#------------------------------------------------------------------------------
#$Date: 2019-04-26 05:36:49 +0300 (Fri, 26 Apr 2019) $
#$Revision: 214795 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/29/2242921.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2242921
loop_
_publ_author_name
'Noland, Wayland E.'
'Schneerer, Andrew K.'
'Raberge, Emilie J.'
'Tritch, Kenneth J.'
_publ_section_title
;
 Crystal structure of 2,3,5,6-tetrabromoterephthalodinitrile
;
_journal_coeditor_code           HB7811
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              703
_journal_page_last               706
_journal_paper_doi               10.1107/S2056989019005486
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C8 Br4 N2'
_chemical_formula_moiety         'C8 Br4 N2'
_chemical_formula_sum            'C8 Br4 N2'
_chemical_formula_weight         443.74
_chemical_melting_point          603
_chemical_name_common            BR4TN
_chemical_name_systematic
;
2,3,5,6-Tetrabromoterephthalonitrile
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90.202(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8500(6)
_cell_length_b                   9.8330(8)
_cell_length_c                   6.7540(6)
_cell_measurement_reflns_used    2993
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.42
_cell_measurement_theta_min      3.02
_cell_volume                     521.33(7)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON-II area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3324
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.560
_diffrn_reflns_theta_min         3.016
_diffrn_source                   micro-focus
_exptl_absorpt_coefficient_mu    15.396
_exptl_absorpt_correction_T_max  0.4935
_exptl_absorpt_correction_T_min  0.2534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.827
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.085
_refine_diff_density_min         -1.008
_refine_ls_extinction_coef       0.0029(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018/3 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     38
_refine_ls_number_reflns         837
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0175P)²+0.7909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0723
_reflns_number_gt                741
_reflns_number_total             837
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7811sup1.cif
_cod_data_source_block           I
_cod_database_code               2242921
_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.
;
_shelx_estimated_absorpt_t_min   0.206
_shelx_estimated_absorpt_t_max   0.655
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'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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_occupancy
Br Br1 0.40138(3) 0.78605(3) 0.77786(4) 0.01672(15) Uani d 1
N N1 0.2553(5) 0.500000 0.4857(5) 0.0219(7) Uani d 1
C C1 0.3260(5) 0.500000 0.6333(6) 0.0158(7) Uani d 1
C C2 0.4158(5) 0.500000 0.8209(6) 0.0148(7) Uani d 1
C C3 0.4576(3) 0.6237(3) 0.9090(4) 0.0142(5) Uani d 1
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'
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'
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
N1 C1 C2 . . 180.0(4)
C3 C2 C3 . 6_565 121.7(3)
C3 C2 C1 . . 119.17(17)
C3 C2 C1 6_565 . 119.17(17)
C2 C3 C3 . 2_657 119.17(17)
C2 C3 Br1 . . 119.1(2)
C3 C3 Br1 2_657 . 121.75(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C3 . 1.878(3)
N1 C1 . 1.139(5)
C1 C2 . 1.448(5)
C2 C3 . 1.393(3)
C2 C3 6_565 1.393(3)
C3 C3 2_657 1.395(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_4
_geom_torsion
C3 C2 C3 C3 6_565 2_657 -0.5(6)
C1 C2 C3 C3 . 2_657 179.2(3)
C3 C2 C3 Br1 6_565 . 178.56(19)
C1 C2 C3 Br1 . . -1.7(4)

_cod_database_fobs_code 2242921
