#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/08/2230877.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_2230877
loop_
_publ_author_name
'Stein, Mario'
'Schwarzer, Anke'
'Hulliger, Jürg'
'Weber, Edwin'
_publ_section_title
;
 1-Bromo-2,3,5,6-tetrafluoro-4-nitrobenzene
;
_journal_coeditor_code           SU2278
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1655
_journal_paper_doi               10.1107/S160053681102201X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C6 Br F4 N O2'
_chemical_formula_moiety         'C6 Br F4 N O2'
_chemical_formula_sum            'C6 Br F4 N O2'
_chemical_formula_weight         273.98
_chemical_name_common
;
1-Bromo-2,3,5,6-tetrafluoro-4-nitrobenzene
;
_chemical_name_systematic
;
1-Bromo-2,3,5,6-tetrafluoro-4-nitrobenzene
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6718(3)
_cell_length_b                   10.9476(6)
_cell_length_c                   12.2652(8)
_cell_measurement_reflns_used    2319
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      32.77
_cell_measurement_theta_min      3.72
_cell_volume                     761.58(8)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4314
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    5.441
_exptl_absorpt_correction_T_max  0.6122
_exptl_absorpt_correction_T_min  0.5359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.534
_refine_ls_abs_structure_details 'Flack (1983), 636 Friedel pairs'
_refine_ls_abs_structure_Flack   0.026(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1550
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0227
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0208P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0522
_refine_ls_wR_factor_ref         0.0529
_reflns_number_gt                1447
_reflns_number_total             1550
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            su2278.cif
_cod_data_source_block           I
_cod_database_code               2230877
_cod_database_fobs_code          2230877
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 1.16169(4) 0.62891(2) 0.12241(5) 0.01760(10) Uani d . 1 1 . .
F F1 0.9560(3) 0.69267(15) -0.10033(17) 0.0188(4) Uani d . 1 1 . .
F F2 0.6066(3) 0.58458(16) -0.20909(18) 0.0178(4) Uani d . 1 1 . .
F F3 0.5004(3) 0.30738(15) 0.08418(15) 0.0181(4) Uani d . 1 1 . .
F F4 0.8565(3) 0.41466(18) 0.19058(19) 0.0192(4) Uani d . 1 1 . .
N N1 0.3610(4) 0.3813(2) -0.1276(3) 0.0148(6) Uani d . 1 1 . .
O O1 0.3925(4) 0.36408(18) -0.2245(2) 0.0181(5) Uani d . 1 1 . .
O O2 0.1833(3) 0.3518(2) -0.0760(2) 0.0207(6) Uani d . 1 1 . .
C C1 0.8465(4) 0.5971(3) -0.0542(3) 0.0134(7) Uani d . 1 1 . .
C C2 0.6671(4) 0.5405(3) -0.1118(3) 0.0136(7) Uani d . 1 1 . .
C C3 0.5498(4) 0.4424(3) -0.0658(3) 0.0128(7) Uani d . 1 1 . .
C C4 0.6105(5) 0.4023(3) 0.0374(3) 0.0146(7) Uani d . 1 1 . .
C C5 0.7936(4) 0.4574(3) 0.0933(3) 0.0129(8) Uani d . 1 1 . .
C C6 0.9119(4) 0.5558(3) 0.0468(3) 0.0146(7) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 Br1 O1 . 2_765 155.87(10) ?
C6 Br1 O1 . 4_655 124.16(9) ?
O1 Br1 O1 2_765 4_655 73.03(6) ?
C1 F1 F2 . 3_565 169.53(15) ?
C2 F2 F3 . 2_664 176.03(17) ?
C2 F2 F4 . 2_664 127.90(16) ?
F3 F2 F4 2_664 2_664 55.33(6) ?
C2 F2 F1 . 3_465 88.19(17) ?
F3 F2 F1 2_664 3_465 89.86(7) ?
F4 F2 F1 2_664 3_465 85.76(7) ?
C4 F3 O2 . 3 90.56(18) ?
C4 F3 F2 . 2_665 99.04(18) ?
O2 F3 F2 3 2_665 161.63(9) ?
C4 F3 F4 . 3_455 168.70(16) ?
O2 F3 F4 3 3_455 84.17(8) ?
F2 F3 F4 2_665 3_455 83.52(8) ?
C5 F4 F3 . 3 88.06(17) ?
C5 F4 F2 . 2_665 97.86(13) ?
F3 F4 F2 3 2_665 116.85(8) ?
O1 N1 O2 . . 125.5(3) ?
O1 N1 C3 . . 117.8(2) ?
O2 N1 C3 . . 116.6(3) ?
N1 O1 Br1 . 2_764 134.13(18) ?
N1 O1 Br1 . 4_644 133.10(18) ?
Br1 O1 Br1 2_764 4_644 75.36(6) ?
N1 O2 F3 . 3_455 144.98(19) ?
F1 C1 C6 . . 120.9(3) ?
F1 C1 C2 . . 118.2(3) ?
C6 C1 C2 . . 120.8(3) ?
F2 C2 C3 . . 121.5(3) ?
F2 C2 C1 . . 119.0(3) ?
C3 C2 C1 . . 119.5(3) ?
C4 C3 C2 . . 120.0(3) ?
C4 C3 N1 . . 120.6(3) ?
C2 C3 N1 . . 119.5(3) ?
F3 C4 C5 . . 118.4(3) ?
F3 C4 C3 . . 121.4(3) ?
C5 C4 C3 . . 120.1(3) ?
F4 C5 C4 . . 119.5(3) ?
F4 C5 C6 . . 120.7(3) ?
C4 C5 C6 . . 119.8(3) ?
C1 C6 C5 . . 119.7(3) ?
C1 C6 Br1 . . 120.8(2) ?
C5 C6 Br1 . . 119.5(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C6 . 1.874(3) ?
Br1 O1 2_765 3.150(2) y
Br1 O1 4_655 3.201(2) y
F3 O2 3 2.823(3) y
F1 C1 . 1.342(3) ?
F1 F2 3_565 2.908(3) y
F2 C2 . 1.332(4) ?
F2 F3 2_664 2.863(3) y
F2 F4 2_664 2.901(2) y
F2 F1 3_465 2.908(3) ?
F3 C4 . 1.341(3) ?
F3 F2 2_665 2.863(3) ?
F3 F4 3_455 2.877(2) y
F4 C5 . 1.331(4) ?
F4 F3 3 2.877(2) ?
F4 F2 2_665 2.901(2) ?
N1 O1 . 1.217(4) ?
N1 O2 . 1.234(3) ?
N1 C3 . 1.472(4) ?
O1 Br1 2_764 3.150(2) ?
O1 Br1 4_644 3.201(2) ?
O2 F3 3_455 2.823(3) ?
C1 C6 . 1.369(5) ?
C1 C2 . 1.385(4) ?
C2 C3 . 1.385(4) ?
C3 C4 . 1.383(5) ?
C4 C5 . 1.382(4) ?
C5 C6 . 1.391(4) ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 N1 O1 Br1 . . . 2_764 -164.81(19) ?
C3 N1 O1 Br1 . . . 2_764 15.2(4) ?
O2 N1 O1 Br1 . . . 4_644 -49.6(4) ?
C3 N1 O1 Br1 . . . 4_644 130.4(2) ?
O1 N1 O2 F3 . . . 3_455 110.3(4) ?
C3 N1 O2 F3 . . . 3_455 -69.7(4) ?
F2 F1 C1 C6 3_565 . . . -133.4(10) ?
F2 F1 C1 C2 3_565 . . . 47.2(13) ?
F3 F2 C2 C3 2_664 . . . 174(2) ?
F4 F2 C2 C3 2_664 . . . 30.2(4) ?
F1 F2 C2 C3 3_465 . . . 113.4(3) ?
F3 F2 C2 C1 2_664 . . . -4(3) ?
F4 F2 C2 C1 2_664 . . . -147.6(2) ?
F1 F2 C2 C1 3_465 . . . -64.4(3) ?
F1 C1 C2 F2 . . . . -1.5(4) ?
C6 C1 C2 F2 . . . . 179.1(3) ?
F1 C1 C2 C3 . . . . -179.4(3) ?
C6 C1 C2 C3 . . . . 1.2(4) ?
F2 C2 C3 C4 . . . . -177.2(3) ?
C1 C2 C3 C4 . . . . 0.6(4) ?
F2 C2 C3 N1 . . . . 2.9(4) ?
C1 C2 C3 N1 . . . . -179.2(3) ?
O1 N1 C3 C4 . . . . -138.6(3) ?
O2 N1 C3 C4 . . . . 41.4(4) ?
O1 N1 C3 C2 . . . . 41.3(4) ?
O2 N1 C3 C2 . . . . -138.7(3) ?
O2 F3 C4 C5 3 . . . -112.3(3) ?
F2 F3 C4 C5 2_665 . . . 52.0(3) ?
F4 F3 C4 C5 3_455 . . . -50.3(12) ?
O2 F3 C4 C3 3 . . . 65.5(3) ?
F2 F3 C4 C3 2_665 . . . -130.3(3) ?
F4 F3 C4 C3 3_455 . . . 127.4(9) ?
C2 C3 C4 F3 . . . . -179.9(3) ?
N1 C3 C4 F3 . . . . 0.0(4) ?
C2 C3 C4 C5 . . . . -2.2(4) ?
N1 C3 C4 C5 . . . . 177.7(3) ?
F3 F4 C5 C4 3 . . . 65.3(3) ?
F2 F4 C5 C4 2_665 . . . -51.5(3) ?
F3 F4 C5 C6 3 . . . -113.9(3) ?
F2 F4 C5 C6 2_665 . . . 129.2(2) ?
F3 C4 C5 F4 . . . . 0.5(4) ?
C3 C4 C5 F4 . . . . -177.2(2) ?
F3 C4 C5 C6 . . . . 179.8(3) ?
C3 C4 C5 C6 . . . . 2.0(4) ?
F1 C1 C6 C5 . . . . 179.2(3) ?
C2 C1 C6 C5 . . . . -1.4(4) ?
F1 C1 C6 Br1 . . . . -1.6(4) ?
C2 C1 C6 Br1 . . . . 177.8(2) ?
F4 C5 C6 C1 . . . . 179.0(3) ?
C4 C5 C6 C1 . . . . -0.2(4) ?
F4 C5 C6 Br1 . . . . -0.2(4) ?
C4 C5 C6 Br1 . . . . -179.4(2) ?
O1 Br1 C6 C1 2_765 . . . -143.2(2) ?
O1 Br1 C6 C1 4_655 . . . 86.1(3) ?
O1 Br1 C6 C5 2_765 . . . 36.0(4) ?
O1 Br1 C6 C5 4_655 . . . -94.7(2) ?
