# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_100K
_database_code_depnum_ccdc_archive 'CCDC 1537381'
_audit_update_record             
;
2017-03-11 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H14 Br4 Fe N'
_chemical_formula_weight         475.67

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   6.59740(10)
_cell_length_b                   13.7002(3)
_cell_length_c                   14.6244(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.590(2)
_cell_angle_gamma                90.00
_cell_volume                     1320.49(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(6)
_cell_measurement_reflns_used    4581
_cell_measurement_theta_min      4.3850
_cell_measurement_theta_max      73.1720

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             892
_exptl_absorpt_coefficient_mu    22.998
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100.0(6)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6995
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.42
_diffrn_reflns_theta_max         87.58
_reflns_number_total             2522
_reflns_number_gt                2318
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1821P)²+0.4112P] 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         2522
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0889
_refine_ls_wR_factor_ref         0.2364
_refine_ls_wR_factor_gt          0.2314
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
Br3 Br 0.02893(14) 0.26248(6) 0.09975(7) 0.0422(4) Uani 1 1 d . . .
Br1 Br -0.39261(14) 0.26823(7) 0.27541(6) 0.0412(4) Uani 1 1 d . . .
Br4 Br -0.42976(14) 0.11165(6) 0.04660(6) 0.0417(4) Uani 1 1 d . . .
Br2 Br -0.47895(14) 0.37412(6) 0.02522(6) 0.0431(4) Uani 1 1 d . . .
Fe1 Fe -0.3250(2) 0.25353(8) 0.10900(9) 0.0356(4) Uani 1 1 d . . .
C4 C -0.0792(14) 0.5933(7) 0.1682(6) 0.0461(19) Uani 1 1 d . . .
H4A H -0.1516 0.6221 0.1140 0.055 Uiso 1 1 calc R . .
H4B H -0.0059 0.6467 0.2011 0.055 Uiso 1 1 calc R . .
C5 C 0.0708(15) 0.5223(7) 0.1368(6) 0.049(2) Uani 1 1 d . . .
H5A H 0.1746 0.5556 0.1012 0.058 Uiso 1 1 calc R . .
H5B H 0.0034 0.4720 0.0975 0.058 Uiso 1 1 calc R . .
C1 C 0.1021(17) 0.3807(7) 0.3724(7) 0.049(2) Uani 1 1 d . . .
H1A H 0.1744 0.4287 0.4114 0.073 Uiso 1 1 calc R . .
H1B H 0.1971 0.3300 0.3541 0.073 Uiso 1 1 calc R . .
H1C H -0.0066 0.3508 0.4063 0.073 Uiso 1 1 calc R . .
C2 C -0.1393(14) 0.5024(6) 0.3188(6) 0.0434(18) Uani 1 1 d . . .
H2A H -0.0722 0.5525 0.3584 0.052 Uiso 1 1 calc R . .
H2B H -0.2437 0.4690 0.3539 0.052 Uiso 1 1 calc R . .
N1 N 0.0115(11) 0.4312(5) 0.2876(4) 0.0390(14) Uani 1 1 d . . .
H1 H -0.0594 0.3841 0.2533 0.047 Uiso 1 1 calc R . .
C6 C 0.1721(13) 0.4740(6) 0.2266(6) 0.0419(17) Uani 1 1 d . . .
H6A H 0.2661 0.4216 0.2090 0.050 Uiso 1 1 calc R . .
H6B H 0.2521 0.5239 0.2614 0.050 Uiso 1 1 calc R . .
C3 C -0.2373(14) 0.5502(7) 0.2316(6) 0.0476(19) Uani 1 1 d . . .
H3A H -0.3193 0.5007 0.1972 0.057 Uiso 1 1 calc R . .
H3B H -0.3301 0.6028 0.2498 0.057 Uiso 1 1 calc R . .


_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 Fe1 2.3482(16) . ?
Br1 Fe1 2.5020(15) . ?
Br4 Fe1 2.2432(14) . ?
Br2 Fe1 2.2692(15) . ?
C4 C5 1.475(14) . ?
C4 C3 1.543(13) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.591(13) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C1 N1 1.518(11) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.480(11) . ?
C2 C3 1.549(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N1 C6 1.533(10) . ?
N1 H1 0.9300 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

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
Br4 Fe1 Br2 106.80(6) . . ?
Br4 Fe1 Br3 108.10(6) . . ?
Br2 Fe1 Br3 110.66(6) . . ?
Br4 Fe1 Br1 113.59(6) . . ?
Br2 Fe1 Br1 111.80(6) . . ?
Br3 Fe1 Br1 105.86(6) . . ?
C5 C4 C3 114.6(8) . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C6 106.2(7) . . ?
C4 C5 H5A 110.5 . . ?
C6 C5 H5A 110.5 . . ?
C4 C5 H5B 110.5 . . ?
C6 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 106.7(7) . . ?
N1 C2 H2A 110.4 . . ?
C3 C2 H2A 110.4 . . ?
N1 C2 H2B 110.4 . . ?
C3 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C2 N1 C6 114.8(6) . . ?
C2 N1 C1 107.1(7) . . ?
C6 N1 C1 113.1(7) . . ?
C2 N1 H1 107.1 . . ?
C6 N1 H1 107.1 . . ?
C1 N1 H1 107.1 . . ?
N1 C6 C5 111.3(7) . . ?
N1 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C4 C3 C2 112.8(7) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?

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
C3 C4 C5 C6 -55.0(10) . . . . ?
C3 C2 N1 C6 55.9(9) . . . . ?
C3 C2 N1 C1 -177.6(7) . . . . ?
C2 N1 C6 C5 -59.0(9) . . . . ?
C1 N1 C6 C5 177.7(7) . . . . ?
C4 C5 C6 N1 54.3(9) . . . . ?
C5 C4 C3 C2 58.0(11) . . . . ?
N1 C2 C3 C4 -53.5(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.838
_diffrn_reflns_theta_full        87.58
_diffrn_measured_fraction_theta_full 0.837
_refine_diff_density_max         3.087
_refine_diff_density_min         -1.235
_refine_diff_density_rms         0.487
####################################################################### 
# 
# 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_345k
_database_code_depnum_ccdc_archive 'CCDC 1537458'
_audit_update_record             
;
2017-07-10 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H14 Br4 Fe N'
_chemical_formula_weight         475.67

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'
Fe Fe -1.1336 3.1974 '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      orthorhombic
_space_group_IT_number           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'

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

_cell_length_a                   9.9932(4)
_cell_length_b                   9.5392(4)
_cell_length_c                   14.8097(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1411.77(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    345.00(10)
_cell_measurement_reflns_used    1039
_cell_measurement_theta_min      5.9720
_cell_measurement_theta_max      71.8500

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.238
_exptl_crystal_F_000             892
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    21.511
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      345.00(10)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2189
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.976
_diffrn_reflns_theta_max         72.702
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             761
_reflns_number_gt                615
_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0800P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00073(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         761
_refine_ls_number_parameters     50
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1588
_refine_ls_wR_factor_gt          0.1477
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.011
_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_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
Fe1 Fe 0.000000 0.1923(2) 0.250000 0.0718(6) Uani 1 4 d S T P . .
Br1 Br 0.18738(15) 0.33823(16) 0.250000 0.1226(7) Uani 1 2 d S T P . .
Br2 Br 0.000000 0.05718(16) 0.37941(8) 0.1210(7) Uani 1 2 d S T P . .
N1 N 0.000000 0.469(2) 0.5611(14) 0.125(5) Uani 0.5 2 d DS TU P . .
H1A H 0.000000 0.544149 0.597629 0.150 Uiso 0.5 2 d R U P . .
C1 C 0.1244(16) 0.500000 0.500000 0.137(4) Uani 1 2 d DS TU P . .
H1B H 0.137389 0.423300 0.458960 0.164 Uiso 0.5 1 d R U P . .
H1C H 0.202999 0.506530 0.537060 0.164 Uiso 0.5 1 d R U P . .
C2 C 0.114(2) 0.620(2) 0.4548(13) 0.136(5) Uani 0.5 1 d D U P . .
H2A H 0.187842 0.622046 0.413128 0.163 Uiso 0.5 1 d R U P . .
H2B H 0.126452 0.696426 0.495798 0.163 Uiso 0.5 1 d R U P . .
C3 C 0.000000 0.637(5) 0.410(3) 0.143(7) Uani 0.5 2 d DS TU P . .
H3A H 0.000000 0.579838 0.356594 0.172 Uiso 0.5 2 d R U P . .
H3B H 0.000000 0.733408 0.391064 0.172 Uiso 0.5 2 d R U P . .
C4 C 0.000000 0.335(4) 0.621(3) 0.147(8) Uani 0.5 2 d DS TU P . .
H4A H -0.084850 0.332452 0.651499 0.221 Uiso 0.25 1 d R U P . .
H4B H 0.014980 0.246912 0.591239 0.221 Uiso 0.25 1 d R U P . .
H4C H 0.069860 0.350802 0.664419 0.221 Uiso 0.25 1 d R U P . .


_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
Fe1 Br2 2.3096(15) . ?
Fe1 Br2 2.3096(15) 10_556 ?
Fe1 Br1 2.3333(17) 3 ?
Fe1 Br1 2.3333(17) . ?
N1 C3 1.10(5) 9_566 ?
N1 C2 1.44(3) 9_566 ?
N1 C2 1.44(3) 4_566 ?
N1 C4 1.56(2) . ?
N1 C1 1.567(16) 9_566 ?
N1 C1 1.567(16) . ?
N1 H1A 0.9000 . ?
N1 H3A 1.30(4) 9_566 ?
C1 C2 1.326(17) . ?
C1 C2 1.327(17) 4_566 ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1B 0.9599 4_566 ?
C1 H1C 0.9601 4_566 ?
C2 C3 1.332(18) . ?
C2 C4 1.66(3) 9_566 ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C3 C4 0.53(5) 9_566 ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9599 . ?
C4 H4A 0.9600 12 ?
C4 H4B 0.9600 12 ?
C4 H4C 0.9599 12 ?

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
Br2 Fe1 Br2 112.16(11) . 10_556 ?
Br2 Fe1 Br1 109.45(3) . 3 ?
Br2 Fe1 Br1 109.45(3) 10_556 3 ?
Br2 Fe1 Br1 109.45(3) . . ?
Br2 Fe1 Br1 109.45(3) 10_556 . ?
Br1 Fe1 Br1 106.74(11) 3 . ?
C3 N1 C2 61.7(13) 9_566 9_566 ?
C3 N1 C2 61.7(13) 9_566 4_566 ?
C2 N1 C2 105(2) 9_566 4_566 ?
C3 N1 C4 12(3) 9_566 . ?
C2 N1 C4 67.2(13) 9_566 . ?
C2 N1 C4 67.2(13) 4_566 . ?
C3 N1 C1 113.7(17) 9_566 9_566 ?
C2 N1 C1 52.2(7) 9_566 9_566 ?
C2 N1 C1 130.3(18) 4_566 9_566 ?
C4 N1 C1 119.1(12) . 9_566 ?
C3 N1 C1 113.7(17) 9_566 . ?
C2 N1 C1 130.3(18) 9_566 . ?
C2 N1 C1 52.2(7) 4_566 . ?
C4 N1 C1 119.1(12) . . ?
C1 N1 C1 105.0(15) 9_566 . ?
C3 N1 H1A 120.1 9_566 . ?
C2 N1 H1A 124.5 9_566 . ?
C2 N1 H1A 124.5 4_566 . ?
C4 N1 H1A 108.3 . . ?
C1 N1 H1A 101.2 9_566 . ?
C1 N1 H1A 101.2 . . ?
C3 N1 H3A 46.2(17) 9_566 9_566 ?
C2 N1 H3A 86.9(18) 9_566 9_566 ?
C2 N1 H3A 86.9(18) 4_566 9_566 ?
C4 N1 H3A 34(3) . 9_566 ?
C1 N1 H3A 127.4(8) 9_566 9_566 ?
C1 N1 H3A 127.4(8) . 9_566 ?
H1A N1 H3A 73.9 . 9_566 ?
C2 C1 C2 171(2) . 4_566 ?
C2 C1 N1 58.9(13) . 9_566 ?
C2 C1 N1 113.3(16) 4_566 9_566 ?
C2 C1 N1 113.3(16) . . ?
C2 C1 N1 58.9(13) 4_566 . ?
N1 C1 N1 75.0(15) 9_566 . ?
C2 C1 H1B 110.2 . . ?
C2 C1 H1B 71.0 4_566 . ?
N1 C1 H1B 83.5 9_566 . ?
N1 C1 H1B 109.1 . . ?
C2 C1 H1C 107.2 . . ?
C2 C1 H1C 80.2 4_566 . ?
N1 C1 H1C 165.3 9_566 . ?
N1 C1 H1C 109.3 . . ?
H1B C1 H1C 107.5 . . ?
C2 C1 H1B 71.0(9) . 4_566 ?
C2 C1 H1B 110.2(9) 4_566 4_566 ?
N1 C1 H1B 109.1(9) 9_566 4_566 ?
N1 C1 H1B 83.5(9) . 4_566 ?
H1B C1 H1B 164.5 . 4_566 ?
H1C C1 H1B 58.5 . 4_566 ?
C2 C1 H1C 80.2(12) . 4_566 ?
C2 C1 H1C 107.2(11) 4_566 4_566 ?
N1 C1 H1C 109.3(8) 9_566 4_566 ?
N1 C1 H1C 165.2(9) . 4_566 ?
H1B C1 H1C 58.5 . 4_566 ?
H1C C1 H1C 70.3 . 4_566 ?
H1B C1 H1C 107.5 4_566 4_566 ?
C1 C2 C3 115(3) . . ?
C1 C2 N1 68.9(14) . 9_566 ?
C3 C2 N1 46(2) . 9_566 ?
C1 C2 C4 128(2) . 9_566 ?
C3 C2 C4 16.2(16) . 9_566 ?
N1 C2 C4 59.8(11) 9_566 9_566 ?
C1 C2 H2A 106.7 . . ?
C3 C2 H2A 109.4 . . ?
N1 C2 H2A 121.1 9_566 . ?
C4 C2 H2A 94.9 9_566 . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.2 . . ?
N1 C2 H2B 130.7 9_566 . ?
C4 C2 H2B 108.4 9_566 . ?
H2A C2 H2B 106.9 . . ?
C1 C2 H1B 41.8(5) . 4_566 ?
C3 C2 H1B 131(3) . 4_566 ?
N1 C2 H1B 96.5(16) 9_566 4_566 ?
C4 C2 H1B 146(2) 9_566 4_566 ?
H2A C2 H1B 118.7 . 4_566 ?
H2B C2 H1B 67.3 . 4_566 ?
C1 C2 H1C 39.1(5) . 4_566 ?
C3 C2 H1C 130(3) . 4_566 ?
N1 C2 H1C 90.8(14) 9_566 4_566 ?
C4 C2 H1C 132(2) 9_566 4_566 ?
H2A C2 H1C 67.6 . 4_566 ?
H2B C2 H1C 119.1 . 4_566 ?
H1B C2 H1C 65.4 4_566 4_566 ?
C4 C3 N1 143(10) 9_566 9_566 ?
C4 C3 C2 120(3) 9_566 12 ?
N1 C3 C2 72(2) 9_566 12 ?
C4 C3 C2 120(3) 9_566 . ?
N1 C3 C2 72(2) 9_566 . ?
C2 C3 C2 118(3) 12 . ?
C4 C3 H3A 64.9 9_566 . ?
N1 C3 H3A 78.3 9_566 . ?
C2 C3 H3A 109.8 12 . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3B 42.9 9_566 . ?
N1 C3 H3B 173.9 9_566 . ?
C2 C3 H3B 105.4 12 . ?
C2 C3 H3B 105.4 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 N1 25(8) 9_566 . ?
C3 C4 C2 44.2(19) 9_566 9_566 ?
N1 C4 C2 53.0(13) . 9_566 ?
C3 C4 C2 44.2(19) 9_566 4_566 ?
N1 C4 C2 53.0(13) . 4_566 ?
C2 C4 C2 87(2) 9_566 4_566 ?
C3 C4 H4A 114.6 9_566 . ?
N1 C4 H4A 106.7 . . ?
C2 C4 H4A 73.5 9_566 . ?
C2 C4 H4A 158.5 4_566 . ?
C3 C4 H4B 92.4 9_566 . ?
N1 C4 H4B 117.0 . . ?
C2 C4 H4B 91.4 9_566 . ?
C2 C4 H4B 79.0 4_566 . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 119.8 9_566 . ?
N1 C4 H4C 104.5 . . ?
C2 C4 H4C 155.6 9_566 . ?
C2 C4 H4C 84.9 4_566 . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C4 H3A 82(9) 9_566 9_566 ?
N1 C4 H3A 57(3) . 9_566 ?
C2 C4 H3A 91(3) 9_566 9_566 ?
C2 C4 H3A 91(3) 4_566 9_566 ?
H4A C4 H3A 81.1 . 9_566 ?
H4B C4 H3A 169.3 . 9_566 ?
H4C C4 H3A 66.6 . 9_566 ?
C3 C4 H3B 105(10) 9_566 9_566 ?
N1 C4 H3B 130(6) . 9_566 ?
C2 C4 H3B 94(4) 9_566 9_566 ?
C2 C4 H3B 94(4) 4_566 9_566 ?
H4A C4 H3B 95.9 . 9_566 ?
H4B C4 H3B 15.2 . 9_566 ?
H4C C4 H3B 109.4 . 9_566 ?
H3A C4 H3B 173.5 9_566 9_566 ?
C3 C4 H4A 115(2) 9_566 12 ?
N1 C4 H4A 106.7(7) . 12 ?
C2 C4 H4A 158.5(12) 9_566 12 ?
C2 C4 H4A 73.5(12) 4_566 12 ?
H4A C4 H4A 124.1 . 12 ?
H4B C4 H4A 93.3 . 12 ?
H4C C4 H4A 17.9 . 12 ?
H3A C4 H4A 81.1 9_566 12 ?
H3B C4 H4A 95.9 9_566 12 ?
C3 C4 H4B 92(9) 9_566 12 ?
N1 C4 H4B 117.0(17) . 12 ?
C2 C4 H4B 79.0(16) 9_566 12 ?
C2 C4 H4B 91.4(16) 4_566 12 ?
H4A C4 H4B 93.3 . 12 ?
H4B C4 H4B 17.9 . 12 ?
H4C C4 H4B 124.1 . 12 ?
H3A C4 H4B 169.3 9_566 12 ?
H3B C4 H4B 15.2 9_566 12 ?
H4A C4 H4B 109.5 12 12 ?
C3 C4 H4C 120(5) 9_566 12 ?
N1 C4 H4C 104.5(12) . 12 ?
C2 C4 H4C 84.9(13) 9_566 12 ?
C2 C4 H4C 155.6(15) 4_566 12 ?
H4A C4 H4C 17.9 . 12 ?
H4B C4 H4C 124.1 . 12 ?
H4C C4 H4C 93.3 . 12 ?
H3A C4 H4C 66.6 9_566 12 ?
H3B C4 H4C 109.4 9_566 12 ?
H4A C4 H4C 109.5 12 12 ?
H4B C4 H4C 109.5 12 12 ?

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
C3 N1 C1 C2 171(3) 9_566 . . . ?
C2 N1 C1 C2 99(2) 9_566 . . . ?
C2 N1 C1 C2 175.5(12) 4_566 . . . ?
C4 N1 C1 C2 -178(2) . . . . ?
C1 N1 C1 C2 45.8(18) 9_566 . . . ?
C3 N1 C1 C2 -5(3) 9_566 . . 4_566 ?
C2 N1 C1 C2 -77(2) 9_566 . . 4_566 ?
C4 N1 C1 C2 7(2) . . . 4_566 ?
C1 N1 C1 C2 -129.8(19) 9_566 . . 4_566 ?
C3 N1 C1 N1 125(3) 9_566 . . 9_566 ?
C2 N1 C1 N1 52.8(14) 9_566 . . 9_566 ?
C2 N1 C1 N1 129.8(19) 4_566 . . 9_566 ?
C4 N1 C1 N1 137(3) . . . 9_566 ?
C1 N1 C1 N1 -0.001(2) 9_566 . . 9_566 ?
N1 C1 C2 C3 4(2) 9_566 . . . ?
N1 C1 C2 C3 -50(3) . . . . ?
N1 C1 C2 N1 -54(2) . . . 9_566 ?
N1 C1 C2 C4 -7(2) 9_566 . . 9_566 ?
N1 C1 C2 C4 -61(3) . . . 9_566 ?
C1 C2 C3 C4 -147(11) . . . 9_566 ?
N1 C2 C3 C4 -142(13) 9_566 . . 9_566 ?
C1 C2 C3 N1 -5(3) . . . 9_566 ?
C4 C2 C3 N1 142(13) 9_566 . . 9_566 ?
C1 C2 C3 C2 52(5) . . . 12 ?
N1 C2 C3 C2 57(3) 9_566 . . 12 ?
C4 C2 C3 C2 -161(15) 9_566 . . 12 ?
C2 N1 C4 C3 59.4(13) 9_566 . . 9_566 ?
C2 N1 C4 C3 -59.4(12) 4_566 . . 9_566 ?
C1 N1 C4 C3 65.3(15) 9_566 . . 9_566 ?
C1 N1 C4 C3 -65.3(16) . . . 9_566 ?
C3 N1 C4 C2 -59.4(13) 9_566 . . 9_566 ?
C2 N1 C4 C2 -119(2) 4_566 . . 9_566 ?
C1 N1 C4 C2 5.8(18) 9_566 . . 9_566 ?
C1 N1 C4 C2 -125(2) . . . 9_566 ?
C3 N1 C4 C2 59.4(13) 9_566 . . 4_566 ?
C2 N1 C4 C2 119(2) 9_566 . . 4_566 ?
C1 N1 C4 C2 125(2) 9_566 . . 4_566 ?
C1 N1 C4 C2 -5.8(18) . . . 4_566 ?

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 Br1 0.90 3.14 3.84(2) 135.8 9_566
N1 H1A Br1 0.90 3.14 3.84(2) 135.8 11_566
C3 H3B Br2 0.96 3.09 4.03(5) 166.3 1_565
C4 H4B Br2 0.96 2.94 3.74(4) 141.9 9_556

_refine_diff_density_max         0.466
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.102

