# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_test1
_database_code_depnum_ccdc_archive 'CCDC 988931'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(E)-(3,3-diethoxy-1,2-diiodoprop-1-en-1-yl)benzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 I2 O2'
_chemical_formula_sum            'C13 H16 I2 O2'
_chemical_formula_weight         458.06

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.7818(7)
_cell_length_b                   10.2566(6)
_cell_length_c                   14.5072(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.917(7)
_cell_angle_gamma                90.00
_cell_volume                     1508.32(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3151
_cell_measurement_theta_min      4.2730
_cell_measurement_theta_max      31.7090

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.021
_exptl_crystal_density_meas      .
_exptl_crystal_density_diffrn    2.017
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    4.159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            13331
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.25
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3719
_reflns_number_gt                2919
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0214P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3719
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0656
_refine_ls_wR_factor_gt          0.0593
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.27508(2) 0.22586(2) 0.686800(18) 0.01852(8) Uani 1 1 d . . .
I2 I 0.55699(3) 0.29154(3) 0.476103(19) 0.02620(9) Uani 1 1 d . . .
O1 O 0.1511(2) 0.1594(2) 0.45158(19) 0.0198(6) Uani 1 1 d . . .
C8 C 0.6163(4) 0.1238(4) 0.7332(3) 0.0194(8) Uani 1 1 d . . .
H8 H 0.566(2) 0.048(3) 0.7043(12) 0.023 Uiso 1 1 calc R . .
O2 O 0.1758(3) 0.3794(2) 0.46906(18) 0.0190(6) Uani 1 1 d . . .
C1 C 0.3505(4) 0.2510(4) 0.5705(3) 0.0188(8) Uani 1 1 d . . .
C6 C 0.7943(4) 0.2223(4) 0.8630(3) 0.0222(9) Uani 1 1 d . . .
H6 H 0.866(3) 0.2145(5) 0.922(3) 0.027 Uiso 1 1 calc R . .
C13 C 0.0986(4) -0.0603(4) 0.4009(3) 0.0338(11) Uani 1 1 d . . .
H13A H 0.1346(12) -0.144(2) 0.386(2) 0.051 Uiso 1 1 calc R . .
H13B H 0.025(2) -0.0302(15) 0.3415(19) 0.051 Uiso 1 1 calc R . .
H13C H 0.064(2) -0.073(2) 0.4560(16) 0.051 Uiso 1 1 calc R . .
C5 C 0.7620(4) 0.3427(4) 0.8182(3) 0.0244(9) Uani 1 1 d . . .
H5 H 0.813(2) 0.421(3) 0.8489(14) 0.029 Uiso 1 1 calc R . .
C7 C 0.7210(4) 0.1136(4) 0.8211(3) 0.0225(9) Uani 1 1 d . . .
H7 H 0.7408(10) 0.038(4) 0.8501(14) 0.027 Uiso 1 1 calc R . .
C12 C 0.2054(4) 0.0400(4) 0.4293(3) 0.0293(10) Uani 1 1 d . . .
H12A H 0.277(2) 0.0110(10) 0.4856(17) 0.035 Uiso 1 1 calc R . .
H12B H 0.2385(12) 0.0538(5) 0.3764(16) 0.035 Uiso 1 1 calc R . .
C11 C 0.0506(4) 0.5568(4) 0.3773(3) 0.0240(9) Uani 1 1 d . . .
H11A H 0.003(2) 0.5876(13) 0.3135(15) 0.036 Uiso 1 1 calc R . .
H11B H 0.1211(16) 0.6144(15) 0.4082(19) 0.036 Uiso 1 1 calc R . .
H11C H -0.006(2) 0.5524(6) 0.4143(19) 0.036 Uiso 1 1 calc R . .
C10 C 0.1046(4) 0.4231(4) 0.3707(3) 0.0195(8) Uani 1 1 d . . .
H10A H 0.034(2) 0.3645(17) 0.3394(10) 0.023 Uiso 1 1 calc R . .
H10B H 0.1619(16) 0.4264(4) 0.3333(11) 0.023 Uiso 1 1 calc R . .
C3 C 0.5848(3) 0.2443(4) 0.6874(3) 0.0175(8) Uani 1 1 d . . .
C4 C 0.6581(4) 0.3540(4) 0.7301(3) 0.0216(8) Uani 1 1 d . . .
H4 H 0.6383(10) 0.432(4) 0.7006(14) 0.026 Uiso 1 1 calc R . .
C9 C 0.2428(4) 0.2631(3) 0.4714(3) 0.0156(8) Uani 1 1 d . . .
H9 H 0.2807(17) 0.2651(4) 0.424(2) 0.019 Uiso 1 1 calc R . .
C2 C 0.4786(4) 0.2576(4) 0.5904(3) 0.0178(8) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.124(4) . ?
I2 C2 2.131(4) . ?
O1 C9 1.412(4) . ?
O1 C12 1.441(4) . ?
C8 C3 1.389(5) . ?
C8 C7 1.390(5) . ?
C8 H8 0.9551 . ?
O2 C9 1.390(4) . ?
O2 C10 1.442(4) . ?
C1 C2 1.313(5) . ?
C1 C9 1.514(5) . ?
C6 C7 1.382(5) . ?
C6 C5 1.384(6) . ?
C6 H6 0.9379 . ?
C13 C12 1.494(6) . ?
C13 H13A 0.9980 . ?
C13 H13B 0.9980 . ?
C13 H13C 0.9980 . ?
C5 C4 1.388(5) . ?
C5 H5 0.9859 . ?
C7 H7 0.8773 . ?
C12 H12A 0.9597 . ?
C12 H12B 0.9597 . ?
C11 C10 1.505(5) . ?
C11 H11A 0.9460 . ?
C11 H11B 0.9460 . ?
C11 H11C 0.9460 . ?
C10 H10A 0.9516 . ?
C10 H10B 0.9516 . ?
C3 C4 1.393(5) . ?
C3 C2 1.488(5) . ?
C4 H4 0.8966 . ?
C9 H9 0.9171 . ?

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
_geom_angle_publ_flag
C9 O1 C12 112.1(3) . . ?
C3 C8 C7 119.7(4) . . ?
C3 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C9 O2 C10 112.8(3) . . ?
C2 C1 C9 127.9(4) . . ?
C2 C1 I1 119.3(3) . . ?
C9 C1 I1 112.8(3) . . ?
C7 C6 C5 119.9(4) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C6 C7 C8 120.5(4) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
O1 C12 C13 108.2(3) . . ?
O1 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
O1 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C10 C11 107.9(3) . . ?
O2 C10 H10A 110.1 . . ?
C11 C10 H10A 110.1 . . ?
O2 C10 H10B 110.1 . . ?
C11 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C8 C3 C4 119.8(4) . . ?
C8 C3 C2 121.2(3) . . ?
C4 C3 C2 118.9(3) . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
O2 C9 O1 108.7(3) . . ?
O2 C9 C1 108.5(3) . . ?
O1 C9 C1 112.9(3) . . ?
O2 C9 H9 108.9 . . ?
O1 C9 H9 108.9 . . ?
C1 C9 H9 108.9 . . ?
C1 C2 C3 128.0(4) . . ?
C1 C2 I2 120.2(3) . . ?
C3 C2 I2 111.7(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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C6 C5 C4 -1.5(6) . . . . ?
C5 C6 C7 C8 1.1(6) . . . . ?
C3 C8 C7 C6 -0.3(6) . . . . ?
C9 O1 C12 C13 -175.1(3) . . . . ?
C9 O2 C10 C11 -173.1(3) . . . . ?
C7 C8 C3 C4 -0.2(6) . . . . ?
C7 C8 C3 C2 176.3(4) . . . . ?
C6 C5 C4 C3 1.0(6) . . . . ?
C8 C3 C4 C5 -0.2(6) . . . . ?
C2 C3 C4 C5 -176.8(4) . . . . ?
C10 O2 C9 O1 -77.3(4) . . . . ?
C10 O2 C9 C1 159.6(3) . . . . ?
C12 O1 C9 O2 166.0(3) . . . . ?
C12 O1 C9 C1 -73.6(4) . . . . ?
C2 C1 C9 O2 -110.7(4) . . . . ?
I1 C1 C9 O2 67.4(3) . . . . ?
C2 C1 C9 O1 128.8(4) . . . . ?
I1 C1 C9 O1 -53.0(4) . . . . ?
C9 C1 C2 C3 -179.2(4) . . . . ?
I1 C1 C2 C3 2.7(6) . . . . ?
C9 C1 C2 I2 0.9(5) . . . . ?
I1 C1 C2 I2 -177.18(16) . . . . ?
C8 C3 C2 C1 73.4(6) . . . . ?
C4 C3 C2 C1 -110.1(5) . . . . ?
C8 C3 C2 I2 -106.7(3) . . . . ?
C4 C3 C2 I2 69.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.285
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.150

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_test1
_database_code_depnum_ccdc_archive 'CCDC 988932'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(Z)-(3,3-diethoxy-1,2-diiodoprop-1-en-1-yl)benzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 I2 O2'
_chemical_formula_sum            'C13 H16 I2 O2'
_chemical_formula_weight         458.06

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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'

_cell_length_a                   11.3978(4)
_cell_length_b                   7.2145(2)
_cell_length_c                   18.1044(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.253(3)
_cell_angle_gamma                90.00
_cell_volume                     1473.30(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8178
_cell_measurement_theta_min      4.5240
_cell_measurement_theta_max      32.2110

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.417
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.053
_exptl_crystal_density_meas      .
_exptl_crystal_density_diffrn    2.065
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    4.258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.52973
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            24970
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.19
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3647
_reflns_number_gt                3215
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0245P)²+1.2359P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3647
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0566
_refine_ls_wR_factor_gt          0.0531
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I2 I 0.598422(17) -0.32474(2) 0.595744(10) 0.01948(6) Uani 1 1 d . . .
I1 I 0.346979(17) -0.20487(3) 0.692806(11) 0.01994(6) Uani 1 1 d . . .
C13 C 0.5329(3) 0.3326(4) 0.88949(17) 0.0250(7) Uani 1 1 d . . .
H13A H 0.547(2) 0.455(3) 0.9131(6) 0.037 Uiso 1 1 calc R . .
H13B H 0.606(2) 0.259(3) 0.8988(3) 0.037 Uiso 1 1 calc R . .
H13C H 0.4692(16) 0.268(3) 0.9107(5) 0.037 Uiso 1 1 calc R . .
C1 C 0.4733(3) -0.0141(4) 0.66727(15) 0.0160(5) Uani 1 1 d . . .
C3 C 0.6584(2) 0.0805(4) 0.61982(15) 0.0152(5) Uani 1 1 d . . .
C2 C 0.5654(2) -0.0542(4) 0.63270(15) 0.0154(5) Uani 1 1 d . . .
C5 C 0.7618(3) 0.2563(4) 0.53542(17) 0.0209(6) Uani 1 1 d . . .
H5 H 0.7711(4) 0.2930(14) 0.4847(19) 0.025 Uiso 1 1 calc R . .
C9 C 0.4523(3) 0.1796(4) 0.69659(15) 0.0165(6) Uani 1 1 d . . .
H9 H 0.5037(18) 0.270(3) 0.6752(8) 0.020 Uiso 1 1 calc R . .
C4 C 0.6738(3) 0.1314(4) 0.54728(16) 0.0180(6) Uani 1 1 d . . .
H4 H 0.6253(18) 0.0817(19) 0.5072(15) 0.022 Uiso 1 1 calc R . .
O1 O 0.48264(18) 0.1739(3) 0.77385(11) 0.0170(4) Uani 1 1 d . . .
C12 C 0.4970(3) 0.3566(4) 0.80627(16) 0.0219(6) Uani 1 1 d . . .
H12A H 0.4236(18) 0.4248(18) 0.7964(3) 0.026 Uiso 1 1 calc R . .
H12B H 0.5573(15) 0.4241(17) 0.7852(5) 0.026 Uiso 1 1 calc R . .
O2 O 0.33337(17) 0.2350(3) 0.67985(10) 0.0173(4) Uani 1 1 d . . .
C6 C 0.8366(3) 0.3291(4) 0.59566(18) 0.0212(6) Uani 1 1 d . . .
H6 H 0.899(2) 0.415(3) 0.5873(4) 0.025 Uiso 1 1 calc R . .
C11 C 0.1701(3) 0.3327(4) 0.59199(18) 0.0238(7) Uani 1 1 d . . .
H11A H 0.1465(8) 0.368(3) 0.5420(11) 0.036 Uiso 1 1 calc R . .
H11B H 0.1576(5) 0.432(3) 0.6236(11) 0.036 Uiso 1 1 calc R . .
H11C H 0.1254(10) 0.230(2) 0.6034(12) 0.036 Uiso 1 1 calc R . .
C8 C 0.7337(3) 0.1559(4) 0.67985(16) 0.0183(6) Uani 1 1 d . . .
H8 H 0.7240(4) 0.1209(13) 0.7316(18) 0.022 Uiso 1 1 calc R . .
C10 C 0.2994(3) 0.2826(4) 0.60306(15) 0.0198(6) Uani 1 1 d . . .
H10A H 0.3130(4) 0.178(3) 0.5713(8) 0.024 Uiso 1 1 calc R . .
H10B H 0.3464(12) 0.387(3) 0.5898(4) 0.024 Uiso 1 1 calc R . .
C7 C 0.8223(3) 0.2796(4) 0.66761(17) 0.0207(6) Uani 1 1 d . . .
H7 H 0.8737(19) 0.331(2) 0.7092(16) 0.025 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I2 C2 2.115(3) . ?
I1 C1 2.091(3) . ?
C13 C12 1.514(4) . ?
C13 H13A 0.9846 . ?
C13 H13B 0.9846 . ?
C13 H13C 0.9846 . ?
C1 C2 1.329(4) . ?
C1 C9 1.526(4) . ?
C3 C8 1.395(4) . ?
C3 C4 1.399(4) . ?
C3 C2 1.481(4) . ?
C5 C6 1.387(4) . ?
C5 C4 1.388(4) . ?
C5 H5 0.9763 . ?
C9 O1 1.392(3) . ?
C9 O2 1.404(3) . ?
C9 H9 0.9919 . ?
C4 H4 0.9198 . ?
O1 C12 1.443(3) . ?
C12 H12A 0.9649 . ?
C12 H12B 0.9649 . ?
O2 C10 1.430(3) . ?
C6 C7 1.383(4) . ?
C6 H6 0.9693 . ?
C11 C10 1.503(4) . ?
C11 H11A 0.9404 . ?
C11 H11B 0.9404 . ?
C11 H11C 0.9404 . ?
C8 C7 1.389(4) . ?
C8 H8 0.9913 . ?
C10 H10A 0.9761 . ?
C10 H10B 0.9761 . ?
C7 H7 0.9600 . ?

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
_geom_angle_publ_flag
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C1 C9 122.5(3) . . ?
C2 C1 I1 125.2(2) . . ?
C9 C1 I1 112.22(19) . . ?
C8 C3 C4 118.9(3) . . ?
C8 C3 C2 120.5(2) . . ?
C4 C3 C2 120.6(2) . . ?
C1 C2 C3 124.3(3) . . ?
C1 C2 I2 122.6(2) . . ?
C3 C2 I2 113.09(19) . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
O1 C9 O2 108.6(2) . . ?
O1 C9 C1 107.1(2) . . ?
O2 C9 C1 112.4(2) . . ?
O1 C9 H9 109.6 . . ?
O2 C9 H9 109.6 . . ?
C1 C9 H9 109.6 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C9 O1 C12 112.3(2) . . ?
O1 C12 C13 107.4(2) . . ?
O1 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
O1 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C9 O2 C10 113.3(2) . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C8 C3 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
O2 C10 C11 108.1(2) . . ?
O2 C10 H10A 110.1 . . ?
C11 C10 H10A 110.1 . . ?
O2 C10 H10B 110.1 . . ?
C11 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C3 1.2(4) . . . . ?
I1 C1 C2 C3 -175.6(2) . . . . ?
C9 C1 C2 I2 177.56(19) . . . . ?
I1 C1 C2 I2 0.8(3) . . . . ?
C8 C3 C2 C1 65.3(4) . . . . ?
C4 C3 C2 C1 -116.1(3) . . . . ?
C8 C3 C2 I2 -111.4(2) . . . . ?
C4 C3 C2 I2 67.2(3) . . . . ?
C2 C1 C9 O1 -105.1(3) . . . . ?
I1 C1 C9 O1 72.0(2) . . . . ?
C2 C1 C9 O2 135.8(3) . . . . ?
I1 C1 C9 O2 -47.1(3) . . . . ?
C6 C5 C4 C3 1.2(4) . . . . ?
C8 C3 C4 C5 -0.7(4) . . . . ?
C2 C3 C4 C5 -179.4(3) . . . . ?
O2 C9 O1 C12 -73.9(3) . . . . ?
C1 C9 O1 C12 164.6(2) . . . . ?
C9 O1 C12 C13 -178.5(3) . . . . ?
O1 C9 O2 C10 167.8(2) . . . . ?
C1 C9 O2 C10 -73.9(3) . . . . ?
C4 C5 C6 C7 -1.1(5) . . . . ?
C4 C3 C8 C7 0.1(4) . . . . ?
C2 C3 C8 C7 178.8(3) . . . . ?
C9 O2 C10 C11 178.1(2) . . . . ?
C5 C6 C7 C8 0.5(4) . . . . ?
C3 C8 C7 C6 0.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.057
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.121

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lsg
_database_code_depnum_ccdc_archive 'CCDC 1037178'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT171_lsg                 
;
PROBLEM: The CIF-Embedded .res File Contains EADP Records          1 Report
RESPONSE: C4 and C5 have been refined using EADP C4 C5. Otherwise C4 is
non positive definite.
;
_vrf_PLAT172_lsg                 
;
PROBLEM: The CIF-Embedded .res File Contains DFIX Records          1 Report 
RESPONSE: Without DFIX the distance C6-H6 is 0.8 Angstroem, hence
DFIX 0.96 0.01 O6 H6 Has been applied.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (E)-(1,2-diiodovinyl)benzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 I2'
_chemical_formula_sum            'C8 H6 I2'
_chemical_formula_weight         355.93

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   10.1365(4)
_cell_length_b                   15.9425(6)
_cell_length_c                   5.7295(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.279(4)
_cell_angle_gamma                90
_cell_volume                     923.31(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5122
_cell_measurement_theta_min      4.1572
_cell_measurement_theta_max      32.3051

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.560
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    6.739
_shelx_estimated_absorpt_T_min   0.319
_shelx_estimated_absorpt_T_max   0.729
_exptl_absorpt_correction_T_min  0.53277
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            9343
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.165
_diffrn_reflns_theta_max         30.092
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1361
_reflns_number_gt                1126
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0231P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1361
_refine_ls_number_parameters     75
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0176
_refine_ls_wR_factor_ref         0.0415
_refine_ls_wR_factor_gt          0.0404
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
I1 I 0.31593(2) 0.11568(2) 1.01681(3) 0.03295(6) Uani 1 1 d . . . . .
H1 H 0.5000 0.036(2) 0.7500 0.034(9) Uiso 1 2 d S . P . .
C1 C 0.4701(4) 0.0924(3) 0.7972(9) 0.0297(9) Uani 0.5 1 d . . P . .
C2 C 0.5323(4) 0.1529(3) 0.6996(7) 0.0249(8) Uani 0.5 1 d . . P . .
C3 C 0.5164(8) 0.2450(2) 0.7224(17) 0.0215(12) Uani 0.5 1 d . . P . .
C41 C 0.4243(8) 0.2864(6) 0.5878(12) 0.0257(13) Uani 0.5 1 d . . P . .
H4 H 0.387(3) 0.259(2) 0.443(5) 0.061(9) Uiso 1 1 d . . . . .
C4 C 0.4426(12) 0.2907(8) 0.5468(19) 0.0346(5) Uani 0.5 1 d . . P . .
C5 C 0.4316(3) 0.37464(15) 0.5715(4) 0.0346(5) Uani 1 1 d . . . . .
H5 H 0.382(3) 0.4076(17) 0.452(5) 0.041(7) Uiso 1 1 d . . . . .
C6 C 0.5000 0.4177(2) 0.7500 0.0357(7) Uani 1 2 d DS T P . .
H6 H 0.5000 0.4775(7) 0.7500 0.056(12) Uiso 1 2 d DS . P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.111(4) . ?
I1 C2 2.131(4) 2_656 ?
C1 C2 1.302(6) . ?
C1 H1 0.99(3) . ?
C2 C3 1.483(5) . ?
C2 C3 1.622(5) 2_656 ?
C2 I1 2.131(4) 2_656 ?
C3 C41 1.340(14) . ?
C3 C41 1.372(13) 2_656 ?
C3 C4 1.411(15) . ?
C3 C4 1.539(15) 2_656 ?
C3 C2 1.622(5) 2_656 ?
C41 C3 1.372(13) 2_656 ?
C41 C5 1.412(9) . ?
C41 H4 0.99(3) . ?
C4 C5 1.352(13) . ?
C4 C3 1.539(15) 2_656 ?
C4 H4 0.94(3) . ?
C5 C6 1.376(3) . ?
C5 H5 0.97(3) . ?
C6 C5 1.376(3) 2_656 ?
C6 H6 0.953(10) . ?

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
_geom_angle_publ_flag
C2 C1 I1 122.0(3) . . ?
C2 C1 H1 112.7(11) . . ?
I1 C1 H1 125.2(10) . . ?
C1 C2 C3 129.5(4) . . ?
C1 C2 I1 116.0(3) . 2_656 ?
C3 C2 I1 114.5(3) . 2_656 ?
C41 C3 C4 119.6(4) 2_656 . ?
C41 C3 C2 120.2(8) 2_656 . ?
C4 C3 C2 120.2(9) . . ?
C3 C41 C5 120.7(7) 2_656 . ?
C3 C41 H4 125.0(19) 2_656 . ?
C5 C41 H4 113.6(18) . . ?
C5 C4 C3 118.7(10) . . ?
C5 C4 H4 123(2) . . ?
C3 C4 H4 116(2) . . ?
C4 C5 C6 122.1(6) . . ?
C6 C5 C41 118.3(4) . . ?
C4 C5 H5 120.2(17) . . ?
C6 C5 H5 117.3(17) . . ?
C41 C5 H5 123.9(17) . . ?
C5 C6 C5 120.1(3) . 2_656 ?
C5 C6 H6 119.94(15) . . ?
C5 C6 H6 119.95(15) 2_656 . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C1 C2 C2 179.6(11) 2_656 . . 2_656 ?
I1 C1 C2 C2 2.7(7) . . . 2_656 ?
C2 C1 C2 C1 -179.6(11) 2_656 . . 2_656 ?
I1 C1 C2 C1 -176.9(10) . . . 2_656 ?
C1 C1 C2 C3 179.3(9) 2_656 . . . ?
C2 C1 C2 C3 -0.2(7) 2_656 . . . ?
I1 C1 C2 C3 2.5(9) . . . . ?
C1 C1 C2 C3 -180.0(9) 2_656 . . 2_656 ?
C2 C1 C2 C3 0.4(6) 2_656 . . 2_656 ?
I1 C1 C2 C3 3.2(7) . . . 2_656 ?
C1 C1 C2 I1 -2.9(8) 2_656 . . 2_656 ?
C2 C1 C2 I1 177.5(8) 2_656 . . 2_656 ?
I1 C1 C2 I1 -179.7(2) . . . 2_656 ?
C2 C2 C3 C3 2(3) 2_656 . . 2_656 ?
C1 C2 C3 C3 5(6) 2_656 . . 2_656 ?
C1 C2 C3 C3 2(3) . . . 2_656 ?
I1 C2 C3 C3 -176(3) 2_656 . . 2_656 ?
C2 C2 C3 C41 -85.7(7) 2_656 . . . ?
C1 C2 C3 C41 -83(4) 2_656 . . . ?
C1 C2 C3 C41 -85.5(8) . . . . ?
C3 C2 C3 C41 -88(3) 2_656 . . . ?
I1 C2 C3 C41 96.7(5) 2_656 . . . ?
C2 C2 C3 C41 80.7(7) 2_656 . . 2_656 ?
C1 C2 C3 C41 83(4) 2_656 . . 2_656 ?
C1 C2 C3 C41 80.9(8) . . . 2_656 ?
C3 C2 C3 C41 79(3) 2_656 . . 2_656 ?
I1 C2 C3 C41 -96.9(5) 2_656 . . 2_656 ?
C2 C2 C3 C4 -100.6(8) 2_656 . . . ?
C1 C2 C3 C4 -98(4) 2_656 . . . ?
C1 C2 C3 C4 -100.4(7) . . . . ?
C3 C2 C3 C4 -103(3) 2_656 . . . ?
I1 C2 C3 C4 81.8(7) 2_656 . . . ?
C2 C2 C3 C4 68.5(8) 2_656 . . 2_656 ?
C1 C2 C3 C4 71(4) 2_656 . . 2_656 ?
C1 C2 C3 C4 68.6(10) . . . 2_656 ?
C3 C2 C3 C4 66(3) 2_656 . . 2_656 ?
I1 C2 C3 C4 -109.2(6) 2_656 . . 2_656 ?
C1 C2 C3 C2 3(4) 2_656 . . 2_656 ?
C1 C2 C3 C2 0.2(6) . . . 2_656 ?
C3 C2 C3 C2 -2(3) 2_656 . . 2_656 ?
I1 C2 C3 C2 -177.6(7) 2_656 . . 2_656 ?
C41 C3 C41 C3 -70.7(14) 2_656 . . 2_656 ?
C4 C3 C41 C3 -173(4) . . . 2_656 ?
C2 C3 C41 C3 96.0(14) . . . 2_656 ?
C4 C3 C41 C3 -60.1(14) 2_656 . . 2_656 ?
C2 C3 C41 C3 59.2(12) 2_656 . . 2_656 ?
C3 C3 C41 C5 99.3(14) 2_656 . . . ?
C41 C3 C41 C5 28.6(5) 2_656 . . . ?
C4 C3 C41 C5 -74(4) . . . . ?
C2 C3 C41 C5 -164.7(4) . . . . ?
C4 C3 C41 C5 39.2(9) 2_656 . . . ?
C2 C3 C41 C5 158.5(4) 2_656 . . . ?
C3 C3 C4 C5 77.3(17) 2_656 . . . ?
C41 C3 C4 C5 84(4) . . . . ?
C41 C3 C4 C5 -0.4(11) 2_656 . . . ?
C2 C3 C4 C5 -179.1(5) . . . . ?
C4 C3 C4 C5 11.5(7) 2_656 . . . ?
C2 C3 C4 C5 141.9(6) 2_656 . . . ?
C41 C3 C4 C3 7(4) . . . 2_656 ?
C41 C3 C4 C3 -77.7(15) 2_656 . . 2_656 ?
C2 C3 C4 C3 103.6(17) . . . 2_656 ?
C4 C3 C4 C3 -65.8(14) 2_656 . . 2_656 ?
C2 C3 C4 C3 64.6(15) 2_656 . . 2_656 ?
C3 C4 C5 C6 6.3(9) . . . . ?
C3 C4 C5 C6 25.3(9) 2_656 . . . ?
C3 C4 C5 C41 -70(4) . . . . ?
C3 C4 C5 C41 -51(3) 2_656 . . . ?
C3 C41 C5 C4 88(4) . . . . ?
C3 C41 C5 C4 111(4) 2_656 . . . ?
C3 C41 C5 C6 -23.0(6) . . . . ?
C3 C41 C5 C6 0.3(7) 2_656 . . . ?
C4 C5 C6 C5 -8.9(5) . . . 2_656 ?
C41 C5 C6 C5 5.4(3) . . . 2_656 ?

_refine_diff_density_max         0.592
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.097

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_test1
_database_code_depnum_ccdc_archive 'CCDC 1037179'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT201_test1               
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          7 Report
RESPONSE: Due to strong disorder of the molecule, anisotropic refinement of
the C atoms leads to many non positive definites. Hence isotropic
refinement was chosen for the C atoms.
;
_vrf_PLAT172_test1               
;
PROBLEM: The CIF-Embedded .res File Contains DFIX Records          1 Report
RESPONSE: Free refinement of the C4-C5 bond leads to a too small distance of 
about 1.23 Angstroem. DFIX 1.38 0.01 C4 C5 was applied.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (E)-1,2-diiodo-1,2-diphenylethene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 I2'
_chemical_formula_sum            'C14 H10 I2'
_chemical_formula_weight         432.02

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   5.7078(3)
_cell_length_b                   17.4128(8)
_cell_length_c                   7.0077(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.984(6)
_cell_angle_gamma                90
_cell_volume                     650.30(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5522
_cell_measurement_theta_min      4.1335
_cell_measurement_theta_max      32.2328

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.206
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    4.806
_shelx_estimated_absorpt_T_min   0.249
_shelx_estimated_absorpt_T_max   0.700
_exptl_absorpt_correction_T_min  0.48258
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            8934
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.143
_diffrn_reflns_theta_max         25.982
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1266
_reflns_number_gt                1099
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0198P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1266
_refine_ls_number_parameters     67
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0162
_refine_ls_wR_factor_ref         0.0374
_refine_ls_wR_factor_gt          0.0368
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
C1 C 0.5485(8) 0.4671(3) 0.9932(7) 0.0241(16) Uiso 0.625(11) 1 d . . P A 1
C2 C 0.4526(11) 0.4070(3) 0.8303(8) 0.0213(13) Uiso 0.625(11) 1 d . . P A 1
C7 C 0.2637(12) 0.3570(3) 0.8342(10) 0.0230(16) Uiso 0.625(11) 1 d . . P A 1
H7 H 0.1953 0.3632 0.9385 0.028 Uiso 0.625(11) 1 calc R U P A 1
C3 C 0.5558(12) 0.3979(4) 0.6843(10) 0.0264(18) Uiso 0.625(11) 1 d . . P A 1
H3 H 0.6923 0.4294 0.6856 0.032 Uiso 0.625(11) 1 calc R U P A 1
C5 C 0.2788(12) 0.2899(3) 0.5455(9) 0.0179(17) Uiso 0.625(11) 1 d D . P A 1
H5 H 0.2288 0.2481 0.4523 0.021 Uiso 0.625(11) 1 calc R U P A 1
C6 C 0.1730(13) 0.2997(4) 0.6950(10) 0.022(2) Uiso 0.625(11) 1 d . . P A 1
H6 H 0.0413 0.2672 0.6996 0.027 Uiso 0.625(11) 1 calc R U P A 1
C4 C 0.4620(14) 0.3429(4) 0.5342(13) 0.023(2) Uiso 0.625(11) 1 d D . P A 1
H4 H 0.5202 0.3406 0.4232 0.028 Uiso 0.625(11) 1 calc R U P A 1
C1A C 0.4099(12) 0.4904(3) 0.9138(11) 0.012(2) Uiso 0.375(11) 1 d . . P A 2
C2A C 0.3793(18) 0.4178(4) 0.7928(13) 0.017(2) Uiso 0.375(11) 1 d . . P A 2
C5A C 0.330(2) 0.2908(6) 0.5413(16) 0.024(3) Uiso 0.375(11) 1 d . . P A 2
H5A H 0.2982 0.2492 0.4479 0.029 Uiso 0.375(11) 1 calc R U P A 2
C7A C 0.209(2) 0.3628(5) 0.7969(16) 0.022(3) Uiso 0.375(11) 1 d . . P A 2
H7A H 0.1077 0.3674 0.8786 0.027 Uiso 0.375(11) 1 calc R U P A 2
C3A C 0.5132(19) 0.4099(6) 0.6587(15) 0.018(3) Uiso 0.375(11) 1 d . . P A 2
H3A H 0.6126 0.4514 0.6427 0.022 Uiso 0.375(11) 1 calc R U P A 2
C4A C 0.502(3) 0.3412(8) 0.548(2) 0.029(4) Uiso 0.375(11) 1 d . . P A 2
H4A H 0.6165 0.3320 0.4806 0.035 Uiso 0.375(11) 1 calc R U P A 2
C6A C 0.196(2) 0.2973(7) 0.6665(19) 0.023(4) Uiso 0.375(11) 1 d . . P A 2
H6A H 0.0866 0.2563 0.6684 0.028 Uiso 0.375(11) 1 calc R U P A 2
I1 I 0.11341(3) 0.56795(2) 0.77373(3) 0.02510(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C1 1.290(10) 3_667 ?
C1 C2 1.500(7) . ?
C1 I1 2.123(5) 3_667 ?
C2 C3 1.360(8) . ?
C2 C7 1.394(7) . ?
C7 C6 1.363(9) . ?
C7 H7 0.9500 . ?
C3 C4 1.382(10) . ?
C3 H3 0.9500 . ?
C5 C6 1.394(9) . ?
C5 C4 1.418(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C4 H4 0.9500 . ?
C1A C1A 1.319(15) 3_667 ?
C1A C2A 1.497(10) . ?
C1A I1 2.112(7) . ?
C2A C7A 1.373(12) . ?
C2A C3A 1.414(12) . ?
C5A C4A 1.304(16) . ?
C5A C6A 1.361(16) . ?
C5A H5A 0.9500 . ?
C7A C6A 1.446(15) . ?
C7A H7A 0.9500 . ?
C3A C4A 1.413(18) . ?
C3A H3A 0.9500 . ?
C4A H4A 0.9500 . ?
C6A H6A 0.9500 . ?
I1 C1 2.123(5) 3_667 ?

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
_geom_angle_publ_flag
C1 C1 C2 128.7(6) 3_667 . ?
C1 C1 I1 119.7(5) 3_667 3_667 ?
C2 C1 I1 111.6(3) . 3_667 ?
C3 C2 C7 119.2(5) . . ?
C3 C2 C1 121.0(5) . . ?
C7 C2 C1 119.6(4) . . ?
C6 C7 C2 122.8(6) . . ?
C6 C7 H7 118.6 . . ?
C2 C7 H7 118.6 . . ?
C2 C3 C4 120.0(6) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C6 C5 C4 119.2(6) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C7 C6 C5 118.2(6) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C3 C4 C5 120.1(7) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C1A C1A C2A 128.8(8) 3_667 . ?
C1A C1A I1 119.7(6) 3_667 . ?
C2A C1A I1 111.4(5) . . ?
C7A C2A C3A 120.2(8) . . ?
C7A C2A C1A 121.1(7) . . ?
C3A C2A C1A 118.5(7) . . ?
C4A C5A C6A 120.7(12) . . ?
C4A C5A H5A 119.7 . . ?
C6A C5A H5A 119.7 . . ?
C2A C7A C6A 114.4(9) . . ?
C2A C7A H7A 122.8 . . ?
C6A C7A H7A 122.8 . . ?
C4A C3A C2A 121.1(9) . . ?
C4A C3A H3A 119.5 . . ?
C2A C3A H3A 119.5 . . ?
C5A C4A C3A 118.5(13) . . ?
C5A C4A H4A 120.8 . . ?
C3A C4A H4A 120.8 . . ?
C5A C6A C7A 124.0(10) . . ?
C5A C6A H6A 118.0 . . ?
C7A C6A H6A 118.0 . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C1 C2 C3 102.9(7) 3_667 . . . ?
I1 C1 C2 C3 -78.1(5) 3_667 . . . ?
C1 C1 C2 C7 -80.5(8) 3_667 . . . ?
I1 C1 C2 C7 98.5(5) 3_667 . . . ?
C3 C2 C7 C6 -1.3(9) . . . . ?
C1 C2 C7 C6 -177.9(6) . . . . ?
C7 C2 C3 C4 4.3(9) . . . . ?
C1 C2 C3 C4 -179.1(6) . . . . ?
C2 C7 C6 C5 1.5(9) . . . . ?
C4 C5 C6 C7 -4.6(9) . . . . ?
C2 C3 C4 C5 -7.5(10) . . . . ?
C6 C5 C4 C3 7.7(10) . . . . ?
C1A C1A C2A C7A 103.9(11) 3_667 . . . ?
I1 C1A C2A C7A -76.3(9) . . . . ?
C1A C1A C2A C3A -81.9(12) 3_667 . . . ?
I1 C1A C2A C3A 97.9(8) . . . . ?
C3A C2A C7A C6A 3.9(13) . . . . ?
C1A C2A C7A C6A 177.9(8) . . . . ?
C7A C2A C3A C4A -8.9(15) . . . . ?
C1A C2A C3A C4A 176.8(10) . . . . ?
C6A C5A C4A C3A -11.8(18) . . . . ?
C2A C3A C4A C5A 12.9(17) . . . . ?
C4A C5A C6A C7A 7.3(17) . . . . ?
C2A C7A C6A C5A -3.0(15) . . . . ?

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.080

_shelxl_version_number           2013-2


_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lsg_k
_database_code_depnum_ccdc_archive 'CCDC 1037180'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;

_vrf_PLAT171_lsg_k               
;
PROBLEM: The CIF-Embedded .res File Contains EADP Records          1 Report 
RESPONSE: C2 and C2A are disordered. Free refinement of the atoms leads
to a much too small temperature factor of C2A. This problem was solved
by applying EADP C2 C2A since both atoms are chemically and structurally 
equivalent.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 dimethyl 2,3-diiodofumarate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 I2 O4'
_chemical_formula_sum            'C6 H6 I2 O4'
_chemical_formula_weight         395.91

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   8.6795(4)
_cell_length_b                   7.5937(2)
_cell_length_c                   8.5520(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.798(5)
_cell_angle_gamma                90
_cell_volume                     533.59(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3759
_cell_measurement_theta_min      4.7733
_cell_measurement_theta_max      32.4633

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.464
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    5.871
_shelx_estimated_absorpt_T_min   0.386
_shelx_estimated_absorpt_T_max   0.591
_exptl_absorpt_correction_T_min  0.72531
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            5167
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.844
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1052
_reflns_number_gt                923
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0263P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1052
_refine_ls_number_parameters     60
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0174
_refine_ls_wR_factor_ref         0.0427
_refine_ls_wR_factor_gt          0.0420
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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 . . . ?

_refine_diff_density_max         0.671
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.102

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1037181'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (E)-2,3-diiodo-3-phenylprop-2-en-1-ol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 I2 O'
_chemical_formula_sum            'C9 H8 I2 O'
_chemical_formula_weight         385.95

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   23.9673(5)
_cell_length_b                   23.9673(5)
_cell_length_c                   7.5322(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4326.7(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4047
_cell_measurement_theta_min      4.3221
_cell_measurement_theta_max      33.5773

_exptl_crystal_description       platelett
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.370
_exptl_crystal_F_000             2816
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    5.769
_shelx_estimated_absorpt_T_min   0.237
_shelx_estimated_absorpt_T_max   0.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.54028
_exptl_absorpt_correction_T_max  1.00000
_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.
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            10866
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.429
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2116
_reflns_number_gt                1501
_reflns_threshold_expression     'I > 2σ(I)'

_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_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_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0197P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2116
_refine_ls_number_parameters     161
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0432
_refine_ls_wR_factor_gt          0.0412
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_restrained_S_all      0.888
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O1 O 0.70503(10) 0.46528(9) 0.1477(3) 0.0399(6) Uani 1 1 d . . . . .
H1 H 0.7310 0.4662 0.0728 0.060 Uiso 1 1 calc R U . . .
C9 C 0.69282(14) 0.40914(15) 0.1909(4) 0.0357(9) Uani 1 1 d . . . . .
H9A H 0.7227 0.3939 0.2677 0.043 Uiso 1 1 calc R U . A 1
H9B H 0.6914 0.3865 0.0810 0.043 Uiso 1 1 calc R U . A 1
C3 C 0.5742(2) 0.3880(2) 0.5460(7) 0.0272(12) Uani 0.802(7) 1 d D . P B 1
I1 I 0.56985(8) 0.41991(7) 0.11266(19) 0.0381(2) Uani 0.802(7) 1 d . . P B 1
I2 I 0.69680(6) 0.38075(10) 0.62937(18) 0.0511(3) Uani 0.802(7) 1 d . . P B 1
C2 C 0.62853(17) 0.39337(16) 0.4541(5) 0.0245(12) Uani 0.802(7) 1 d . . P B 1
C1 C 0.6385(3) 0.4056(2) 0.2844(9) 0.0273(15) Uani 0.802(7) 1 d . . P B 1
C8 C 0.5457(3) 0.4349(2) 0.6043(9) 0.0370(15) Uani 0.802(7) 1 d D . P B 1
H8 H 0.5599 0.4709 0.5774 0.044 Uiso 0.802(7) 1 calc R U P B 1
C4 C 0.5506(3) 0.3369(2) 0.5813(12) 0.0437(18) Uani 0.802(7) 1 d D . P B 1
H4 H 0.5680 0.3041 0.5372 0.052 Uiso 0.802(7) 1 calc R U P B 1
C5 C 0.5018(3) 0.3323(3) 0.6804(9) 0.0446(16) Uani 0.802(7) 1 d D . P B 1
H5 H 0.4873 0.2964 0.7082 0.053 Uiso 0.802(7) 1 calc R U P B 1
C7 C 0.4959(2) 0.4296(3) 0.7035(18) 0.038(2) Uani 0.802(7) 1 d D . P B 1
H7 H 0.4775 0.4622 0.7457 0.046 Uiso 0.802(7) 1 calc R U P B 1
C6 C 0.4744(6) 0.3793(3) 0.738(3) 0.044(3) Uani 0.802(7) 1 d D . P B 1
H6 H 0.4404 0.3761 0.8026 0.053 Uiso 0.802(7) 1 calc R U P B 1
I1A I 0.6943(3) 0.3947(2) 0.5899(11) 0.0436(11) Uani 0.198(7) 1 d . . P B 2
I2A I 0.5520(4) 0.4161(3) 0.1026(9) 0.0489(11) Uani 0.198(7) 1 d . . P B 2
C2A C 0.5973(10) 0.4029(9) 0.342(3) 0.055(7) Uiso 0.198(7) 1 d . . P B 2
C1A C 0.6471(15) 0.4014(14) 0.338(4) 0.037(9) Uiso 0.198(7) 1 d . . P B 2
C3A C 0.5595(8) 0.3931(8) 0.497(3) 0.017(5) Uiso 0.198(7) 1 d D . P B 2
C6A C 0.475(2) 0.3758(10) 0.709(10) 0.039(15) Uiso 0.198(7) 1 d D . P B 2
H6A H 0.4496 0.3701 0.8032 0.046 Uiso 0.198(7) 1 calc R U P B 2
C4A C 0.5445(13) 0.3383(10) 0.523(4) 0.051(12) Uiso 0.198(7) 1 d D . P B 2
H4A H 0.5661 0.3080 0.4795 0.062 Uiso 0.198(7) 1 calc R U P B 2
C5A C 0.4956(11) 0.3303(12) 0.617(3) 0.028(7) Uiso 0.198(7) 1 d D . P B 2
H5A H 0.4770 0.2954 0.6186 0.034 Uiso 0.198(7) 1 calc R U P B 2
C7A C 0.4920(8) 0.4295(10) 0.667(6) 0.032(12) Uiso 0.198(7) 1 d D . P B 2
H7A H 0.4718 0.4601 0.7154 0.039 Uiso 0.198(7) 1 calc R U P B 2
C8A C 0.5331(10) 0.4390(10) 0.568(3) 0.039(10) Uiso 0.198(7) 1 d D . P B 2
H8A H 0.5452 0.4759 0.5428 0.046 Uiso 0.198(7) 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.415(4) . ?
O1 H1 0.8400 . ?
C9 C1 1.483(8) . ?
C9 C1A 1.57(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C3 C4 1.374(5) . ?
C3 C8 1.387(5) . ?
C3 C2 1.480(6) . ?
I1 C1 2.121(7) . ?
I2 C2 2.124(4) . ?
C2 C1 1.332(8) . ?
C8 C7 1.415(9) . ?
C8 H8 0.9500 . ?
C4 C5 1.393(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.376(7) . ?
C5 H5 0.9500 . ?
C7 C6 1.337(10) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
I1A C1A 2.22(3) . ?
I2A C2A 2.13(2) . ?
C2A C1A 1.19(4) . ?
C2A C3A 1.50(3) . ?
C3A C8A 1.377(10) . ?
C3A C4A 1.378(10) . ?
C6A C5A 1.379(10) . ?
C6A C7A 1.38(3) . ?
C6A H6A 0.9500 . ?
C4A C5A 1.382(10) . ?
C4A H4A 0.9500 . ?
C5A H5A 0.9500 . ?
C7A C8A 1.26(3) . ?
C7A H7A 0.9500 . ?
C8A H8A 0.9500 . ?

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
_geom_angle_publ_flag
C9 O1 H1 109.5 . . ?
O1 C9 C1 110.2(3) . . ?
O1 C9 C1A 114.8(13) . . ?
O1 C9 H9A 109.6 . . ?
C1 C9 H9A 109.6 . . ?
O1 C9 H9B 109.6 . . ?
C1 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C4 C3 C8 117.2(5) . . ?
C4 C3 C2 122.1(4) . . ?
C8 C3 C2 120.7(4) . . ?
C1 C2 C3 128.7(5) . . ?
C1 C2 I2 119.3(4) . . ?
C3 C2 I2 112.0(3) . . ?
C2 C1 C9 128.7(6) . . ?
C2 C1 I1 118.8(5) . . ?
C9 C1 I1 112.4(4) . . ?
C3 C8 C7 120.8(5) . . ?
C3 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C3 C4 C5 121.5(6) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 120.3(7) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C6 C7 C8 120.5(7) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C6 C5 119.6(8) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C1A C2A C3A 129(2) . . ?
C1A C2A I2A 119(2) . . ?
C3A C2A I2A 111.9(14) . . ?
C2A C1A C9 136(3) . . ?
C2A C1A I1A 119(3) . . ?
C9 C1A I1A 104.8(16) . . ?
C8A C3A C4A 126(2) . . ?
C8A C3A C2A 117.1(16) . . ?
C4A C3A C2A 114.9(19) . . ?
C5A C6A C7A 121(3) . . ?
C5A C6A H6A 119.3 . . ?
C7A C6A H6A 119.3 . . ?
C3A C4A C5A 115(3) . . ?
C3A C4A H4A 122.4 . . ?
C5A C4A H4A 122.4 . . ?
C6A C5A C4A 117(3) . . ?
C6A C5A H5A 121.7 . . ?
C4A C5A H5A 121.7 . . ?
C8A C7A C6A 122(3) . . ?
C8A C7A H7A 119.1 . . ?
C6A C7A H7A 119.1 . . ?
C7A C8A C3A 117(2) . . ?
C7A C8A H8A 121.7 . . ?
C3A C8A H8A 121.7 . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C3 C2 C1 100.7(8) . . . . ?
C8 C3 C2 C1 -81.0(7) . . . . ?
C4 C3 C2 I2 -80.6(7) . . . . ?
C8 C3 C2 I2 97.7(6) . . . . ?
C3 C2 C1 C9 -177.7(5) . . . . ?
I2 C2 C1 C9 3.6(7) . . . . ?
C3 C2 C1 I1 0.1(7) . . . . ?
I2 C2 C1 I1 -178.6(2) . . . . ?
O1 C9 C1 C2 -110.0(5) . . . . ?
C1A C9 C1 C2 -1(4) . . . . ?
O1 C9 C1 I1 72.1(4) . . . . ?
C1A C9 C1 I1 -179(5) . . . . ?
C4 C3 C8 C7 3.0(13) . . . . ?
C2 C3 C8 C7 -175.4(8) . . . . ?
C8 C3 C4 C5 -3.6(12) . . . . ?
C2 C3 C4 C5 174.7(6) . . . . ?
C3 C4 C5 C6 3.2(16) . . . . ?
C3 C8 C7 C6 -2(2) . . . . ?
C8 C7 C6 C5 1(3) . . . . ?
C4 C5 C6 C7 -2(3) . . . . ?
C3A C2A C1A C9 178(2) . . . . ?
I2A C2A C1A C9 3(5) . . . . ?
C3A C2A C1A I1A -9(4) . . . . ?
I2A C2A C1A I1A 175.0(12) . . . . ?
O1 C9 C1A C2A 80(4) . . . . ?
C1 C9 C1A C2A 1.4(19) . . . . ?
O1 C9 C1A I1A -93.5(13) . . . . ?
C1 C9 C1A I1A -172(6) . . . . ?
C1A C2A C3A C8A 108(3) . . . . ?
I2A C2A C3A C8A -76(2) . . . . ?
C1A C2A C3A C4A -88(4) . . . . ?
I2A C2A C3A C4A 88(2) . . . . ?
C8A C3A C4A C5A 6(4) . . . . ?
C2A C3A C4A C5A -157(2) . . . . ?
C7A C6A C5A C4A 19(9) . . . . ?
C3A C4A C5A C6A -15(5) . . . . ?
C5A C6A C7A C8A -13(11) . . . . ?
C6A C7A C8A C3A 2(8) . . . . ?
C4A C3A C8A C7A 1(5) . . . . ?
C2A C3A C8A C7A 164(3) . . . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1037182'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (E)-ethyl 2,3-diiodo-3-phenylacrylate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 I2 O2'
_chemical_formula_sum            'C11 H10 I2 O2'
_chemical_formula_weight         427.99

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   12.8366(5)
_cell_length_b                   7.0467(2)
_cell_length_c                   14.2790(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.053(4)
_cell_angle_gamma                90
_cell_volume                     1284.42(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6395
_cell_measurement_theta_min      4.2574
_cell_measurement_theta_max      32.3498

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.213
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.876
_shelx_estimated_absorpt_T_min   0.442
_shelx_estimated_absorpt_T_max   0.641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89253
_exptl_absorpt_correction_T_max  1.00000
_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.
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            16765
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.265
_diffrn_reflns_theta_max         30.133
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3760
_reflns_number_gt                2747
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0189P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3760
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_ref         0.0449
_refine_ls_wR_factor_gt          0.0424
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_restrained_S_all      0.917
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
I1 I 0.12723(2) 0.61268(2) 0.43343(2) 0.03292(6) Uani 1 1 d . . . . .
I2 I 0.36112(2) 1.18267(3) 0.47262(2) 0.03897(6) Uani 1 1 d . . . . .
O1 O 0.39490(15) 0.6618(3) 0.53229(13) 0.0356(4) Uani 1 1 d . . . . .
O2 O 0.30772(16) 0.8146(3) 0.63770(13) 0.0440(5) Uani 1 1 d . . . . .
C10 C 0.3740(2) 0.7263(5) 0.71370(19) 0.0414(7) Uani 1 1 d . . . . .
H10A H 0.4458 0.7791 0.7169 0.050 Uiso 1 1 calc R U . . .
H10B H 0.3779 0.5878 0.7031 0.050 Uiso 1 1 calc R U . . .
C4 C 0.0575(2) 1.1278(4) 0.39295(19) 0.0300(6) Uani 1 1 d . . . . .
H4 H 0.0448 1.1206 0.4572 0.036 Uiso 1 1 calc R U . . .
C5 C -0.0121(2) 1.2221(4) 0.3284(2) 0.0388(7) Uani 1 1 d . . . . .
H5 H -0.0730 1.2792 0.3483 0.047 Uiso 1 1 calc R U . . .
C8 C 0.1638(3) 1.0554(6) 0.2699(2) 0.0560(9) Uani 1 1 d . . . . .
H8 H 0.2247 0.9984 0.2497 0.067 Uiso 1 1 calc R U . . .
C11 C 0.3279(3) 0.7653(5) 0.80298(19) 0.0463(8) Uani 1 1 d . . . . .
H11A H 0.3191 0.9025 0.8102 0.069 Uiso 1 1 calc R U . . .
H11B H 0.3746 0.7163 0.8562 0.069 Uiso 1 1 calc R U . . .
H11C H 0.2595 0.7028 0.8014 0.069 Uiso 1 1 calc R U . . .
C7 C 0.0935(3) 1.1496(5) 0.2059(2) 0.0448(8) Uani 1 1 d . . . . .
H7 H 0.1054 1.1561 0.1415 0.054 Uiso 1 1 calc R U . . .
C6 C 0.0067(2) 1.2333(4) 0.2360(2) 0.0452(8) Uani 1 1 d . . . . .
H6 H -0.0409 1.2998 0.1923 0.054 Uiso 1 1 calc R U . . .
C9 C 0.3289(2) 0.7692(4) 0.55135(19) 0.0365(7) Uani 1 1 d . . . . .
C2 C 0.2377(4) 0.9898(8) 0.4362(3) 0.0245(15) Uani 0.568(10) 1 d . . P A 1
C1 C 0.2387(4) 0.8241(8) 0.4777(3) 0.0246(15) Uani 0.568(10) 1 d . . P A 1
C2A C 0.1943(5) 0.8877(9) 0.4288(4) 0.0196(18) Uani 0.432(10) 1 d . . P A 2
C1A C 0.2808(5) 0.9259(9) 0.4842(4) 0.0202(18) Uani 0.432(10) 1 d . . P A 2
C3 C 0.1451(2) 1.0447(5) 0.36314(19) 0.0447(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.115(5) . ?
I1 C2A 2.124(6) . ?
I2 C1A 2.098(7) . ?
I2 C2 2.110(5) . ?
O1 C9 1.189(3) . ?
O2 C9 1.329(3) . ?
O2 C10 1.447(3) . ?
C10 C11 1.487(4) . ?
C4 C3 1.374(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.368(4) . ?
C8 C3 1.380(4) . ?
C8 C7 1.384(4) . ?
C7 C6 1.369(4) . ?
C9 C1 1.529(6) . ?
C9 C1A 1.548(7) . ?
C2 C1 1.309(9) . ?
C2 C3 1.546(6) . ?
C2A C1A 1.321(11) . ?
C2A C3 1.543(7) . ?

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
_geom_angle_publ_flag
C9 O2 C10 115.5(2) . . ?
O2 C10 C11 107.9(2) . . ?
C3 C4 C5 119.3(3) . . ?
C6 C5 C4 120.2(3) . . ?
C3 C8 C7 119.7(3) . . ?
C6 C7 C8 119.7(3) . . ?
C5 C6 C7 120.7(3) . . ?
O1 C9 O2 125.9(2) . . ?
O1 C9 C1 120.7(3) . . ?
O2 C9 C1 111.2(3) . . ?
O1 C9 C1A 124.1(3) . . ?
O2 C9 C1A 107.2(3) . . ?
C1 C2 C3 119.9(5) . . ?
C1 C2 I2 119.5(4) . . ?
C3 C2 I2 120.6(4) . . ?
C2 C1 C9 120.5(5) . . ?
C2 C1 I1 121.2(4) . . ?
C9 C1 I1 117.8(3) . . ?
C1A C2A C3 118.8(6) . . ?
C1A C2A I1 119.0(5) . . ?
C3 C2A I1 122.1(4) . . ?
C2A C1A C9 118.7(6) . . ?
C2A C1A I2 121.2(5) . . ?
C9 C1A I2 119.8(4) . . ?
C4 C3 C8 120.5(3) . . ?
C4 C3 C2A 114.5(3) . . ?
C8 C3 C2A 121.6(3) . . ?
C4 C3 C2 119.6(3) . . ?
C8 C3 C2 117.7(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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O2 C10 C11 -170.2(3) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C3 C8 C7 C6 0.8(5) . . . . ?
C4 C5 C6 C7 0.9(5) . . . . ?
C8 C7 C6 C5 -1.1(5) . . . . ?
C10 O2 C9 O1 1.6(5) . . . . ?
C10 O2 C9 C1 164.6(3) . . . . ?
C10 O2 C9 C1A -159.7(3) . . . . ?
C3 C2 C1 C9 -179.0(3) . . . . ?
I2 C2 C1 C9 -0.6(6) . . . . ?
C3 C2 C1 I1 8.9(6) . . . . ?
I2 C2 C1 I1 -172.8(2) . . . . ?
O1 C9 C1 C2 -103.9(5) . . . . ?
O2 C9 C1 C2 92.1(5) . . . . ?
C1A C9 C1 C2 2.6(5) . . . . ?
O1 C9 C1 I1 68.5(4) . . . . ?
O2 C9 C1 I1 -95.5(3) . . . . ?
C1A C9 C1 I1 175.0(6) . . . . ?
C3 C2A C1A C9 178.9(4) . . . . ?
I1 C2A C1A C9 -0.8(7) . . . . ?
C3 C2A C1A I2 -7.5(7) . . . . ?
I1 C2A C1A I2 172.8(3) . . . . ?
O1 C9 C1A C2A 93.0(6) . . . . ?
O2 C9 C1A C2A -105.3(5) . . . . ?
C1 C9 C1A C2A -2.6(4) . . . . ?
O1 C9 C1A I2 -80.7(5) . . . . ?
O2 C9 C1A I2 80.9(4) . . . . ?
C1 C9 C1A I2 -176.3(7) . . . . ?
C5 C4 C3 C8 0.2(5) . . . . ?
C5 C4 C3 C2A -159.1(4) . . . . ?
C5 C4 C3 C2 162.8(3) . . . . ?
C7 C8 C3 C4 -0.4(6) . . . . ?
C7 C8 C3 C2A 157.4(4) . . . . ?
C7 C8 C3 C2 -163.3(4) . . . . ?
C1A C2A C3 C4 -103.8(5) . . . . ?
I1 C2A C3 C4 75.9(4) . . . . ?
C1A C2A C3 C8 97.2(6) . . . . ?
I1 C2A C3 C8 -83.1(5) . . . . ?
C1A C2A C3 C2 3.4(4) . . . . ?
I1 C2A C3 C2 -177.0(7) . . . . ?
C1 C2 C3 C4 87.2(5) . . . . ?
I2 C2 C3 C4 -91.2(4) . . . . ?
C1 C2 C3 C8 -109.8(5) . . . . ?
I2 C2 C3 C8 71.9(4) . . . . ?
C1 C2 C3 C2A -3.5(5) . . . . ?
I2 C2 C3 C2A 178.1(6) . . . . ?

_refine_diff_density_max         0.878
_refine_diff_density_min         -0.957
_refine_diff_density_rms         0.098

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1037183'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (E)-(1,2-diiodoprop-1-en-1-yl)benzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         "C9 H8 I2', 'C9 H8 I2', 'C9 H8 I2"
_chemical_formula_sum            'C9 H8 I2'
_chemical_formula_weight         369.95

# start Validation Reply Form
_vrf_PLAT230_shelxl              
;
PROBLEM: Hirshfeld Test Diff for    C19    --  C25     ..        6.8 su    
RESPONSE: Atoms are checked and assigned correctly. The main electron density residue is in the near of C25/C26. 
They can be split, but thus temperature factors become worse. 
That is why we did the structure without splitting of these positions.
;
# end Validation Reply Form

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   18.9368(9)
_cell_length_b                   7.6070(3)
_cell_length_c                   22.9348(12)
_cell_angle_alpha                90
_cell_angle_beta                 109.349(6)
_cell_angle_gamma                90
_cell_volume                     3117.2(3)
_cell_formula_units_Z            12
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6151
_cell_measurement_theta_min      4.1575
_cell_measurement_theta_max      33.5762

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.365
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    5.993
_shelx_estimated_absorpt_T_min   0.266
_shelx_estimated_absorpt_T_max   0.586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72536
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            15609
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         4.166
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6098
_reflns_number_gt                4352
_reflns_threshold_expression     'I > 2σ(I)'

_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_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_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0232P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6098
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0552
_refine_ls_wR_factor_gt          0.0525
_refine_ls_goodness_of_fit_ref   0.857
_refine_ls_restrained_S_all      0.857
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000


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
I5 I 0.11586(2) 0.36965(4) 0.46430(2) 0.03620(9) Uani 1 1 d . . . . .
I3 I 0.25004(2) 0.57397(4) 0.24950(2) 0.04221(10) Uani 1 1 d . . . . .
I4 I 0.05868(2) 0.13403(4) 0.13360(2) 0.04051(9) Uani 1 1 d . . . . .
I6 I 0.14921(2) -0.14468(4) 0.33936(2) 0.04049(9) Uani 1 1 d . . . . .
I1 I 0.47077(2) 0.69471(4) 0.39595(2) 0.04926(11) Uani 1 1 d . . . . .
I2 I 0.33707(2) 0.14477(5) 0.41670(2) 0.05728(12) Uani 1 1 d . . . . .
C13 C 0.3520(3) 0.0469(6) 0.1613(3) 0.0450(14) Uani 1 1 d . . . . .
H13 H 0.3949 -0.0084 0.1567 0.054 Uiso 1 1 calc R U . . .
C22 C 0.1719(3) -0.2560(6) 0.5768(2) 0.0380(12) Uani 1 1 d . . . . .
H22 H 0.1800 -0.3246 0.6131 0.046 Uiso 1 1 calc R U . . .
C21 C 0.2304(3) -0.2188(6) 0.5554(2) 0.0377(12) Uani 1 1 d . . . . .
H21 H 0.2794 -0.2590 0.5778 0.045 Uiso 1 1 calc R U . . .
C20 C 0.2184(3) -0.1246(7) 0.5022(2) 0.0402(13) Uani 1 1 d . . . . .
H20 H 0.2589 -0.1036 0.4874 0.048 Uiso 1 1 calc R U . . .
C3 C 0.5747(3) 0.0827(6) 0.3970(3) 0.0385(13) Uani 1 1 d . . . . .
H3 H 0.6126 0.0137 0.4253 0.046 Uiso 1 1 calc R U . . .
C11 C 0.2684(3) 0.0840(7) 0.2173(3) 0.0484(14) Uani 1 1 d . . . . .
H11 H 0.2527 0.0536 0.2513 0.058 Uiso 1 1 calc R U . . .
C2 C 0.5287(3) 0.1860(7) 0.4180(2) 0.0424(13) Uani 1 1 d . . . . .
H2 H 0.5342 0.1870 0.4607 0.051 Uiso 1 1 calc R U . . .
C6 C 0.4651(3) 0.2819(7) 0.3150(2) 0.0399(13) Uani 1 1 d . . . . .
H6 H 0.4265 0.3485 0.2864 0.048 Uiso 1 1 calc R U . . .
C19 C 0.1479(2) -0.0590(6) 0.4694(2) 0.0334(11) Uani 1 1 d . . . . .
C23 C 0.1015(3) -0.1920(7) 0.5447(2) 0.0414(13) Uani 1 1 d . . . . .
H23 H 0.0610 -0.2159 0.5593 0.050 Uiso 1 1 calc R U . . .
C12 C 0.3303(3) 0.0056(6) 0.2108(3) 0.0440(14) Uani 1 1 d . . . . .
H12 H 0.3580 -0.0773 0.2405 0.053 Uiso 1 1 calc R U . . .
C14 C 0.3126(3) 0.1681(7) 0.1178(3) 0.0432(14) Uani 1 1 d . . . . .
H14 H 0.3280 0.1949 0.0834 0.052 Uiso 1 1 calc R U . . .
C4 C 0.5662(3) 0.0790(7) 0.3356(3) 0.0447(14) Uani 1 1 d . . . . .
H4 H 0.5980 0.0070 0.3213 0.054 Uiso 1 1 calc R U . . .
C24 C 0.0891(3) -0.0943(6) 0.4919(2) 0.0341(12) Uani 1 1 d . . . . .
H24 H 0.0404 -0.0504 0.4706 0.041 Uiso 1 1 calc R U . . .
C5 C 0.5113(3) 0.1796(6) 0.2940(2) 0.0391(13) Uani 1 1 d . . . . .
H5 H 0.5057 0.1777 0.2512 0.047 Uiso 1 1 calc R U . . .
C15 C 0.2507(3) 0.2504(6) 0.1246(2) 0.0342(11) Uani 1 1 d . . . . .
H15 H 0.2238 0.3353 0.0953 0.041 Uiso 1 1 calc R U . . .
C10 C 0.2282(3) 0.2081(6) 0.1745(2) 0.0381(12) Uani 1 1 d . . . . .
C1 C 0.4739(3) 0.2894(8) 0.3766(2) 0.0485(15) Uani 1 1 d . . . . .
C7 C 0.4327(5) 0.4352(11) 0.3987(4) 0.037(3) Uani 0.66(2) 1 d . . P A 1
C8 C 0.3781(5) 0.4095(12) 0.4197(4) 0.038(3) Uani 0.66(2) 1 d . . P A 1
C9 C 0.3365(3) 0.5491(8) 0.4429(3) 0.0603(17) Uani 0.66(2) 1 d . . P A 1
H9A H 0.3545 0.6658 0.4364 0.090 Uiso 0.66(2) 1 calc R U P A 1
H9B H 0.3455 0.5313 0.4871 0.090 Uiso 0.66(2) 1 calc R U P A 1
H9C H 0.2828 0.5402 0.4202 0.090 Uiso 0.66(2) 1 calc R U P A 1
C7A C 0.4071(8) 0.329(2) 0.4010(7) 0.025(5) Uiso 0.34(2) 1 d . . P A 2
C8A C 0.3977(10) 0.495(3) 0.4141(8) 0.034(6) Uiso 0.34(2) 1 d . . P A 2
C9A C 0.3365(3) 0.5491(8) 0.4429(3) 0.0603(17) Uani 0.34(2) 1 d . . P A 2
H9A1 H 0.2870 0.5162 0.4146 0.090 Uiso 0.34(2) 1 calc R U P A 2
H9A2 H 0.3384 0.6764 0.4497 0.090 Uiso 0.34(2) 1 calc R U P A 2
H9A3 H 0.3460 0.4883 0.4824 0.090 Uiso 0.34(2) 1 calc R U P A 2
C25 C 0.1354(3) 0.0280(7) 0.4083(3) 0.0465(14) Uani 1 1 d . . . B 1
C26 C 0.1192(3) 0.1842(7) 0.3933(3) 0.0485(15) Uani 1 1 d . . . B 1
C27 C 0.1050(3) 0.2755(7) 0.3309(2) 0.0446(13) Uani 1 1 d . . . B 1
H27A H 0.0945 0.1869 0.2981 0.067 Uiso 1 1 calc R U . B 1
H27B H 0.1494 0.3432 0.3319 0.067 Uiso 1 1 calc R U . B 1
H27C H 0.0620 0.3548 0.3228 0.067 Uiso 1 1 calc R U . B 1
C16 C 0.1551(4) 0.2835(10) 0.1766(3) 0.022(2) Uani 0.75(2) 1 d . . P C 1
C17 C 0.1485(4) 0.4416(12) 0.2003(3) 0.026(2) Uani 0.75(2) 1 d . . P C 1
C18 C 0.0780(3) 0.5316(7) 0.1975(2) 0.0409(13) Uani 0.75(2) 1 d . . P C 1
H18A H 0.0355 0.4533 0.1785 0.061 Uiso 0.75(2) 1 calc R U P C 1
H18B H 0.0724 0.6390 0.1727 0.061 Uiso 0.75(2) 1 calc R U P C 1
H18C H 0.0796 0.5622 0.2394 0.061 Uiso 0.75(2) 1 calc R U P C 1
C17A C 0.1273(18) 0.375(4) 0.1879(13) 0.038(8) Uiso 0.25(2) 1 d . . P C 2
C16A C 0.1882(18) 0.364(4) 0.1960(13) 0.049(9) Uiso 0.25(2) 1 d . . P C 2
C18A C 0.0780(3) 0.5316(7) 0.1975(2) 0.0409(13) Uani 0.25(2) 1 d . . P C 2
H18D H 0.0690 0.5165 0.2369 0.061 Uiso 0.25(2) 1 calc R U P C 2
H18E H 0.0301 0.5329 0.1636 0.061 Uiso 0.25(2) 1 calc R U P C 2
H18F H 0.1042 0.6430 0.1980 0.061 Uiso 0.25(2) 1 calc R U P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I5 C26 2.171(6) . ?
I3 C16A 2.12(3) . ?
I3 C17 2.133(9) . ?
I4 C16 2.099(7) . ?
I4 C17A 2.35(3) . ?
I6 C25 2.137(6) . ?
I1 C7 2.110(9) . ?
I1 C8A 2.18(2) . ?
I2 C7A 2.041(17) . ?
I2 C8 2.152(10) . ?
C13 C12 1.366(7) . ?
C13 C14 1.382(7) . ?
C13 H13 0.9500 . ?
C22 C21 1.381(6) . ?
C22 C23 1.382(6) . ?
C22 H22 0.9500 . ?
C21 C20 1.368(6) . ?
C21 H21 0.9500 . ?
C20 C19 1.390(6) . ?
C20 H20 0.9500 . ?
C3 C4 1.363(7) . ?
C3 C2 1.373(6) . ?
C3 H3 0.9500 . ?
C11 C12 1.367(7) . ?
C11 C10 1.392(7) . ?
C11 H11 0.9500 . ?
C2 C1 1.396(7) . ?
C2 H2 0.9500 . ?
C6 C1 1.367(7) . ?
C6 C5 1.373(6) . ?
C6 H6 0.9500 . ?
C19 C24 1.398(6) . ?
C19 C25 1.496(7) . ?
C23 C24 1.372(6) . ?
C23 H23 0.9500 . ?
C12 H12 0.9500 . ?
C14 C15 1.382(6) . ?
C14 H14 0.9500 . ?
C4 C5 1.386(7) . ?
C4 H4 0.9500 . ?
C24 H24 0.9500 . ?
C5 H5 0.9500 . ?
C15 C10 1.386(6) . ?
C15 H15 0.9500 . ?
C10 C16 1.514(8) . ?
C10 C16A 1.57(3) . ?
C1 C7 1.535(10) . ?
C1 C7A 1.571(15) . ?
C7 C8 1.292(16) . ?
C8 C9 1.519(10) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C7A C8A 1.33(3) . ?
C25 C26 1.246(7) . ?
C26 C27 1.533(7) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C16 C17 1.342(15) . ?
C17 C18 1.483(9) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C17A C16A 1.11(5) . ?

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
_geom_angle_publ_flag
C12 C13 C14 120.9(5) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C21 C22 C23 118.9(4) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C20 C21 C22 120.6(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C20 C19 121.2(4) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C4 C3 C2 120.1(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C12 C11 C10 120.4(5) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C3 C2 C1 120.0(5) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C1 C6 C5 120.9(5) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C20 C19 C24 118.0(4) . . ?
C20 C19 C25 119.4(4) . . ?
C24 C19 C25 122.2(4) . . ?
C24 C23 C22 121.0(4) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C13 C12 C11 119.8(5) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C13 C14 C15 119.8(5) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C3 C4 C5 120.4(5) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C23 C24 C19 120.4(4) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C6 C5 C4 119.4(5) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C14 C15 C10 119.5(5) . . ?
C14 C15 H15 120.3 . . ?
C10 C15 H15 120.3 . . ?
C15 C10 C11 119.6(5) . . ?
C15 C10 C16 118.2(4) . . ?
C11 C10 C16 121.8(5) . . ?
C15 C10 C16A 113.3(10) . . ?
C11 C10 C16A 119.9(10) . . ?
C6 C1 C2 119.2(5) . . ?
C6 C1 C7 118.1(5) . . ?
C2 C1 C7 121.8(5) . . ?
C6 C1 C7A 122.6(6) . . ?
C2 C1 C7A 111.7(7) . . ?
C8 C7 C1 124.8(9) . . ?
C8 C7 I1 118.4(7) . . ?
C1 C7 I1 116.7(6) . . ?
C7 C8 C9 126.6(9) . . ?
C7 C8 I2 117.0(7) . . ?
C9 C8 I2 116.2(6) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8A C7A C1 116.6(15) . . ?
C8A C7A I2 118.0(14) . . ?
C1 C7A I2 125.4(10) . . ?
C7A C8A I1 118.6(14) . . ?
C26 C25 C19 128.8(6) . . ?
C26 C25 I6 117.5(5) . . ?
C19 C25 I6 113.6(4) . . ?
C25 C26 C27 129.8(6) . . ?
C25 C26 I5 118.6(5) . . ?
C27 C26 I5 111.5(4) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C17 C16 C10 124.1(7) . . ?
C17 C16 I4 119.5(6) . . ?
C10 C16 I4 116.2(5) . . ?
C16 C17 C18 126.9(8) . . ?
C16 C17 I3 116.6(6) . . ?
C18 C17 I3 116.5(6) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16A C17A I4 113(3) . . ?
C17A C16A C10 126(4) . . ?
C17A C16A I3 113(3) . . ?
C10 C16A I3 121.3(18) . . ?

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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C23 C22 C21 C20 -2.0(7) . . . . ?
C22 C21 C20 C19 2.1(8) . . . . ?
C4 C3 C2 C1 -1.0(8) . . . . ?
C21 C20 C19 C24 -0.9(7) . . . . ?
C21 C20 C19 C25 -174.0(5) . . . . ?
C21 C22 C23 C24 0.6(8) . . . . ?
C14 C13 C12 C11 0.5(8) . . . . ?
C10 C11 C12 C13 -1.2(8) . . . . ?
C12 C13 C14 C15 0.7(7) . . . . ?
C2 C3 C4 C5 0.2(8) . . . . ?
C22 C23 C24 C19 0.6(8) . . . . ?
C20 C19 C24 C23 -0.4(7) . . . . ?
C25 C19 C24 C23 172.5(5) . . . . ?
C1 C6 C5 C4 1.8(8) . . . . ?
C3 C4 C5 C6 -0.6(8) . . . . ?
C13 C14 C15 C10 -1.0(7) . . . . ?
C14 C15 C10 C11 0.3(7) . . . . ?
C14 C15 C10 C16 -172.7(5) . . . . ?
C14 C15 C10 C16A 150.6(14) . . . . ?
C12 C11 C10 C15 0.8(8) . . . . ?
C12 C11 C10 C16 173.6(5) . . . . ?
C12 C11 C10 C16A -147.5(15) . . . . ?
C5 C6 C1 C2 -2.5(8) . . . . ?
C5 C6 C1 C7 166.7(6) . . . . ?
C5 C6 C1 C7A -152.0(9) . . . . ?
C3 C2 C1 C6 2.1(8) . . . . ?
C3 C2 C1 C7 -166.7(6) . . . . ?
C3 C2 C1 C7A 154.7(8) . . . . ?
C6 C1 C7 C8 112.1(8) . . . . ?
C2 C1 C7 C8 -79.0(9) . . . . ?
C7A C1 C7 C8 4.3(10) . . . . ?
C6 C1 C7 I1 -69.4(6) . . . . ?
C2 C1 C7 I1 99.6(6) . . . . ?
C7A C1 C7 I1 -177.1(12) . . . . ?
C1 C7 C8 C9 179.1(6) . . . . ?
I1 C7 C8 C9 0.6(10) . . . . ?
C1 C7 C8 I2 -4.9(10) . . . . ?
I1 C7 C8 I2 176.5(3) . . . . ?
C6 C1 C7A C8A -94.0(14) . . . . ?
C2 C1 C7A C8A 114.5(12) . . . . ?
C7 C1 C7A C8A -0.2(10) . . . . ?
C6 C1 C7A I2 88.2(10) . . . . ?
C2 C1 C7A I2 -63.3(11) . . . . ?
C7 C1 C7A I2 -178.0(17) . . . . ?
C1 C7A C8A I1 3.2(17) . . . . ?
I2 C7A C8A I1 -178.9(7) . . . . ?
C20 C19 C25 C26 -115.1(6) . . . . ?
C24 C19 C25 C26 72.0(8) . . . . ?
C20 C19 C25 I6 64.1(5) . . . . ?
C24 C19 C25 I6 -108.7(5) . . . . ?
C19 C25 C26 C27 -179.0(5) . . . . ?
I6 C25 C26 C27 1.8(7) . . . . ?
C19 C25 C26 I5 5.4(7) . . . . ?
I6 C25 C26 I5 -173.81(19) . . . . ?
C15 C10 C16 C17 -86.6(7) . . . . ?
C11 C10 C16 C17 100.6(7) . . . . ?
C16A C10 C16 C17 3.4(17) . . . . ?
C15 C10 C16 I4 89.0(5) . . . . ?
C11 C10 C16 I4 -83.8(6) . . . . ?
C16A C10 C16 I4 179.0(18) . . . . ?
C10 C16 C17 C18 172.6(6) . . . . ?
I4 C16 C17 C18 -2.8(9) . . . . ?
C10 C16 C17 I3 -9.5(8) . . . . ?
I4 C16 C17 I3 175.1(3) . . . . ?
I4 C17A C16A C10 0(3) . . . . ?
I4 C17A C16A I3 -176.5(10) . . . . ?
C15 C10 C16A C17A 106(3) . . . . ?
C11 C10 C16A C17A -104(3) . . . . ?
C16 C10 C16A C17A -1(2) . . . . ?
C15 C10 C16A I3 -77.9(15) . . . . ?
C11 C10 C16A I3 72.3(17) . . . . ?
C16 C10 C16A I3 176(3) . . . . ?

_refine_diff_density_max         1.536
_refine_diff_density_min         -0.822
_refine_diff_density_rms         0.135

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_test1
_database_code_depnum_ccdc_archive 'CCDC 1037184'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (E)-methyl 2,3-diiodo-3-phenylacrylate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 I2 O2'
_chemical_formula_sum            'C10 H8 I2 O2'
_chemical_formula_weight         413.96

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.5998(15)
_cell_length_b                   7.1799(2)
_cell_length_c                   18.253(2)
_cell_angle_alpha                90
_cell_angle_beta                 120.835(11)
_cell_angle_gamma                90
_cell_volume                     2318.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5675
_cell_measurement_theta_min      4.1795
_cell_measurement_theta_max      32.4998

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.372
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    5.399
_shelx_estimated_absorpt_T_min   0.221
_shelx_estimated_absorpt_T_max   0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.53478
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            13308
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.189
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2876
_reflns_number_gt                2264
_reflns_threshold_expression     'I > 2σ(I)'

_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_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_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger. C-H distances are refined.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0257P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2876
_refine_ls_number_parameters     133
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0547
_refine_ls_wR_factor_gt          0.0531
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.941
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

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
I2 I 0.40922(2) 0.62307(3) 0.38961(2) 0.01738(7) Uani 1 1 d . . . . .
I1 I 0.33263(2) 0.04911(3) 0.48452(2) 0.01906(7) Uani 1 1 d . . . . .
O1 O 0.32786(15) 0.6148(4) 0.50290(17) 0.0259(6) Uani 1 1 d . . . . .
O2 O 0.39845(15) 0.4124(4) 0.60686(16) 0.0263(6) Uani 1 1 d . . . . .
C9 C 0.3605(2) 0.4692(6) 0.5261(2) 0.0191(8) Uani 1 1 d . . . . .
C5 C 0.3197(2) 0.0654(5) 0.2130(2) 0.0199(8) Uani 1 1 d D . . . .
H5 H 0.2796(11) 0.0479(7) 0.1630(14) 0.024 Uiso 1 1 calc DR U . . .
C2 C 0.3789(2) 0.3545(5) 0.4087(2) 0.0209(8) Uani 1 1 d . . . . .
C3 C 0.3807(2) 0.2141(5) 0.3496(2) 0.0199(8) Uani 1 1 d . . . . .
C1 C 0.3617(2) 0.3221(5) 0.4677(2) 0.0222(8) Uani 1 1 d . . . . .
C7 C 0.4504(2) 0.0043(5) 0.3132(2) 0.0218(8) Uani 1 1 d . . . . .
H7 H 0.493(2) -0.054(3) 0.3269(7) 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4478(2) 0.1218(5) 0.3712(2) 0.0207(8) Uani 1 1 d . . . . .
H8 H 0.4906(18) 0.1395(9) 0.425(2) 0.025 Uiso 1 1 calc R U . . .
C6 C 0.3870(2) -0.0248(5) 0.2341(2) 0.0215(8) Uani 1 1 d D . . . .
H6 H 0.3890(2) -0.098(2) 0.1979(11) 0.026 Uiso 1 1 calc DR U . . .
C4 C 0.3165(2) 0.1825(6) 0.2710(2) 0.0239(9) Uani 1 1 d . . . . .
H4 H 0.267(2) 0.245(3) 0.2560(6) 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3981(2) 0.5412(6) 0.6671(3) 0.0325(10) Uani 1 1 d . . . . .
H10A H 0.4244 0.6557 0.6680 0.049 Uiso 1 1 calc R U . . .
H10B H 0.4238 0.4850 0.7240 0.049 Uiso 1 1 calc R U . . .
H10C H 0.3457 0.5708 0.6501 0.049 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I2 C2 2.109(4) . ?
I1 C1 2.118(4) . ?
O1 C9 1.197(4) . ?
O2 C9 1.331(4) . ?
O2 C10 1.439(5) . ?
C9 C1 1.510(5) . ?
C5 C4 1.381(5) . ?
C5 C6 1.393(5) . ?
C2 C1 1.316(5) . ?
C2 C3 1.490(5) . ?
C3 C4 1.383(5) . ?
C3 C8 1.396(5) . ?
C7 C8 1.376(5) . ?
C7 C6 1.378(5) . ?

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
_geom_angle_publ_flag
C9 O2 C10 114.8(3) . . ?
O1 C9 O2 124.3(3) . . ?
O1 C9 C1 124.9(3) . . ?
O2 C9 C1 110.8(3) . . ?
C4 C5 C6 120.2(3) . . ?
C1 C2 C3 126.1(4) . . ?
C1 C2 I2 121.6(3) . . ?
C3 C2 I2 112.4(3) . . ?
C4 C3 C8 119.8(3) . . ?
C4 C3 C2 119.8(3) . . ?
C8 C3 C2 120.3(3) . . ?
C2 C1 C9 124.3(4) . . ?
C2 C1 I1 119.9(3) . . ?
C9 C1 I1 115.9(3) . . ?
C8 C7 C6 120.7(4) . . ?
C7 C8 C3 119.8(4) . . ?
C7 C6 C5 119.5(3) . . ?
C5 C4 C3 120.0(4) . . ?

_refine_diff_density_max         1.395
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.151

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
_chemical_properties_physical    Light-sensitive
