# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_11
_audit_block_doi                 10.5517/cc13g4yn
_database_code_depnum_ccdc_archive 'CCDC 1026501'
_audit_update_record             
;
2014-09-28 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        Br2-3-EDOT
_chemical_name_common            
Bis-(7-iodo-2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-ylmethyl)-methyl-amine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 Br2 N O4 S2'
_chemical_formula_weight         497.22

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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7337(5)
_cell_length_b                   10.1482(7)
_cell_length_c                   11.8659(8)
_cell_angle_alpha                84.846(2)
_cell_angle_beta                 71.451(2)
_cell_angle_gamma                77.611(2)
_cell_volume                     862.10(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.069
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    4.964
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_T_max  0.712
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7646
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         28.36
_reflns_number_total             4150
_reflns_number_gt                3354
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       APEX2(Bruker,2013)
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2sigma(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)+(0.0628P)²+1.5721P] 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         4150
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_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
Br1 Br -0.02233(7) 0.64378(4) 0.68505(4) 0.04008(14) Uani 1 1 d . . .
Br2 Br 0.42796(6) -0.33128(6) 0.86411(5) 0.05328(17) Uani 1 1 d . . .
S1 S -0.17611(12) 0.38275(9) 0.68583(9) 0.0275(2) Uani 1 1 d . . .
S2 S 0.16117(12) -0.07072(11) 0.80778(9) 0.0295(2) Uani 1 1 d . . .
C1 C 0.0080(5) 0.4647(4) 0.6485(3) 0.0263(7) Uani 1 1 d . . .
C2 C 0.1728(5) 0.3809(4) 0.5995(3) 0.0239(7) Uani 1 1 d . . .
C3 C 0.4937(5) 0.3041(4) 0.5385(4) 0.0323(9) Uani 1 1 d . . .
H3A H 0.5133 0.2662 0.6125 0.039 Uiso 1 1 calc R . .
H3B H 0.6062 0.3340 0.4904 0.039 Uiso 1 1 calc R . .
C4 C 0.4576(5) 0.1971(4) 0.4740(4) 0.0313(8) Uani 1 1 d . . .
H4A H 0.4382 0.2350 0.4000 0.038 Uiso 1 1 calc R . .
H4B H 0.5657 0.1243 0.4549 0.038 Uiso 1 1 calc R . .
C5 C 0.1495(5) 0.2460(3) 0.5916(3) 0.0214(7) Uani 1 1 d . . .
C6 C -0.0308(5) 0.2313(4) 0.6356(3) 0.0220(7) Uani 1 1 d . . .
C7 C -0.1082(5) 0.1072(4) 0.6377(3) 0.0231(7) Uani 1 1 d . . .
H7A H -0.1517 0.1094 0.5692 0.028 Uiso 1 1 calc R . .
H7B H -0.0108 0.0278 0.6328 0.028 Uiso 1 1 calc R . .
C8 C -0.3581(6) -0.0081(4) 0.7411(4) 0.0322(8) Uani 1 1 d . . .
H8A H -0.4583 -0.0115 0.8134 0.048 Uiso 1 1 calc R . .
H8B H -0.2721 -0.0931 0.7307 0.048 Uiso 1 1 calc R . .
H8C H -0.4070 0.0097 0.6751 0.048 Uiso 1 1 calc R . .
C9 C -0.2073(5) 0.0852(4) 0.8559(3) 0.0233(7) Uani 1 1 d . . .
H9A H -0.3196 0.0944 0.9235 0.028 Uiso 1 1 calc R . .
H9B H -0.1487 0.1603 0.8569 0.028 Uiso 1 1 calc R . .
C10 C -0.0778(5) -0.0432(4) 0.8744(3) 0.0225(7) Uani 1 1 d . . .
C11 C -0.1235(5) -0.1480(4) 0.9502(3) 0.0227(7) Uani 1 1 d . A .
C12A C -0.3078(13) -0.2447(10) 1.1219(10) 0.024(3) Uani 0.406(17) 1 d P A 1
H12A H -0.4340 -0.2569 1.1623 0.029 Uiso 0.406(17) 1 calc PR A 1
H12B H -0.2623 -0.2079 1.1772 0.029 Uiso 0.406(17) 1 calc PR A 1
C13A C -0.1830(17) -0.3774(13) 1.0741(13) 0.025(3) Uani 0.406(17) 1 d P A 1
H13A H -0.1984 -0.4470 1.1361 0.030 Uiso 0.406(17) 1 calc PR A 1
H13B H -0.2163 -0.4050 1.0088 0.030 Uiso 0.406(17) 1 calc PR A 1
C12B C -0.3059(10) -0.2951(9) 1.0595(9) 0.038(3) Uani 0.594(17) 1 d P A 2
H12C H -0.4265 -0.2986 1.1170 0.046 Uiso 0.594(17) 1 calc PR A 2
H12D H -0.2900 -0.3509 0.9933 0.046 Uiso 0.594(17) 1 calc PR A 2
C13B C -0.1635(14) -0.3475(12) 1.1134(9) 0.036(2) Uani 0.594(17) 1 d P A 2
H13C H -0.1752 -0.2884 1.1764 0.043 Uiso 0.594(17) 1 calc PR A 2
H13D H -0.1805 -0.4355 1.1490 0.043 Uiso 0.594(17) 1 calc PR A 2
C14 C 0.0316(5) -0.2491(4) 0.9578(3) 0.0260(7) Uani 1 1 d . A .
C15 C 0.1942(5) -0.2210(4) 0.8850(3) 0.0295(8) Uani 1 1 d . . .
N1 N -0.2627(4) 0.0987(3) 0.7470(3) 0.0213(6) Uani 1 1 d . . .
O1 O 0.3409(4) 0.4181(3) 0.5636(3) 0.0312(6) Uani 1 1 d . . .
O2 O 0.2974(3) 0.1440(2) 0.5443(2) 0.0255(5) Uani 1 1 d . . .
O3 O -0.3009(4) -0.1552(3) 1.0166(2) 0.0297(6) Uani 1 1 d . . .
O4 O 0.0162(4) -0.3596(3) 1.0315(3) 0.0349(6) 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
Br1 C1 1.854(4) . ?
Br2 C15 1.865(4) . ?
S1 C1 1.719(4) . ?
S1 C6 1.726(4) . ?
S2 C15 1.721(4) . ?
S2 C10 1.734(3) . ?
C1 C2 1.356(5) . ?
C2 O1 1.359(4) . ?
C2 C5 1.433(5) . ?
C3 O1 1.440(5) . ?
C3 C4 1.503(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O2 1.438(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.361(5) . ?
C5 O2 1.372(4) . ?
C6 C7 1.501(5) . ?
C7 N1 1.468(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.454(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N1 1.472(4) . ?
C9 C10 1.509(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.360(5) . ?
C11 O3 1.362(4) . ?
C11 C14 1.422(5) . ?
C12A O3 1.471(9) . ?
C12A C13A 1.516(17) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C13A O4 1.506(12) . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C12B C13B 1.429(14) . ?
C12B O3 1.469(8) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C13B O4 1.406(10) . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C14 C15 1.352(5) . ?
C14 O4 1.361(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
C1 S1 C6 91.86(17) . . ?
C15 S2 C10 92.18(18) . . ?
C2 C1 S1 112.1(3) . . ?
C2 C1 Br1 125.7(3) . . ?
S1 C1 Br1 122.0(2) . . ?
C1 C2 O1 124.7(3) . . ?
C1 C2 C5 111.8(3) . . ?
O1 C2 C5 123.4(3) . . ?
O1 C3 C4 111.6(3) . . ?
O1 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
O1 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
O2 C4 C3 111.7(3) . . ?
O2 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
O2 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 O2 124.7(3) . . ?
C6 C5 C2 113.2(3) . . ?
O2 C5 C2 122.0(3) . . ?
C5 C6 C7 128.1(3) . . ?
C5 C6 S1 110.9(3) . . ?
C7 C6 S1 120.9(3) . . ?
N1 C7 C6 110.9(3) . . ?
N1 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 117.6(3) . . ?
N1 C9 H9A 107.9 . . ?
C10 C9 H9A 107.9 . . ?
N1 C9 H9B 107.9 . . ?
C10 C9 H9B 107.9 . . ?
H9A C9 H9B 107.2 . . ?
C11 C10 C9 127.0(3) . . ?
C11 C10 S2 109.7(3) . . ?
C9 C10 S2 123.1(3) . . ?
C10 C11 O3 123.7(3) . . ?
C10 C11 C14 114.2(3) . . ?
O3 C11 C14 122.1(3) . . ?
O3 C12A C13A 105.0(10) . . ?
O3 C12A H12A 110.7 . . ?
C13A C12A H12A 110.7 . . ?
O3 C12A H12B 110.7 . . ?
C13A C12A H12B 110.7 . . ?
H12A C12A H12B 108.8 . . ?
O4 C13A C12A 108.9(9) . . ?
O4 C13A H13A 109.9 . . ?
C12A C13A H13A 109.9 . . ?
O4 C13A H13B 109.9 . . ?
C12A C13A H13B 109.9 . . ?
H13A C13A H13B 108.3 . . ?
C13B C12B O3 111.6(9) . . ?
C13B C12B H12C 109.3 . . ?
O3 C12B H12C 109.3 . . ?
C13B C12B H12D 109.3 . . ?
O3 C12B H12D 109.3 . . ?
H12C C12B H12D 108.0 . . ?
O4 C13B C12B 112.5(8) . . ?
O4 C13B H13C 109.1 . . ?
C12B C13B H13C 109.1 . . ?
O4 C13B H13D 109.1 . . ?
C12B C13B H13D 109.1 . . ?
H13C C13B H13D 107.8 . . ?
C15 C14 O4 124.5(3) . . ?
C15 C14 C11 112.1(3) . . ?
O4 C14 C11 123.4(3) . . ?
C14 C15 S2 111.7(3) . . ?
C14 C15 Br2 125.4(3) . . ?
S2 C15 Br2 122.8(2) . . ?
C8 N1 C7 111.2(3) . . ?
C8 N1 C9 111.2(3) . . ?
C7 N1 C9 113.5(3) . . ?
C2 O1 C3 112.5(3) . . ?
C5 O2 C4 111.1(3) . . ?
C11 O3 C12B 108.7(4) . . ?
C11 O3 C12A 112.3(4) . . ?
C12B O3 C12A 36.9(4) . . ?
C14 O4 C13B 111.4(5) . . ?
C14 O4 C13A 109.7(6) . . ?
C13B O4 C13A 25.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.928
_refine_diff_density_min         -1.043
_refine_diff_density_rms         0.108
####################################################################### 
# 
# 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_e:\131209d\work\mo_131209d_0m
_audit_block_doi                 10.5517/cc13g4zp
_database_code_depnum_ccdc_archive 'CCDC 1026502'
_audit_update_record             
;
2014-09-28 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        I2-3-alkyl-EDOT
_chemical_name_common            
Butyl-bis-(7-iodo-2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-ylmethyl)-amine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H21 I2 N O4 S2'
_chemical_formula_weight         633.28

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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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           Tetragonal
_symmetry_space_group_name_H-M   P-42(1)c

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

_cell_length_a                   23.3143(14)
_cell_length_b                   23.3143(14)
_cell_length_c                   8.1165(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4411.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9845
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      28.39

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.907
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2448
_exptl_absorpt_coefficient_mu    3.063
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7100
_exptl_absorpt_correction_T_max  0.7493
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            47909
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.24
_diffrn_reflns_theta_max         30.55
_reflns_number_total             6749
_reflns_number_gt                5949
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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)+(0.0322P)²+1.5746P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         6749
_refine_ls_number_parameters     264
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0644
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1' C 0.2348(7) 0.8136(5) 1.2414(19) 0.052(3) Uani 0.469(15) 1 d PD A 2
H1C H 0.2136 0.8424 1.3028 0.063 Uiso 0.469(15) 1 calc PR A 2
H1D H 0.2715 0.8087 1.2957 0.063 Uiso 0.469(15) 1 calc PR A 2
C2' C 0.2025(4) 0.7578(5) 1.2520(13) 0.063(3) Uani 0.469(15) 1 d PD A 2
H2C H 0.2235 0.7277 1.1960 0.076 Uiso 0.469(15) 1 calc PR A 2
H2D H 0.1973 0.7468 1.3662 0.076 Uiso 0.469(15) 1 calc PR A 2
C1 C 0.2463(5) 0.7988(6) 1.2174(19) 0.059(3) Uani 0.531(15) 1 d PD A 1
H1A H 0.2721 0.8144 1.2996 0.070 Uiso 0.531(15) 1 calc PR A 1
H1B H 0.2604 0.7613 1.1854 0.070 Uiso 0.531(15) 1 calc PR A 1
C2 C 0.1870(4) 0.7931(5) 1.2897(10) 0.062(3) Uani 0.531(15) 1 d PD A 1
H2A H 0.1889 0.7700 1.3890 0.074 Uiso 0.531(15) 1 calc PR A 1
H2B H 0.1727 0.8307 1.3199 0.074 Uiso 0.531(15) 1 calc PR A 1
C3 C 0.19912(13) 0.82725(13) 0.9776(4) 0.0386(6) Uani 1 1 d . A .
C4 C 0.15114(13) 0.79268(12) 1.0242(4) 0.0367(6) Uani 1 1 d . A .
C5 C 0.10988(12) 0.78953(13) 0.9069(4) 0.0365(6) Uani 1 1 d . . .
C6 C 0.19252(13) 0.85013(14) 0.8254(4) 0.0420(7) Uani 1 1 d . . .
C7 C 0.05440(12) 0.75654(13) 0.9058(4) 0.0377(6) Uani 1 1 d . . .
H7A H 0.0615 0.7173 0.8719 0.045 Uiso 1 1 calc R . .
H7B H 0.0382 0.7559 1.0158 0.045 Uiso 1 1 calc R . .
C8 C -0.03003(12) 0.74323(13) 0.7367(4) 0.0407(7) Uani 1 1 d . . .
H8A H -0.0620 0.7645 0.6907 0.049 Uiso 1 1 calc R . .
H8B H -0.0441 0.7220 0.8313 0.049 Uiso 1 1 calc R . .
C9 C -0.00835(12) 0.70175(12) 0.6105(4) 0.0338(6) Uani 1 1 d . . .
C10 C -0.03345(12) 0.65165(12) 0.5634(3) 0.0317(5) Uani 1 1 d . . .
C11 C -0.00394(12) 0.62330(12) 0.4341(3) 0.0325(5) Uani 1 1 d . . .
C12 C 0.04226(12) 0.65272(13) 0.3813(3) 0.0339(6) Uani 1 1 d . . .
C13 C -0.06349(16) 0.54445(14) 0.4756(4) 0.0497(8) Uani 1 1 d . . .
H13A H -0.0451 0.5275 0.5711 0.060 Uiso 1 1 calc R . .
H13B H -0.0820 0.5139 0.4143 0.060 Uiso 1 1 calc R . .
C14 C -0.10794(14) 0.58669(16) 0.5317(4) 0.0476(8) Uani 1 1 d . . .
H14A H -0.1260 0.6041 0.4364 0.057 Uiso 1 1 calc R . .
H14B H -0.1373 0.5668 0.5943 0.057 Uiso 1 1 calc R . .
C15 C -0.01240(13) 0.83512(13) 0.8667(4) 0.0401(6) Uani 1 1 d . . .
H15A H 0.0164 0.8550 0.9314 0.048 Uiso 1 1 calc R . .
H15B H -0.0427 0.8231 0.9410 0.048 Uiso 1 1 calc R . .
C16 C -0.03706(18) 0.87622(16) 0.7421(4) 0.0550(8) Uani 1 1 d . . .
H16A H -0.0067 0.8887 0.6685 0.066 Uiso 1 1 calc R . .
H16B H -0.0656 0.8563 0.6765 0.066 Uiso 1 1 calc R . .
C17 C -0.0642(2) 0.92801(17) 0.8201(6) 0.0676(11) Uani 1 1 d . . .
H17A H -0.0351 0.9486 0.8817 0.081 Uiso 1 1 calc R . .
H17B H -0.0931 0.9152 0.8979 0.081 Uiso 1 1 calc R . .
C18 C -0.0919(3) 0.9689(2) 0.7007(9) 0.105(2) Uani 1 1 d . . .
H18A H -0.0633 0.9837 0.6267 0.158 Uiso 1 1 calc R . .
H18B H -0.1090 1.0001 0.7603 0.158 Uiso 1 1 calc R . .
H18C H -0.1209 0.9491 0.6389 0.158 Uiso 1 1 calc R . .
I1 I 0.246799(11) 0.905264(12) 0.70277(4) 0.06424(8) Uani 1 1 d . . .
I2 I 0.099515(9) 0.623424(9) 0.20555(3) 0.04669(6) Uani 1 1 d . . .
N1 N 0.01389(9) 0.78371(10) 0.7915(3) 0.0339(4) Uani 1 1 d . . .
O1 O 0.24518(10) 0.83569(12) 1.0768(3) 0.0552(6) Uani 1 1 d D . .
O2 O 0.14737(11) 0.76661(11) 1.1739(3) 0.0532(6) Uani 1 1 d D . .
O3 O -0.02055(10) 0.57133(9) 0.3727(3) 0.0430(5) Uani 1 1 d . . .
O4 O -0.08249(9) 0.63077(10) 0.6325(3) 0.0415(5) Uani 1 1 d . . .
S1 S 0.12856(3) 0.82970(4) 0.73624(10) 0.04486(17) Uani 1 1 d . . .
S2 S 0.05135(3) 0.71578(3) 0.48985(10) 0.03761(15) 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' O1 1.452(14) . ?
C1' C2' 1.506(9) . ?
C1' H1C 0.9700 . ?
C1' H1D 0.9700 . ?
C2' O2 1.448(8) . ?
C2' H2C 0.9700 . ?
C2' H2D 0.9700 . ?
C1 O1 1.428(12) . ?
C1 C2 1.508(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 O2 1.455(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C6 1.354(5) . ?
C3 O1 1.356(4) . ?
C3 C4 1.430(4) . ?
C4 C5 1.356(4) . ?
C4 O2 1.361(4) . ?
C5 C7 1.505(4) . ?
C5 S1 1.728(3) . ?
C6 S1 1.725(3) . ?
C6 I1 2.060(3) . ?
C7 N1 1.468(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.462(3) . ?
C8 C9 1.497(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.361(4) . ?
C9 S2 1.733(3) . ?
C10 O4 1.363(3) . ?
C10 C11 1.418(4) . ?
C11 C12 1.347(4) . ?
C11 O3 1.366(4) . ?
C12 S2 1.727(3) . ?
C12 I2 2.070(3) . ?
C13 O3 1.446(4) . ?
C13 C14 1.500(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O4 1.441(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N1 1.478(4) . ?
C15 C16 1.507(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.503(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.504(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
O1 C1' C2' 116.2(11) . . ?
O1 C1' H1C 108.2 . . ?
C2' C1' H1C 108.2 . . ?
O1 C1' H1D 108.2 . . ?
C2' C1' H1D 108.2 . . ?
H1C C1' H1D 107.4 . . ?
O2 C2' C1' 107.3(10) . . ?
O2 C2' H2C 110.3 . . ?
C1' C2' H2C 110.3 . . ?
O2 C2' H2D 110.3 . . ?
C1' C2' H2D 110.3 . . ?
H2C C2' H2D 108.5 . . ?
O1 C1 C2 110.4(8) . . ?
O1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
O1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
O2 C2 C1 111.6(10) . . ?
O2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
O2 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C6 C3 O1 125.0(3) . . ?
C6 C3 C4 112.0(3) . . ?
O1 C3 C4 123.0(3) . . ?
C5 C4 O2 123.8(3) . . ?
C5 C4 C3 113.6(3) . . ?
O2 C4 C3 122.6(3) . . ?
C4 C5 C7 129.9(3) . . ?
C4 C5 S1 110.8(2) . . ?
C7 C5 S1 119.3(2) . . ?
C3 C6 S1 111.9(2) . . ?
C3 C6 I1 128.1(2) . . ?
S1 C6 I1 120.04(18) . . ?
N1 C7 C5 109.6(2) . . ?
N1 C7 H7A 109.7 . . ?
C5 C7 H7A 109.7 . . ?
N1 C7 H7B 109.7 . . ?
C5 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N1 C8 C9 112.9(2) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 127.0(3) . . ?
C10 C9 S2 110.4(2) . . ?
C8 C9 S2 122.4(2) . . ?
C9 C10 O4 123.5(2) . . ?
C9 C10 C11 113.5(3) . . ?
O4 C10 C11 123.0(3) . . ?
C12 C11 O3 124.2(3) . . ?
C12 C11 C10 112.7(3) . . ?
O3 C11 C10 123.1(3) . . ?
C11 C12 S2 111.7(2) . . ?
C11 C12 I2 124.5(2) . . ?
S2 C12 I2 123.61(16) . . ?
O3 C13 C14 111.6(3) . . ?
O3 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
O3 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
O4 C14 C13 110.9(3) . . ?
O4 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N1 C15 C16 113.4(3) . . ?
N1 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
N1 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C15 112.9(3) . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 C18 114.7(4) . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
C18 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
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 . . ?
C8 N1 C7 111.4(2) . . ?
C8 N1 C15 111.0(2) . . ?
C7 N1 C15 110.9(2) . . ?
C3 O1 C1 113.6(7) . . ?
C3 O1 C1' 111.3(7) . . ?
C1 O1 C1' 19.1(7) . . ?
C4 O2 C2' 113.4(5) . . ?
C4 O2 C2 110.3(4) . . ?
C2' O2 C2 38.2(4) . . ?
C11 O3 C13 111.7(2) . . ?
C10 O4 C14 111.5(2) . . ?
C6 S1 C5 91.79(15) . . ?
C12 S2 C9 91.67(14) . . ?

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
O1 C1' C2' O2 -59.4(16) . . . . ?
O1 C1 C2 O2 62.6(15) . . . . ?
C6 C3 C4 C5 0.7(4) . . . . ?
O1 C3 C4 C5 -179.6(3) . . . . ?
C6 C3 C4 O2 -178.0(3) . . . . ?
O1 C3 C4 O2 1.6(5) . . . . ?
O2 C4 C5 C7 -3.4(5) . . . . ?
C3 C4 C5 C7 177.9(3) . . . . ?
O2 C4 C5 S1 178.1(2) . . . . ?
C3 C4 C5 S1 -0.6(3) . . . . ?
O1 C3 C6 S1 179.8(3) . . . . ?
C4 C3 C6 S1 -0.5(4) . . . . ?
O1 C3 C6 I1 -2.2(5) . . . . ?
C4 C3 C6 I1 177.5(2) . . . . ?
C4 C5 C7 N1 156.3(3) . . . . ?
S1 C5 C7 N1 -25.3(3) . . . . ?
N1 C8 C9 C10 163.8(3) . . . . ?
N1 C8 C9 S2 -22.0(4) . . . . ?
C8 C9 C10 O4 -2.7(5) . . . . ?
S2 C9 C10 O4 -177.5(2) . . . . ?
C8 C9 C10 C11 176.7(3) . . . . ?
S2 C9 C10 C11 1.9(3) . . . . ?
C9 C10 C11 C12 -1.6(4) . . . . ?
O4 C10 C11 C12 177.8(3) . . . . ?
C9 C10 C11 O3 177.4(3) . . . . ?
O4 C10 C11 O3 -3.2(4) . . . . ?
O3 C11 C12 S2 -178.5(2) . . . . ?
C10 C11 C12 S2 0.5(3) . . . . ?
O3 C11 C12 I2 -3.2(4) . . . . ?
C10 C11 C12 I2 175.78(19) . . . . ?
O3 C13 C14 O4 -62.8(4) . . . . ?
N1 C15 C16 C17 179.4(3) . . . . ?
C15 C16 C17 C18 -177.3(5) . . . . ?
C9 C8 N1 C7 -76.2(3) . . . . ?
C9 C8 N1 C15 159.8(3) . . . . ?
C5 C7 N1 C8 157.7(3) . . . . ?
C5 C7 N1 C15 -78.2(3) . . . . ?
C16 C15 N1 C8 -76.3(4) . . . . ?
C16 C15 N1 C7 159.4(3) . . . . ?
C6 C3 O1 C1 -169.4(7) . . . . ?
C4 C3 O1 C1 10.9(7) . . . . ?
C6 C3 O1 C1' 170.1(6) . . . . ?
C4 C3 O1 C1' -9.6(7) . . . . ?
C2 C1 O1 C3 -41.1(14) . . . . ?
C2 C1 O1 C1' 46(3) . . . . ?
C2' C1' O1 C3 39.2(14) . . . . ?
C2' C1' O1 C1 -62(3) . . . . ?
C5 C4 O2 C2' 158.4(6) . . . . ?
C3 C4 O2 C2' -22.9(7) . . . . ?
C5 C4 O2 C2 -160.4(5) . . . . ?
C3 C4 O2 C2 18.2(6) . . . . ?
C1' C2' O2 C4 48.0(12) . . . . ?
C1' C2' O2 C2 -45.5(10) . . . . ?
C1 C2 O2 C4 -48.9(10) . . . . ?
C1 C2 O2 C2' 53.5(11) . . . . ?
C12 C11 O3 C13 167.4(3) . . . . ?
C10 C11 O3 C13 -11.5(4) . . . . ?
C14 C13 O3 C11 42.8(4) . . . . ?
C9 C10 O4 C14 164.0(3) . . . . ?
C11 C10 O4 C14 -15.4(4) . . . . ?
C13 C14 O4 C10 46.3(4) . . . . ?
C3 C6 S1 C5 0.1(3) . . . . ?
I1 C6 S1 C5 -178.02(19) . . . . ?
C4 C5 S1 C6 0.3(3) . . . . ?
C7 C5 S1 C6 -178.4(3) . . . . ?
C11 C12 S2 C9 0.5(2) . . . . ?
I2 C12 S2 C9 -174.82(18) . . . . ?
C10 C9 S2 C12 -1.4(2) . . . . ?
C8 C9 S2 C12 -176.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14A O4 0.97 2.52 3.285(4) 135.7 7_554
C13 H13A O3 0.97 2.53 3.277(4) 133.8 7

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.55
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/cc13g50r
_database_code_depnum_ccdc_archive 'CCDC 1026503'
_audit_update_record             
;
2014-09-28 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        I2-3-EDOT
_chemical_name_common            
Bis-(7-iodo-2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-ylmethyl)-methyl-amine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 I2 N O4 S2'
_chemical_formula_weight         591.20

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8257(11)
_cell_length_b                   10.5383(14)
_cell_length_c                   11.8883(16)
_cell_angle_alpha                83.995(2)
_cell_angle_beta                 71.977(2)
_cell_angle_gamma                78.365(2)
_cell_volume                     912.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3793
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.44

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    2.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564
_exptl_absorpt_coefficient_mu    3.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4036
_exptl_absorpt_correction_T_max  0.4708
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5996
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         26.50
_reflns_number_total             3759
_reflns_number_gt                3307
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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)+(0.0341P)²+1.8932P] 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     SHELXL
_refine_ls_extinction_coef       0.0122(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3759
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
C1 C 0.0173(6) 0.4473(4) 0.6496(4) 0.0326(9) Uani 1 1 d . . .
C2 C 0.1783(6) 0.3686(4) 0.6018(4) 0.0306(9) Uani 1 1 d . . .
C3 C 0.1558(5) 0.2392(4) 0.5949(4) 0.0290(8) Uani 1 1 d . . .
C4 C -0.0198(6) 0.2206(4) 0.6361(4) 0.0299(8) Uani 1 1 d . . .
C5 C 0.4578(7) 0.1963(6) 0.4801(6) 0.0559(14) Uani 1 1 d . . .
H5A H 0.4416 0.2285 0.4039 0.067 Uiso 1 1 calc R . .
H5B H 0.5641 0.1275 0.4657 0.067 Uiso 1 1 calc R . .
C6 C 0.4931(7) 0.3005(6) 0.5354(6) 0.0584(15) Uani 1 1 d . . .
H6A H 0.5243 0.2657 0.6068 0.070 Uiso 1 1 calc R . .
H6B H 0.5981 0.3330 0.4820 0.070 Uiso 1 1 calc R . .
C7 C -0.0976(6) 0.1021(4) 0.6382(4) 0.0309(9) Uani 1 1 d . . .
H7A H -0.1396 0.1053 0.5691 0.037 Uiso 1 1 calc R . .
H7B H -0.0026 0.0262 0.6342 0.037 Uiso 1 1 calc R . .
C8 C -0.3438(7) -0.0120(4) 0.7369(5) 0.0417(11) Uani 1 1 d . . .
H8A H -0.3955 0.0084 0.6723 0.063 Uiso 1 1 calc R . .
H8B H -0.4395 -0.0193 0.8095 0.063 Uiso 1 1 calc R . .
H8C H -0.2594 -0.0927 0.7240 0.063 Uiso 1 1 calc R . .
C9 C -0.1975(6) 0.0768(4) 0.8547(4) 0.0305(9) Uani 1 1 d . . .
H9A H -0.3089 0.0857 0.9205 0.037 Uiso 1 1 calc R . .
H9B H -0.1378 0.1487 0.8558 0.037 Uiso 1 1 calc R . .
C10 C -0.0751(6) -0.0464(4) 0.8767(4) 0.0293(8) Uani 1 1 d . . .
C11 C -0.1252(5) -0.1455(4) 0.9550(4) 0.0283(8) Uani 1 1 d . . .
C12 C 0.0238(5) -0.2451(4) 0.9651(4) 0.0281(8) Uani 1 1 d . . .
C13 C 0.1871(6) -0.2188(4) 0.8935(4) 0.0332(9) Uani 1 1 d . . .
C14 C -0.1861(7) -0.3676(5) 1.0824(5) 0.0451(12) Uani 1 1 d . . .
H14A H -0.2019 -0.4296 1.1494 0.054 Uiso 1 1 calc R . .
H14B H -0.2173 -0.4021 1.0203 0.054 Uiso 1 1 calc R . .
C15 C -0.3094(7) -0.2439(5) 1.1182(5) 0.0457(12) Uani 1 1 d . . .
H15A H -0.4337 -0.2594 1.1509 0.055 Uiso 1 1 calc R . .
H15B H -0.2770 -0.2092 1.1796 0.055 Uiso 1 1 calc R . .
I1 I -0.01589(5) 0.63670(3) 0.68896(3) 0.04345(13) Uani 1 1 d . . .
I2 I 0.43768(4) -0.33535(3) 0.87622(3) 0.05187(14) Uani 1 1 d . . .
N1 N -0.2486(5) 0.0901(3) 0.7443(3) 0.0286(7) Uani 1 1 d . . .
O1 O 0.3426(4) 0.4069(3) 0.5657(3) 0.0454(8) Uani 1 1 d . . .
O2 O 0.3020(4) 0.1433(3) 0.5478(3) 0.0394(7) Uani 1 1 d . . .
O3 O 0.0034(4) -0.3506(3) 1.0400(3) 0.0408(8) Uani 1 1 d . . .
O4 O -0.3004(4) -0.1502(3) 1.0203(3) 0.0347(7) Uani 1 1 d . . .
S1 S -0.16292(14) 0.36494(11) 0.68552(10) 0.0347(2) Uani 1 1 d . . .
S2 S 0.15988(14) -0.07517(11) 0.81335(10) 0.0360(3) 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 C2 1.353(6) . ?
C1 S1 1.723(4) . ?
C1 I1 2.045(4) . ?
C2 O1 1.354(5) . ?
C2 C3 1.424(6) . ?
C3 C4 1.357(6) . ?
C3 O2 1.378(5) . ?
C4 C7 1.490(6) . ?
C4 S1 1.734(4) . ?
C5 O2 1.421(6) . ?
C5 C6 1.449(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O1 1.437(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N1 1.451(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.451(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N1 1.472(5) . ?
C9 C10 1.501(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.359(6) . ?
C10 S2 1.734(4) . ?
C11 O4 1.359(5) . ?
C11 C12 1.429(6) . ?
C12 C13 1.362(6) . ?
C12 O3 1.353(5) . ?
C13 S2 1.715(5) . ?
C13 I2 2.056(4) . ?
C14 O3 1.453(6) . ?
C14 C15 1.471(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O4 1.439(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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 S1 111.5(3) . . ?
C2 C1 I1 126.0(3) . . ?
S1 C1 I1 122.3(2) . . ?
O1 C2 C1 124.5(4) . . ?
O1 C2 C3 123.4(4) . . ?
C1 C2 C3 112.1(4) . . ?
C4 C3 O2 123.9(4) . . ?
C4 C3 C2 114.3(4) . . ?
O2 C3 C2 121.8(4) . . ?
C3 C4 C7 129.9(4) . . ?
C3 C4 S1 109.8(3) . . ?
C7 C4 S1 120.2(3) . . ?
O2 C5 C6 114.3(5) . . ?
O2 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
O2 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
O1 C6 C5 114.2(5) . . ?
O1 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
O1 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
N1 C7 C4 112.0(3) . . ?
N1 C7 H7A 109.2 . . ?
C4 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C4 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 117.4(3) . . ?
N1 C9 H9A 108.0 . . ?
C10 C9 H9A 108.0 . . ?
N1 C9 H9B 108.0 . . ?
C10 C9 H9B 108.0 . . ?
H9A C9 H9B 107.2 . . ?
C11 C10 C9 126.5(4) . . ?
C11 C10 S2 109.7(3) . . ?
C9 C10 S2 123.5(3) . . ?
C10 C11 O4 123.8(4) . . ?
C10 C11 C12 114.1(4) . . ?
O4 C11 C12 122.1(4) . . ?
C13 C12 O3 124.6(4) . . ?
C13 C12 C11 112.0(4) . . ?
O3 C12 C11 123.4(4) . . ?
C12 C13 S2 111.4(3) . . ?
C12 C13 I2 125.8(3) . . ?
S2 C13 I2 122.7(2) . . ?
O3 C14 C15 111.2(4) . . ?
O3 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
O3 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
O4 C15 C14 112.0(4) . . ?
O4 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
O4 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C8 N1 C7 111.8(4) . . ?
C8 N1 C9 111.6(3) . . ?
C7 N1 C9 113.8(3) . . ?
C2 O1 C6 112.9(4) . . ?
C3 O2 C5 111.5(4) . . ?
C12 O3 C14 111.3(3) . . ?
C11 O4 C15 111.8(3) . . ?
C1 S1 C4 92.2(2) . . ?
C13 S2 C10 92.7(2) . . ?

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
S1 C1 C2 O1 -179.7(3) . . . . ?
I1 C1 C2 O1 -4.4(6) . . . . ?
S1 C1 C2 C3 -0.4(5) . . . . ?
I1 C1 C2 C3 174.9(3) . . . . ?
O1 C2 C3 C4 179.7(4) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
O1 C2 C3 O2 -1.4(6) . . . . ?
C1 C2 C3 O2 179.3(4) . . . . ?
O2 C3 C4 C7 -2.0(7) . . . . ?
C2 C3 C4 C7 176.8(4) . . . . ?
O2 C3 C4 S1 -179.0(3) . . . . ?
C2 C3 C4 S1 -0.2(5) . . . . ?
O2 C5 C6 O1 -56.1(7) . . . . ?
C3 C4 C7 N1 143.6(4) . . . . ?
S1 C4 C7 N1 -39.6(5) . . . . ?
N1 C9 C10 C11 -105.9(5) . . . . ?
N1 C9 C10 S2 80.5(5) . . . . ?
C9 C10 C11 O4 4.7(7) . . . . ?
S2 C10 C11 O4 179.0(3) . . . . ?
C9 C10 C11 C12 -174.3(4) . . . . ?
S2 C10 C11 C12 0.1(5) . . . . ?
C10 C11 C12 C13 0.4(5) . . . . ?
O4 C11 C12 C13 -178.6(4) . . . . ?
C10 C11 C12 O3 178.6(4) . . . . ?
O4 C11 C12 O3 -0.4(6) . . . . ?
O3 C12 C13 S2 -178.8(3) . . . . ?
C11 C12 C13 S2 -0.7(5) . . . . ?
O3 C12 C13 I2 3.0(6) . . . . ?
C11 C12 C13 I2 -178.9(3) . . . . ?
O3 C14 C15 O4 62.7(6) . . . . ?
C4 C7 N1 C8 170.1(4) . . . . ?
C4 C7 N1 C9 -62.3(4) . . . . ?
C10 C9 N1 C8 59.4(5) . . . . ?
C10 C9 N1 C7 -68.3(5) . . . . ?
C1 C2 O1 C6 171.0(5) . . . . ?
C3 C2 O1 C6 -8.2(6) . . . . ?
C5 C6 O1 C2 35.6(7) . . . . ?
C4 C3 O2 C5 162.1(5) . . . . ?
C2 C3 O2 C5 -16.6(6) . . . . ?
C6 C5 O2 C3 44.2(6) . . . . ?
C13 C12 O3 C14 -166.3(4) . . . . ?
C11 C12 O3 C14 15.7(6) . . . . ?
C15 C14 O3 C12 -45.2(6) . . . . ?
C10 C11 O4 C15 -163.4(4) . . . . ?
C12 C11 O4 C15 15.5(6) . . . . ?
C14 C15 O4 C11 -45.5(6) . . . . ?
C2 C1 S1 C4 0.3(4) . . . . ?
I1 C1 S1 C4 -175.3(3) . . . . ?
C3 C4 S1 C1 0.0(3) . . . . ?
C7 C4 S1 C1 -177.4(3) . . . . ?
C12 C13 S2 C10 0.6(4) . . . . ?
I2 C13 S2 C10 178.9(3) . . . . ?
C11 C10 S2 C13 -0.4(3) . . . . ?
C9 C10 S2 C13 174.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.439
_refine_diff_density_min         -1.381
_refine_diff_density_rms         0.120
####################################################################### 
# 
# 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_11
_audit_block_doi                 10.5517/cc13g51s
_database_code_depnum_ccdc_archive 'CCDC 1026504'
_audit_update_record             
;
2014-09-28 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        I2-4-EDOT
_chemical_name_common            
1,2-Bis-(7-iodo-2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-yl)-bis-dimethylsilanyl-methane
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 I2 O4 S2 Si2'
_chemical_formula_weight         678.47

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   p21/c

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                   17.5004(7)
_cell_length_b                   7.2281(3)
_cell_length_c                   19.8464(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.1820(10)
_cell_angle_gamma                90.00
_cell_volume                     2495.86(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1320
_exptl_absorpt_coefficient_mu    2.804
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.592
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21533
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         28.23
_reflns_number_total             6120
_reflns_number_gt                5236
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       APEX2(Bruker,2013)
_computing_cell_refinement       SAINT(Bruker,2013)
_computing_data_reduction        APEX2(Bruker,2013)
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2sigma(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)+(0.0264P)²+2.2885P] 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         6120
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0608
_refine_ls_wR_factor_gt          0.0577
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
I1 I 0.469042(9) 0.73587(2) 0.398868(8) 0.03188(5) Uani 1 1 d . . .
I2 I 0.324141(11) 1.26294(2) -0.044639(10) 0.04126(6) Uani 1 1 d . . .
Si1 Si 0.13003(3) 0.97480(9) 0.29014(3) 0.02450(13) Uani 1 1 d . . .
Si2 Si 0.12653(3) 0.66524(8) 0.09032(3) 0.02449(12) Uani 1 1 d . . .
S1 S 0.28053(3) 0.78003(7) 0.36319(3) 0.02581(11) Uani 1 1 d . . .
S2 S 0.18979(3) 0.98375(8) 0.00349(3) 0.02693(11) Uani 1 1 d . . .
O1 O 0.42989(8) 1.0944(2) 0.28842(8) 0.0287(3) Uani 1 1 d . . .
O2 O 0.27284(9) 1.1901(2) 0.23856(9) 0.0323(4) Uani 1 1 d . . .
O3 O 0.31625(9) 0.6627(2) 0.12423(9) 0.0317(4) Uani 1 1 d . . .
O4 O 0.40677(8) 0.9384(2) 0.06217(8) 0.0272(3) Uani 1 1 d . . .
C1 C 0.37096(12) 0.8579(3) 0.35151(10) 0.0230(4) Uani 1 1 d . . .
C2 C 0.36741(12) 1.0024(3) 0.30730(10) 0.0223(4) Uani 1 1 d . . .
C3 C 0.40704(14) 1.2714(3) 0.25925(14) 0.0339(5) Uani 1 1 d . . .
H3A H 0.4495 1.3245 0.2381 0.041 Uiso 1 1 calc R . .
H3B H 0.3947 1.3547 0.2948 0.041 Uiso 1 1 calc R . .
C4 C 0.33870(15) 1.2525(4) 0.20751(14) 0.0367(6) Uani 1 1 d . . .
H4A H 0.3274 1.3710 0.1857 0.044 Uiso 1 1 calc R . .
H4B H 0.3501 1.1648 0.1730 0.044 Uiso 1 1 calc R . .
C5 C 0.29063(12) 1.0472(3) 0.28289(10) 0.0225(4) Uani 1 1 d . . .
C6 C 0.23573(12) 0.9429(3) 0.30871(11) 0.0231(4) Uani 1 1 d . . .
C7 C 0.10728(16) 1.2216(4) 0.30712(15) 0.0394(6) Uani 1 1 d . . .
H7A H 0.0529 1.2413 0.2978 0.059 Uiso 1 1 calc R . .
H7B H 0.1340 1.3004 0.2785 0.059 Uiso 1 1 calc R . .
H7C H 0.1232 1.2500 0.3538 0.059 Uiso 1 1 calc R . .
C8 C 0.08131(15) 0.8151(4) 0.34544(13) 0.0411(6) Uani 1 1 d . . .
H8A H 0.0266 0.8296 0.3364 0.062 Uiso 1 1 calc R . .
H8B H 0.0971 0.8437 0.3921 0.062 Uiso 1 1 calc R . .
H8C H 0.0951 0.6898 0.3363 0.062 Uiso 1 1 calc R . .
C9 C 0.10718(12) 0.9173(3) 0.19867(11) 0.0256(4) Uani 1 1 d . . .
H9A H 0.0530 0.9403 0.1855 0.031 Uiso 1 1 calc R . .
H9B H 0.1363 0.9984 0.1721 0.031 Uiso 1 1 calc R . .
C10 C 0.12555(13) 0.7146(3) 0.18231(12) 0.0272(4) Uani 1 1 d . . .
H10A H 0.0877 0.6352 0.2000 0.033 Uiso 1 1 calc R . .
H10B H 0.1754 0.6831 0.2056 0.033 Uiso 1 1 calc R . .
C11 C 0.03476(14) 0.7441(4) 0.04252(13) 0.0348(5) Uani 1 1 d . . .
H11A H -0.0073 0.6755 0.0573 0.052 Uiso 1 1 calc R . .
H11B H 0.0368 0.7239 -0.0051 0.052 Uiso 1 1 calc R . .
H11C H 0.0276 0.8735 0.0507 0.052 Uiso 1 1 calc R . .
C12 C 0.14408(16) 0.4151(3) 0.07669(15) 0.0418(6) Uani 1 1 d . . .
H12A H 0.1031 0.3440 0.0923 0.063 Uiso 1 1 calc R . .
H12B H 0.1920 0.3797 0.1015 0.063 Uiso 1 1 calc R . .
H12C H 0.1462 0.3924 0.0293 0.063 Uiso 1 1 calc R . .
C13 C 0.20653(12) 0.8022(3) 0.05974(11) 0.0237(4) Uani 1 1 d . . .
C14 C 0.28371(12) 0.7919(3) 0.07916(11) 0.0232(4) Uani 1 1 d . . .
C15 C 0.39435(13) 0.7097(3) 0.14890(13) 0.0335(5) Uani 1 1 d . . .
H15A H 0.4194 0.6033 0.1714 0.040 Uiso 1 1 calc R . .
H15B H 0.3943 0.8091 0.1817 0.040 Uiso 1 1 calc R . .
C16 C 0.43810(14) 0.7692(3) 0.09156(14) 0.0338(5) Uani 1 1 d . . .
H16A H 0.4917 0.7875 0.1082 0.041 Uiso 1 1 calc R . .
H16B H 0.4352 0.6732 0.0572 0.041 Uiso 1 1 calc R . .
C17 C 0.32873(12) 0.9262(3) 0.04909(10) 0.0223(4) Uani 1 1 d . . .
C18 C 0.28504(13) 1.0417(3) 0.00714(11) 0.0257(4) 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 2.064(2) . ?
I2 C18 2.057(2) . ?
Si1 C6 1.861(2) . ?
Si1 C8 1.861(3) . ?
Si1 C9 1.863(2) . ?
Si1 C7 1.866(2) . ?
Si2 C12 1.859(3) . ?
Si2 C10 1.862(2) . ?
Si2 C11 1.864(3) . ?
Si2 C13 1.868(2) . ?
S1 C1 1.719(2) . ?
S1 C6 1.728(2) . ?
S2 C18 1.713(2) . ?
S2 C13 1.728(2) . ?
O1 C2 1.366(2) . ?
O1 C3 1.443(3) . ?
O2 C5 1.371(2) . ?
O2 C4 1.437(3) . ?
O3 C14 1.374(3) . ?
O3 C15 1.442(3) . ?
O4 C17 1.365(2) . ?
O4 C16 1.437(3) . ?
C1 C2 1.361(3) . ?
C2 C5 1.416(3) . ?
C3 C4 1.496(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.364(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.542(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.366(3) . ?
C14 C17 1.421(3) . ?
C15 C16 1.501(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.356(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
C6 Si1 C8 108.36(11) . . ?
C6 Si1 C9 105.65(10) . . ?
C8 Si1 C9 111.87(12) . . ?
C6 Si1 C7 108.02(11) . . ?
C8 Si1 C7 111.46(13) . . ?
C9 Si1 C7 111.19(12) . . ?
C12 Si2 C10 110.38(12) . . ?
C12 Si2 C11 111.73(12) . . ?
C10 Si2 C11 110.00(11) . . ?
C12 Si2 C13 109.06(11) . . ?
C10 Si2 C13 107.65(10) . . ?
C11 Si2 C13 107.90(11) . . ?
C1 S1 C6 93.14(10) . . ?
C18 S2 C13 93.55(10) . . ?
C2 O1 C3 110.26(17) . . ?
C5 O2 C4 111.99(17) . . ?
C14 O3 C15 111.84(16) . . ?
C17 O4 C16 110.64(16) . . ?
C2 C1 S1 111.07(16) . . ?
C2 C1 I1 126.82(16) . . ?
S1 C1 I1 122.10(11) . . ?
C1 C2 O1 124.61(19) . . ?
C1 C2 C5 111.84(19) . . ?
O1 C2 C5 123.55(19) . . ?
O1 C3 C4 111.15(19) . . ?
O1 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
O1 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O2 C4 C3 110.7(2) . . ?
O2 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
O2 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 O2 122.50(19) . . ?
C6 C5 C2 115.19(19) . . ?
O2 C5 C2 122.26(19) . . ?
C5 C6 S1 108.74(16) . . ?
C5 C6 Si1 125.62(16) . . ?
S1 C6 Si1 125.62(12) . . ?
Si1 C7 H7A 109.5 . . ?
Si1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Si1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Si1 C8 H8A 109.5 . . ?
Si1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Si1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 Si1 112.90(15) . . ?
C10 C9 H9A 109.0 . . ?
Si1 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
Si1 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 Si2 114.37(15) . . ?
C9 C10 H10A 108.7 . . ?
Si2 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
Si2 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
Si2 C11 H11A 109.5 . . ?
Si2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Si2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si2 C12 H12A 109.5 . . ?
Si2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 S2 108.49(16) . . ?
C14 C13 Si2 129.23(17) . . ?
S2 C13 Si2 122.11(12) . . ?
C13 C14 O3 123.26(19) . . ?
C13 C14 C17 114.87(19) . . ?
O3 C14 C17 121.87(19) . . ?
O3 C15 C16 110.6(2) . . ?
O3 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
O4 C16 C15 110.3(2) . . ?
O4 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
O4 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 O4 124.31(19) . . ?
C18 C17 C14 112.14(19) . . ?
O4 C17 C14 123.55(19) . . ?
C17 C18 S2 110.94(16) . . ?
C17 C18 I2 126.12(16) . . ?
S2 C18 I2 122.92(12) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.23
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.130
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.077
