# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_4-BBN-S
_database_code_depnum_ccdc_archive 'CCDC 1587640'
_audit_update_record             
;
2017-11-26 deposited with the CCDC.
2018-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        4-bromobenzonitrile
_chemical_name_common            4-bromobenzonitrile
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H4 Br N'
_chemical_formula_weight         182.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           8
_space_group_name_H-M_alt        'C m'
_space_group_name_Hall           'C -2y'

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

_cell_length_a                   9.531(2)
_cell_length_b                   8.5593(18)
_cell_length_c                   4.1352(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.295(3)
_cell_angle_gamma                90
_cell_volume                     337.34(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2352
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      26.89

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_F_000             176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.910
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    5.990
_shelx_estimated_absorpt_T_min   0.074
_shelx_estimated_absorpt_T_max   0.575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.074
_exptl_absorpt_correction_T_max  0.575
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3422
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.199
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             893
_reflns_number_gt                869
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.989
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1247P)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_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.32(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         893
_refine_ls_number_parameters     49
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1534
_refine_ls_wR_factor_gt          0.1518
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.086
_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
Br1 Br 0.10141(2) 0.000000 0.98837(2) 0.0487(5) Uani 1 2 d S T P . .
N1 N 0.771(2) 0.000000 0.182(6) 0.075(5) Uani 1 2 d S T P . .
C1 C 0.2787(14) 0.000000 0.786(3) 0.037(2) Uani 1 2 d S T P . .
C2 C 0.3408(12) 0.1410(11) 0.710(3) 0.0450(19) Uani 1 1 d . . . . .
H2 H 0.297792 0.234665 0.766103 0.054 Uiso 1 1 calc R U . . .
C3 C 0.4688(11) 0.1412(12) 0.548(3) 0.0453(19) Uani 1 1 d . . . . .
H3 H 0.511673 0.235212 0.493897 0.054 Uiso 1 1 calc R U . . .
C4 C 0.5322(15) 0.000000 0.467(4) 0.040(3) Uani 1 2 d S T P . .
C5 C 0.6666(19) 0.000000 0.309(5) 0.054(3) Uani 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0472(6) 0.0522(7) 0.0468(6) 0.000 0.0083(4) 0.000
N1 0.062(10) 0.074(12) 0.090(13) 0.000 0.023(9) 0.000
C1 0.040(6) 0.039(6) 0.034(5) 0.000 -0.001(4) 0.000
C2 0.052(5) 0.032(4) 0.051(5) -0.003(4) 0.003(4) 0.002(4)
C3 0.050(5) 0.033(4) 0.052(5) 0.000(4) 0.002(4) -0.005(4)
C4 0.045(7) 0.041(6) 0.034(6) 0.000 -0.001(5) 0.000
C5 0.050(8) 0.053(9) 0.059(11) 0.000 0.005(7) 0.000

_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 1.889(13) . ?
Br1 N1 3.25(2) 2_456 ?
Br1 N1 3.25(2) 1_456 ?
N1 C5 1.13(3) . ?
C1 C2 1.381(12) . ?
C1 C2 1.381(12) 2 ?
C2 C3 1.396(16) . ?
C3 C4 1.392(13) . ?
C4 C5 1.44(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
C1 Br1 N1 168.0(6) . 2_456 ?
C1 Br1 N1 168.0(6) . 1_456 ?
N1 Br1 N1 0.0(9) 2_456 1_456 ?
C2 C1 C2 121.8(13) . 2 ?
C2 C1 Br1 119.1(7) . . ?
C2 C1 Br1 119.1(7) 2 . ?
C1 C2 C3 119.1(10) . . ?
C4 C3 C2 119.7(10) . . ?
C3 C4 C3 120.5(14) 2 . ?
C3 C4 C5 119.7(7) 2 . ?
C3 C4 C5 119.7(7) . . ?
N1 C5 C4 179(3) . . ?

_refine_diff_density_max         0.667
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.082

_shelx_res_file                  
;
TITL 273K in Cm
    C:\frames\guest\LA97D3~1\work\CHECKC~1\273k.res
    created by SHELXL-2016/6 at 12:36:47 on 30-May-2017
CELL 0.71073 9.5309 8.5593 4.1352 90.000 90.295 90.000
ZERR 2.0000 0.0020 0.0018 0.0009 0.000 0.003 0.000
LATT -7
SYMM X, -Y, Z
SFAC C H N BR
UNIT 14 8 2 2
EQIV $1 X-1,Y,1+Z
EQIV $2 X-1,-Y,1+Z
BIND Br1 N1_$1
BIND Br1 N1_$2
ACTA 50
FMAP 2 1 53
GRID
PLAN 10 0 0
MERG 2
SIZE 0.104 0.188 0.91
TEMP 0
L.S. 10
WGHT    0.124700
FVAR       0.26876
BR1   4    0.101410    0.000000    0.988370    10.50000    0.04723    0.05225 =
         0.04681    0.00000    0.00828    0.00000
N1    3    0.770954    0.000000    0.182258    10.50000    0.06202    0.07436 =
         0.08988    0.00000    0.02263    0.00000
C1    1    0.278705    0.000000    0.786173    10.50000    0.03971    0.03875 =
         0.03393    0.00000   -0.00081    0.00000
C2    1    0.340782    0.141033    0.710027    11.00000    0.05168    0.03230 =
         0.05097   -0.00290    0.00278    0.00167
AFIX  43
H2    2    0.297792    0.234665    0.766103    11.00000   -1.20000
AFIX   0
C3    1    0.468841    0.141200    0.547868    11.00000    0.05009    0.03341 =
         0.05228   -0.00030    0.00225   -0.00466
AFIX  43
H3    2    0.511673    0.235212    0.493897    11.00000   -1.20000
AFIX   0
C4    1    0.532180    0.000000    0.467259    10.50000    0.04530    0.04071 =
         0.03429    0.00000   -0.00075    0.00000
C5    1    0.666643    0.000000    0.308919    10.50000    0.04974    0.05327 =
         0.05918    0.00000    0.00508    0.00000
HKLF 4




REM  273K in Cm
REM R1 =  0.0596 for     869 Fo > 4sig(Fo)  and  0.0613 for all     893 data
REM     49 parameters refined using      2 restraints

END

WGHT      0.1247      0.0000

REM Highest difference peak  0.667,  deepest hole -0.236,  1-sigma level  0.082
Q1    1   0.0937 -0.0826  1.1324  11.00000  0.05    0.67
Q2    1   0.1114 -0.0793  0.8579  11.00000  0.05    0.64
Q3    1   0.0162  0.0000  1.0169  10.50000  0.05    0.58
Q4    1   0.1848  0.0000  0.9748  10.50000  0.05    0.55
Q5    1   0.6349  0.0000  0.3576  10.50000  0.05    0.27
Q6    1   0.3973  0.1393  0.5887  11.00000  0.05    0.27
Q7    1   0.3574  0.0000  0.7357  10.50000  0.05    0.26
Q8    1   0.8041 -0.1431  0.3873  11.00000  0.05    0.25
Q9    1   0.8533  0.0000  0.2448  10.50000  0.05    0.24
Q10   1   0.3094  0.0842  0.6954  11.00000  0.05    0.24
;
_shelx_res_checksum              28535
####################################################################### 
# 
# 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_4-BBN-B
_database_code_depnum_ccdc_archive 'CCDC 1587641'
_audit_update_record             
;
2017-11-26 deposited with the CCDC.
2018-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        4-bromobenzonitirle
_chemical_name_common            4-bromobenzonitirle
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H4 Br N'
_chemical_formula_weight         182.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           8
_space_group_name_H-M_alt        'C m'
_space_group_name_Hall           'C -2y'

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

_cell_length_a                   9.509(5)
_cell_length_b                   8.535(4)
_cell_length_c                   4.127(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.311(5)
_cell_angle_gamma                90
_cell_volume                     334.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3581
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      26.02

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_F_000             176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.910
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    6.033
_shelx_estimated_absorpt_T_min   0.073
_shelx_estimated_absorpt_T_max   0.573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.073
_exptl_absorpt_correction_T_max  0.573
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4129
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.207
_diffrn_reflns_theta_max         25.332
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             655
_reflns_number_gt                652
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.985
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0728P)²+1.2112P] 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_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration ?
_refine_ls_number_reflns         655
_refine_ls_number_parameters     49
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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 0.26089(2) 0.000000 0.00591(2) 0.0503(4) Uani 1 2 d S T P . .
N1 N -0.4084(18) 0.000000 0.810(5) 0.076(4) Uani 1 2 d S T P . .
C1 C 0.0819(13) 0.000000 0.207(3) 0.037(2) Uani 1 2 d S T P . .
C2 C 0.0200(10) 0.1409(10) 0.284(2) 0.043(2) Uani 1 1 d . . . . .
H2 H 0.063039 0.234841 0.228164 0.052 Uiso 1 1 calc R U . . .
C3 C -0.1060(10) 0.1410(11) 0.446(2) 0.045(2) Uani 1 1 d . . . . .
H3 H -0.148436 0.235273 0.501572 0.054 Uiso 1 1 calc R U . . .
C4 C -0.1697(14) 0.000000 0.525(4) 0.041(3) Uani 1 2 d S T P . .
C5 C -0.3031(17) 0.000000 0.687(6) 0.054(4) Uani 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0474(6) 0.0557(7) 0.0480(6) 0.000 0.0097(4) 0.000
N1 0.066(10) 0.069(9) 0.092(12) 0.000 0.026(9) 0.000
C1 0.038(6) 0.043(6) 0.029(6) 0.000 -0.002(4) 0.000
C2 0.050(5) 0.031(4) 0.048(5) 0.005(4) 0.000(4) -0.001(3)
C3 0.051(5) 0.037(5) 0.048(5) -0.002(4) -0.003(4) 0.005(4)
C4 0.040(7) 0.044(7) 0.038(8) 0.000 -0.003(6) 0.000
C5 0.052(9) 0.050(8) 0.062(11) 0.000 0.009(8) 0.000

_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 1.897(13) . ?
N1 C5 1.12(2) . ?
C1 C2 1.377(11) . ?
C1 C2 1.377(11) 2 ?
C2 C3 1.374(14) . ?
C3 C4 1.387(12) . ?
C4 C5 1.44(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
C2 C1 C2 121.7(12) . 2 ?
C2 C1 Br1 119.1(6) . . ?
C2 C1 Br1 119.1(6) 2 . ?
C3 C2 C1 119.2(9) . . ?
C2 C3 C4 119.8(9) . . ?
C3 C4 C3 120.3(13) 2 . ?
C3 C4 C5 119.8(7) 2 . ?
C3 C4 C5 119.8(7) . . ?
N1 C5 C4 179(3) . . ?

_refine_diff_density_max         0.601
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.063

_shelx_res_file                  
;
TITL C:\frames\guest\LAB090~1\work\2B2_b_a.res in Cm
    C:\Users\lukman\Desktop\LA_SnB\bent\FINALW~1\4-BBN-B.res
    created by SHELXL-2016/6 at 19:26:31 on 07-Aug-2017
CELL 0.71073 9.5087 8.5350 4.1268 90.000 90.311 90.000
ZERR 2.0000 0.0045 0.0040 0.0020 0.000 0.005 0.000
LATT -7
SYMM X, -Y, Z
SFAC C H N BR
UNIT 14 8 2 2
BOND
OMIT -3 1 -2
OMIT -5 3 -3
ACTA 50
FMAP 2 1 53
PLAN 10 0 0
SIZE 0.91 0.188 0.104
TWIN
TEMP 0
L.S. 4
WGHT    0.072800    1.211200
FVAR       0.87493
BR1   4    0.260890    0.000000    0.005910    10.50000    0.04740    0.05566 =
         0.04800    0.00000    0.00973    0.00000
N1    3   -0.408415    0.000000    0.809986    10.50000    0.06636    0.06866 =
         0.09228    0.00000    0.02634    0.00000
C1    1    0.081904    0.000000    0.206890    10.50000    0.03834    0.04349 =
         0.02927    0.00000   -0.00170    0.00000
C2    1    0.020039    0.140894    0.284341    11.00000    0.05011    0.03131 =
         0.04798    0.00499    0.00007   -0.00137
AFIX  43
H2    2    0.063039    0.234841    0.228164    11.00000   -1.20000
AFIX   0
C3    1   -0.105994    0.140977    0.445633    11.00000    0.05127    0.03706 =
         0.04760   -0.00178   -0.00284    0.00549
AFIX  43
H3    2   -0.148436    0.235273    0.501572    11.00000   -1.20000
AFIX   0
C4    1   -0.169732    0.000000    0.524776    10.50000    0.04007    0.04447 =
         0.03777    0.00000   -0.00288    0.00000
C5    1   -0.303095    0.000000    0.687256    10.50000    0.05179    0.04961 =
         0.06186    0.00000    0.00885    0.00000
HKLF 4




REM  C:\frames\guest\LAB090~1\work\2B2_b_a.res in Cm
REM R1 =  0.0404 for     652 Fo > 4sig(Fo)  and  0.0408 for all     655 data
REM     49 parameters refined using      2 restraints

END

WGHT      0.0738      0.7978

REM Highest difference peak  0.601,  deepest hole -0.218,  1-sigma level  0.063
Q1    1   0.1854  0.0000  0.1081  10.50000  0.05    0.60
Q2    1   0.3307  0.0000 -0.0872  10.50000  0.05    0.54
Q3    1   0.3463  0.0000  0.1884  10.50000  0.05    0.39
Q4    1   0.1766  0.0000 -0.1650  10.50000  0.05    0.38
Q5    1  -0.2535  0.0000  0.5815  10.50000  0.05    0.26
Q6    1  -0.0275  0.1285  0.4309  11.00000  0.05    0.17
Q7    1  -0.1524  0.0000  0.3678  10.50000  0.05    0.16
Q8    1  -0.0880  0.1260  0.3011  11.00000  0.05    0.14
Q9    1   0.2608 -0.1205  0.0520  11.00000  0.05    0.14
Q10   1  -0.5832  0.0000  0.7426  10.50000  0.05    0.14
;
_shelx_res_checksum              3044
