data_ba26nas _audit_creation_method SHELXL-97 _audit_update_record ; ? ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H24 B N O5' _chemical_formula_sum 'C16 H24 B N O5' _chemical_formula_structural ? _chemical_formula_weight 321.17 _chemical_absolute_configuration syn _chemical_formula_iupac ? _chemical_formula_analytical ? _chemical_compound_source ? 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 0.0000 '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' 'B' 'B' 0.0013 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0000 '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) ' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.2683(4) _cell_length_b 10.2312(6) _cell_length_c 10.5809(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.780(3) _cell_angle_gamma 90.00 _cell_volume 785.12(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8809 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 27.13 _exptl_crystal_description 'acicular' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.738 _exptl_crystal_size_mid 0.183 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_crystal_id ba26nas _exptl_crystal_preparation ; The data crystal was mounted using oil (Parantone-N, Exxon) to a 0.3 mm cryo-loop (Hampton Research). ; _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.9615 _exptl_absorpt_correction_T_max 0.9954 _exptl_absorpt_process_details 'SHELXTL/XPREP V2005/2 (Bruker, 2005)' _exptl_special_details ; One distinct cell was identified using APEX2 (Bruker, 2004). Eight frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2005) then corrected for absorption by integration using SHELXTL/XPREP V2005/2 (Bruker, 2005) before using SADABS (Bruker, 2005) to sort, merge, and scale the combined data. No decay correction was applied. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id ba26nas _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type ? _diffrn_measurement_device 'Bruker Kappa/ApexII CCD' _diffrn_measurement_method 'profile data from \f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16857 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 27.14 _reflns_number_total 1833 _reflns_number_gt 1749 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 V2.0-1 (Bruker, 2004)' _computing_cell_refinement 'SAINT V7.23A (Bruker, 2005)' _computing_data_reduction ; SAINT V7.23A, XPREP V2005/2, SADABS V2007/4, TWINABS V2007/5 (Bruker, 2005 & 2007) ; _computing_structure_solution 'SHELXTL V6.12 (Bruker, 2005)' _computing_structure_refinement 'SHELXTL V6.12 (Bruker, 2005)' _computing_molecular_graphics ; SHELXTL V6.12 (Bruker, 2005), CrystalMaker v2.1.3 (CrystalMaker, 1994) ; _computing_publication_material 'XCIF V6.12 (Bruker, 2005)' _refine_special_details ; Structure was phased by direct methods (Sheldrick, 2008). Systematic conditions suggested the ambiguous space group. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F^2^. The highest peaks in the final difference Fourier map were in the vicinity of atoms C9 and C10; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed little dependence on amplitude and some dependence on resolution. The acicular parent crystals were extremely difficult to cut without damaging the crystal parallel to the b-axis. The data crystal was much longer than ideal; however, the mosaicity of shorter crystals damaged by the cutting process was too broad for data collection. ; _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^)+(0.0583P)^2^+0.0737P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack (1983), merged Friedels' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 1833 _refine_ls_number_parameters 211 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.050 _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 B1 B 0.1352(3) 1.13247(19) 0.41469(18) 0.0139(4) Uani 1 1 d . . . N1 N 0.14954(19) 0.97194(14) 0.39697(13) 0.0126(3) Uani 1 1 d . . . O1 O 0.15070(17) 1.14296(13) 0.55464(11) 0.0168(3) Uani 1 1 d . . . O2 O 0.21310(19) 1.01926(15) 0.72660(12) 0.0239(3) Uani 1 1 d . . . O3 O -0.32754(17) 1.05673(15) 0.34960(13) 0.0237(3) Uani 1 1 d . . . O4 O -0.05699(16) 1.16152(13) 0.37108(12) 0.0160(3) Uani 1 1 d . . . O5 O 0.2793(2) 1.35781(14) 0.38056(13) 0.0236(3) Uani 1 1 d . . . C1 C 0.2032(2) 1.03266(19) 0.61395(17) 0.0175(4) Uani 1 1 d . . . C2 C 0.2525(2) 0.93103(18) 0.51805(16) 0.0155(3) Uani 1 1 d . . . H2A H 0.3871 0.9301 0.5084 0.019 Uiso 1 1 calc R . . H2B H 0.2135 0.8429 0.5440 0.019 Uiso 1 1 calc R . . C3 C -0.0497(2) 0.93398(18) 0.39781(16) 0.0151(4) Uani 1 1 d . . . H3A H -0.0762 0.8983 0.4817 0.018 Uiso 1 1 calc R . . H3B H -0.0798 0.8663 0.3328 0.018 Uiso 1 1 calc R . . C4 C -0.1625(2) 1.05525(19) 0.36959(16) 0.0165(3) Uani 1 1 d . . . C5 C 0.2426(2) 0.92187(17) 0.28129(16) 0.0131(3) Uani 1 1 d . . . H5 H 0.3736 0.9521 0.2910 0.016 Uiso 1 1 calc R . . C6 C 0.2486(2) 0.76907(18) 0.27741(16) 0.0151(3) Uani 1 1 d . . . H6 H 0.1458 0.7361 0.3271 0.018 Uiso 1 1 calc R . . C7 C 0.2138(2) 0.71950(19) 0.14107(17) 0.0170(4) Uani 1 1 d . . . H7 H 0.2300 0.6231 0.1310 0.020 Uiso 1 1 calc R . . C8 C 0.3066(2) 0.80451(19) 0.03892(16) 0.0168(4) Uani 1 1 d . . . C9 C 0.1344(2) 0.89400(19) 0.04640(17) 0.0180(4) Uani 1 1 d . . . H9 H 0.0883 0.9350 -0.0355 0.022 Uiso 1 1 calc R . . C10 C 0.1562(2) 0.98718(18) 0.15918(16) 0.0161(4) Uani 1 1 d . . . H10A H 0.0335 1.0225 0.1765 0.019 Uiso 1 1 calc R . . H10B H 0.2347 1.0616 0.1367 0.019 Uiso 1 1 calc R . . C11 C 0.4286(3) 0.7123(2) 0.33785(18) 0.0227(4) Uani 1 1 d . . . H11A H 0.4223 0.6167 0.3361 0.034 Uiso 1 1 calc R . . H11B H 0.4464 0.7423 0.4258 0.034 Uiso 1 1 calc R . . H11C H 0.5322 0.7417 0.2903 0.034 Uiso 1 1 calc R . . C12 C 0.0265(3) 0.7725(2) 0.08618(18) 0.0208(4) Uani 1 1 d . . . H12A H -0.0298 0.7210 0.0144 0.025 Uiso 1 1 calc R . . H12B H -0.0634 0.7901 0.1504 0.025 Uiso 1 1 calc R . . C13 C 0.4972(3) 0.8643(2) 0.06278(17) 0.0231(4) Uani 1 1 d . . . H13A H 0.5199 0.9261 -0.0052 0.035 Uiso 1 1 calc R . . H13B H 0.5904 0.7949 0.0647 0.035 Uiso 1 1 calc R . . H13C H 0.5043 0.9103 0.1442 0.035 Uiso 1 1 calc R . . C14 C 0.3050(3) 0.7314(2) -0.08732(18) 0.0234(4) Uani 1 1 d . . . H14A H 0.3227 0.7937 -0.1558 0.035 Uiso 1 1 calc R . . H14B H 0.1864 0.6868 -0.1032 0.035 Uiso 1 1 calc R . . H14C H 0.4048 0.6668 -0.0838 0.035 Uiso 1 1 calc R . . C15 C 0.2819(2) 1.21851(18) 0.34686(17) 0.0167(4) Uani 1 1 d . . . H15 H 0.4062 1.1783 0.3396 0.020 Uiso 1 1 calc R . . C16 C 0.2273(3) 1.3192(2) 0.25343(19) 0.0231(4) Uani 1 1 d . . . H16A H 0.3138 1.3392 0.1876 0.028 Uiso 1 1 calc R . . H16B H 0.0952 1.3250 0.2246 0.028 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 B1 0.0147(9) 0.0092(9) 0.0178(8) -0.0014(7) 0.0017(7) 0.0007(7) N1 0.0107(6) 0.0117(7) 0.0154(6) 0.0006(5) 0.0009(5) 0.0007(5) O1 0.0185(6) 0.0145(6) 0.0178(6) -0.0011(5) 0.0029(5) -0.0014(5) O2 0.0305(7) 0.0235(7) 0.0179(6) 0.0009(5) 0.0027(5) -0.0029(6) O3 0.0116(6) 0.0243(7) 0.0349(7) 0.0015(6) 0.0004(5) 0.0012(6) O4 0.0125(6) 0.0134(6) 0.0224(6) 0.0000(5) 0.0026(5) 0.0025(5) O5 0.0302(7) 0.0152(7) 0.0264(7) -0.0022(6) 0.0081(5) -0.0040(6) C1 0.0153(7) 0.0175(9) 0.0197(8) -0.0002(7) 0.0009(6) -0.0042(7) C2 0.0151(8) 0.0155(8) 0.0156(7) 0.0027(7) -0.0008(6) 0.0011(7) C3 0.0114(8) 0.0127(8) 0.0212(8) 0.0000(7) 0.0022(6) -0.0011(6) C4 0.0147(7) 0.0159(9) 0.0191(8) -0.0003(7) 0.0028(6) 0.0012(7) C5 0.0111(7) 0.0121(8) 0.0160(8) -0.0012(6) 0.0014(6) 0.0007(6) C6 0.0140(8) 0.0122(8) 0.0191(8) 0.0008(7) 0.0009(6) 0.0014(6) C7 0.0181(8) 0.0126(9) 0.0203(8) -0.0026(7) 0.0010(6) 0.0002(7) C8 0.0160(8) 0.0169(9) 0.0176(8) -0.0026(7) 0.0011(6) 0.0007(7) C9 0.0192(8) 0.0172(9) 0.0171(7) -0.0008(7) -0.0019(6) 0.0037(7) C10 0.0193(8) 0.0119(9) 0.0171(8) -0.0005(7) 0.0010(6) 0.0038(7) C11 0.0239(9) 0.0196(10) 0.0238(9) -0.0016(7) -0.0038(7) 0.0107(8) C12 0.0167(8) 0.0226(10) 0.0226(8) -0.0046(8) -0.0024(6) -0.0022(8) C13 0.0197(8) 0.0261(11) 0.0241(8) -0.0074(8) 0.0064(7) -0.0032(8) C14 0.0281(9) 0.0209(10) 0.0211(9) -0.0059(8) 0.0019(7) 0.0003(8) C15 0.0164(8) 0.0119(8) 0.0220(8) -0.0023(7) 0.0031(6) 0.0000(7) C16 0.0258(10) 0.0194(10) 0.0246(9) 0.0056(8) 0.0058(7) -0.0018(8) _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 B1 O4 1.472(2) . ? B1 O1 1.482(2) . ? B1 C15 1.590(3) . ? B1 N1 1.657(2) . ? N1 C3 1.500(2) . ? N1 C2 1.500(2) . ? N1 C5 1.526(2) . ? O1 C1 1.335(2) . ? O2 C1 1.197(2) . ? O3 C4 1.205(2) . ? O4 C4 1.330(2) . ? O5 C16 1.429(2) . ? O5 C15 1.470(2) . ? C1 C2 1.512(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.506(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 C10 1.550(2) . ? C5 C6 1.565(2) . ? C5 H5 1.0000 . ? C6 C11 1.532(2) . ? C6 C7 1.534(2) . ? C6 H6 1.0000 . ? C7 C12 1.543(2) . ? C7 C8 1.573(3) . ? C7 H7 1.0000 . ? C8 C13 1.520(2) . ? C8 C14 1.530(2) . ? C8 C9 1.557(3) . ? C9 C10 1.527(2) . ? C9 C12 1.543(3) . ? C9 H9 1.0000 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.464(3) . ? C15 H15 1.0000 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? 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 O4 B1 O1 107.86(14) . . ? O4 B1 C15 113.42(15) . . ? O1 B1 C15 113.70(14) . . ? O4 B1 N1 103.30(14) . . ? O1 B1 N1 100.58(13) . . ? C15 B1 N1 116.65(15) . . ? C3 N1 C2 110.50(13) . . ? C3 N1 C5 113.40(13) . . ? C2 N1 C5 111.64(13) . . ? C3 N1 B1 100.84(13) . . ? C2 N1 B1 102.21(13) . . ? C5 N1 B1 117.27(13) . . ? C1 O1 B1 114.16(14) . . ? C4 O4 B1 111.90(14) . . ? C16 O5 C15 60.68(12) . . ? O2 C1 O1 124.16(18) . . ? O2 C1 C2 126.01(18) . . ? O1 C1 C2 109.81(14) . . ? N1 C2 C1 104.72(14) . . ? N1 C2 H2A 110.8 . . ? C1 C2 H2A 110.8 . . ? N1 C2 H2B 110.8 . . ? C1 C2 H2B 110.8 . . ? H2A C2 H2B 108.9 . . ? N1 C3 C4 107.36(14) . . ? N1 C3 H3A 110.2 . . ? C4 C3 H3A 110.2 . . ? N1 C3 H3B 110.2 . . ? C4 C3 H3B 110.2 . . ? H3A C3 H3B 108.5 . . ? O3 C4 O4 123.95(18) . . ? O3 C4 C3 124.60(18) . . ? O4 C4 C3 111.44(14) . . ? N1 C5 C10 110.31(13) . . ? N1 C5 C6 111.80(14) . . ? C10 C5 C6 114.79(14) . . ? N1 C5 H5 106.5 . . ? C10 C5 H5 106.5 . . ? C6 C5 H5 106.5 . . ? C11 C6 C7 110.52(14) . . ? C11 C6 C5 113.10(15) . . ? C7 C6 C5 110.60(14) . . ? C11 C6 H6 107.5 . . ? C7 C6 H6 107.5 . . ? C5 C6 H6 107.5 . . ? C6 C7 C12 108.93(14) . . ? C6 C7 C8 114.31(15) . . ? C12 C7 C8 87.41(14) . . ? C6 C7 H7 114.4 . . ? C12 C7 H7 114.4 . . ? C8 C7 H7 114.4 . . ? C13 C8 C14 107.23(15) . . ? C13 C8 C9 118.82(17) . . ? C14 C8 C9 111.82(15) . . ? C13 C8 C7 122.38(14) . . ? C14 C8 C7 110.50(15) . . ? C9 C8 C7 84.70(13) . . ? C10 C9 C12 108.54(14) . . ? C10 C9 C8 111.38(14) . . ? C12 C9 C8 87.99(14) . . ? C10 C9 H9 115.3 . . ? C12 C9 H9 115.3 . . ? C8 C9 H9 115.3 . . ? C9 C10 C5 113.42(15) . . ? C9 C10 H10A 108.9 . . ? C5 C10 H10A 108.9 . . ? C9 C10 H10B 108.9 . . ? C5 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 C7 86.22(13) . . ? C9 C12 H12A 114.3 . . ? C7 C12 H12A 114.3 . . ? C9 C12 H12B 114.3 . . ? C7 C12 H12B 114.3 . . ? H12A C12 H12B 111.4 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C8 C14 H14A 109.5 . . ? C8 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C8 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 O5 58.28(12) . . ? C16 C15 B1 122.30(16) . . ? O5 C15 B1 114.07(14) . . ? C16 C15 H15 116.3 . . ? O5 C15 H15 116.3 . . ? B1 C15 H15 116.3 . . ? O5 C16 C15 61.04(12) . . ? O5 C16 H16A 117.7 . . ? C15 C16 H16A 117.7 . . ? O5 C16 H16B 117.7 . . ? C15 C16 H16B 117.7 . . ? H16A C16 H16B 114.8 . . ? 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 O4 B1 N1 C3 -22.10(16) . . . . ? O1 B1 N1 C3 89.30(14) . . . . ? C15 B1 N1 C3 -147.25(14) . . . . ? O4 B1 N1 C2 -136.07(13) . . . . ? O1 B1 N1 C2 -24.68(16) . . . . ? C15 B1 N1 C2 98.78(16) . . . . ? O4 B1 N1 C5 101.52(15) . . . . ? O1 B1 N1 C5 -147.09(12) . . . . ? C15 B1 N1 C5 -23.6(2) . . . . ? O4 B1 O1 C1 119.56(16) . . . . ? C15 B1 O1 C1 -113.75(17) . . . . ? N1 B1 O1 C1 11.73(18) . . . . ? O1 B1 O4 C4 -87.56(17) . . . . ? C15 B1 O4 C4 145.58(15) . . . . ? N1 B1 O4 C4 18.36(18) . . . . ? B1 O1 C1 O2 -175.42(17) . . . . ? B1 O1 C1 C2 6.25(19) . . . . ? C3 N1 C2 C1 -78.11(17) . . . . ? C5 N1 C2 C1 154.69(13) . . . . ? B1 N1 C2 C1 28.53(16) . . . . ? O2 C1 C2 N1 158.25(18) . . . . ? O1 C1 C2 N1 -23.46(18) . . . . ? C2 N1 C3 C4 126.29(15) . . . . ? C5 N1 C3 C4 -107.50(16) . . . . ? B1 N1 C3 C4 18.74(17) . . . . ? B1 O4 C4 O3 172.32(17) . . . . ? B1 O4 C4 C3 -6.86(19) . . . . ? N1 C3 C4 O3 171.55(16) . . . . ? N1 C3 C4 O4 -9.27(19) . . . . ? C3 N1 C5 C10 65.30(18) . . . . ? C2 N1 C5 C10 -169.09(14) . . . . ? B1 N1 C5 C10 -51.67(18) . . . . ? C3 N1 C5 C6 -63.71(17) . . . . ? C2 N1 C5 C6 61.90(18) . . . . ? B1 N1 C5 C6 179.32(14) . . . . ? N1 C5 C6 C11 -93.91(17) . . . . ? C10 C5 C6 C11 139.47(15) . . . . ? N1 C5 C6 C7 141.52(13) . . . . ? C10 C5 C6 C7 14.9(2) . . . . ? C11 C6 C7 C12 176.87(16) . . . . ? C5 C6 C7 C12 -57.10(19) . . . . ? C11 C6 C7 C8 -87.25(19) . . . . ? C5 C6 C7 C8 38.8(2) . . . . ? C6 C7 C8 C13 38.6(2) . . . . ? C12 C7 C8 C13 148.23(18) . . . . ? C6 C7 C8 C14 166.32(15) . . . . ? C12 C7 C8 C14 -84.06(16) . . . . ? C6 C7 C8 C9 -82.34(16) . . . . ? C12 C7 C8 C9 27.28(12) . . . . ? C13 C8 C9 C10 -42.4(2) . . . . ? C14 C8 C9 C10 -168.14(16) . . . . ? C7 C8 C9 C10 81.88(16) . . . . ? C13 C8 C9 C12 -151.52(16) . . . . ? C14 C8 C9 C12 82.71(17) . . . . ? C7 C8 C9 C12 -27.27(12) . . . . ? C12 C9 C10 C5 53.65(19) . . . . ? C8 C9 C10 C5 -41.6(2) . . . . ? N1 C5 C10 C9 -141.11(15) . . . . ? C6 C5 C10 C9 -13.7(2) . . . . ? C10 C9 C12 C7 -84.11(15) . . . . ? C8 C9 C12 C7 27.79(12) . . . . ? C6 C7 C12 C9 87.35(16) . . . . ? C8 C7 C12 C9 -27.49(12) . . . . ? C16 O5 C15 B1 -114.33(17) . . . . ? O4 B1 C15 C16 1.9(2) . . . . ? O1 B1 C15 C16 -121.85(19) . . . . ? N1 B1 C15 C16 121.74(19) . . . . ? O4 B1 C15 O5 68.38(19) . . . . ? O1 B1 C15 O5 -55.3(2) . . . . ? N1 B1 C15 O5 -171.76(14) . . . . ? B1 C15 C16 O5 100.17(18) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.14 _diffrn_measured_fraction_theta_full 0.998 _diffrn_standards_number ? _diffrn_standards_decay_% ? _diffrn_standards_interval_time ? _refine_diff_density_max 0.294 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.040 _publ_requested_category O _publ_section_references ; Bruker (2004). APEX2. Bruker AXS, Inc., Madison, Wisconsin, USA. Bruker (2005). SAINT, SHELXTL, XCIF, XPREP. Bruker AXS, Inc., Madison, Wisconsin, USA. Bruker (2007). SADABS, TWINABS. Bruker AXS, Inc., Madison, Wisconsin, USA. CrystalMaker (1994). CrystalMaker, a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd., Oxford, England (www.crystalmaker.com). Flack, H. D. (1983), Acta Cryst. A39, 876-881. Flack, H. D. (2000), J. Appl. Cryst., 33, 1143-1148. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122 ; _publ_section_figure_captions ; Figure 1. SHELXTL (Bruker, 2005) plot showing 35% probability ellipsoids for non-H atoms and circles of arbitrary size for H atoms. ; _publ_section_exptl_prep ; Crystals were grown from a dichloroethane/hexane solution. ; _publ_section_exptl_refinement ; A structural model consisting of the molecule was developed. H atom treatment - Methyl H atom positions, R-CH~3~, were optimized by rotation about R-C bonds with idealized C-H, R--H and H--H distances. Remaining H atoms were included as riding idealized contributors. Methyl H atom U's were assigned as 1.5 times U~eq~ of the carrier atom; remaining H atom U's were assigned as 1.2 times carrier U~eq~. The absolute structure could not be determined by anamalous dispersion techniques (Flack, 1983 & 2000), however it could be established using the know stereochemistry of the bicycle. The stereochemistry of the bicycle is R, R, R, S for centers C5, C6, C7 and C9 restectively. The centers were set to the correct stereochemistry and then the Friedel pairs were merged in the final refinements. The unknown stereocenter at C15 was found to be an S center. ; _publ_contact_author ; Danielle L. Gray University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ; _publ_contact_author_phone '1 217 244 1708' _publ_contact_author_fax '1 217 244 8068' _publ_contact_author_email dgray@illinois.edu _publ_contact_letter ; Please consider this CIF submission for publication as a structural paper in Acta Crystallographica E. ; _publ_requested_journal 'Acta Crystallographica E' _publ_requested_coeditor_name ? _publ_section_title ; ? ; _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_acknowledgements ; The Materials Chemistry Laboratory at the University of Illinois was supported in part by grants NSF CHE 95-03145 and NSF CHE 03-43032 from the National Science Foundation. ; loop_ _publ_author_name _publ_author_address 'Gray, Danielle L.' ; University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ; 'Fuller, Amy L.' ; University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ; 'Gao, Yi-Gui' ; University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ; loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 1.00 0.00 0.3690 0.00 -1.00 0.00 0.3020 -1.00 0.00 0.00 0.0500 1.00 0.00 0.00 0.0890 0.00 0.00 -1.00 0.0400 0.00 0.00 1.00 0.0070