# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_shrv271
_database_code_depnum_ccdc_archive 'CCDC 1049473'
_audit_update_record             
;
2015-02-14 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_date             2014-10-21
_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'
_chemical_name_systematic        
; 
 7H-[1,2,4]triazolo[4,3-b][1,2,4]triazole-3,6,7-triamine 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H6 N8'
_chemical_formula_sum            'C3 H6 N8'
_chemical_formula_weight         154.16

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'

_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                   6.2275(11)
_cell_length_b                   7.0170(12)
_cell_length_c                   7.9510(13)
_cell_angle_alpha                75.693(2)
_cell_angle_beta                 69.567(2)
_cell_angle_gamma                64.206(2)
_cell_volume                     291.27(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             160
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_T_max  0.9816

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3075
_diffrn_reflns_av_R_equivalents  0.0111
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         28.24
_reflns_number_total             1424
_reflns_number_gt                1288
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'

_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)+(0.0565P)²+0.1378P] 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         1424
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
N1 N 0.11086(18) 0.22030(16) 0.56423(13) 0.0119(2) Uani 1 1 d . . .
N2 N 0.05024(18) 0.24604(17) 0.40358(13) 0.0130(2) Uani 1 1 d . . .
C3 C 0.2351(2) 0.29244(19) 0.28229(16) 0.0125(3) Uani 1 1 d . . .
N4 N 0.39967(19) 0.30314(17) 0.35732(13) 0.0131(2) Uani 1 1 d . . .
C5 C 0.3197(2) 0.25061(18) 0.53973(16) 0.0117(3) Uani 1 1 d . . .
N6 N 0.38099(19) 0.21966(17) 0.68805(14) 0.0138(2) Uani 1 1 d . . .
N7 N 0.18544(19) 0.16781(17) 0.82472(14) 0.0139(2) Uani 1 1 d . . .
C8 C 0.0269(2) 0.17154(18) 0.74655(15) 0.0119(3) Uani 1 1 d . . .
N9 N 0.2688(2) 0.33075(18) 0.10361(14) 0.0172(3) Uani 1 1 d . . .
H9A H 0.401(3) 0.356(3) 0.035(2) 0.021 Uiso 1 1 d . . .
H9B H 0.183(3) 0.297(3) 0.053(2) 0.021 Uiso 1 1 d . . .
N10 N 0.6058(2) 0.35477(18) 0.25704(14) 0.0157(2) Uani 1 1 d . . .
H10A H 0.578(3) 0.481(3) 0.284(2) 0.019 Uiso 1 1 d . . .
H10B H 0.735(3) 0.266(3) 0.294(2) 0.019 Uiso 1 1 d . . .
N11 N -0.19041(19) 0.14459(18) 0.82962(14) 0.0154(2) Uani 1 1 d . . .
H11A H -0.268(3) 0.135(3) 0.762(2) 0.018 Uiso 1 1 d . . .
H11B H -0.205(3) 0.073(3) 0.936(2) 0.018 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
N1 0.0126(5) 0.0178(5) 0.0092(5) -0.0002(4) -0.0045(4) -0.0086(4)
N2 0.0149(5) 0.0202(5) 0.0080(5) -0.0007(4) -0.0050(4) -0.0093(4)
C3 0.0141(5) 0.0140(5) 0.0120(5) -0.0016(4) -0.0050(4) -0.0066(4)
N4 0.0136(5) 0.0201(5) 0.0098(5) -0.0003(4) -0.0034(4) -0.0108(4)
C5 0.0112(5) 0.0143(5) 0.0120(5) -0.0010(4) -0.0036(4) -0.0068(4)
N6 0.0141(5) 0.0191(5) 0.0111(5) -0.0001(4) -0.0042(4) -0.0093(4)
N7 0.0144(5) 0.0194(5) 0.0108(5) -0.0006(4) -0.0041(4) -0.0091(4)
C8 0.0135(5) 0.0134(5) 0.0094(5) -0.0015(4) -0.0033(4) -0.0054(4)
N9 0.0213(6) 0.0278(6) 0.0088(5) -0.0002(4) -0.0039(4) -0.0161(5)
N10 0.0142(5) 0.0199(5) 0.0162(5) -0.0007(4) -0.0025(4) -0.0116(4)
N11 0.0151(5) 0.0251(6) 0.0099(5) -0.0002(4) -0.0039(4) -0.0117(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
N1 C5 1.3484(15) . ?
N1 C8 1.3687(14) . ?
N1 N2 1.4036(13) . ?
N2 C3 1.3258(15) . ?
C3 N9 1.3368(15) . ?
C3 N4 1.3882(15) . ?
N4 C5 1.3706(15) . ?
N4 N10 1.4009(13) . ?
C5 N6 1.3035(15) . ?
N6 N7 1.4361(14) . ?
N7 C8 1.3267(15) . ?
C8 N11 1.3565(15) . ?
N9 H9A 0.876(17) . ?
N9 H9B 0.896(17) . ?
N10 H10A 0.893(18) . ?
N10 H10B 0.872(18) . ?
N11 H11A 0.866(18) . ?
N11 H11B 0.869(17) . ?

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 N1 C8 105.43(10) . . ?
C5 N1 N2 113.89(10) . . ?
C8 N1 N2 140.67(10) . . ?
C3 N2 N1 101.18(9) . . ?
N2 C3 N9 126.07(11) . . ?
N2 C3 N4 113.59(10) . . ?
N9 C3 N4 120.33(11) . . ?
C5 N4 C3 106.31(10) . . ?
C5 N4 N10 129.55(10) . . ?
C3 N4 N10 124.13(10) . . ?
N6 C5 N1 114.00(11) . . ?
N6 C5 N4 141.04(11) . . ?
N1 C5 N4 104.95(10) . . ?
C5 N6 N7 103.26(9) . . ?
C8 N7 N6 108.76(10) . . ?
N7 C8 N11 127.12(11) . . ?
N7 C8 N1 108.52(10) . . ?
N11 C8 N1 124.27(11) . . ?
C3 N9 H9A 118.4(11) . . ?
C3 N9 H9B 120.2(10) . . ?
H9A N9 H9B 119.3(15) . . ?
N4 N10 H10A 107.9(10) . . ?
N4 N10 H10B 109.3(11) . . ?
H10A N10 H10B 104.9(15) . . ?
C8 N11 H11A 117.7(11) . . ?
C8 N11 H11B 117.2(11) . . ?
H11A N11 H11B 117.0(15) . . ?

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
C5 N1 N2 C3 0.24(13) . . . . ?
C8 N1 N2 C3 -179.34(15) . . . . ?
N1 N2 C3 N9 179.33(12) . . . . ?
N1 N2 C3 N4 -1.81(13) . . . . ?
N2 C3 N4 C5 2.73(14) . . . . ?
N9 C3 N4 C5 -178.33(11) . . . . ?
N2 C3 N4 N10 -178.34(10) . . . . ?
N9 C3 N4 N10 0.60(18) . . . . ?
C8 N1 C5 N6 1.95(14) . . . . ?
N2 N1 C5 N6 -177.78(10) . . . . ?
C8 N1 C5 N4 -178.92(9) . . . . ?
N2 N1 C5 N4 1.35(14) . . . . ?
C3 N4 C5 N6 176.42(16) . . . . ?
N10 N4 C5 N6 -2.4(3) . . . . ?
C3 N4 C5 N1 -2.31(13) . . . . ?
N10 N4 C5 N1 178.84(11) . . . . ?
N1 C5 N6 N7 -1.37(14) . . . . ?
N4 C5 N6 N7 179.97(15) . . . . ?
C5 N6 N7 C8 0.24(13) . . . . ?
N6 N7 C8 N11 -175.57(11) . . . . ?
N6 N7 C8 N1 0.91(13) . . . . ?
C5 N1 C8 N7 -1.67(13) . . . . ?
N2 N1 C8 N7 177.93(13) . . . . ?
C5 N1 C8 N11 174.93(11) . . . . ?
N2 N1 C8 N11 -5.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9A N11 0.876(17) 2.523(17) 3.2014(16) 134.9(15) 1_654
N9 H9B N7 0.896(17) 2.217(17) 3.0112(15) 147.5(14) 1_554
N10 H10A N6 0.893(18) 2.293(18) 3.1619(16) 164.3(14) 2_666
N10 H10B N2 0.872(18) 2.351(17) 3.0942(15) 143.2(14) 1_655
N11 H11A N6 0.866(18) 2.254(17) 3.0413(15) 151.2(14) 1_455
N11 H11B N7 0.869(17) 2.208(17) 3.0631(15) 167.8(15) 2_557

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.24
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_shrv272
_database_code_depnum_ccdc_archive 'CCDC 1049474'
_audit_update_record             
;
2015-02-14 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_date             2014-10-23
_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'
_chemical_name_systematic        
'3,6,7-triamino-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazol-2-ium  3,4,5-trinitropyrazol-1-ide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H7 N8 +1, C3 N5 O6 -1'
_chemical_formula_sum            'C6 H7 N13 O6'
_chemical_formula_weight         357.25

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.311(2)
_cell_length_b                   8.265(3)
_cell_length_c                   13.717(5)
_cell_angle_alpha                73.487(5)
_cell_angle_beta                 80.058(4)
_cell_angle_gamma                79.551(5)
_cell_volume                     669.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.997

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5938
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_sigmaI/netI    0.1175
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         27.52
_reflns_number_total             2919
_reflns_number_gt                1548
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'

_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)+(0.0655P)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         2919
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1439
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1472
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_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
N1 N -0.4096(4) 0.3540(4) 0.4105(2) 0.0270(7) Uani 1 1 d . . .
N2 N -0.1976(4) 0.3009(4) 0.3831(2) 0.0262(7) Uani 1 1 d . . .
C3 C -0.1482(5) 0.3840(4) 0.2850(3) 0.0205(8) Uani 1 1 d . . .
C4 C -0.3261(5) 0.4904(4) 0.2449(2) 0.0192(8) Uani 1 1 d . . .
C5 C -0.4852(5) 0.4667(4) 0.3278(2) 0.0212(8) Uani 1 1 d . . .
N6 N 0.0638(4) 0.3501(4) 0.2296(2) 0.0242(7) Uani 1 1 d . . .
O7 O 0.2067(4) 0.2552(3) 0.2780(2) 0.0334(7) Uani 1 1 d . . .
O8 O 0.0877(4) 0.4152(3) 0.13655(19) 0.0311(7) Uani 1 1 d . . .
N9 N -0.3410(4) 0.5966(4) 0.1417(2) 0.0256(7) Uani 1 1 d . . .
O10 O -0.2536(4) 0.7258(3) 0.11544(18) 0.0319(7) Uani 1 1 d . . .
O11 O -0.4410(4) 0.5503(4) 0.08751(19) 0.0401(7) Uani 1 1 d . . .
N12 N -0.7090(4) 0.5460(4) 0.3334(2) 0.0281(8) Uani 1 1 d . . .
O13 O -0.7643(4) 0.6544(4) 0.2567(2) 0.0341(7) Uani 1 1 d . . .
O14 O -0.8285(4) 0.4979(3) 0.4139(2) 0.0369(7) Uani 1 1 d . . .
N15 N -0.1849(4) -0.0323(4) 0.27522(19) 0.0184(7) Uani 1 1 d . . .
N16 N -0.0637(4) 0.0625(4) 0.1882(2) 0.0212(7) Uani 1 1 d . . .
C17 C -0.2056(5) 0.1090(4) 0.1221(2) 0.0205(8) Uani 1 1 d . . .
N18 N -0.4058(4) 0.0549(4) 0.1611(2) 0.0199(7) Uani 1 1 d . . .
C19 C -0.3902(5) -0.0368(4) 0.2596(2) 0.0206(8) Uani 1 1 d . . .
N20 N -0.5050(4) -0.1211(4) 0.3397(2) 0.0261(8) Uani 1 1 d . . .
N21 N -0.3551(4) -0.1696(4) 0.4118(2) 0.0254(7) Uani 1 1 d . . .
H21 H -0.3851 -0.2295 0.4754 0.030 Uiso 1 1 calc R . .
C22 C -0.1623(5) -0.1153(4) 0.3736(2) 0.0189(8) Uani 1 1 d . . .
N23 N -0.1714(5) 0.1969(4) 0.0231(2) 0.0298(8) Uani 1 1 d . . .
H23A H -0.298(6) 0.267(5) -0.008(3) 0.036 Uiso 1 1 d . . .
H23B H -0.057(6) 0.234(5) 0.004(3) 0.036 Uiso 1 1 d . . .
N24 N -0.5706(5) 0.0745(5) 0.1008(2) 0.0298(8) Uani 1 1 d . . .
H24A H -0.572(6) -0.028(5) 0.093(3) 0.036 Uiso 1 1 d . . .
H24B H -0.678(6) 0.122(5) 0.125(3) 0.036 Uiso 1 1 d . . .
N25 N 0.0080(4) -0.1307(4) 0.4211(2) 0.0237(7) Uani 1 1 d . . .
H25A H 0.008(5) -0.192(5) 0.486(3) 0.028 Uiso 1 1 d . . .
H25B H 0.115(6) -0.107(5) 0.386(3) 0.028 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
N1 0.0237(16) 0.032(2) 0.0231(16) -0.0017(14) -0.0039(12) -0.0052(13)
N2 0.0207(15) 0.0296(19) 0.0239(17) 0.0011(14) -0.0064(12) -0.0020(13)
C3 0.0123(16) 0.022(2) 0.028(2) -0.0062(16) -0.0051(13) -0.0028(14)
C4 0.0132(16) 0.021(2) 0.0233(19) -0.0010(15) -0.0051(13) -0.0070(13)
C5 0.0132(16) 0.025(2) 0.0243(19) -0.0035(16) 0.0004(13) -0.0070(14)
N6 0.0126(14) 0.0241(18) 0.0377(19) -0.0082(15) -0.0070(12) -0.0033(12)
O7 0.0176(13) 0.0311(16) 0.0537(17) -0.0125(13) -0.0145(11) 0.0032(11)
O8 0.0233(13) 0.0368(17) 0.0301(16) -0.0047(13) 0.0036(10) -0.0092(11)
N9 0.0199(15) 0.0267(19) 0.0280(18) -0.0039(15) -0.0040(13) -0.0019(13)
O10 0.0341(15) 0.0242(16) 0.0330(15) 0.0024(12) -0.0042(11) -0.0091(12)
O11 0.0470(17) 0.050(2) 0.0277(15) -0.0025(13) -0.0206(12) -0.0164(14)
N12 0.0162(15) 0.035(2) 0.0376(19) -0.0131(16) -0.0041(13) -0.0084(13)
O13 0.0225(14) 0.0381(17) 0.0419(17) -0.0081(14) -0.0158(11) 0.0028(11)
O14 0.0231(14) 0.0446(18) 0.0420(17) -0.0132(14) 0.0091(12) -0.0115(12)
N15 0.0083(13) 0.0238(17) 0.0196(15) 0.0014(13) -0.0034(10) -0.0035(11)
N16 0.0155(14) 0.0251(18) 0.0190(15) 0.0043(13) -0.0030(11) -0.0084(12)
C17 0.0149(16) 0.022(2) 0.0231(19) -0.0031(16) -0.0035(13) -0.0026(14)
N18 0.0127(13) 0.0280(18) 0.0183(15) -0.0014(13) -0.0073(11) -0.0035(12)
C19 0.0110(16) 0.024(2) 0.027(2) -0.0062(16) -0.0058(13) -0.0023(14)
N20 0.0127(14) 0.039(2) 0.0223(16) 0.0040(14) -0.0055(11) -0.0075(13)
N21 0.0139(14) 0.039(2) 0.0195(15) 0.0034(14) -0.0058(11) -0.0073(12)
C22 0.0135(16) 0.019(2) 0.0220(19) -0.0007(15) -0.0043(13) -0.0026(13)
N23 0.0218(16) 0.036(2) 0.0248(18) 0.0063(15) -0.0032(13) -0.0089(14)
N24 0.0143(15) 0.045(2) 0.0304(18) -0.0096(17) -0.0123(12) 0.0034(15)
N25 0.0140(14) 0.035(2) 0.0198(16) 0.0003(14) -0.0051(11) -0.0071(13)

_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
N1 C5 1.344(4) . ?
N1 N2 1.353(4) . ?
N2 C3 1.338(4) . ?
C3 C4 1.384(4) . ?
C3 N6 1.442(4) . ?
C4 C5 1.374(4) . ?
C4 N9 1.448(4) . ?
C5 N12 1.444(4) . ?
N6 O8 1.231(3) . ?
N6 O7 1.234(3) . ?
N9 O10 1.225(4) . ?
N9 O11 1.228(4) . ?
N12 O13 1.228(4) . ?
N12 O14 1.231(4) . ?
N15 C22 1.347(4) . ?
N15 C19 1.358(4) . ?
N15 N16 1.413(3) . ?
N16 C17 1.315(4) . ?
C17 N23 1.346(4) . ?
C17 N18 1.384(4) . ?
N18 C19 1.359(4) . ?
N18 N24 1.397(4) . ?
C19 N20 1.300(4) . ?
N20 N21 1.412(4) . ?
N21 C22 1.342(4) . ?
N21 H21 0.8800 . ?
C22 N25 1.319(4) . ?
N23 H23A 0.98(4) . ?
N23 H23B 0.81(4) . ?
N24 H24A 0.88(4) . ?
N24 H24B 0.79(4) . ?
N25 H25A 0.89(4) . ?
N25 H25B 0.78(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 N1 N2 107.5(2) . . ?
C3 N2 N1 106.9(2) . . ?
N2 C3 C4 111.9(3) . . ?
N2 C3 N6 121.4(3) . . ?
C4 C3 N6 126.5(3) . . ?
C5 C4 C3 102.2(3) . . ?
C5 C4 N9 129.1(3) . . ?
C3 C4 N9 128.7(3) . . ?
N1 C5 C4 111.5(3) . . ?
N1 C5 N12 120.3(3) . . ?
C4 C5 N12 128.1(3) . . ?
O8 N6 O7 124.6(3) . . ?
O8 N6 C3 117.3(2) . . ?
O7 N6 C3 118.1(3) . . ?
O10 N9 O11 125.2(3) . . ?
O10 N9 C4 117.4(3) . . ?
O11 N9 C4 117.3(3) . . ?
O13 N12 O14 125.6(3) . . ?
O13 N12 C5 116.9(3) . . ?
O14 N12 C5 117.5(3) . . ?
C22 N15 C19 108.1(2) . . ?
C22 N15 N16 138.8(2) . . ?
C19 N15 N16 113.0(2) . . ?
C17 N16 N15 101.1(2) . . ?
N16 C17 N23 126.5(3) . . ?
N16 C17 N18 114.3(3) . . ?
N23 C17 N18 119.2(3) . . ?
C19 N18 C17 106.4(2) . . ?
C19 N18 N24 129.7(3) . . ?
C17 N18 N24 123.2(3) . . ?
N20 C19 N15 113.7(3) . . ?
N20 C19 N18 141.0(3) . . ?
N15 C19 N18 105.2(2) . . ?
C19 N20 N21 100.9(2) . . ?
C22 N21 N20 113.3(3) . . ?
C22 N21 H21 123.4 . . ?
N20 N21 H21 123.4 . . ?
N25 C22 N21 128.8(3) . . ?
N25 C22 N15 127.1(3) . . ?
N21 C22 N15 104.0(3) . . ?
C17 N23 H23A 117(2) . . ?
C17 N23 H23B 117(3) . . ?
H23A N23 H23B 117(3) . . ?
N18 N24 H24A 106(3) . . ?
N18 N24 H24B 109(3) . . ?
H24A N24 H24B 119(4) . . ?
C22 N25 H25A 120(2) . . ?
C22 N25 H25B 116(3) . . ?
H25A N25 H25B 121(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
C5 N1 N2 C3 0.8(4) . . . . ?
N1 N2 C3 C4 -1.2(4) . . . . ?
N1 N2 C3 N6 -176.5(3) . . . . ?
N2 C3 C4 C5 1.1(4) . . . . ?
N6 C3 C4 C5 176.1(3) . . . . ?
N2 C3 C4 N9 -177.8(3) . . . . ?
N6 C3 C4 N9 -2.9(6) . . . . ?
N2 N1 C5 C4 -0.1(4) . . . . ?
N2 N1 C5 N12 179.9(3) . . . . ?
C3 C4 C5 N1 -0.6(4) . . . . ?
N9 C4 C5 N1 178.4(3) . . . . ?
C3 C4 C5 N12 179.4(3) . . . . ?
N9 C4 C5 N12 -1.7(6) . . . . ?
N2 C3 N6 O8 170.9(3) . . . . ?
C4 C3 N6 O8 -3.7(5) . . . . ?
N2 C3 N6 O7 -7.5(5) . . . . ?
C4 C3 N6 O7 177.9(3) . . . . ?
C5 C4 N9 O10 108.1(4) . . . . ?
C3 C4 N9 O10 -73.2(5) . . . . ?
C5 C4 N9 O11 -71.5(5) . . . . ?
C3 C4 N9 O11 107.1(4) . . . . ?
N1 C5 N12 O13 176.2(3) . . . . ?
C4 C5 N12 O13 -3.8(5) . . . . ?
N1 C5 N12 O14 -4.7(5) . . . . ?
C4 C5 N12 O14 175.3(3) . . . . ?
C22 N15 N16 C17 -176.7(4) . . . . ?
C19 N15 N16 C17 -1.1(4) . . . . ?
N15 N16 C17 N23 -176.6(3) . . . . ?
N15 N16 C17 N18 1.5(4) . . . . ?
N16 C17 N18 C19 -1.3(4) . . . . ?
N23 C17 N18 C19 176.9(3) . . . . ?
N16 C17 N18 N24 -172.8(3) . . . . ?
N23 C17 N18 N24 5.4(5) . . . . ?
C22 N15 C19 N20 -1.9(4) . . . . ?
N16 N15 C19 N20 -178.8(3) . . . . ?
C22 N15 C19 N18 177.4(3) . . . . ?
N16 N15 C19 N18 0.4(4) . . . . ?
C17 N18 C19 N20 179.3(5) . . . . ?
N24 N18 C19 N20 -9.9(7) . . . . ?
C17 N18 C19 N15 0.5(4) . . . . ?
N24 N18 C19 N15 171.2(3) . . . . ?
N15 C19 N20 N21 1.3(4) . . . . ?
N18 C19 N20 N21 -177.5(5) . . . . ?
C19 N20 N21 C22 -0.3(4) . . . . ?
N20 N21 C22 N25 176.2(4) . . . . ?
N20 N21 C22 N15 -0.8(4) . . . . ?
C19 N15 C22 N25 -175.5(4) . . . . ?
N16 N15 C22 N25 0.2(7) . . . . ?
C19 N15 C22 N21 1.5(4) . . . . ?
N16 N15 C22 N21 177.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21 H21 N1 0.88 2.01 2.816(4) 151.0 2_456
N23 H23A O11 0.98(4) 2.23(4) 3.206(4) 173(3) 2_465
N23 H23B O10 0.81(4) 2.34(4) 3.064(4) 150(4) 2_565
N24 H24A O10 0.88(4) 2.58(4) 3.173(4) 125(3) 1_545
N24 H24B O7 0.79(4) 2.58(4) 3.199(5) 137(4) 1_455
N25 H25A N2 0.89(4) 2.21(4) 2.996(4) 147(3) 2_556
N25 H25B N20 0.78(4) 2.36(4) 3.090(4) 156(4) 1_655

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.947
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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_shrv279
_database_code_depnum_ccdc_archive 'CCDC 1052627'
_audit_update_record             
;
2015-03-07 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            YP-034
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H6.78 N8, 0.78(Br)'
_chemical_formula_sum            'C3 H6.78 Br0.78 N8'
_chemical_formula_weight         217.52

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.330(4)
_cell_length_b                   6.711(4)
_cell_length_c                   9.034(6)
_cell_angle_alpha                95.533(8)
_cell_angle_beta                 90.022(7)
_cell_angle_gamma                90.076(8)
_cell_volume                     382.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.891
_exptl_crystal_F_000             216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    4.202
_shelx_estimated_absorpt_T_min   0.522
_shelx_estimated_absorpt_T_max   0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.522
_exptl_absorpt_correction_T_max  0.8910
_diffrn_ambient_temperature      150(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  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3383
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.049
_diffrn_reflns_theta_max         26.417
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             1555
_reflns_number_gt                1507
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;



_computing_data_collection       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'



_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0281P)²+0.1670P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1555
_refine_ls_number_parameters     116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0561
_refine_ls_wR_factor_gt          0.0557
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0.002
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.24999(3) 0.12036(3) 1.15344(2) 0.02076(10) Uani 0.7833(19) 1 d . . P .
.
N1 N 0.2500(2) 0.5928(2) 0.52601(16) 0.0190(3) Uani 1 1 d . . . . .
N2 N 0.2499(3) 0.3960(2) 0.56574(16) 0.0239(3) Uani 1 1 d . . . . .
C3 C 0.2501(3) 0.4288(2) 0.71325(19) 0.0209(4) Uani 1 1 d . . . . .
N4 N 0.2499(2) 0.6302(2) 0.76537(15) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.2500(2) 0.7330(2) 0.64297(18) 0.0183(3) Uani 1 1 d . . . . .
N6 N 0.2500(2) 0.9160(2) 0.60677(17) 0.0229(3) Uani 1 1 d . . . . .
N7 N 0.2499(2) 0.8826(2) 0.45125(16) 0.0222(3) Uani 1 1 d . . . . .
H7A H 0.2498 0.9798 0.3924 0.027 Uiso 0.7833(19) 1 calc R U P . .
C8 C 0.2501(3) 0.6884(3) 0.40093(19) 0.0207(4) Uani 1 1 d . . . . .
N9 N 0.2499(3) 0.2866(2) 0.80568(18) 0.0331(4) Uani 1 1 d . . . . .
H9A H 0.2496 0.1598 0.7702 0.040 Uiso 1 1 calc R U . . .
H9B H 0.2500 0.3192 0.9024 0.040 Uiso 1 1 calc R U . . .
N10 N 0.2498(3) 0.7053(2) 0.91528(16) 0.0222(3) Uani 1 1 d . . . . .
N11 N 0.2500(3) 0.6041(3) 0.26263(18) 0.0314(4) Uani 1 1 d . . . . .
H11A H 0.2498 0.6792 0.1880 0.038 Uiso 1 1 calc R U . . .
H11B H 0.2501 0.4728 0.2451 0.038 Uiso 1 1 calc R U . . .
H10B H 0.363(4) 0.780(4) 0.926(3) 0.038 Uiso 1 1 d . U . . .
H10C H 0.137(4) 0.783(4) 0.926(3) 0.038 Uiso 1 1 d . U . . .

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 0.02811(14) 0.01847(13) 0.01597(13) 0.00313(8) -0.00075(8) -0.00079(8)
N1 0.0275(7) 0.0137(7) 0.0164(7) 0.0052(5) -0.0007(5) -0.0007(5)
N2 0.0425(9) 0.0116(7) 0.0182(7) 0.0041(5) -0.0005(6) -0.0010(6)
C3 0.0284(8) 0.0140(8) 0.0205(8) 0.0033(6) -0.0005(6) -0.0009(6)
N4 0.0276(7) 0.0126(6) 0.0143(7) 0.0020(5) -0.0006(5) -0.0004(5)
C5 0.0211(8) 0.0131(7) 0.0209(8) 0.0031(6) -0.0007(6) -0.0011(6)
N6 0.0324(8) 0.0142(7) 0.0226(7) 0.0056(6) -0.0010(6) -0.0011(5)
N7 0.0270(7) 0.0188(7) 0.0225(8) 0.0104(6) -0.0001(5) -0.0012(5)
C8 0.0223(8) 0.0209(8) 0.0203(8) 0.0086(7) -0.0008(6) -0.0003(6)
N9 0.0675(11) 0.0128(7) 0.0198(8) 0.0053(6) -0.0007(7) -0.0004(7)
N10 0.0310(8) 0.0196(7) 0.0154(7) -0.0009(6) -0.0005(5) -0.0006(6)
N11 0.0509(10) 0.0277(8) 0.0168(7) 0.0077(6) -0.0006(6) -0.0008(7)

_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
N1 C5 1.345(2) . ?
N1 C8 1.352(2) . ?
N1 N2 1.402(2) . ?
N2 C3 1.330(2) . ?
C3 N9 1.327(2) . ?
C3 N4 1.388(2) . ?
N4 C5 1.359(2) . ?
N4 N10 1.399(2) . ?
C5 N6 1.301(2) . ?
N6 N7 1.401(2) . ?
N7 C8 1.338(2) . ?
N7 H7A 0.8800 . ?
C8 N11 1.321(3) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
N10 H10B 0.87(3) . ?
N10 H10C 0.88(3) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?

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 N1 C8 107.71(14) . . ?
C5 N1 N2 113.81(14) . . ?
C8 N1 N2 138.48(14) . . ?
C3 N2 N1 100.79(13) . . ?
N9 C3 N2 124.80(16) . . ?
N9 C3 N4 121.49(16) . . ?
N2 C3 N4 113.71(14) . . ?
C5 N4 C3 106.16(14) . . ?
C5 N4 N10 128.60(14) . . ?
C3 N4 N10 125.25(14) . . ?
N6 C5 N1 114.09(15) . . ?
N6 C5 N4 140.39(15) . . ?
N1 C5 N4 105.53(14) . . ?
C5 N6 N7 100.85(13) . . ?
C8 N7 N6 113.40(13) . . ?
C8 N7 H7A 123.3 . . ?
N6 N7 H7A 123.3 . . ?
N11 C8 N7 129.46(15) . . ?
N11 C8 N1 126.58(16) . . ?
N7 C8 N1 103.95(15) . . ?
C3 N9 H9A 120.0 . . ?
C3 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
N4 N10 H10B 105.1(16) . . ?
N4 N10 H10C 105.1(16) . . ?
H10B N10 H10C 109(2) . . ?
C8 N11 H11A 120.0 . . ?
C8 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?

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
C5 N1 N2 C3 -0.04(18) . . . . ?
C8 N1 N2 C3 179.9(2) . . . . ?
N1 N2 C3 N9 179.93(18) . . . . ?
N1 N2 C3 N4 0.07(19) . . . . ?
N9 C3 N4 C5 -179.95(17) . . . . ?
N2 C3 N4 C5 -0.1(2) . . . . ?
N9 C3 N4 N10 0.1(3) . . . . ?
N2 C3 N4 N10 179.93(15) . . . . ?
C8 N1 C5 N6 0.05(19) . . . . ?
N2 N1 C5 N6 -179.98(14) . . . . ?
C8 N1 C5 N4 -179.99(14) . . . . ?
N2 N1 C5 N4 -0.01(17) . . . . ?
C3 N4 C5 N6 -180.0(2) . . . . ?
N10 N4 C5 N6 0.0(3) . . . . ?
C3 N4 C5 N1 0.05(16) . . . . ?
N10 N4 C5 N1 -179.96(16) . . . . ?
N1 C5 N6 N7 0.00(18) . . . . ?
N4 C5 N6 N7 -180.0(2) . . . . ?
C5 N6 N7 C8 -0.04(18) . . . . ?
N6 N7 C8 N11 179.96(17) . . . . ?
N6 N7 C8 N1 0.07(18) . . . . ?
C5 N1 C8 N11 -179.96(17) . . . . ?
N2 N1 C8 N11 0.1(3) . . . . ?
C5 N1 C8 N7 -0.07(17) . . . . ?
N2 N1 C8 N7 179.97(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N7 H7A Br1 0.88 2.44 3.258(2) 155.1 1_564
N9 H9A N6 0.88 2.10 2.925(3) 156.7 1_545
N9 H9B Br1 0.88 2.74 3.434(2) 136.7 .
N10 H10B Br1 0.87(3) 2.66(3) 3.451(3) 152(2) 2_667
N10 H10C Br1 0.88(3) 2.65(3) 3.451(2) 151(2) 2_567
N11 H11A N10 0.88 2.49 3.274(3) 149.3 1_554
N11 H11B Br1 0.88 2.43 3.301(3) 170.5 1_554



_refine_diff_density_max         0.387
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.063




# start Validation Reply Form
_vrf_PLAT015_shrv279             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ...      Please Do ! 
RESPONSE: It is our policy to routinley not supply the HKL file unless 
specifically required.
;
_vrf_PLAT113_shrv279             
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New Space group.      P21/m Check 
RESPONSE: Investigated higher symmetry, refinements were unstable
;



