# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H8 Br N2'
_chemical_formula_weight         272.12

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           ?
_symmetry_space_group_name_H-M   ?

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                   4.8956(2)
_cell_length_b                   18.5240(6)
_cell_length_c                   12.7557(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.433(2)
_cell_angle_gamma                90.00
_cell_volume                     1137.64(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             540
_exptl_absorpt_coefficient_mu    3.584
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7878
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         27.94
_reflns_number_total             2722
_reflns_number_gt                1327
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0648P)²+0.0000P] 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         2722
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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 0.37953(13) 0.58031(2) 0.10895(4) 0.1039(3) Uani 1 1 d . . .
N1 N 0.5587(6) 0.33635(17) 0.4200(2) 0.0567(8) Uani 1 1 d . . .
C5 C 0.6502(7) 0.39370(18) 0.2739(2) 0.0449(8) Uani 1 1 d . . .
C6 C 0.6128(7) 0.45013(19) 0.1986(3) 0.0535(9) Uani 1 1 d . . .
H6A H 0.7007 0.4493 0.1398 0.064 Uiso 1 1 calc R . .
C14 C 0.9578(6) 0.29043(19) 0.2127(2) 0.0486(8) Uani 1 1 d . . .
C1 C 0.4439(8) 0.50610(19) 0.2146(3) 0.0613(10) Uani 1 1 d . . .
C13 C 1.0653(7) 0.32759(19) 0.1348(3) 0.0556(9) Uani 1 1 d . . .
H13A H 1.0307 0.3767 0.1246 0.067 Uiso 1 1 calc R . .
N2 N 1.2859(6) 0.22234(19) 0.0808(2) 0.0626(8) Uani 1 1 d . . .
C7 C 0.7874(7) 0.32468(18) 0.2822(2) 0.0491(8) Uani 1 1 d . . .
C10 C 1.0216(9) 0.2178(2) 0.2208(3) 0.0725(11) Uani 1 1 d . . .
H10A H 0.9559 0.1899 0.2714 0.087 Uiso 1 1 calc R . .
C4 C 0.5081(7) 0.39829(19) 0.3606(3) 0.0484(8) Uani 1 1 d . . .
C12 C 1.2244(8) 0.2912(2) 0.0725(3) 0.0640(10) Uani 1 1 d . . .
H12A H 1.2926 0.3176 0.0208 0.077 Uiso 1 1 calc R . .
C3 C 0.3434(7) 0.4570(2) 0.3754(3) 0.0592(10) Uani 1 1 d . . .
H3A H 0.2564 0.4596 0.4343 0.071 Uiso 1 1 calc R . .
C11 C 1.1812(9) 0.1860(2) 0.1549(3) 0.0776(12) Uani 1 1 d . . .
H11A H 1.2177 0.1369 0.1623 0.093 Uiso 1 1 calc R . .
C2 C 0.3120(8) 0.5113(2) 0.3010(3) 0.0662(10) Uani 1 1 d . . .
H2A H 0.2025 0.5513 0.3088 0.079 Uiso 1 1 calc R . .
C8 C 0.7223(7) 0.2926(2) 0.3725(3) 0.0576(9) Uani 1 1 d . . .
H8A H 0.7827 0.2471 0.3974 0.069 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 0.1830(7) 0.0600(4) 0.0785(4) 0.0167(2) 0.0494(4) 0.0313(3)
N1 0.0654(19) 0.062(2) 0.0480(16) 0.0038(15) 0.0238(15) 0.0027(16)
C5 0.0490(19) 0.048(2) 0.0396(17) -0.0053(14) 0.0130(15) -0.0098(17)
C6 0.073(2) 0.046(2) 0.0460(18) -0.0013(16) 0.0236(17) -0.010(2)
C14 0.050(2) 0.057(2) 0.0415(18) -0.0022(15) 0.0157(16) -0.0040(17)
C1 0.086(3) 0.046(2) 0.054(2) 0.0053(16) 0.020(2) -0.003(2)
C13 0.064(2) 0.050(2) 0.059(2) 0.0001(17) 0.0273(19) -0.0059(19)
N2 0.065(2) 0.071(2) 0.0557(18) -0.0126(16) 0.0227(15) -0.0048(18)
C7 0.053(2) 0.052(2) 0.0452(18) 0.0019(15) 0.0159(16) -0.0065(18)
C10 0.098(3) 0.060(3) 0.072(3) 0.010(2) 0.050(2) 0.011(2)
C4 0.053(2) 0.052(2) 0.0434(17) -0.0019(16) 0.0173(16) -0.0041(18)
C12 0.075(3) 0.071(3) 0.054(2) -0.0066(19) 0.034(2) -0.014(2)
C3 0.070(3) 0.056(2) 0.058(2) -0.0095(19) 0.0302(19) -0.001(2)
C11 0.094(3) 0.066(3) 0.081(3) -0.001(2) 0.039(3) 0.004(2)
C2 0.083(3) 0.049(2) 0.070(3) -0.0054(19) 0.024(2) 0.008(2)
C8 0.066(2) 0.059(2) 0.052(2) 0.0072(17) 0.0230(18) 0.0068(19)

_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 C1 1.911(3) . ?
N1 C8 1.358(5) . ?
N1 C4 1.373(4) . ?
C5 C6 1.408(5) . ?
C5 C4 1.412(4) . ?
C5 C7 1.439(5) . ?
C6 C1 1.364(5) . ?
C14 C10 1.381(5) . ?
C14 C13 1.388(4) . ?
C14 C7 1.466(4) . ?
C1 C2 1.377(5) . ?
C13 C12 1.385(5) . ?
N2 C12 1.311(5) . ?
N2 C11 1.335(5) . ?
C7 C8 1.384(4) . ?
C10 C11 1.379(5) . ?
C4 C3 1.387(5) . ?
C3 C2 1.372(5) . ?

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 C4 108.3(3) . . ?
C6 C5 C4 117.9(3) . . ?
C6 C5 C7 135.3(3) . . ?
C4 C5 C7 106.6(3) . . ?
C1 C6 C5 118.0(3) . . ?
C10 C14 C13 115.2(3) . . ?
C10 C14 C7 121.5(3) . . ?
C13 C14 C7 123.3(3) . . ?
C6 C1 C2 123.9(3) . . ?
C6 C1 Br1 117.9(3) . . ?
C2 C1 Br1 118.2(3) . . ?
C12 C13 C14 119.7(3) . . ?
C12 N2 C11 115.8(3) . . ?
C8 C7 C5 105.5(3) . . ?
C8 C7 C14 124.0(3) . . ?
C5 C7 C14 130.5(3) . . ?
C11 C10 C14 121.1(4) . . ?
N1 C4 C3 129.2(3) . . ?
N1 C4 C5 108.5(3) . . ?
C3 C4 C5 122.3(3) . . ?
N2 C12 C13 124.8(4) . . ?
C2 C3 C4 118.5(3) . . ?
N2 C11 C10 123.3(4) . . ?
C3 C2 C1 119.5(4) . . ?
N1 C8 C7 111.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.94
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 983539'
