# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2077700'
loop_
_audit_author_name
_audit_author_address
'Kumar Biradha'
;Indian Institute of Technology Kharagpur
India
;
_audit_update_record             
;
2021-04-15 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H4 Br4 N2'
_chemical_formula_weight         423.75

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.1485(12)
_cell_length_b                   4.1785(4)
_cell_length_c                   17.4426(14)
_cell_angle_alpha                90
_cell_angle_beta                 109.847(4)
_cell_angle_gamma                90
_cell_volume                     969.95(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2148
_cell_measurement_theta_min      2.434
_cell_measurement_theta_max      27.139

_exptl_crystal_description       Needle
_exptl_crystal_colour            'oragne red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.902
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   0.064
_exptl_transmission_factor_max   0.137
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    16.541
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 CCD Detector'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40895
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.434
_diffrn_reflns_theta_max         27.139
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2148
_reflns_number_gt                1974
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2148
_refine_ls_number_parameters     125
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1540
_refine_ls_wR_factor_gt          0.1502
_refine_ls_goodness_of_fit_ref   1.342
_refine_ls_restrained_S_all      1.344
_refine_ls_shift/su_max          0.011
_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 0.12082(5) 0.40678(15) 0.07838(3) 0.0530(2) Uani 1 1 d . . . . .
Br2 Br 0.15282(4) 0.61964(13) 0.40606(3) 0.0451(2) Uani 1 1 d . . . . .
Br3 Br 0.37341(4) 0.24681(15) 0.46658(3) 0.0505(2) Uani 1 1 d . . . . .
Br4 Br 0.46408(4) -0.04321(13) 0.33010(3) 0.0444(2) Uani 1 1 d . . . . .
N1 N 0.3241(3) 0.0707(11) 0.1555(3) 0.0402(10) Uani 1 1 d D . . . .
H2N1 H 0.279(4) 0.069(15) 0.108(2) 0.056(19) Uiso 1 1 d D . . . .
H2N2 H 0.037(3) 0.701(11) 0.1699(13) 0.020(11) Uiso 1 1 d D . . . .
N2 N 0.0625(3) 0.6542(11) 0.2214(3) 0.0394(9) Uani 1 1 d D . . . .
H1N1 H 0.370(4) -0.073(11) 0.162(4) 0.051(17) Uiso 1 1 d D . . . .
H1N2 H 0.038(4) 0.804(10) 0.246(3) 0.040(15) Uiso 1 1 d D . . . .
C1 C 0.2851(3) 0.1945(11) 0.2136(3) 0.0324(9) Uani 1 1 d . . . . .
C2 C 0.1946(3) 0.3645(11) 0.1915(3) 0.0322(9) Uani 1 1 d . . . . .
C3 C 0.1546(3) 0.4990(10) 0.2468(3) 0.0315(9) Uani 1 1 d . . . . .
C4 C 0.2079(3) 0.4562(10) 0.3292(3) 0.0312(9) Uani 1 1 d . . . . .
C5 C 0.3000(3) 0.2942(11) 0.3552(3) 0.0322(9) Uani 1 1 d . . . . .
C6 C 0.3382(3) 0.1670(11) 0.2977(3) 0.0321(9) Uani 1 1 d . . . . .

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 0.0547(4) 0.0707(4) 0.0272(4) 0.0049(2) 0.0056(3) 0.0024(3)
Br2 0.0485(4) 0.0528(4) 0.0389(4) -0.0068(2) 0.0211(3) 0.0026(2)
Br3 0.0469(4) 0.0682(4) 0.0294(4) 0.0029(2) 0.0040(3) 0.0047(2)
Br4 0.0350(3) 0.0505(4) 0.0481(4) 0.0083(2) 0.0146(3) 0.0081(2)
N1 0.031(2) 0.052(2) 0.040(3) 0.0052(19) 0.015(2) 0.0029(17)
N2 0.035(2) 0.045(2) 0.036(2) 0.0082(19) 0.0091(19) 0.0065(17)
C1 0.034(2) 0.034(2) 0.030(2) 0.0005(18) 0.0123(18) -0.0087(17)
C2 0.033(2) 0.040(2) 0.021(2) 0.0056(17) 0.0060(17) -0.0052(17)
C3 0.029(2) 0.0287(19) 0.037(3) 0.0066(18) 0.0110(19) -0.0013(15)
C4 0.033(2) 0.034(2) 0.028(2) -0.0028(17) 0.0113(19) -0.0034(17)
C5 0.033(2) 0.036(2) 0.025(2) 0.0032(17) 0.0053(17) -0.0024(17)
C6 0.029(2) 0.0352(19) 0.033(2) 0.0062(18) 0.0107(18) 0.0004(17)

_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 C2 1.902(4) . ?
Br2 C4 1.893(5) . ?
Br3 C5 1.876(5) . ?
Br4 C6 1.892(4) . ?
N1 C1 1.407(6) . ?
N2 C3 1.386(6) . ?
C1 C6 1.408(7) . ?
C1 C2 1.400(7) . ?
C2 C3 1.392(7) . ?
C3 C4 1.388(7) . ?
C4 C5 1.400(6) . ?
C5 C6 1.396(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
C6 C1 C2 116.2(4) . . ?
C6 C1 N1 121.4(4) . . ?
C2 C1 N1 122.3(4) . . ?
C3 C2 C1 124.3(4) . . ?
C3 C2 Br1 118.2(3) . . ?
C1 C2 Br1 117.5(3) . . ?
C4 C3 N2 120.8(4) . . ?
C4 C3 C2 117.3(4) . . ?
N2 C3 C2 121.7(4) . . ?
C3 C4 C5 121.1(4) . . ?
C3 C4 Br2 118.5(3) . . ?
C5 C4 Br2 120.4(4) . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 Br3 120.9(4) . . ?
C6 C5 Br3 119.4(3) . . ?
C1 C6 C5 121.3(4) . . ?
C1 C6 Br4 117.6(3) . . ?
C5 C6 Br4 121.1(3) . . ?

_refine_diff_density_max         1.069
_refine_diff_density_min         -1.383
_refine_diff_density_rms         0.328

_shelx_res_file                  
;

    kb.res created by SHELXL-2014/7


TITL kb in P2(1)/c
CELL 0.71073  14.14846   4.17850  17.44260  90.0000 109.8465  90.0000
ZERR    4.00   0.00117   0.00040   0.00140   0.0000   0.0037   0.0000
LATT  1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C H N BR
UNIT 24 16 8 16
TEMP 23.000

L.S. 20
BOND
FMAP 2
ACTA
PLAN 20
DFIX N1 H1N1 0.9
DFIX N1 H2N1 0.9
DFIX N2 H1N2 0.9
DFIX N2 H2N2 0.9
WGHT    0.100000
FVAR       0.10802
BR1   4    0.120821    0.406775    0.078381    11.00000    0.05470    0.07072 =
         0.02719    0.00492    0.00563    0.00238
BR2   4    0.152824    0.619639    0.406063    11.00000    0.04852    0.05275 =
         0.03891   -0.00681    0.02112    0.00259
BR3   4    0.373409    0.246812    0.466576    11.00000    0.04694    0.06824 =
         0.02936    0.00285    0.00397    0.00474
BR4   4    0.464076   -0.043212    0.330097    11.00000    0.03499    0.05047 =
         0.04814    0.00834    0.01463    0.00810
N1    3    0.324141    0.070705    0.155472    11.00000    0.03123    0.05155 =
         0.03975    0.00520    0.01458    0.00291
H2N1  2    0.279204    0.068941    0.107748    11.00000    0.05568
H2N2  2    0.037003    0.701295    0.169896    11.00000    0.01970
N2    3    0.062524    0.654195    0.221409    11.00000    0.03495    0.04499 =
         0.03605    0.00819    0.00915    0.00655
H1N1  2    0.369642   -0.073147    0.161744    11.00000    0.05137
H1N2  2    0.038461    0.804301    0.246350    11.00000    0.04035
C1    1    0.285126    0.194457    0.213592    11.00000    0.03377    0.03419 =
         0.03046    0.00049    0.01230   -0.00866
C2    1    0.194581    0.364527    0.191512    11.00000    0.03298    0.04015 =
         0.02091    0.00557    0.00598   -0.00521
C3    1    0.154585    0.499048    0.246839    11.00000    0.02861    0.02870 =
         0.03714    0.00663    0.01100   -0.00130
C4    1    0.207897    0.456244    0.329173    11.00000    0.03252    0.03351 =
         0.02844   -0.00276    0.01133   -0.00340
C5    1    0.300003    0.294221    0.355242    11.00000    0.03296    0.03570 =
         0.02459    0.00320    0.00526   -0.00243
C6    1    0.338160    0.167032    0.297727    11.00000    0.02856    0.03517 =
         0.03271    0.00618    0.01068    0.00038

HKLF 4

REM  kb in P2(1)/c
REM R1 =  0.0490 for    1974 Fo > 4sig(Fo)  and  0.0524 for all    2148 data
REM    125 parameters refined using      4 restraints

END

WGHT      0.1198      0.8963

REM Highest difference peak  1.069,  deepest hole -1.383,  1-sigma level  0.328
Q1    1   0.3202 -0.0061  0.1250  11.00000  0.05    1.07
Q2    1   0.4092 -0.1784  0.5536  11.00000  0.05    0.96
Q3    1   0.0634  0.8665  0.1659  11.00000  0.05    0.92
Q4    1   0.1320  0.8840  0.1626  11.00000  0.05    0.89
Q5    1   0.3460  0.7073  0.3781  11.00000  0.05    0.86
Q6    1   0.0349  0.7234  0.4218  11.00000  0.05    0.86
Q7    1   0.4137  0.3356  0.4210  11.00000  0.05    0.86
Q8    1   0.2998  0.1881  0.2551  11.00000  0.05    0.80
Q9    1   0.1807  0.3549 -0.0089  11.00000  0.05    0.80
Q10   1  -0.0411  0.6462  0.1887  11.00000  0.05    0.78
Q11   1   0.1690  0.2809  0.4832  11.00000  0.05    0.77
Q12   1   0.3427 -0.3212  0.0771  11.00000  0.05    0.77
Q13   1   0.1443  0.2179  0.0158  11.00000  0.05    0.75
Q14   1   0.4988 -0.1799  0.2707  11.00000  0.05    0.73
Q15   1   0.4540 -0.2633  0.3872  11.00000  0.05    0.72
Q16   1   0.5078  0.4516  0.4189  11.00000  0.05    0.71
Q17   1   0.2082  0.1431  0.3174  11.00000  0.05    0.71
Q18   1   0.3706  0.0427  0.1799  11.00000  0.05    0.69
Q19   1   0.1222  0.7195  0.1492  11.00000  0.05    0.68
Q20   1   0.0819  0.7219  0.1926  11.00000  0.05    0.67
;
_shelx_res_checksum              40157
