# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_author_address             
;Faculty of Crystal Chemistry,
Adam Mickiewicz University,
Grunwaldzka 6, 60-780 Poznan
Poland
;
loop_
_publ_author_footnote
; Faculty of Crystal Chemistry,
Adam Mickiewicz University,
Grunwaldzka 6, 60-780 Poznan
Poland
;
_publ_contact_author_address     
;Faculty of Crystal Chemistry,
Adam Mickiewicz University,
Grunwaldzka 6, 60-780 Poznan
Poland
;
_publ_contact_author_email       katran@amu.edu.pl
_publ_contact_author_fax         +48(61)8658008
_publ_contact_author_phone       +48(61)8291443
_publ_contact_author_name        'Andrzej Katrusiak'
_publ_section_title              
;
Halogen...oxygen interactions and disorder modes in pressure
frozen complexes of 1,2-dihaloperfuoroethanes with with 1,4-dioxane
;
loop_
_publ_author_name
A.Katrusiak
A.Olejniczak
A.Vij

data_BrCF2CF2I_C4H8O2
_database_code_depnum_ccdc_archive 'CCDC 656092'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;
1-bromo-2-iodo-1,1,2,2-tetrafluoroethane:1,4-dioxane
;
_chemical_name_common            
1-bromo-2-iodo-1,1,2,2-tetrafluoroethane:1,4-dioxane
_chemical_formula_moiety         'C6 H8 Br F4 I O2'
_chemical_formula_sum            'C6 H8 Br F4 I O2'
_chemical_formula_weight         394.93
_chemical_melting_point          ?
_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                   9.5983(19)
_cell_length_b                   5.9716(12)
_cell_length_c                   9.784(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.41(3)
_cell_angle_gamma                90.00
_cell_volume                     535.13(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3961
_cell_measurement_theta_min      4.05
_cell_measurement_theta_max      29.31
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       620000
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    6.755
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_absorpt_correction_T_min  0.15
_exptl_absorpt_correction_T_max  0.30
_exptl_special_details           
;
high-pressure measurement of 1-bromo-2-iodotetrafluoroethane
with 1,4-dioxane at 0.62(5) GPa
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean 16.4
_diffrn_reflns_number            3961
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_theta_min         4.05
_diffrn_reflns_theta_max         29.31
_diffrn_reflns_theta_full        29.31
_diffrn_measured_fraction_theta_max 0.310
_diffrn_measured_fraction_theta_full 0.310
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_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.
;
_reflns_number_total             455
_reflns_number_gt                400
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0700
_refine_ls_wR_factor_ref         0.1651
_refine_ls_wR_factor_gt          0.1584
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_restrained_S_all      1.196
_refine_ls_number_reflns         455
_refine_ls_number_parameters     64
_refine_ls_number_restraints     0
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0643P)²+4.1936P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;X-Seed (Barbour, 2001)
and POV-Ray (Persistence of Vision, 2004)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
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 0.1960(4) 0.23522(18) 0.5930(2) 0.063(3) Uani 0.50 1 d P . .
Br1 Br 0.1960(4) 0.23522(18) 0.5930(2) 0.063(3) Uani 0.50 1 d P . .
C2 C 0.010(7) 0.432(4) 0.560(4) 0.17(5) Uani 1 1 d . . .
O1 O 0.527(3) 0.4994(13) 0.8635(11) 0.049(15) Uani 1 1 d . . .
C12 C 0.532(4) 0.2969(18) 0.9437(17) 0.09(2) Uani 1 1 d . . .
H12A H 0.6008 0.1934 0.9233 0.102 Uiso 1 1 calc R . .
H12B H 0.4363 0.2265 0.9158 0.102 Uiso 1 1 calc R . .
C11 C 0.577(4) 0.349(2) 1.1006(17) 0.05(2) Uani 1 1 d . . .
H11A H 0.5830 0.2111 1.1544 0.056 Uiso 1 1 calc R . .
H11B H 0.6728 0.4175 1.1281 0.056 Uiso 1 1 calc R . .
F3 F -0.099(5) 0.325(3) 0.577(3) 0.16(3) Uani 1 1 d . . .
F2 F 0.060(5) 0.595(4) 0.672(2) 0.25(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.070(9) 0.0524(8) 0.0631(14) 0.0003(6) 0.017(3) 0.0106(10)
Br1 0.070(9) 0.0524(8) 0.0631(14) 0.0003(6) 0.017(3) 0.0106(10)
C2 0.34(15) 0.077(13) 0.14(3) 0.027(14) 0.15(6) 0.01(3)
O1 0.08(5) 0.043(4) 0.027(7) 0.001(3) 0.027(17) -0.001(7)
C12 0.19(8) 0.032(6) 0.036(10) -0.002(5) 0.04(3) -0.003(12)
C11 0.05(8) 0.037(6) 0.037(10) 0.006(6) 0.00(3) 0.027(11)
F3 0.14(9) 0.137(12) 0.21(3) 0.098(15) 0.07(4) 0.01(2)
F2 0.33(11) 0.27(2) 0.109(16) -0.113(15) 0.00(4) 0.12(3)

_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 C2 2.08(5) . ?
Br1 C2 2.08(5) . ?
C2 F3 1.27(6) . ?
C2 C2 1.40(5) 3_566 ?
C2 F2 1.44(4) . ?
O1 C12 1.435(13) . ?
O1 C11 1.46(3) 3_667 ?
C12 C11 1.50(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 O1 1.46(3) 3_667 ?
C11 H11A 0.9700 . ?
C11 H11B 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
F3 C2 C2 120(7) . 3_566 ?
F3 C2 F2 110(3) . . ?
C2 C2 F2 100(3) 3_566 . ?
F3 C2 Br1 113(2) . . ?
C2 C2 Br1 110(5) 3_566 . ?
F2 C2 Br1 101(4) . . ?
F3 C2 I1 113(2) . . ?
C2 C2 I1 110(5) 3_566 . ?
F2 C2 I1 101(4) . . ?
Br1 C2 I1 0.00(12) . . ?
C12 O1 C11 107.7(14) . 3_667 ?
O1 C12 C11 109.7(11) . . ?
O1 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
O1 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
O1 C11 C12 111(2) 3_667 . ?
O1 C11 H11A 109.3 3_667 . ?
C12 C11 H11A 109.3 . . ?
O1 C11 H11B 109.3 3_667 . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
#END

# Attachment 'C4H8O2.txt'

data_C4H8O2
_database_code_depnum_ccdc_archive 'CCDC 656093'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;
1,4-dioxane
;
_chemical_name_common            1,4-dioxane
_chemical_formula_moiety         'C4 H8 O2'
_chemical_formula_sum            'C4 H8 O2'
_chemical_formula_weight         88.10
_chemical_melting_point          285
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 2(1)/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                   5.6590(10)
_cell_length_b                   6.4100(10)
_cell_length_c                   5.8920(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.36(3)
_cell_angle_gamma                90.00
_cell_volume                     211.46(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    180
_cell_measurement_theta_min      4.83
_cell_measurement_theta_max      29.59
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       420000

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.07
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             96
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
Katrusiak, A. (2003). REDSHADE - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_T_max  0.91
_exptl_special_details           
;
high-pressure measurement of 1,4-dioxane at 0.42(5) GPa
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean 16.4
_diffrn_reflns_number            1696
_diffrn_reflns_av_R_equivalents  0.1265
_diffrn_reflns_av_sigmaI/netI    0.1116
_diffrn_reflns_theta_min         4.83
_diffrn_reflns_theta_max         29.59
_diffrn_reflns_theta_full        29.59
_diffrn_measured_fraction_theta_max 0.304
_diffrn_measured_fraction_theta_full 0.304
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_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.
;
_reflns_number_total             180
_reflns_number_gt                149
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.2073
_refine_ls_R_factor_gt           0.1784
_refine_ls_wR_factor_ref         0.3400
_refine_ls_wR_factor_gt          0.3250
_refine_ls_goodness_of_fit_ref   1.416
_refine_ls_restrained_S_all      1.416
_refine_ls_number_reflns         180
_refine_ls_number_parameters     29
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0757P)²+1.1475P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       1.7(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;X-Seed (Barbour, 2001)
and POV-Ray (Persistence of Vision, 2004)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
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
O1 O 0.7141(19) 0.6145(11) 0.521(3) 0.091(15) Uani 1 1 d . . .
C1 C 0.504(3) 0.7049(18) 0.572(5) 0.06(3) Uani 1 1 d . . .
H1 H 0.4232 0.7746 0.4361 0.072 Uiso 1 1 calc R . .
H2 H 0.5429 0.8089 0.6908 0.072 Uiso 1 1 calc R . .
C2 C 0.663(4) 0.4587(18) 0.348(5) 0.06(2) Uani 1 1 d . . .
H3 H 0.8097 0.3928 0.3193 0.069 Uiso 1 1 calc R . .
H4 H 0.5873 0.5222 0.2065 0.069 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.066(12) 0.030(5) 0.15(3) -0.015(7) -0.072(17) 0.001(5)
C1 0.066(17) 0.025(5) 0.08(6) 0.009(10) -0.02(3) -0.016(7)
C2 0.075(19) 0.042(7) 0.05(5) -0.023(11) -0.01(3) 0.008(8)

_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 C1 1.39(3) . ?
O1 C2 1.43(2) . ?
C1 C2 1.53(4) 3_666 ?
C1 H1 0.9700 . ?
C1 H2 0.9700 . ?
C2 C1 1.53(4) 3_666 ?
C2 H3 0.9700 . ?
C2 H4 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
C1 O1 C2 110.6(12) . . ?
O1 C1 C2 111.4(11) . 3_666 ?
O1 C1 H1 109.3 . . ?
C2 C1 H1 109.3 3_666 . ?
O1 C1 H2 109.3 . . ?
C2 C1 H2 109.3 3_666 . ?
H1 C1 H2 108.0 . . ?
O1 C2 C1 109(3) . 3_666 ?
O1 C2 H3 109.8 . . ?
C1 C2 H3 109.8 3_666 . ?
O1 C2 H4 109.8 . . ?
C1 C2 H4 109.8 3_666 . ?
H3 C2 H4 108.3 . . ?

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
C2 O1 C1 C2 58(3) . . . 3_666 ?
C1 O1 C2 C1 -57.0(16) . . . 3_666 ?

#END

# Attachment 'ICF2CF2I_C4H8O2.txt'

data_ICF2CF2I_C4H8O2
_database_code_depnum_ccdc_archive 'CCDC 656094'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;
1,2-diiodo-1,1,2,2-tetrafluoroethane:1,4-dioxane
;
_chemical_name_common            
1,2-diiodo-1,1,2,2-tetrafluoroethane:1,4-dioxane
_chemical_formula_moiety         'C6 H8 F4 I2 O2'
_chemical_formula_sum            'C6 H8 F4 I2 O2'
_chemical_formula_weight         441.92
_chemical_melting_point          ?
_symmetry_cell_setting           Trigonal
_symmetry_space_group_name_H-M   'R -3'
_symmetry_space_group_name_Hall  '-R 3'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
_cell_length_a                   8.8380(10)
_cell_length_b                   8.8380(10)
_cell_length_c                   13.532(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     915.4(3)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    237
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      29.53
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       300000

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             606
_exptl_absorpt_coefficient_mu    5.180
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
Katrusiak, A. (2003). REDSHADE - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_absorpt_correction_T_min  0.43
_exptl_absorpt_correction_T_max  0.62
_exptl_special_details           
;
high-pressure measurement of 1,2-diiodotetrafluoroethane
with 1,4-dioxane at 0.30(5) GPa
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method       
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean 16.4
_diffrn_reflns_number            1688
_diffrn_reflns_av_R_equivalents  0.1380
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         29.53
_diffrn_reflns_theta_full        29.53
_diffrn_measured_fraction_theta_max 0.407
_diffrn_measured_fraction_theta_full 0.407
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_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.
;
_reflns_number_total             237
_reflns_number_gt                197
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1451
_refine_ls_R_factor_gt           0.1335
_refine_ls_wR_factor_ref         0.3668
_refine_ls_wR_factor_gt          0.3502
_refine_ls_goodness_of_fit_ref   1.440
_refine_ls_restrained_S_all      1.440
_refine_ls_number_reflns         237
_refine_ls_number_parameters     39
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.380
_refine_diff_density_min         -1.017
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.18(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;X-Seed (Barbour, 2001)
and POV-Ray (Persistence of Vision, 2004)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
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
O1 O 1.0000 1.0000 0.076(3) 0.146(19) Uani 1 3 d S . .
C2 C 0.896(3) 1.066(3) 0.023(3) 0.127(19) Uani 0.67 1 d P . .
H1 H 0.8116 1.0794 0.0632 0.153 Uiso 0.33 1 d P . .
H2 H 0.9613 1.1654 -0.0203 0.153 Uiso 0.33 1 d P . .
H3 H 0.8031 0.9818 -0.0196 0.153 Uiso 0.33 1 d P . .
H4 H 0.8560 1.1309 0.0633 0.153 Uiso 0.33 1 d P . .
F2 F 0.928(7) 0.783(4) 0.506(3) 0.101(14) Uani 0.33 1 d P . .
I1 I 1.0000 1.0000 0.6891(6) 0.202(7) Uani 1 3 d S . .
C1 C 0.9399(13) 0.9374(12) 0.5402(17) 0.018(3) Uiso 0.33 1 d P . .
F1 F 0.818(5) 0.778(3) 0.504(2) 0.092(13) Uani 0.33 1 d P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.126(7) 0.126(7) 0.18(6) 0.000 0.000 0.063(4)
C2 0.144(19) 0.115(11) 0.10(6) 0.016(14) -0.046(16) 0.050(10)
F2 0.124(16) 0.15(2) 0.01(5) -0.002(15) -0.002(14) 0.057(15)
I1 0.217(6) 0.217(6) 0.173(19) 0.000 0.000 0.109(3)
F1 0.111(17) 0.110(14) 0.01(4) -0.008(11) -0.009(11) 0.025(12)

_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 C2 1.50(3) 2_765 ?
O1 C2 1.50(3) 3_675 ?
O1 C2 1.50(3) . ?
O1 C2 1.88(7) 12_655 ?
O1 C2 1.88(7) 11_565 ?
O1 C2 1.88(7) 10_775 ?
C2 C2 1.45(6) 12_655 ?
C2 C2 1.45(6) 11_565 ?
C2 O1 1.88(7) 10_775 ?
C2 H1 0.9778 . ?
C2 H2 0.9682 . ?
C2 H3 0.9734 . ?
C2 H4 0.9764 . ?
F2 F1 0.88(2) 12_656 ?
F2 F1 0.96(2) . ?
F2 C1 1.35(4) 12_656 ?
F2 C1 1.39(4) . ?
F2 F2 1.70(3) 11_566 ?
F2 F2 1.70(3) 12_656 ?
F2 C1 1.75(3) 2_765 ?
I1 C1 2.09(2) 3_675 ?
I1 C1 2.09(2) . ?
I1 C1 2.09(2) 2_765 ?
C1 C1 0.940(18) 3_675 ?
C1 C1 0.940(18) 2_765 ?
C1 C1 1.22(4) 11_566 ?
C1 C1 1.22(4) 12_656 ?
C1 F2 1.35(4) 11_566 ?
C1 F1 1.37(2) . ?
C1 C1 1.54(3) 10_776 ?
C1 F1 1.65(3) 11_566 ?
C1 F2 1.75(3) 3_675 ?
C1 F1 1.78(2) 12_656 ?
F1 F2 0.88(2) 11_566 ?
F1 C1 1.65(3) 12_656 ?
F1 C1 1.78(2) 11_566 ?

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 O1 C2 99(3) 2_765 3_675 ?
C2 O1 C2 99(3) 2_765 . ?
C2 O1 C2 99(3) 3_675 . ?
C2 O1 C2 49.4(13) 2_765 12_655 ?
C2 O1 C2 106(3) 3_675 12_655 ?
C2 O1 C2 49.4(13) . 12_655 ?
C2 O1 C2 106(3) 2_765 11_565 ?
C2 O1 C2 49.4(13) 3_675 11_565 ?
C2 O1 C2 49.4(13) . 11_565 ?
C2 O1 C2 74.6(19) 12_655 11_565 ?
C2 O1 C2 49.4(13) 2_765 10_775 ?
C2 O1 C2 49.4(13) 3_675 10_775 ?
C2 O1 C2 106(3) . 10_775 ?
C2 O1 C2 74.6(19) 12_655 10_775 ?
C2 O1 C2 74.6(19) 11_565 10_775 ?
C2 C2 C2 103(3) 12_655 11_565 ?
C2 C2 O1 79.0(13) 12_655 . ?
C2 C2 O1 79.0(13) 11_565 . ?
C2 C2 O1 51.6(18) 12_655 10_775 ?
C2 C2 O1 51.6(18) 11_565 10_775 ?
O1 C2 O1 74(3) . 10_775 ?
C2 C2 H1 115.2 12_655 . ?
C2 C2 H1 140.6 11_565 . ?
O1 C2 H1 115.4 . . ?
O1 C2 H1 163.5 10_775 . ?
C2 C2 H2 115.6 12_655 . ?
C2 C2 H2 37.8 11_565 . ?
O1 C2 H2 116.1 . . ?
O1 C2 H2 71.9 10_775 . ?
H1 C2 H2 111.9 . . ?
C2 C2 H3 37.5 12_655 . ?
C2 C2 H3 116.4 11_565 . ?
O1 C2 H3 115.6 . . ?
O1 C2 H3 72.3 10_775 . ?
H1 C2 H3 91.2 . . ?
H2 C2 H3 103.4 . . ?
C2 C2 H4 140.3 12_655 . ?
C2 C2 H4 115.5 11_565 . ?
O1 C2 H4 115.4 . . ?
O1 C2 H4 163.7 10_775 . ?
H1 C2 H4 25.2 . . ?
H2 C2 H4 91.9 . . ?
H3 C2 H4 111.5 . . ?
F1 F2 F1 161(4) 12_656 . ?
F1 F2 C1 72(2) 12_656 12_656 ?
F1 F2 C1 90(3) . 12_656 ?
F1 F2 C1 101(3) 12_656 . ?
F1 F2 C1 68(2) . . ?
C1 F2 C1 53(2) 12_656 . ?
F1 F2 F2 141(3) 12_656 11_566 ?
F1 F2 F2 22(2) . 11_566 ?
C1 F2 F2 69.0(12) 12_656 11_566 ?
C1 F2 F2 50.8(10) . 11_566 ?
F1 F2 F2 24(2) 12_656 12_656 ?
F1 F2 F2 141(2) . 12_656 ?
C1 F2 F2 52.7(14) 12_656 12_656 ?
C1 F2 F2 78.0(10) . 12_656 ?
F2 F2 F2 119.0(10) 11_566 12_656 ?
F1 F2 C1 69(2) 12_656 2_765 ?
F1 F2 C1 100(3) . 2_765 ?
C1 F2 C1 44(2) 12_656 2_765 ?
C1 F2 C1 32.3(11) . 2_765 ?
F2 F2 C1 80.5(8) 11_566 2_765 ?
F2 F2 C1 46.2(9) 12_656 2_765 ?
C1 I1 C1 26.0(5) 3_675 . ?
C1 I1 C1 26.0(5) 3_675 2_765 ?
C1 I1 C1 26.0(5) . 2_765 ?
C1 C1 C1 60.000(18) 3_675 2_765 ?
C1 C1 C1 67.3(10) 3_675 11_566 ?
C1 C1 C1 90.000(9) 2_765 11_566 ?
C1 C1 C1 90.000(11) 3_675 12_656 ?
C1 C1 C1 67.3(10) 2_765 12_656 ?
C1 C1 C1 45.4(19) 11_566 12_656 ?
C1 C1 F2 116(2) 3_675 11_566 ?
C1 C1 F2 152.2(19) 2_765 11_566 ?
C1 C1 F2 65(2) 11_566 11_566 ?
C1 C1 F2 86(2) 12_656 11_566 ?
C1 C1 F1 151.8(16) 3_675 . ?
C1 C1 F1 135(2) 2_765 . ?
C1 C1 F1 87.2(19) 11_566 . ?
C1 C1 F1 79.4(19) 12_656 . ?
F2 C1 F1 37.8(11) 11_566 . ?
C1 C1 F2 150(2) 3_675 . ?
C1 C1 F2 96(2) 2_765 . ?
C1 C1 F2 97(3) 11_566 . ?
C1 C1 F2 62(2) 12_656 . ?
F2 C1 F2 76.4(9) 11_566 . ?
F1 C1 F2 40.6(10) . . ?
C1 C1 C1 52.3(11) 3_675 10_776 ?
C1 C1 C1 52.3(11) 2_765 10_776 ?
C1 C1 C1 37.7(11) 11_566 10_776 ?
C1 C1 C1 37.7(11) 12_656 10_776 ?
F2 C1 C1 102(3) 11_566 10_776 ?
F1 C1 C1 113(2) . 10_776 ?
F2 C1 C1 99(3) . 10_776 ?
C1 C1 F1 82.0(17) 3_675 11_566 ?
C1 C1 F1 136.8(15) 2_765 11_566 ?
C1 C1 F1 54.3(10) 11_566 11_566 ?
C1 C1 F1 95(2) 12_656 11_566 ?
F2 C1 F1 35.4(10) 11_566 11_566 ?
F1 C1 F1 73.2(7) . 11_566 ?
F2 C1 F1 110.9(16) . 11_566 ?
C1 C1 F1 89.1(16) 10_776 11_566 ?
C1 C1 F2 52.2(17) 3_675 3_675 ?
C1 C1 F2 109.8(17) 2_765 3_675 ?
C1 C1 F2 50.5(14) 11_566 3_675 ?
C1 C1 F2 96(2) 12_656 3_675 ?
F2 C1 F2 64.8(7) 11_566 3_675 ?
F1 C1 F2 102.6(14) . 3_675 ?
F2 C1 F2 137(3) . 3_675 ?
C1 C1 F2 72.8(14) 10_776 3_675 ?
F1 C1 F2 29.9(9) 11_566 3_675 ?
C1 C1 F1 122.8(17) 3_675 12_656 ?
C1 C1 F1 66.6(16) 2_765 12_656 ?
C1 C1 F1 94.6(19) 11_566 12_656 ?
C1 C1 F1 49.9(10) 12_656 12_656 ?
F2 C1 F1 101.5(16) 11_566 12_656 ?
F1 C1 F1 68.9(7) . 12_656 ?
F2 C1 F1 29.0(10) . 12_656 ?
C1 C1 F1 79.7(16) 10_776 12_656 ?
F1 C1 F1 132(2) 11_566 12_656 ?
F2 C1 F1 145(2) 3_675 12_656 ?
C1 C1 I1 77.0(3) 3_675 . ?
C1 C1 I1 77.0(3) 2_765 . ?
C1 C1 I1 143.7(11) 11_566 . ?
C1 C1 I1 143.7(11) 12_656 . ?
F2 C1 I1 130(2) 11_566 . ?
F1 C1 I1 125.8(15) . . ?
F2 C1 I1 117.5(19) . . ?
C1 C1 I1 120.0(15) 10_776 . ?
F1 C1 I1 116.0(14) 11_566 . ?
F2 C1 I1 102.2(17) 3_675 . ?
F1 C1 I1 110.2(12) 12_656 . ?
F2 F1 F2 135(5) 11_566 . ?
F2 F1 C1 70(2) 11_566 . ?
F2 F1 C1 71(3) . . ?
F2 F1 C1 81(3) 11_566 12_656 ?
F2 F1 C1 55(2) . 12_656 ?
C1 F1 C1 46.3(17) . 12_656 ?
F2 F1 C1 50(3) 11_566 11_566 ?
F2 F1 C1 86(2) . 11_566 ?
C1 F1 C1 42.9(16) . 11_566 ?
C1 F1 C1 31.4(8) 12_656 11_566 ?

#END


