# Electronic Supplementary Material (ESI) for Faraday Discussions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_n2787
_database_code_depnum_ccdc_archive 'CCDC 1532254'
_audit_update_record             
;
2017-02-11 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;
_audit_creation_date             2013-05-30
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C Br3 F, C10 H16 N2'
_chemical_formula_sum            'C11 H16 Br3 F N2'
_chemical_formula_weight         434.99
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.6232(2)
_cell_length_b                   22.4248(7)
_cell_length_c                   5.8554(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.3206(16)
_cell_angle_gamma                90
_cell_volume                     737.12(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5251
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.61
_cell_measurement_theta_min      3.94
_exptl_absorpt_coefficient_mu    10.105
_exptl_absorpt_correction_T_max  0.7525
_exptl_absorpt_correction_T_min  0.5439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0800 before and 0.0358 after correction.
The Ratio of minimum to maximum transmission is 0.7228.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.960
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.014
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7249
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.788
_diffrn_reflns_theta_min         3.942
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   microsource
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1206
_reflns_number_total             1264
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0208
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0322P)²+0.6773P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0540
_refine_ls_wR_factor_ref         0.0554
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Br2(0.25) Br2A(0.25) F1(0.25) F1A(0.25)
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6)
3.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.45789(4) 0.32081(2) 0.38851(4) 0.02612(12) Uani 1 1 d . . . . .
Br2 Br 0.6114(2) 0.2500 0.8377(2) 0.0315(3) Uani 0.5 2 d S T P A 1
Br2A Br 0.9148(2) 0.2500 0.5444(2) 0.0346(3) Uani 0.5 2 d S T P A 2
F1 F 0.8542(11) 0.2500 0.4492(12) 0.0415(16) Uani 0.5 2 d S T P A 1
F1A F 0.5232(11) 0.2500 0.7799(10) 0.0257(13) Uani 0.5 2 d S T P A 2
C1 C 0.6012(8) 0.2500 0.5288(7) 0.0394(10) Uani 1 2 d S T P . .
N1 N 0.1919(3) 0.41013(8) 0.1567(3) 0.0187(4) Uani 1 1 d . . . . .
C2 C 0.0250(4) 0.42821(10) 0.3263(4) 0.0230(5) Uani 1 1 d . . . . .
H2A H -0.0833 0.4587 0.2600 0.035 Uiso 1 1 calc R U . . .
H2B H 0.1138 0.4446 0.4609 0.035 Uiso 1 1 calc R U . . .
H2C H -0.0672 0.3935 0.3714 0.035 Uiso 1 1 calc R U . . .
C3 C 0.0819(4) 0.37004(10) -0.0163(4) 0.0234(5) Uani 1 1 d . . . . .
H3A H -0.0186 0.3410 0.0577 0.035 Uiso 1 1 calc R U . . .
H3B H 0.2066 0.3490 -0.0946 0.035 Uiso 1 1 calc R U . . .
H3C H -0.0160 0.3933 -0.1280 0.035 Uiso 1 1 calc R U . . .
C4 C 0.3410(4) 0.45548(9) 0.0773(4) 0.0169(4) Uani 1 1 d . . . . .
C5 C 0.3814(4) 0.50885(10) 0.1958(4) 0.0190(4) Uani 1 1 d . . . . .
H5 H 0.3008 0.5158 0.3315 0.023 Uiso 1 1 calc R U . . .
C6 C 0.5355(3) 0.55197(10) 0.1216(3) 0.0187(5) Uani 1 1 d . . . . .
H6 H 0.5580 0.5876 0.2081 0.022 Uiso 1 1 calc R U . . .


_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 1.941(2) . ?
Br2 C1 1.806(4) . ?
Br2A C1 1.760(4) . ?
F1 C1 1.522(8) . ?
F1A C1 1.559(7) . ?
C1 Br1 1.941(2) 4_565 ?
N1 C2 1.462(3) . ?
N1 C3 1.465(3) . ?
N1 C4 1.414(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.395(3) . ?
C4 C6 1.401(3) 3_665 ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C6 C4 1.400(3) 3_665 ?
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
Br1 C1 Br1 109.75(17) 4_565 . ?
Br2 C1 Br1 114.33(16) . 4_565 ?
Br2 C1 Br1 114.33(16) . . ?
Br2A C1 Br1 114.33(16) . . ?
Br2A C1 Br1 114.33(16) . 4_565 ?
F1 C1 Br1 104.1(2) . 4_565 ?
F1 C1 Br1 104.1(2) . . ?
F1 C1 Br2 109.3(3) . . ?
F1A C1 Br1 105.5(2) . . ?
F1A C1 Br1 105.5(2) . 4_565 ?
F1A C1 Br2A 106.7(3) . . ?
C2 N1 C3 112.21(17) . . ?
C4 N1 C2 116.11(17) . . ?
C4 N1 C3 116.66(17) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 N1 122.42(19) . . ?
C5 C4 C6 116.2(2) . 3_665 ?
C6 C4 N1 121.34(19) 3_665 . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.0(2) . . ?
C6 C5 H5 119.0 . . ?
C4 C6 H6 119.1 3_665 . ?
C5 C6 C4 121.8(2) . 3_665 ?
C5 C6 H6 119.1 . . ?

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
N1 C4 C5 C6 177.28(19) . . . . ?
C2 N1 C4 C5 18.5(3) . . . . ?
C2 N1 C4 C6 -164.10(18) . . . 3_665 ?
C3 N1 C4 C5 154.3(2) . . . . ?
C3 N1 C4 C6 -28.3(3) . . . 3_665 ?
C4 C5 C6 C4 0.2(3) . . . 3_665 ?
C6 C4 C5 C6 -0.2(3) 3_665 . . . ?

_shelx_estimated_absorpt_T_max   0.871
_shelx_estimated_absorpt_T_min   0.200
_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.
;
_shelxl_version_number           2012-9
####################################################################### 
# 
# 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_n2628
_database_code_depnum_ccdc_archive 'CCDC 1532255'
_audit_update_record             
;
2017-02-11 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT431_n2628               
;
PROBLEM: Short Inter HL..A  Contact Br6    ..  N3      ..       2.72 Ang.
RESPONSE: The short contact is related to strong halogne bond which is discussed in the paper.
;
# Added during the CSD deposition process: Saturday 11 February 2017 11:38 PM
# end Validation Reply Form

_audit_creation_date             2013-04-03
_audit_creation_method           
;
  Olex2 1.2
  (compiled Mar 21 2013 11:17:50, GUI svn.r4446)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '4(C2 H2 Br3 N O), C10 H16 N2'
_chemical_formula_sum            'C18 H24 Br12 N6 O4'
_chemical_formula_weight         1347.35
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.0422(3)
_cell_length_b                   5.94620(10)
_cell_length_c                   20.4996(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.4347(11)
_cell_angle_gamma                90
_cell_volume                     1708.60(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.39
_exptl_absorpt_coefficient_mu    14.102
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0875 before and 0.0499 after correction.
The Ratio of minimum to maximum transmission is 0.7075.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.619
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.017
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            25906
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.543
_diffrn_reflns_theta_min         1.453
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4318
_reflns_number_total             5190
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.168
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         5190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0221
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0343P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0513
_refine_ls_wR_factor_ref         0.0674
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups, All N(H,H) groups
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.22770(2) 0.83719(5) 0.71529(2) 0.01859(7) Uani 1 1 d . . . . .
Br2 Br 0.22366(2) 0.78612(5) 0.56284(2) 0.01652(7) Uani 1 1 d . . . . .
Br3 Br 0.34367(2) 0.44488(5) 0.65586(2) 0.01622(7) Uani 1 1 d . . . . .
O1 O 0.42813(14) 0.9126(4) 0.58424(9) 0.0173(4) Uani 1 1 d . . . . .
N1 N 0.43273(18) 0.9791(4) 0.69310(11) 0.0130(5) Uani 1 1 d . . . . .
H1A H 0.412(2) 0.966(6) 0.7288(16) 0.016 Uiso 1 1 d . U . . .
H1B H 0.484(2) 1.059(6) 0.6903(15) 0.016 Uiso 1 1 d . U . . .
C1 C 0.30175(19) 0.7527(5) 0.64249(12) 0.0113(5) Uani 1 1 d . . . . .
C2 C 0.39435(19) 0.8926(5) 0.63781(13) 0.0121(5) Uani 1 1 d . . . . .
Br4 Br 0.67320(2) 0.78655(5) 0.67204(2) 0.01408(7) Uani 1 1 d . . . . .
Br5 Br 0.65946(2) 0.70855(5) 0.52083(2) 0.01509(7) Uani 1 1 d . . . . .
Br6 Br 0.80376(2) 0.41486(5) 0.61098(2) 0.01092(6) Uani 1 1 d . . . . .
O2 O 0.58180(14) 0.3292(3) 0.67077(9) 0.0143(4) Uani 1 1 d . . . . .
N2 N 0.57366(19) 0.2588(4) 0.56248(12) 0.0152(5) Uani 1 1 d . . . . .
H2A H 0.544(2) 0.142(6) 0.5641(15) 0.018 Uiso 1 1 d . U . . .
H2B H 0.596(2) 0.285(6) 0.5257(16) 0.018 Uiso 1 1 d . U . . .
C3 C 0.67797(19) 0.5608(5) 0.60461(12) 0.0115(5) Uani 1 1 d . . . . .
C4 C 0.60448(18) 0.3726(5) 0.61515(13) 0.0113(5) Uani 1 1 d . . . . .
N3 N 0.97727(17) 0.2098(4) 0.62236(11) 0.0142(5) Uani 1 1 d . . . . .
C5 C 0.99014(18) 0.1051(5) 0.56127(12) 0.0115(5) Uani 1 1 d . . . . .
C6 C 0.9401(2) -0.0898(5) 0.54358(14) 0.0156(6) Uani 1 1 d . . . . .
H6 H 0.901(2) -0.148(6) 0.5711(15) 0.019 Uiso 1 1 d . U . . .
C7 C 1.0502(2) 0.1932(5) 0.51610(14) 0.0158(6) Uani 1 1 d . . . . .
H7 H 1.082(2) 0.323(6) 0.5248(15) 0.019 Uiso 1 1 d . U . . .
C8 C 0.9618(2) 0.0589(6) 0.67662(15) 0.0187(6) Uani 1 1 d . . . . .
H8A H 0.903(2) -0.028(6) 0.6690(16) 0.022 Uiso 1 1 d . U . . .
H8B H 0.957(2) 0.133(6) 0.7182(16) 0.022 Uiso 1 1 d . U . . .
H8C H 1.016(2) -0.038(6) 0.6826(16) 0.022 Uiso 1 1 d . U . . .
C9 C 1.0441(2) 0.3908(6) 0.64053(16) 0.0216(7) Uani 1 1 d . . . . .
H9A H 1.039(2) 0.520(6) 0.6058(17) 0.026 Uiso 1 1 d . U . . .
H9B H 1.028(2) 0.454(6) 0.6852(17) 0.026 Uiso 1 1 d . U . . .
H9C H 1.102(3) 0.346(6) 0.6460(16) 0.026 Uiso 1 1 d . U . . .


_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 1.936(3) . ?
Br2 C1 1.922(3) . ?
Br3 C1 1.937(3) . ?
O1 C2 1.228(3) . ?
N1 H1A 0.81(3) . ?
N1 H1B 0.87(3) . ?
N1 C2 1.329(3) . ?
C1 C2 1.552(4) . ?
Br4 C3 1.931(3) . ?
Br5 C3 1.933(2) . ?
Br6 C3 1.965(3) . ?
O2 C4 1.229(3) . ?
N2 H2A 0.81(4) . ?
N2 H2B 0.85(3) . ?
N2 C4 1.325(3) . ?
C3 C4 1.546(4) . ?
N3 C5 1.420(3) . ?
N3 C8 1.455(4) . ?
N3 C9 1.461(4) . ?
C5 C6 1.392(4) . ?
C5 C7 1.392(4) . ?
C6 H6 0.88(3) . ?
C6 C7 1.383(4) 3_756 ?
C7 C6 1.383(4) 3_756 ?
C7 H7 0.90(3) . ?
C8 H8A 0.98(4) . ?
C8 H8B 0.97(3) . ?
C8 H8C 0.96(3) . ?
C9 H9A 1.05(4) . ?
C9 H9B 1.03(3) . ?
C9 H9C 0.85(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
H1A N1 H1B 117(3) . . ?
C2 N1 H1A 126(2) . . ?
C2 N1 H1B 117(2) . . ?
Br1 C1 Br3 108.00(13) . . ?
Br2 C1 Br1 108.82(13) . . ?
Br2 C1 Br3 111.79(13) . . ?
C2 C1 Br1 113.53(18) . . ?
C2 C1 Br2 109.24(17) . . ?
C2 C1 Br3 105.48(18) . . ?
O1 C2 N1 124.5(3) . . ?
O1 C2 C1 118.5(2) . . ?
N1 C2 C1 117.0(2) . . ?
H2A N2 H2B 114(3) . . ?
C4 N2 H2A 123(2) . . ?
C4 N2 H2B 121(2) . . ?
Br4 C3 Br5 108.15(13) . . ?
Br4 C3 Br6 109.20(12) . . ?
Br5 C3 Br6 109.40(13) . . ?
C4 C3 Br4 110.56(17) . . ?
C4 C3 Br5 113.45(17) . . ?
C4 C3 Br6 106.01(17) . . ?
O2 C4 N2 123.9(3) . . ?
O2 C4 C3 119.6(2) . . ?
N2 C4 C3 116.4(2) . . ?
C5 N3 C8 115.9(2) . . ?
C5 N3 C9 115.7(2) . . ?
C8 N3 C9 112.5(2) . . ?
C6 C5 N3 120.4(2) . . ?
C7 C5 N3 122.4(3) . . ?
C7 C5 C6 117.2(2) . . ?
C5 C6 H6 119(2) . . ?
C7 C6 C5 121.7(3) 3_756 . ?
C7 C6 H6 119(2) 3_756 . ?
C5 C7 H7 120(2) . . ?
C6 C7 C5 121.1(3) 3_756 . ?
C6 C7 H7 119(2) 3_756 . ?
N3 C8 H8A 111.5(19) . . ?
N3 C8 H8B 114(2) . . ?
N3 C8 H8C 108(2) . . ?
H8A C8 H8B 106(3) . . ?
H8A C8 H8C 111(3) . . ?
H8B C8 H8C 105(3) . . ?
N3 C9 H9A 110.6(19) . . ?
N3 C9 H9B 109(2) . . ?
N3 C9 H9C 113(2) . . ?
H9A C9 H9B 109(3) . . ?
H9A C9 H9C 110(3) . . ?
H9B C9 H9C 105(3) . . ?

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
N1 H1A O2 0.81(3) 2.21(3) 2.948(3) 152(3) 2_656
N1 H1B O2 0.87(3) 2.16(3) 3.007(3) 163(3) 1_565
N2 H2A O1 0.81(4) 2.18(4) 2.953(3) 159(3) 1_545

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
Br1 C1 C2 O1 -154.7(2) . . . . ?
Br1 C1 C2 N1 26.7(3) . . . . ?
Br2 C1 C2 O1 -33.0(3) . . . . ?
Br2 C1 C2 N1 148.4(2) . . . . ?
Br3 C1 C2 O1 87.3(3) . . . . ?
Br3 C1 C2 N1 -91.3(2) . . . . ?
Br4 C3 C4 O2 -28.8(3) . . . . ?
Br4 C3 C4 N2 154.8(2) . . . . ?
Br5 C3 C4 O2 -150.5(2) . . . . ?
Br5 C3 C4 N2 33.1(3) . . . . ?
Br6 C3 C4 O2 89.4(3) . . . . ?
Br6 C3 C4 N2 -87.0(2) . . . . ?
N3 C5 C6 C7 178.8(3) . . . 3_756 ?
N3 C5 C7 C6 -178.7(3) . . . 3_756 ?
C6 C5 C7 C6 -0.4(5) . . . 3_756 ?
C7 C5 C6 C7 0.4(5) . . . 3_756 ?
C8 N3 C5 C6 35.6(4) . . . . ?
C8 N3 C5 C7 -146.1(3) . . . . ?
C9 N3 C5 C6 170.4(3) . . . . ?
C9 N3 C5 C7 -11.3(4) . . . . ?

_shelx_estimated_absorpt_T_max   0.796
_shelx_estimated_absorpt_T_min   0.046
_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.
;
_shelxl_version_number           2012-9
_vrf_PLAT431_I                   
;
PROBLEM: Short Inter HL..A  Contact  Br6    ..  N3      .       2.72 Ang. 
RESPONSE: We are confident in our structural assignments
;
# end Validation Reply Form
