data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H19 Br2 N O3' _chemical_formula_sum 'C16 H19 Br2 N O3' _chemical_formula_weight 433.14 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 Monoclinic _symmetry_space_group_name_H-M P21/c 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 10.361(2) _cell_length_b 15.234(3) _cell_length_c 10.793(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.876(5) _cell_angle_gamma 90.00 _cell_volume 1703.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4051 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description prisms _exptl_crystal_colour colorless _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.689 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 4.770 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.504 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku SCX-Mini with Mercury 2 CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17619 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3895 _reflns_number_gt 3548 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. An Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-ray Diffraction Data. Sheldrick, G. M. (2008). SHELXL-97. Acta Cryst., A64, 112-122. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _publ_section_acknowledgements ; The data were collected using instrumentation purchased with funds provided by the National Science Foundation Grant No. 0741973. ; _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material 'XP SHELXTL/PC, Siemens Analytical' _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^)+(0.0302P)^2^+0.8687P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3895 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0706 _refine_ls_wR_factor_gt 0.0686 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.001 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 0.77355(19) 0.42911(13) 0.34107(19) 0.0201(4) Uani 1 1 d . . . C2 C 0.8242(2) 0.37849(15) 0.4582(2) 0.0270(5) Uani 1 1 d . . . H2A H 0.8958 0.3386 0.4367 0.032 Uiso 1 1 calc R . . H2B H 0.8547 0.4199 0.5230 0.032 Uiso 1 1 calc R . . C3 C 0.7067(3) 0.32647(16) 0.5023(2) 0.0366(6) Uani 1 1 d . . . H3A H 0.7333 0.2714 0.5441 0.044 Uiso 1 1 calc R . . H3B H 0.6538 0.3617 0.5594 0.044 Uiso 1 1 calc R . . C4 C 0.6341(3) 0.30784(17) 0.3815(2) 0.0363(6) Uani 1 1 d . . . H4A H 0.6753 0.2598 0.3347 0.044 Uiso 1 1 calc R . . H4B H 0.5429 0.2924 0.3966 0.044 Uiso 1 1 calc R . . C5 C 0.8629(2) 0.41155(14) 0.2324(2) 0.0231(4) Uani 1 1 d . . . C6 C 1.0745(2) 0.4308(2) 0.1581(3) 0.0461(7) Uani 1 1 d . . . H6A H 1.0977 0.3686 0.1525 0.069 Uiso 1 1 calc R . . H6B H 1.1521 0.4655 0.1765 0.069 Uiso 1 1 calc R . . H6C H 1.0363 0.4501 0.0791 0.069 Uiso 1 1 calc R . . C7 C 0.76877(19) 0.53105(13) 0.36446(18) 0.0193(4) Uani 1 1 d . . . H7 H 0.8573 0.5501 0.3910 0.023 Uiso 1 1 calc R . . C8 C 0.6783(2) 0.55244(14) 0.4685(2) 0.0260(5) Uani 1 1 d . . . H8 H 0.5887 0.5426 0.4551 0.031 Uiso 1 1 calc R . . C9 C 0.7163(3) 0.58387(17) 0.5767(2) 0.0406(6) Uani 1 1 d . . . H9A H 0.8054 0.5944 0.5929 0.049 Uiso 1 1 calc R . . H9B H 0.6546 0.5960 0.6386 0.049 Uiso 1 1 calc R . . C10 C 0.73311(19) 0.58168(12) 0.24731(18) 0.0176(4) Uani 1 1 d . . . C11 C 0.81576(19) 0.63944(13) 0.18700(19) 0.0202(4) Uani 1 1 d . . . C12 C 0.7805(2) 0.68154(13) 0.07715(19) 0.0210(4) Uani 1 1 d . . . H12 H 0.8393 0.7200 0.0377 0.025 Uiso 1 1 calc R . . C13 C 0.6583(2) 0.66678(12) 0.02548(17) 0.0182(4) Uani 1 1 d . . . C14 C 0.57006(19) 0.61271(13) 0.08571(18) 0.0186(4) Uani 1 1 d . . . C15 C 0.60824(19) 0.57112(12) 0.19528(18) 0.0179(4) Uani 1 1 d . . . H15 H 0.5483 0.5345 0.2363 0.022 Uiso 1 1 calc R . . C16 C 0.3536(2) 0.56061(15) 0.1010(2) 0.0259(5) Uani 1 1 d . . . H16A H 0.3776 0.4990 0.1141 0.039 Uiso 1 1 calc R . . H16B H 0.2711 0.5636 0.0557 0.039 Uiso 1 1 calc R . . H16C H 0.3453 0.5899 0.1814 0.039 Uiso 1 1 calc R . . N1 N 0.64448(17) 0.39233(12) 0.31538(19) 0.0246(4) Uani 1 1 d . . . O1 O 0.83288(17) 0.37464(13) 0.13795(15) 0.0396(4) Uani 1 1 d . . . O2 O 0.98209(14) 0.44284(12) 0.25589(14) 0.0313(4) Uani 1 1 d . . . O3 O 0.45144(13) 0.60355(10) 0.03070(13) 0.0232(3) Uani 1 1 d . . . Br1 Br 0.98124(2) 0.670743(16) 0.25495(2) 0.03431(8) Uani 1 1 d . . . Br2 Br 0.61220(2) 0.718970(14) -0.127758(18) 0.02477(8) Uani 1 1 d . . . H1N H 0.632(2) 0.3869(17) 0.241(3) 0.028(7) Uiso 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 0.0171(9) 0.0209(10) 0.0224(10) 0.0036(8) 0.0010(8) 0.0007(8) C2 0.0258(11) 0.0296(11) 0.0257(11) 0.0082(9) 0.0003(9) 0.0052(9) C3 0.0391(14) 0.0340(13) 0.0367(14) 0.0165(10) 0.0042(11) -0.0004(11) C4 0.0350(13) 0.0270(12) 0.0469(16) 0.0136(11) -0.0013(11) -0.0060(11) C5 0.0214(10) 0.0229(10) 0.0250(11) 0.0042(8) 0.0010(8) 0.0064(8) C6 0.0285(13) 0.0679(19) 0.0426(16) 0.0104(13) 0.0196(11) 0.0093(13) C7 0.0168(9) 0.0220(10) 0.0191(10) 0.0014(8) 0.0020(7) -0.0003(8) C8 0.0294(11) 0.0258(11) 0.0229(11) 0.0054(8) 0.0066(8) 0.0061(9) C9 0.0546(16) 0.0426(15) 0.0247(12) -0.0019(10) 0.0065(11) 0.0117(13) C10 0.0192(9) 0.0147(9) 0.0190(10) -0.0022(7) 0.0042(7) 0.0021(7) C11 0.0173(9) 0.0208(10) 0.0225(10) -0.0038(8) 0.0026(8) -0.0016(8) C12 0.0213(10) 0.0170(9) 0.0247(11) 0.0005(8) 0.0066(8) -0.0019(8) C13 0.0245(10) 0.0161(9) 0.0141(9) 0.0014(7) 0.0053(7) 0.0014(8) C14 0.0180(9) 0.0164(9) 0.0215(10) -0.0023(7) 0.0025(7) 0.0023(8) C15 0.0171(9) 0.0166(9) 0.0202(10) -0.0007(7) 0.0053(7) -0.0007(8) C16 0.0183(10) 0.0306(12) 0.0289(12) 0.0048(9) 0.0031(8) -0.0034(9) N1 0.0210(9) 0.0227(9) 0.0300(11) 0.0061(8) -0.0010(8) -0.0041(7) O1 0.0362(10) 0.0521(11) 0.0304(9) -0.0130(8) -0.0002(7) 0.0066(8) O2 0.0200(8) 0.0420(10) 0.0321(9) -0.0007(7) 0.0092(6) -0.0005(7) O3 0.0185(7) 0.0275(8) 0.0236(8) 0.0055(6) -0.0012(6) -0.0035(6) Br1 0.02458(13) 0.03824(15) 0.03989(15) 0.00957(10) -0.00643(10) -0.01363(10) Br2 0.03121(13) 0.02459(12) 0.01859(12) 0.00489(7) 0.00284(8) -0.00135(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 C1 N1 1.472(3) . ? C1 C5 1.529(3) . ? C1 C2 1.564(3) . ? C1 C7 1.574(3) . ? C2 C3 1.534(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.522(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N1 1.476(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O1 1.201(3) . ? C5 O2 1.344(3) . ? C6 O2 1.447(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.509(3) . ? C7 C10 1.522(3) . ? C7 H7 1.0000 . ? C8 C9 1.317(3) . ? C8 H8 0.9500 . ? C9 H9A 0.9500 . ? C9 H9B 0.9500 . ? C10 C11 1.396(3) . ? C10 C15 1.412(3) . ? C11 C12 1.392(3) . ? C11 Br1 1.915(2) . ? C12 C13 1.394(3) . ? C12 H12 0.9500 . ? C13 C14 1.399(3) . ? C13 Br2 1.8899(19) . ? C14 O3 1.364(2) . ? C14 C15 1.394(3) . ? C15 H15 0.9500 . ? C16 O3 1.433(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N1 H1N 0.81(3) . ? 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 C5 110.36(17) . . ? N1 C1 C2 104.89(16) . . ? C5 C1 C2 109.52(16) . . ? N1 C1 C7 112.02(16) . . ? C5 C1 C7 108.45(16) . . ? C2 C1 C7 111.57(17) . . ? C3 C2 C1 104.34(17) . . ? C3 C2 H2A 110.9 . . ? C1 C2 H2A 110.9 . . ? C3 C2 H2B 110.9 . . ? C1 C2 H2B 110.9 . . ? H2A C2 H2B 108.9 . . ? C4 C3 C2 102.41(19) . . ? C4 C3 H3A 111.3 . . ? C2 C3 H3A 111.3 . . ? C4 C3 H3B 111.3 . . ? C2 C3 H3B 111.3 . . ? H3A C3 H3B 109.2 . . ? N1 C4 C3 102.3(2) . . ? N1 C4 H4A 111.3 . . ? C3 C4 H4A 111.3 . . ? N1 C4 H4B 111.3 . . ? C3 C4 H4B 111.3 . . ? H4A C4 H4B 109.2 . . ? O1 C5 O2 123.5(2) . . ? O1 C5 C1 125.5(2) . . ? O2 C5 C1 111.03(18) . . ? O2 C6 H6A 109.5 . . ? O2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C10 111.31(16) . . ? C8 C7 C1 110.72(17) . . ? C10 C7 C1 112.00(16) . . ? C8 C7 H7 107.5 . . ? C10 C7 H7 107.5 . . ? C1 C7 H7 107.5 . . ? C9 C8 C7 123.9(2) . . ? C9 C8 H8 118.0 . . ? C7 C8 H8 118.0 . . ? C8 C9 H9A 120.0 . . ? C8 C9 H9B 120.0 . . ? H9A C9 H9B 120.0 . . ? C11 C10 C15 116.83(18) . . ? C11 C10 C7 124.34(18) . . ? C15 C10 C7 118.83(17) . . ? C12 C11 C10 122.21(18) . . ? C12 C11 Br1 115.67(15) . . ? C10 C11 Br1 122.04(15) . . ? C11 C12 C13 119.43(18) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C12 C13 C14 120.36(18) . . ? C12 C13 Br2 119.90(15) . . ? C14 C13 Br2 119.74(15) . . ? O3 C14 C15 124.41(18) . . ? O3 C14 C13 116.70(17) . . ? C15 C14 C13 118.88(18) . . ? C14 C15 C10 122.16(18) . . ? C14 C15 H15 118.9 . . ? C10 C15 H15 118.9 . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C1 N1 C4 108.27(17) . . ? C1 N1 H1N 110.8(18) . . ? C4 N1 H1N 112.0(18) . . ? C5 O2 C6 115.70(19) . . ? C14 O3 C16 117.12(16) . . ? 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 -9.2(2) . . . . ? C5 C1 C2 C3 -127.6(2) . . . . ? C7 C1 C2 C3 112.3(2) . . . . ? C1 C2 C3 C4 31.3(2) . . . . ? C2 C3 C4 N1 -41.9(2) . . . . ? N1 C1 C5 O1 1.4(3) . . . . ? C2 C1 C5 O1 116.3(2) . . . . ? C7 C1 C5 O1 -121.7(2) . . . . ? N1 C1 C5 O2 -178.44(16) . . . . ? C2 C1 C5 O2 -63.5(2) . . . . ? C7 C1 C5 O2 58.5(2) . . . . ? N1 C1 C7 C8 56.2(2) . . . . ? C5 C1 C7 C8 178.22(17) . . . . ? C2 C1 C7 C8 -61.1(2) . . . . ? N1 C1 C7 C10 -68.7(2) . . . . ? C5 C1 C7 C10 53.3(2) . . . . ? C2 C1 C7 C10 174.06(16) . . . . ? C10 C7 C8 C9 -122.5(2) . . . . ? C1 C7 C8 C9 112.2(2) . . . . ? C8 C7 C10 C11 121.2(2) . . . . ? C1 C7 C10 C11 -114.3(2) . . . . ? C8 C7 C10 C15 -58.2(2) . . . . ? C1 C7 C10 C15 66.4(2) . . . . ? C15 C10 C11 C12 -3.3(3) . . . . ? C7 C10 C11 C12 177.31(18) . . . . ? C15 C10 C11 Br1 173.20(14) . . . . ? C7 C10 C11 Br1 -6.2(3) . . . . ? C10 C11 C12 C13 0.7(3) . . . . ? Br1 C11 C12 C13 -175.99(15) . . . . ? C11 C12 C13 C14 2.3(3) . . . . ? C11 C12 C13 Br2 -176.92(15) . . . . ? C12 C13 C14 O3 178.29(17) . . . . ? Br2 C13 C14 O3 -2.4(2) . . . . ? C12 C13 C14 C15 -2.6(3) . . . . ? Br2 C13 C14 C15 176.64(14) . . . . ? O3 C14 C15 C10 178.90(18) . . . . ? C13 C14 C15 C10 -0.1(3) . . . . ? C11 C10 C15 C14 3.0(3) . . . . ? C7 C10 C15 C14 -177.59(17) . . . . ? C5 C1 N1 C4 100.3(2) . . . . ? C2 C1 N1 C4 -17.6(2) . . . . ? C7 C1 N1 C4 -138.80(19) . . . . ? C3 C4 N1 C1 37.6(2) . . . . ? O1 C5 O2 C6 1.0(3) . . . . ? C1 C5 O2 C6 -179.21(19) . . . . ? C15 C14 O3 C16 11.1(3) . . . . ? C13 C14 O3 C16 -169.91(18) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.427 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.080