data_07112a 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             07112a 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C13 H14 Br N O3' 
_chemical_formula_sum             'C13 H14 Br N O3' 
_chemical_formula_weight          312.16 
_chemical_absolute_configuration  rmad

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   'C2   '
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y, -z' 
 'x+1/2, y+1/2, z' 
 '-x+1/2, y+1/2, -z' 
 
_cell_length_a                    20.682(4) 
_cell_length_b                    5.9165(10) 
_cell_length_c                    11.670(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  115.333(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1290.6(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used    1656
_cell_measurement_theta_min        3.48
_cell_measurement_theta_max       26.67
_exptl_crystal_description       'Needle'
_exptl_crystal_colour            'Colorless'
_exptl_crystal_size_max           0.45 
_exptl_crystal_size_mid           0.15 
_exptl_crystal_size_min           0.13 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.607 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              632 
_exptl_absorpt_coefficient_mu     3.185 
_exptl_absorpt_correction_type    Multi-scan 
_exptl_absorpt_correction_T_min   0.3283 
_exptl_absorpt_correction_T_max   0.6823 
_exptl_absorpt_process_details    'SADABS (G. Sheldrick, 2003)' 
 
_exptl_special_details            'T. Lu / Prof. R. Hsung -  UW Madison' 
 
_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             6044 
_diffrn_reflns_av_R_equivalents   0.0338
_diffrn_reflns_av_sigmaI/netI     0.0645 
_diffrn_reflns_limit_h_min        -26 
_diffrn_reflns_limit_h_max        23 
_diffrn_reflns_limit_k_min        -7 
_diffrn_reflns_limit_k_max        7 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          1.93 
_diffrn_reflns_theta_max          27.06 
_reflns_number_total              2744 
_reflns_number_gt                 2344 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection      'Bruker SMART'
_computing_cell_refinement      'Bruker SMART'
_computing_data_reduction       'Bruker SAINT'
_computing_structure_solution   'SIR-2002'
_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^)+(0.0340P)^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     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    0.021(11) 
_refine_ls_number_reflns          2744 
_refine_ls_number_parameters      163 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0455 
_refine_ls_R_factor_gt            0.0352 
_refine_ls_wR_factor_ref          0.0830 
_refine_ls_wR_factor_gt           0.0791 
_refine_ls_goodness_of_fit_ref    0.977 
_refine_ls_restrained_S_all       0.977 
_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 
Br1 Br 0.580522(16) 0.49735(8) 0.63622(3) 0.03977(13) Uani 1 1 d . . . 
C1 C 0.68530(15) 0.5204(8) 0.7242(3) 0.0229(7) Uani 1 1 d . . . 
H1A H 0.7012 0.6007 0.8072 0.027 Uiso 1 1 calc R . . 
C2 C 0.71299(19) 0.6348(6) 0.6377(3) 0.0273(8) Uani 1 1 d . . . 
H2A H 0.6802 0.7559 0.5871 0.033 Uiso 1 1 calc R . . 
H2B H 0.7612 0.6997 0.6867 0.033 Uiso 1 1 calc R . . 
C3 C 0.7154(2) 0.4430(5) 0.5539(3) 0.0332(10) Uani 1 1 d . . . 
H3A H 0.6700 0.4348 0.4759 0.040 Uiso 1 1 calc R . . 
H3B H 0.7553 0.4645 0.5294 0.040 Uiso 1 1 calc R . . 
O1 O 0.72587(14) 0.2387(4) 0.6286(2) 0.0292(6) Uani 1 1 d . . . 
C4 C 0.71693(19) 0.2830(6) 0.7404(3) 0.0239(7) Uani 1 1 d . . . 
H4A H 0.6815 0.1731 0.7453 0.029 Uiso 1 1 calc R . . 
N1 N 0.78387(14) 0.2583(5) 0.8533(2) 0.0227(6) Uani 1 1 d . . . 
C5 C 0.7942(2) 0.0800(6) 0.9319(3) 0.0276(8) Uani 1 1 d . . . 
O2 O 0.75429(17) -0.0797(4) 0.9161(3) 0.0376(7) Uani 1 1 d . . . 
O3 O 0.85726(14) 0.0954(4) 1.0338(2) 0.0334(6) Uani 1 1 d . . . 
C6 C 0.8874(2) 0.3186(7) 1.0368(4) 0.0371(9) Uani 1 1 d . . . 
H6A H 0.9381 0.3069 1.0517 0.044 Uiso 1 1 calc R . . 
H6B H 0.8845 0.4117 1.1050 0.044 Uiso 1 1 calc R . . 
C7 C 0.84199(18) 0.4241(5) 0.9057(3) 0.0242(8) Uani 1 1 d . . . 
H7A H 0.8221 0.5719 0.9173 0.029 Uiso 1 1 calc R . . 
C8 C 0.88437(17) 0.4610(6) 0.8286(3) 0.0230(8) Uani 1 1 d . . . 
C9 C 0.91968(19) 0.6666(6) 0.8409(4) 0.0346(9) Uani 1 1 d . . . 
H9A H 0.9153 0.7809 0.8944 0.042 Uiso 1 1 calc R . . 
C10 C 0.9610(2) 0.7056(7) 0.7758(4) 0.0425(10) Uani 1 1 d . . . 
H10A H 0.9858 0.8448 0.7861 0.051 Uiso 1 1 calc R . . 
C11 C 0.9662(2) 0.5419(8) 0.6960(4) 0.0404(11) Uani 1 1 d . . . 
H11A H 0.9936 0.5701 0.6496 0.048 Uiso 1 1 calc R . . 
C12 C 0.9319(2) 0.3379(7) 0.6834(4) 0.0340(8) Uani 1 1 d . . . 
H12A H 0.9363 0.2243 0.6296 0.041 Uiso 1 1 calc R . . 
C13 C 0.8909(2) 0.2979(6) 0.7493(3) 0.0290(8) Uani 1 1 d . . . 
H13A H 0.8671 0.1572 0.7398 0.035 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 0.02259(18) 0.0599(2) 0.03589(19) 0.0070(2) 0.01157(14) 0.0010(2) 
C1 0.0164(14) 0.0296(19) 0.0210(13) -0.0027(16) 0.0065(12) 0.0018(16) 
C2 0.028(2) 0.0212(18) 0.033(2) 0.0054(15) 0.0136(17) 0.0016(14) 
C3 0.044(2) 0.035(3) 0.0272(17) 0.0074(14) 0.0209(17) 0.0056(15) 
O1 0.0420(15) 0.0225(13) 0.0223(12) -0.0013(10) 0.0130(12) 0.0038(11) 
C4 0.0267(19) 0.0206(17) 0.0249(17) 0.0003(13) 0.0114(15) -0.0030(13) 
N1 0.0253(15) 0.0197(13) 0.0234(14) 0.0025(11) 0.0106(13) -0.0029(11) 
C5 0.041(2) 0.0204(16) 0.0276(18) 0.0022(13) 0.0204(19) 0.0047(15) 
O2 0.061(2) 0.0194(13) 0.0344(14) 0.0030(10) 0.0216(15) -0.0046(12) 
O3 0.0404(16) 0.0308(13) 0.0263(13) 0.0080(10) 0.0117(12) 0.0076(11) 
C6 0.029(2) 0.051(3) 0.0271(19) 0.0063(17) 0.0085(17) -0.0039(17) 
C7 0.0238(18) 0.0237(18) 0.0239(16) -0.0028(12) 0.0092(15) -0.0024(11) 
C8 0.0180(15) 0.023(2) 0.0236(14) 0.0019(14) 0.0045(13) 0.0000(14) 
C9 0.039(2) 0.0206(18) 0.051(3) 0.0006(16) 0.025(2) -0.0017(16) 
C10 0.040(2) 0.031(2) 0.061(3) 0.0084(19) 0.027(2) -0.0037(17) 
C11 0.035(2) 0.051(3) 0.040(2) 0.018(2) 0.0207(18) 0.0060(19) 
C12 0.025(2) 0.045(2) 0.031(2) -0.0027(17) 0.0107(18) 0.0004(17) 
C13 0.029(2) 0.0251(18) 0.0329(19) -0.0006(15) 0.0128(17) -0.0013(14) 
 
_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 C1 1.966(3) . ? 
C1 C2 1.517(5) . ? 
C1 C4 1.526(5) . ? 
C1 H1A 1.0000 . ? 
C2 C3 1.512(5) . ? 
C2 H2A 0.9900 . ? 
C2 H2B 0.9900 . ? 
C3 O1 1.451(4) . ? 
C3 H3A 0.9900 . ? 
C3 H3B 0.9900 . ? 
O1 C4 1.418(4) . ? 
C4 N1 1.454(4) . ? 
C4 H4A 1.0000 . ? 
N1 C5 1.354(4) . ? 
N1 C7 1.467(4) . ? 
C5 O2 1.215(4) . ? 
C5 O3 1.340(5) . ? 
O3 C6 1.455(5) . ? 
C6 C7 1.543(5) . ? 
C6 H6A 0.9900 . ? 
C6 H6B 0.9900 . ? 
C7 C8 1.516(4) . ? 
C7 H7A 1.0000 . ? 
C8 C13 1.384(5) . ? 
C8 C9 1.394(5) . ? 
C9 C10 1.385(5) . ? 
C9 H9A 0.9500 . ? 
C10 C11 1.380(6) . ? 
C10 H10A 0.9500 . ? 
C11 C12 1.376(6) . ? 
C11 H11A 0.9500 . ? 
C12 C13 1.387(5) . ? 
C12 H12A 0.9500 . ? 
C13 H13A 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 C1 C4 103.3(3) . . ? 
C2 C1 Br1 109.2(2) . . ? 
C4 C1 Br1 108.6(3) . . ? 
C2 C1 H1A 111.8 . . ? 
C4 C1 H1A 111.8 . . ? 
Br1 C1 H1A 111.8 . . ? 
C3 C2 C1 102.8(3) . . ? 
C3 C2 H2A 111.2 . . ? 
C1 C2 H2A 111.2 . . ? 
C3 C2 H2B 111.2 . . ? 
C1 C2 H2B 111.2 . . ? 
H2A C2 H2B 109.1 . . ? 
O1 C3 C2 105.9(3) . . ? 
O1 C3 H3A 110.6 . . ? 
C2 C3 H3A 110.6 . . ? 
O1 C3 H3B 110.6 . . ? 
C2 C3 H3B 110.6 . . ? 
H3A C3 H3B 108.7 . . ? 
C4 O1 C3 110.7(2) . . ? 
O1 C4 N1 111.5(3) . . ? 
O1 C4 C1 105.9(3) . . ? 
N1 C4 C1 113.3(3) . . ? 
O1 C4 H4A 108.7 . . ? 
N1 C4 H4A 108.7 . . ? 
C1 C4 H4A 108.7 . . ? 
C5 N1 C4 120.3(3) . . ? 
C5 N1 C7 112.1(3) . . ? 
C4 N1 C7 127.1(3) . . ? 
O2 C5 O3 121.8(3) . . ? 
O2 C5 N1 127.1(4) . . ? 
O3 C5 N1 111.1(3) . . ? 
C5 O3 C6 109.1(3) . . ? 
O3 C6 C7 105.7(3) . . ? 
O3 C6 H6A 110.6 . . ? 
C7 C6 H6A 110.6 . . ? 
O3 C6 H6B 110.6 . . ? 
C7 C6 H6B 110.6 . . ? 
H6A C6 H6B 108.7 . . ? 
N1 C7 C8 115.3(3) . . ? 
N1 C7 C6 100.7(3) . . ? 
C8 C7 C6 112.7(3) . . ? 
N1 C7 H7A 109.3 . . ? 
C8 C7 H7A 109.3 . . ? 
C6 C7 H7A 109.3 . . ? 
C13 C8 C9 118.7(3) . . ? 
C13 C8 C7 122.9(3) . . ? 
C9 C8 C7 118.4(3) . . ? 
C10 C9 C8 120.5(4) . . ? 
C10 C9 H9A 119.7 . . ? 
C8 C9 H9A 119.7 . . ? 
C11 C10 C9 119.9(4) . . ? 
C11 C10 H10A 120.0 . . ? 
C9 C10 H10A 120.0 . . ? 
C12 C11 C10 120.1(3) . . ? 
C12 C11 H11A 119.9 . . ? 
C10 C11 H11A 119.9 . . ? 
C11 C12 C13 120.0(4) . . ? 
C11 C12 H12A 120.0 . . ? 
C13 C12 H12A 120.0 . . ? 
C8 C13 C12 120.7(3) . . ? 
C8 C13 H13A 119.7 . . ? 
C12 C13 H13A 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 
C4 C1 C2 C3 33.5(3) . . . . ? 
Br1 C1 C2 C3 -81.9(3) . . . . ? 
C1 C2 C3 O1 -27.7(4) . . . . ? 
C2 C3 O1 C4 10.8(4) . . . . ? 
C3 O1 C4 N1 -112.9(3) . . . . ? 
C3 O1 C4 C1 10.8(4) . . . . ? 
C2 C1 C4 O1 -27.9(3) . . . . ? 
Br1 C1 C4 O1 88.0(2) . . . . ? 
C2 C1 C4 N1 94.7(3) . . . . ? 
Br1 C1 C4 N1 -149.4(2) . . . . ? 
O1 C4 N1 C5 -108.1(3) . . . . ? 
C1 C4 N1 C5 132.6(3) . . . . ? 
O1 C4 N1 C7 80.6(4) . . . . ? 
C1 C4 N1 C7 -38.8(4) . . . . ? 
C4 N1 C5 O2 5.0(5) . . . . ? 
C7 N1 C5 O2 177.6(3) . . . . ? 
C4 N1 C5 O3 -176.3(3) . . . . ? 
C7 N1 C5 O3 -3.8(4) . . . . ? 
O2 C5 O3 C6 -171.0(3) . . . . ? 
N1 C5 O3 C6 10.3(4) . . . . ? 
C5 O3 C6 C7 -12.3(4) . . . . ? 
C5 N1 C7 C8 117.7(3) . . . . ? 
C4 N1 C7 C8 -70.4(4) . . . . ? 
C5 N1 C7 C6 -3.8(3) . . . . ? 
C4 N1 C7 C6 168.1(3) . . . . ? 
O3 C6 C7 N1 9.3(3) . . . . ? 
O3 C6 C7 C8 -114.1(3) . . . . ? 
N1 C7 C8 C13 -26.3(5) . . . . ? 
C6 C7 C8 C13 88.5(4) . . . . ? 
N1 C7 C8 C9 155.3(3) . . . . ? 
C6 C7 C8 C9 -89.9(4) . . . . ? 
C13 C8 C9 C10 -0.6(6) . . . . ? 
C7 C8 C9 C10 177.8(4) . . . . ? 
C8 C9 C10 C11 1.4(6) . . . . ? 
C9 C10 C11 C12 -1.7(6) . . . . ? 
C10 C11 C12 C13 1.2(6) . . . . ? 
C9 C8 C13 C12 0.1(5) . . . . ? 
C7 C8 C13 C12 -178.2(3) . . . . ? 
C11 C12 C13 C8 -0.4(6) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.986 
_diffrn_reflns_theta_full              27.06 
_diffrn_measured_fraction_theta_full   0.986 
_refine_diff_density_max    0.794 
_refine_diff_density_min   -0.486 
_refine_diff_density_rms    0.077