  
data_cd21226 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C16 H14 Br N O3' 
_chemical_formula_weight          348.19 
  
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    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                    9.5280(6) 
_cell_length_b                    9.6271(6) 
_cell_length_c                    16.3779(10) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1502.30(16) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     2156 
_cell_measurement_theta_min       4.908 
_cell_measurement_theta_max       51.438 
  
_exptl_crystal_description        prismatic 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.211 
_exptl_crystal_size_mid           0.157 
_exptl_crystal_size_min           0.104 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.539 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              704 
_exptl_absorpt_coefficient_mu     2.745 
_exptl_absorpt_correction_type    empirical 
_exptl_absorpt_correction_T_min   0.62554 
_exptl_absorpt_correction_T_max   1.00000 
_exptl_absorpt_process_details    sadabs 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus 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             8593 
_diffrn_reflns_av_R_equivalents   0.0283 
_diffrn_reflns_av_sigmaI/netI     0.0563 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        10 
_diffrn_reflns_limit_l_min        -20 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          2.45 
_diffrn_reflns_theta_max          26.00 
_reflns_number_total              2946 
_reflns_number_gt                 2176 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SHELXTL' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0160P)²+0.4554P] where P=(Fo²+2Fc²)/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      SHELXL 
_refine_ls_extinction_coef        0.0073(11) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    -0.009(13) 
_chemical_absolute_configuration  ad 
_refine_ls_number_reflns          2946 
_refine_ls_number_parameters      193 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0577 
_refine_ls_R_factor_gt            0.0384 
_refine_ls_wR_factor_ref          0.0995 
_refine_ls_wR_factor_gt           0.0900 
_refine_ls_goodness_of_fit_ref    1.024 
_refine_ls_restrained_S_all       1.024 
_refine_ls_shift/su_max           0.000 
_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 1.01406(7) -0.00697(5) 0.12295(2) 0.1205(3) Uani 1 1 d . . . 
N1 N 0.8606(3) 0.2293(3) 0.65575(16) 0.0570(7) Uani 1 1 d . . . 
O1 O 1.0380(3) 0.1377(3) 0.73222(15) 0.0828(8) Uani 1 1 d . . . 
O2 O 0.7150(3) 0.2925(3) 0.55163(18) 0.0782(8) Uani 1 1 d . . . 
O3 O 0.7153(3) -0.2602(3) 0.47386(17) 0.0802(8) Uani 1 1 d . . . 
C1 C 0.9771(4) 0.1472(3) 0.6681(2) 0.0576(8) Uani 1 1 d . . . 
C2 C 0.8149(3) 0.2281(3) 0.5761(2) 0.0553(8) Uani 1 1 d . . . 
C3 C 0.9104(3) 0.1368(3) 0.52630(18) 0.0508(7) Uani 1 1 d . . . 
H3 H 0.9624 0.1921 0.4862 0.061 Uiso 1 1 calc R . . 
C4 C 1.0103(3) 0.0741(3) 0.58912(18) 0.0521(7) Uani 1 1 d . . . 
H4 H 1.1088 0.0860 0.5733 0.063 Uiso 1 1 calc R . . 
C5 C 0.9681(3) -0.0770(3) 0.59086(18) 0.0497(7) Uani 1 1 d . . . 
H5 H 1.0061 -0.1416 0.6268 0.060 Uiso 1 1 calc R . . 
C6 C 0.8714(3) -0.1078(3) 0.53587(16) 0.0444(7) Uani 1 1 d . . . 
C7 C 0.8313(3) 0.0154(3) 0.48353(17) 0.0489(7) Uani 1 1 d . . . 
H7 H 0.7300 0.0311 0.4879 0.059 Uiso 1 1 calc R . . 
C8 C 0.8099(3) -0.2460(4) 0.5229(2) 0.0548(8) Uani 1 1 d . . . 
C9 C 0.8682(4) -0.3674(4) 0.5688(2) 0.0677(10) Uani 1 1 d . . . 
H9A H 0.8232 -0.4511 0.5505 0.102 Uiso 1 1 calc R . . 
H9B H 0.8514 -0.3552 0.6261 0.102 Uiso 1 1 calc R . . 
H9C H 0.9673 -0.3740 0.5591 0.102 Uiso 1 1 calc R . . 
C10 C 0.8704(3) 0.0004(3) 0.39498(17) 0.0523(7) Uani 1 1 d . . . 
C11 C 0.9887(4) -0.0719(4) 0.37123(18) 0.0606(8) Uani 1 1 d . . . 
H11 H 1.0415 -0.1186 0.4103 0.073 Uiso 1 1 calc R . . 
C12 C 1.0300(4) -0.0760(4) 0.28996(19) 0.0681(9) Uani 1 1 d . . . 
H12 H 1.1105 -0.1241 0.2748 0.082 Uiso 1 1 calc R . . 
C13 C 0.9525(5) -0.0095(4) 0.23324(19) 0.0728(11) Uani 1 1 d . . . 
C14 C 0.8341(6) 0.0620(5) 0.2542(2) 0.0893(14) Uani 1 1 d . . . 
H14 H 0.7818 0.1074 0.2144 0.107 Uiso 1 1 calc R . . 
C15 C 0.7928(4) 0.0662(4) 0.3347(2) 0.0752(11) Uani 1 1 d . . . 
H15 H 0.7115 0.1140 0.3488 0.090 Uiso 1 1 calc R . . 
C16 C 0.7901(5) 0.3067(4) 0.7207(3) 0.0799(11) Uani 1 1 d . . . 
H16A H 0.8383 0.3929 0.7298 0.120 Uiso 1 1 calc R . . 
H16B H 0.7909 0.2528 0.7701 0.120 Uiso 1 1 calc R . . 
H16C H 0.6949 0.3251 0.7050 0.120 Uiso 1 1 calc R . . 
  
  
_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 C13 1.899(3) . ? 
N1 C2 1.376(4) . ? 
N1 C1 1.377(4) . ? 
N1 C16 1.463(4) . ? 
O1 C1 1.203(4) . ? 
O2 C2 1.204(4) . ? 
O3 C8 1.215(4) . ? 
C1 C4 1.507(4) . ? 
C2 C3 1.505(5) . ? 
C3 C4 1.526(4) . ? 
C3 C7 1.557(4) . ? 
C3 H3 0.9800 . ? 
C4 C5 1.509(5) . ? 
C4 H4 0.9800 . ? 
C5 C6 1.322(4) . ? 
C5 H5 0.9300 . ? 
C6 C8 1.469(5) . ? 
C6 C7 1.513(4) . ? 
C7 C10 1.504(4) . ? 
C7 H7 0.9800 . ? 
C8 C9 1.496(5) . ? 
C9 H9A 0.9600 . ? 
C9 H9B 0.9600 . ? 
C9 H9C 0.9600 . ? 
C10 C11 1.380(4) . ? 
C10 C15 1.387(4) . ? 
C11 C12 1.389(4) . ? 
C11 H11 0.9300 . ? 
C12 C13 1.349(5) . ? 
C12 H12 0.9300 . ? 
C13 C14 1.365(6) . ? 
C14 C15 1.376(6) . ? 
C14 H14 0.9300 . ? 
C15 H15 0.9300 . ? 
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 
C2 N1 C1 113.0(3) . . ? 
C2 N1 C16 123.3(3) . . ? 
C1 N1 C16 123.7(3) . . ? 
O1 C1 N1 124.1(3) . . ? 
O1 C1 C4 127.7(3) . . ? 
N1 C1 C4 108.1(3) . . ? 
O2 C2 N1 124.1(3) . . ? 
O2 C2 C3 126.8(3) . . ? 
N1 C2 C3 109.1(3) . . ? 
C2 C3 C4 104.1(3) . . ? 
C2 C3 C7 112.9(2) . . ? 
C4 C3 C7 108.0(2) . . ? 
C2 C3 H3 110.6 . . ? 
C4 C3 H3 110.6 . . ? 
C7 C3 H3 110.6 . . ? 
C1 C4 C5 112.2(3) . . ? 
C1 C4 C3 105.2(3) . . ? 
C5 C4 C3 103.1(3) . . ? 
C1 C4 H4 111.9 . . ? 
C5 C4 H4 111.9 . . ? 
C3 C4 H4 111.9 . . ? 
C6 C5 C4 112.9(3) . . ? 
C6 C5 H5 123.5 . . ? 
C4 C5 H5 123.5 . . ? 
C5 C6 C8 125.4(3) . . ? 
C5 C6 C7 112.7(3) . . ? 
C8 C6 C7 121.9(2) . . ? 
C10 C7 C6 114.1(3) . . ? 
C10 C7 C3 112.7(2) . . ? 
C6 C7 C3 102.2(2) . . ? 
C10 C7 H7 109.2 . . ? 
C6 C7 H7 109.2 . . ? 
C3 C7 H7 109.2 . . ? 
O3 C8 C6 119.5(3) . . ? 
O3 C8 C9 121.3(3) . . ? 
C6 C8 C9 119.2(3) . . ? 
C8 C9 H9A 109.5 . . ? 
C8 C9 H9B 109.5 . . ? 
H9A C9 H9B 109.5 . . ? 
C8 C9 H9C 109.5 . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 109.5 . . ? 
C11 C10 C15 117.7(3) . . ? 
C11 C10 C7 121.5(2) . . ? 
C15 C10 C7 120.7(3) . . ? 
C10 C11 C12 121.1(3) . . ? 
C10 C11 H11 119.5 . . ? 
C12 C11 H11 119.5 . . ? 
C13 C12 C11 119.4(4) . . ? 
C13 C12 H12 120.3 . . ? 
C11 C12 H12 120.3 . . ? 
C12 C13 C14 121.3(3) . . ? 
C12 C13 Br1 119.5(3) . . ? 
C14 C13 Br1 119.2(3) . . ? 
C13 C14 C15 119.5(3) . . ? 
C13 C14 H14 120.3 . . ? 
C15 C14 H14 120.3 . . ? 
C14 C15 C10 121.1(4) . . ? 
C14 C15 H15 119.5 . . ? 
C10 C15 H15 119.5 . . ? 
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 . . ? 
  
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 
C2 N1 C1 O1 176.6(3) . . . . ? 
C16 N1 C1 O1 -5.0(5) . . . . ? 
C2 N1 C1 C4 -3.9(4) . . . . ? 
C16 N1 C1 C4 174.5(3) . . . . ? 
C1 N1 C2 O2 -179.9(3) . . . . ? 
C16 N1 C2 O2 1.7(5) . . . . ? 
C1 N1 C2 C3 -0.8(4) . . . . ? 
C16 N1 C2 C3 -179.2(3) . . . . ? 
O2 C2 C3 C4 -175.9(3) . . . . ? 
N1 C2 C3 C4 5.0(3) . . . . ? 
O2 C2 C3 C7 -59.1(4) . . . . ? 
N1 C2 C3 C7 121.8(3) . . . . ? 
O1 C1 C4 C5 74.8(5) . . . . ? 
N1 C1 C4 C5 -104.7(3) . . . . ? 
O1 C1 C4 C3 -173.8(3) . . . . ? 
N1 C1 C4 C3 6.8(4) . . . . ? 
C2 C3 C4 C1 -6.9(3) . . . . ? 
C7 C3 C4 C1 -127.1(3) . . . . ? 
C2 C3 C4 C5 110.9(3) . . . . ? 
C7 C3 C4 C5 -9.4(3) . . . . ? 
C1 C4 C5 C6 117.7(3) . . . . ? 
C3 C4 C5 C6 4.9(3) . . . . ? 
C4 C5 C6 C8 179.9(3) . . . . ? 
C4 C5 C6 C7 1.8(4) . . . . ? 
C5 C6 C7 C10 114.4(3) . . . . ? 
C8 C6 C7 C10 -63.8(4) . . . . ? 
C5 C6 C7 C3 -7.6(3) . . . . ? 
C8 C6 C7 C3 174.3(3) . . . . ? 
C2 C3 C7 C10 132.8(3) . . . . ? 
C4 C3 C7 C10 -112.7(3) . . . . ? 
C2 C3 C7 C6 -104.3(3) . . . . ? 
C4 C3 C7 C6 10.2(3) . . . . ? 
C5 C6 C8 O3 175.5(3) . . . . ? 
C7 C6 C8 O3 -6.6(4) . . . . ? 
C5 C6 C8 C9 -6.4(4) . . . . ? 
C7 C6 C8 C9 171.5(3) . . . . ? 
C6 C7 C10 C11 -32.7(4) . . . . ? 
C3 C7 C10 C11 83.3(4) . . . . ? 
C6 C7 C10 C15 151.2(3) . . . . ? 
C3 C7 C10 C15 -92.8(4) . . . . ? 
C15 C10 C11 C12 1.4(5) . . . . ? 
C7 C10 C11 C12 -174.9(3) . . . . ? 
C10 C11 C12 C13 -0.7(5) . . . . ? 
C11 C12 C13 C14 0.1(6) . . . . ? 
C11 C12 C13 Br1 176.8(3) . . . . ? 
C12 C13 C14 C15 -0.1(6) . . . . ? 
Br1 C13 C14 C15 -176.8(3) . . . . ? 
C13 C14 C15 C10 0.8(6) . . . . ? 
C11 C10 C15 C14 -1.4(5) . . . . ? 
C7 C10 C15 C14 174.9(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 
C4 H4 O2  0.98 2.57 3.281(4) 129.9 4_556 
C9 H9B O1  0.96 2.55 3.380(4) 145.0 3_746 
  
_diffrn_measured_fraction_theta_max    1.000 
_diffrn_reflns_theta_full              26.00 
_diffrn_measured_fraction_theta_full   1.000 
_refine_diff_density_max    0.262 
_refine_diff_density_min   -0.402 
_refine_diff_density_rms    0.043 
