# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_brfn_pvt_2
_database_code_depnum_ccdc_archive 'CCDC 1563251'
_audit_update_record             
;
2017-07-19 deposited with the CCDC.
2017-10-10 downloaded from the CCDC.
;
_audit_creation_date             2017-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        Bis(4-bromophenyl)fumaronitrile
_chemical_formula_moiety         '2(C8 H4 Br N)'
_chemical_formula_sum            'C16 H8 Br2 N2'
_chemical_formula_weight         388.06
_chemical_melting_point          493
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.87260(10)
_cell_length_b                   10.7671(4)
_cell_length_c                   16.5188(6)
_cell_angle_alpha                90.217(3)
_cell_angle_beta                 93.186(3)
_cell_angle_gamma                98.738(2)
_cell_volume                     679.68(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5106
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.952
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0675 before and 0.0382 after correction. The Ratio of minimum to maximum transmission is 0.7100. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.896
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.404
_exptl_crystal_size_min          0.198
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11146
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.881
_diffrn_reflns_theta_min         1.235
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2853
_reflns_number_total             3207
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.297
_refine_diff_density_min         -0.862
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.209
_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)+4.4441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0918
_refine_special_details          
;
 There is reasonably high residual electron density close to the bromine atoms. 
 This has been attributed to the crystal not being completely single, however 
 it was not possible to model as a twin. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.51502(13) 0.55106(4) 0.33068(3) 0.02291(13) Uani 1 1 d . . . . .
C1 C 0.5170(11) 0.3865(4) 0.3700(3) 0.0156(8) Uani 1 1 d . . . . .
C2 C 0.6583(11) 0.3728(4) 0.4479(3) 0.0163(8) Uani 1 1 d . . . . .
H2 H 0.7487 0.4449 0.4801 0.020 Uiso 1 1 calc R . . . .
C3 C 0.6673(11) 0.2540(4) 0.4786(3) 0.0169(9) Uani 1 1 d . . . . .
H3 H 0.7655 0.2442 0.5317 0.020 Uiso 1 1 calc R . . . .
C4 C 0.5318(11) 0.1488(4) 0.4311(3) 0.0141(8) Uani 1 1 d . . . . .
C5 C 0.3947(11) 0.1641(4) 0.3521(3) 0.0162(8) Uani 1 1 d . . . . .
H5 H 0.3088 0.0924 0.3191 0.019 Uiso 1 1 calc R . . . .
C6 C 0.3843(11) 0.2835(4) 0.3221(3) 0.0166(9) Uani 1 1 d . . . . .
H6 H 0.2867 0.2943 0.2690 0.020 Uiso 1 1 calc R . . . .
C7 C 0.5387(11) 0.0198(4) 0.4621(3) 0.0155(8) Uani 1 1 d . . . . .
C8 C 0.6462(12) -0.0671(4) 0.4054(3) 0.0168(9) Uani 1 1 d . . . . .
N1 N 0.7432(12) -0.1293(4) 0.3580(3) 0.0261(9) Uani 1 1 d . . . . .
Br2 Br 0.18254(12) -0.05005(4) 0.84231(3) 0.01640(11) Uani 1 1 d . . . . .
C9 C 0.1270(11) 0.1122(4) 0.8801(3) 0.0128(8) Uani 1 1 d . . . . .
C10 C -0.0019(11) 0.1962(4) 0.8274(2) 0.0152(8) Uani 1 1 d . . . . .
H10 H -0.0695 0.1724 0.7727 0.018 Uiso 1 1 calc R . . . .
C11 C -0.0308(11) 0.3149(4) 0.8553(3) 0.0149(8) Uani 1 1 d . . . . .
H11 H -0.1155 0.3735 0.8194 0.018 Uiso 1 1 calc R . . . .
C12 C 0.0636(11) 0.3498(4) 0.9362(3) 0.0126(8) Uani 1 1 d . . . . .
C13 C 0.1904(11) 0.2626(4) 0.9881(3) 0.0142(8) Uani 1 1 d . . . . .
H13 H 0.2540 0.2851 1.0432 0.017 Uiso 1 1 calc R . . . .
C14 C 0.2240(11) 0.1444(4) 0.9603(3) 0.0139(8) Uani 1 1 d . . . . .
H14 H 0.3126 0.0858 0.9956 0.017 Uiso 1 1 calc R . . . .
C15 C 0.0356(11) 0.4808(4) 0.9625(2) 0.0123(8) Uani 1 1 d . . . . .
C16 C 0.1054(11) 0.5725(4) 0.8996(2) 0.0134(8) Uani 1 1 d . . . . .
N2 N 0.1697(11) 0.6397(4) 0.8475(2) 0.0200(8) 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
Br1 C1 1.891(4) . ?
C1 C2 1.387(6) . ?
C1 C6 1.377(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(6) . ?
C4 C5 1.402(6) . ?
C4 C7 1.485(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(6) . ?
C6 H6 0.9500 . ?
C7 C7 1.360(9) 2_656 ?
C7 C8 1.442(6) . ?
C8 N1 1.144(6) . ?
Br2 C9 1.899(4) . ?
C9 C10 1.387(6) . ?
C9 C14 1.384(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.400(6) . ?
C12 C13 1.399(6) . ?
C12 C15 1.496(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(6) . ?
C14 H14 0.9500 . ?
C15 C15 1.361(8) 2_567 ?
C15 C16 1.444(6) . ?
C16 N2 1.140(6) . ?

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 Br1 118.2(3) . . ?
C6 C1 Br1 120.6(3) . . ?
C6 C1 C2 121.2(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.7(4) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 C7 121.1(4) . . ?
C5 C4 C7 119.1(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.2(4) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C7 C7 C4 125.7(5) 2_656 . ?
C7 C7 C8 119.1(5) 2_656 . ?
C8 C7 C4 115.2(4) . . ?
N1 C8 C7 175.4(5) . . ?
C10 C9 Br2 120.0(3) . . ?
C14 C9 Br2 118.6(3) . . ?
C14 C9 C10 121.4(4) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(4) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C15 118.2(4) . . ?
C13 C12 C11 118.9(4) . . ?
C13 C12 C15 122.9(4) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 H14 120.4 . . ?
C13 C14 C9 119.1(4) . . ?
C13 C14 H14 120.4 . . ?
C15 C15 C12 126.9(5) 2_567 . ?
C15 C15 C16 119.5(5) 2_567 . ?
C16 C15 C12 113.5(3) . . ?
N2 C16 C15 175.8(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C3 -179.4(3) . . . . ?
Br1 C1 C6 C5 178.9(3) . . . . ?
C1 C2 C3 C4 -0.5(7) . . . . ?
C2 C1 C6 C5 -0.5(7) . . . . ?
C2 C3 C4 C5 1.5(7) . . . . ?
C2 C3 C4 C7 179.7(4) . . . . ?
C3 C4 C5 C6 -2.0(7) . . . . ?
C3 C4 C7 C7 42.7(8) . . . 2_656 ?
C3 C4 C7 C8 -135.7(4) . . . . ?
C4 C5 C6 C1 1.4(7) . . . . ?
C5 C4 C7 C7 -139.0(6) . . . 2_656 ?
C5 C4 C7 C8 42.6(6) . . . . ?
C6 C1 C2 C3 0.0(7) . . . . ?
C7 C4 C5 C6 179.8(4) . . . . ?
Br2 C9 C10 C11 -178.1(3) . . . . ?
Br2 C9 C14 C13 178.9(3) . . . . ?
C9 C10 C11 C12 -1.0(6) . . . . ?
C10 C9 C14 C13 0.2(6) . . . . ?
C10 C11 C12 C13 0.5(6) . . . . ?
C10 C11 C12 C15 178.4(4) . . . . ?
C11 C12 C13 C14 0.3(6) . . . . ?
C11 C12 C15 C15 149.3(6) . . . 2_567 ?
C11 C12 C15 C16 -32.9(5) . . . . ?
C12 C13 C14 C9 -0.7(6) . . . . ?
C13 C12 C15 C15 -32.8(8) . . . 2_567 ?
C13 C12 C15 C16 145.0(4) . . . . ?
C14 C9 C10 C11 0.6(7) . . . . ?
C15 C12 C13 C14 -177.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method Sublimation
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_testt1
_database_code_depnum_ccdc_archive 'CCDC 1568482'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-10-10 downloaded from the CCDC.
;
_audit_creation_date             2017-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        bis(4-bromophenyl)fumaronitrile
_chemical_formula_moiety         'C16 H8 Br2 N2'
_chemical_formula_sum            'C16 H8 Br2 N2'
_chemical_formula_weight         388.06
_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'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8318(2)
_cell_length_b                   9.3958(3)
_cell_length_c                   10.5371(3)
_cell_angle_alpha                87.814(2)
_cell_angle_beta                 70.8340(10)
_cell_angle_gamma                74.150(2)
_cell_volume                     703.43(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7426
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.60
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.751
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0661 before and 0.0277 after correction. The Ratio of minimum to maximum transmission is 0.7570. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.536
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.265
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12529
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.602
_diffrn_reflns_theta_min         2.257
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2985
_reflns_number_total             3262
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0188
_refine_ls_R_factor_gt           0.0161
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0205P)²+0.2715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0404
_refine_ls_wR_factor_ref         0.0412
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 -0.00508(2) 0.62303(2) 1.21997(2) 0.02035(5) Uani 1 1 d . . . . .
Br2 Br 1.23394(2) 0.02853(2) 0.06397(2) 0.01541(5) Uani 1 1 d . . . . .
N1 N 0.70782(19) 0.60060(15) 0.52996(14) 0.0217(3) Uani 1 1 d . . . . .
N2 N 0.46642(18) 0.06075(15) 0.73204(13) 0.0185(3) Uani 1 1 d . . . . .
C1 C 0.1791(2) 0.55398(17) 1.05023(15) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.1910(2) 0.64493(17) 0.94340(15) 0.0175(3) Uani 1 1 d . . . . .
H2 H 0.1079 0.7419 0.9545 0.021 Uiso 1 1 calc R . . . .
C3 C 0.3263(2) 0.59222(17) 0.81974(15) 0.0166(3) Uani 1 1 d . . . . .
H3 H 0.3364 0.6540 0.7456 0.020 Uiso 1 1 calc R . . . .
C4 C 0.44812(19) 0.44933(16) 0.80291(14) 0.0126(3) Uani 1 1 d . . . . .
C5 C 0.4357(2) 0.36140(16) 0.91312(15) 0.0143(3) Uani 1 1 d . . . . .
H5 H 0.5203 0.2652 0.9034 0.017 Uiso 1 1 calc R . . . .
C6 C 0.3003(2) 0.41342(16) 1.03712(15) 0.0154(3) Uani 1 1 d . . . . .
H6 H 0.2912 0.3530 1.1121 0.018 Uiso 1 1 calc R . . . .
C7 C 0.58837(19) 0.39342(16) 0.66957(14) 0.0130(3) Uani 1 1 d . . . . .
C8 C 0.6629(2) 0.50409(17) 0.58878(15) 0.0156(3) Uani 1 1 d . . . . .
C9 C 0.64157(19) 0.25234(16) 0.61635(14) 0.0124(3) Uani 1 1 d . . . . .
C10 C 0.5410(2) 0.14855(16) 0.68498(14) 0.0137(3) Uani 1 1 d . . . . .
C11 C 0.7897(2) 0.19339(16) 0.48665(14) 0.0129(3) Uani 1 1 d . . . . .
C12 C 0.9609(2) 0.22948(16) 0.44774(15) 0.0145(3) Uani 1 1 d . . . . .
H12 H 0.9849 0.2903 0.5062 0.017 Uiso 1 1 calc R . . . .
C13 C 1.0960(2) 0.17637(16) 0.32352(15) 0.0144(3) Uani 1 1 d . . . . .
H13 H 1.2130 0.1996 0.2971 0.017 Uiso 1 1 calc R . . . .
C14 C 1.0582(2) 0.08936(16) 0.23890(14) 0.0131(3) Uani 1 1 d . . . . .
C15 C 0.8919(2) 0.04857(16) 0.27687(15) 0.0143(3) Uani 1 1 d . . . . .
H15 H 0.8693 -0.0131 0.2183 0.017 Uiso 1 1 calc R . . . .
C16 C 0.7592(2) 0.09951(16) 0.40186(15) 0.0145(3) Uani 1 1 d . . . . .
H16 H 0.6461 0.0702 0.4302 0.017 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
Br1 C1 1.8932(14) . ?
Br2 C14 1.8981(14) . ?
N1 C8 1.148(2) . ?
N2 C10 1.144(2) . ?
C1 C2 1.381(2) . ?
C1 C6 1.381(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(2) . ?
C4 C5 1.392(2) . ?
C4 C7 1.4780(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.444(2) . ?
C7 C9 1.359(2) . ?
C9 C10 1.444(2) . ?
C9 C11 1.4786(19) . ?
C11 C12 1.3991(19) . ?
C11 C16 1.396(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.391(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(2) . ?
C14 C15 1.387(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(2) . ?
C16 H16 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
C2 C1 Br1 119.70(11) . . ?
C2 C1 C6 121.60(13) . . ?
C6 C1 Br1 118.69(11) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.86(14) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.73(14) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C7 120.06(13) . . ?
C5 C4 C3 119.12(13) . . ?
C5 C4 C7 120.82(13) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.40(13) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.24(13) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C8 C7 C4 115.07(13) . . ?
C9 C7 C4 125.71(13) . . ?
C9 C7 C8 119.09(13) . . ?
N1 C8 C7 174.20(16) . . ?
C7 C9 C10 119.33(13) . . ?
C7 C9 C11 126.01(13) . . ?
C10 C9 C11 114.56(12) . . ?
N2 C10 C9 175.69(16) . . ?
C12 C11 C9 121.02(13) . . ?
C16 C11 C9 119.63(13) . . ?
C16 C11 C12 119.35(13) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.03(13) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.32(13) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 Br2 119.59(11) . . ?
C13 C14 C15 121.67(13) . . ?
C15 C14 Br2 118.71(11) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.74(13) . . ?
C16 C15 H15 120.6 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.78(13) . . ?
C15 C16 H16 119.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane, methanol atmosphere'
_exptl_crystal_preparation       Luminescent
