# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_11dotH2O
_database_code_depnum_ccdc_archive 'CCDC 1443587'
_audit_update_record             
;
2015-12-21 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;
_audit_creation_date             2015-12-21
_audit_creation_method           'by CrystalStructure 4.1'



_chemical_formula_sum            'C4 H6 Br2 N2 O2'
_chemical_formula_moiety         'C4 H6 Br2 N2 O2'
_chemical_formula_weight         273.91
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,1/2-Y,1/2+Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2+X,-1/2-Y,-Z
7 -X,-1/2+Y,-1/2-Z
8 -1/2+X,+Y,-1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   13.4208(15)
_cell_length_b                   6.0747(7)
_cell_length_c                   19.193(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1564.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4873
_cell_measurement_theta_min      1.85
_cell_measurement_theta_max      28.56
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    2.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040.00
_exptl_absorpt_coefficient_mu    10.334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.191
_exptl_absorpt_correction_T_max  0.437

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            9244
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_min         2.122
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1430
_reflns_number_gt                1253
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0785
_refine_ls_wR_factor_gt          0.0756
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1430
_refine_ls_number_parameters     107
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0413P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.65
_refine_diff_density_min         -0.99
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.10631(3) 1.17713(7) 0.89300(2) 0.01270(16) Uani 1 1 d . . . . .
Br2 Br 0.16109(3) 0.25016(7) 0.98332(2) 0.01811(17) Uani 1 1 d . . . . .
O5 O 0.1737(2) 0.1852(5) 0.82482(15) 0.0174(6) Uani 1 1 d D . . . .
O10 O 0.1825(2) 0.1076(5) 0.69473(15) 0.0219(7) Uani 1 1 d D . . . .
N1 N 0.0559(2) 0.7171(6) 0.80565(17) 0.0154(8) Uani 1 1 d . . . . .
N2 N 0.0486(3) 0.7657(5) 0.87363(19) 0.0142(8) Uani 1 1 d D . . . .
C3 C 0.0805(3) 0.6397(7) 0.9252(2) 0.0130(9) Uani 1 1 d . . . . .
H3 H 0.0734 0.6870 0.9721 0.016 Uiso 1 1 calc R U . . .
C4 C 0.1239(3) 0.4409(7) 0.91079(19) 0.0120(8) Uani 1 1 d . . . . .
C5 C 0.1337(3) 0.3776(6) 0.8417(2) 0.0119(8) Uani 1 1 d . . . . .
C6 C 0.0981(2) 0.5267(7) 0.7910(2) 0.0135(9) Uani 1 1 d . . . . .
H6 H 0.1050 0.4872 0.7434 0.016 Uiso 1 1 calc R U . . .
H2N H 0.016(3) 0.907(4) 0.882(3) 0.048(16) Uiso 1 1 d D . . . .
H5O H 0.179(5) 0.158(14) 0.7747(9) 0.11(3) Uiso 1 1 d D . . . .
H10A H 0.246(3) 0.132(12) 0.672(3) 0.10(2) Uiso 1 1 d D . . . .
H10B H 0.152(5) -0.023(7) 0.674(4) 0.12(3) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Br2 C4 1.879(4) . ?
O5 C5 1.327(5) . ?
O5 H5O 0.980(5) . ?
O10 H10A 0.979(5) . ?
O10 H10B 0.980(5) . ?
N1 C6 1.318(5) . ?
N1 N2 1.342(5) . ?
N2 C3 1.323(5) . ?
N2 H2N 0.978(5) . ?
C3 C4 1.369(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(5) . ?
C5 C6 1.412(6) . ?
C6 H6 0.9500 . ?

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 O5 H5O 115(5) . . ?
H10A O10 H10B 107(6) . . ?
C6 N1 N2 115.6(3) . . ?
C3 N2 N1 125.2(3) . . ?
C3 N2 H2N 122(3) . . ?
N1 N2 H2N 113(3) . . ?
N2 C3 C4 119.9(4) . . ?
N2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 118.5(4) . . ?
C3 C4 Br2 120.5(3) . . ?
C5 C4 Br2 120.8(3) . . ?
O5 C5 C4 121.1(3) . . ?
O5 C5 C6 122.3(4) . . ?
C4 C5 C6 116.7(4) . . ?
N1 C6 C5 124.1(4) . . ?
N1 C6 H6 117.9 . . ?
C5 C6 H6 117.9 . . ?

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
C6 N1 N2 C3 0.5(5) . . . . ?
N1 N2 C3 C4 -1.0(6) . . . . ?
N2 C3 C4 C5 0.4(6) . . . . ?
N2 C3 C4 Br2 -175.4(3) . . . . ?
C3 C4 C5 O5 -178.9(3) . . . . ?
Br2 C4 C5 O5 -3.1(5) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
Br2 C4 C5 C6 176.2(3) . . . . ?
N2 N1 C6 C5 0.4(5) . . . . ?
O5 C5 C6 N1 178.5(3) . . . . ?
C4 C5 C6 N1 -0.9(6) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1443588'
_audit_update_record             
;
2015-12-21 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;
_audit_creation_date             2015-12-21
_audit_creation_method           'by CrystalStructure 4.1'


_chemical_formula_sum            'C12 H16 Br2 N2 O5'
_chemical_formula_moiety         'C12 H16 Br2 N2 O5'
_chemical_formula_weight         428.08
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.676(5)
_cell_length_b                   9.708(4)
_cell_length_c                   14.448(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.350(11)
_cell_angle_gamma                90.0000
_cell_volume                     1636.3(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4520
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      28.65
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848.00
_exptl_absorpt_coefficient_mu    4.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.193
_exptl_absorpt_correction_T_max  0.861

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            10384
_diffrn_reflns_av_R_equivalents  0.1218
_diffrn_reflns_theta_max         25.286
_diffrn_reflns_theta_min         2.528
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2944
_reflns_number_gt                2091
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1373
_refine_ls_R_factor_gt           0.1080
_refine_ls_wR_factor_ref         0.2888
_refine_ls_wR_factor_gt          0.2634
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2944
_refine_ls_number_parameters     194
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1528P)²+3.0075P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         2.32
_refine_diff_density_min         -1.50
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br3 Br 0.72655(10) -0.02558(12) 0.86727(8) 0.0433(5) Uani 1 1 d . . . . .
Br5 Br 1.06386(11) 0.14167(12) 0.69306(8) 0.0444(5) Uani 1 1 d . . . . .
O4 O 1.0223(7) -0.0118(7) 0.8778(5) 0.0414(19) Uani 1 1 d . . . . .
O7 O 0.6152(7) 0.3526(7) 0.8695(5) 0.0387(19) Uani 1 1 d . . . . .
O8 O 0.6919(6) 0.4344(8) 0.7403(5) 0.0369(17) Uani 1 1 d . . . . .
O12 O 0.7838(8) 0.2464(8) 1.0759(5) 0.046(2) Uani 1 1 d . . . . .
O13 O 0.8022(7) 0.4427(8) 0.9915(5) 0.0389(18) Uani 1 1 d . . . . .
N1 N 0.8012(8) 0.3065(9) 0.8379(5) 0.034(2) Uani 1 1 d . . . . .
N2 N 0.8159(8) 0.2392(8) 0.9216(6) 0.033(2) Uani 1 1 d . . . . .
C3 C 0.8493(9) 0.0978(10) 0.9217(7) 0.034(2) Uani 1 1 d . . . . .
H3 H 0.8700 0.0680 0.9865 0.041 Uiso 1 1 calc R U . . .
C4 C 0.9527(10) 0.0778(11) 0.8606(7) 0.036(3) Uani 1 1 d . . . . .
C5 C 0.9558(10) 0.1743(11) 0.7828(7) 0.038(3) Uani 1 1 d . . . . .
C6 C 0.8787(10) 0.2739(12) 0.7718(8) 0.043(3) Uani 1 1 d . . . . .
H6 H 0.8767 0.3251 0.7158 0.051 Uiso 1 1 calc R U . . .
C7 C 0.6901(11) 0.3632(10) 0.8165(7) 0.034(3) Uani 1 1 d . . . . .
C9 C 0.5882(10) 0.5144(11) 0.7136(8) 0.039(3) Uani 1 1 d . . . . .
H9 H 0.5185 0.4584 0.7255 0.047 Uiso 1 1 calc R U . . .
C10 C 0.5868(12) 0.6435(11) 0.7701(9) 0.048(3) Uani 1 1 d . . . . .
H10A H 0.6577 0.6952 0.7617 0.057 Uiso 1 1 calc R U . . .
H10B H 0.5808 0.6198 0.8356 0.057 Uiso 1 1 calc R U . . .
H10C H 0.5209 0.7001 0.7499 0.057 Uiso 1 1 calc R U . . .
C11 C 0.5971(12) 0.5361(14) 0.6110(8) 0.050(3) Uani 1 1 d . . . . .
H11A H 0.5823 0.4490 0.5785 0.060 Uiso 1 1 calc R U . . .
H11B H 0.6742 0.5689 0.5981 0.060 Uiso 1 1 calc R U . . .
H11C H 0.5404 0.6048 0.5897 0.060 Uiso 1 1 calc R U . . .
C12 C 0.7966(11) 0.3086(12) 1.0064(8) 0.043(3) Uani 1 1 d . . . . .
C14 C 0.7791(11) 0.5302(10) 1.0735(8) 0.040(3) Uani 1 1 d . . . . .
H14 H 0.8125 0.4863 1.1311 0.049 Uiso 1 1 calc R U . . .
C15 C 0.6510(11) 0.5424(12) 1.0794(9) 0.048(3) Uani 1 1 d . . . . .
H15A H 0.6172 0.4502 1.0824 0.058 Uiso 1 1 calc R U . . .
H15B H 0.6194 0.5906 1.0245 0.058 Uiso 1 1 calc R U . . .
H15C H 0.6330 0.5944 1.1351 0.058 Uiso 1 1 calc R U . . .
C16 C 0.8377(11) 0.6650(11) 1.0567(9) 0.048(3) Uani 1 1 d . . . . .
H16A H 0.7940 0.7167 1.0089 0.057 Uiso 1 1 calc R U . . .
H16B H 0.9153 0.6477 1.0361 0.057 Uiso 1 1 calc R U . . .
H16C H 0.8419 0.7185 1.1143 0.057 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Br3 C3 2.004(10) . ?
Br5 C5 1.873(11) . ?
O4 C4 1.209(13) . ?
O7 C7 1.191(14) . ?
O8 C7 1.301(12) . ?
O8 C9 1.476(13) . ?
O12 C12 1.186(14) . ?
O13 C12 1.321(13) . ?
O13 C14 1.491(12) . ?
N1 N2 1.379(11) . ?
N1 C6 1.379(14) . ?
N1 C7 1.431(14) . ?
N2 C12 1.424(14) . ?
N2 C3 1.427(13) . ?
C3 C4 1.538(15) . ?
C3 H3 1.0000 . ?
C4 C5 1.465(16) . ?
C5 C6 1.326(16) . ?
C6 H6 0.9500 . ?
C9 C10 1.496(15) . ?
C9 C11 1.505(16) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C14 C16 1.501(16) . ?
C14 C15 1.506(18) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C7 O8 C9 117.3(9) . . ?
C12 O13 C14 114.9(9) . . ?
N2 N1 C6 115.9(9) . . ?
N2 N1 C7 116.8(8) . . ?
C6 N1 C7 123.6(9) . . ?
N1 N2 C12 120.8(8) . . ?
N1 N2 C3 118.8(8) . . ?
C12 N2 C3 120.4(8) . . ?
N2 C3 C4 110.0(9) . . ?
N2 C3 Br3 112.6(7) . . ?
C4 C3 Br3 105.3(7) . . ?
N2 C3 H3 109.6 . . ?
C4 C3 H3 109.6 . . ?
Br3 C3 H3 109.6 . . ?
O4 C4 C5 125.5(10) . . ?
O4 C4 C3 120.6(10) . . ?
C5 C4 C3 113.9(9) . . ?
C6 C5 C4 121.3(11) . . ?
C6 C5 Br5 120.9(9) . . ?
C4 C5 Br5 117.5(8) . . ?
C5 C6 N1 123.1(11) . . ?
C5 C6 H6 118.4 . . ?
N1 C6 H6 118.4 . . ?
O7 C7 O8 128.9(11) . . ?
O7 C7 N1 120.7(9) . . ?
O8 C7 N1 110.0(10) . . ?
O8 C9 C10 109.0(10) . . ?
O8 C9 C11 104.0(9) . . ?
C10 C9 C11 115.0(10) . . ?
O8 C9 H9 109.5 . . ?
C10 C9 H9 109.5 . . ?
C11 C9 H9 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O12 C12 O13 130.4(11) . . ?
O12 C12 N2 121.2(10) . . ?
O13 C12 N2 108.4(9) . . ?
O13 C14 C16 105.7(9) . . ?
O13 C14 C15 107.6(9) . . ?
C16 C14 C15 113.6(9) . . ?
O13 C14 H14 109.9 . . ?
C16 C14 H14 109.9 . . ?
C15 C14 H14 109.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C6 N1 N2 C12 142.4(11) . . . . ?
C7 N1 N2 C12 -58.5(13) . . . . ?
C6 N1 N2 C3 -38.5(13) . . . . ?
C7 N1 N2 C3 120.6(10) . . . . ?
N1 N2 C3 C4 49.4(12) . . . . ?
C12 N2 C3 C4 -131.5(10) . . . . ?
N1 N2 C3 Br3 -67.7(11) . . . . ?
C12 N2 C3 Br3 111.4(9) . . . . ?
N2 C3 C4 O4 149.8(10) . . . . ?
Br3 C3 C4 O4 -88.6(11) . . . . ?
N2 C3 C4 C5 -30.6(12) . . . . ?
Br3 C3 C4 C5 90.9(9) . . . . ?
O4 C4 C5 C6 -176.6(11) . . . . ?
C3 C4 C5 C6 3.8(16) . . . . ?
O4 C4 C5 Br5 9.2(16) . . . . ?
C3 C4 C5 Br5 -170.3(7) . . . . ?
C4 C5 C6 N1 9.5(19) . . . . ?
Br5 C5 C6 N1 -176.6(8) . . . . ?
N2 N1 C6 C5 6.7(17) . . . . ?
C7 N1 C6 C5 -150.8(11) . . . . ?
C9 O8 C7 O7 0.1(16) . . . . ?
C9 O8 C7 N1 -172.7(8) . . . . ?
N2 N1 C7 O7 0.4(14) . . . . ?
C6 N1 C7 O7 157.7(11) . . . . ?
N2 N1 C7 O8 174.0(8) . . . . ?
C6 N1 C7 O8 -28.7(14) . . . . ?
C7 O8 C9 C10 78.5(12) . . . . ?
C7 O8 C9 C11 -158.4(9) . . . . ?
C14 O13 C12 O12 -5.8(18) . . . . ?
C14 O13 C12 N2 177.7(9) . . . . ?
N1 N2 C12 O12 163.0(11) . . . . ?
C3 N2 C12 O12 -16.0(17) . . . . ?
N1 N2 C12 O13 -20.1(14) . . . . ?
C3 N2 C12 O13 160.9(10) . . . . ?
C12 O13 C14 C16 155.9(10) . . . . ?
C12 O13 C14 C15 -82.4(11) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


