 
data_solution
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C11 H11 Br2 N'
_chemical_formula_sum
 'C11 H11 Br2 N'
_chemical_formula_weight          317.03
 
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'
 'Br'  'Br'  -0.2901   2.4595
 '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'
 
_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    P2(1)/c
_symmetry_space_group_name_hall   '-P 2ybc'
 
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                    12.0452(3)
_cell_length_b                    11.8133(3)
_cell_length_c                    8.0824(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  96.646(2)
_cell_angle_gamma                 90.00
_cell_volume                      1142.35(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     11218
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.40
_exptl_crystal_size_mid           0.33
_exptl_crystal_size_min           0.14
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.843
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              616
_exptl_absorpt_coefficient_mu     7.057
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.3813
_exptl_absorpt_correction_T_max   0.7456
_exptl_absorpt_process_details    'OSRTAV (R.H.Blessing, 1995, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             15855
_diffrn_reflns_av_R_equivalents   0.0495
_diffrn_reflns_av_sigmaI/netI     0.0334
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          3.36
_diffrn_reflns_theta_max          27.48
_reflns_number_total              2623
_reflns_number_gt                 2336
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     'PLATON (Watkin, Pearce 1995)'
_computing_publication_material   SHELXL-97
 
_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 > 2σ(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)+(0.0163P)²+10.1011P] 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      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2623
_refine_ls_number_parameters      130
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0479
_refine_ls_R_factor_gt            0.0417
_refine_ls_wR_factor_ref          0.1180
_refine_ls_wR_factor_gt           0.1160
_refine_ls_goodness_of_fit_ref    1.305
_refine_ls_restrained_S_all       1.305
_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 0.21013(5) -0.19273(5) 0.20595(7) 0.01843(16) Uani 1 1 d . . .
Br2 Br 0.52665(5) 0.16457(5) 0.31153(8) 0.02507(18) Uani 1 1 d . . .
N1 N 0.1281(4) -0.0792(4) 0.5394(6) 0.0138(9) Uani 1 1 d . . .
C8 C 0.1151(5) -0.0204(4) 0.6708(7) 0.0153(11) Uani 1 1 d . . .
C1 C 0.2197(4) -0.0296(4) 0.4695(7) 0.0141(10) Uani 1 1 d . . .
C4 C 0.4006(5) 0.0862(5) 0.3771(7) 0.0173(11) Uani 1 1 d . . .
C7 C 0.1953(5) 0.0789(4) 0.7048(7) 0.0166(11) Uani 1 1 d . . .
C11 C 0.0280(5) -0.0486(5) 0.7811(7) 0.0213(12) Uani 1 1 d . . .
H11A H -0.0240 -0.1043 0.7257 0.032 Uiso 1 1 calc R . .
H11B H -0.0130 0.0202 0.8042 0.032 Uiso 1 1 calc R . .
H11C H 0.0638 -0.0803 0.8860 0.032 Uiso 1 1 calc R . .
C9 C 0.1333(5) 0.1918(5) 0.6991(8) 0.0210(12) Uani 1 1 d . . .
H9A H 0.0860 0.1988 0.5926 0.031 Uiso 1 1 calc R . .
H9B H 0.1876 0.2539 0.7105 0.031 Uiso 1 1 calc R . .
H9C H 0.0867 0.1951 0.7906 0.031 Uiso 1 1 calc R . .
C6 C 0.2630(4) 0.0640(4) 0.5605(7) 0.0142(10) Uani 1 1 d . . .
C10 C 0.2676(5) 0.0623(5) 0.8740(8) 0.0248(13) Uani 1 1 d . . .
H10A H 0.2205 0.0701 0.9645 0.037 Uiso 1 1 calc R . .
H10B H 0.3267 0.1196 0.8868 0.037 Uiso 1 1 calc R . .
H10C H 0.3012 -0.0133 0.8781 0.037 Uiso 1 1 calc R . .
C5 C 0.3538(5) 0.1241(5) 0.5154(7) 0.0188(11) Uani 1 1 d . . .
H5 H 0.3826 0.1883 0.5768 0.023 Uiso 1 1 calc R . .
C3 C 0.3601(4) -0.0072(5) 0.2840(7) 0.0166(11) Uani 1 1 d . . .
H3 H 0.3946 -0.0308 0.1898 0.020 Uiso 1 1 calc R . .
C2 C 0.2677(5) -0.0657(5) 0.3314(7) 0.0152(11) Uani 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
Br1 0.0185(3) 0.0175(3) 0.0194(3) -0.0061(2) 0.0027(2) 0.0006(2)
Br2 0.0138(3) 0.0246(3) 0.0365(4) 0.0127(3) 0.0017(2) -0.0016(2)
N1 0.014(2) 0.014(2) 0.014(2) 0.0013(17) 0.0007(18) 0.0019(17)
C8 0.018(3) 0.013(2) 0.015(3) 0.006(2) 0.001(2) 0.003(2)
C1 0.012(2) 0.014(2) 0.015(2) 0.002(2) -0.002(2) 0.0002(19)
C4 0.011(2) 0.017(3) 0.023(3) 0.008(2) -0.001(2) 0.002(2)
C7 0.023(3) 0.013(2) 0.013(2) -0.002(2) -0.003(2) 0.001(2)
C11 0.024(3) 0.023(3) 0.018(3) 0.003(2) 0.006(2) 0.006(2)
C9 0.026(3) 0.015(3) 0.022(3) -0.002(2) 0.004(2) 0.004(2)
C6 0.014(3) 0.014(2) 0.013(2) 0.005(2) -0.004(2) -0.0004(19)
C10 0.029(3) 0.026(3) 0.019(3) 0.000(2) -0.003(3) 0.003(3)
C5 0.014(3) 0.016(3) 0.024(3) 0.001(2) -0.007(2) -0.001(2)
C3 0.011(2) 0.023(3) 0.015(3) 0.004(2) -0.002(2) 0.002(2)
C2 0.015(3) 0.015(2) 0.014(2) 0.002(2) -0.003(2) 0.000(2)
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.896(5) . ?
Br2 C4 1.905(5) . ?
N1 C8 1.294(7) . ?
N1 C1 1.422(7) . ?
C8 C11 1.491(8) . ?
C8 C7 1.524(8) . ?
C1 C2 1.383(8) . ?
C1 C6 1.396(7) . ?
C4 C5 1.383(8) . ?
C4 C3 1.391(8) . ?
C7 C6 1.509(8) . ?
C7 C9 1.527(7) . ?
C7 C10 1.546(8) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C6 C5 1.387(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C5 H5 0.9500 . ?
C3 C2 1.402(8) . ?
C3 H3 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
C8 N1 C1 106.1(5) . . ?
N1 C8 C11 122.1(5) . . ?
N1 C8 C7 115.3(5) . . ?
C11 C8 C7 122.6(5) . . ?
C2 C1 C6 120.3(5) . . ?
C2 C1 N1 127.5(5) . . ?
C6 C1 N1 112.2(5) . . ?
C5 C4 C3 122.9(5) . . ?
C5 C4 Br2 118.7(4) . . ?
C3 C4 Br2 118.4(4) . . ?
C6 C7 C9 112.6(5) . . ?
C6 C7 C8 99.2(4) . . ?
C9 C7 C8 111.7(5) . . ?
C6 C7 C10 111.7(5) . . ?
C9 C7 C10 111.1(5) . . ?
C8 C7 C10 110.0(5) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C6 C1 121.7(5) . . ?
C5 C6 C7 131.1(5) . . ?
C1 C6 C7 107.3(5) . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C5 C6 117.0(5) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 H5 121.5 . . ?
C4 C3 C2 118.9(5) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C1 C2 C3 119.2(5) . . ?
C1 C2 Br1 121.0(4) . . ?
C3 C2 Br1 119.8(4) . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    1.414
_refine_diff_density_min   -0.785
_refine_diff_density_rms    0.165
