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#$Date: 2019-12-25 22:52:39 +0200 (Wed, 25 Dec 2019) $
#$Revision: 245963 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/15/2311534.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_2311534
loop_
_publ_author_name
'Noland, Wayland E.'
'Shudy, Jessica E.'
'Rieger, Janel L.'
'Tu, Zoe H.'
'Tritch, Kenneth J.'
_publ_section_title
;
 Crystal structures of 2,6-di-bromo-4-methyl-benzo-nitrile and
 2,6-di-bromo-4-methyl-phenyl isocyanide.
;
_journal_coeditor_code           LH5859
_journal_issue                   'Pt 12'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1913
_journal_page_last               1916
_journal_paper_doi               10.1107/S2056989017016395
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C8 H5 Br2 N'
_chemical_formula_moiety         'C8 H5 Br2 N'
_chemical_formula_sum            'C8 H5 Br2 N'
_chemical_formula_weight         274.95
_chemical_melting_point          434
_chemical_name_common            RCN
_chemical_name_systematic
;
3,5-Dibromo-4-methylbenzonitrile
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           113
_space_group_name_Hall           'P -4 2ab'
_space_group_name_H-M_alt        'P -4 21 m'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6731(5)
_cell_length_b                   14.6731(5)
_cell_length_c                   3.97270(10)
_cell_measurement_reflns_used    2980
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      74.01
_cell_measurement_theta_min      4.26
_cell_volume                     855.32(5)
_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
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Venture PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            8444
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.241
_diffrn_reflns_theta_min         6.032
_exptl_absorpt_coefficient_mu    11.456
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.3135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.135
_exptl_crystal_description       Needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.316
_refine_ls_abs_structure_details
;
Flack x determined using 348 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_coef       0.0055(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.270
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.270
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0201
_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)+2.1952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0571
_refine_ls_wR_factor_ref         0.0571
_reflns_number_gt                902
_reflns_number_total             904
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5859sup1.cif
_cod_data_source_block           RCN
_cod_original_cell_volume        855.32(6)
_cod_database_code               2311534
_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   0.069
_shelx_estimated_absorpt_t_max   0.690
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-y+1/2, -x+1/2, z'
'y+1/2, x+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
C C1 0.2722(3) 0.7722(3) 0.357(2) 0.0156(13) Uani d 1
C C2 0.2985(3) 0.6837(4) 0.2695(13) 0.0177(10) Uani d 1
Br Br2 0.41762(3) 0.64354(3) 0.38319(19) 0.0222(2) Uani d 1
C C3 0.2404(3) 0.6240(3) 0.1067(15) 0.0185(9) Uani d 1
H H3A 0.2605 0.5645 0.0486 0.022 Uiso calc 1
C C4 0.1517(3) 0.6517(3) 0.0283(18) 0.0189(15) Uani d 1
C C5 0.3328(4) 0.8328(4) 0.532(2) 0.0223(17) Uani d 1
N N1 0.3806(3) 0.8806(3) 0.676(2) 0.0309(17) Uani d 1
C C6 0.0866(3) 0.5866(3) -0.138(2) 0.0212(13) Uani d 1
H H6A 0.0306 0.6190 -0.1991 0.032 Uiso calc 0.5
H H6B 0.0720 0.5369 0.0175 0.032 Uiso calc 0.5
H H6C 0.1148 0.5615 -0.3417 0.032 Uiso calc 0.5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C2 C1 C2 8_455 116.8(7)
C2 C1 C5 8_455 121.6(3)
C2 C1 C5 . 121.6(3)
C3 C2 C1 . 122.3(5)
C3 C2 Br2 . 118.8(4)
C1 C2 Br2 . 118.9(4)
C2 C3 C4 . 119.6(5)
C2 C3 H3A . 120.2
C4 C3 H3A . 120.2
C3 C4 C3 8_455 119.5(6)
C3 C4 C6 8_455 120.3(3)
C3 C4 C6 . 120.3(3)
N1 C5 C1 . 179.0(9)
C4 C6 H6A . 109.5
C4 C6 H6B . 109.5
H6A C6 H6B . 109.5
C4 C6 H6C . 109.5
H6A C6 H6C . 109.5
H6B C6 H6C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 8_455 1.399(6)
C1 C2 . 1.399(6)
C1 C5 . 1.437(10)
C2 C3 . 1.383(8)
C2 Br2 . 1.899(5)
C3 C4 . 1.398(6)
C3 H3A . 0.9500
C4 C3 8_455 1.398(6)
C4 C6 . 1.505(10)
C5 N1 . 1.145(11)
C6 H6A . 0.9800
C6 H6B . 0.9800
C6 H6C . 0.9800
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
C2 C1 C2 C3 8_455 . -0.5(10)
C5 C1 C2 C3 . . 178.7(7)
C2 C1 C2 Br2 8_455 . -179.7(4)
C5 C1 C2 Br2 . . -0.5(9)
C1 C2 C3 C4 . . -0.7(9)
Br2 C2 C3 C4 . . 178.5(5)
C2 C3 C4 C3 . 8_455 1.9(11)
C2 C3 C4 C6 . . -178.0(6)
