#------------------------------------------------------------------------------
#$Date: 2015-12-09 16:30:23 +0100 (Wed 09 de Dec de 2015) $
#$Revision: 171310 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/50/7055074.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7055074
loop_
_publ_author_name
'Hettstedt, Christina'
'Mayer, Peter'
'Karaghiosoff, Konstantin'
_publ_section_title
;
 Halogen bonding in the crystal structures of 1,2-diiodo alkenes
;
_journal_issue                   11
_journal_name_full               'New J. Chem.'
_journal_page_first              8522
_journal_paper_doi               10.1039/C5NJ00821B
_journal_volume                  39
_journal_year                    2015
_chemical_formula_moiety         'C6 H6 I2 O4'
_chemical_formula_sum            'C6 H6 I2 O4'
_chemical_formula_weight         395.91
_chemical_name_systematic
;
 dimethyl 2,3-diiodofumarate
;
_chemical_properties_physical    Light-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-12-02 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.798(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6795(4)
_cell_length_b                   7.5937(2)
_cell_length_c                   8.5520(4)
_cell_measurement_reflns_used    3759
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.4633
_cell_measurement_theta_min      4.7733
_cell_volume                     533.59(4)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_molecular_graphics
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
;
_computing_publication_material
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_laue_measured_fraction_full 0.995
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5167
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         4.844
_exptl_absorpt_coefficient_mu    5.871
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.464
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethylacetate'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         1052
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0174
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0263P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0420
_refine_ls_wR_factor_ref         0.0427
_reflns_Friedel_coverage         0.000
_reflns_number_gt                923
_reflns_number_total             1052
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5nj00821b2.cif
_cod_data_source_block           lsg_k
_cod_depositor_comments
'Adding full bibliography for 7055070--7055078.cif.'
_cod_database_code               7055074
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.386
_shelx_estimated_absorpt_t_max   0.591
_shelxl_version_number           2013-2
_shelx_res_file
;
TITL lsg_k in P2(1)/c
CELL  0.71073   8.6795   7.5937   8.5520   90.000  108.798   90.000
ZERR     2.00   0.0004   0.0002   0.0004    0.000    0.005    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    O    I
UNIT  12   12   8    4
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
MERG   2
OMIT    -2.00  52.00
EADP C2A C2
FMAP   2
PLAN   25
ACTA
BOND   $H
CONF
L.S.   4
SIZE 0.20 0.20 0.10
TEMP  -173.00
WGHT    0.026300
FVAR       0.43849   0.22060
PART    1
C2A   1    0.978460   -0.068083    0.453821    21.00000    0.02133    0.01421 =
         0.01701    0.00023    0.00964   -0.00089
PART    2
C2    1    0.922337    0.017871    0.487337   -21.00000    0.02133    0.01421 =
         0.01701    0.00023    0.00964   -0.00089
PART    0
C3    1    0.611640   -0.330759    0.345201    11.00000    0.02800    0.02701 =
         0.03487    0.00063    0.00354   -0.01454
AFIX 137
H3A   2    0.515864   -0.253893    0.316237    11.00000   -1.50000
H3B   2    0.594373   -0.430911    0.409896    11.00000   -1.50000
H3C   2    0.628747   -0.373875    0.244045    11.00000   -1.50000
AFIX   0
MOLE    1
I1    4    0.851436    0.234054    0.603249    11.00000    0.02108    0.01974 =
         0.02218   -0.00395    0.00931    0.00378
O2    3    0.753862   -0.232322    0.442192    11.00000    0.02567    0.03611 =
         0.02927    0.01601   -0.00062   -0.01383
O1    3    0.709403   -0.034112    0.240821    11.00000    0.02235    0.02236 =
         0.02640    0.00526    0.00289   -0.00263
C1    1    0.786615   -0.088609    0.372699    11.00000    0.02107    0.02387 =
         0.01862    0.00251    0.00718   -0.00455
HKLF    4

REM  lsg_k in P2(1)/c
REM R1 =  0.0174 for     923 Fo > 4sig(Fo)  and  0.0211 for all    1052 data
REM     60 parameters refined using      0 restraints

END

WGHT      0.0263      0.0000

REM Highest difference peak  0.671,  deepest hole -0.499,  1-sigma level  0.102
Q1    1   0.8960  0.2301  0.7167  11.00000  0.05    0.67
Q2    1   0.9574  0.2416  0.6089  11.00000  0.05    0.66
Q3    1   0.7500  0.2191  0.6116  11.00000  0.05    0.62
Q4    1   0.5416 -0.2644  0.2975  11.00000  0.05    0.46
Q5    1   0.8018  0.2297  0.4828  11.00000  0.05    0.46
Q6    1   0.7629 -0.3257  0.3823  11.00000  0.05    0.42
Q7    1   0.8557  0.3577  0.6050  11.00000  0.05    0.40
Q8    1   0.7137  0.2519  0.5083  11.00000  0.05    0.35
Q9    1   0.8564  0.1002  0.5232  11.00000  0.05    0.31
Q10   1   0.4819 -0.2425  0.5131  11.00000  0.05    0.29
Q11   1   0.8327 -0.2188  0.1994  11.00000  0.05    0.28
Q12   1   0.4234 -0.2570  0.0868  11.00000  0.05    0.27
Q13   1   1.0464  0.2596  0.7367  11.00000  0.05    0.27
Q14   1   0.9949 -0.1660  0.5804  11.00000  0.05    0.24
Q15   1   0.5616 -0.3528  0.4151  11.00000  0.05    0.23
Q16   1   0.6810  0.0029  0.3012  11.00000  0.05    0.23
Q17   1   0.7163 -0.4116  0.2563  11.00000  0.05    0.22
Q18   1   0.7995 -0.1663  0.3602  11.00000  0.05    0.22
Q19   1   0.9906 -0.2731  0.5369  11.00000  0.05    0.22
Q20   1   0.9937 -0.3557  0.5641  11.00000  0.05    0.21
Q21   1   0.3806 -0.2713  0.4447  11.00000  0.05    0.21
Q22   1   0.9999 -0.0431  0.5540  11.00000  0.05    0.20
Q23   1   0.6691 -0.1598  0.5642  11.00000  0.05    0.20
Q24   1   0.5570 -0.0348  0.0978  11.00000  0.05    0.20
Q25   1   0.5996 -0.4691  0.0820  11.00000  0.05    0.20
;
_shelx_res_checksum              30966
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.9785(19) -0.0681(18) 0.4538(17) 0.0167(9) Uani 0.221(7) 1 d . . P A 1
C1 C 0.9223(5) 0.0179(5) 0.4873(4) 0.0167(9) Uani 0.779(7) 1 d . . P A 2
C3 C 0.6116(4) -0.3308(5) 0.3452(4) 0.0315(8) Uani 1 1 d . . . . .
H3A H 0.5159 -0.2539 0.3162 0.047 Uiso 1 1 calc R U . . .
H3B H 0.5944 -0.4309 0.4099 0.047 Uiso 1 1 calc R U . . .
H3C H 0.6287 -0.3739 0.2440 0.047 Uiso 1 1 calc R U . . .
I1 I 0.85144(2) 0.23405(2) 0.60325(2) 0.02044(9) Uani 1 1 d . . . . .
O2 O 0.7539(3) -0.2323(3) 0.4422(3) 0.0326(6) Uani 1 1 d . . . . .
O1 O 0.7094(3) -0.0341(3) 0.2408(3) 0.0249(5) Uani 1 1 d . . . . .
C2 C 0.7866(4) -0.0886(4) 0.3727(4) 0.0210(7) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1A 0.021(2) 0.014(2) 0.017(2) 0.0002(15) 0.0096(17) -0.0009(15)
C1 0.021(2) 0.014(2) 0.017(2) 0.0002(15) 0.0096(17) -0.0009(15)
C3 0.0280(19) 0.0270(18) 0.0349(19) 0.0006(15) 0.0035(15) -0.0145(15)
I1 0.02108(14) 0.01974(13) 0.02218(13) -0.00395(8) 0.00931(9) 0.00378(8)
O2 0.0257(13) 0.0361(14) 0.0293(13) 0.0160(10) -0.0006(11) -0.0138(10)
O1 0.0224(12) 0.0224(11) 0.0264(12) 0.0053(9) 0.0029(10) -0.0026(9)
C2 0.0211(17) 0.0239(16) 0.0186(16) 0.0025(12) 0.0072(14) -0.0046(13)
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1A C1A C2 113.8(17) 3_756 .
C1A C1A I1 122.4(17) 3_756 3_756
C2 C1A I1 123.5(8) . 3_756
C1 C1 C2 122.7(4) 3_756 .
C1 C1 I1 121.3(4) 3_756 .
C2 C1 I1 116.1(3) . .
O2 C3 H3A 109.5 . .
O2 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
O2 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C2 O2 C3 115.9(3) . .
O1 C2 O2 125.5(3) . .
O1 C2 C1 121.1(3) . .
O2 C2 C1 112.9(3) . .
O1 C2 C1A 124.9(5) . .
O2 C2 C1A 103.4(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1A C1A 1.28(3) 3_756
C1A C2 1.592(16) .
C1A I1 2.114(15) 3_756
C1 C1 1.323(8) 3_756
C1 C2 1.503(5) .
C1 I1 2.109(4) .
C3 O2 1.453(4) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
I1 C1A 2.114(15) 3_756
O2 C2 1.317(3) .
O1 C2 1.185(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
_geom_torsion_site_symmetry_1
C3 O2 C2 O1 0.8(5) .
C3 O2 C2 C1 173.0(3) .
C3 O2 C2 C1A -152.3(6) .
C1 C1 C2 O1 -104.7(5) 3_756
I1 C1 C2 O1 73.9(4) .
C1 C1 C2 O2 82.8(5) 3_756
I1 C1 C2 O2 -98.6(3) .
C1 C1 C2 C1A 2.8(9) 3_756
I1 C1 C2 C1A -178.6(9) .
C1A C1A C2 O1 92.8(15) 3_756
I1 C1A C2 O1 -81.3(9) 3_756
C1A C1A C2 O2 -113.8(15) 3_756
I1 C1A C2 O2 72.1(8) 3_756
C1A C1A C2 C1 -2.7(8) 3_756
I1 C1A C2 C1 -176.7(15) 3_756
