#------------------------------------------------------------------------------
#$Date: 2016-01-14 05:27:54 +0200 (Thu, 14 Jan 2016) $
#$Revision: 174447 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/14/2241465.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_2241465
loop_
_publ_author_name
'Britton, Doyle'
'Noland, Wayland E.'
'Tritch, Kenneth J.'
_publ_section_title
;
 Two new polytypes of 2,4,6-tribromobenzonitrile
;
_journal_coeditor_code           LH5796
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              178
_journal_page_last               183
_journal_paper_doi               10.1107/S2056989016000256
_journal_volume                  72
_journal_year                    2016
_chemical_formula_moiety         'C7 H2 Br3 N'
_chemical_formula_sum            'C7 H2 Br3 N'
_chemical_formula_weight         339.83
_chemical_name_systematic
;
 1,3,5-Tribromo-2-isocyanobenzene - polytype II
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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            8
_cell_length_a                   13.5916(18)
_cell_length_b                   10.1464(13)
_cell_length_c                   12.6158(16)
_cell_measurement_reflns_used    2721
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      3.00
_cell_volume                     1739.8(4)
_computing_cell_refinement
;
SAINT (Bruker, 2002)
;
_computing_data_collection
;
APEX2 (Bruker, 2002)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), enCIFer (Allen et al.,
2004),
and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (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  0.0782
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19459
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_min         2.203
_exptl_absorpt_coefficient_mu    13.841
_exptl_absorpt_correction_T_max  0.3334
_exptl_absorpt_correction_T_min  0.1704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2002)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.595
_exptl_crystal_description       Block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.480
_refine_ls_extinction_coef       0.00269(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         2105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0254
_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)+(0.0121P)²+1.0004P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0507
_refine_ls_wR_factor_ref         0.0554
_reflns_number_gt                1638
_reflns_number_total             2105
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5796sup1.cif
_cod_data_source_block           RNC-II
_cod_database_code               2241465
_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   0.072
_shelx_estimated_absorpt_t_max   0.168
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
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 C121 0.3678(3) 0.7500 0.5680(3) 0.0162(9) Uani d 1
C C122 0.3637(2) 0.6315(3) 0.6238(2) 0.0176(7) Uani d 1
C C123 0.3573(2) 0.6306(3) 0.7332(2) 0.0182(7) Uani d 1
H H123 0.3541 0.5499 0.7712 0.022 Uiso calc 1
C C124 0.3559(3) 0.7500 0.7858(4) 0.0173(9) Uani d 1
N N127 0.3793(3) 0.7500 0.4583(3) 0.0215(9) Uani d 1
C C127 0.3909(4) 0.7500 0.3682(4) 0.0285(12) Uani d 1
Br Br122 0.36763(3) 0.47074(3) 0.54952(3) 0.02456(11) Uani d 1
Br Br124 0.35282(4) 0.7500 0.93610(4) 0.02254(13) Uani d 1
C C131 0.3904(3) 0.2500 0.1747(3) 0.0161(10) Uani d 1
C C132 0.3885(2) 0.3685(3) 0.1192(3) 0.0169(7) Uani d 1
C C133 0.3821(2) 0.3691(3) 0.0100(2) 0.0179(7) Uani d 1
H H133 0.3806 0.4499 -0.0281 0.021 Uiso calc 1
C C134 0.3781(3) 0.2500 -0.0428(4) 0.0190(10) Uani d 1
N N137 0.3955(3) 0.2500 0.2840(3) 0.0180(8) Uani d 1
C C137 0.3995(3) 0.2500 0.3761(4) 0.0246(11) Uani d 1
Br Br132 0.39399(3) 0.52885(3) 0.19404(3) 0.02480(11) Uani d 1
Br Br134 0.36801(4) 0.2500 -0.19267(4) 0.02564(14) 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'
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
N127 C121 C122 . 7_575 120.4(2)
C122 C121 C122 . 7_575 119.1(4)
C123 C122 C121 . . 120.8(3)
C123 C122 Br122 . . 119.6(2)
C121 C122 Br122 . . 119.6(2)
C124 C123 C122 . . 118.3(3)
C124 C123 H123 . . 120.8
C122 C123 H123 . . 120.8
C123 C124 C123 . 7_575 122.5(4)
C123 C124 Br124 7_575 . 118.7(2)
C127 N127 C121 . . 178.5(5)
N137 C131 C132 . 7_565 120.3(2)
C132 C131 C132 7_565 . 119.5(4)
C133 C132 C131 . . 120.5(3)
C133 C132 Br132 . . 119.9(2)
C131 C132 Br132 . . 119.5(2)
C132 C133 C134 . . 118.7(3)
C132 C133 H133 . . 120.7
C134 C133 H133 . . 120.7
C133 C134 C133 7_565 . 122.1(4)
C133 C134 Br134 7_565 . 118.9(2)
C137 N137 C131 . . 179.8(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C121 N127 . 1.393(6)
C121 C122 7_575 1.395(4)
C122 C123 . 1.382(4)
C122 Br122 . 1.882(3)
C123 C124 7_575 1.381(4)
C123 H123 . 0.9500
C124 Br124 . 1.897(5)
N127 C127 . 1.147(6)
C131 N137 . 1.380(6)
C131 C132 7_565 1.392(4)
C132 C133 . 1.380(4)
C132 Br132 . 1.883(3)
C133 C134 7_565 1.381(4)
C133 H133 . 0.9500
C134 Br134 . 1.895(4)
N137 C137 . 1.164(6)
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
C123 H123 Br134 1_556 0.95 3.08 3.976(3) 157.3 n
C133 H133 Br124 1_554 0.95 3.10 3.995(3) 157.4 n
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
N127 C121 C122 C123 . . 176.7(3)
C122 C121 C122 C123 7_575 . -1.0(6)
N127 C121 C122 Br122 . . -3.0(5)
C122 C121 C122 Br122 7_575 . 179.30(19)
C121 C122 C123 C124 . . -0.5(5)
Br122 C122 C123 C124 . . 179.2(3)
C122 C123 C124 C123 . 7_575 2.1(7)
C122 C123 C124 Br124 . . -177.4(2)
N137 C131 C132 C133 . . -179.2(3)
C132 C131 C132 C133 7_565 . 1.6(6)
N137 C131 C132 Br132 . . 0.6(5)
C132 C131 C132 Br132 7_565 . -178.6(2)
C131 C132 C133 C134 . . -0.2(5)
Br132 C132 C133 C134 . . -179.9(3)
C132 C133 C134 C133 . 7_565 -1.3(7)
C132 C133 C134 Br134 . . 179.3(3)

_cod_database_fobs_code 2241465
