# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

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#                 Cambridge Crystallographic Data Centre
#                                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
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
5-amino-1-(4-bromophenyl)-1H-1,2,3-triazole-4-carbonitrile
 
;
_chemical_name_common            none

_chemical_formula_moiety         'C9 H6 Br N5'
_chemical_formula_sum            'C9 H6 Br N5'
_chemical_formula_weight         264.10

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   ' P 21/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                   20.471(14)
_cell_length_b                   3.8634(16)
_cell_length_c                   12.536(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.42(7)
_cell_angle_gamma                90.00
_cell_volume                     971.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    672
_cell_measurement_theta_min      3.1566
_cell_measurement_theta_max      29.4232

_exptl_crystal_description       'needle shaped'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      1.805
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    4.201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.20161
_exptl_absorpt_correction_T_max  1.00000
_exptl_special_details           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
 
;



_diffrn_ambient_temperature      293(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  'Xcalibur, Sapphire3'

_diffrn_detector_area_resol_mean 15.9853

_diffrn_reflns_number            6597
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1720
_reflns_number_gt                1288
_reflns_threshold_expression     >2sigma(I)


_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'


_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0931P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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_number_reflns         1720
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1641
_refine_ls_wR_factor_gt          0.1433
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_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 0.45197(3) 0.60017(17) 0.83408(5) 0.0608(3) Uani 1 1 d . . .
C4 C 0.3772(3) 0.5945(12) 0.9025(5) 0.0396(13) Uani 1 1 d . . .
N1 N 0.2138(2) 0.5985(10) 1.0510(3) 0.0394(11) Uani 1 1 d . . .
C1 C 0.2694(3) 0.5974(13) 0.9991(4) 0.0367(13) Uani 1 1 d . . .
C2 C 0.2642(3) 0.4584(13) 0.8961(4) 0.0385(13) Uani 1 1 d . . .
H2 H 0.2239 0.3674 0.8594 0.046 Uiso 1 1 calc R . .
N4 N 0.1288(2) 0.8464(13) 0.9177(4) 0.0532(14) Uani 1 1 d . . .
H4A H 0.1549 0.8666 0.8721 0.064 Uiso 1 1 calc R . .
H4B H 0.0881 0.9138 0.9001 0.064 Uiso 1 1 calc R . .
N2 N 0.2214(3) 0.4958(14) 1.1577(4) 0.0542(13) Uani 1 1 d . . .
N3 N 0.1658(3) 0.5424(14) 1.1884(4) 0.0527(13) Uani 1 1 d . . .
C3 C 0.3194(3) 0.4561(13) 0.8482(4) 0.0415(14) Uani 1 1 d . . .
H3 H 0.3169 0.3604 0.7795 0.050 Uiso 1 1 calc R . .
C7 C 0.1514(3) 0.7115(14) 1.0152(4) 0.0402(13) Uani 1 1 d . . .
C9 C 0.0556(3) 0.7519(18) 1.1143(4) 0.0523(15) Uani 1 1 d . . .
C6 C 0.3280(3) 0.7293(15) 1.0531(4) 0.0456(14) Uani 1 1 d . . .
H6 H 0.3311 0.8176 1.1229 0.055 Uiso 1 1 calc R . .
C8 C 0.1212(3) 0.6710(14) 1.1034(4) 0.0436(13) Uani 1 1 d . . .
C5 C 0.3830(3) 0.7331(15) 1.0049(5) 0.0472(14) Uani 1 1 d . . .
H5 H 0.4231 0.8275 1.0409 0.057 Uiso 1 1 calc R . .
N5 N 0.0040(3) 0.8168(18) 1.1210(5) 0.0792(19) 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 0.0537(5) 0.0628(5) 0.0715(6) 0.0043(3) 0.0261(4) 0.0027(3)
C4 0.045(3) 0.028(3) 0.047(3) 0.004(2) 0.012(3) 0.004(2)
N1 0.048(3) 0.043(3) 0.026(2) 0.0042(18) 0.006(2) 0.010(2)
C1 0.043(3) 0.037(3) 0.029(3) 0.001(2) 0.005(2) 0.009(2)
C2 0.048(4) 0.035(3) 0.030(3) 0.002(2) 0.002(2) -0.002(2)
N4 0.038(3) 0.084(4) 0.038(3) 0.017(2) 0.010(2) 0.021(3)
N2 0.058(4) 0.070(3) 0.033(3) 0.009(2) 0.007(2) 0.011(3)
N3 0.051(3) 0.074(3) 0.035(3) 0.007(2) 0.014(2) 0.010(3)
C3 0.061(4) 0.030(3) 0.036(3) -0.003(2) 0.015(3) 0.000(3)
C7 0.048(4) 0.041(3) 0.032(3) 0.003(2) 0.009(2) 0.000(3)
C9 0.062(5) 0.064(4) 0.032(3) 0.005(3) 0.013(3) 0.011(4)
C6 0.053(4) 0.047(3) 0.035(3) -0.002(2) 0.003(3) 0.005(3)
C8 0.045(3) 0.053(3) 0.034(3) 0.005(2) 0.009(2) 0.008(3)
C5 0.045(4) 0.044(3) 0.049(3) -0.007(3) 0.002(3) -0.004(3)
N5 0.067(5) 0.110(5) 0.067(4) 0.021(4) 0.029(3) 0.024(4)

_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 C4 1.897(6) . ?
C4 C3 1.354(8) . ?
C4 C5 1.374(8) . ?
N1 C7 1.339(7) . ?
N1 N2 1.374(6) . ?
N1 C1 1.419(7) . ?
C1 C6 1.355(8) . ?
C1 C2 1.383(7) . ?
C2 C3 1.381(8) . ?
C2 H2 0.9300 . ?
N4 C7 1.325(6) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N2 N3 1.285(7) . ?
N3 C8 1.354(7) . ?
C3 H3 0.9300 . ?
C7 C8 1.379(7) . ?
C9 N5 1.106(8) . ?
C9 C8 1.410(9) . ?
C6 C5 1.380(8) . ?
C6 H6 0.9300 . ?
C5 H5 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
C3 C4 C5 121.9(6) . . ?
C3 C4 Br1 118.7(4) . . ?
C5 C4 Br1 119.4(5) . . ?
C7 N1 N2 109.8(5) . . ?
C7 N1 C1 130.2(4) . . ?
N2 N1 C1 119.9(5) . . ?
C6 C1 C2 120.6(6) . . ?
C6 C1 N1 118.7(5) . . ?
C2 C1 N1 120.6(5) . . ?
C3 C2 C1 119.3(5) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C7 N4 H4A 120.0 . . ?
C7 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N3 N2 N1 108.3(5) . . ?
N2 N3 C8 108.4(5) . . ?
C4 C3 C2 119.3(5) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
N4 C7 N1 124.9(5) . . ?
N4 C7 C8 130.9(6) . . ?
N1 C7 C8 104.1(4) . . ?
N5 C9 C8 178.7(7) . . ?
C1 C6 C5 120.3(5) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N3 C8 C7 109.4(5) . . ?
N3 C8 C9 120.8(5) . . ?
C7 C8 C9 129.8(5) . . ?
C4 C5 C6 118.6(6) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?

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
C7 N1 C1 C6 129.4(6) . . . . ?
N2 N1 C1 C6 -45.1(7) . . . . ?
C7 N1 C1 C2 -51.8(7) . . . . ?
N2 N1 C1 C2 133.7(5) . . . . ?
C6 C1 C2 C3 -0.2(7) . . . . ?
N1 C1 C2 C3 -179.0(4) . . . . ?
C7 N1 N2 N3 0.0(6) . . . . ?
C1 N1 N2 N3 175.5(5) . . . . ?
N1 N2 N3 C8 0.7(7) . . . . ?
C5 C4 C3 C2 1.0(8) . . . . ?
Br1 C4 C3 C2 -178.4(4) . . . . ?
C1 C2 C3 C4 -0.9(8) . . . . ?
N2 N1 C7 N4 176.1(5) . . . . ?
C1 N1 C7 N4 1.2(9) . . . . ?
N2 N1 C7 C8 -0.6(6) . . . . ?
C1 N1 C7 C8 -175.5(5) . . . . ?
C2 C1 C6 C5 1.4(8) . . . . ?
N1 C1 C6 C5 -179.8(5) . . . . ?
N2 N3 C8 C7 -1.0(7) . . . . ?
N2 N3 C8 C9 -179.1(6) . . . . ?
N4 C7 C8 N3 -175.4(6) . . . . ?
N1 C7 C8 N3 1.0(6) . . . . ?
N4 C7 C8 C9 2.5(11) . . . . ?
N1 C7 C8 C9 178.8(6) . . . . ?
N5 C9 C8 N3 -175(100) . . . . ?
N5 C9 C8 C7 7(38) . . . . ?
C3 C4 C5 C6 0.1(8) . . . . ?
Br1 C4 C5 C6 179.5(4) . . . . ?
C1 C6 C5 C4 -1.3(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.105
_database_code_depnum_ccdc_archive 'CCDC 936406'