solution 'SHELXTL Ver. 6.10 (Bruker-AXS, 2003)' _computing_structure_refinement 'SHELXTL Ver. 6.10' _computing_molecular_graphics 'SHELXTL Ver. 6.10' _computing_publication_material 'SHELXTL Ver. 6.10' _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^)+(0.0494P)^2^+0.0656P] 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 undef _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(12) _refine_ls_number_reflns 1727 _refine_ls_number_parameters 160 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0312 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0771 _refine_ls_wR_factor_gt 0.0767 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _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 0.4942(2) 0.29380(18) 0.75241(15) 0.0186(3) Uani 1 1 d . . . O2 O 0.6991(3) 0.16405(15) 0.89234(15) 0.0190(3) Uani 1 1 d . . . O3 O 1.1034(2) 0.20326(17) 0.72572(17) 0.0201(3) Uani 1 1 d . . . H3 H 1.2301 0.2265 0.7313 0.024 Uiso 1 1 calc R . . O4 O 1.2392(2) -0.00995(17) 0.69011(16) 0.0206(3) Uani 1 1 d . . . O5 O 0.9609(3) 0.10455(16) 0.43245(15) 0.0188(3) Uani 1 1 d . . . N1 N 0.7097(3) 0.12405(19) 0.67775(17) 0.0161(3) Uani 1 1 d . . . C1 C 0.8634(3) 0.0134(2) 0.6960(2) 0.0152(3) Uani 1 1 d . . . H1 H 0.8313 -0.0402 0.7780 0.018 Uiso 1 1 calc R . . C2 C 0.8237(4) -0.0786(2) 0.5753(2) 0.0185(4) Uani 1 1 d . . . H2A H 0.7033 -0.1423 0.5893 0.022 Uiso 1 1 calc R . . H2B H 0.9492 -0.1346 0.5527 0.022 Uiso 1 1 calc R . . C3 C 0.7754(3) 0.0307(2) 0.4690(2) 0.0181(4) Uani 1 1 d . . . H3A H 0.7029 -0.0115 0.3910 0.022 Uiso 1 1 calc R . . C4 C 0.6376(3) 0.1358(2) 0.5397(2) 0.0184(4) Uani 1 1 d . . . H4A H 0.6595 0.2316 0.5053 0.022 Uiso 1 1 calc R . . H4B H 0.4875 0.1110 0.5313 0.022 Uiso 1 1 calc R . . C5 C 0.6260(3) 0.2018(2) 0.7731(2) 0.0162(4) Uani 1 1 d . . . C6 C 0.6784(4) 0.2581(2) 1.0070(2) 0.0180(4) Uani 1 1 d . . . C7 C 0.7881(4) 0.3955(3) 0.9775(2) 0.0261(5) Uani 1 1 d . . . H7A H 0.7189 0.4414 0.9028 0.039 Uiso 1 1 calc R . . H7B H 0.9352 0.3772 0.9557 0.039 Uiso 1 1 calc R . . H7C H 0.7811 0.4564 1.0549 0.039 Uiso 1 1 calc R . . C8 C 0.4496(4) 0.2788(3) 1.0445(3) 0.0298(5) Uani 1 1 d . . . H8A H 0.3776 0.1881 1.0441 0.045 Uiso 1 1 calc R . . H8B H 0.3821 0.3415 0.9808 0.045 Uiso 1 1 calc R . . H8C H 0.4417 0.3200 1.1327 0.045 Uiso 1 1 calc R . . C9 C 0.7954(5) 0.1775(3) 1.1144(2) 0.0281(5) Uani 1 1 d . . . H9A H 0.9392 0.1589 1.0856 0.042 Uiso 1 1 calc R . . H9B H 0.7236 0.0886 1.1312 0.042 Uiso 1 1 calc R . . H9C H 0.7984 0.2333 1.1953 0.042 Uiso 1 1 calc R . . C10 C 1.0898(3) 0.0674(2) 0.7011(2) 0.0150(4) Uani 1 1 d . . . C11 C 1.1055(4) 0.0226(3) 0.3600(2) 0.0232(4) Uani 1 1 d . . . H11A H 1.0317 -0.0258 0.2884 0.035 Uiso 1 1 calc R . . H11B H 1.1707 -0.0466 0.4184 0.035 Uiso 1 1 calc R . . H11C H 1.2142 0.0834 0.3230 0.035 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0158(6) 0.0161(6) 0.0239(7) -0.0012(6) -0.0020(6) 0.0007(6) O2 0.0215(7) 0.0177(7) 0.0178(7) -0.0025(5) 0.0000(5) 0.0039(6) O3 0.0140(7) 0.0160(6) 0.0302(8) -0.0035(6) -0.0013(6) 0.0005(6) O4 0.0178(7) 0.0179(7) 0.0263(8) 0.0024(6) 0.0034(6) 0.0041(6) O5 0.0218(7) 0.0158(7) 0.0189(6) -0.0002(6) 0.0022(6) -0.0017(6) N1 0.0129(7) 0.0173(8) 0.0181(8) -0.0009(6) -0.0015(6) 0.0001(7) C1 0.0179(8) 0.0122(8) 0.0154(8) 0.0008(7) 0.0017(7) -0.0001(7) C2 0.0234(11) 0.0116(9) 0.0205(9) -0.0007(7) 0.0005(8) -0.0023(8) C3 0.0205(9) 0.0164(8) 0.0176(9) -0.0023(7) -0.0018(8) -0.0022(8) C4 0.0183(8) 0.0222(10) 0.0146(9) -0.0015(7) -0.0025(7) 0.0012(8) C5 0.0127(8) 0.0162(8) 0.0196(9) -0.0022(7) 0.0018(7) -0.0039(7) C6 0.0222(10) 0.0163(9) 0.0155(9) -0.0012(7) 0.0030(7) 0.0005(8) C7 0.0365(13) 0.0209(10) 0.0208(10) -0.0006(9) -0.0012(9) -0.0081(11) C8 0.0259(11) 0.0316(12) 0.0318(11) -0.0002(10) 0.0117(10) 0.0055(10) C9 0.0393(12) 0.0264(11) 0.0187(9) 0.0007(9) -0.0023(9) 0.0072(11) C10 0.0172(9) 0.0155(8) 0.0124(8) 0.0023(7) -0.0020(7) 0.0004(8) C11 0.0263(11) 0.0227(10) 0.0206(10) -0.0010(8) 0.0043(8) 0.0005(9) _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 C5 1.234(3) . ? O2 C5 1.346(3) . ? O2 C6 1.477(3) . ? O3 C10 1.324(3) . ? O3 H3 0.8400 . ? O4 C10 1.211(3) . ? O5 C11 1.418(3) . ? O5 C3 1.427(3) . ? N1 C5 1.333(3) . ? N1 C1 1.453(3) . ? N1 C4 1.478(3) . ? C1 C2 1.529(3) . ? C1 C10 1.534(3) . ? C1 H1 1.0000 . ? C2 C3 1.533(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.517(3) . ? C3 H3A 1.0000 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C6 C7 1.517(3) . ? C6 C8 1.522(3) . ? C6 C9 1.528(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? 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 C6 121.02(16) . . ? C10 O3 H3 109.5 . . ? C11 O5 C3 113.75(17) . . ? C5 N1 C1 125.75(17) . . ? C5 N1 C4 121.51(18) . . ? C1 N1 C4 112.55(16) . . ? N1 C1 C2 101.92(16) . . ? N1 C1 C10 113.21(16) . . ? C2 C1 C10 111.95(17) . . ? N1 C1 H1 109.8 . . ? C2 C1 H1 109.8 . . ? C10 C1 H1 109.8 . . ? C1 C2 C3 101.86(16) . . ? C1 C2 H2A 111.4 . . ? C3 C2 H2A 111.4 . . ? C1 C2 H2B 111.4 . . ? C3 C2 H2B 111.4 . . ? H2A C2 H2B 109.3 . . ? O5 C3 C4 106.11(17) . . ? O5 C3 C2 110.81(17) . . ? C4 C3 C2 103.41(17) . . ? O5 C3 H3A 112.0 . . ? C4 C3 H3A 112.0 . . ? C2 C3 H3A 112.0 . . ? N1 C4 C3 102.75(17) . . ? N1 C4 H4A 111.2 . . ? C3 C4 H4A 111.2 . . ? N1 C4 H4B 111.2 . . ? C3 C4 H4B 111.2 . . ? H4A C4 H4B 109.1 . . ? O1 C5 N1 123.20(19) . . ? O1 C5 O2 125.29(19) . . ? N1 C5 O2 111.49(18) . . ? O2 C6 C7 109.14(17) . . ? O2 C6 C8 111.39(19) . . ? C7 C6 C8 112.3(2) . . ? O2 C6 C9 102.24(17) . . ? C7 C6 C9 110.6(2) . . ? C8 C6 C9 110.7(2) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O4 C10 O3 124.38(19) . . ? O4 C10 C1 122.14(18) . . ? O3 C10 C1 113.37(17) . . ? O5 C11 H11A 109.5 . . ? O5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 C5 N1 C1 C2 154.43(19) . . . . ? C4 N1 C1 C2 -20.6(2) . . . . ? C5 N1 C1 C10 -85.2(2) . . . . ? C4 N1 C1 C10 99.8(2) . . . . ? N1 C1 C2 C3 37.32(19) . . . . ? C10 C1 C2 C3 -84.0(2) . . . . ? C11 O5 C3 C4 -177.70(18) . . . . ? C11 O5 C3 C2 70.7(2) . . . . ? C1 C2 C3 O5 71.9(2) . . . . ? C1 C2 C3 C4 -41.4(2) . . . . ? C5 N1 C4 C3 179.68(18) . . . . ? C1 N1 C4 C3 -5.1(2) . . . . ? O5 C3 C4 N1 -88.01(19) . . . . ? C2 C3 C4 N1 28.7(2) . . . . ? C1 N1 C5 O1 -179.29(19) . . . . ? C4 N1 C5 O1 -4.7(3) . . . . ? C1 N1 C5 O2 -1.0(3) . . . . ? C4 N1 C5 O2 173.58(18) . . . . ? C6 O2 C5 O1 -19.5(3) . . . . ? C6 O2 C5 N1 162.30(18) . . . . ? C5 O2 C6 C7 -58.8(2) . . . . ? C5 O2 C6 C8 65.8(3) . . . . ? C5 O2 C6 C9 -175.96(19) . . . . ? N1 C1 C10 O4 -165.41(18) . . . . ? C2 C1 C10 O4 -50.9(3) . . . . ? N1 C1 C10 O3 18.2(2) . . . . ? C2 C1 C10 O3 132.72(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O1 0.84 1.81 2.651(2) 173.7 1_655 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 29.02 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.228 _refine_diff_density_min -0.124 _refine_diff_density_rms 0.040 # File processed with modiCIFer Dec. 16,2005. I.A.Guzei, UW-Madison. # Formatted by publCIF