# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1465378'
_audit_update_record             
;
2016-04-13 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N2, 2(C4 H4 Br N O2)'
_chemical_formula_sum            'C18 H16 Br2 N4 O4'
_chemical_formula_weight         512.17

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   24.0130(10)
_cell_length_b                   4.8573(2)
_cell_length_c                   18.3684(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.975(4)
_cell_angle_gamma                90
_cell_volume                     2000.49(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295
_cell_measurement_reflns_used    4867
_cell_measurement_theta_min      4
_cell_measurement_theta_max      36

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    4.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.19176
_exptl_absorpt_correction_T_max  0.70498
_exptl_absorpt_process_details   'N.W. Alcock (1970). Cryst. Computing, p271'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16541
_diffrn_reflns_av_unetI/netI     0.1306
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.210
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             4177
_reflns_number_gt                1958
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0197P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4177
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0522
_refine_ls_wR_factor_gt          0.0482
_refine_ls_goodness_of_fit_ref   0.705
_refine_ls_restrained_S_all      0.705
_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_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
C1 C 0.26275(18) 0.0285(7) 0.1555(2) 0.0523(9) Uani 1 1 d . . . . .
C2 C 0.24537(16) -0.1775(7) 0.20421(19) 0.0678(11) Uani 1 1 d . . . . .
H2A H 0.2233 -0.3282 0.1721 0.081 Uiso 1 1 calc R U . . .
H2B H 0.2207 -0.0920 0.2296 0.081 Uiso 1 1 calc R U . . .
C3 C 0.30292(16) -0.2808(7) 0.26402(19) 0.0661(11) Uani 1 1 d . . . . .
H3A H 0.3056 -0.2300 0.3162 0.079 Uiso 1 1 calc R U . . .
H3B H 0.3056 -0.4796 0.2613 0.079 Uiso 1 1 calc R U . . .
C4 C 0.35163(18) -0.1443(7) 0.24355(18) 0.0501(9) Uani 1 1 d . . . . .
C5 C 0.1438(2) 0.5433(7) -0.10119(18) 0.0533(10) Uani 1 1 d . . . . .
C6 C 0.18820(15) 0.7000(7) -0.03483(17) 0.0588(10) Uani 1 1 d . . . . .
H6A H 0.1863 0.6411 0.0147 0.071 Uiso 1 1 calc R U . . .
H6B H 0.1803 0.8962 -0.0407 0.071 Uiso 1 1 calc R U . . .
C7 C 0.24862(16) 0.6353(7) -0.03879(18) 0.0608(10) Uani 1 1 d . . . . .
H7A H 0.2660 0.7984 -0.0525 0.073 Uiso 1 1 calc R U . . .
H7B H 0.2755 0.5670 0.0110 0.073 Uiso 1 1 calc R U . . .
C8 C 0.23744(18) 0.4180(7) -0.10087(19) 0.0513(9) Uani 1 1 d . . . . .
C9 C 0.40966(15) 0.5628(7) 0.0056(2) 0.0560(10) Uani 1 1 d . . . . .
H9 H 0.3787 0.4548 -0.0267 0.067 Uiso 1 1 calc R U . . .
C10 C 0.43796(14) 0.7410(7) -0.02903(17) 0.0515(9) Uani 1 1 d . . . . .
H10 H 0.4259 0.7499 -0.0831 0.062 Uiso 1 1 calc R U . . .
C11 C 0.48422(13) 0.9055(6) 0.01720(17) 0.0396(8) Uani 1 1 d . . . . .
C12 C 0.49917(15) 0.8757(7) 0.09681(19) 0.0562(10) Uani 1 1 d . . . . .
H12 H 0.5300 0.9801 0.1308 0.067 Uiso 1 1 calc R U . . .
C13 C 0.46871(16) 0.6925(7) 0.12638(19) 0.0585(10) Uani 1 1 d . . . . .
H13 H 0.4800 0.6772 0.1802 0.070 Uiso 1 1 calc R U . . .
C14 C 0.04272(17) -0.3033(7) -0.33042(18) 0.0600(10) Uani 1 1 d . . . . .
H14 H 0.0363 -0.3289 -0.2839 0.072 Uiso 1 1 calc R U . . .
C15 C 0.00945(14) -0.4561(7) -0.39441(18) 0.0535(10) Uani 1 1 d . . . . .
H15 H -0.0183 -0.5829 -0.3903 0.064 Uiso 1 1 calc R U . . .
C16 C 0.01741(14) -0.4204(6) -0.46423(15) 0.0384(8) Uani 1 1 d . . . . .
C17 C 0.05865(14) -0.2270(7) -0.46601(17) 0.0530(9) Uani 1 1 d . . . . .
H17 H 0.0649 -0.1920 -0.5123 0.064 Uiso 1 1 calc R U . . .
C18 C 0.09068(15) -0.0853(7) -0.3993(2) 0.0578(10) Uani 1 1 d . . . . .
H18 H 0.1188 0.0425 -0.4016 0.069 Uiso 1 1 calc R U . . .
N1 N 0.32416(13) 0.0270(5) 0.17980(14) 0.0461(7) Uani 1 1 d . . . . .
N2 N 0.17635(12) 0.3849(5) -0.13397(13) 0.0463(7) Uani 1 1 d . . . . .
N3 N 0.42425(12) 0.5378(5) 0.08197(17) 0.0524(7) Uani 1 1 d . . . . .
N4 N 0.08325(12) -0.1227(6) -0.33191(14) 0.0510(7) Uani 1 1 d . . . . .
O1 O 0.23045(11) 0.1734(5) 0.10436(13) 0.0712(7) Uani 1 1 d . . . . .
O2 O 0.40477(12) -0.1710(5) 0.27560(13) 0.0709(8) Uani 1 1 d . . . . .
O3 O 0.08985(12) 0.5501(5) -0.12302(13) 0.0731(8) Uani 1 1 d . . . . .
O4 O 0.27328(11) 0.2958(5) -0.12088(14) 0.0728(7) Uani 1 1 d . . . . .
Br1 Br 0.36938(2) 0.25290(7) 0.13572(2) 0.05303(11) Uani 1 1 d . . . . .
Br2 Br 0.13689(2) 0.14852(7) -0.22143(2) 0.05189(12) Uani 1 1 d . . . . .


_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
C1 O1 1.208(4) . ?
C1 N1 1.379(4) . ?
C1 C2 1.497(4) . ?
C2 C3 1.511(4) . ?
C3 C4 1.505(4) . ?
C4 O2 1.206(4) . ?
C4 N1 1.395(4) . ?
C5 O3 1.211(4) . ?
C5 N2 1.380(4) . ?
C5 C6 1.508(4) . ?
C6 C7 1.511(4) . ?
C7 C8 1.506(4) . ?
C8 O4 1.206(4) . ?
C8 N2 1.382(4) . ?
C9 N3 1.324(4) . ?
C9 C10 1.387(4) . ?
C10 C11 1.385(4) . ?
C11 C12 1.383(4) . ?
C11 C11 1.470(5) 3_675 ?
C12 C13 1.380(4) . ?
C13 N3 1.321(4) . ?
C14 N4 1.318(4) . ?
C14 C15 1.378(4) . ?
C15 C16 1.373(4) . ?
C16 C17 1.374(4) . ?
C16 C16 1.496(5) 3_544 ?
C17 C18 1.376(4) . ?
C18 N4 1.324(4) . ?
N1 Br1 1.915(3) . ?
N2 Br2 1.925(2) . ?

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
O1 C1 N1 124.7(3) . . ?
O1 C1 C2 128.0(4) . . ?
N1 C1 C2 107.3(3) . . ?
C1 C2 C3 106.2(3) . . ?
C4 C3 C2 105.2(3) . . ?
O2 C4 N1 125.0(3) . . ?
O2 C4 C3 127.7(3) . . ?
N1 C4 C3 107.2(3) . . ?
O3 C5 N2 125.2(3) . . ?
O3 C5 C6 128.1(3) . . ?
N2 C5 C6 106.7(3) . . ?
C5 C6 C7 105.7(3) . . ?
C8 C7 C6 105.6(3) . . ?
O4 C8 N2 124.7(3) . . ?
O4 C8 C7 128.5(3) . . ?
N2 C8 C7 106.8(3) . . ?
N3 C9 C10 123.7(3) . . ?
C11 C10 C9 119.7(3) . . ?
C12 C11 C10 115.8(3) . . ?
C12 C11 C11 122.8(4) . 3_675 ?
C10 C11 C11 121.4(3) . 3_675 ?
C13 C12 C11 120.7(3) . . ?
N3 C13 C12 123.3(3) . . ?
N4 C14 C15 123.2(3) . . ?
C16 C15 C14 119.8(3) . . ?
C15 C16 C17 116.8(3) . . ?
C15 C16 C16 122.3(4) . 3_544 ?
C17 C16 C16 120.9(4) . 3_544 ?
C16 C17 C18 119.9(3) . . ?
N4 C18 C17 123.0(3) . . ?
C1 N1 C4 113.8(3) . . ?
C1 N1 Br1 124.2(2) . . ?
C4 N1 Br1 121.8(2) . . ?
C5 N2 C8 114.9(3) . . ?
C5 N2 Br2 120.7(2) . . ?
C8 N2 Br2 124.4(2) . . ?
C13 N3 C9 116.8(3) . . ?
C14 N4 C18 117.3(3) . . ?

_refine_diff_density_max         0.850
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1465379'
_audit_update_record             
;
2016-04-13 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N2, C4 H4 Br N O2'
_chemical_formula_sum            'C14 H12 Br N3 O2'
_chemical_formula_weight         334.18

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.7340(6)
_cell_length_b                   7.3700(3)
_cell_length_c                   12.2070(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.213(4)
_cell_angle_gamma                90
_cell_volume                     1352.12(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    295
_cell_measurement_reflns_used    4355
_cell_measurement_theta_min      4
_cell_measurement_theta_max      35

_exptl_crystal_description       needle
_exptl_crystal_colour            colourles
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    3.045
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.35039
_exptl_absorpt_correction_T_max  0.84733
_exptl_absorpt_process_details   'N.W. Alcock (1970). Cryst. Computing, p271'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13225
_diffrn_reflns_av_unetI/netI     0.0704
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.873
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2946
_reflns_number_gt                1905
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0253P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2946
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0565
_refine_ls_wR_factor_gt          0.0535
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_restrained_S_all      0.833
_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_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
C1 C 0.71685(18) 0.5683(3) 0.3847(2) 0.0367(6) Uani 1 1 d . . . . .
C2 C 0.62594(18) 0.5548(4) 0.2983(2) 0.0456(7) Uani 1 1 d . . . . .
H2A H 0.6153 0.4328 0.2676 0.055 Uiso 1 1 calc R U . . .
H2B H 0.6207 0.6388 0.2355 0.055 Uiso 1 1 calc R U . . .
C3 C 0.56002(17) 0.6030(3) 0.3632(2) 0.0455(7) Uani 1 1 d . . . . .
H3A H 0.5266 0.7109 0.3309 0.055 Uiso 1 1 calc R U . . .
H3B H 0.5186 0.5040 0.3595 0.055 Uiso 1 1 calc R U . . .
C4 C 0.61492(16) 0.6365(3) 0.4851(2) 0.0367(6) Uani 1 1 d . . . . .
C5 C 0.62640(18) 0.1264(3) 0.4870(2) 0.0505(7) Uani 1 1 d . . . . .
H5 H 0.5809 0.1470 0.5198 0.061 Uiso 1 1 calc R U . . .
C6 C 0.71303(17) 0.1512(3) 0.5548(2) 0.0424(6) Uani 1 1 d . . . . .
H6 H 0.7246 0.1858 0.6311 0.051 Uiso 1 1 calc R U . . .
C7 C 0.78206(15) 0.1245(3) 0.50918(19) 0.0318(6) Uani 1 1 d . . . . .
C8 C 0.75951(17) 0.0721(3) 0.3949(2) 0.0394(6) Uani 1 1 d . . . . .
H8 H 0.8035 0.0521 0.3595 0.047 Uiso 1 1 calc R U . . .
C9 C 0.67104(19) 0.0504(4) 0.3345(2) 0.0485(7) Uani 1 1 d . . . . .
H9 H 0.6574 0.0158 0.2580 0.058 Uiso 1 1 calc R U . . .
C10 C 0.99245(18) 0.1061(3) 0.7539(2) 0.0446(7) Uani 1 1 d . . . . .
H10 H 1.0094 0.0733 0.8309 0.053 Uiso 1 1 calc R U . . .
C11 C 0.90341(16) 0.0961(3) 0.69437(19) 0.0383(7) Uani 1 1 d . . . . .
H11 H 0.8620 0.0585 0.7304 0.046 Uiso 1 1 calc R U . . .
C12 C 0.87692(15) 0.1436(3) 0.57878(19) 0.0316(5) Uani 1 1 d . . . . .
C13 C 0.94228(17) 0.2023(3) 0.5331(2) 0.0409(7) Uani 1 1 d . . . . .
H13 H 0.9273 0.2382 0.4568 0.049 Uiso 1 1 calc R U . . .
C14 C 1.02992(18) 0.2082(3) 0.6003(2) 0.0442(7) Uani 1 1 d . . . . .
H14 H 1.0728 0.2483 0.5673 0.053 Uiso 1 1 calc R U . . .
N1 N 0.70371(13) 0.6184(2) 0.48805(15) 0.0333(5) Uani 1 1 d . . . . .
N2 N 0.60409(16) 0.0753(3) 0.3781(2) 0.0526(6) Uani 1 1 d . . . . .
N3 N 1.05580(14) 0.1592(3) 0.70973(18) 0.0412(5) Uani 1 1 d . . . . .
O1 O 0.59037(12) 0.6717(3) 0.56639(15) 0.0556(5) Uani 1 1 d . . . . .
O2 O 0.78758(13) 0.5415(3) 0.37007(16) 0.0564(5) Uani 1 1 d . . . . .
Br1 Br 0.79845(2) 0.64395(3) 0.62247(2) 0.03830(9) Uani 1 1 d . . . . .


_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
C1 O2 1.195(3) . ?
C1 N1 1.388(3) . ?
C1 C2 1.508(3) . ?
C2 C3 1.522(4) . ?
C3 C4 1.504(3) . ?
C4 O1 1.195(3) . ?
C4 N1 1.393(3) . ?
C5 N2 1.325(3) . ?
C5 C6 1.382(3) . ?
C6 C7 1.374(3) . ?
C7 C8 1.389(3) . ?
C7 C12 1.490(3) . ?
C8 C9 1.378(3) . ?
C9 N2 1.326(3) . ?
C10 N3 1.325(3) . ?
C10 C11 1.376(3) . ?
C11 C12 1.393(3) . ?
C12 C13 1.376(3) . ?
C13 C14 1.381(3) . ?
C14 N3 1.326(3) . ?
N1 Br1 1.8714(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
O2 C1 N1 125.1(2) . . ?
O2 C1 C2 128.1(3) . . ?
N1 C1 C2 106.7(2) . . ?
C1 C2 C3 105.80(19) . . ?
C4 C3 C2 105.9(2) . . ?
O1 C4 N1 124.6(2) . . ?
O1 C4 C3 128.7(2) . . ?
N1 C4 C3 106.7(2) . . ?
N2 C5 C6 124.1(3) . . ?
C7 C6 C5 119.7(2) . . ?
C6 C7 C8 116.7(2) . . ?
C6 C7 C12 122.3(2) . . ?
C8 C7 C12 121.0(2) . . ?
C9 C8 C7 119.1(3) . . ?
N2 C9 C8 124.5(3) . . ?
N3 C10 C11 124.9(2) . . ?
C10 C11 C12 118.3(2) . . ?
C13 C12 C11 117.0(2) . . ?
C13 C12 C7 122.8(2) . . ?
C11 C12 C7 120.2(2) . . ?
C12 C13 C14 120.3(2) . . ?
N3 C14 C13 123.0(3) . . ?
C1 N1 C4 114.85(19) . . ?
C1 N1 Br1 121.98(17) . . ?
C4 N1 Br1 123.04(16) . . ?
C5 N2 C9 115.8(2) . . ?
C10 N3 C14 116.5(2) . . ?

_refine_diff_density_max         0.307
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.075

_shelxl_version_number           2013-4

