data_DU_V44BU_CU

_publ_requested_journal           '?'
_audit_creation_method            SHELXL-97
_chemical_formula_moiety          'C13 H12 Br2 N2 O3'
_chemical_formula_sum             'C13 H12 Br2 N2 O3'
_chemical_formula_weight          404.07
_chemical_melting_point           ?
_chemical_name_common             ?
_chemical_name_systematic         '?'
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'
 'Br' 'Br' -0.6763 1.2805
 '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'
 'O' 'O' 0.0492 0.0322 '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 1 21/c 1'
_symmetry_space_group_name_Hall   '-P 2ybc'
loop_
  _space_group_symop_id
  _space_group_symop_operation_xyz
 1 'x, y, z'
 2 '-x, y+1/2, -z+1/2'
 3 '-x, -y, -z'
 4 'x, -y-1/2, z-1/2'

_cell_angle_alpha                 90.00
_cell_angle_beta                  93.428(4)
_cell_angle_gamma                 90.00
_cell_formula_units_Z             4
_cell_length_a                    15.0119(6)
_cell_length_b                    3.99067(18)
_cell_length_c                    22.8802(9)
_cell_measurement_reflns_used     3157
_cell_measurement_temperature     150
_cell_measurement_theta_max       62.3394
_cell_measurement_theta_min       3.4266
_cell_volume                      1368.24(10)
_exptl_absorpt_coefficient_mu     7.611
_exptl_absorpt_correction_T_max   1.0
_exptl_absorpt_correction_T_min   0.63508
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details    
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_F_000              792
_exptl_crystal_colour             dark orange
_exptl_crystal_colour_modifier    dark
_exptl_crystal_colour_primary     orange
_exptl_crystal_density_diffrn     1.962
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_description        needle
_exptl_crystal_size_max           0.1
_exptl_crystal_size_mid           0.02
_exptl_crystal_size_min           0.02
_exptl_special_details            '?'
_diffrn_ambient_temperature       150
_diffrn_detector_area_resol_mean  16.2705
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details       
;
#__ type_ start__ end____ width___ exp.time_
1 omega -106.00  -60.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-      -32.9646  179.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
2 omega    6.00   95.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       32.9646   77.0000  150.0000 89

#__ type_ start__ end____ width___ exp.time_
3 omega  -37.00   60.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       32.9646  -77.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
4 omega   67.00  162.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000   45.0000  -60.0000 95

#__ type_ start__ end____ width___ exp.time_
5 omega   28.00   75.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  -45.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
6 omega   45.00   72.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  -45.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
7 omega   84.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  -77.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
8 omega  117.00  162.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000   45.0000 -120.0000 45

#__ type_ start__ end____ width___ exp.time_
9 omega  127.00  153.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  111.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
10 omega   24.00   82.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  -69.0000   67.0000 58

#__ type_ start__ end____ width___ exp.time_
11 omega  125.00  158.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000   45.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
12 omega  132.00  158.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
13 omega   37.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  -45.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
14 omega   98.00  163.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  111.0000  -90.0000 65

#__ type_ start__ end____ width___ exp.time_
15 omega   84.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000   45.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
16 omega   93.00  134.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  111.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
17 omega   54.00   81.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  -77.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
18 omega   34.00   60.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  179.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
19 omega   36.00   63.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
-       90.5000  -45.0000   60.0000 27
;
_diffrn_measurement_device_type   'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method        'ω scans'
_diffrn_orient_matrix_UB_11       0.0820922
_diffrn_orient_matrix_UB_12       0.2087486
_diffrn_orient_matrix_UB_13       0.0209734
_diffrn_orient_matrix_UB_21       0.05913
_diffrn_orient_matrix_UB_22       -0.2157706
_diffrn_orient_matrix_UB_23       -0.0379398
_diffrn_orient_matrix_UB_31       -0.018185
_diffrn_orient_matrix_UB_32       0.2428524
_diffrn_orient_matrix_UB_33       -0.0516682
_diffrn_radiation_monochromator   mirror
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_type            'Cu K\a'
_diffrn_radiation_wavelength      1.5418
_diffrn_reflns_av_R_equivalents   0.0437
_diffrn_reflns_av_sigmaI/netI     0.0347
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_h_min        -16
_diffrn_reflns_limit_k_max        4
_diffrn_reflns_limit_k_min        -4
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_limit_l_min        -26
_diffrn_reflns_number             4645
_diffrn_reflns_theta_full         62.43
_diffrn_reflns_theta_max          62.43
_diffrn_reflns_theta_min          3.87
_diffrn_standards_decay_%         ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_number          ?
_reflns_number_gt                 1899
_reflns_number_total              2161
_reflns_threshold_expression      >2sigma(I)
_computing_cell_refinement        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_collection        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction         
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_molecular_graphics     
;
OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material   
;
OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution     'A short history of SHELX (Sheldrick, 2007)'
_refine_diff_density_max          0.709
_refine_diff_density_min          -0.878
_refine_diff_density_rms          0.140
_refine_ls_R_factor_all           0.0374
_refine_ls_R_factor_gt            0.0317
_refine_ls_extinction_coef        ?
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.038
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      182
_refine_ls_number_reflns          2161
_refine_ls_number_restraints      0
_refine_ls_restrained_S_all       1.038
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_wR_factor_gt           0.0895
_refine_ls_wR_factor_ref          0.0921
_refine_ls_weighting_details      
;
calc w=1/[σ²(Fo²)+(0.0698P)²+0.0000P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme       calc
_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. 
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
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 0.33739(2) 0.89731(9) 0.060482(14) 0.02390(16) Uani 1 1 d . . .
 Br2 Br 0.43059(2) 1.06444(10) 0.196717(15) 0.02541(16) Uani 1 1 d . . .
 O3 O 0.11896(17) 1.5685(7) 0.23845(10) 0.0316(7) Uani 1 1 d . . .
 O2 O 0.29589(16) 1.4629(7) 0.26097(10) 0.0250(6) Uani 1 1 d . . .
 N2 N -0.10346(18) 1.5201(7) 0.12633(11) 0.0191(6) Uani 1 1 d . . .
 O1 O 0.15273(15) 1.1443(6) 0.04934(9) 0.0228(5) Uani 1 1 d . . .
 N1 N 0.03942(18) 1.4493(7) 0.12534(11) 0.0182(6) Uani 1 1 d . . .
 C9 C -0.0770(2) 1.6553(9) 0.07467(14) 0.0213(7) Uani 1 1 d . . .
 H9 H -0.1144 1.7596 0.0450 0.026 Uiso 1 1 calc R . .
 C4 C 0.3136(2) 1.1760(9) 0.17189(14) 0.0187(7) Uani 1 1 d . . .
 C2 C 0.1807(2) 1.2067(8) 0.09970(13) 0.0183(7) Uani 1 1 d . . .
 C12 C -0.3598(2) 1.4902(10) 0.11907(14) 0.0230(8) Uani 1 1 d . . .
 H12A H -0.3681 1.3412 0.1529 0.028 Uiso 1 1 calc R . .
 H12B H -0.3670 1.7243 0.1323 0.028 Uiso 1 1 calc R . .
 C7 C -0.0330(2) 1.3963(8) 0.15622(14) 0.0189(7) Uani 1 1 d . . .
 H7 H -0.0333 1.2883 0.1932 0.023 Uiso 1 1 calc R . .
 C8 C 0.0118(2) 1.6114(9) 0.07417(14) 0.0214(7) Uani 1 1 d . . .
 H8 H 0.0488 1.6796 0.0441 0.026 Uiso 1 1 calc R . .
 C1 C 0.1295(2) 1.3605(9) 0.14277(14) 0.0186(7) Uani 1 1 d . . .
 C6 C 0.1619(2) 1.4384(9) 0.19968(14) 0.0207(7) Uani 1 1 d . . .
 C10 C -0.1962(2) 1.5358(9) 0.14633(14) 0.0203(7) Uani 1 1 d . . .
 H10B H -0.2082 1.7655 0.1602 0.024 Uiso 1 1 calc R . .
 H10A H -0.2013 1.3811 0.1798 0.024 Uiso 1 1 calc R . .
 C3 C 0.2756(2) 1.1114(8) 0.11873(14) 0.0179(7) Uani 1 1 d . . .
 C5 C 0.2615(2) 1.3656(9) 0.21521(13) 0.0190(7) Uani 1 1 d . . .
 C11 C -0.2655(2) 1.4439(9) 0.09872(14) 0.0211(7) Uani 1 1 d . . .
 H11A H -0.2571 1.2074 0.0872 0.025 Uiso 1 1 calc R . .
 H11B H -0.2576 1.5861 0.0640 0.025 Uiso 1 1 calc R . .
 C13 C -0.4314(3) 1.4130(10) 0.07103(15) 0.0265(8) Uani 1 1 d . . .
 H13B H -0.4237 1.5606 0.0375 0.040 Uiso 1 1 calc R . .
 H13C H -0.4905 1.4496 0.0859 0.040 Uiso 1 1 calc R . .
 H13A H -0.4260 1.1789 0.0588 0.040 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 C3 1.874(3) . ?
 Br2 C4 1.868(3) . ?
 O3 C6 1.241(4) . ?
 O2 C5 1.204(4) . ?
 N2 C9 1.379(4) . ?
 N2 C7 1.320(4) . ?
 N2 C10 1.493(4) . ?
 O1 C2 1.228(4) . ?
 N1 C7 1.349(4) . ?
 N1 C8 1.379(5) . ?
 N1 C1 1.431(4) . ?
 C9 H9 0.9500 . ?
 C9 C8 1.345(5) . ?
 C4 C3 1.337(5) . ?
 C4 C5 1.503(5) . ?
 C2 C1 1.424(5) . ?
 C2 C3 1.514(5) . ?
 C12 H12A 0.9900 . ?
 C12 H12B 0.9900 . ?
 C12 C11 1.529(5) . ?
 C12 C13 1.521(5) . ?
 C7 H7 0.9500 . ?
 C8 H8 0.9500 . ?
 C1 C6 1.398(5) . ?
 C6 C5 1.544(5) . ?
 C10 H10B 0.9900 . ?
 C10 H10A 0.9900 . ?
 C10 C11 1.505(5) . ?
 C11 H11A 0.9900 . ?
 C11 H11B 0.9900 . ?
 C13 H13B 0.9800 . ?
 C13 H13C 0.9800 . ?
 C13 H13A 0.9800 . ?

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
 O3 C6 C1 126.3(3) . . ?
 O3 C6 C5 116.8(3) . . ?
 O2 C5 C4 121.6(3) . . ?
 O2 C5 C6 119.9(3) . . ?
 N2 C9 H9 126.5 . . ?
 N2 C7 N1 108.4(3) . . ?
 N2 C7 H7 125.8 . . ?
 N2 C10 H10B 109.1 . . ?
 N2 C10 H10A 109.1 . . ?
 N2 C10 C11 112.6(3) . . ?
 O1 C2 C1 124.7(3) . . ?
 O1 C2 C3 118.8(3) . . ?
 N1 C7 H7 125.8 . . ?
 N1 C8 H8 126.2 . . ?
 C9 N2 C10 124.6(3) . . ?
 C9 C8 N1 107.5(3) . . ?
 C9 C8 H8 126.2 . . ?
 C4 C3 Br1 122.2(3) . . ?
 C4 C3 C2 123.8(3) . . ?
 C4 C5 C6 118.5(3) . . ?
 C2 C1 N1 117.0(3) . . ?
 C2 C3 Br1 114.0(2) . . ?
 C12 C11 H11A 109.4 . . ?
 C12 C11 H11B 109.4 . . ?
 C12 C13 H13B 109.5 . . ?
 C12 C13 H13C 109.5 . . ?
 C12 C13 H13A 109.5 . . ?
 H12A C12 H12B 107.8 . . ?
 C7 N2 C9 109.1(3) . . ?
 C7 N2 C10 126.1(3) . . ?
 C7 N1 C8 107.9(3) . . ?
 C7 N1 C1 126.4(3) . . ?
 C8 N1 C1 125.7(3) . . ?
 C8 C9 N2 107.0(3) . . ?
 C8 C9 H9 126.5 . . ?
 C1 C2 C3 116.5(3) . . ?
 C1 C6 C5 116.8(3) . . ?
 C6 C1 N1 118.4(3) . . ?
 C6 C1 C2 124.6(3) . . ?
 C10 C11 C12 111.2(3) . . ?
 C10 C11 H11A 109.4 . . ?
 C10 C11 H11B 109.4 . . ?
 H10B C10 H10A 107.8 . . ?
 C3 C4 Br2 124.9(3) . . ?
 C3 C4 C5 119.2(3) . . ?
 C5 C4 Br2 115.9(2) . . ?
 C11 C12 H12A 109.1 . . ?
 C11 C12 H12B 109.1 . . ?
 C11 C10 H10B 109.1 . . ?
 C11 C10 H10A 109.1 . . ?
 H11A C11 H11B 108.0 . . ?
 C13 C12 H12A 109.1 . . ?
 C13 C12 H12B 109.1 . . ?
 C13 C12 C11 112.5(3) . . ?
 H13B C13 H13C 109.5 . . ?
 H13B C13 H13A 109.5 . . ?
 H13C C13 H13A 109.5 . . ?