#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/08/2240825.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_2240825
loop_
_publ_author_name
'Broichhagen, Johannes'
'Woodmansee, David H.'
'Trauner, Dirk'
'Mayer, Peter'
_publ_section_title
;
 Crystal structure of
 (E)-1,2-bis(4-bromo-2,6-difluorophenyl)diazene
;
_journal_coeditor_code           NR2060
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o459
_journal_page_last               o460
_journal_paper_doi               10.1107/S2056989015010622
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C12 H4 Br2 F4 N2'
_chemical_formula_moiety         'C12 H4 Br2 F4 N2'
_chemical_formula_sum            'C12 H4 Br2 F4 N2'
_chemical_formula_weight         411.975
_chemical_name_systematic
;
(E)-1,2-bis(4-bromo-2,6-difluorophenyl)diazene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.340(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.3274(5)
_cell_length_b                   4.5667(2)
_cell_length_c                   13.1039(6)
_cell_measurement_reflns_used    95
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.6351
_cell_measurement_theta_min      5.4120
_cell_volume                     618.00(5)
_computing_cell_refinement
;
APEX2 (Bruker, 2007)
;
_computing_data_collection
;
Bruker Instrument Service (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-III (Burnett & Johnson, 1996)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL-2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR97 (Altomare et al.,  1999)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9803
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         3.11
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.597
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.21395(18)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.298
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0231P)²+0.2317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0503
_refine_ls_wR_factor_ref         0.0547
_reflns_number_gt                1218
_reflns_number_total             1523
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            nr2060sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2240825
_cod_database_fobs_code          2240825
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2.014
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.3771(2) 0.7379(5) 0.52174(17) 0.0188(5) Uani d . 1 1
C C2 0.2748(2) 0.6243(6) 0.46388(18) 0.0232(5) Uani d . 1 1
C C3 0.1860(2) 0.4296(6) 0.49948(18) 0.0233(5) Uani d . 1 1
H H3 0.1179 0.3594 0.4570 0.028 Uiso calc R 1 1
C C4 0.1983(2) 0.3376(5) 0.59963(18) 0.0197(5) Uani d . 1 1
C C5 0.2992(2) 0.4325(5) 0.66162(18) 0.0216(5) Uani d . 1 1
H H5 0.3084 0.3629 0.7296 0.026 Uiso calc R 1 1
C C6 0.3856(2) 0.6304(5) 0.62162(18) 0.0205(5) Uani d . 1 1
N N1 0.45691(19) 0.9452(5) 0.47266(15) 0.0234(4) Uani d . 1 1
F F1 0.26329(15) 0.7158(4) 0.36666(10) 0.0382(4) Uani d . 1 1
F F2 0.48197(15) 0.7201(4) 0.68235(11) 0.0373(4) Uani d . 1 1
Br Br1 0.07408(2) 0.08357(6) 0.656884(19) 0.02666(10) Uani d . 1 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'
F F 0.0171 0.0103 '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
C2 C1 C6 . 114.8(2)
C2 C1 N1 . 116.3(2)
C6 C1 N1 . 128.9(2)
F1 C2 C3 . 118.1(2)
F1 C2 C1 . 117.5(2)
C3 C2 C1 . 124.4(2)
C2 C3 C4 . 117.7(2)
C2 C3 H3 . 121.2
C4 C3 H3 . 121.2
C3 C4 C5 . 121.7(2)
C3 C4 Br1 . 120.30(18)
C5 C4 Br1 . 117.97(18)
C6 C5 C4 . 117.9(2)
C6 C5 H5 . 121.0
C4 C5 H5 . 121.0
F2 C6 C5 . 117.2(2)
F2 C6 C1 . 119.4(2)
C5 C6 C1 . 123.3(2)
N1 N1 C1 3_676 115.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.397(3)
C1 C6 . 1.400(3)
C1 N1 . 1.412(3)
C2 F1 . 1.345(3)
C2 C3 . 1.362(3)
C3 C4 . 1.383(3)
C3 H3 . 0.9500
C4 C5 . 1.387(3)
C4 Br1 . 1.888(2)
C5 C6 . 1.376(3)
C5 H5 . 0.9500
C6 F2 . 1.335(3)
N1 N1 3_676 1.244(4)
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
C5 H5 F2 2_646 0.95 2.53 3.190(3) 126 yes
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_4
_geom_torsion
C6 C1 C2 F1 . -178.8(2)
N1 C1 C2 F1 . 1.6(3)
C6 C1 C2 C3 . 1.7(4)
N1 C1 C2 C3 . -177.9(2)
F1 C2 C3 C4 . -179.7(2)
C1 C2 C3 C4 . -0.2(4)
C2 C3 C4 C5 . -1.7(4)
C2 C3 C4 Br1 . 176.76(18)
C3 C4 C5 C6 . 2.1(4)
Br1 C4 C5 C6 . -176.42(17)
C4 C5 C6 F2 . 179.8(2)
C4 C5 C6 C1 . -0.5(4)
C2 C1 C6 F2 . 178.4(2)
N1 C1 C6 F2 . -2.1(4)
C2 C1 C6 C5 . -1.2(4)
N1 C1 C6 C5 . 178.3(2)
C2 C1 N1 N1 3_676 176.3(3)
C6 C1 N1 N1 3_676 -3.2(4)
