# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1559412'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 Br N2'
_chemical_formula_weight         273.13

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           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6418(4)
_cell_length_b                   9.2290(5)
_cell_length_c                   16.4366(10)
_cell_angle_alpha                96.591(2)
_cell_angle_beta                 93.902(2)
_cell_angle_gamma                105.608(2)
_cell_volume                     1103.14(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    3.696
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.4035
_exptl_absorpt_correction_T_max  0.5252
_exptl_absorpt_process_details   '(XCAD4; Harms & Wocadlo, 1995)'

_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  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8120
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3860
_reflns_number_gt                3103
_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)+(0.0375P)²+0.0246P] 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         3860
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0773
_refine_ls_wR_factor_gt          0.0736
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 1.42707(4) 0.81151(4) 0.54717(2) 0.02838(11) Uani 1 1 d . . .
Br2 Br 1.15962(4) 0.33108(4) 0.88708(2) 0.02995(11) Uani 1 1 d . . .
C3 C 0.7415(4) 0.4613(4) 0.2979(2) 0.0313(8) Uani 1 1 d . . .
H3 H 0.6804 0.3972 0.2508 0.038 Uiso 1 1 calc R . .
C6 C 1.2017(4) 0.7219(3) 0.48342(19) 0.0223(7) Uani 1 1 d . . .
C16 C 0.8074(4) 0.8774(4) 0.9076(2) 0.0296(8) Uani 1 1 d . . .
H16 H 0.8067 0.9787 0.9148 0.036 Uiso 1 1 calc R . .
N4 N 1.1091(3) 0.6263(3) 0.90223(15) 0.0241(6) Uani 1 1 d . . .
N1 N 0.9148(3) 0.6461(3) 0.43940(15) 0.0204(6) Uani 1 1 d . . .
N2 N 1.1941(3) 0.6270(3) 0.41286(15) 0.0229(6) Uani 1 1 d . . .
C18 C 0.9716(4) 0.6893(4) 0.90032(18) 0.0235(8) Uani 1 1 d . . .
N3 N 0.8030(3) 0.5785(3) 0.88449(15) 0.0206(6) Uani 1 1 d . . .
C19 C 1.0253(4) 0.4736(3) 0.88826(18) 0.0215(7) Uani 1 1 d . . .
C20 C 0.8387(4) 0.4391(3) 0.87652(18) 0.0196(7) Uani 1 1 d . . .
C9 C 0.8404(4) 0.7562(4) 0.61810(19) 0.0228(7) Uani 1 1 d . . .
H9 H 0.7737 0.6555 0.6017 0.027 Uiso 1 1 calc R . .
C13 C 1.0799(4) 0.9761(3) 0.59962(19) 0.0235(7) Uani 1 1 d . . .
H13 H 1.1738 1.0237 0.5704 0.028 Uiso 1 1 calc R . .
C1 C 0.7291(4) 0.6235(3) 0.4221(2) 0.0257(8) Uani 1 1 d . . .
H1 H 0.6647 0.6698 0.4579 0.031 Uiso 1 1 calc R . .
C7 C 1.0372(4) 0.7381(3) 0.50381(19) 0.0200(7) Uani 1 1 d . . .
C10 C 0.7980(4) 0.8379(4) 0.6856(2) 0.0283(8) Uani 1 1 d . . .
H10 H 0.7024 0.7919 0.7144 0.034 Uiso 1 1 calc R . .
C21 C 0.6894(4) 0.2946(3) 0.85548(19) 0.0204(7) Uani 1 1 d . . .
C8 C 0.9837(4) 0.8243(3) 0.57416(19) 0.0208(7) Uani 1 1 d . . .
C15 C 0.6393(4) 0.7617(4) 0.89281(19) 0.0272(8) Uani 1 1 d . . .
H15 H 0.5295 0.7872 0.8909 0.033 Uiso 1 1 calc R . .
C2 C 0.6421(4) 0.5324(4) 0.3519(2) 0.0291(8) Uani 1 1 d . . .
H2 H 0.5173 0.5167 0.3393 0.035 Uiso 1 1 calc R . .
C12 C 1.0366(4) 1.0560(4) 0.6678(2) 0.0260(8) Uani 1 1 d . . .
H12 H 1.1027 1.1566 0.6848 0.031 Uiso 1 1 calc R . .
C22 C 0.6044(4) 0.2207(3) 0.9169(2) 0.0258(8) Uani 1 1 d . . .
H22 H 0.6433 0.2588 0.9719 0.031 Uiso 1 1 calc R . .
C17 C 0.9686(4) 0.8429(4) 0.9112(2) 0.0299(8) Uani 1 1 d . . .
H17 H 1.0777 0.9202 0.9209 0.036 Uiso 1 1 calc R . .
C14 C 0.6387(4) 0.6141(4) 0.88150(19) 0.0244(7) Uani 1 1 d . . .
H14 H 0.5290 0.5375 0.8718 0.029 Uiso 1 1 calc R . .
C11 C 0.8955(4) 0.9872(4) 0.7110(2) 0.0297(8) Uani 1 1 d . . .
H11 H 0.8665 1.0413 0.7570 0.036 Uiso 1 1 calc R . .
C23 C 0.4610(4) 0.0895(4) 0.8961(2) 0.0301(8) Uani 1 1 d . . .
H23 H 0.4039 0.0399 0.9374 0.036 Uiso 1 1 calc R . .
C5 C 1.0160(4) 0.5820(3) 0.38586(19) 0.0225(7) Uani 1 1 d . . .
C24 C 0.4025(4) 0.0323(4) 0.8152(2) 0.0294(8) Uani 1 1 d . . .
H24 H 0.3062 -0.0557 0.8017 0.035 Uiso 1 1 calc R . .
C4 C 0.9230(4) 0.4855(4) 0.31419(19) 0.0268(8) Uani 1 1 d . . .
H4 H 0.9868 0.4389 0.2783 0.032 Uiso 1 1 calc R . .
C25 C 0.4871(4) 0.1056(4) 0.7541(2) 0.0333(9) Uani 1 1 d . . .
H25 H 0.4482 0.0666 0.6992 0.040 Uiso 1 1 calc R . .
C26 C 0.6297(4) 0.2368(4) 0.7740(2) 0.0286(8) Uani 1 1 d . . .
H26 H 0.6855 0.2863 0.7324 0.034 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 C6 1.881(3) . ?
Br2 C19 1.873(3) . ?
C3 C4 1.347(4) . ?
C3 C2 1.422(4) . ?
C6 N2 1.358(4) . ?
C6 C7 1.365(4) . ?
C16 C17 1.353(5) . ?
C16 C15 1.418(4) . ?
N4 C18 1.331(4) . ?
N4 C19 1.368(4) . ?
N1 C1 1.382(4) . ?
N1 C5 1.393(4) . ?
N1 C7 1.396(4) . ?
N2 C5 1.339(4) . ?
C18 N3 1.399(4) . ?
C18 C17 1.414(4) . ?
N3 C14 1.380(4) . ?
N3 C20 1.379(4) . ?
C19 C20 1.370(4) . ?
C20 C21 1.490(4) . ?
C9 C10 1.375(4) . ?
C9 C8 1.399(4) . ?
C13 C12 1.378(4) . ?
C13 C8 1.395(4) . ?
C1 C2 1.360(4) . ?
C7 C8 1.472(4) . ?
C10 C11 1.379(4) . ?
C21 C26 1.382(4) . ?
C21 C22 1.384(4) . ?
C15 C14 1.352(4) . ?
C12 C11 1.382(4) . ?
C22 C23 1.387(4) . ?
C23 C24 1.370(5) . ?
C5 C4 1.411(4) . ?
C24 C25 1.376(5) . ?
C25 C26 1.382(4) . ?

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
C4 C3 C2 120.8(3) . . ?
N2 C6 C7 115.0(3) . . ?
N2 C6 Br1 119.7(2) . . ?
C7 C6 Br1 125.2(2) . . ?
C17 C16 C15 121.0(3) . . ?
C18 N4 C19 104.1(2) . . ?
C1 N1 C5 121.9(3) . . ?
C1 N1 C7 130.6(3) . . ?
C5 N1 C7 107.4(2) . . ?
C5 N2 C6 103.4(2) . . ?
N4 C18 N3 111.2(3) . . ?
N4 C18 C17 131.7(3) . . ?
N3 C18 C17 117.1(3) . . ?
C14 N3 C20 130.2(2) . . ?
C14 N3 C18 122.6(3) . . ?
C20 N3 C18 107.1(2) . . ?
N4 C19 C20 113.3(3) . . ?
N4 C19 Br2 121.6(2) . . ?
C20 C19 Br2 125.1(2) . . ?
C19 C20 N3 104.3(3) . . ?
C19 C20 C21 134.0(3) . . ?
N3 C20 C21 121.7(2) . . ?
C10 C9 C8 120.1(3) . . ?
C12 C13 C8 120.5(3) . . ?
C2 C1 N1 118.9(3) . . ?
C6 C7 N1 102.9(2) . . ?
C6 C7 C8 132.8(3) . . ?
N1 C7 C8 124.3(3) . . ?
C9 C10 C11 120.8(3) . . ?
C26 C21 C22 119.4(3) . . ?
C26 C21 C20 119.9(3) . . ?
C22 C21 C20 120.6(3) . . ?
C9 C8 C13 118.7(3) . . ?
C9 C8 C7 121.3(3) . . ?
C13 C8 C7 119.9(2) . . ?
C14 C15 C16 120.0(3) . . ?
C1 C2 C3 120.1(3) . . ?
C11 C12 C13 120.3(3) . . ?
C23 C22 C21 119.8(3) . . ?
C16 C17 C18 120.1(3) . . ?
C15 C14 N3 119.2(3) . . ?
C12 C11 C10 119.6(3) . . ?
C24 C23 C22 120.6(3) . . ?
N2 C5 N1 111.3(3) . . ?
N2 C5 C4 130.3(3) . . ?
N1 C5 C4 118.4(3) . . ?
C23 C24 C25 119.7(3) . . ?
C3 C4 C5 119.8(3) . . ?
C24 C25 C26 120.4(3) . . ?
C21 C26 C25 120.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.079
