data_p46wa _audit_creation_method SHELXL-97 _audit_update_record ; ? ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H32 Br N O4' _chemical_formula_sum 'C26 H32 Br N O4' _chemical_formula_structural ? _chemical_formula_weight 502.44 _chemical_absolute_configuration ad _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 0.0016 '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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Orthorhombic' _symmetry_space_group_name_H-M 'P 21 21 21 ' _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 6.4190(11) _cell_length_b 17.531(3) _cell_length_c 22.374(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2517.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 868 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 24.6 _exptl_crystal_description 'tabular' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method ? _exptl_crystal_F_000 1048 _exptl_crystal_id p46wa _exptl_crystal_preparation ; The data crystal was mounted using epoxy to a thin glass fiber with the (-1 -1 0) scattering planes roughly normal to the spindle axis. ; _exptl_absorpt_coefficient_mu 1.663 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.4025 _exptl_absorpt_correction_T_max 0.8755 _exptl_absorpt_process_details '(Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id p46wa _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type ? _diffrn_measurement_device 'Siemens Platform/CCD' _diffrn_measurement_method 'profile data from \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 149 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 304 _diffrn_standards_decay_% 1.2 _diffrn_reflns_number 10940 _diffrn_reflns_av_R_equivalents 0.0540 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 25.35 _reflns_number_total 4280 _reflns_number_gt 3046 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT V6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT V6.22 (Bruker, 2001)' _computing_structure_solution 'SHELXTL V6.10 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL V6.10 (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL V6.10 (Bruker, 2001)' _computing_publication_material 'CIFTAB (Sheldrick, 2001)' _refine_special_details ; ? ; _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^)+(0.0371P)^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 noref _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 -0.011(8) _refine_ls_number_reflns 4280 _refine_ls_number_parameters 294 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0684 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0793 _refine_ls_wR_factor_gt 0.0724 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 1.08779(6) 0.63033(3) 0.971705(17) 0.07994(18) Uani 1 1 d . . . C1 C 0.7997(6) 0.5744(2) 0.81289(15) 0.0476(9) Uani 1 1 d . . . H1 H 0.8334 0.5450 0.7785 0.057 Uiso 1 1 calc R . . C2 C 0.9436(6) 0.5806(2) 0.85825(15) 0.0500(9) Uani 1 1 d . . . H2 H 1.0749 0.5559 0.8554 0.060 Uiso 1 1 calc R . . C3 C 0.8932(5) 0.6235(2) 0.90781(13) 0.0467(8) Uani 1 1 d . . . C4 C 0.7069(6) 0.6593(2) 0.91262(14) 0.0496(9) Uani 1 1 d . . . H4 H 0.6748 0.6888 0.9470 0.060 Uiso 1 1 calc R . . C5 C 0.5639(6) 0.65223(18) 0.86650(13) 0.0440(8) Uani 1 1 d . . . H5 H 0.4330 0.6772 0.8698 0.053 Uiso 1 1 calc R . . C6 C 0.6068(5) 0.60985(17) 0.81597(12) 0.0359(7) Uani 1 1 d . . . C7 C 0.4462(5) 0.6017(2) 0.76726(13) 0.0442(9) Uani 1 1 d . . . H7 H 0.3242 0.6339 0.7788 0.053 Uiso 1 1 calc R . . C8 C 0.5254(5) 0.6313(2) 0.70658(12) 0.0401(8) Uani 1 1 d . . . H8 H 0.6643 0.6079 0.6982 0.048 Uiso 1 1 calc R . . C9 C 0.5500(6) 0.7190(2) 0.70750(15) 0.0546(10) Uani 1 1 d . . . H9A H 0.6327 0.7337 0.7430 0.066 Uiso 1 1 calc R . . H9B H 0.6286 0.7350 0.6716 0.066 Uiso 1 1 calc R . . C10 C 0.3435(7) 0.7612(2) 0.70898(18) 0.0810(14) Uani 1 1 d . . . H10A H 0.3691 0.8166 0.7042 0.097 Uiso 1 1 calc R . . H10B H 0.2762 0.7532 0.7483 0.097 Uiso 1 1 calc R . . C11 C 0.1966(7) 0.7338(3) 0.65934(19) 0.0830(14) Uani 1 1 d . . . H11A H 0.0590 0.7585 0.6644 0.100 Uiso 1 1 calc R . . H11B H 0.2532 0.7496 0.6201 0.100 Uiso 1 1 calc R . . C12 C 0.1687(5) 0.6478(3) 0.65984(17) 0.0681(12) Uani 1 1 d . . . H12A H 0.0977 0.6317 0.6971 0.082 Uiso 1 1 calc R . . H12B H 0.0823 0.6317 0.6254 0.082 Uiso 1 1 calc R . . C13 C 0.3791(5) 0.61164(19) 0.65612(13) 0.0413(8) Uani 1 1 d . . . C14 C 0.4314(6) 0.57102(19) 0.60892(13) 0.0463(9) Uani 1 1 d . . . H14 H 0.3276 0.5637 0.5792 0.056 Uiso 1 1 calc R . . C15 C 0.7506(5) 0.56546(19) 0.54866(12) 0.0382(8) Uani 1 1 d . . . C16 C 0.7774(5) 0.64336(19) 0.54295(12) 0.0426(8) Uani 1 1 d . . . H16 H 0.7108 0.6770 0.5702 0.051 Uiso 1 1 calc R . . C17 C 0.9008(6) 0.67252(19) 0.49773(14) 0.0492(9) Uani 1 1 d . . . H17 H 0.9216 0.7260 0.4946 0.059 Uiso 1 1 calc R . . C18 C 0.9941(5) 0.6241(2) 0.45702(13) 0.0500(9) Uani 1 1 d . . . C19 C 0.9592(6) 0.5462(2) 0.46120(14) 0.0549(10) Uani 1 1 d . . . H19 H 1.0192 0.5125 0.4327 0.066 Uiso 1 1 calc R . . C20 C 0.8380(6) 0.5179(2) 0.50638(14) 0.0495(10) Uani 1 1 d . . . H20 H 0.8136 0.4645 0.5087 0.059 Uiso 1 1 calc R . . C21 C 0.6964(6) 0.47795(19) 0.63439(14) 0.0424(8) Uani 1 1 d . . . C22 C 0.9675(5) 0.38128(19) 0.64476(14) 0.0441(8) Uani 1 1 d . . . C23 C 0.8172(6) 0.3167(2) 0.63325(16) 0.0554(10) Uani 1 1 d . . . H23A H 0.6918 0.3239 0.6576 0.083 Uiso 1 1 calc R . . H23B H 0.8833 0.2681 0.6439 0.083 Uiso 1 1 calc R . . H23C H 0.7790 0.3160 0.5908 0.083 Uiso 1 1 calc R . . C24 C 1.0154(6) 0.3935(2) 0.71068(14) 0.0543(10) Uani 1 1 d . . . H24A H 1.0971 0.4403 0.7155 0.081 Uiso 1 1 calc R . . H24B H 1.0952 0.3500 0.7259 0.081 Uiso 1 1 calc R . . H24C H 0.8847 0.3981 0.7330 0.081 Uiso 1 1 calc R . . C25 C 1.1641(5) 0.3701(2) 0.60898(17) 0.0641(11) Uani 1 1 d . . . H25A H 1.1294 0.3670 0.5664 0.096 Uiso 1 1 calc R . . H25B H 1.2325 0.3227 0.6215 0.096 Uiso 1 1 calc R . . H25C H 1.2582 0.4132 0.6158 0.096 Uiso 1 1 calc R . . C26 C 1.2401(9) 0.6074(3) 0.3783(2) 0.111(2) Uani 1 1 d . . . H26A H 1.3313 0.5759 0.4034 0.167 Uiso 1 1 calc R . . H26B H 1.3250 0.6374 0.3505 0.167 Uiso 1 1 calc R . . H26C H 1.1456 0.5743 0.3557 0.167 Uiso 1 1 calc R . . N1 N 0.6307(4) 0.53696(15) 0.59842(10) 0.0407(7) Uani 1 1 d . . . O1 O 0.3753(4) 0.52497(14) 0.76423(10) 0.0586(7) Uani 1 1 d . . . H1A H 0.4419 0.5015 0.7377 0.088 Uiso 1 1 calc R . . O2 O 1.1212(5) 0.65762(13) 0.41535(11) 0.0715(8) Uani 1 1 d . . . O3 O 0.8841(4) 0.45259(13) 0.61862(9) 0.0464(6) Uani 1 1 d . . . O4 O 0.5933(4) 0.45291(13) 0.67567(9) 0.0522(6) Uani 1 1 d . . . 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 Br1 0.0648(3) 0.1235(4) 0.0515(2) 0.0184(3) -0.0179(2) -0.0240(3) C1 0.047(2) 0.056(2) 0.0393(19) 0.0008(17) 0.0034(16) 0.005(2) C2 0.039(2) 0.055(2) 0.056(2) 0.0111(19) 0.0028(17) 0.0053(18) C3 0.046(2) 0.055(2) 0.0388(17) 0.0094(18) -0.0076(15) -0.019(2) C4 0.065(3) 0.048(2) 0.0358(18) 0.0010(17) 0.0024(17) -0.0013(19) C5 0.048(2) 0.047(2) 0.0370(17) 0.0057(16) 0.0020(15) 0.0089(18) C6 0.036(2) 0.0349(19) 0.0368(16) 0.0058(14) 0.0078(14) 0.0036(17) C7 0.039(2) 0.057(3) 0.0368(17) 0.0028(16) 0.0035(14) -0.0015(18) C8 0.038(2) 0.047(2) 0.0349(16) -0.0022(17) 0.0012(12) 0.0031(18) C9 0.071(3) 0.050(2) 0.0430(19) -0.0020(17) 0.0091(18) -0.003(2) C10 0.115(4) 0.066(3) 0.061(3) 0.003(2) 0.031(3) 0.031(3) C11 0.078(3) 0.099(4) 0.072(3) 0.017(3) 0.018(2) 0.049(3) C12 0.046(3) 0.104(4) 0.054(2) 0.011(2) -0.0002(16) 0.011(2) C13 0.036(2) 0.051(2) 0.0380(17) 0.0070(17) -0.0028(14) 0.0043(17) C14 0.041(2) 0.058(2) 0.0397(18) 0.0080(17) -0.0122(16) -0.007(2) C15 0.053(2) 0.034(2) 0.0273(16) 0.0026(16) -0.0047(14) -0.0061(16) C16 0.059(2) 0.041(2) 0.0280(16) 0.0003(16) 0.0007(14) 0.0068(18) C17 0.076(3) 0.0295(19) 0.0419(18) 0.0006(16) 0.0012(19) -0.001(2) C18 0.072(2) 0.042(2) 0.0362(18) 0.0089(18) 0.0091(15) -0.002(2) C19 0.088(3) 0.039(2) 0.0373(19) -0.0020(17) 0.0159(18) -0.003(2) C20 0.080(3) 0.033(2) 0.0352(18) -0.0051(16) 0.0042(16) -0.0111(18) C21 0.047(2) 0.043(2) 0.0368(18) -0.0040(18) -0.0035(16) -0.0071(18) C22 0.052(2) 0.032(2) 0.0476(18) 0.0082(18) 0.0017(14) -0.0038(18) C23 0.064(3) 0.047(2) 0.055(2) -0.0009(19) 0.0041(19) -0.011(2) C24 0.064(3) 0.047(2) 0.052(2) 0.0050(18) -0.0123(17) -0.0014(19) C25 0.058(3) 0.054(2) 0.081(3) 0.005(2) 0.0152(18) 0.008(2) C26 0.161(5) 0.063(3) 0.109(4) 0.014(3) 0.085(4) 0.003(3) N1 0.0484(19) 0.0425(17) 0.0313(13) 0.0031(13) -0.0010(11) 0.0019(15) O1 0.0615(18) 0.0688(18) 0.0456(13) 0.0015(12) 0.0079(12) -0.0246(15) O2 0.116(2) 0.0407(15) 0.0582(15) 0.0053(12) 0.0361(16) 0.0019(15) O3 0.0474(15) 0.0460(14) 0.0459(12) 0.0147(11) 0.0085(11) 0.0017(13) O4 0.0521(15) 0.0546(15) 0.0498(13) 0.0130(12) 0.0110(13) -0.0007(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 Br1 C3 1.902(3) . ? C1 C2 1.377(5) . ? C1 C6 1.387(4) . ? C1 H1 0.9500 . ? C2 C3 1.378(5) . ? C2 H2 0.9500 . ? C3 C4 1.355(5) . ? C4 C5 1.387(5) . ? C4 H4 0.9500 . ? C5 C6 1.381(4) . ? C5 H5 0.9500 . ? C6 C7 1.507(4) . ? C7 O1 1.421(4) . ? C7 C8 1.540(4) . ? C7 H7 1.0000 . ? C8 C13 1.508(4) . ? C8 C9 1.545(5) . ? C8 H8 1.0000 . ? C9 C10 1.519(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.534(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.518(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.494(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.317(4) . ? C14 N1 1.431(4) . ? C14 H14 0.9500 . ? C15 C20 1.380(4) . ? C15 C16 1.382(4) . ? C15 N1 1.443(4) . ? C16 C17 1.383(4) . ? C16 H16 0.9500 . ? C17 C18 1.382(5) . ? C17 H17 0.9500 . ? C18 O2 1.371(4) . ? C18 C19 1.387(5) . ? C19 C20 1.368(4) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 O4 1.218(4) . ? C21 O3 1.332(4) . ? C21 N1 1.377(4) . ? C22 O3 1.480(4) . ? C22 C25 1.507(4) . ? C22 C23 1.510(5) . ? C22 C24 1.522(4) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 O2 1.430(5) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? O1 H1A 0.8400 . ? 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 C1 C6 121.8(3) . . ? C2 C1 H1 119.1 . . ? C6 C1 H1 119.1 . . ? C1 C2 C3 118.6(3) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 121.6(3) . . ? C4 C3 Br1 119.4(3) . . ? C2 C3 Br1 119.0(3) . . ? C3 C4 C5 118.9(3) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 121.7(3) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C1 117.4(3) . . ? C5 C6 C7 120.5(3) . . ? C1 C6 C7 122.1(3) . . ? O1 C7 C6 110.1(3) . . ? O1 C7 C8 112.5(3) . . ? C6 C7 C8 112.3(3) . . ? O1 C7 H7 107.2 . . ? C6 C7 H7 107.2 . . ? C8 C7 H7 107.2 . . ? C13 C8 C7 112.1(3) . . ? C13 C8 C9 107.5(3) . . ? C7 C8 C9 111.0(3) . . ? C13 C8 H8 108.7 . . ? C7 C8 H8 108.7 . . ? C9 C8 H8 108.7 . . ? C10 C9 C8 113.3(3) . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9B 108.9 . . ? C8 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 C11 111.6(3) . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C10 112.2(3) . . ? C12 C11 H11A 109.2 . . ? C10 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C13 C12 C11 108.3(3) . . ? C13 C12 H12A 110.0 . . ? C11 C12 H12A 110.0 . . ? C13 C12 H12B 110.0 . . ? C11 C12 H12B 110.0 . . ? H12A C12 H12B 108.4 . . ? C14 C13 C12 120.3(3) . . ? C14 C13 C8 124.4(3) . . ? C12 C13 C8 115.1(3) . . ? C13 C14 N1 125.8(3) . . ? C13 C14 H14 117.1 . . ? N1 C14 H14 117.1 . . ? C20 C15 C16 118.9(3) . . ? C20 C15 N1 122.5(3) . . ? C16 C15 N1 118.7(3) . . ? C15 C16 C17 120.3(3) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C18 C17 C16 120.2(3) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? O2 C18 C17 116.3(3) . . ? O2 C18 C19 124.3(3) . . ? C17 C18 C19 119.4(3) . . ? C20 C19 C18 119.9(3) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C15 121.2(3) . . ? C19 C20 H20 119.4 . . ? C15 C20 H20 119.4 . . ? O4 C21 O3 124.9(3) . . ? O4 C21 N1 123.2(3) . . ? O3 C21 N1 111.9(3) . . ? O3 C22 C25 101.7(3) . . ? O3 C22 C23 109.6(3) . . ? C25 C22 C23 110.3(3) . . ? O3 C22 C24 109.7(3) . . ? C25 C22 C24 111.3(3) . . ? C23 C22 C24 113.6(3) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O2 C26 H26A 109.5 . . ? O2 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O2 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C21 N1 C14 119.4(3) . . ? C21 N1 C15 123.2(3) . . ? C14 N1 C15 117.3(3) . . ? C7 O1 H1A 109.5 . . ? C18 O2 C26 116.6(3) . . ? C21 O3 C22 120.3(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 C6 C1 C2 C3 -0.1(5) . . . . ? C1 C2 C3 C4 -0.1(5) . . . . ? C1 C2 C3 Br1 178.4(3) . . . . ? C2 C3 C4 C5 0.2(5) . . . . ? Br1 C3 C4 C5 -178.2(2) . . . . ? C3 C4 C5 C6 -0.2(5) . . . . ? C4 C5 C6 C1 -0.1(5) . . . . ? C4 C5 C6 C7 178.5(3) . . . . ? C2 C1 C6 C5 0.2(5) . . . . ? C2 C1 C6 C7 -178.4(3) . . . . ? C5 C6 C7 O1 -112.5(3) . . . . ? C1 C6 C7 O1 66.0(4) . . . . ? C5 C6 C7 C8 121.2(3) . . . . ? C1 C6 C7 C8 -60.2(4) . . . . ? O1 C7 C8 C13 45.8(4) . . . . ? C6 C7 C8 C13 170.8(3) . . . . ? O1 C7 C8 C9 166.1(3) . . . . ? C6 C7 C8 C9 -69.0(4) . . . . ? C13 C8 C9 C10 52.4(4) . . . . ? C7 C8 C9 C10 -70.6(4) . . . . ? C8 C9 C10 C11 -51.7(4) . . . . ? C9 C10 C11 C12 52.8(5) . . . . ? C10 C11 C12 C13 -55.2(4) . . . . ? C11 C12 C13 C14 -114.7(4) . . . . ? C11 C12 C13 C8 60.1(4) . . . . ? C7 C8 C13 C14 -121.1(3) . . . . ? C9 C8 C13 C14 116.6(4) . . . . ? C7 C8 C13 C12 64.3(4) . . . . ? C9 C8 C13 C12 -58.0(4) . . . . ? C12 C13 C14 N1 176.5(3) . . . . ? C8 C13 C14 N1 2.2(5) . . . . ? C20 C15 C16 C17 -4.1(5) . . . . ? N1 C15 C16 C17 176.4(3) . . . . ? C15 C16 C17 C18 1.6(5) . . . . ? C16 C17 C18 O2 -177.2(3) . . . . ? C16 C17 C18 C19 1.4(5) . . . . ? O2 C18 C19 C20 176.6(3) . . . . ? C17 C18 C19 C20 -1.9(5) . . . . ? C18 C19 C20 C15 -0.7(5) . . . . ? C16 C15 C20 C19 3.6(5) . . . . ? N1 C15 C20 C19 -176.9(3) . . . . ? O4 C21 N1 C14 -0.5(5) . . . . ? O3 C21 N1 C14 179.8(3) . . . . ? O4 C21 N1 C15 -178.5(3) . . . . ? O3 C21 N1 C15 1.8(4) . . . . ? C13 C14 N1 C21 67.4(4) . . . . ? C13 C14 N1 C15 -114.5(4) . . . . ? C20 C15 N1 C21 48.1(4) . . . . ? C16 C15 N1 C21 -132.5(3) . . . . ? C20 C15 N1 C14 -130.0(3) . . . . ? C16 C15 N1 C14 49.5(4) . . . . ? C17 C18 O2 C26 171.8(4) . . . . ? C19 C18 O2 C26 -6.7(6) . . . . ? O4 C21 O3 C22 10.7(5) . . . . ? N1 C21 O3 C22 -169.6(3) . . . . ? C25 C22 O3 C21 173.0(3) . . . . ? C23 C22 O3 C21 56.3(3) . . . . ? C24 C22 O3 C21 -69.0(4) . . . . ? 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 O1 H1A O4 0.84 1.90 2.735(3) 177.3 . _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.289 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.041 _publ_requested_category CO _publ_section_references ; Sheldrick, G.M. (2001). SHELX-97-2. Program for crystal structure solution and refinement. Institute fur anorg chemie, G\"ottingen, Germany. Bruker AXS, Inc. (2001). Madison, Wisconsin, USA. ; _publ_section_figure_captions ; Figure 1. SHELXTL (Bruker, 2000) 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 ethylacetate/methylenechloride. Three frame series were filtered for statistical outliers then corrected for absorption by integration using SHELXTL/XPREP (Bruker, 2001). A series of identical frames was collected twice during the experiment to monitor decay. No decay correction was applied. ; _publ_section_exptl_refinement ; Systematic conditions suggested the unambiguous space group. Structure was solved by direct methods (Sheldrick, 2001). 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. Methyl H atom U's were assigned as 1.5 times Ueq of corresponding methyl C atom. Remaining H atoms were included as riding idealized contributors with U's assigned as 1.2 times Ueq of adjacent non-H atoms. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F^2^ (Sheldrick, 2001). The highest peaks in the final difference Fourier map were in the vicinity of the Br atom; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed no dependence on amplitude or resolution. ; _publ_contact_author ; Peter Beak University of Illinois at Urbana-Champaign Department of Chemistry, Roger Adams Laboratory 600 South Mathews Avenue Urbana, Illinois 61801 USA ; _publ_contact_author_phone '1 217 333 2805' _publ_contact_author_fax '1 217 244 8068' _publ_contact_author_email beak@scs.uiuc.edu _publ_contact_letter ; Please consider this CIF submission from a publication in J. Org. Chem. ; _publ_requested_journal 'J. Org. Chem.' _publ_requested_coeditor_name ? _publ_section_title ; Asymmetric Lithiation-Substitution Sequences of Substituted Allyl Amines ; _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_acknowledgements ; We are grateful to the National Institutes of Health(GM-18874) for support of this work.The Materials Chemistry Laboratory at the Univeristy of Illinois was supported in part by Grant No. NSF CHE 95-03145 from the National Science Foundation. ; loop_ _publ_author_name _publ_author_address 'Beak, Peter' ; University of Illinois at Urbana-Champaign Department of Chemistry, Roger Adams Laboratory 600 South Mathews Avenue Urbana, Illinois 61801 USA ; 'Lee, Suk Joong' ; University of Illinois at Urbana-Champaign Department of Chemistry, Roger Adams Laboratory 600 South Mathews Avenue Urbana, Illinois 61801 USA ; 'Kim, Dwight D.' ; University of Illinois at Urbana-Champaign Department of Chemistry, Roger Adams Laboratory 600 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 0.0400 0.00 0.00 -1.00 0.0400 0.00 1.00 0.00 0.1600 0.00 -1.00 0.00 0.1600 1.00 0.00 0.00 0.2900 -1.00 0.00 0.00 0.2900