 
data_tr1
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C14 H11 Br N2'
_chemical_formula_sum
 'C14 H11 Br N2'
_chemical_formula_weight          287.16
 
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'
 
_symmetry_cell_setting            'Monoclinic'
_symmetry_space_group_name_H-M    'P2(1)/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                    3.9980(8)
_cell_length_b                    10.759(2)
_cell_length_c                    26.867(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.18(3)
_cell_angle_gamma                 90.00
_cell_volume                      1155.7(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     300(2)
_cell_measurement_reflns_used     2010
_cell_measurement_theta_min       2.43
_cell_measurement_theta_max       26.83
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.25
_exptl_crystal_size_mid           0.24
_exptl_crystal_size_min           0.22
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.650
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              576
_exptl_absorpt_coefficient_mu     3.533
_exptl_absorpt_correction_type    'none'
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       300(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   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             12707
_diffrn_reflns_av_R_equivalents   0.2066
_diffrn_reflns_av_sigmaI/netI     0.1122
_diffrn_reflns_limit_h_min        -4
_diffrn_reflns_limit_h_max        4
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -31
_diffrn_reflns_limit_l_max        31
_diffrn_reflns_theta_min          2.43
_diffrn_reflns_theta_max          25.00
_reflns_number_total              2014
_reflns_number_gt                 1158
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_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 > 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)+(0.0377P)²+1.1852P] where P=(Fo²+2Fc²)/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          2014
_refine_ls_number_parameters      155
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1371
_refine_ls_R_factor_gt            0.0646
_refine_ls_wR_factor_ref          0.1168
_refine_ls_wR_factor_gt           0.0993
_refine_ls_goodness_of_fit_ref    1.016
_refine_ls_restrained_S_all       1.016
_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 0.1591(2) 0.63594(7) 0.47121(2) 0.0565(3) Uani 1 1 d . . .
C11 C -0.1456(17) 0.8708(6) 0.4590(2) 0.0467(18) Uani 1 1 d . . .
H11 H -0.1975 0.8636 0.4926 0.056 Uiso 1 1 calc R . .
C10 C 0.0262(16) 0.7786(6) 0.4347(2) 0.0383(17) Uani 1 1 d . . .
C6 C 0.0660(15) 1.0041(5) 0.2757(2) 0.0331(16) Uani 1 1 d . . .
H6 H -0.0314 1.0797 0.2841 0.040 Uiso 1 1 calc R . .
N1 N 0.2622(13) 0.8091(4) 0.28141(17) 0.0329(13) Uani 1 1 d . . .
C9 C 0.1111(15) 0.7887(5) 0.3854(2) 0.0326(16) Uani 1 1 d . . .
H9 H 0.2326 0.7257 0.3702 0.039 Uiso 1 1 calc R . .
C8 C 0.0164(15) 0.8926(5) 0.3583(2) 0.0298(15) Uani 1 1 d . . .
C7 C 0.1080(15) 0.9038(5) 0.3058(2) 0.0301(15) Uani 1 1 d . . .
C1 C 0.3133(15) 0.8509(5) 0.2360(2) 0.0304(14) Uani 1 1 d . . .
C3 C 0.4866(15) 0.8590(6) 0.1506(2) 0.0352(15) Uani 1 1 d . . .
N2 N 0.1953(13) 0.9716(4) 0.23072(17) 0.0325(13) Uani 1 1 d . . .
C2 C 0.4622(15) 0.7973(6) 0.1940(2) 0.0333(15) Uani 1 1 d . . .
H2 H 0.5465 0.7169 0.1962 0.040 Uiso 1 1 calc R . .
C5 C 0.2256(16) 1.0370(6) 0.1876(2) 0.0383(17) Uani 1 1 d . . .
H5 H 0.1504 1.1187 0.1857 0.046 Uiso 1 1 calc R . .
C4 C 0.3635(17) 0.9831(6) 0.1481(2) 0.0432(18) Uani 1 1 d . . .
H4 H 0.3799 1.0271 0.1184 0.052 Uiso 1 1 calc R . .
C12 C -0.2381(18) 0.9738(6) 0.4322(3) 0.052(2) Uani 1 1 d . . .
H12 H -0.3551 1.0374 0.4478 0.062 Uiso 1 1 calc R . .
C13 C -0.1605(16) 0.9842(6) 0.3827(2) 0.0425(18) Uani 1 1 d . . .
H13 H -0.2285 1.0544 0.3653 0.051 Uiso 1 1 calc R . .
C14 C 0.6388(17) 0.8025(6) 0.1053(2) 0.0483(19) Uani 1 1 d . . .
H14A H 0.7526 0.7272 0.1143 0.072 Uiso 1 1 calc R . .
H14B H 0.7956 0.8598 0.0910 0.072 Uiso 1 1 calc R . .
H14C H 0.4663 0.7842 0.0815 0.072 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 0.0682(6) 0.0585(5) 0.0428(4) 0.0133(4) 0.0043(4) 0.0024(5)
C11 0.046(5) 0.056(5) 0.038(4) -0.007(4) 0.009(3) -0.012(4)
C10 0.036(4) 0.040(4) 0.039(4) -0.001(3) -0.009(3) -0.011(3)
C6 0.040(4) 0.023(3) 0.036(4) -0.008(3) -0.002(3) 0.002(3)
N1 0.041(4) 0.026(3) 0.032(3) 0.005(2) 0.005(3) 0.002(3)
C9 0.041(4) 0.027(3) 0.031(3) -0.007(3) 0.002(3) -0.005(3)
C8 0.030(4) 0.026(4) 0.033(3) -0.008(3) -0.003(3) -0.007(3)
C7 0.023(4) 0.030(4) 0.037(3) -0.002(3) -0.001(3) -0.003(3)
C1 0.032(4) 0.018(3) 0.041(4) 0.004(3) -0.009(3) 0.002(3)
C3 0.025(4) 0.037(4) 0.043(4) -0.006(3) -0.003(3) -0.005(3)
N2 0.039(4) 0.023(3) 0.035(3) 0.003(2) -0.006(3) -0.006(3)
C2 0.025(4) 0.029(3) 0.046(4) -0.001(3) -0.004(3) 0.000(3)
C5 0.044(5) 0.026(4) 0.044(4) 0.013(3) -0.002(4) -0.004(3)
C4 0.050(5) 0.041(4) 0.038(4) 0.014(3) -0.001(4) -0.008(4)
C12 0.057(6) 0.045(5) 0.054(5) -0.009(4) 0.010(4) 0.004(4)
C13 0.040(5) 0.034(4) 0.053(4) -0.003(3) 0.004(4) -0.007(3)
C14 0.049(5) 0.053(4) 0.043(4) 0.002(3) -0.001(4) -0.001(4)
 
_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 C10 1.897(6) . ?
C11 C12 1.372(9) . ?
C11 C10 1.373(8) . ?
C10 C9 1.372(8) . ?
C6 C7 1.359(7) . ?
C6 N2 1.362(7) . ?
N1 C1 1.316(7) . ?
N1 C7 1.360(7) . ?
C9 C8 1.386(7) . ?
C8 C13 1.380(7) . ?
C8 C7 1.464(7) . ?
C1 N2 1.389(7) . ?
C1 C2 1.401(8) . ?
C3 C2 1.347(8) . ?
C3 C4 1.425(8) . ?
C3 C14 1.491(8) . ?
N2 C5 1.362(7) . ?
C5 C4 1.329(8) . ?
C12 C13 1.370(8) . ?
 
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
C12 C11 C10 117.9(6) . . ?
C9 C10 C11 121.9(6) . . ?
C9 C10 Br1 119.6(5) . . ?
C11 C10 Br1 118.5(5) . . ?
C7 C6 N2 106.1(5) . . ?
C1 N1 C7 105.2(5) . . ?
C10 C9 C8 120.2(6) . . ?
C13 C8 C9 117.7(5) . . ?
C13 C8 C7 122.0(5) . . ?
C9 C8 C7 120.3(5) . . ?
C6 C7 N1 111.3(5) . . ?
C6 C7 C8 127.4(5) . . ?
N1 C7 C8 121.2(5) . . ?
N1 C1 N2 111.1(5) . . ?
N1 C1 C2 132.3(5) . . ?
N2 C1 C2 116.6(5) . . ?
C2 C3 C4 118.4(6) . . ?
C2 C3 C14 122.5(6) . . ?
C4 C3 C14 119.1(6) . . ?
C6 N2 C5 131.1(5) . . ?
C6 N2 C1 106.2(5) . . ?
C5 N2 C1 122.6(5) . . ?
C3 C2 C1 121.8(6) . . ?
C4 C5 N2 119.4(6) . . ?
C5 C4 C3 121.1(6) . . ?
C13 C12 C11 120.9(6) . . ?
C12 C13 C8 121.4(6) . . ?
 
_diffrn_measured_fraction_theta_max    0.993
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.993
_refine_diff_density_max    0.378
_refine_diff_density_min   -0.517
_refine_diff_density_rms    0.090
