data_ba55mas _audit_creation_method SHELXL-97 _audit_update_record ; ? ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H28 B N O5 ' _chemical_formula_sum 'C22 H28 B N O5' _chemical_formula_structural ? _chemical_formula_weight 397.26 _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 'Orthorhombic' _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.0616(6) _cell_length_b 10.2832(8) _cell_length_c 29.237(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2123.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4483 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 20.45 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.560 _exptl_crystal_size_mid 0.420 _exptl_crystal_size_min 0.069 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_crystal_id ba55mas _exptl_crystal_preparation ; The data crystal was mounted using oil (Parantone-N, Exxon) to a 0.3 mm cryo-loop (Hampton Research) with the (1 -1 -1) scattering planes roughly normal to the spindle axis. ; _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.9602 _exptl_absorpt_correction_T_max 0.9939 _exptl_absorpt_process_details 'SHELXTL/XPREP V2005/2 (Bruker, 2005)' _exptl_special_details ; One distinct cell was identified using APEX2 (Bruker, 2004). Five 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 SAINT/SADABS (Bruker, 2005) to sort, merge, and scale the combined data. No decay correction was applied. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id ba55mas _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 33736 _diffrn_reflns_av_R_equivalents 0.0909 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.39 _reflns_number_total 2264 _reflns_number_gt 1841 _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, (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 unambiguous 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 not significant features. A final analysis of variance between observed and calculated structure factors showed little dependence on amplitude or resolution. In the final refinement all equivalents were averaged including the Friedel opposites and the delta f" were set to zero because there was no heavy atom to determine the absolute structure via anomalous dispersion techniques. Instead, the absolute structure was set from the know stereochemical configuration of the bi-cycle attached to the N atom. ; _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^+0.2270P] 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 'Friedel's merged' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 2264 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0889 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 N1 N 0.0997(3) 1.00998(18) 0.79636(6) 0.0216(4) Uani 1 1 d . . . B1 B 0.0806(4) 0.8504(3) 0.79218(10) 0.0274(7) Uani 1 1 d . . . O1 O 0.1025(3) 0.83276(17) 0.74236(5) 0.0312(4) Uani 1 1 d . . . O2 O 0.1970(3) 0.94194(19) 0.68002(6) 0.0409(5) Uani 1 1 d . . . O3 O -0.3918(3) 0.93528(19) 0.80485(7) 0.0467(5) Uani 1 1 d . . . O4 O -0.1183(2) 0.82629(16) 0.80464(6) 0.0314(4) Uani 1 1 d . . . O5 O 0.2053(3) 0.62424(16) 0.81428(6) 0.0347(5) Uani 1 1 d . . . C1 C 0.1694(3) 0.9368(3) 0.72059(9) 0.0293(6) Uani 1 1 d . . . C2 C 0.2126(3) 1.0433(2) 0.75440(8) 0.0260(6) Uani 1 1 d . . . H2A H 0.3497 1.0457 0.7615 0.031 Uiso 1 1 calc R . . H2B H 0.1741 1.1290 0.7421 0.031 Uiso 1 1 calc R . . C3 C -0.1035(3) 1.0503(2) 0.79066(8) 0.0249(5) Uani 1 1 d . . . H3A H -0.1347 1.1220 0.8120 0.030 Uiso 1 1 calc R . . H3B H -0.1267 1.0805 0.7590 0.030 Uiso 1 1 calc R . . C4 C -0.2225(3) 0.9328(2) 0.80101(9) 0.0298(6) Uani 1 1 d . . . C5 C 0.1925(3) 1.0627(2) 0.83999(8) 0.0240(5) Uani 1 1 d . . . H5A H 0.3229 1.0250 0.8410 0.029 Uiso 1 1 calc R . . C6 C 0.2180(4) 1.2141(2) 0.83821(9) 0.0290(6) Uani 1 1 d . . . H6A H 0.1201 1.2490 0.8168 0.035 Uiso 1 1 calc R . . C7 C 0.1798(4) 1.2736(3) 0.88514(9) 0.0331(6) Uani 1 1 d . . . H7A H 0.2078 1.3688 0.8871 0.040 Uiso 1 1 calc R . . C8 C 0.2560(4) 1.1915(3) 0.92698(9) 0.0370(7) Uani 1 1 d . . . C9 C 0.0694(4) 1.1124(3) 0.92106(9) 0.0339(7) Uani 1 1 d . . . H9A H 0.0109 1.0806 0.9501 0.041 Uiso 1 1 calc R . . C10 C 0.0879(4) 1.0105(3) 0.88316(8) 0.0307(6) Uani 1 1 d . . . H10A H -0.0402 0.9807 0.8742 0.037 Uiso 1 1 calc R . . H10B H 0.1578 0.9344 0.8952 0.037 Uiso 1 1 calc R . . C11 C -0.0208(4) 1.2362(3) 0.90082(9) 0.0350(7) Uani 1 1 d . . . H11A H -0.1106 1.2196 0.8755 0.042 Uiso 1 1 calc R . . H11B H -0.0759 1.2956 0.9239 0.042 Uiso 1 1 calc R . . C12 C 0.4122(4) 1.2577(3) 0.82023(10) 0.0409(7) Uani 1 1 d . . . H12A H 0.4218 1.3526 0.8221 0.061 Uiso 1 1 calc R . . H12B H 0.4264 1.2303 0.7883 0.061 Uiso 1 1 calc R . . H12C H 0.5123 1.2181 0.8388 0.061 Uiso 1 1 calc R . . C13 C 0.4443(5) 1.1197(4) 0.92497(10) 0.0489(8) Uani 1 1 d . . . H13A H 0.4569 1.0636 0.9519 0.073 Uiso 1 1 calc R . . H13B H 0.5483 1.1828 0.9245 0.073 Uiso 1 1 calc R . . H13C H 0.4491 1.0664 0.8972 0.073 Uiso 1 1 calc R . . C14 C 0.2537(5) 1.2722(3) 0.97098(10) 0.0522(9) Uani 1 1 d . . . H14A H 0.2613 1.2142 0.9975 0.078 Uiso 1 1 calc R . . H14B H 0.1360 1.3226 0.9725 0.078 Uiso 1 1 calc R . . H14C H 0.3622 1.3317 0.9711 0.078 Uiso 1 1 calc R . . C15 C 0.2256(4) 0.7662(2) 0.82066(9) 0.0284(6) Uani 1 1 d . . . H15A H 0.3586 0.7995 0.8214 0.034 Uiso 1 1 calc R . . C16 C 0.1722(4) 0.6796(3) 0.85861(9) 0.0321(6) Uani 1 1 d . . . H16A H 0.0366 0.6842 0.8683 0.039 Uiso 1 1 calc R . . C17 C 0.3097(4) 0.6465(2) 0.89551(9) 0.0331(6) Uani 1 1 d . . . C18 C 0.2586(5) 0.6623(3) 0.94079(10) 0.0466(8) Uani 1 1 d . . . H18A H 0.1339 0.6895 0.9483 0.056 Uiso 1 1 calc R . . C19 C 0.3884(6) 0.6385(3) 0.97542(11) 0.0587(10) Uani 1 1 d . . . H19A H 0.3525 0.6505 1.0064 0.070 Uiso 1 1 calc R . . C20 C 0.5680(6) 0.5977(3) 0.96509(11) 0.0578(10) Uani 1 1 d . . . H20A H 0.6566 0.5815 0.9889 0.069 Uiso 1 1 calc R . . C21 C 0.6196(5) 0.5803(3) 0.92007(11) 0.0499(8) Uani 1 1 d . . . H21A H 0.7436 0.5509 0.9128 0.060 Uiso 1 1 calc R . . C22 C 0.4917(4) 0.6054(3) 0.88545(10) 0.0392(7) Uani 1 1 d . . . H22A H 0.5289 0.5943 0.8545 0.047 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 N1 0.0198(10) 0.0198(10) 0.0254(11) 0.0017(9) -0.0011(9) -0.0005(9) B1 0.0270(15) 0.0177(15) 0.0374(18) -0.0025(13) -0.0048(13) -0.0011(12) O1 0.0394(10) 0.0224(9) 0.0316(10) -0.0039(8) -0.0039(8) 0.0008(8) O2 0.0418(11) 0.0501(13) 0.0309(11) -0.0072(9) 0.0040(9) 0.0013(10) O3 0.0205(10) 0.0401(12) 0.0796(15) 0.0065(11) 0.0003(10) -0.0038(9) O4 0.0251(9) 0.0225(9) 0.0467(11) 0.0020(8) -0.0034(8) -0.0022(8) O5 0.0472(12) 0.0211(9) 0.0359(11) -0.0018(8) -0.0080(9) 0.0006(9) C1 0.0222(13) 0.0324(15) 0.0333(16) -0.0015(12) -0.0025(11) 0.0044(11) C2 0.0233(13) 0.0266(14) 0.0282(13) 0.0021(11) 0.0015(10) -0.0023(11) C3 0.0210(12) 0.0216(13) 0.0323(14) 0.0014(11) -0.0027(10) 0.0002(11) C4 0.0246(14) 0.0292(14) 0.0358(14) 0.0000(12) -0.0035(11) -0.0039(12) C5 0.0228(12) 0.0220(13) 0.0273(13) -0.0001(11) -0.0044(11) -0.0008(11) C6 0.0310(14) 0.0239(14) 0.0322(14) -0.0005(11) -0.0009(12) -0.0045(11) C7 0.0342(14) 0.0257(14) 0.0394(15) -0.0086(12) 0.0014(12) -0.0032(12) C8 0.0351(15) 0.0440(18) 0.0318(15) -0.0100(13) -0.0011(12) -0.0014(14) C9 0.0395(16) 0.0353(16) 0.0267(14) 0.0013(12) 0.0015(12) -0.0023(13) C10 0.0339(14) 0.0277(14) 0.0306(14) 0.0018(12) -0.0018(12) -0.0019(12) C11 0.0368(15) 0.0301(16) 0.0382(16) -0.0095(13) 0.0038(12) 0.0019(13) C12 0.0410(16) 0.0366(17) 0.0451(17) -0.0095(13) 0.0086(13) -0.0168(14) C13 0.0404(18) 0.065(2) 0.0415(18) -0.0123(16) -0.0123(14) 0.0031(15) C14 0.054(2) 0.061(2) 0.0412(17) -0.0198(16) -0.0028(15) -0.0058(18) C15 0.0308(14) 0.0168(13) 0.0377(14) -0.0018(11) -0.0024(11) -0.0015(11) C16 0.0300(14) 0.0310(15) 0.0353(16) -0.0008(12) 0.0010(11) 0.0003(12) C17 0.0409(15) 0.0246(15) 0.0338(16) 0.0040(12) -0.0033(13) -0.0004(12) C18 0.061(2) 0.0426(18) 0.0361(17) 0.0040(14) 0.0022(15) 0.0084(16) C19 0.086(3) 0.058(2) 0.0321(17) 0.0047(15) -0.0062(18) 0.004(2) C20 0.069(2) 0.054(2) 0.051(2) 0.0111(17) -0.0247(18) -0.0036(19) C21 0.0430(18) 0.050(2) 0.057(2) 0.0125(16) -0.0114(15) 0.0012(16) C22 0.0398(16) 0.0370(18) 0.0408(17) 0.0066(14) -0.0040(14) 0.0004(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 N1 C2 1.503(3) . ? N1 C3 1.503(3) . ? N1 C5 1.533(3) . ? N1 B1 1.651(3) . ? B1 O4 1.472(3) . ? B1 O1 1.476(3) . ? B1 C15 1.579(4) . ? O1 C1 1.331(3) . ? O2 C1 1.203(3) . ? O3 C4 1.201(3) . ? O4 C4 1.323(3) . ? O5 C16 1.435(3) . ? O5 C15 1.478(3) . ? C1 C2 1.506(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.503(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 C10 1.558(3) . ? C5 C6 1.568(3) . ? C5 H5A 1.0000 . ? C6 C7 1.527(4) . ? C6 C12 1.536(4) . ? C6 H6A 1.0000 . ? C7 C11 1.538(4) . ? C7 C8 1.581(4) . ? C7 H7A 1.0000 . ? C8 C13 1.522(4) . ? C8 C14 1.531(4) . ? C8 C9 1.558(4) . ? C9 C10 1.531(4) . ? C9 C11 1.541(4) . ? C9 H9A 1.0000 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? 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 1.472(4) . ? C15 H15A 1.0000 . ? C16 C17 1.491(4) . ? C16 H16A 1.0000 . ? C17 C18 1.382(4) . ? C17 C22 1.385(4) . ? C18 C19 1.387(5) . ? C18 H18A 0.9500 . ? C19 C20 1.370(5) . ? C19 H19A 0.9500 . ? C20 C21 1.377(5) . ? C20 H20A 0.9500 . ? C21 C22 1.381(4) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C3 110.69(18) . . ? C2 N1 C5 111.85(17) . . ? C3 N1 C5 113.73(18) . . ? C2 N1 B1 102.08(19) . . ? C3 N1 B1 100.82(18) . . ? C5 N1 B1 116.63(18) . . ? O4 B1 O1 108.9(2) . . ? O4 B1 C15 113.3(2) . . ? O1 B1 C15 112.6(2) . . ? O4 B1 N1 103.1(2) . . ? O1 B1 N1 100.8(2) . . ? C15 B1 N1 116.9(2) . . ? C1 O1 B1 114.2(2) . . ? C4 O4 B1 111.8(2) . . ? C16 O5 C15 60.68(16) . . ? O2 C1 O1 124.4(2) . . ? O2 C1 C2 125.6(3) . . ? O1 C1 C2 110.0(2) . . ? N1 C2 C1 105.22(19) . . ? N1 C2 H2A 110.7 . . ? C1 C2 H2A 110.7 . . ? N1 C2 H2B 110.7 . . ? C1 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? C4 C3 N1 106.85(19) . . ? C4 C3 H3A 110.4 . . ? N1 C3 H3A 110.4 . . ? C4 C3 H3B 110.4 . . ? N1 C3 H3B 110.4 . . ? H3A C3 H3B 108.6 . . ? O3 C4 O4 124.3(3) . . ? O3 C4 C3 123.9(3) . . ? O4 C4 C3 111.8(2) . . ? N1 C5 C10 110.46(19) . . ? N1 C5 C6 111.88(18) . . ? C10 C5 C6 115.1(2) . . ? N1 C5 H5A 106.3 . . ? C10 C5 H5A 106.3 . . ? C6 C5 H5A 106.3 . . ? C7 C6 C12 110.4(2) . . ? C7 C6 C5 110.4(2) . . ? C12 C6 C5 113.8(2) . . ? C7 C6 H6A 107.3 . . ? C12 C6 H6A 107.3 . . ? C5 C6 H6A 107.3 . . ? C6 C7 C11 109.3(2) . . ? C6 C7 C8 114.9(2) . . ? C11 C7 C8 87.1(2) . . ? C6 C7 H7A 114.2 . . ? C11 C7 H7A 114.2 . . ? C8 C7 H7A 114.2 . . ? C13 C8 C14 107.8(2) . . ? C13 C8 C9 118.8(2) . . ? C14 C8 C9 111.5(2) . . ? C13 C8 C7 121.8(2) . . ? C14 C8 C7 110.9(2) . . ? C9 C8 C7 84.53(19) . . ? C10 C9 C11 108.8(2) . . ? C10 C9 C8 111.5(2) . . ? C11 C9 C8 87.8(2) . . ? C10 C9 H9A 115.2 . . ? C11 C9 H9A 115.2 . . ? C8 C9 H9A 115.2 . . ? C9 C10 C5 113.0(2) . . ? C9 C10 H10A 109.0 . . ? C5 C10 H10A 109.0 . . ? C9 C10 H10B 109.0 . . ? C5 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C7 C11 C9 86.6(2) . . ? C7 C11 H11A 114.2 . . ? C9 C11 H11A 114.2 . . ? C7 C11 H11B 114.2 . . ? C9 C11 H11B 114.2 . . ? H11A C11 H11B 111.4 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? 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 58.19(15) . . ? C16 C15 B1 124.3(2) . . ? O5 C15 B1 114.3(2) . . ? C16 C15 H15A 115.6 . . ? O5 C15 H15A 115.6 . . ? B1 C15 H15A 115.6 . . ? O5 C16 C15 61.13(16) . . ? O5 C16 C17 117.2(2) . . ? C15 C16 C17 121.1(2) . . ? O5 C16 H16A 115.5 . . ? C15 C16 H16A 115.5 . . ? C17 C16 H16A 115.5 . . ? C18 C17 C22 118.8(3) . . ? C18 C17 C16 119.8(3) . . ? C22 C17 C16 121.4(2) . . ? C17 C18 C19 120.4(3) . . ? C17 C18 H18A 119.8 . . ? C19 C18 H18A 119.8 . . ? C20 C19 C18 120.3(3) . . ? C20 C19 H19A 119.8 . . ? C18 C19 H19A 119.8 . . ? C19 C20 C21 119.7(3) . . ? C19 C20 H20A 120.2 . . ? C21 C20 H20A 120.2 . . ? C20 C21 C22 120.2(3) . . ? C20 C21 H21A 119.9 . . ? C22 C21 H21A 119.9 . . ? C21 C22 C17 120.6(3) . . ? C21 C22 H22A 119.7 . . ? C17 C22 H22A 119.7 . . ? 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 C2 N1 B1 O4 -137.24(19) . . . . ? C3 N1 B1 O4 -23.1(2) . . . . ? C5 N1 B1 O4 100.5(2) . . . . ? C2 N1 B1 O1 -24.7(2) . . . . ? C3 N1 B1 O1 89.4(2) . . . . ? C5 N1 B1 O1 -146.94(18) . . . . ? C2 N1 B1 C15 97.7(3) . . . . ? C3 N1 B1 C15 -148.2(2) . . . . ? C5 N1 B1 C15 -24.5(3) . . . . ? O4 B1 O1 C1 122.2(2) . . . . ? C15 B1 O1 C1 -111.3(2) . . . . ? N1 B1 O1 C1 14.1(3) . . . . ? O1 B1 O4 C4 -87.5(3) . . . . ? C15 B1 O4 C4 146.4(2) . . . . ? N1 B1 O4 C4 19.0(3) . . . . ? B1 O1 C1 O2 -179.9(3) . . . . ? B1 O1 C1 C2 2.6(3) . . . . ? C3 N1 C2 C1 -79.9(2) . . . . ? C5 N1 C2 C1 152.16(19) . . . . ? B1 N1 C2 C1 26.7(2) . . . . ? O2 C1 C2 N1 162.4(2) . . . . ? O1 C1 C2 N1 -20.1(3) . . . . ? C2 N1 C3 C4 127.2(2) . . . . ? C5 N1 C3 C4 -105.9(2) . . . . ? B1 N1 C3 C4 19.8(2) . . . . ? B1 O4 C4 O3 172.3(3) . . . . ? B1 O4 C4 C3 -6.8(3) . . . . ? N1 C3 C4 O3 170.9(3) . . . . ? N1 C3 C4 O4 -10.0(3) . . . . ? C2 N1 C5 C10 -172.1(2) . . . . ? C3 N1 C5 C10 61.6(2) . . . . ? B1 N1 C5 C10 -55.2(3) . . . . ? C2 N1 C5 C6 58.3(2) . . . . ? C3 N1 C5 C6 -68.0(2) . . . . ? B1 N1 C5 C6 175.2(2) . . . . ? N1 C5 C6 C7 141.9(2) . . . . ? C10 C5 C6 C7 14.7(3) . . . . ? N1 C5 C6 C12 -93.3(3) . . . . ? C10 C5 C6 C12 139.5(2) . . . . ? C12 C6 C7 C11 176.1(2) . . . . ? C5 C6 C7 C11 -57.2(3) . . . . ? C12 C6 C7 C8 -88.0(3) . . . . ? C5 C6 C7 C8 38.7(3) . . . . ? C6 C7 C8 C13 38.2(4) . . . . ? C11 C7 C8 C13 148.2(3) . . . . ? C6 C7 C8 C14 166.6(2) . . . . ? C11 C7 C8 C14 -83.4(3) . . . . ? C6 C7 C8 C9 -82.4(2) . . . . ? C11 C7 C8 C9 27.54(19) . . . . ? C13 C8 C9 C10 -41.5(3) . . . . ? C14 C8 C9 C10 -167.8(2) . . . . ? C7 C8 C9 C10 81.9(2) . . . . ? C13 C8 C9 C11 -150.9(2) . . . . ? C14 C8 C9 C11 82.9(3) . . . . ? C7 C8 C9 C11 -27.46(19) . . . . ? C11 C9 C10 C5 52.9(3) . . . . ? C8 C9 C10 C5 -42.3(3) . . . . ? N1 C5 C10 C9 -141.1(2) . . . . ? C6 C5 C10 C9 -13.3(3) . . . . ? C6 C7 C11 C9 87.6(2) . . . . ? C8 C7 C11 C9 -27.79(18) . . . . ? C10 C9 C11 C7 -83.7(2) . . . . ? C8 C9 C11 C7 28.22(19) . . . . ? C16 O5 C15 B1 -116.5(3) . . . . ? O4 B1 C15 C16 -4.8(3) . . . . ? O1 B1 C15 C16 -129.0(3) . . . . ? N1 B1 C15 C16 115.0(3) . . . . ? O4 B1 C15 O5 62.1(3) . . . . ? O1 B1 C15 O5 -62.0(3) . . . . ? N1 B1 C15 O5 -178.1(2) . . . . ? C15 O5 C16 C17 -112.3(3) . . . . ? B1 C15 C16 O5 99.5(3) . . . . ? O5 C15 C16 C17 106.1(3) . . . . ? B1 C15 C16 C17 -154.4(2) . . . . ? O5 C16 C17 C18 -160.5(2) . . . . ? C15 C16 C17 C18 128.4(3) . . . . ? O5 C16 C17 C22 22.4(4) . . . . ? C15 C16 C17 C22 -48.7(4) . . . . ? C22 C17 C18 C19 0.7(4) . . . . ? C16 C17 C18 C19 -176.6(3) . . . . ? C17 C18 C19 C20 -0.7(5) . . . . ? C18 C19 C20 C21 0.0(5) . . . . ? C19 C20 C21 C22 0.8(5) . . . . ? C20 C21 C22 C17 -0.9(5) . . . . ? C18 C17 C22 C21 0.1(4) . . . . ? C16 C17 C22 C21 177.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.996 _diffrn_standards_number ? _diffrn_standards_decay_% ? _diffrn_standards_interval_time ? _refine_diff_density_max 0.147 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.043 _publ_requested_category FM _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 hexane and dichloroethane 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 molecule contains no heavy atoms so the absolute structure could not be determined from anamalous dispersion data (Flack, 1983 & 2000). The absolute structure of the molecule was determined by setting the known configuration of the bi-cycle. C5, C6, and C7 are known R type chiral centers and C9 is a known S type center. Once these chiral centers were set, the unknown chiral centers at C15 and C16 were determined to be S configuration chiral centers. ; _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 0.00 -1.00 0.0600 0.00 0.00 1.00 0.0090 1.00 0.00 0.00 0.2430 -1.00 0.00 0.00 0.3170 0.00 -1.00 0.00 0.2300