#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/55/2105534.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_2105534
loop_
_publ_author_name
'Thalladi, Venkat R.'
'Weiss, Hans-Christoph'
'Boese, Roland'
'Nangia, Ashwini'
'Desiraju, Gautam R.'
_publ_section_title
;
 A comparative study of the crystal structures of tetrahalogenated
 hydroquinones and γ-hydroquinone
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              1005
_journal_page_last               1013
_journal_paper_doi               10.1107/S0108768199005911
_journal_volume                  55
_journal_year                    1999
_chemical_formula_analytical     'C6 H2 Br4 O2'
_chemical_formula_moiety         'C6 H2 Br4 O2'
_chemical_formula_sum            'C6 H2 Br4 O2'
_chemical_formula_weight         425.72
_chemical_melting_point          517
_chemical_name_common            Tetrabromohydroquinone
_chemical_name_systematic
;
 2,3,5,6-Tetrabromohydroquinone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 92.1670(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.8907(2)
_cell_length_b                   4.73160(10)
_cell_length_c                   11.0612(3)
_cell_measurement_reflns_used    2859
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      2.89
_cell_volume                     464.981(19)
_computing_cell_refinement       'SAINT V.4.050 (Siemens, 1995)'
_computing_data_collection       'SMART V.4.209 (Siemens, 1995)'
_computing_data_reduction        'SAINT V.4.050 (Siemens, 1995)'
_computing_molecular_graphics    'SHELXTL V.5.03 (Siemens, 1994b)'
_computing_publication_material  'SHELXTL V.5.03 (Siemens, 1994b)'
_computing_structure_refinement  'SHELXTL V.5.03 (Siemens, 1994b)'
_computing_structure_solution    'SHELXTL V.5.03 (Siemens, 1994b)'
_diffrn_ambient_temperature      303(2)
_diffrn_measurement_device       'Siemens SMART diffractometer'
_diffrn_measurement_method
; Data collection in ω at 0.3 ° scan width, four runs with
  636, 465, 636 and 465 frames, Φ = 0, 88, 180, 270
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .1501
_diffrn_reflns_av_sigmaI/netI    .1323
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4829
_diffrn_reflns_theta_max         28.18
_diffrn_reflns_theta_min         2.89
_diffrn_standards_decay_%        'No decay'
_diffrn_standards_interval_count none
_diffrn_standards_number
' no standard reflections, CCD area detector data'
_exptl_absorpt_coefficient_mu    17.263
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  .16
_exptl_absorpt_correction_type   'empirical SADABS (Blessing, 1995)'
_exptl_absorpt_process_details
' Siemens SADABS program has been used for the absorption correction'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    3.041
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          .58
_exptl_crystal_size_mid          .46
_exptl_crystal_size_min          .32
_refine_diff_density_max         2.035
_refine_diff_density_min         -1.923
_refine_ls_extinction_coef       .0017(14)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   .929
_refine_ls_goodness_of_fit_obs   1.160
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     56
_refine_ls_number_reflns         1130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .929
_refine_ls_restrained_S_obs      1.160
_refine_ls_R_factor_all          .0843
_refine_ls_R_factor_obs          .0665
_refine_ls_shift/esd_max         .001
_refine_ls_shift/esd_mean        .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0448P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .1462
_refine_ls_wR_factor_obs         .1431
_reflns_number_observed          709
_reflns_number_total             1130
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            an0560.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        464.98(2)
_cod_database_code               2105534
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
O .021(4) .050(5) .022(4) .003(3) .008(3) .006(3)
Br1 .0203(5) .0599(8) .0298(7) .0126(4) .0009(4) .0003(5)
Br2 .0276(6) .0463(8) .0206(6) .0010(4) -.0028(4) .0073(4)
C1 .018(4) .031(5) .017(5) -.001(3) .003(3) -.004(4)
C2 .012(4) .036(6) .014(5) .000(3) -.001(3) .001(4)
C3 .017(4) .034(5) .012(5) -.002(3) -.008(3) .000(4)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O .2092(6) .5559(14) -.1783(6) .031(2) Uani d . 1 O
H0A .1779(6) .6640(14) -.2315(6) .046 Uiso calc R 1 H
Br1 .32011(10) .1586(3) .01217(10) .0367(4) Uani d . 1 Br
Br2 .07172(10) .0776(2) .22943(9) .0316(4) Uani d . 1 Br
C1 .1052(9) .5344(18) -.0910(8) .022(2) Uani d . 1 C
C2 .1356(8) .354(2) .0062(8) .021(2) Uani d . 1 C
C3 .0310(9) .3210(19) .0963(8) .021(2) Uani d . 1 C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -.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
O C1 C3 . 3_565 123.1(8)
O C1 C2 . . 118.4(8)
C3 C1 C2 3_565 . 118.5(8)
C1 C2 C3 . . 120.2(8)
C1 C2 Br1 . . 118.1(6)
C3 C2 Br1 . . 121.6(7)
C1 C3 C2 3_565 . 121.2(8)
C1 C3 Br2 3_565 . 118.2(6)
C2 C3 Br2 . . 120.6(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O C1 . 1.366(9)
Br1 C2 . 1.881(8)
Br2 C3 . 1.893(9)
C1 C3 3_565 1.390(11)
C1 C2 . 1.393(13)
C2 C3 . 1.396(12)
C3 C1 3_565 1.390(11)
