#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/96/2239601.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_2239601
loop_
_publ_author_name
'Orhan, Ersin'
'Garci, Amine'
'Therrien, Bruno'
_publ_section_title
;
 2,5-Dibromo-3,6-dimethoxycyclohexa-2,5-diene-1,4-dione
;
_journal_coeditor_code           TK5317
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o715
_journal_paper_doi               10.1107/S1600536814011787
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C8 H6 Br2 O4'
_chemical_formula_moiety         'C8 H6 Br2 O4'
_chemical_formula_sum            'C8 H6 Br2 O4'
_chemical_formula_weight         325.95
_chemical_name_systematic
;
2,5-Dibromo-3,6-dimethoxycyclohexa-2,5-diene-1,4-dione
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.846(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.4456(9)
_cell_length_b                   5.4877(3)
_cell_length_c                   10.0341(9)
_cell_measurement_reflns_used    7998
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.90
_cell_measurement_theta_min      2.35
_cell_volume                     475.71(7)
_computing_cell_refinement       'CELL (Stoe & Cie, 2000)'
_computing_data_collection       'EXPOSE (Stoe & Cie, 2000)'
_computing_data_reduction        'INTEGRATE (Stoe & Cie, 2000)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'φ oscillation'
_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  0.0714
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8772
_diffrn_reflns_theta_full        29.15
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.503
_exptl_absorpt_correction_T_max  0.704
_exptl_absorpt_correction_T_min  0.246
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   '(DIFABS; Walker & Stuart, 1983)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.979
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         1284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0280
_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)+(0.0431P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0666
_reflns_number_gt                1144
_reflns_number_total             1284
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5317sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2239601
_cod_database_fobs_code          2239601
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_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
Br Br1 0.14128(3) 0.21073(5) 0.79296(3) 0.02303(10) Uani d . 1 1
C C2 -0.0827(3) 0.2940(4) 0.9112(3) 0.0197(4) Uani d . 1 1
C C4 -0.3943(3) 0.2112(5) 0.9080(3) 0.0253(5) Uani d . 1 1
H H4A -0.4045 0.2467 0.8109 0.038 Uiso calc R 1 1
H H4B -0.4925 0.2333 0.9138 0.038 Uiso calc R 1 1
H H4C -0.3608 0.0457 0.9320 0.038 Uiso calc R 1 1
O O2 -0.2815(2) 0.3740(4) 1.00971(19) 0.0262(4) Uani d . 1 1
O O1 -0.1483(2) 0.1143(4) 0.8426(2) 0.0332(4) Uani d . 1 1
C C1 0.0654(3) 0.3806(4) 0.9134(2) 0.0176(4) Uani d . 1 1
C C3 -0.1485(2) 0.4344(4) 1.0024(2) 0.0174(4) Uani d . 1 1
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
Br1 0.02309(14) 0.02542(15) 0.02416(15) 0.00012(9) 0.01326(10) -0.00545(8)
C2 0.0212(11) 0.0197(10) 0.0193(11) -0.0009(8) 0.0093(9) -0.0011(8)
C4 0.0178(10) 0.0290(12) 0.0266(12) -0.0072(9) 0.0064(9) -0.0016(9)
O2 0.0216(8) 0.0326(9) 0.0283(9) -0.0113(7) 0.0143(7) -0.0098(8)
O1 0.0311(10) 0.0297(10) 0.0443(11) -0.0119(8) 0.0209(9) -0.0171(9)
C1 0.0185(10) 0.0190(10) 0.0169(9) 0.0013(8) 0.0090(8) -0.0011(8)
C3 0.0176(9) 0.0184(10) 0.0177(9) -0.0004(8) 0.0086(8) 0.0012(7)
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'
Br Br -0.2901 2.4595 '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'
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
O1 C2 C1 . . 122.3(2)
O1 C2 C3 . . 121.0(2)
C1 C2 C3 . . 116.68(19)
O2 C4 H4A . . 109.5
O2 C4 H4B . . 109.5
H4A C4 H4B . . 109.5
O2 C4 H4C . . 109.5
H4A C4 H4C . . 109.5
H4B C4 H4C . . 109.5
C3 O2 C4 . . 123.90(19)
C3 C1 C2 3_567 . 124.14(19)
C3 C1 Br1 3_567 . 119.87(16)
C2 C1 Br1 . . 115.96(16)
O2 C3 C1 . 3_567 118.4(2)
O2 C3 C2 . . 122.4(2)
C1 C3 C2 3_567 . 119.05(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C1 . 1.882(2)
C2 O1 . 1.219(3)
C2 C1 . 1.469(3)
C2 C3 . 1.509(3)
C4 O2 . 1.448(3)
C4 H4A . 0.9600
C4 H4B . 0.9600
C4 H4C . 0.9600
O2 C3 . 1.330(3)
C1 C3 3_567 1.351(3)
C3 C1 3_567 1.351(3)
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
O1 C2 C1 C3 3_567 -174.0(2)
C3 C2 C1 C3 3_567 4.2(4)
O1 C2 C1 Br1 . 4.2(3)
C3 C2 C1 Br1 . -177.59(16)
C4 O2 C3 C1 3_567 168.5(2)
C4 O2 C3 C2 . -15.5(4)
O1 C2 C3 O2 . -1.7(4)
C1 C2 C3 O2 . -179.9(2)
O1 C2 C3 C1 3_567 174.3(2)
C1 C2 C3 C1 3_567 -4.0(4)
