# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2023

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1852922'
loop_
_audit_author_name
_audit_author_address
'Yunus Zorlu' 'Gebze Technical University'
_audit_update_record             
;
2018-07-02 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Phthalonitrile
_chemical_formula_moiety         'C10 H4 Br4 N2'
_chemical_formula_sum            'C10 H4 Br4 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         471.79
_chemical_absolute_configuration ?

_chemical_melting_point          ?

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

_cell_length_a                   7.9676(7)
_cell_length_b                   8.5676(7)
_cell_length_c                   9.6639(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.119(5)
_cell_angle_gamma                90
_cell_volume                     636.85(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    109
_cell_measurement_theta_min      2.1757
_cell_measurement_theta_max      19.9660
_cell_measurement_temperature    176.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_crystal_density_diffrn    2.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436

_exptl_absorpt_coefficient_mu    12.611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.06
_exptl_absorpt_correction_T_max  0.21

_exptl_special_details           
;
;

_diffrn_ambient_temperature      176.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            7210
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             2232
_reflns_number_gt                1918
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1011
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.054
_refine_ls_number_reflns         2232
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²+0.8920P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.125
_refine_diff_density_min         -0.611
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 776 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.058(16)

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'

_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 -0.02249(17) 0.87936(14) 0.79289(14) 0.0483(4) Uani d . . . 1 . .
Br Br2 -0.15766(17) 0.68352(16) 0.50292(14) 0.0570(4) Uani d . . . 1 . .
Br Br3 0.45895(18) 0.89086(15) 0.73426(15) 0.0528(4) Uani d . . . 1 . .
Br Br4 0.3118(2) 0.71084(16) 0.43937(13) 0.0574(4) Uani d . . . 1 . .
C C1 0.2371(14) 0.2108(14) 0.9544(11) 0.033(2) Uani d . . . 1 . .
C C2 0.5473(15) 0.2834(13) 0.8726(11) 0.034(3) Uani d . . . 1 . .
C C3 0.3954(13) 0.3818(14) 0.8303(11) 0.033(2) Uani d . . . 1 . .
C C4 0.4006(15) 0.5138(13) 0.7473(11) 0.032(2) Uani d . . . 1 . .
H H4 0.5026 0.5361 0.7175 0.038 Uiso calc U . R 1 . .
C C5 0.2567(13) 0.6141(12) 0.7072(10) 0.027(2) Uani d . . . 1 . .
C C6 0.1063(13) 0.5767(12) 0.7454(10) 0.029(2) Uani d . . . 1 . .
C C7 0.0999(14) 0.4440(13) 0.8268(11) 0.031(2) Uani d . . . 1 . .
H H7 -0.004 0.4194 0.8529 0.037 Uiso calc U . R 1 . .
C C8 0.2447(14) 0.3465(11) 0.8704(11) 0.030(2) Uani d . . . 1 . .
C C9 -0.0578(14) 0.6717(13) 0.7100(11) 0.036(3) Uani d . . . 1 . .
H H9 -0.1438 0.617 0.7521 0.043 Uiso calc U . R 1 . .
C C10 0.2756(15) 0.7591(13) 0.6224(11) 0.035(3) Uani d . . . 1 . .
H H10 0.1643 0.8189 0.6054 0.042 Uiso calc U . R 1 . .
N N1 0.2300(16) 0.1055(13) 1.0261(12) 0.051(3) Uani d . . . 1 . .
N N2 0.6626(14) 0.2021(13) 0.9072(12) 0.052(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C9 . 1.942(11) ?
Br2 C9 . 1.953(10) ?
Br3 C10 . 1.938(10) ?
Br4 C10 . 1.910(11) ?
C1 N1 . 1.147(14) ?
C1 C8 . 1.428(15) ?
C2 N2 . 1.132(15) ?
C2 C3 . 1.444(15) ?
C3 C8 . 1.388(15) ?
C3 C4 . 1.393(16) ?
C4 C5 . 1.404(15) ?
C4 H4 . 0.95 ?
C5 C6 . 1.380(14) ?
C5 C10 . 1.517(14) ?
C6 C7 . 1.391(15) ?
C6 C9 . 1.502(15) ?
C7 C8 . 1.398(15) ?
C7 H7 . 0.95 ?
C9 H9 . 1.0 ?
C10 H10 . 1.0 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C8 . . 177.3(11) ?
N2 C2 C3 . . 177.4(13) ?
C8 C3 C4 . . 119.7(10) ?
C8 C3 C2 . . 121.1(10) ?
C4 C3 C2 . . 119.2(10) ?
C3 C4 C5 . . 120.7(10) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C6 C5 C4 . . 119.2(9) ?
C6 C5 C10 . . 123.3(9) ?
C4 C5 C10 . . 117.5(10) ?
C5 C6 C7 . . 120.2(10) ?
C5 C6 C9 . . 125.4(9) ?
C7 C6 C9 . . 114.4(10) ?
C6 C7 C8 . . 120.7(11) ?
C6 C7 H7 . . 119.7 ?
C8 C7 H7 . . 119.7 ?
C3 C8 C7 . . 119.4(10) ?
C3 C8 C1 . . 120.3(10) ?
C7 C8 C1 . . 120.3(10) ?
C6 C9 Br1 . . 112.2(7) ?
C6 C9 Br2 . . 111.1(7) ?
Br1 C9 Br2 . . 110.6(5) ?
C6 C9 H9 . . 107.6 ?
Br1 C9 H9 . . 107.6 ?
Br2 C9 H9 . . 107.6 ?
C5 C10 Br4 . . 112.5(8) ?
C5 C10 Br3 . . 110.0(7) ?
Br4 C10 Br3 . . 111.6(6) ?
C5 C10 H10 . . 107.5 ?
Br4 C10 H10 . . 107.5 ?
Br3 C10 H10 . . 107.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 C3 C4 C5 . . . . 1.8(15) ?
C2 C3 C4 C5 . . . . -178.4(9) ?
C3 C4 C5 C6 . . . . -3.0(15) ?
C3 C4 C5 C10 . . . . 177.4(10) ?
C4 C5 C6 C7 . . . . 2.1(15) ?
C10 C5 C6 C7 . . . . -178.2(9) ?
C4 C5 C6 C9 . . . . -179.7(9) ?
C10 C5 C6 C9 . . . . -0.1(16) ?
C5 C6 C7 C8 . . . . -0.2(15) ?
C9 C6 C7 C8 . . . . -178.6(9) ?
C4 C3 C8 C7 . . . . 0.1(15) ?
C2 C3 C8 C7 . . . . -179.6(9) ?
C4 C3 C8 C1 . . . . 179.4(9) ?
C2 C3 C8 C1 . . . . -0.3(15) ?
C6 C7 C8 C3 . . . . -0.9(15) ?
C6 C7 C8 C1 . . . . 179.8(9) ?
C5 C6 C9 Br1 . . . . -61.2(12) ?
C7 C6 C9 Br1 . . . . 117.0(9) ?
C5 C6 C9 Br2 . . . . 63.1(12) ?
C7 C6 C9 Br2 . . . . -118.7(9) ?
C6 C5 C10 Br4 . . . . -116.0(10) ?
C4 C5 C10 Br4 . . . . 63.7(10) ?
C6 C5 C10 Br3 . . . . 118.8(10) ?
C4 C5 C10 Br3 . . . . -61.5(11) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C9 H9 N1 2_557 1.00 2.42 3.247(16) 139.8 ?
C10 H10 Br1 . 1.00 2.68 3.385(13) 127.8 ?
C10 H10 Br2 . 1.00 2.75 3.404(11) 123.1 ?

####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1852923'
loop_
_audit_author_name
_audit_author_address
'Yunus Zorlu' 'Gebze Technical University'
_audit_update_record             
;
2018-07-02 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'organic compound'
_chemical_formula_moiety         '	C10 H4 Br4 N2'
_chemical_formula_sum            'C10 H4 Br4 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         471.79

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   6.2037(7)
_cell_length_b                   6.6476(8)
_cell_length_c                   15.677(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.856(9)
_cell_angle_gamma                90
_cell_volume                     643.14(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    115
_cell_measurement_theta_min      4.5212
_cell_measurement_theta_max      22.1227
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.142
_exptl_crystal_density_diffrn    2.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436

_exptl_absorpt_coefficient_mu    12.487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.13
_exptl_absorpt_correction_T_max  0.27

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            3469
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             1107
_reflns_number_gt                942
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0696
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_number_reflns         1107
_refine_ls_number_parameters     73
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0242P)²+1.0714P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.534
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL V6.14 (Bruker AXS)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.09526(8) 0.67820(8) 0.29976(3) 0.05548(19) Uani d . . . 1 . .
Br Br2 0.49988(9) 0.96712(8) 0.33052(4) 0.0598(2) Uani d . . . 1 . .
C C3 0.4058(6) 0.6498(5) 0.4444(3) 0.0309(9) Uani d . . . 1 . .
C C4 0.5834(6) 0.5417(6) 0.4235(3) 0.0339(9) Uani d . . . 1 . .
H H4 0.6409 0.5676 0.3721 0.041 Uiso calc U . R 1 . .
C C5 0.6767(6) 0.3948(6) 0.4785(3) 0.0311(9) Uani d . . . 1 . .
C C8 0.8665(7) 0.2900(6) 0.4552(3) 0.0378(10) Uani d . . . 1 . .
C C10 0.2966(7) 0.8066(6) 0.3863(3) 0.0368(10) Uani d . . . 1 . .
H H10 0.2143 0.8959 0.4207 0.044 Uiso calc U . R 1 . .
N N2 1.0177(7) 0.2098(6) 0.4380(3) 0.0550(11) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C10 . 1.945(4) ?
Br2 C10 . 1.928(4) ?
C3 C4 . 1.382(5) ?
C3 C5 3_666 1.391(5) ?
C3 C10 . 1.499(5) ?
C4 C5 . 1.390(6) ?
C4 H4 . 0.93 ?
C5 C3 3_666 1.391(5) ?
C5 C8 . 1.446(5) ?
C8 N2 . 1.135(5) ?
C10 H10 . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 C3 C5 . 3_666 117.9(4) ?
C4 C3 C10 . . 122.6(4) ?
C5 C3 C10 3_666 . 119.5(3) ?
C3 C4 C5 . . 120.6(4) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C4 C5 C3 . 3_666 121.5(3) ?
C4 C5 C8 . . 118.7(4) ?
C3 C5 C8 3_666 . 119.9(4) ?
N2 C8 C5 . . 178.7(5) ?
C3 C10 Br2 . . 112.6(3) ?
C3 C10 Br1 . . 109.7(3) ?
Br2 C10 Br1 . . 109.2(2) ?
C3 C10 H10 . . 108.4 ?
Br2 C10 H10 . . 108.4 ?
Br1 C10 H10 . . 108.4 ?

####################################################################### 
# 
# 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_I_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1852924'
loop_
_audit_author_name
_audit_author_address
'Yunus Zorlu' 'Gebze Technical University'
_audit_update_record             
;
2018-07-02 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'Organic compound'
_chemical_formula_moiety         '	C10 H4 Br4 N2'
_chemical_formula_sum            'C10 H4 Br4 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         471.79

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.7944(13)
_cell_length_b                   9.9395(12)
_cell_length_c                   13.1845(19)
_cell_angle_alpha                90
_cell_angle_beta                 97.554(9)
_cell_angle_gamma                90
_cell_volume                     1272.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    86
_cell_measurement_theta_min      4.3864
_cell_measurement_theta_max      22.0762
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.284
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.128
_exptl_crystal_density_diffrn    2.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872

_exptl_absorpt_coefficient_mu    12.624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.11
_exptl_absorpt_correction_T_max  0.29

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            5476
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0937
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             2248
_reflns_number_gt                1541
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1322
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_number_reflns         2248
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0323P)²+1.8884P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.813
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL V6.14 (Bruker AXS)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.34749(9) 0.30339(8) 0.15366(7) 0.0480(3) Uani d . . . 1 . .
Br Br2 0.11429(9) 0.52969(10) 0.14266(9) 0.0618(3) Uani d . . . 1 . .
Br Br3 0.83721(8) 0.80637(9) 0.12029(7) 0.0491(3) Uani d . . . 1 . .
Br Br4 0.61452(9) 1.03971(8) 0.13742(7) 0.0473(3) Uani d . . . 1 . .
C C1 0.3574(9) 0.4960(8) 0.3529(6) 0.043(2) Uani d . . . 1 . .
C C2 0.7003(9) 0.8429(8) 0.3383(6) 0.038(2) Uani d . . . 1 . .
C C3 0.5977(7) 0.7588(7) 0.2819(6) 0.0297(18) Uani d . . . 1 . .
C C4 0.5266(8) 0.6721(7) 0.3389(6) 0.0351(19) Uani d . . . 1 . .
H H4 0.5443 0.6722 0.4099 0.042 Uiso calc U . R 1 . .
C C5 0.4293(8) 0.5855(7) 0.2893(6) 0.0299(18) Uani d . . . 1 . .
C C6 0.4011(7) 0.5832(7) 0.1834(5) 0.0276(17) Uani d . . . 1 . .
C C7 0.4734(7) 0.6743(7) 0.1292(6) 0.0285(17) Uani d . . . 1 . .
H H7 0.4547 0.676 0.0582 0.034 Uiso calc U . R 1 . .
C C8 0.5689(7) 0.7598(7) 0.1759(6) 0.0287(17) Uani d . . . 1 . .
C C9 0.6430(7) 0.8515(7) 0.1097(6) 0.0314(18) Uani d . . . 1 . .
H H9 0.6033 0.8352 0.0386 0.038 Uiso calc U . R 1 . .
C C10 0.3021(7) 0.4908(7) 0.1223(6) 0.0338(18) Uani d . . . 1 . .
H H10 0.31 0.5056 0.0499 0.041 Uiso calc U . R 1 . .
N N1 0.3048(9) 0.4299(8) 0.4067(6) 0.067(3) Uani d . . . 1 . .
N N2 0.7810(8) 0.9072(7) 0.3845(6) 0.053(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C10 . 1.947(7) ?
Br2 C10 . 1.932(7) ?
Br3 C9 . 1.941(7) ?
Br4 C9 . 1.933(7) ?
C1 N1 . 1.138(9) ?
C1 C5 . 1.465(10) ?
C2 N2 . 1.130(10) ?
C2 C3 . 1.437(11) ?
C3 C4 . 1.389(9) ?
C3 C8 . 1.389(10) ?
C4 C5 . 1.382(10) ?
C4 H4 . 0.93 ?
C5 C6 . 1.387(10) ?
C6 C7 . 1.402(9) ?
C6 C10 . 1.492(10) ?
C7 C8 . 1.351(10) ?
C7 H7 . 0.93 ?
C8 C9 . 1.512(8) ?
C9 H9 . 0.98 ?
C10 H10 . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C5 . . 176.4(9) ?
N2 C2 C3 . . 178.4(9) ?
C4 C3 C8 . . 119.9(7) ?
C4 C3 C2 . . 116.6(7) ?
C8 C3 C2 . . 123.5(6) ?
C5 C4 C3 . . 119.6(7) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
C4 C5 C6 . . 121.3(6) ?
C4 C5 C1 . . 117.4(7) ?
C6 C5 C1 . . 121.2(7) ?
C5 C6 C7 . . 117.1(7) ?
C5 C6 C10 . . 125.7(6) ?
C7 C6 C10 . . 117.3(6) ?
C8 C7 C6 . . 122.7(7) ?
C8 C7 H7 . . 118.7 ?
C6 C7 H7 . . 118.7 ?
C7 C8 C3 . . 119.4(6) ?
C7 C8 C9 . . 118.2(7) ?
C3 C8 C9 . . 122.4(7) ?
C8 C9 Br4 . . 112.5(5) ?
C8 C9 Br3 . . 111.0(5) ?
Br4 C9 Br3 . . 112.0(3) ?
C8 C9 H9 . . 107.0 ?
Br4 C9 H9 . . 107.0 ?
Br3 C9 H9 . . 107.0 ?
C6 C10 Br2 . . 111.4(5) ?
C6 C10 Br1 . . 111.1(5) ?
Br2 C10 Br1 . . 110.9(3) ?
C6 C10 H10 . . 107.7 ?
Br2 C10 H10 . . 107.7 ?
Br1 C10 H10 . . 107.7 ?

