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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/2/31/15/2311535.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_2311535
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_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          401
_chemical_name_common            RNC
_chemical_name_systematic
;
2,6-Dibromo-4-methylphenyl isocyanide
;
_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-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.690(5)
_cell_length_b                   14.690(5)
_cell_length_c                   4.0703(15)
_cell_measurement_reflns_used    2995
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.91
_cell_measurement_theta_min      2.77
_cell_volume                     878.4(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      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            10248
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.594
_diffrn_reflns_theta_min         1.961
_exptl_absorpt_coefficient_mu    9.160
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.079
_exptl_crystal_description       Needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.509
_refine_ls_abs_structure_details
;
Flack x determined using 381 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   -0.024(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     59
_refine_ls_number_reflns         1074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0232
_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)+(0.0267P)²+0.0073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0500
_refine_ls_wR_factor_ref         0.0508
_reflns_number_gt                1001
_reflns_number_total             1074
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5859sup1.cif
_cod_data_source_block           RNC
_cod_original_cell_volume        878.3(7)
_cod_database_code               2311535
_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   0.121
_shelx_estimated_absorpt_t_max   0.528
_shelxl_version_number           2014/6
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
Br Br12 0.64344(3) 0.58324(2) 0.38265(14) 0.03268(14) Uani d 1
N N11 0.8281(2) 0.6719(2) 0.5307(11) 0.0278(11) Uani d 1
C C11 0.7708(2) 0.7292(2) 0.3538(15) 0.0228(11) Uani d 1
C C12 0.6845(3) 0.7013(3) 0.2671(9) 0.0245(8) Uani d 1
C C13 0.6256(2) 0.7587(2) 0.0981(10) 0.0243(8) Uani d 1
H H13A 0.5664 0.7382 0.0402 0.029 Uiso calc 1
C C14 0.6535(3) 0.8465(3) 0.0132(13) 0.0237(11) Uani d 1
C C15 0.8753(3) 0.6247(3) 0.6829(18) 0.0474(18) Uani d 1
C C16 0.5894(3) 0.9106(3) -0.1624(14) 0.0328(12) Uani d 1
H H16A 0.5318 0.8793 -0.2065 0.049 Uiso calc 0.5
H H16B 0.6169 0.9300 -0.3703 0.049 Uiso calc 0.5
H H16C 0.5781 0.9640 -0.0241 0.049 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 0.0033 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'
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
C15 N11 C11 . . 178.9(6)
C12 C11 C12 . 7_665 118.7(5)
C12 C11 N11 . . 120.6(3)
C12 C11 N11 7_665 . 120.6(3)
C11 C12 C13 . . 121.3(4)
C11 C12 Br12 . . 120.0(3)
C13 C12 Br12 . . 118.7(3)
C12 C13 C14 . . 120.0(4)
C12 C13 H13A . . 120.0
C14 C13 H13A . . 120.0
C13 C14 C13 . 7_665 118.7(5)
C13 C14 C16 . . 120.6(2)
C13 C14 C16 7_665 . 120.6(2)
C14 C16 H16A . . 109.5
C14 C16 H16B . . 109.5
H16A C16 H16B . . 109.5
C14 C16 H16C . . 109.5
H16A C16 H16C . . 109.5
H16B C16 H16C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br12 C12 . 1.896(4)
N11 C15 . 1.161(8)
N11 C11 . 1.391(7)
C11 C12 . 1.379(5)
C11 C12 7_665 1.379(5)
C12 C13 . 1.389(6)
C13 C14 . 1.396(4)
C13 H13A . 0.9500
C14 C13 7_665 1.396(4)
C14 C16 . 1.511(7)
C16 H16A . 0.9800
C16 H16B . 0.9800
C16 H16C . 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
C12 C11 C12 C13 7_665 . -0.5(8)
N11 C11 C12 C13 . . 178.2(4)
C12 C11 C12 Br12 7_665 . -179.8(3)
N11 C11 C12 Br12 . . -1.1(7)
C11 C12 C13 C14 . . -0.1(6)
Br12 C12 C13 C14 . . 179.2(3)
C12 C13 C14 C13 . 7_665 0.7(7)
C12 C13 C14 C16 . . -178.3(4)
