##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL
_journal_date_recd_electronic     2008-09-19
_journal_date_accepted     2008-10-13
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2008
_journal_volume     64
_journal_issue     11
_journal_page_first     o604
_journal_page_last     o608
_journal_paper_category     FO
_journal_coeditor_code     UK3001
_publ_contact_author
;
 Baggio, Ricardo F.
 Departamento de Física,
 Comisión Nacional de Energía Atómica
 Av. gral Paz 1499,
 1650 San Martín, Buenos Aires, Argentina.
;
_publ_contact_author_email     baggio@cnea.gov.ar
_publ_contact_author_fax     54-11-6772_7121
_publ_contact_author_phone     54-11-6772_7109
_publ_section_title
;
Halogen bonding in 1,2-dibromo-4,5-dimethoxybenzene and
1,2-diiodo-4,5-dimethoxybenzene
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Cukiernik, Fabio D.' .
;
Departamento de Química Inorgánica, Analítica y Química Física,
Facultad de Ciencias Exactas y Naturales, UBA
Buenos Aires, Argentina
and
Instituto de Ciencias, Universidad Nacional de General Sarmiento,
Buenos Aires, Argentina
;
    'Zelcer, Andrés'
;
Current address: Gerencia Química, Centro Atómico Constituyentes,
Comisión Nacional de Energía Atómica,
Buenos Aires, Argentina.
;
;
Departamento de Química Inorgánica, Analítica y Química Física,
Facultad de Ciencias Exactas y Naturales, UBA
Buenos Aires, Argentina
;
    'Garland, Maria Teresa' .
;
Departamento de Física,
Facultad de Ciencias Físicas y Matemáticas and CIMAT,
Universidad de Chile,
Santiago de Chile, Chile
;
    'Baggio, Ricardo' .
;
Departamento de Física, Centro Atómico Constituyentes,
Comisión Nacional de Energía Atómica
Buenos Aires, Argentina
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1,2-Dibromo-4,5-dimethoxybenzene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H8 Br2 O2'
_chemical_formula_sum     'C8 H8 Br2 O2'
_chemical_formula_iupac     'C8 H8 Br2 O2'
_chemical_formula_weight     295.96
_chemical_melting_point     363.0(10)
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     10.1172(5)
_cell_length_b     10.2052(5)
_cell_length_c     20.2764(10)
_cell_angle_alpha     104.1710(12)
_cell_angle_beta     98.9405(10)
_cell_angle_gamma     101.0630(12)
_cell_volume     1946.46(17)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     6539
_cell_measurement_theta_min     2.54
_cell_measurement_theta_max     24.65
_cell_measurement_temperature     294(2)
_exptl_crystal_description     blocks
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.16
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     2.020
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1136
_exptl_absorpt_coefficient_mu     8.287
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2002)'
_exptl_absorpt_correction_T_min     0.28
_exptl_absorpt_correction_T_max     0.32
_exptl_special_details
;
Characterization was performed by NMR (Bruker Avance300 using CDCl3 as solvent
 and its residual peak as internal reference at 7.26 p.p.m.) and elemental
 analysis (Carlo Erba CHNS-O EA1108 at the Servicio de Microanálisis of
 Inquimae).
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     30774
_diffrn_reflns_av_R_equivalents     0.0327
_diffrn_reflns_av_sigmaI/netI     0.0370
_diffrn_reflns_theta_min     2.08
_diffrn_reflns_theta_max     27.92
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.927
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     26
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     8656
_reflns_number_gt     5046
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0784
_refine_ls_R_factor_gt     0.0356
_refine_ls_wR_factor_gt     0.0816
_refine_ls_wR_factor_ref     0.0966
_refine_ls_goodness_of_fit_ref     1.015
_refine_ls_restrained_S_all     1.015
_refine_ls_number_reflns     8656
_refine_ls_number_parameters     441
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0380P)²+0.6302P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.444
_refine_diff_density_min     -0.457
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'O' 'O' 0.0106 0.0060
                         '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'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_reduction     'SAINT (Bruker, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)'
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_disorder_assembly
    _atom_site_disorder_group
    Br Br1A 0.18852(5) 0.84633(5) 0.56347(2) 0.08861(16) Uani d . 1 . .
    Br Br2A -0.11747(5) 0.62952(5) 0.47438(2) 0.08819(15) Uani d . 1 . .
    O O1A 0.1572(3) 1.0684(3) 0.35540(14) 0.0836(8) Uani d . 1 . .
    O O2A -0.0780(3) 0.9081(3) 0.29058(14) 0.0872(9) Uani d . 1 . .
    C C1A 0.0987(4) 0.8591(4) 0.47729(18) 0.0612(9) Uani d . 1 . .
    C C2A 0.1624(4) 0.9604(4) 0.44997(19) 0.0646(10) Uani d . 1 . .
    H H2A 0.2471 1.0193 0.4743 0.077 Uiso calc R 1 . .
    C C3A 0.1027(4) 0.9747(4) 0.38795(18) 0.0645(10) Uani d . 1 . .
    C C4A -0.0254(4) 0.8857(4) 0.35145(18) 0.0657(10) Uani d . 1 . .
    C C5A -0.0879(4) 0.7858(4) 0.37868(19) 0.0668(10) Uani d . 1 . .
    H H5A -0.1727 0.7269 0.3546 0.080 Uiso calc R 1 . .
    C C6A -0.0262(4) 0.7716(4) 0.44160(18) 0.0618(9) Uani d . 1 . .
    C C7A 0.2883(4) 1.1603(5) 0.3899(2) 0.0869(13) Uani d . 1 . .
    H H7AA 0.3152 1.2215 0.3626 0.130 Uiso calc R 1 . .
    H H7AB 0.3556 1.1069 0.3954 0.130 Uiso calc R 1 . .
    H H7AC 0.2821 1.2141 0.4348 0.130 Uiso calc R 1 . .
    C C8A -0.2073(4) 0.8181(6) 0.2512(2) 0.1095(18) Uani d . 1 . .
    H H8AA -0.2320 0.8416 0.2086 0.164 Uiso calc R 1 . .
    H H8AB -0.2770 0.8292 0.2779 0.164 Uiso calc R 1 . .
    H H8AC -0.1997 0.7232 0.2407 0.164 Uiso calc R 1 . .
    Br Br1B 0.51028(5) 0.84947(5) 0.39054(2) 0.09023(16) Uani d . 1 . .
    Br Br2B 0.40577(5) 0.60365(5) 0.46979(2) 0.08438(15) Uani d . 1 . .
    O O1B 0.0405(3) 0.6253(3) 0.21122(14) 0.0760(8) Uani d . 1 . .
    O O2B -0.0379(3) 0.4381(3) 0.27175(14) 0.0773(7) Uani d . 1 . .
    C C1B 0.3397(4) 0.7172(4) 0.35633(19) 0.0602(9) Uani d . 1 . .
    C C2B 0.2559(4) 0.7211(4) 0.29605(19) 0.0640(10) Uani d . 1 . .
    H H2B 0.2854 0.7874 0.2738 0.077 Uiso calc R 1 . .
    C C3B 0.1298(4) 0.6281(4) 0.26885(18) 0.0587(9) Uani d . 1 . .
    C C4B 0.0868(4) 0.5265(4) 0.30234(19) 0.0594(9) Uani d . 1 . .
    C C5B 0.1704(4) 0.5233(4) 0.36135(18) 0.0604(9) Uani d . 1 . .
    H H5B 0.1421 0.4564 0.3835 0.073 Uiso calc R 1 . .
    C C6B 0.2966(4) 0.6177(4) 0.38877(18) 0.0599(9) Uani d . 1 . .
    C C7B 0.0833(5) 0.7271(5) 0.1756(2) 0.0865(13) Uani d . 1 . .
    H H7BA 0.0120 0.7163 0.1361 0.130 Uiso calc R 1 . .
    H H7BB 0.1661 0.7138 0.1603 0.130 Uiso calc R 1 . .
    H H7BC 0.1003 0.8189 0.2068 0.130 Uiso calc R 1 . .
    C C8B -0.0872(4) 0.3350(4) 0.3047(2) 0.0772(11) Uani d . 1 . .
    H H8BA -0.1749 0.2779 0.2777 0.116 Uiso calc R 1 . .
    H H8BB -0.0971 0.3800 0.3505 0.116 Uiso calc R 1 . .
    H H8BC -0.0226 0.2780 0.3081 0.116 Uiso calc R 1 . .
    Br Br1C 0.15911(5) 0.45176(5) 0.02682(2) 0.09230(17) Uani d . 1 . .
    Br Br2C 0.47373(5) 0.65530(5) 0.11271(2) 0.08761(16) Uani d . 1 . .
    O O1C 0.1936(3) 0.2113(3) 0.22690(13) 0.0698(7) Uani d . 1 . .
    O O2C 0.4349(3) 0.3628(3) 0.29126(13) 0.0693(7) Uani d . 1 . .
    C C1C 0.2523(4) 0.4309(4) 0.11005(18) 0.0610(9) Uani d . 1 . .
    C C2C 0.1871(4) 0.3281(4) 0.13655(19) 0.0619(9) Uani d . 1 . .
    H H2C 0.1005 0.2725 0.1129 0.074 Uiso calc R 1 . .
    C C3C 0.2494(4) 0.3082(4) 0.19688(18) 0.0572(9) Uani d . 1 . .
    C C4C 0.3800(4) 0.3909(4) 0.23244(17) 0.0559(9) Uani d . 1 . .
    C C5C 0.4440(4) 0.4937(4) 0.20656(18) 0.0585(9) Uani d . 1 . .
    H H5C 0.5303 0.5502 0.2302 0.070 Uiso calc R 1 . .
    C C6C 0.3789(4) 0.5125(4) 0.14515(19) 0.0595(9) Uani d . 1 . .
    C C7C 0.0615(4) 0.1217(4) 0.1909(2) 0.0764(11) Uani d . 1 . .
    H H7CA 0.0294 0.0632 0.2185 0.115 Uiso calc R 1 . .
    H H7CB 0.0696 0.0648 0.1470 0.115 Uiso calc R 1 . .
    H H7CC -0.0028 0.1771 0.1830 0.115 Uiso calc R 1 . .
    C C8C 0.5725(4) 0.4376(5) 0.3258(2) 0.0782(12) Uani d . 1 . .
    H H8CA 0.6008 0.4056 0.3652 0.117 Uiso calc R 1 . .
    H H8CB 0.5761 0.5352 0.3411 0.117 Uiso calc R 1 . .
    H H8CC 0.6331 0.4222 0.2941 0.117 Uiso calc R 1 . .
    Br Br1D 0.13475(5) -0.12779(5) 0.02042(2) 0.08027(14) Uani d . 1 . .
    Br Br2D 0.26373(5) 0.09162(5) -0.06800(2) 0.08695(15) Uani d . 1 . .
    O O1D 0.5780(3) 0.1239(3) 0.21456(13) 0.0792(8) Uani d . 1 . .
    O O2D 0.6751(3) 0.2925(3) 0.14934(13) 0.0783(8) Uani d . 1 . .
    C C1D 0.3045(4) 0.0067(4) 0.05654(18) 0.0573(9) Uani d . 1 . .
    C C2D 0.3764(4) 0.0138(4) 0.12185(18) 0.0602(9) Uani d . 1 . .
    H H2D 0.3411 -0.0468 0.1459 0.072 Uiso calc R 1 . .
    C C3D 0.4984(4) 0.1094(4) 0.15087(18) 0.0608(9) Uani d . 1 . .
    C C4D 0.5534(4) 0.2009(4) 0.11520(18) 0.0618(9) Uani d . 1 . .
    C C5D 0.4818(4) 0.1936(4) 0.05073(18) 0.0620(9) Uani d . 1 . .
    H H5D 0.5171 0.2538 0.0265 0.074 Uiso calc R 1 . .
    C C6D 0.3564(4) 0.0962(4) 0.02122(18) 0.0596(9) Uani d . 1 . .
    C C7D 0.5192(5) 0.0460(5) 0.2567(2) 0.0939(15) Uani d . 1 . .
    H H7DA 0.5817 0.0683 0.3008 0.141 Uiso calc R 1 . .
    H H7DB 0.5026 -0.0517 0.2338 0.141 Uiso calc R 1 . .
    H H7DC 0.4338 0.0688 0.2638 0.141 Uiso calc R 1 . .
    C C8D 0.7344(4) 0.3886(4) 0.1158(2) 0.0839(12) Uani d . 1 . .
    H H8DA 0.8199 0.4464 0.1450 0.126 Uiso calc R 1 . .
    H H8DB 0.6723 0.4457 0.1071 0.126 Uiso calc R 1 . .
    H H8DC 0.7512 0.3387 0.0724 0.126 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    Br1A C1A . 1.887(3) ?
    Br2A C6A . 1.883(4) ?
    O1A C3A . 1.369(4) ?
    O1A C7A . 1.429(5) ?
    O2A C4A . 1.356(4) ?
    O2A C8A . 1.431(5) ?
    C1A C6A . 1.373(5) ?
    C1A C2A . 1.388(5) ?
    C2A C3A . 1.362(5) ?
    C2A H2A . 0.9300 ?
    C3A C4A . 1.405(5) ?
    C4A C5A . 1.371(5) ?
    C5A C6A . 1.384(5) ?
    C5A H5A . 0.9300 ?
    C7A H7AA . 0.9600 ?
    C7A H7AB . 0.9600 ?
    C7A H7AC . 0.9600 ?
    C8A H8AA . 0.9600 ?
    C8A H8AB . 0.9600 ?
    C8A H8AC . 0.9600 ?
    Br1B C1B . 1.886(4) ?
    Br2B C6B . 1.885(3) ?
    O1B C3B . 1.352(4) ?
    O1B C7B . 1.442(5) ?
    O2B C4B . 1.355(4) ?
    O2B C8B . 1.431(4) ?
    C1B C6B . 1.379(5) ?
    C1B C2B . 1.389(5) ?
    C2B C3B . 1.376(5) ?
    C2B H2B . 0.9300 ?
    C3B C4B . 1.410(5) ?
    C4B C5B . 1.365(5) ?
    C5B C6B . 1.383(5) ?
    C5B H5B . 0.9300 ?
    C7B H7BA . 0.9600 ?
    C7B H7BB . 0.9600 ?
    C7B H7BC . 0.9600 ?
    C8B H8BA . 0.9600 ?
    C8B H8BB . 0.9600 ?
    C8B H8BC . 0.9600 ?
    Br1C C1C . 1.881(3) ?
    Br2C C6C . 1.899(4) ?
    O1C C3C . 1.361(4) ?
    O1C C7C . 1.434(4) ?
    O2C C4C . 1.355(4) ?
    O2C C8C . 1.428(4) ?
    C1C C6C . 1.363(5) ?
    C1C C2C . 1.395(5) ?
    C2C C3C . 1.366(5) ?
    C2C H2C . 0.9300 ?
    C3C C4C . 1.398(5) ?
    C4C C5C . 1.383(5) ?
    C5C C6C . 1.389(5) ?
    C5C H5C . 0.9300 ?
    C7C H7CA . 0.9600 ?
    C7C H7CB . 0.9600 ?
    C7C H7CC . 0.9600 ?
    C8C H8CA . 0.9600 ?
    C8C H8CB . 0.9600 ?
    C8C H8CC . 0.9600 ?
    Br1D C1D . 1.893(4) ?
    Br2D C6D . 1.889(3) ?
    O1D C3D . 1.369(4) ?
    O1D C7D . 1.423(5) ?
    O2D C4D . 1.358(4) ?
    O2D C8D . 1.420(5) ?
    C1D C6D . 1.370(5) ?
    C1D C2D . 1.386(5) ?
    C2D C3D . 1.362(5) ?
    C2D H2D . 0.9300 ?
    C3D C4D . 1.401(5) ?
    C4D C5D . 1.369(5) ?
    C5D C6D . 1.394(5) ?
    C5D H5D . 0.9300 ?
    C7D H7DA . 0.9600 ?
    C7D H7DB . 0.9600 ?
    C7D H7DC . 0.9600 ?
    C8D H8DA . 0.9600 ?
    C8D H8DB . 0.9600 ?
    C8D H8DC . 0.9600 ?
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
    C3A O1A C7A . . 117.0(3) ?
    C4A O2A C8A . . 117.1(3) ?
    C6A C1A C2A . . 119.9(3) ?
    C6A C1A Br1A . . 121.9(3) ?
    C2A C1A Br1A . . 118.2(3) ?
    C3A C2A C1A . . 120.9(4) ?
    C3A C2A H2A . . 119.5 ?
    C1A C2A H2A . . 119.5 ?
    C2A C3A O1A . . 126.0(4) ?
    C2A C3A C4A . . 119.3(4) ?
    O1A C3A C4A . . 114.7(3) ?
    O2A C4A C5A . . 125.1(4) ?
    O2A C4A C3A . . 115.4(3) ?
    C5A C4A C3A . . 119.5(3) ?
    C4A C5A C6A . . 120.8(4) ?
    C4A C5A H5A . . 119.6 ?
    C6A C5A H5A . . 119.6 ?
    C1A C6A C5A . . 119.5(4) ?
    C1A C6A Br2A . . 122.4(3) ?
    C5A C6A Br2A . . 118.1(3) ?
    O1A C7A H7AA . . 109.5 ?
    O1A C7A H7AB . . 109.5 ?
    H7AA C7A H7AB . . 109.5 ?
    O1A C7A H7AC . . 109.5 ?
    H7AA C7A H7AC . . 109.5 ?
    H7AB C7A H7AC . . 109.5 ?
    O2A C8A H8AA . . 109.5 ?
    O2A C8A H8AB . . 109.5 ?
    H8AA C8A H8AB . . 109.5 ?
    O2A C8A H8AC . . 109.5 ?
    H8AA C8A H8AC . . 109.5 ?
    H8AB C8A H8AC . . 109.5 ?
    C3B O1B C7B . . 116.7(3) ?
    C4B O2B C8B . . 117.4(3) ?
    C6B C1B C2B . . 119.5(3) ?
    C6B C1B Br1B . . 122.4(3) ?
    C2B C1B Br1B . . 118.1(3) ?
    C3B C2B C1B . . 120.9(3) ?
    C3B C2B H2B . . 119.6 ?
    C1B C2B H2B . . 119.6 ?
    O1B C3B C2B . . 125.0(3) ?
    O1B C3B C4B . . 115.8(3) ?
    C2B C3B C4B . . 119.2(3) ?
    O2B C4B C5B . . 125.2(3) ?
    O2B C4B C3B . . 115.4(3) ?
    C5B C4B C3B . . 119.4(3) ?
    C4B C5B C6B . . 121.1(3) ?
    C4B C5B H5B . . 119.4 ?
    C6B C5B H5B . . 119.4 ?
    C1B C6B C5B . . 119.9(3) ?
    C1B C6B Br2B . . 122.0(3) ?
    C5B C6B Br2B . . 118.1(3) ?
    O1B C7B H7BA . . 109.5 ?
    O1B C7B H7BB . . 109.5 ?
    H7BA C7B H7BB . . 109.5 ?
    O1B C7B H7BC . . 109.5 ?
    H7BA C7B H7BC . . 109.5 ?
    H7BB C7B H7BC . . 109.5 ?
    O2B C8B H8BA . . 109.5 ?
    O2B C8B H8BB . . 109.5 ?
    H8BA C8B H8BB . . 109.5 ?
    O2B C8B H8BC . . 109.5 ?
    H8BA C8B H8BC . . 109.5 ?
    H8BB C8B H8BC . . 109.5 ?
    C3C O1C C7C . . 116.9(3) ?
    C4C O2C C8C . . 117.4(3) ?
    C6C C1C C2C . . 119.4(3) ?
    C6C C1C Br1C . . 122.7(3) ?
    C2C C1C Br1C . . 117.9(3) ?
    C3C C2C C1C . . 120.6(3) ?
    C3C C2C H2C . . 119.7 ?
    C1C C2C H2C . . 119.7 ?
    O1C C3C C2C . . 124.8(3) ?
    O1C C3C C4C . . 115.2(3) ?
    C2C C3C C4C . . 120.0(3) ?
    O2C C4C C5C . . 124.5(3) ?
    O2C C4C C3C . . 116.0(3) ?
    C5C C4C C3C . . 119.5(3) ?
    C4C C5C C6C . . 119.7(3) ?
    C4C C5C H5C . . 120.1 ?
    C6C C5C H5C . . 120.1 ?
    C1C C6C C5C . . 120.9(3) ?
    C1C C6C Br2C . . 121.9(3) ?
    C5C C6C Br2C . . 117.3(3) ?
    O1C C7C H7CA . . 109.5 ?
    O1C C7C H7CB . . 109.5 ?
    H7CA C7C H7CB . . 109.5 ?
    O1C C7C H7CC . . 109.5 ?
    H7CA C7C H7CC . . 109.5 ?
    H7CB C7C H7CC . . 109.5 ?
    O2C C8C H8CA . . 109.5 ?
    O2C C8C H8CB . . 109.5 ?
    H8CA C8C H8CB . . 109.5 ?
    O2C C8C H8CC . . 109.5 ?
    H8CA C8C H8CC . . 109.5 ?
    H8CB C8C H8CC . . 109.5 ?
    C3D O1D C7D . . 116.8(3) ?
    C4D O2D C8D . . 117.8(3) ?
    C6D C1D C2D . . 119.9(3) ?
    C6D C1D Br1D . . 122.7(3) ?
    C2D C1D Br1D . . 117.4(3) ?
    C3D C2D C1D . . 120.1(3) ?
    C3D C2D H2D . . 119.9 ?
    C1D C2D H2D . . 119.9 ?
    C2D C3D O1D . . 124.7(3) ?
    C2D C3D C4D . . 120.7(3) ?
    O1D C3D C4D . . 114.6(3) ?
    O2D C4D C5D . . 125.5(4) ?
    O2D C4D C3D . . 115.6(3) ?
    C5D C4D C3D . . 118.9(3) ?
    C4D C5D C6D . . 120.4(3) ?
    C4D C5D H5D . . 119.8 ?
    C6D C5D H5D . . 119.8 ?
    C1D C6D C5D . . 120.0(3) ?
    C1D C6D Br2D . . 121.9(3) ?
    C5D C6D Br2D . . 118.0(3) ?
    O1D C7D H7DA . . 109.5 ?
    O1D C7D H7DB . . 109.5 ?
    H7DA C7D H7DB . . 109.5 ?
    O1D C7D H7DC . . 109.5 ?
    H7DA C7D H7DC . . 109.5 ?
    H7DB C7D H7DC . . 109.5 ?
    O2D C8D H8DA . . 109.5 ?
    O2D C8D H8DB . . 109.5 ?
    H8DA C8D H8DB . . 109.5 ?
    O2D C8D H8DC . . 109.5 ?
    H8DA C8D H8DC . . 109.5 ?
    H8DB C8D H8DC . . 109.5 ?
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
    C7A H7AA O2C 1_565 0.96 2.56 3.498(5) 167.2
    C8D H8DA O1B 1_655 0.96 2.53 3.485(5) 171.0
data_II
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1,2-Diiodo-4,5-dimethoxybenzene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H8 I2 O2'
_chemical_formula_sum     'C8 H8 I2 O2'
_chemical_formula_iupac     'C8 H8 I2 O2'
_chemical_formula_weight     389.94
_chemical_melting_point     404.0(10)
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     8.993(4)
_cell_length_b     13.882(9)
_cell_length_c     16.506(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2060.7(17)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     7.5
_cell_measurement_theta_max     17.5
_cell_measurement_temperature     294(2)
_exptl_crystal_description     blocks
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     2.514
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1424
_exptl_absorpt_coefficient_mu     6.065
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.18
_exptl_absorpt_correction_T_max     0.38
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device     "Rigaku AFC6 difractometer"
_diffrn_measurement_method     ω/2θ
_diffrn_reflns_number     2652
_diffrn_reflns_av_R_equivalents     0.0392
_diffrn_reflns_av_sigmaI/netI     0.0560
_diffrn_reflns_theta_min     2.47
_diffrn_reflns_theta_max     25.99
_diffrn_reflns_theta_full     25.99
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -1
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -1
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -1
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     3
_diffrn_standards_interval_count     150
_diffrn_standards_decay_%     <2
_reflns_number_total     2023
_reflns_number_gt     1441
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0752
_refine_ls_R_factor_gt     0.0419
_refine_ls_wR_factor_gt     0.1029
_refine_ls_wR_factor_ref     0.1083
_refine_ls_goodness_of_fit_ref     1.411
_refine_ls_restrained_S_all     1.411
_refine_ls_number_reflns     2023
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0345P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.819
_refine_diff_density_min     -0.764
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.0159(6)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'I' 'I' -0.4742 1.8119
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure
Corporation, 1988)
;
_computing_cell_refinement
;
MSC/AFC Diffractometer Control Software (Molecular Structure
Corporation, 1988)
;
_computing_data_reduction
;
MSC/AFC Diffractometer Control Software (Molecular Structure
Corporation, 1988)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)'
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_disorder_assembly
    _atom_site_disorder_group
    I I1 0.08039(8) 0.74558(4) 0.55011(4) 0.0553(3) Uani d . 1 . .
    I I2 0.31872(6) 0.53741(4) 0.59939(3) 0.0433(2) Uani d . 1 . .
    O O1 -0.0021(6) 0.5609(4) 0.2648(3) 0.0420(13) Uani d . 1 . .
    O O2 0.1706(6) 0.4178(4) 0.2970(3) 0.0437(13) Uani d . 1 . .
    C C1 0.1135(8) 0.6290(5) 0.4722(4) 0.0305(16) Uani d . 1 . .
    C C2 0.0389(8) 0.6337(5) 0.3974(4) 0.0343(16) Uani d . 1 . .
    H H2 -0.0246 0.6849 0.3862 0.041 Uiso calc R 1 . .
    C C3 0.0605(7) 0.5616(6) 0.3403(4) 0.0334(16) Uani d . 1 . .
    C C4 0.1547(8) 0.4835(5) 0.3572(4) 0.0305(16) Uani d . 1 . .
    C C5 0.2286(8) 0.4803(5) 0.4318(4) 0.0334(17) Uani d . 1 . .
    H H5 0.2928 0.4295 0.4431 0.040 Uiso calc R 1 . .
    C C6 0.2070(8) 0.5521(6) 0.4891(4) 0.0342(17) Uani d . 1 . .
    C C7 -0.0979(9) 0.6405(6) 0.2433(5) 0.049(2) Uani d . 1 . .
    H H7A -0.1316 0.6326 0.1885 0.074 Uiso calc R 1 . .
    H H7B -0.0436 0.6998 0.2479 0.074 Uiso calc R 1 . .
    H H7C -0.1819 0.6419 0.2791 0.074 Uiso calc R 1 . .
    C C8 0.2883(10) 0.3511(6) 0.3043(5) 0.049(2) Uani d . 1 . .
    H H8A 0.2903 0.3101 0.2575 0.073 Uiso calc R 1 . .
    H H8B 0.2738 0.3126 0.3520 0.073 Uiso calc R 1 . .
    H H8C 0.3809 0.3851 0.3085 0.073 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    I1 C1 . 2.089(7) ?
    I2 C6 . 2.090(7) ?
    O1 C3 . 1.366(8) ?
    O1 C7 . 1.446(10) ?
    O2 C4 . 1.356(9) ?
    O2 C8 . 1.412(9) ?
    C1 C6 . 1.387(10) ?
    C1 C2 . 1.408(10) ?
    C2 C3 . 1.389(10) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.404(10) ?
    C4 C5 . 1.401(10) ?
    C5 C6 . 1.387(11) ?
    C5 H5 . 0.9300 ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
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
    C3 O1 C7 . . 117.7(6) ?
    C4 O2 C8 . . 117.2(6) ?
    C6 C1 C2 . . 120.1(6) ?
    C6 C1 I1 . . 124.0(5) ?
    C2 C1 I1 . . 115.8(5) ?
    C3 C2 C1 . . 119.7(6) ?
    C3 C2 H2 . . 120.2 ?
    C1 C2 H2 . . 120.2 ?
    O1 C3 C2 . . 124.5(7) ?
    O1 C3 C4 . . 115.1(6) ?
    C2 C3 C4 . . 120.4(6) ?
    O2 C4 C5 . . 124.9(6) ?
    O2 C4 C3 . . 115.9(6) ?
    C5 C4 C3 . . 119.1(6) ?
    C6 C5 C4 . . 120.6(7) ?
    C6 C5 H5 . . 119.7 ?
    C4 C5 H5 . . 119.7 ?
    C1 C6 C5 . . 120.1(7) ?
    C1 C6 I2 . . 122.7(5) ?
    C5 C6 I2 . . 117.1(5) ?
    O1 C7 H7A . . 109.5 ?
    O1 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    O1 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    O2 C8 H8A . . 109.5 ?
    O2 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    O2 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
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
    C7 H7A Cg1 6_556 0.96 2.90 3.747(8) 147.2
