data_publication_text _publ_requested_journal J.Org.Chem. _publ_contact_author_name 'Professor Shahriar Mobashery' _publ_contact_author_address ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; _publ_contact_author_email mobashery@nd.edu _publ_contact_author_phone 1(574)6312933 _publ_contact_author_fax 1(574)6316652 loop_ _publ_author_name _publ_author_address 'Hesek, Dusan' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Lee, Mijoon' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Noll, Bruce C.' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Fisher, Jed F.' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; ' Mobashery, Shahriar' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; data_compound_3 # local ID: dh47_1_0ma _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H20 N, Br' _chemical_formula_sum 'C16 H20 Br N' _chemical_formula_weight 306.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.9824(3) _cell_length_b 10.2376(2) _cell_length_c 10.7952(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.4850(10) _cell_angle_gamma 90.00 _cell_volume 1434.29(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9966 _cell_measurement_theta_min 3.4053 _cell_measurement_theta_max 69.2364 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'clear colorless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 3.744 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.31 _exptl_absorpt_correction_T_max 0.68 _exptl_absorpt_process_details 'Sheldrick, G. M. (2008) SADABS. University of G\"ottingen, Germany.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Siemens KFFCU2K-90' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_reflns_number 17289 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0146 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 69.70 _reflns_number_total 2579 _reflns_number_gt 2521 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Bruker-Nonius AXS. (2007). APEX2 and SAINT. Bruker-Nonius AXS, Madison, Wisconsin, USA. CCDC. (2005). enCIFer. The Cambridge Crystallographic Data Centre, Cambridge, UK. Sheldrick, G. M. (2007). SADABS. University of G\"ottingen, Germany. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2007; Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material 'XCIF (Sheldrick, 2008)/enCIFer (CCDC, 2005)' _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^)+(0.0267P)^2^+0.9166P] 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_number_reflns 2579 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0215 _refine_ls_R_factor_gt 0.0209 _refine_ls_wR_factor_ref 0.0538 _refine_ls_wR_factor_gt 0.0534 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 0.712740(12) 0.051414(15) 0.434127(14) 0.02031(8) Uani 1 1 d . . . N1 N 0.80445(10) 0.40762(13) 0.57019(11) 0.0152(3) Uani 1 1 d . . . C1 C 0.54844(13) 0.64259(19) 0.27905(19) 0.0333(4) Uani 1 1 d . . . H1 H 0.5184 0.6959 0.2184 0.040 Uiso 1 1 calc R . . C2 C 0.56813(13) 0.69171(18) 0.39658(19) 0.0320(4) Uani 1 1 d . . . H2 H 0.5519 0.7780 0.4146 0.038 Uiso 1 1 calc R . . C3 C 0.61231(12) 0.61192(17) 0.48797(17) 0.0255(4) Uani 1 1 d . . . H3 H 0.6240 0.6444 0.5676 0.031 Uiso 1 1 calc R . . C4 C 0.63912(11) 0.48335(16) 0.46041(15) 0.0190(3) Uani 1 1 d . . . C5 C 0.68661(11) 0.39496(15) 0.55795(14) 0.0180(3) Uani 1 1 d . . . H5A H 0.6693 0.3051 0.5378 0.022 Uiso 1 1 calc R . . H5B H 0.6569 0.4151 0.6372 0.022 Uiso 1 1 calc R . . C6 C 0.84010(12) 0.30396(15) 0.66432(14) 0.0170(3) Uani 1 1 d . . . H6A H 0.8007 0.3136 0.7389 0.020 Uiso 1 1 calc R . . H6B H 0.8254 0.2181 0.6303 0.020 Uiso 1 1 calc R . . C7 C 0.95321(12) 0.31219(14) 0.69826(14) 0.0170(3) Uani 1 1 d . . . C8 C 1.02636(13) 0.24376(15) 0.63108(15) 0.0205(3) Uani 1 1 d . . . H8 H 1.0049 0.1905 0.5655 0.025 Uiso 1 1 calc R . . C9 C 1.13067(13) 0.25435(16) 0.66108(16) 0.0241(4) Uani 1 1 d . . . H9 H 1.1787 0.2092 0.6151 0.029 Uiso 1 1 calc R . . C10 C 1.16312(13) 0.33238(16) 0.75969(16) 0.0244(4) Uani 1 1 d . . . H10 H 1.2330 0.3401 0.7794 0.029 Uiso 1 1 calc R . . C11 C 0.61902(13) 0.43524(17) 0.34158(17) 0.0231(4) Uani 1 1 d . . . H11 H 0.6363 0.3495 0.3227 0.028 Uiso 1 1 calc R . . C12 C 0.57328(13) 0.5142(2) 0.25091(18) 0.0298(4) Uani 1 1 d . . . H12 H 0.5594 0.4813 0.1719 0.036 Uiso 1 1 calc R . . C13 C 1.09118(13) 0.39920(16) 0.82920(15) 0.0225(3) Uani 1 1 d . . . H13 H 1.1129 0.4506 0.8959 0.027 Uiso 1 1 calc R . . C14 C 0.98696(12) 0.38897(15) 0.79868(14) 0.0194(3) Uani 1 1 d . . . H14 H 0.9391 0.4336 0.8454 0.023 Uiso 1 1 calc R . . C15 C 0.85302(12) 0.38317(15) 0.44836(14) 0.0181(3) Uani 1 1 d . . . H15A H 0.8301 0.4482 0.3898 0.027 Uiso 1 1 calc R . . H15B H 0.8335 0.2981 0.4186 0.027 Uiso 1 1 calc R . . H15C H 0.9266 0.3875 0.4585 0.027 Uiso 1 1 calc R . . C16 C 0.83147(13) 0.54101(14) 0.61675(16) 0.0192(3) Uani 1 1 d . . . H16A H 0.9049 0.5483 0.6268 0.029 Uiso 1 1 calc R . . H16B H 0.8000 0.5552 0.6951 0.029 Uiso 1 1 calc R . . H16C H 0.8069 0.6052 0.5583 0.029 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 Br1 0.02237(11) 0.01810(11) 0.02060(11) -0.00034(5) 0.00312(6) -0.00112(6) N1 0.0161(6) 0.0143(6) 0.0151(7) 0.0003(5) 0.0013(5) -0.0017(5) C1 0.0168(8) 0.0380(10) 0.0451(12) 0.0200(9) 0.0006(7) 0.0006(8) C2 0.0188(8) 0.0234(9) 0.0538(12) 0.0076(8) 0.0041(8) 0.0032(7) C3 0.0170(8) 0.0235(9) 0.0362(10) -0.0020(7) 0.0032(7) -0.0001(6) C4 0.0111(7) 0.0201(8) 0.0260(9) 0.0013(6) 0.0024(6) -0.0017(6) C5 0.0151(7) 0.0184(8) 0.0206(8) -0.0013(6) 0.0032(6) -0.0030(6) C6 0.0208(8) 0.0156(7) 0.0146(8) 0.0031(6) 0.0017(6) -0.0018(6) C7 0.0201(8) 0.0144(7) 0.0167(8) 0.0046(6) 0.0021(6) -0.0005(6) C8 0.0282(9) 0.0154(7) 0.0179(8) 0.0049(6) 0.0027(6) 0.0032(6) C9 0.0233(8) 0.0207(8) 0.0288(9) 0.0112(6) 0.0080(6) 0.0068(7) C10 0.0181(8) 0.0214(8) 0.0337(10) 0.0148(7) -0.0008(6) -0.0011(6) C11 0.0169(8) 0.0248(9) 0.0275(10) 0.0005(6) 0.0003(6) -0.0030(6) C12 0.0179(8) 0.0424(11) 0.0290(10) 0.0069(8) -0.0012(7) -0.0048(8) C13 0.0252(8) 0.0195(8) 0.0224(9) 0.0068(6) -0.0036(6) -0.0051(7) C14 0.0223(8) 0.0177(8) 0.0181(8) 0.0032(6) 0.0015(6) 0.0000(6) C15 0.0184(7) 0.0207(8) 0.0152(8) 0.0010(6) 0.0029(6) 0.0009(6) C16 0.0209(8) 0.0144(7) 0.0224(9) -0.0010(6) -0.0004(6) -0.0036(6) _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 C16 1.4939(19) . ? N1 C15 1.4943(18) . ? N1 C6 1.5325(19) . ? N1 C5 1.5376(19) . ? C1 C2 1.383(3) . ? C1 C12 1.388(3) . ? C1 H1 0.9300 . ? C2 C3 1.393(3) . ? C2 H2 0.9300 . ? C3 C4 1.396(2) . ? C3 H3 0.9300 . ? C4 C11 1.392(2) . ? C4 C5 1.508(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.506(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.398(2) . ? C7 C14 1.400(2) . ? C8 C9 1.388(2) . ? C8 H8 0.9300 . ? C9 C10 1.388(3) . ? C9 H9 0.9300 . ? C10 C13 1.393(2) . ? C10 H10 0.9300 . ? C11 C12 1.391(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.388(2) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 C16 N1 C15 110.40(12) . . ? C16 N1 C6 110.22(11) . . ? C15 N1 C6 109.91(11) . . ? C16 N1 C5 109.29(12) . . ? C15 N1 C5 110.60(11) . . ? C6 N1 C5 106.34(11) . . ? C2 C1 C12 120.43(17) . . ? C2 C1 H1 119.8 . . ? C12 C1 H1 119.8 . . ? C1 C2 C3 119.98(17) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C2 C3 C4 120.16(17) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C11 C4 C3 119.23(16) . . ? C11 C4 C5 119.63(15) . . ? C3 C4 C5 121.12(15) . . ? C4 C5 N1 113.41(12) . . ? C4 C5 H5A 108.9 . . ? N1 C5 H5A 108.9 . . ? C4 C5 H5B 108.9 . . ? N1 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C7 C6 N1 113.47(12) . . ? C7 C6 H6A 108.9 . . ? N1 C6 H6A 108.9 . . ? C7 C6 H6B 108.9 . . ? N1 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? C8 C7 C14 118.67(15) . . ? C8 C7 C6 121.11(14) . . ? C14 C7 C6 120.21(14) . . ? C9 C8 C7 120.76(16) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C10 C9 C8 119.92(15) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C13 120.11(15) . . ? C9 C10 H10 119.9 . . ? C13 C10 H10 119.9 . . ? C12 C11 C4 120.60(17) . . ? C12 C11 H11 119.7 . . ? C4 C11 H11 119.7 . . ? C1 C12 C11 119.58(18) . . ? C1 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C14 C13 C10 119.88(16) . . ? C14 C13 H13 120.1 . . ? C10 C13 H13 120.1 . . ? C13 C14 C7 120.64(15) . . ? C13 C14 H14 119.7 . . ? C7 C14 H14 119.7 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 69.70 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.323 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.048 _chemical_compound_source synthesized