data_09082a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 09082a _chemical_melting_point ? _chemical_formula_moiety 'C20 H23 Br N, Br3' _chemical_formula_sum 'C20 H23 Br4 N' _chemical_formula_weight 597.03 _chemical_absolute_configuration ad 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' '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 'P2(1)2(1)2(1)' 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 7.966(2) _cell_length_b 8.544(2) _cell_length_c 31.115(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2117.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2990 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 27.30 _exptl_crystal_description 'Block' _exptl_crystal_colour 'Orange' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.873 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 7.605 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.1760 _exptl_absorpt_correction_T_max 0.3950 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details 'D. Thaisrivongs / Prof. B. Trost - Stanford University' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24641 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4838 _reflns_number_gt 4371 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0224P)^2^+1.4023P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.004(10) _refine_ls_number_reflns 4838 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0573 _refine_ls_wR_factor_gt 0.0552 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.002 _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 C1 C 0.4248(4) 0.5215(4) 0.60219(10) 0.0272(7) Uani 1 1 d . . . H1A H 0.5259 0.4524 0.6007 0.033 Uiso 1 1 calc R . . C2 C 0.2651(4) 0.4303(4) 0.59125(10) 0.0279(7) Uani 1 1 d . . . H2A H 0.1696 0.5062 0.5899 0.033 Uiso 1 1 calc R . . Br1 Br 0.28646(5) 0.33017(4) 0.534755(12) 0.03611(9) Uani 1 1 d . . . C3 C 0.2278(5) 0.3127(4) 0.62644(11) 0.0318(8) Uani 1 1 d . . . H3A H 0.3268 0.2454 0.6316 0.038 Uiso 1 1 calc R . . H3B H 0.1321 0.2454 0.6181 0.038 Uiso 1 1 calc R . . C4 C 0.1848(5) 0.4067(4) 0.66703(11) 0.0332(8) Uani 1 1 d . . . H4A H 0.0894 0.4777 0.6610 0.040 Uiso 1 1 calc R . . H4B H 0.1507 0.3343 0.6903 0.040 Uiso 1 1 calc R . . C5 C 0.3358(5) 0.5021(4) 0.68151(10) 0.0341(8) Uani 1 1 d . . . H5A H 0.4228 0.4297 0.6925 0.041 Uiso 1 1 calc R . . H5B H 0.3013 0.5707 0.7056 0.041 Uiso 1 1 calc R . . C6 C 0.4124(4) 0.6027(4) 0.64623(11) 0.0271(7) Uani 1 1 d . . . H6A H 0.5291 0.6303 0.6554 0.032 Uiso 1 1 calc R . . C7 C 0.3191(4) 0.7586(4) 0.63583(10) 0.0261(7) Uani 1 1 d . . . H7A H 0.1956 0.7381 0.6354 0.031 Uiso 1 1 calc R . . C8 C 0.3776(4) 0.7901(4) 0.59075(10) 0.0264(7) Uani 1 1 d . . . C9 C 0.3755(5) 0.9258(4) 0.56700(11) 0.0326(8) Uani 1 1 d . . . H9A H 0.3273 1.0186 0.5784 0.039 Uiso 1 1 calc R . . C10 C 0.4452(5) 0.9249(5) 0.52579(12) 0.0394(9) Uani 1 1 d . . . H10A H 0.4447 1.0178 0.5090 0.047 Uiso 1 1 calc R . . C11 C 0.5146(5) 0.7902(5) 0.50948(11) 0.0367(9) Uani 1 1 d . . . H11A H 0.5630 0.7901 0.4816 0.044 Uiso 1 1 calc R . . C12 C 0.5137(4) 0.6548(5) 0.53384(12) 0.0329(8) Uani 1 1 d . . . H12A H 0.5620 0.5610 0.5231 0.040 Uiso 1 1 calc R . . N1 N 0.4430(3) 0.6587(3) 0.57309(9) 0.0272(6) Uani 1 1 d . . . C13 C 0.3552(5) 0.8885(4) 0.66808(10) 0.0270(7) Uani 1 1 d . . . C14 C 0.5114(4) 0.9602(4) 0.66886(10) 0.0297(8) Uani 1 1 d . . . H14A H 0.5950 0.9283 0.6489 0.036 Uiso 1 1 calc R . . C15 C 0.5474(5) 1.0776(4) 0.69821(12) 0.0345(8) Uani 1 1 d . . . C16 C 0.4251(5) 1.1177(4) 0.72820(11) 0.0328(8) Uani 1 1 d . . . H16A H 0.4490 1.1965 0.7489 0.039 Uiso 1 1 calc R . . C17 C 0.2689(5) 1.0454(4) 0.72864(11) 0.0332(8) Uani 1 1 d . . . C18 C 0.2344(5) 0.9318(4) 0.69809(11) 0.0327(8) Uani 1 1 d . . . H18A H 0.1272 0.8831 0.6976 0.039 Uiso 1 1 calc R . . C19 C 0.7157(6) 1.1610(5) 0.69700(14) 0.0481(10) Uani 1 1 d . . . H19A H 0.7249 1.2210 0.6703 0.072 Uiso 1 1 calc R . . H19B H 0.8064 1.0836 0.6983 0.072 Uiso 1 1 calc R . . H19C H 0.7243 1.2321 0.7216 0.072 Uiso 1 1 calc R . . C20 C 0.1399(6) 1.0890(5) 0.76238(13) 0.0499(11) Uani 1 1 d . . . H20A H 0.1435 1.2021 0.7674 0.075 Uiso 1 1 calc R . . H20B H 0.1649 1.0336 0.7892 0.075 Uiso 1 1 calc R . . H20C H 0.0277 1.0594 0.7523 0.075 Uiso 1 1 calc R . . Br2 Br 0.86907(5) 0.71025(5) 0.602276(13) 0.03843(10) Uani 1 1 d . . . Br3 Br 0.85304(4) 1.00791(4) 0.584672(11) 0.03232(8) Uani 1 1 d . . . Br4 Br 0.81606(5) 1.29651(5) 0.572485(12) 0.04050(10) 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 C1 0.0315(17) 0.0266(17) 0.0234(16) 0.0027(14) -0.0008(14) 0.0034(14) C2 0.0340(18) 0.0273(16) 0.0223(17) -0.0029(13) -0.0032(14) 0.0045(14) Br1 0.0500(2) 0.03250(18) 0.02579(17) -0.00437(15) -0.00342(16) 0.00353(17) C3 0.0379(19) 0.0278(18) 0.0299(17) 0.0009(14) -0.0022(15) -0.0019(16) C4 0.043(2) 0.0295(17) 0.0268(18) 0.0035(14) -0.0001(16) 0.0006(17) C5 0.047(2) 0.0319(18) 0.0231(16) 0.0056(14) -0.0047(15) 0.0035(18) C6 0.0292(17) 0.0269(17) 0.0251(18) -0.0030(14) -0.0049(14) 0.0034(14) C7 0.0252(17) 0.0267(16) 0.0263(17) 0.0008(13) -0.0015(14) -0.0003(13) C8 0.0253(15) 0.0302(17) 0.0239(16) -0.0008(14) -0.0039(13) -0.0015(15) C9 0.041(2) 0.0333(18) 0.0238(17) 0.0018(14) -0.0018(16) -0.0010(17) C10 0.050(2) 0.039(2) 0.029(2) 0.0068(17) -0.0037(18) -0.0057(19) C11 0.043(2) 0.047(2) 0.0208(17) 0.0050(17) 0.0033(15) -0.0073(19) C12 0.0303(17) 0.041(2) 0.0276(18) -0.0036(17) 0.0037(15) 0.0002(16) N1 0.0231(13) 0.0323(15) 0.0261(15) 0.0030(12) -0.0031(12) -0.0003(12) C13 0.0323(18) 0.0282(17) 0.0206(16) 0.0023(13) -0.0043(15) 0.0022(15) C14 0.0340(18) 0.0349(19) 0.0201(16) -0.0007(14) 0.0026(14) 0.0042(15) C15 0.041(2) 0.035(2) 0.0277(19) 0.0010(16) -0.0069(16) -0.0006(17) C16 0.052(2) 0.0281(19) 0.0179(17) -0.0016(14) -0.0032(16) 0.0069(17) C17 0.045(2) 0.0335(18) 0.0214(16) 0.0021(14) 0.0026(15) 0.0115(17) C18 0.0321(19) 0.0348(19) 0.0311(19) 0.0044(15) 0.0025(15) 0.0056(16) C19 0.052(2) 0.052(2) 0.040(2) -0.0094(19) -0.001(2) -0.015(2) C20 0.062(3) 0.055(3) 0.033(2) -0.0022(19) 0.014(2) 0.016(2) Br2 0.03183(18) 0.0389(2) 0.0446(2) 0.00308(17) -0.00254(17) 0.00123(17) Br3 0.02762(16) 0.03968(19) 0.02965(17) -0.00180(15) 0.00087(14) 0.00175(15) Br4 0.0431(2) 0.0396(2) 0.0387(2) -0.00078(17) 0.00284(16) 0.00942(17) _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 C1 N1 1.488(4) . ? C1 C2 1.530(5) . ? C1 C6 1.539(5) . ? C1 H1A 1.0000 . ? C2 C3 1.515(4) . ? C2 Br1 1.963(3) . ? C2 H2A 1.0000 . ? C3 C4 1.535(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.521(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.522(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.559(4) . ? C6 H6A 1.0000 . ? C7 C8 1.502(4) . ? C7 C13 1.524(4) . ? C7 H7A 1.0000 . ? C8 N1 1.354(4) . ? C8 C9 1.375(5) . ? C9 C10 1.397(5) . ? C9 H9A 0.9500 . ? C10 C11 1.374(5) . ? C10 H10A 0.9500 . ? C11 C12 1.383(5) . ? C11 H11A 0.9500 . ? C12 N1 1.345(5) . ? C12 H12A 0.9500 . ? C13 C14 1.387(5) . ? C13 C18 1.391(5) . ? C14 C15 1.387(5) . ? C14 H14A 0.9500 . ? C15 C16 1.392(5) . ? C15 C19 1.518(6) . ? C16 C17 1.390(5) . ? C16 H16A 0.9500 . ? C17 C18 1.386(5) . ? C17 C20 1.516(5) . ? C18 H18A 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? Br2 Br3 2.6045(8) . ? Br3 Br4 2.5121(8) . ? 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 N1 C1 C2 110.3(3) . . ? N1 C1 C6 101.1(3) . . ? C2 C1 C6 112.0(3) . . ? N1 C1 H1A 111.0 . . ? C2 C1 H1A 111.0 . . ? C6 C1 H1A 111.0 . . ? C3 C2 C1 109.9(3) . . ? C3 C2 Br1 112.0(2) . . ? C1 C2 Br1 110.4(2) . . ? C3 C2 H2A 108.1 . . ? C1 C2 H2A 108.1 . . ? Br1 C2 H2A 108.1 . . ? C2 C3 C4 106.9(3) . . ? C2 C3 H3A 110.3 . . ? C4 C3 H3A 110.3 . . ? C2 C3 H3B 110.3 . . ? C4 C3 H3B 110.3 . . ? H3A C3 H3B 108.6 . . ? C5 C4 C3 110.3(3) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C4 C5 C6 114.0(3) . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? C6 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C5 C6 C1 114.4(3) . . ? C5 C6 C7 116.2(3) . . ? C1 C6 C7 103.3(3) . . ? C5 C6 H6A 107.5 . . ? C1 C6 H6A 107.5 . . ? C7 C6 H6A 107.5 . . ? C8 C7 C13 115.2(3) . . ? C8 C7 C6 101.5(3) . . ? C13 C7 C6 113.3(3) . . ? C8 C7 H7A 108.8 . . ? C13 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? N1 C8 C9 119.0(3) . . ? N1 C8 C7 110.5(3) . . ? C9 C8 C7 130.5(3) . . ? C8 C9 C10 118.9(4) . . ? C8 C9 H9A 120.5 . . ? C10 C9 H9A 120.5 . . ? C11 C10 C9 120.2(4) . . ? C11 C10 H10A 119.9 . . ? C9 C10 H10A 119.9 . . ? C10 C11 C12 119.8(3) . . ? C10 C11 H11A 120.1 . . ? C12 C11 H11A 120.1 . . ? N1 C12 C11 118.6(3) . . ? N1 C12 H12A 120.7 . . ? C11 C12 H12A 120.7 . . ? C12 N1 C8 123.4(3) . . ? C12 N1 C1 125.0(3) . . ? C8 N1 C1 111.6(3) . . ? C14 C13 C18 119.4(3) . . ? C14 C13 C7 120.1(3) . . ? C18 C13 C7 120.4(3) . . ? C13 C14 C15 121.1(3) . . ? C13 C14 H14A 119.4 . . ? C15 C14 H14A 119.4 . . ? C14 C15 C16 118.4(4) . . ? C14 C15 C19 120.4(4) . . ? C16 C15 C19 121.2(3) . . ? C17 C16 C15 121.6(3) . . ? C17 C16 H16A 119.2 . . ? C15 C16 H16A 119.2 . . ? C18 C17 C16 118.9(3) . . ? C18 C17 C20 120.8(4) . . ? C16 C17 C20 120.3(3) . . ? C17 C18 C13 120.6(3) . . ? C17 C18 H18A 119.7 . . ? C13 C18 H18A 119.7 . . ? C15 C19 H19A 109.5 . . ? C15 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C15 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? Br4 Br3 Br2 174.81(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 N1 C1 C2 C3 -168.1(3) . . . . ? C6 C1 C2 C3 -56.3(4) . . . . ? N1 C1 C2 Br1 67.9(3) . . . . ? C6 C1 C2 Br1 179.7(2) . . . . ? C1 C2 C3 C4 66.2(4) . . . . ? Br1 C2 C3 C4 -170.6(2) . . . . ? C2 C3 C4 C5 -63.7(4) . . . . ? C3 C4 C5 C6 52.0(4) . . . . ? C4 C5 C6 C1 -41.6(4) . . . . ? C4 C5 C6 C7 78.7(4) . . . . ? N1 C1 C6 C5 160.7(3) . . . . ? C2 C1 C6 C5 43.2(4) . . . . ? N1 C1 C6 C7 33.4(3) . . . . ? C2 C1 C6 C7 -84.0(3) . . . . ? C5 C6 C7 C8 -157.2(3) . . . . ? C1 C6 C7 C8 -31.1(3) . . . . ? C5 C6 C7 C13 78.6(4) . . . . ? C1 C6 C7 C13 -155.2(3) . . . . ? C13 C7 C8 N1 140.0(3) . . . . ? C6 C7 C8 N1 17.2(3) . . . . ? C13 C7 C8 C9 -39.0(5) . . . . ? C6 C7 C8 C9 -161.8(4) . . . . ? N1 C8 C9 C10 -1.8(5) . . . . ? C7 C8 C9 C10 177.2(3) . . . . ? C8 C9 C10 C11 0.0(6) . . . . ? C9 C10 C11 C12 0.6(6) . . . . ? C10 C11 C12 N1 0.5(6) . . . . ? C11 C12 N1 C8 -2.4(5) . . . . ? C11 C12 N1 C1 176.9(3) . . . . ? C9 C8 N1 C12 3.1(5) . . . . ? C7 C8 N1 C12 -176.1(3) . . . . ? C9 C8 N1 C1 -176.3(3) . . . . ? C7 C8 N1 C1 4.5(4) . . . . ? C2 C1 N1 C12 -85.1(4) . . . . ? C6 C1 N1 C12 156.2(3) . . . . ? C2 C1 N1 C8 94.2(3) . . . . ? C6 C1 N1 C8 -24.4(3) . . . . ? C8 C7 C13 C14 -44.8(4) . . . . ? C6 C7 C13 C14 71.4(4) . . . . ? C8 C7 C13 C18 137.8(3) . . . . ? C6 C7 C13 C18 -105.9(4) . . . . ? C18 C13 C14 C15 -2.0(5) . . . . ? C7 C13 C14 C15 -179.3(3) . . . . ? C13 C14 C15 C16 2.6(5) . . . . ? C13 C14 C15 C19 -176.6(3) . . . . ? C14 C15 C16 C17 -1.2(5) . . . . ? C19 C15 C16 C17 177.9(4) . . . . ? C15 C16 C17 C18 -0.7(5) . . . . ? C15 C16 C17 C20 178.5(3) . . . . ? C16 C17 C18 C13 1.4(5) . . . . ? C20 C17 C18 C13 -177.9(3) . . . . ? C14 C13 C18 C17 -0.1(5) . . . . ? C7 C13 C18 C17 177.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.629 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.075