# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Cocrystal_2
#TrackingRef '- Cocrystal 1 and 2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H10 F8 I4'
_chemical_formula_weight         1005.96

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   10.277(3)
_cell_length_b                   15.593(5)
_cell_length_c                   9.715(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.844(6)
_cell_angle_gamma                90.00
_cell_volume                     1412.7(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2690
_cell_measurement_theta_min      2.422
_cell_measurement_theta_max      27.398

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             924
_exptl_absorpt_coefficient_mu    4.482
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3276
_exptl_absorpt_correction_T_max  0.6628
_exptl_absorpt_process_details   'SADABS (Sheldrick, G. M., 1996)'

_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  'Smart CCD'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        3.30
_diffrn_reflns_number            5729
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2491
_reflns_number_gt                2128
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Smart
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1999)'
_computing_publication_material  'SHELXTL/PC (Sheldrick, 1999)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0425P)^2^+2.8490P] where P=(Fo^2^+2Fc^2^)/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         2491
_refine_ls_number_parameters     200
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.1029
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.101
_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 0.4888(7) 1.0741(4) 0.1714(7) 0.0897(14) Uani 0.54(4) 1 d P A 1
I1' I 0.4796(8) 1.0813(4) 0.1781(7) 0.0749(13) Uani 0.46(4) 1 d P A 2
I2 I 0.4893(6) 0.8460(3) 0.2159(7) 0.0826(12) Uani 0.54(4) 1 d P A 1
I2' I 0.4849(9) 0.8400(6) 0.2328(15) 0.1085(18) Uani 0.46(4) 1 d P A 2
C1 C 0.3761(6) 1.0155(4) 0.2839(7) 0.0582(15) Uani 1 1 d . . .
C2 C 0.3000(7) 1.0654(5) 0.3424(8) 0.0710(18) Uani 1 1 d . A .
C3 C 0.2248(8) 1.0292(6) 0.4155(9) 0.083(2) Uani 1 1 d . . .
C4 C 0.2247(8) 0.9431(6) 0.4311(9) 0.087(2) Uani 1 1 d . A .
C5 C 0.2987(8) 0.8920(5) 0.3759(9) 0.079(2) Uani 1 1 d . . .
C6 C 0.3761(7) 0.9268(4) 0.3018(7) 0.0631(16) Uani 1 1 d . A .
C7 C 0.9619(15) -0.2109(7) 0.0861(17) 0.168(7) Uani 1 1 d D . .
H7A H 0.9511 -0.2681 0.1060 0.202 Uiso 1 1 calc R . .
C8 C 0.9023(12) -0.1491(7) 0.1455(14) 0.150(6) Uani 1 1 d D . .
H8A H 0.8559 -0.1632 0.2065 0.179 Uiso 1 1 calc R . .
C9 C 0.9174(10) -0.0624(6) 0.1061(11) 0.117(3) Uani 1 1 d D . .
C10 C 0.8633(10) 0.0032(7) 0.1581(11) 0.141(5) Uani 1 1 d D . .
H10A H 0.8139 -0.0096 0.2168 0.170 Uiso 1 1 calc R . .
C11 C 0.8789(10) 0.0888(6) 0.1271(11) 0.117(4) Uani 1 1 d D . .
H11A H 0.8418 0.1321 0.1661 0.141 Uiso 1 1 calc R . .
C12 C 0.9514(9) 0.1096(5) 0.0359(10) 0.104(3) Uani 1 1 d D . .
C13 C 0.9639(13) 0.1930(6) 0.0006(14) 0.167(6) Uani 1 1 d D . .
H13A H 0.9233 0.2369 0.0342 0.200 Uiso 1 1 calc R . .
C14 C 1.0094(7) 0.0410(4) -0.0202(7) 0.0661(17) Uani 1 1 d D . .
F1 F 0.2989(5) 1.1511(3) 0.3305(6) 0.1002(14) Uani 1 1 d . . .
F2 F 0.1528(5) 1.0783(4) 0.4725(7) 0.1241(19) Uani 1 1 d . A .
F3 F 0.1513(6) 0.9062(4) 0.5024(6) 0.128(2) Uani 1 1 d . . .
F4 F 0.2990(5) 0.8066(3) 0.3933(6) 0.1131(16) Uani 1 1 d . A .

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 0.0863(18) 0.102(3) 0.093(2) -0.0038(16) 0.0498(19) -0.0072(14)
I1' 0.089(2) 0.056(2) 0.071(2) 0.0134(11) 0.0256(18) -0.0155(12)
I2 0.088(2) 0.0687(13) 0.0962(17) 0.0055(17) 0.0440(13) 0.0041(13)
I2' 0.115(3) 0.075(2) 0.120(3) -0.026(2) 0.034(2) 0.025(2)
C1 0.050(3) 0.065(4) 0.055(4) 0.001(3) 0.017(3) 0.001(3)
C2 0.064(4) 0.069(4) 0.069(4) -0.009(3) 0.017(4) -0.005(3)
C3 0.061(4) 0.104(6) 0.082(5) -0.013(5) 0.028(4) 0.007(4)
C4 0.064(5) 0.125(7) 0.072(5) 0.002(5) 0.028(4) -0.013(5)
C5 0.070(5) 0.076(5) 0.075(5) 0.011(4) 0.014(4) -0.014(4)
C6 0.056(4) 0.061(4) 0.061(4) -0.003(3) 0.014(3) -0.001(3)
C7 0.116(12) 0.153(13) 0.179(15) 0.056(12) 0.007(9) -0.034(10)
C8 0.089(8) 0.142(11) 0.154(12) 0.071(10) -0.012(7) -0.035(7)
C9 0.071(6) 0.176(11) 0.088(7) 0.025(7) 0.016(5) -0.005(6)
C10 0.083(7) 0.237(15) 0.088(7) -0.043(10) 0.020(5) 0.024(9)
C11 0.093(7) 0.146(9) 0.102(7) -0.050(7) 0.031(6) 0.043(7)
C12 0.088(6) 0.082(6) 0.096(7) -0.007(5) -0.007(5) 0.008(5)
C13 0.130(11) 0.100(9) 0.184(14) -0.040(9) -0.018(9) 0.023(7)
C14 0.049(3) 0.074(4) 0.060(4) 0.005(3) 0.009(3) 0.002(3)
F1 0.107(3) 0.073(3) 0.114(4) -0.013(2) 0.039(3) 0.010(2)
F2 0.091(3) 0.172(5) 0.118(4) -0.034(4) 0.053(3) 0.018(3)
F3 0.105(4) 0.186(6) 0.107(4) 0.004(4) 0.057(3) -0.042(4)
F4 0.117(4) 0.086(3) 0.123(4) 0.027(3) 0.038(3) -0.024(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 C1 2.106(8) . ?
I1' C1 2.039(8) . ?
I2 C6 2.111(8) . ?
I2' C6 2.039(10) . ?
C1 C2 1.384(9) . ?
C1 C6 1.394(9) . ?
C2 F1 1.341(8) . ?
C2 C3 1.371(11) . ?
C3 F2 1.336(9) . ?
C3 C4 1.352(11) . ?
C4 F3 1.349(9) . ?
C4 C5 1.358(11) . ?
C5 F4 1.341(8) . ?
C5 C6 1.387(10) . ?
C7 C13 1.380(16) 3_755 ?
C7 C8 1.390(9) . ?
C7 H7A 0.9300 . ?
C8 C9 1.432(8) . ?
C8 H8A 0.9300 . ?
C9 C10 1.359(8) . ?
C9 C14 1.379(11) 3_755 ?
C10 C11 1.393(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.413(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.365(8) . ?
C12 C14 1.439(7) . ?
C13 C7 1.380(16) 3_755 ?
C13 H13A 0.9300 . ?
C14 C14 1.376(13) 3_755 ?
C14 C9 1.379(11) 3_755 ?

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 C6 118.5(6) . . ?
C2 C1 I1' 115.4(6) . . ?
C6 C1 I1' 126.1(6) . . ?
C2 C1 I1 119.9(5) . . ?
C6 C1 I1 121.6(5) . . ?
I1' C1 I1 4.5(3) . . ?
F1 C2 C3 118.0(7) . . ?
F1 C2 C1 120.7(7) . . ?
C3 C2 C1 121.3(7) . . ?
F2 C3 C4 119.7(8) . . ?
F2 C3 C2 120.7(8) . . ?
C4 C3 C2 119.6(7) . . ?
F3 C4 C3 120.5(8) . . ?
F3 C4 C5 118.6(8) . . ?
C3 C4 C5 120.8(7) . . ?
F4 C5 C4 120.2(8) . . ?
F4 C5 C6 118.9(8) . . ?
C4 C5 C6 120.9(7) . . ?
C5 C6 C1 118.9(7) . . ?
C5 C6 I2' 115.0(7) . . ?
C1 C6 I2' 126.0(7) . . ?
C5 C6 I2 120.2(5) . . ?
C1 C6 I2 120.9(5) . . ?
I2' C6 I2 5.4(5) . . ?
C13 C7 C8 124.4(11) 3_755 . ?
C13 C7 H7A 117.8 3_755 . ?
C8 C7 H7A 117.8 . . ?
C7 C8 C9 115.3(9) . . ?
C7 C8 H8A 122.4 . . ?
C9 C8 H8A 122.4 . . ?
C10 C9 C14 117.2(7) . 3_755 ?
C10 C9 C8 120.3(8) . . ?
C14 C9 C8 122.5(7) 3_755 . ?
C9 C10 C11 122.6(7) . . ?
C9 C10 H10A 118.7 . . ?
C11 C10 H10A 118.7 . . ?
C10 C11 C12 119.6(6) . . ?
C10 C11 H11A 120.2 . . ?
C12 C11 H11A 120.2 . . ?
C13 C12 C11 120.4(8) . . ?
C13 C12 C14 121.0(8) . . ?
C11 C12 C14 118.6(6) . . ?
C12 C13 C7 118.7(11) . 3_755 ?
C12 C13 H13A 120.6 . . ?
C7 C13 H13A 120.6 3_755 . ?
C14 C14 C9 125.1(8) 3_755 3_755 ?
C14 C14 C12 116.9(7) 3_755 . ?
C9 C14 C12 118.0(6) 3_755 . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.095



_database_code_depnum_ccdc_archive 'CCDC 742961'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Cocrystal_1
#TrackingRef '- Cocrystal 1 and 2.cif'




_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C22 H10 F4 I2'

_chemical_formula_weight         604.10



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'
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'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   P2(1)/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                   8.3885(2)

_cell_length_b                   18.3017(4)

_cell_length_c                   13.1838(4)

_cell_angle_alpha                90.00

_cell_angle_beta                 105.2680(10)

_cell_angle_gamma                90.00

_cell_volume                     1952.59(9)

_cell_formula_units_Z            4

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    3892

_cell_measurement_theta_min      2.74

_cell_measurement_theta_max      26.34



_exptl_crystal_description       ?

_exptl_crystal_colour            ?

_exptl_crystal_size_max          0.22

_exptl_crystal_size_mid          0.11

_exptl_crystal_size_min          0.11

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    2.055

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1136

_exptl_absorpt_coefficient_mu    3.262

_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_correction_T_min  0.5339

_exptl_absorpt_correction_T_max  0.7155

_exptl_absorpt_process_details   SADABS



_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  '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            9480

_diffrn_reflns_av_R_equivalents  0.0167

_diffrn_reflns_av_sigmaI/netI    0.0235

_diffrn_reflns_limit_h_min       -10

_diffrn_reflns_limit_h_max       10

_diffrn_reflns_limit_k_min       -23

_diffrn_reflns_limit_k_max       16

_diffrn_reflns_limit_l_min       -17

_diffrn_reflns_limit_l_max       15

_diffrn_reflns_theta_min         1.95

_diffrn_reflns_theta_max         27.57

_reflns_number_total             4472

_reflns_number_gt                3229

_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 F^2^ against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F^2^, conventional R-factors R are based

on F, with F set to zero for negative F^2^. The threshold expression of

F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F^2^ 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/[\s^2^(Fo^2^)+(0.0455P)^2^+1.9804P] where P=(Fo^2^+2Fc^2^)/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         4472

_refine_ls_number_parameters     253

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0560

_refine_ls_R_factor_gt           0.0373

_refine_ls_wR_factor_ref         0.0991

_refine_ls_wR_factor_gt          0.0889

_refine_ls_goodness_of_fit_ref   1.016

_refine_ls_restrained_S_all      1.016

_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 0.5917(6) 0.5646(3) 0.4431(4) 0.0641(11) Uani 1 1 d . . .
H1 H 0.6681 0.5392 0.4951 0.077 Uiso 1 1 calc R . .
C2 C 0.5275(6) 0.6268(3) 0.4682(3) 0.0633(11) Uani 1 1 d . . .
H2 H 0.5611 0.6438 0.5370 0.076 Uiso 1 1 calc R . .
C3 C 0.4085(5) 0.6678(2) 0.3919(3) 0.0529(9) Uani 1 1 d . . .
C4 C 0.3375(6) 0.7325(3) 0.4162(4) 0.0674(12) Uani 1 1 d . . .
H4 H 0.3666 0.7500 0.4848 0.081 Uiso 1 1 calc R . .
C5 C 0.2251(6) 0.7704(3) 0.3394(5) 0.0719(13) Uani 1 1 d . . .
H5 H 0.1794 0.8134 0.3568 0.086 Uiso 1 1 calc R . .
C6 C 0.1794(6) 0.7459(2) 0.2377(4) 0.0671(12) Uani 1 1 d . . .
H6 H 0.1032 0.7726 0.1872 0.081 Uiso 1 1 calc R . .
C7 C 0.2453(5) 0.6818(2) 0.2086(3) 0.0546(10) Uani 1 1 d . . .
C8 C 0.1988(6) 0.6529(3) 0.1046(4) 0.0693(12) Uani 1 1 d . . .
H8 H 0.1207 0.6777 0.0529 0.083 Uiso 1 1 calc R . .
C9 C 0.2643(6) 0.5910(3) 0.0791(4) 0.0659(12) Uani 1 1 d . . .
H9 H 0.2317 0.5744 0.0101 0.079 Uiso 1 1 calc R . .
C10 C 0.3832(5) 0.5498(2) 0.1555(3) 0.0544(10) Uani 1 1 d . . .
C11 C 0.4514(6) 0.4848(3) 0.1323(4) 0.0658(12) Uani 1 1 d . . .
H11 H 0.4218 0.4669 0.0638 0.079 Uiso 1 1 calc R . .
C12 C 0.5631(6) 0.4463(3) 0.2101(5) 0.0700(13) Uani 1 1 d . . .
H12 H 0.6073 0.4028 0.1932 0.084 Uiso 1 1 calc R . .
C13 C 0.6092(6) 0.4712(2) 0.3111(4) 0.0646(12) Uani 1 1 d . . .
H13 H 0.6839 0.4444 0.3621 0.077 Uiso 1 1 calc R . .
C14 C 0.5459(5) 0.5362(2) 0.3386(3) 0.0511(9) Uani 1 1 d . . .
C15 C 0.4307(4) 0.5763(2) 0.2603(3) 0.0444(8) Uani 1 1 d . . .
C16 C 0.3625(4) 0.6421(2) 0.2866(3) 0.0453(8) Uani 1 1 d . . .
C17 C 0.8045(5) 0.6973(2) 0.2900(4) 0.0520(9) Uani 1 1 d . . .
C18 C 0.7778(5) 0.6613(3) 0.1959(3) 0.0586(10) Uani 1 1 d . . .
C19 C 0.8492(5) 0.5953(2) 0.1887(3) 0.0574(10) Uani 1 1 d . . .
C20 C 0.9509(5) 0.5614(2) 0.2764(4) 0.0519(9) Uani 1 1 d . . .
C21 C 0.9771(5) 0.5971(2) 0.3704(3) 0.0548(10) Uani 1 1 d . . .
C22 C 0.9053(5) 0.6637(2) 0.3771(3) 0.0557(10) Uani 1 1 d . . .
F1 F 0.6819(4) 0.69137(18) 0.1081(2) 0.0939(10) Uani 1 1 d . . .
F2 F 0.8223(4) 0.56299(18) 0.0943(2) 0.0867(9) Uani 1 1 d . . .
F3 F 1.0738(4) 0.56771(16) 0.4578(2) 0.0825(8) Uani 1 1 d . . .
F4 F 0.9359(4) 0.69636(16) 0.4717(2) 0.0824(8) Uani 1 1 d . . .
I1 I 0.70088(4) 0.798954(17) 0.30026(3) 0.07962(15) Uani 1 1 d . . .
I2 I 1.05707(4) 0.460654(16) 0.26372(3) 0.07366(14) 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




























C1 0.056(3) 0.075(3) 0.055(3) 0.015(2) 0.002(2) -0.006(2)
C2 0.065(3) 0.077(3) 0.043(2) -0.004(2) 0.007(2) -0.014(2)
C3 0.052(2) 0.051(2) 0.058(3) -0.0046(19) 0.020(2) -0.0126(18)
C4 0.068(3) 0.066(3) 0.074(3) -0.017(2) 0.030(3) -0.016(2)
C5 0.070(3) 0.056(3) 0.099(4) -0.008(3) 0.037(3) -0.004(2)
C6 0.058(3) 0.054(3) 0.091(4) 0.017(2) 0.024(2) 0.006(2)
C7 0.050(2) 0.054(2) 0.060(3) 0.0118(19) 0.0155(19) -0.0063(18)
C8 0.072(3) 0.075(3) 0.055(3) 0.020(2) 0.007(2) -0.002(2)
C9 0.075(3) 0.076(3) 0.042(2) 0.003(2) 0.007(2) -0.010(2)
C10 0.057(2) 0.056(2) 0.054(3) -0.0039(19) 0.021(2) -0.0142(19)
C11 0.072(3) 0.063(3) 0.067(3) -0.017(2) 0.028(2) -0.015(2)
C12 0.066(3) 0.048(2) 0.103(4) -0.010(3) 0.036(3) -0.010(2)
C13 0.050(2) 0.055(3) 0.088(4) 0.011(2) 0.018(2) -0.0029(19)
C14 0.046(2) 0.048(2) 0.060(3) 0.0060(18) 0.0144(18) -0.0080(16)
C15 0.0421(19) 0.0441(19) 0.048(2) 0.0036(16) 0.0143(16) -0.0118(15)
C16 0.0413(18) 0.0450(19) 0.050(2) 0.0041(16) 0.0137(16) -0.0101(15)
C17 0.047(2) 0.0408(19) 0.070(3) 0.0021(18) 0.018(2) -0.0043(16)
C18 0.048(2) 0.062(3) 0.060(3) 0.008(2) 0.003(2) -0.0008(19)
C19 0.053(2) 0.061(3) 0.055(3) -0.012(2) 0.008(2) -0.0119(19)
C20 0.042(2) 0.0416(19) 0.071(3) -0.0020(19) 0.0142(19) -0.0065(15)
C21 0.051(2) 0.052(2) 0.057(3) 0.0046(19) 0.0054(19) -0.0069(18)
C22 0.061(2) 0.049(2) 0.056(3) -0.0049(19) 0.015(2) -0.0129(19)
F1 0.090(2) 0.103(2) 0.0728(19) 0.0172(17) -0.0054(16) 0.0210(18)
F2 0.091(2) 0.097(2) 0.0645(17) -0.0280(15) 0.0059(15) -0.0060(17)
F3 0.087(2) 0.0806(19) 0.0673(18) 0.0171(14) -0.0027(15) 0.0076(16)
F4 0.104(2) 0.0770(18) 0.0642(17) -0.0197(14) 0.0193(16) -0.0128(16)
I1 0.0810(2) 0.04707(18) 0.1238(3) 0.00833(16) 0.0500(2) 0.00258(14)
I2 0.05875(19) 0.04936(18) 0.1158(3) -0.00736(16) 0.02814(18) -0.00326(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









































C1 C2 1.338(7) . ?
C1 C14 1.427(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.429(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(6) . ?
C3 C16 1.419(6) . ?
C4 C5 1.376(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.393(6) . ?
C6 H6 0.9300 . ?
C7 C16 1.422(6) . ?
C7 C8 1.425(7) . ?
C8 C9 1.341(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.431(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.389(6) . ?
C10 C15 1.419(6) . ?
C11 C12 1.386(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.419(6) . ?
C15 C16 1.414(5) . ?
C17 C18 1.369(6) . ?
C17 C22 1.378(6) . ?
C17 I1 2.074(4) . ?
C18 F1 1.341(5) . ?
C18 C19 1.363(6) . ?
C19 F2 1.343(5) . ?
C19 C20 1.389(6) . ?
C20 C21 1.367(6) . ?
C20 I2 2.073(4) . ?
C21 F3 1.335(5) . ?
C21 C22 1.372(6) . ?
C22 F4 1.346(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


































































C2 C1 C14 121.7(4) . . ?
C2 C1 H1 119.2 . . ?
C14 C1 H1 119.2 . . ?
C1 C2 C3 121.6(4) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C16 118.8(4) . . ?
C4 C3 C2 122.9(4) . . ?
C16 C3 C2 118.3(4) . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 121.1(5) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 121.1(5) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C16 118.7(4) . . ?
C6 C7 C8 123.4(4) . . ?
C16 C7 C8 117.9(4) . . ?
C9 C8 C7 121.9(4) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C10 121.6(4) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C11 C10 C15 118.8(4) . . ?
C11 C10 C9 123.2(4) . . ?
C15 C10 C9 118.0(4) . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 121.1(5) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.8(5) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 119.1(4) . . ?
C13 C14 C1 122.7(4) . . ?
C15 C14 C1 118.2(4) . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 C10 120.1(4) . . ?
C14 C15 C10 119.6(4) . . ?
C15 C16 C3 119.9(4) . . ?
C15 C16 C7 120.4(4) . . ?
C3 C16 C7 119.7(4) . . ?
C18 C17 C22 117.3(4) . . ?
C18 C17 I1 121.3(3) . . ?
C22 C17 I1 121.4(3) . . ?
F1 C18 C19 118.6(4) . . ?
F1 C18 C17 120.2(4) . . ?
C19 C18 C17 121.2(4) . . ?
F2 C19 C18 119.0(4) . . ?
F2 C19 C20 119.4(4) . . ?
C18 C19 C20 121.6(4) . . ?
C21 C20 C19 117.2(4) . . ?
C21 C20 I2 121.9(3) . . ?
C19 C20 I2 120.9(3) . . ?
F3 C21 C20 120.3(4) . . ?
F3 C21 C22 118.7(4) . . ?
C20 C21 C22 121.0(4) . . ?
F4 C22 C21 118.3(4) . . ?
F4 C22 C17 120.0(4) . . ?
C21 C22 C17 121.7(4) . . ?



_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        27.57

_diffrn_measured_fraction_theta_full 0.990

_refine_diff_density_max         0.835

_refine_diff_density_min         -1.295

_refine_diff_density_rms         0.110
_database_code_depnum_ccdc_archive 'CCDC 803991'