#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/68/2016848.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_2016848
loop_
_publ_author_name
'Cukiernik, Fabio D.'
'Zelcer, Andrés'
'Garland, Maria Teresa'
'Baggio, Ricardo'
_publ_section_title
;
 Halogen bonding in 1,2-dibromo-4,5-dimethoxybenzene and
 1,2-diiodo-4,5-dimethoxybenzene
;
_journal_coeditor_code           UK3001
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o604
_journal_page_last               o608
_journal_paper_doi               10.1107/S010827010803309X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C8 H8 I2 O2'
_chemical_formula_moiety         'C8 H8 I2 O2'
_chemical_formula_sum            'C8 H8 I2 O2'
_chemical_formula_weight         389.94
_chemical_melting_point          404.0(10)
_chemical_name_systematic
;
1,2-Diiodo-4,5-dimethoxybenzene
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.993(4)
_cell_length_b                   13.882(9)
_cell_length_c                   16.506(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      17.5
_cell_measurement_theta_min      7.5
_cell_volume                     2060.6(17)
_computing_cell_refinement
;
MSC/AFC Diffractometer Control Software (Molecular Structure
Corporation, 1988)
;
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure
Corporation, 1988)
;
_computing_data_reduction
;
MSC/AFC Diffractometer Control Software (Molecular Structure
Corporation, 1988)
;
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Rigaku AFC6 difractometer'
_diffrn_measurement_method       ω/2θ
_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  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2652
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.47
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    6.065
_exptl_absorpt_correction_T_max  0.38
_exptl_absorpt_correction_T_min  0.18
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.819
_refine_diff_density_min         -0.764
_refine_ls_extinction_coef       0.0159(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.411
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.411
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0345P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                1441
_reflns_number_total             2023
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            uk3001.cif
_cod_data_source_block           II
_cod_original_cell_volume        2060.7(17)
_cod_database_code               2016848
_cod_database_fobs_code          2016848
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'
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
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
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
I1 0.0778(5) 0.0460(4) 0.0419(4) 0.0067(3) 0.0007(3) -0.0115(3)
I2 0.0490(4) 0.0532(4) 0.0277(3) -0.0079(3) -0.0105(2) 0.0019(2)
O1 0.044(3) 0.053(3) 0.028(2) 0.004(3) -0.008(2) 0.004(2)
O2 0.052(3) 0.050(3) 0.029(3) 0.008(3) -0.006(2) -0.012(3)
C1 0.030(4) 0.030(3) 0.032(4) -0.007(3) 0.001(3) 0.001(3)
C2 0.033(4) 0.036(4) 0.033(4) 0.005(3) 0.003(3) -0.001(3)
C3 0.027(3) 0.051(4) 0.022(3) -0.008(3) 0.004(3) 0.007(3)
C4 0.035(4) 0.032(4) 0.025(3) -0.002(3) 0.002(3) 0.004(3)
C5 0.037(4) 0.038(4) 0.025(4) 0.003(3) -0.004(3) -0.002(3)
C6 0.039(4) 0.044(4) 0.020(3) -0.009(3) 0.003(3) 0.003(3)
C7 0.046(5) 0.055(5) 0.047(5) -0.011(4) -0.011(4) 0.016(4)
C8 0.058(5) 0.046(5) 0.043(4) 0.014(4) -0.001(4) -0.010(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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3307649
