# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_exp_931
_database_code_depnum_ccdc_archive 'CCDC 979591'
_audit_update_record             
;
2014-01-06 deposited with the CCDC.
2015-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H11 N3 O3'
_chemical_formula_sum            'C7 H11 N3 O3'
_chemical_formula_weight         185.19

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'
O O 0.0106 0.0060 '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/n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9591(4)
_cell_length_b                   4.8417(3)
_cell_length_c                   23.7648(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.296(5)
_cell_angle_gamma                90.00
_cell_volume                     913.21(9)
_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       Needles
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\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            3611
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.44
_diffrn_reflns_theta_max         25.25
_reflns_number_total             1648
_reflns_number_gt                1385
_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)+(0.0376P)²+0.1006P] 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         1648
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
O1 O 0.22362(18) 0.6611(4) 0.55673(6) 0.0612(5) Uani 1 1 d . . .
H1 H 0.124(3) 0.611(6) 0.5608(11) 0.093(9) Uiso 1 1 d . . .
O2 O 0.35580(19) 0.5976(3) 0.28824(6) 0.0613(5) Uani 1 1 d . . .
O3 O 0.52899(16) 0.2688(3) 0.25931(5) 0.0487(4) Uani 1 1 d . . .
N1 N 0.12550(18) 0.4479(4) 0.43439(6) 0.0519(5) Uani 1 1 d . . .
N2 N 0.1790(2) 0.2899(4) 0.39441(7) 0.0551(5) Uani 1 1 d . . .
N3 N 0.34305(17) 0.3470(3) 0.39160(6) 0.0420(4) Uani 1 1 d . . .
C1 C 0.2341(3) 0.7985(5) 0.50465(9) 0.0562(6) Uani 1 1 d . . .
H1A H 0.135(3) 0.910(5) 0.4954(8) 0.064(6) Uiso 1 1 d . . .
H1B H 0.339(3) 0.933(5) 0.5068(9) 0.077(7) Uiso 1 1 d . . .
C2 C 0.2546(2) 0.6047(4) 0.45684(7) 0.0407(5) Uani 1 1 d . . .
C3 C 0.3940(2) 0.5414(4) 0.42958(7) 0.0419(5) Uani 1 1 d . . .
H3 H 0.512(2) 0.607(4) 0.4344(7) 0.048(5) Uiso 1 1 d . . .
C4 C 0.4378(3) 0.2165(5) 0.34903(8) 0.0451(5) Uani 1 1 d . . .
H4A H 0.549(3) 0.204(4) 0.3633(8) 0.059(6) Uiso 1 1 d . . .
H4B H 0.389(2) 0.042(5) 0.3404(8) 0.057(6) Uiso 1 1 d . . .
C5 C 0.4336(2) 0.3863(4) 0.29573(8) 0.0413(5) Uani 1 1 d . . .
C6 C 0.5304(4) 0.4016(7) 0.20414(10) 0.0624(7) Uani 1 1 d . . .
H6A H 0.418(4) 0.355(6) 0.1854(11) 0.114(10) Uiso 1 1 d . . .
H6B H 0.560(3) 0.596(6) 0.2100(10) 0.089(9) Uiso 1 1 d . . .
C7 C 0.6643(4) 0.2726(7) 0.17347(11) 0.0695(7) Uani 1 1 d . . .
H7A H 0.667(3) 0.358(5) 0.1361(11) 0.083(8) Uiso 1 1 d . . .
H7B H 0.774(4) 0.311(6) 0.1952(12) 0.117(11) Uiso 1 1 d . . .
H7C H 0.642(4) 0.071(7) 0.1701(12) 0.114(11) Uiso 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
O1 0.0379(7) 0.1061(14) 0.0403(8) -0.0069(8) 0.0077(6) -0.0016(9)
O2 0.0744(10) 0.0493(9) 0.0616(9) 0.0049(8) 0.0136(8) 0.0187(8)
O3 0.0549(8) 0.0545(9) 0.0386(7) 0.0058(7) 0.0160(6) 0.0119(7)
N1 0.0364(8) 0.0747(13) 0.0454(9) -0.0068(9) 0.0090(7) -0.0004(9)
N2 0.0423(9) 0.0738(13) 0.0505(10) -0.0100(10) 0.0108(7) -0.0112(9)
N3 0.0360(8) 0.0518(10) 0.0394(8) -0.0019(8) 0.0100(6) 0.0032(8)
C1 0.0519(12) 0.0640(15) 0.0546(13) -0.0070(12) 0.0174(10) 0.0083(12)
C2 0.0349(9) 0.0478(11) 0.0396(9) 0.0023(9) 0.0054(7) 0.0047(9)
C3 0.0357(9) 0.0505(12) 0.0401(10) -0.0033(9) 0.0062(8) 0.0017(9)
C4 0.0485(11) 0.0482(13) 0.0401(11) -0.0036(10) 0.0130(9) 0.0058(11)
C5 0.0395(9) 0.0414(11) 0.0432(10) -0.0017(9) 0.0043(8) 0.0017(9)
C6 0.0723(16) 0.0721(18) 0.0446(12) 0.0158(13) 0.0158(11) 0.0063(15)
C7 0.0731(17) 0.090(2) 0.0482(14) 0.0025(15) 0.0221(12) -0.0053(17)

_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
O1 C1 1.413(3) . ?
O2 C5 1.202(2) . ?
O3 C5 1.322(2) . ?
O3 C6 1.461(2) . ?
N1 N2 1.315(2) . ?
N1 C2 1.354(2) . ?
N2 N3 1.341(2) . ?
N3 C3 1.346(2) . ?
N3 C4 1.451(2) . ?
C1 C2 1.492(3) . ?
C2 C3 1.361(2) . ?
C4 C5 1.508(3) . ?
C6 C7 1.475(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
C5 O3 C6 116.18(17) . . ?
N2 N1 C2 109.48(15) . . ?
N1 N2 N3 106.57(15) . . ?
N2 N3 C3 110.88(15) . . ?
N2 N3 C4 120.24(17) . . ?
C3 N3 C4 128.76(16) . . ?
O1 C1 C2 112.8(2) . . ?
N1 C2 C3 107.92(17) . . ?
N1 C2 C1 121.98(17) . . ?
C3 C2 C1 130.06(18) . . ?
N3 C3 C2 105.14(16) . . ?
N3 C4 C5 111.61(17) . . ?
O2 C5 O3 125.74(18) . . ?
O2 C5 C4 124.55(18) . . ?
O3 C5 C4 109.71(17) . . ?
O3 C6 C7 108.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_ppg-pr1_0m
_database_code_depnum_ccdc_archive 'CCDC 1019691'
_audit_update_record             
;
2014-08-15 deposited with the CCDC.
2015-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 Br N5'
_chemical_formula_sum            'C23 H18 Br N5'
_chemical_formula_weight         444.32

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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.5296(11)
_cell_length_b                   17.3251(18)
_cell_length_c                   22.405(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4087.3(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1808
_exptl_absorpt_coefficient_mu    2.027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'

_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  '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            36336
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0673
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         26.61
_reflns_number_total             4219
_reflns_number_gt                1851
_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)+(0.1000P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4219
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1445
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1813
_refine_ls_wR_factor_gt          0.1389
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_restrained_S_all      0.930
_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 1.04869(6) 0.17176(4) -0.29608(2) 0.1113(4) Uani 1 1 d . . .
N1 N 1.0593(3) 0.23466(18) 0.00634(13) 0.0501(8) Uani 1 1 d . . .
N2 N 0.9357(3) 0.2498(2) 0.01218(16) 0.0643(10) Uani 1 1 d . . .
N3 N 0.9262(3) 0.3198(2) 0.03577(16) 0.0623(10) Uani 1 1 d . . .
N4 N 1.0638(3) 0.54524(18) 0.09837(13) 0.0479(8) Uani 1 1 d . . .
N5 N 1.1944(3) 0.44530(19) 0.08121(13) 0.0509(8) Uani 1 1 d . . .
C1 C 1.0621(4) 0.1710(2) -0.2118(2) 0.0642(12) Uani 1 1 d . . .
C2 C 1.1585(4) 0.2102(3) -0.1844(2) 0.0661(12) Uani 1 1 d . . .
H2 H 1.2160 0.2387 -0.2069 0.079 Uiso 1 1 calc R . .
C3 C 1.1697(3) 0.2068(2) -0.12302(19) 0.0592(11) Uani 1 1 d . . .
H3 H 1.2356 0.2333 -0.1045 0.071 Uiso 1 1 calc R . .
C4 C 1.0856(3) 0.1652(2) -0.08857(18) 0.0486(10) Uani 1 1 d . . .
C5 C 0.9887(4) 0.1269(2) -0.1168(2) 0.0622(11) Uani 1 1 d . . .
H5 H 0.9304 0.0991 -0.0942 0.075 Uiso 1 1 calc R . .
C6 C 0.9760(4) 0.1289(3) -0.1786(2) 0.0723(13) Uani 1 1 d . . .
H6 H 0.9104 0.1023 -0.1973 0.087 Uiso 1 1 calc R . .
C7 C 1.1000(4) 0.1622(2) -0.02191(18) 0.0585(11) Uani 1 1 d . . .
H7A H 1.0496 0.1199 -0.0063 0.070 Uiso 1 1 calc R . .
H7B H 1.1882 0.1524 -0.0120 0.070 Uiso 1 1 calc R . .
C8 C 1.1307(4) 0.2937(2) 0.02648(16) 0.0522(10) Uani 1 1 d . . .
H8 H 1.2189 0.2966 0.0274 0.063 Uiso 1 1 calc R . .
C9 C 1.0459(3) 0.3485(2) 0.04522(17) 0.0477(10) Uani 1 1 d . . .
C10 C 1.0713(3) 0.4252(2) 0.06873(15) 0.0457(9) Uani 1 1 d . . .
C11 C 0.9877(3) 0.4849(2) 0.07910(15) 0.0449(9) Uani 1 1 d . . .
C12 C 1.0348(4) 0.6200(2) 0.11368(18) 0.0587(11) Uani 1 1 d . . .
H12 H 0.9513 0.6374 0.1121 0.070 Uiso 1 1 calc R . .
C13 C 1.1283(4) 0.6676(2) 0.13088(19) 0.0683(12) Uani 1 1 d . . .
H13 H 1.1092 0.7182 0.1415 0.082 Uiso 1 1 calc R . .
C14 C 1.2556(4) 0.6418(3) 0.13310(19) 0.0692(12) Uani 1 1 d . . .
H14 H 1.3192 0.6754 0.1456 0.083 Uiso 1 1 calc R . .
C15 C 1.2855(4) 0.5686(2) 0.11724(18) 0.0629(11) Uani 1 1 d . . .
H15 H 1.3695 0.5521 0.1182 0.075 Uiso 1 1 calc R . .
C16 C 1.1890(3) 0.5183(2) 0.09947(16) 0.0485(10) Uani 1 1 d . . .
C17 C 0.8487(3) 0.4927(2) 0.06896(17) 0.0562(11) Uani 1 1 d . . .
H17A H 0.8149 0.4420 0.0596 0.067 Uiso 1 1 calc R . .
H17B H 0.8360 0.5249 0.0341 0.067 Uiso 1 1 calc R . .
C18 C 0.7712(3) 0.5262(2) 0.11995(18) 0.0517(10) Uani 1 1 d . . .
C19 C 0.7799(5) 0.4974(3) 0.1767(2) 0.0833(14) Uani 1 1 d . . .
H19 H 0.8356 0.4573 0.1852 0.100 Uiso 1 1 calc R . .
C20 C 0.7044(7) 0.5287(5) 0.2217(3) 0.122(2) Uani 1 1 d . . .
H20 H 0.7106 0.5091 0.2602 0.147 Uiso 1 1 calc R . .
C21 C 0.6229(7) 0.5867(5) 0.2105(4) 0.135(3) Uani 1 1 d . . .
H21 H 0.5723 0.6066 0.2409 0.161 Uiso 1 1 calc R . .
C22 C 0.6151(5) 0.6160(3) 0.1546(4) 0.107(2) Uani 1 1 d . . .
H22 H 0.5606 0.6571 0.1470 0.128 Uiso 1 1 calc R . .
C23 C 0.6865(4) 0.5858(2) 0.1090(2) 0.0710(13) Uani 1 1 d . . .
H23 H 0.6780 0.6054 0.0705 0.085 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 0.1529(7) 0.1193(6) 0.0617(4) -0.0071(3) -0.0110(3) -0.0349(4)
N1 0.0477(19) 0.052(2) 0.050(2) -0.0056(16) 0.0064(15) 0.0020(17)
N2 0.046(2) 0.064(2) 0.083(3) -0.016(2) 0.0112(17) -0.0035(18)
N3 0.048(2) 0.064(2) 0.075(3) -0.0182(19) 0.0110(17) -0.0013(17)
N4 0.0469(18) 0.049(2) 0.048(2) -0.0036(16) -0.0044(14) 0.0026(16)
N5 0.0412(18) 0.054(2) 0.057(2) -0.0059(16) -0.0003(15) -0.0011(15)
C1 0.071(3) 0.062(3) 0.060(3) -0.011(2) -0.001(2) -0.010(2)
C2 0.060(3) 0.072(3) 0.066(3) -0.002(2) 0.005(2) -0.015(2)
C3 0.048(2) 0.064(3) 0.065(3) -0.005(2) -0.010(2) -0.007(2)
C4 0.045(2) 0.043(2) 0.058(3) -0.009(2) 0.0092(19) 0.0011(18)
C5 0.061(3) 0.061(3) 0.065(3) -0.010(2) 0.008(2) -0.016(2)
C6 0.072(3) 0.066(3) 0.079(4) -0.020(3) -0.012(3) -0.015(2)
C7 0.063(3) 0.050(3) 0.062(3) -0.006(2) 0.003(2) 0.0047(19)
C8 0.044(2) 0.057(3) 0.055(3) -0.008(2) 0.0017(19) -0.002(2)
C9 0.043(2) 0.058(3) 0.043(2) -0.003(2) 0.0041(17) 0.001(2)
C10 0.046(2) 0.054(3) 0.038(2) -0.0027(19) 0.0021(17) 0.0009(19)
C11 0.045(2) 0.051(2) 0.039(2) -0.0038(18) -0.0011(17) 0.0040(19)
C12 0.059(3) 0.048(3) 0.069(3) -0.008(2) -0.004(2) 0.008(2)
C13 0.072(3) 0.053(3) 0.080(3) -0.015(2) -0.004(2) 0.007(2)
C14 0.065(3) 0.057(3) 0.085(3) -0.005(3) -0.003(2) -0.013(2)
C15 0.055(2) 0.063(3) 0.070(3) -0.002(2) -0.002(2) -0.005(2)
C16 0.046(2) 0.048(3) 0.051(2) -0.001(2) -0.0018(18) 0.0006(19)
C17 0.043(2) 0.071(3) 0.055(2) -0.005(2) -0.0038(19) 0.0068(19)
C18 0.045(2) 0.052(3) 0.058(3) -0.007(2) -0.0002(19) -0.0012(19)
C19 0.093(4) 0.096(4) 0.061(3) -0.004(3) 0.009(3) 0.005(3)
C20 0.118(5) 0.176(7) 0.073(4) -0.030(5) 0.030(4) -0.017(5)
C21 0.081(5) 0.181(9) 0.141(7) -0.089(7) 0.050(5) -0.025(5)
C22 0.053(3) 0.090(4) 0.178(6) -0.062(5) 0.015(4) 0.006(3)
C23 0.050(2) 0.062(3) 0.101(4) -0.006(3) 0.003(3) 0.005(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 C1 1.894(4) . ?
N1 N2 1.335(4) . ?
N1 C8 1.347(4) . ?
N1 C7 1.469(5) . ?
N2 N3 1.326(4) . ?
N3 C9 1.372(4) . ?
N4 C12 1.375(5) . ?
N4 C11 1.386(4) . ?
N4 C16 1.399(4) . ?
N5 C16 1.330(5) . ?
N5 C10 1.370(4) . ?
C1 C2 1.366(6) . ?
C1 C6 1.381(6) . ?
C2 C3 1.382(5) . ?
C3 C4 1.378(5) . ?
C4 C5 1.372(5) . ?
C4 C7 1.502(5) . ?
C5 C6 1.391(6) . ?
C8 C9 1.369(5) . ?
C9 C10 1.454(5) . ?
C10 C11 1.378(5) . ?
C11 C17 1.487(5) . ?
C12 C13 1.340(5) . ?
C13 C14 1.414(6) . ?
C14 C15 1.354(5) . ?
C15 C16 1.398(5) . ?
C17 C18 1.519(5) . ?
C18 C19 1.369(6) . ?
C18 C23 1.387(5) . ?
C19 C20 1.393(8) . ?
C20 C21 1.346(10) . ?
C21 C22 1.353(9) . ?
C22 C23 1.373(7) . ?

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
N2 N1 C8 111.2(3) . . ?
N2 N1 C7 119.6(3) . . ?
C8 N1 C7 129.1(3) . . ?
N3 N2 N1 107.0(3) . . ?
N2 N3 C9 108.9(3) . . ?
C12 N4 C11 131.4(3) . . ?
C12 N4 C16 121.3(3) . . ?
C11 N4 C16 107.3(3) . . ?
C16 N5 C10 105.3(3) . . ?
C2 C1 C6 120.6(4) . . ?
C2 C1 Br1 120.0(3) . . ?
C6 C1 Br1 119.4(3) . . ?
C1 C2 C3 119.3(4) . . ?
C4 C3 C2 121.6(4) . . ?
C5 C4 C3 118.2(4) . . ?
C5 C4 C7 121.1(4) . . ?
C3 C4 C7 120.7(4) . . ?
C4 C5 C6 121.2(4) . . ?
C1 C6 C5 119.0(4) . . ?
N1 C7 C4 111.7(3) . . ?
N1 C8 C9 105.4(3) . . ?
C8 C9 N3 107.5(3) . . ?
C8 C9 C10 128.7(3) . . ?
N3 C9 C10 123.8(3) . . ?
N5 C10 C11 112.3(3) . . ?
N5 C10 C9 118.7(3) . . ?
C11 C10 C9 129.0(3) . . ?
C10 C11 N4 104.4(3) . . ?
C10 C11 C17 132.2(3) . . ?
N4 C11 C17 123.2(3) . . ?
C13 C12 N4 119.2(4) . . ?
C12 C13 C14 120.8(4) . . ?
C15 C14 C13 120.5(4) . . ?
C14 C15 C16 119.3(4) . . ?
N5 C16 C15 130.5(3) . . ?
N5 C16 N4 110.7(3) . . ?
C15 C16 N4 118.8(4) . . ?
C11 C17 C18 116.6(3) . . ?
C19 C18 C23 118.6(4) . . ?
C19 C18 C17 121.5(4) . . ?
C23 C18 C17 119.8(4) . . ?
C18 C19 C20 119.5(5) . . ?
C21 C20 C19 121.3(7) . . ?
C20 C21 C22 119.4(6) . . ?
C21 C22 C23 120.9(6) . . ?
C22 C23 C18 120.2(5) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        26.61
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.049
