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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_70320b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 Br N'
_chemical_formula_weight         310.19

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'
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                   10.441(2)
_cell_length_b                   13.358(3)
_cell_length_c                   11.148(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.108(4)
_cell_angle_gamma                90.00
_cell_volume                     1396.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1896
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      22.15

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    2.928
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5651
_exptl_absorpt_correction_T_max  0.7201
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(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            7911
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         26.43
_reflns_number_total             2850
_reflns_number_gt                1652
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0556P)²+0.1512P] 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         2850
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_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 0.97089(5) 1.24218(3) 0.24937(4) 0.0615(2) Uani 1 1 d . . .
N1 N 0.6058(4) 0.7265(2) 0.5152(3) 0.0545(9) Uani 1 1 d . . .
C1 C 0.8252(4) 1.0603(3) 0.4617(4) 0.0497(10) Uani 1 1 d . . .
H1 H 0.8180 1.0650 0.5417 0.060 Uiso 1 1 calc R . .
C2 C 0.8808(4) 1.1399(3) 0.4214(4) 0.0502(10) Uani 1 1 d . . .
H2 H 0.9098 1.1977 0.4729 0.060 Uiso 1 1 calc R . .
C3 C 0.8927(4) 1.1324(2) 0.3037(3) 0.0432(9) Uani 1 1 d . . .
C4 C 0.8480(4) 1.0482(3) 0.2253(3) 0.0461(9) Uani 1 1 d . . .
H4 H 0.8550 1.0445 0.1451 0.055 Uiso 1 1 calc R . .
C5 C 0.7924(4) 0.9687(3) 0.2675(3) 0.0449(9) Uani 1 1 d . . .
H5 H 0.7629 0.9113 0.2152 0.054 Uiso 1 1 calc R . .
C6 C 0.7798(4) 0.9735(3) 0.3868(3) 0.0402(9) Uani 1 1 d . . .
C7 C 0.7201(4) 0.8881(3) 0.4314(3) 0.0423(9) Uani 1 1 d . . .
C8 C 0.6477(4) 0.9036(3) 0.5098(4) 0.0523(10) Uani 1 1 d . . .
H8 H 0.6354 0.9677 0.5355 0.063 Uiso 1 1 calc R . .
C9 C 0.5953(5) 0.8213(3) 0.5478(4) 0.0607(11) Uani 1 1 d . . .
H9 H 0.5484 0.8327 0.6007 0.073 Uiso 1 1 calc R . .
C10 C 0.6765(4) 0.7114(3) 0.4402(3) 0.0428(9) Uani 1 1 d . . .
C11 C 0.7321(4) 0.7904(3) 0.3971(3) 0.0429(9) Uani 1 1 d . . .
H11 H 0.7784 0.7773 0.3441 0.051 Uiso 1 1 calc R . .
C12 C 0.6895(4) 0.6063(3) 0.4058(3) 0.0440(9) Uani 1 1 d . . .
C13 C 0.5856(4) 0.5363(3) 0.3925(4) 0.0528(10) Uani 1 1 d . . .
H13 H 0.5075 0.5560 0.4060 0.063 Uiso 1 1 calc R . .
C14 C 0.5959(5) 0.4380(3) 0.3596(4) 0.0623(12) Uani 1 1 d . . .
H14 H 0.5256 0.3923 0.3520 0.075 Uiso 1 1 calc R . .
C15 C 0.7097(5) 0.4074(3) 0.3381(4) 0.0611(12) Uani 1 1 d . . .
H15 H 0.7157 0.3415 0.3141 0.073 Uiso 1 1 calc R . .
C16 C 0.8146(5) 0.4749(3) 0.3524(4) 0.0611(12) Uani 1 1 d . . .
H16 H 0.8926 0.4544 0.3392 0.073 Uiso 1 1 calc R . .
C17 C 0.8050(5) 0.5730(3) 0.3864(4) 0.0546(11) Uani 1 1 d . . .
H17 H 0.8773 0.6177 0.3964 0.066 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 0.0861(4) 0.0501(3) 0.0619(3) 0.0045(2) 0.0453(3) -0.0037(2)
N1 0.065(2) 0.057(2) 0.0523(19) 0.0039(16) 0.0365(19) -0.0019(18)
C1 0.067(3) 0.052(2) 0.036(2) -0.0015(18) 0.028(2) 0.000(2)
C2 0.067(3) 0.043(2) 0.044(2) -0.0069(18) 0.028(2) -0.004(2)
C3 0.052(2) 0.036(2) 0.042(2) 0.0071(16) 0.0218(19) 0.0059(18)
C4 0.054(3) 0.050(2) 0.037(2) 0.0025(17) 0.0224(19) 0.0069(19)
C5 0.055(3) 0.043(2) 0.036(2) -0.0075(17) 0.0196(19) -0.0018(19)
C6 0.041(2) 0.045(2) 0.0333(19) 0.0037(16) 0.0152(17) 0.0077(17)
C7 0.045(2) 0.047(2) 0.0341(19) 0.0023(16) 0.0167(18) 0.0000(18)
C8 0.061(3) 0.051(2) 0.054(2) 0.0018(19) 0.034(2) 0.006(2)
C9 0.070(3) 0.070(3) 0.059(3) 0.002(2) 0.043(2) 0.000(2)
C10 0.042(2) 0.048(2) 0.0371(19) 0.0056(17) 0.0160(18) 0.0016(18)
C11 0.049(2) 0.044(2) 0.0400(19) 0.0004(17) 0.0230(19) 0.0029(18)
C12 0.049(2) 0.045(2) 0.0371(19) 0.0074(17) 0.0184(18) -0.0021(19)
C13 0.048(3) 0.059(3) 0.052(2) -0.003(2) 0.022(2) -0.009(2)
C14 0.061(3) 0.053(3) 0.064(3) -0.002(2) 0.020(2) -0.013(2)
C15 0.072(3) 0.046(2) 0.060(3) -0.002(2) 0.024(3) 0.003(2)
C16 0.070(3) 0.056(3) 0.070(3) 0.005(2) 0.043(3) 0.004(2)
C17 0.054(3) 0.053(3) 0.065(3) 0.008(2) 0.034(2) -0.003(2)

_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 1.902(3) . ?
N1 C9 1.335(5) . ?
N1 C10 1.352(5) . ?
C1 C2 1.378(5) . ?
C1 C6 1.385(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(5) . ?
C4 C5 1.388(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.486(5) . ?
C7 C11 1.382(5) . ?
C7 C8 1.400(5) . ?
C8 C9 1.375(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.389(5) . ?
C10 C12 1.478(5) . ?
C11 H11 0.9300 . ?
C12 C17 1.388(5) . ?
C12 C13 1.390(5) . ?
C13 C14 1.379(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?

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
C9 N1 C10 116.3(3) . . ?
C2 C1 C6 122.0(3) . . ?
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 Br1 120.2(3) . . ?
C2 C3 Br1 118.7(3) . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 117.6(3) . . ?
C1 C6 C7 121.5(3) . . ?
C5 C6 C7 120.9(3) . . ?
C11 C7 C8 116.9(3) . . ?
C11 C7 C6 122.0(3) . . ?
C8 C7 C6 121.1(3) . . ?
C9 C8 C7 118.2(4) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
N1 C9 C8 125.6(4) . . ?
N1 C9 H9 117.2 . . ?
C8 C9 H9 117.2 . . ?
N1 C10 C11 121.8(3) . . ?
N1 C10 C12 116.1(3) . . ?
C11 C10 C12 122.1(3) . . ?
C7 C11 C10 121.3(3) . . ?
C7 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C17 C12 C13 117.3(4) . . ?
C17 C12 C10 122.0(3) . . ?
C13 C12 C10 120.7(4) . . ?
C14 C13 C12 121.3(4) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.4(4) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.4(4) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 121.3(4) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?

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
C6 C1 C2 C3 -0.6(6) . . . . ?
C1 C2 C3 C4 1.2(6) . . . . ?
C1 C2 C3 Br1 -179.5(3) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
Br1 C3 C4 C5 179.5(3) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C2 C1 C6 C5 0.1(6) . . . . ?
C2 C1 C6 C7 180.0(4) . . . . ?
C4 C5 C6 C1 -0.2(6) . . . . ?
C4 C5 C6 C7 180.0(3) . . . . ?
C1 C6 C7 C11 -151.0(4) . . . . ?
C5 C6 C7 C11 28.8(5) . . . . ?
C1 C6 C7 C8 29.5(6) . . . . ?
C5 C6 C7 C8 -150.7(4) . . . . ?
C11 C7 C8 C9 0.6(6) . . . . ?
C6 C7 C8 C9 -179.9(4) . . . . ?
C10 N1 C9 C8 1.1(6) . . . . ?
C7 C8 C9 N1 -0.7(7) . . . . ?
C9 N1 C10 C11 -1.3(5) . . . . ?
C9 N1 C10 C12 179.2(3) . . . . ?
C8 C7 C11 C10 -0.9(5) . . . . ?
C6 C7 C11 C10 179.6(3) . . . . ?
N1 C10 C11 C7 1.3(6) . . . . ?
C12 C10 C11 C7 -179.3(3) . . . . ?
N1 C10 C12 C17 -149.9(4) . . . . ?
C11 C10 C12 C17 30.6(5) . . . . ?
N1 C10 C12 C13 29.7(5) . . . . ?
C11 C10 C12 C13 -149.7(4) . . . . ?
C17 C12 C13 C14 -0.8(6) . . . . ?
C10 C12 C13 C14 179.6(3) . . . . ?
C12 C13 C14 C15 -0.6(6) . . . . ?
C13 C14 C15 C16 1.4(6) . . . . ?
C14 C15 C16 C17 -0.9(7) . . . . ?
C15 C16 C17 C12 -0.5(6) . . . . ?
C13 C12 C17 C16 1.3(6) . . . . ?
C10 C12 C17 C16 -179.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.43
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.068
_database_code_depnum_ccdc_archive 'CCDC 955651'
