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#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/58/2205849.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_2205849
loop_
_publ_author_name
'Britton, Doyle'
_publ_section_title
;
 2,6-Dibromo-4-chlorobenzonitrile
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1726
_journal_page_last               o1727
_journal_paper_doi               10.1107/S1600536805014686
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C7 H2 Br2 Cl N'
_chemical_formula_moiety         'C7 H2 Br2 Cl N'
_chemical_formula_sum            'C7 H2 Br2 Cl N'
_chemical_formula_weight         295.37
_chemical_name_systematic
;
2,6-Dibromo-4-chlorobenzonitrile
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 93.980(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.666(2)
_cell_length_b                   10.125(3)
_cell_length_c                   4.7776(12)
_cell_measurement_reflns_used    2165
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.4
_cell_volume                     418.19(19)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Siemens area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_sigmaI/netI    0.018
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2839
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        <1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.938
_exptl_absorpt_correction_T_max  0.37
_exptl_absorpt_correction_T_min  0.19
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996; Blessing, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.39
_refine_ls_extinction_coef       0.047(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     63
_refine_ls_number_reflns         1001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.09
_refine_ls_R_factor_all          0.023
_refine_ls_R_factor_gt           0.022
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.033P)²+0.25P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.056
_refine_ls_wR_factor_ref         0.057
_reflns_number_gt                930
_reflns_number_total             1001
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac6176.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2205849
_cod_database_fobs_code          2205849
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_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
_atom_site_occupancy
_atom_site_type_symbol
Br2 0.19034(3) 0.53047(2) 0.33819(5) 0.02675(13) Uani d . 1 Br
Cl4 0.57102(9) 0.2500 1.09654(16) 0.0267(2) Uani d S 1 Cl
N1 -0.0135(4) 0.2500 -0.0187(7) 0.0326(7) Uani d S 1 N
C1 0.2005(3) 0.2500 0.3857(6) 0.0216(6) Uani d S 1 C
C2 0.2606(3) 0.3689(2) 0.4963(5) 0.0215(4) Uani d . 1 C
C3 0.3745(3) 0.3697(3) 0.7146(5) 0.0228(5) Uani d . 1 C
C4 0.4286(4) 0.2500 0.8216(6) 0.0222(6) Uani d S 1 C
C5 0.0815(4) 0.2500 0.1607(7) 0.0248(7) Uani d S 1 C
H3 0.413(4) 0.452(3) 0.772(6) 0.026(7) Uiso d . 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br2 0.02831(18) 0.01858(17) 0.03282(18) 0.00133(8) -0.00176(10) 0.00351(8)
Cl4 0.0270(4) 0.0293(4) 0.0230(4) 0.000 -0.0047(3) 0.000
N1 0.0320(16) 0.0247(15) 0.0393(18) 0.000 -0.0096(13) 0.000
C1 0.0198(15) 0.0237(17) 0.0212(14) 0.000 0.0013(11) 0.000
C2 0.0231(10) 0.0179(11) 0.0237(10) 0.0017(9) 0.0032(8) 0.0019(8)
C3 0.0230(11) 0.0211(12) 0.0243(11) -0.0014(9) 0.0015(8) -0.0021(8)
C4 0.0225(15) 0.0245(17) 0.0193(14) 0.000 0.0003(11) 0.000
C5 0.0257(16) 0.0189(16) 0.0293(16) 0.000 -0.0012(13) 0.000
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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C2 . 4_565 118.5(3)
C2 C1 C5 . . 120.73(14)
C2 C1 C5 4_565 . 120.73(14)
C3 C2 C1 . . 121.1(2)
C3 C2 Br2 . . 119.32(18)
C1 C2 Br2 . . 119.57(17)
C4 C3 C2 . . 118.6(2)
C4 C3 H3 . . 124.9(18)
C2 C3 H3 . . 116.5(18)
C3 C4 C3 4_565 . 122.2(3)
C3 C4 Cl4 4_565 . 118.91(15)
C3 C4 Cl4 . . 118.91(15)
N1 C5 C1 . . 180.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br2 C2 . 1.885(2)
Cl4 C4 . 1.739(3)
N1 C5 . 1.146(5)
C1 C2 . 1.400(3)
C1 C2 4_565 1.400(3)
C1 C5 . 1.437(4)
C2 C3 . 1.385(3)
C3 C4 . 1.385(3)
C3 H3 . 0.93(3)
C4 C3 4_565 1.385(3)
