# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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_RR2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(1R,2R)-1,2-diphenyl-1,2-bis
(2,3,5,6-tetrafluoro-4-iodophenoxy)ethane
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H12 F8 I2 O2'

_chemical_formula_sum            'C26 H12 F8 I2 O2'
_chemical_formula_weight         762.16
_chemical_absolute_configuration syn


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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'


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

_cell_length_a                   8.0352(2)
_cell_length_b                   16.1215(3)
_cell_length_c                   20.0537(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2597.75(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10107
_cell_measurement_theta_min      3.5752
_cell_measurement_theta_max      27.4971

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.87
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.949
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1448
_exptl_absorpt_coefficient_mu    2.501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.286
_exptl_absorpt_correction_T_max  0.387

#----------------------------- Remark ------------------------------------#
# SADABS output:                                                          #
# Estimated minimum and maximum transmission:  0.4275  0.7456             #
# The ratio of these values is more reliable than their absolute values!  #
#-------------------------------------------------------------------------#

_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_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_method       CCD
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5860
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.51
_reflns_number_total             5860
_reflns_number_gt                5226
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0558P)²+4.9712P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_number_reflns         5860
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1269
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.59987(8) 1.13029(3) -0.08162(2) 0.07348(15) Uani 1 1 d . . .
I2 I 0.59529(8) 0.30105(3) 0.06377(3) 0.08417(19) Uani 1 1 d . . .
F1 F 0.6976(7) 0.9444(3) -0.1195(2) 0.0841(13) Uani 1 1 d . . .
F2 F 0.7651(7) 0.8079(2) -0.0495(2) 0.0814(14) Uani 1 1 d . . .
F3 F 0.5728(6) 1.0971(2) 0.07551(19) 0.0713(10) Uani 1 1 d . . .
F4 F 0.6052(7) 0.9620(2) 0.14912(17) 0.0699(10) Uani 1 1 d . . .
F5 F 0.7390(6) 0.4629(3) -0.0069(2) 0.0775(12) Uani 1 1 d . . .
F6 F 0.7606(6) 0.6210(2) 0.03262(18) 0.0740(11) Uani 1 1 d . . .
F7 F 0.4720(6) 0.3939(3) 0.1960(2) 0.0767(12) Uani 1 1 d . . .
F8 F 0.4823(6) 0.5534(3) 0.23288(18) 0.0714(10) Uani 1 1 d . . .
O1 O 0.6959(6) 0.8077(2) 0.0857(2) 0.0585(10) Uani 1 1 d . . .
O2 O 0.6249(5) 0.6716(2) 0.1548(2) 0.0525(9) Uani 1 1 d . . .
C1 C 0.6370(8) 1.0248(4) -0.0234(3) 0.0533(14) Uani 1 1 d . . .
C2 C 0.6804(9) 0.9494(4) -0.0519(3) 0.0574(14) Uani 1 1 d . . .
C3 C 0.7025(8) 0.8803(4) -0.0146(3) 0.0539(13) Uani 1 1 d . . .
C4 C 0.6810(7) 0.8815(3) 0.0549(3) 0.0473(11) Uani 1 1 d . . .
C5 C 0.6374(7) 0.9561(4) 0.0828(3) 0.0523(13) Uani 1 1 d . . .
C6 C 0.6206(8) 1.0262(3) 0.0439(3) 0.0521(13) Uani 1 1 d . . .
C7 C 0.7571(8) 0.8030(3) 0.1543(3) 0.0478(12) Uani 1 1 d . . .
H7 H 0.6704 0.8219 0.1851 0.057 Uiso 1 1 calc R . .
C8 C 0.9116(8) 0.8532(3) 0.1643(3) 0.0479(11) Uani 1 1 d . . .
C9 C 0.9293(9) 0.9018(4) 0.2208(3) 0.0619(16) Uani 1 1 d . . .
H9 H 0.8428 0.9050 0.2515 0.074 Uiso 1 1 calc R . .
C10 C 1.0731(11) 0.9451(5) 0.2317(4) 0.080(2) Uani 1 1 d . . .
H10 H 1.0828 0.9784 0.2694 0.096 Uiso 1 1 calc R . .
C11 C 1.2048(12) 0.9398(6) 0.1870(4) 0.085(2) Uani 1 1 d . . .
H11 H 1.3030 0.9687 0.1949 0.102 Uiso 1 1 calc R . .
C12 C 1.1892(10) 0.8916(6) 0.1309(4) 0.078(2) Uani 1 1 d . . .
H12 H 1.2766 0.8886 0.1006 0.093 Uiso 1 1 calc R . .
C13 C 1.0450(9) 0.8474(4) 0.1190(3) 0.0615(16) Uani 1 1 d . . .
H13 H 1.0361 0.8141 0.0813 0.074 Uiso 1 1 calc R . .
C14 C 0.7890(8) 0.7097(3) 0.1646(3) 0.0479(12) Uani 1 1 d . . .
H14 H 0.8658 0.6896 0.1302 0.057 Uiso 1 1 calc R . .
C15 C 0.8578(7) 0.6902(3) 0.2320(3) 0.0497(12) Uani 1 1 d . . .
C16 C 0.7616(10) 0.6879(4) 0.2888(3) 0.0600(15) Uani 1 1 d . . .
H16 H 0.6478 0.6977 0.2854 0.072 Uiso 1 1 calc R . .
C17 C 0.8294(12) 0.6715(5) 0.3502(4) 0.074(2) Uani 1 1 d . . .
H17 H 0.7615 0.6713 0.3877 0.088 Uiso 1 1 calc R . .
C18 C 0.9929(13) 0.6557(5) 0.3567(5) 0.083(2) Uani 1 1 d . . .
H18 H 1.0370 0.6427 0.3983 0.099 Uiso 1 1 calc R . .
C19 C 1.0942(13) 0.6589(6) 0.3018(4) 0.088(2) Uani 1 1 d . . .
H19 H 1.2080 0.6499 0.3063 0.105 Uiso 1 1 calc R . .
C20 C 1.0265(10) 0.6754(5) 0.2396(4) 0.0733(19) Uani 1 1 d . . .
H20 H 1.0956 0.6766 0.2024 0.088 Uiso 1 1 calc R . .
C21 C 0.6262(8) 0.5906(3) 0.1351(3) 0.0480(12) Uani 1 1 d . . .
C22 C 0.6881(8) 0.5640(4) 0.0743(3) 0.0538(13) Uani 1 1 d . . .
C23 C 0.6774(9) 0.4833(4) 0.0546(3) 0.0548(14) Uani 1 1 d . . .
C24 C 0.6075(8) 0.4242(3) 0.0943(3) 0.0537(13) Uani 1 1 d . . .
C25 C 0.5427(8) 0.4501(4) 0.1548(3) 0.0534(13) Uani 1 1 d . . .
C26 C 0.5518(7) 0.5317(4) 0.1747(3) 0.0494(12) 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 2.084(6) . ?
I2 C24 2.080(5) . ?
F1 C2 1.364(7) . ?
F2 C3 1.451(7) . ?
F3 C6 1.361(6) . ?
F4 C5 1.358(7) . ?
F5 C23 1.370(7) . ?
F6 C22 1.373(6) . ?
F7 C25 1.351(7) . ?
F8 C26 1.339(7) . ?
O1 C4 1.346(7) . ?
O1 C7 1.463(7) . ?
O2 C21 1.364(6) . ?
O2 C14 1.468(7) . ?
C1 C6 1.357(9) . ?
C1 C2 1.388(9) . ?
C2 C3 1.354(9) . ?
C3 C4 1.403(8) . ?
C4 C5 1.373(8) . ?
C5 C6 1.380(8) . ?
C7 C8 1.494(8) . ?
C7 C14 1.540(7) . ?
C7 H7 0.9800 . ?
C8 C9 1.385(8) . ?
C8 C13 1.408(9) . ?
C9 C10 1.368(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(10) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.493(8) . ?
C14 H14 0.9800 . ?
C15 C16 1.378(9) . ?
C15 C20 1.385(10) . ?
C16 C17 1.372(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.345(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.369(14) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(11) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.375(8) . ?
C21 C22 1.385(9) . ?
C22 C23 1.362(8) . ?
C23 C24 1.362(9) . ?
C24 C25 1.385(9) . ?
C25 C26 1.377(8) . ?

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
C4 O1 C7 120.5(4) . . ?
C21 O2 C14 115.6(4) . . ?
C6 C1 C2 116.7(5) . . ?
C6 C1 I1 122.0(5) . . ?
C2 C1 I1 121.3(5) . . ?
C3 C2 F1 119.1(6) . . ?
C3 C2 C1 121.7(6) . . ?
F1 C2 C1 119.1(6) . . ?
C2 C3 C4 121.5(5) . . ?
C2 C3 F2 116.1(5) . . ?
C4 C3 F2 122.2(5) . . ?
O1 C4 C5 127.5(5) . . ?
O1 C4 C3 115.7(5) . . ?
C5 C4 C3 116.6(5) . . ?
F4 C5 C4 120.6(5) . . ?
F4 C5 C6 118.5(5) . . ?
C4 C5 C6 120.8(5) . . ?
C1 C6 F3 120.3(5) . . ?
C1 C6 C5 122.6(5) . . ?
F3 C6 C5 116.9(5) . . ?
O1 C7 C8 112.2(5) . . ?
O1 C7 C14 103.4(4) . . ?
C8 C7 C14 111.9(5) . . ?
O1 C7 H7 109.7 . . ?
C8 C7 H7 109.7 . . ?
C14 C7 H7 109.7 . . ?
C9 C8 C13 119.1(6) . . ?
C9 C8 C7 120.1(6) . . ?
C13 C8 C7 120.7(5) . . ?
C10 C9 C8 120.5(7) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.5(7) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.6(7) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.7(7) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 119.6(6) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
O2 C14 C15 111.4(5) . . ?
O2 C14 C7 104.0(5) . . ?
C15 C14 C7 112.8(4) . . ?
O2 C14 H14 109.5 . . ?
C15 C14 H14 109.5 . . ?
C7 C14 H14 109.5 . . ?
C16 C15 C20 116.9(6) . . ?
C16 C15 C14 123.1(5) . . ?
C20 C15 C14 120.0(6) . . ?
C17 C16 C15 121.7(7) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C18 C17 C16 120.8(8) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.7(9) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 119.8(9) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 121.1(8) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
O2 C21 C26 119.3(5) . . ?
O2 C21 C22 123.7(5) . . ?
C26 C21 C22 116.8(5) . . ?
C23 C22 F6 119.3(6) . . ?
C23 C22 C21 121.9(5) . . ?
F6 C22 C21 118.8(5) . . ?
C22 C23 C24 121.6(6) . . ?
C22 C23 F5 117.9(6) . . ?
C24 C23 F5 120.5(5) . . ?
C23 C24 C25 117.1(5) . . ?
C23 C24 I2 121.0(5) . . ?
C25 C24 I2 121.8(4) . . ?
F7 C25 C26 119.0(6) . . ?
F7 C25 C24 119.5(5) . . ?
C26 C25 C24 121.5(5) . . ?
F8 C26 C21 120.3(5) . . ?
F8 C26 C25 118.7(5) . . ?
C21 C26 C25 120.9(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.2(10) . . . . ?
I1 C1 C2 C3 -179.0(5) . . . . ?
C6 C1 C2 F1 179.6(6) . . . . ?
I1 C1 C2 F1 -0.6(9) . . . . ?
F1 C2 C3 C4 -177.9(6) . . . . ?
C1 C2 C3 C4 0.5(10) . . . . ?
F1 C2 C3 F2 8.0(9) . . . . ?
C1 C2 C3 F2 -173.6(6) . . . . ?
C7 O1 C4 C5 -34.6(9) . . . . ?
C7 O1 C4 C3 149.8(5) . . . . ?
C2 C3 C4 O1 175.9(6) . . . . ?
F2 C3 C4 O1 -10.4(8) . . . . ?
C2 C3 C4 C5 -0.3(9) . . . . ?
F2 C3 C4 C5 173.5(5) . . . . ?
O1 C4 C5 F4 0.8(10) . . . . ?
C3 C4 C5 F4 176.4(5) . . . . ?
O1 C4 C5 C6 -177.3(6) . . . . ?
C3 C4 C5 C6 -1.7(9) . . . . ?
C2 C1 C6 F3 -177.8(6) . . . . ?
I1 C1 C6 F3 2.4(8) . . . . ?
C2 C1 C6 C5 -3.2(9) . . . . ?
I1 C1 C6 C5 177.0(5) . . . . ?
F4 C5 C6 C1 -174.5(6) . . . . ?
C4 C5 C6 C1 3.6(10) . . . . ?
F4 C5 C6 F3 0.2(9) . . . . ?
C4 C5 C6 F3 178.3(5) . . . . ?
C4 O1 C7 C8 -48.0(7) . . . . ?
C4 O1 C7 C14 -168.7(5) . . . . ?
O1 C7 C8 C9 136.9(6) . . . . ?
C14 C7 C8 C9 -107.4(6) . . . . ?
O1 C7 C8 C13 -47.4(8) . . . . ?
C14 C7 C8 C13 68.3(7) . . . . ?
C13 C8 C9 C10 1.4(10) . . . . ?
C7 C8 C9 C10 177.2(7) . . . . ?
C8 C9 C10 C11 -1.2(13) . . . . ?
C9 C10 C11 C12 1.0(15) . . . . ?
C10 C11 C12 C13 -0.9(15) . . . . ?
C11 C12 C13 C8 1.1(13) . . . . ?
C9 C8 C13 C12 -1.4(10) . . . . ?
C7 C8 C13 C12 -177.1(7) . . . . ?
C21 O2 C14 C15 -83.2(6) . . . . ?
C21 O2 C14 C7 155.0(4) . . . . ?
O1 C7 C14 O2 -60.7(5) . . . . ?
C8 C7 C14 O2 178.4(4) . . . . ?
O1 C7 C14 C15 178.4(5) . . . . ?
C8 C7 C14 C15 57.5(6) . . . . ?
O2 C14 C15 C16 -39.1(7) . . . . ?
C7 C14 C15 C16 77.5(7) . . . . ?
O2 C14 C15 C20 142.4(6) . . . . ?
C7 C14 C15 C20 -101.0(7) . . . . ?
C20 C15 C16 C17 -0.1(10) . . . . ?
C14 C15 C16 C17 -178.6(6) . . . . ?
C15 C16 C17 C18 -1.1(12) . . . . ?
C16 C17 C18 C19 2.3(13) . . . . ?
C17 C18 C19 C20 -2.2(14) . . . . ?
C16 C15 C20 C19 0.2(11) . . . . ?
C14 C15 C20 C19 178.7(7) . . . . ?
C18 C19 C20 C15 1.0(13) . . . . ?
C14 O2 C21 C26 119.8(6) . . . . ?
C14 O2 C21 C22 -65.2(7) . . . . ?
O2 C21 C22 C23 -175.7(6) . . . . ?
C26 C21 C22 C23 -0.5(10) . . . . ?
O2 C21 C22 F6 3.6(9) . . . . ?
C26 C21 C22 F6 178.8(6) . . . . ?
F6 C22 C23 C24 179.6(6) . . . . ?
C21 C22 C23 C24 -1.1(11) . . . . ?
F6 C22 C23 F5 -0.6(10) . . . . ?
C21 C22 C23 F5 178.7(6) . . . . ?
C22 C23 C24 C25 2.0(10) . . . . ?
F5 C23 C24 C25 -177.7(6) . . . . ?
C22 C23 C24 I2 -179.2(5) . . . . ?
F5 C23 C24 I2 1.1(9) . . . . ?
C23 C24 C25 F7 -180.0(6) . . . . ?
I2 C24 C25 F7 1.3(9) . . . . ?
C23 C24 C25 C26 -1.4(10) . . . . ?
I2 C24 C25 C26 179.8(5) . . . . ?
O2 C21 C26 F8 -1.7(9) . . . . ?
C22 C21 C26 F8 -177.0(6) . . . . ?
O2 C21 C26 C25 176.4(6) . . . . ?
C22 C21 C26 C25 1.1(9) . . . . ?
F7 C25 C26 F8 -3.4(9) . . . . ?
C24 C25 C26 F8 178.0(6) . . . . ?
F7 C25 C26 C21 178.4(6) . . . . ?
C24 C25 C26 C21 -0.1(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.131
_refine_diff_density_min         -0.821
_refine_diff_density_rms         0.083
_database_code_depnum_ccdc_archive 'CCDC 1025195'
#######################################################################
#
#                 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_RR-3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
(S)-2,2'-bis(2,3,5,6-tetrafluoro-4-iodophenoxy)-1,1'-binaphthalene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H12 F8 I2 O2'
_chemical_formula_sum            'C32 H12 F8 I2 O2'
_chemical_formula_weight         834.22

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'
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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P21ca
_symmetry_space_group_name_Hall  'P -2ac 2a'

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

_cell_length_a                   8.9564(3)
_cell_length_b                   13.3787(4)
_cell_length_c                   23.5539(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2822.35(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5769
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      27.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.963
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1592
_exptl_absorpt_coefficient_mu    2.312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_T_max  0.933

#----------------------------- Remark ------------------------------#
# Tmax and Tmin values correspond to EXPECTED values calculated     #
# from crystal size. In the case of absorption correction performed #
# with SADABS program, Tmax should be given as Tmax_expected and    #
# and Tmin = Tmax * 'relative-correction-factor'.                   #
# SADABS output:                                                    #
# Ratio of minimum to maximum apparent transmission:  0.80700       #
#-------------------------------------------------------------------#



_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_method       CCD
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25892
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6435
_reflns_number_gt                3973
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


_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)+(0.0375P)²+2.3928P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_number_reflns         6435
_refine_ls_number_parameters     397
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.020
_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
I1 I 0.34916(7) 0.92414(5) -0.242768(19) 0.0903(2) Uani 1 1 d . . .
I2 I 0.70513(7) 0.48742(4) 0.24895(2) 0.07469(16) Uani 1 1 d . . .
F1 F 0.4953(5) 0.5975(3) -0.12236(15) 0.0660(11) Uani 1 1 d . . .
F2 F 0.5147(6) 0.7216(3) -0.21164(17) 0.0846(13) Uani 1 1 d . . .
F3 F 0.1346(5) 0.9242(3) -0.13346(19) 0.0771(12) Uani 1 1 d . . .
F4 F 0.1202(4) 0.8032(3) -0.04357(18) 0.0678(11) Uani 1 1 d . . .
F5 F 0.8520(5) 0.7114(2) 0.06890(15) 0.0618(9) Uani 1 1 d . . .
F6 F 0.8685(5) 0.6607(3) 0.17779(15) 0.0692(11) Uani 1 1 d . . .
F7 F 0.4968(5) 0.4148(3) 0.14771(16) 0.0670(11) Uani 1 1 d . . .
F8 F 0.4777(4) 0.4708(2) 0.03892(14) 0.0579(9) Uani 1 1 d . . .
O1 O 0.3055(5) 0.6364(3) -0.03451(15) 0.0481(10) Uani 1 1 d . . .
O2 O 0.6571(5) 0.6124(3) -0.00498(17) 0.0463(10) Uani 1 1 d . . .
C1 C 0.3151(7) 0.6768(4) 0.0199(2) 0.0415(13) Uani 1 1 d . . .
C2 C 0.2126(8) 0.6378(4) 0.0589(2) 0.0490(14) Uani 1 1 d . . .
H2 H 0.1409 0.5924 0.0467 0.059 Uiso 1 1 calc R . .
C3 C 0.2166(8) 0.6652(5) 0.1135(3) 0.0549(15) Uani 1 1 d . . .
H3 H 0.1459 0.6403 0.1387 0.066 Uiso 1 1 calc R . .
C4 C 0.3278(8) 0.7317(4) 0.1330(2) 0.0451(14) Uani 1 1 d . . .
C5 C 0.3398(10) 0.7594(5) 0.1917(3) 0.0661(19) Uani 1 1 d . . .
H5 H 0.2699 0.7347 0.2173 0.079 Uiso 1 1 calc R . .
C6 C 0.4474(11) 0.8193(5) 0.2107(3) 0.073(2) Uani 1 1 d . . .
H6 H 0.4533 0.8353 0.2491 0.088 Uiso 1 1 calc R . .
C7 C 0.5532(10) 0.8583(5) 0.1715(3) 0.072(2) Uani 1 1 d . . .
H7 H 0.6301 0.8992 0.1843 0.086 Uiso 1 1 calc R . .
C8 C 0.5426(8) 0.8363(5) 0.1156(2) 0.0502(15) Uani 1 1 d . . .
H8 H 0.6109 0.8644 0.0905 0.060 Uiso 1 1 calc R . .
C9 C 0.4316(6) 0.7723(4) 0.0944(2) 0.0408(13) Uani 1 1 d . . .
C10 C 0.4255(6) 0.7430(4) 0.0356(2) 0.0362(12) Uani 1 1 d . . .
C11 C 0.5416(6) 0.7767(4) -0.0056(2) 0.0368(12) Uani 1 1 d . . .
C12 C 0.6496(6) 0.7134(4) -0.0241(2) 0.0378(13) Uani 1 1 d . . .
C13 C 0.7546(7) 0.7391(5) -0.0656(2) 0.0492(15) Uani 1 1 d . . .
H13 H 0.8265 0.6930 -0.0769 0.059 Uiso 1 1 calc R . .
C14 C 0.7508(7) 0.8320(5) -0.0895(3) 0.0503(15) Uani 1 1 d . . .
H14 H 0.8204 0.8494 -0.1170 0.060 Uiso 1 1 calc R . .
C15 C 0.6422(7) 0.9010(4) -0.0725(2) 0.0398(13) Uani 1 1 d . . .
C16 C 0.6384(8) 0.9980(5) -0.0963(3) 0.0528(16) Uani 1 1 d . . .
H16 H 0.7096 1.0158 -0.1232 0.063 Uiso 1 1 calc R . .
C17 C 0.5321(8) 1.0662(5) -0.0806(3) 0.0538(16) Uani 1 1 d . . .
H17 H 0.5284 1.1290 -0.0974 0.065 Uiso 1 1 calc R . .
C18 C 0.4287(8) 1.0390(4) -0.0385(3) 0.0511(16) Uani 1 1 d . . .
H18 H 0.3563 1.0848 -0.0274 0.061 Uiso 1 1 calc R . .
C19 C 0.4318(7) 0.9487(4) -0.0139(2) 0.0469(14) Uani 1 1 d . . .
H19 H 0.3629 0.9336 0.0144 0.056 Uiso 1 1 calc R . .
C20 C 0.5388(6) 0.8754(4) -0.0303(2) 0.0351(12) Uani 1 1 d . . .
C21 C 0.3125(7) 0.6995(4) -0.0804(2) 0.0430(14) Uani 1 1 d . . .
C22 C 0.4070(7) 0.6793(4) -0.1247(2) 0.0478(16) Uani 1 1 d . . .
C23 C 0.4143(7) 0.7422(5) -0.1711(2) 0.0548(17) Uani 1 1 d . . .
C24 C 0.3255(8) 0.8263(5) -0.1749(2) 0.0549(16) Uani 1 1 d . . .
C25 C 0.2265(7) 0.8437(5) -0.1316(3) 0.0512(15) Uani 1 1 d . . .
C26 C 0.2171(7) 0.7824(5) -0.0849(2) 0.0501(15) Uani 1 1 d . . .
C27 C 0.6631(6) 0.5947(4) 0.0517(2) 0.0393(13) Uani 1 1 d . . .
C28 C 0.7615(7) 0.6384(4) 0.0878(3) 0.0440(14) Uani 1 1 d . . .
C29 C 0.7696(7) 0.6111(5) 0.1438(3) 0.0488(15) Uani 1 1 d . . .
C30 C 0.6816(7) 0.5357(5) 0.1660(2) 0.0463(14) Uani 1 1 d . . .
C31 C 0.5842(7) 0.4897(4) 0.1295(3) 0.0464(15) Uani 1 1 d . . .
C32 C 0.5732(6) 0.5175(4) 0.0733(3) 0.0428(14) 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 C24 2.078(6) . ?
I2 C30 2.068(5) . ?
F1 C22 1.351(7) . ?
F2 C23 1.340(7) . ?
F3 C25 1.356(7) . ?
F4 C26 1.333(7) . ?
F5 C28 1.345(6) . ?
F6 C29 1.366(7) . ?
F7 C31 1.343(6) . ?
F8 C32 1.334(6) . ?
O1 C21 1.372(7) . ?
O1 C1 1.393(6) . ?
O2 C27 1.357(7) . ?
O2 C12 1.425(7) . ?
C1 C10 1.377(8) . ?
C1 C2 1.399(8) . ?
C2 C3 1.339(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.411(9) . ?
C3 H3 0.9300 . ?
C4 C9 1.410(8) . ?
C4 C5 1.435(8) . ?
C5 C6 1.330(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.423(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.352(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.404(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.441(7) . ?
C10 C11 1.492(7) . ?
C11 C12 1.357(8) . ?
C11 C20 1.443(7) . ?
C12 C13 1.399(8) . ?
C13 C14 1.365(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.400(8) . ?
C14 H14 0.9300 . ?
C15 C20 1.401(8) . ?
C15 C16 1.414(8) . ?
C16 C17 1.370(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.405(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.341(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.425(8) . ?
C19 H19 0.9300 . ?
C21 C22 1.371(8) . ?
C21 C26 1.404(9) . ?
C22 C23 1.381(9) . ?
C23 C24 1.380(9) . ?
C24 C25 1.370(9) . ?
C25 C26 1.375(9) . ?
C27 C28 1.356(8) . ?
C27 C32 1.405(8) . ?
C28 C29 1.371(8) . ?
C29 C30 1.384(9) . ?
C30 C31 1.372(8) . ?
C31 C32 1.377(9) . ?

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
C21 O1 C1 118.8(4) . . ?
C27 O2 C12 118.6(4) . . ?
C10 C1 O1 122.7(5) . . ?
C10 C1 C2 122.3(5) . . ?
O1 C1 C2 114.7(5) . . ?
C3 C2 C1 120.8(6) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.3(6) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C9 C4 C3 119.9(5) . . ?
C9 C4 C5 118.2(6) . . ?
C3 C4 C5 122.0(6) . . ?
C6 C5 C4 122.3(6) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C7 119.0(6) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 120.4(7) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.9(6) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C8 C9 C4 118.2(5) . . ?
C8 C9 C10 122.4(5) . . ?
C4 C9 C10 119.4(5) . . ?
C1 C10 C9 117.4(5) . . ?
C1 C10 C11 121.4(5) . . ?
C9 C10 C11 121.0(5) . . ?
C12 C11 C20 117.0(5) . . ?
C12 C11 C10 121.1(5) . . ?
C20 C11 C10 121.8(5) . . ?
C11 C12 C13 123.4(5) . . ?
C11 C12 O2 121.6(5) . . ?
C13 C12 O2 114.9(5) . . ?
C14 C13 C12 119.6(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.0(5) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C20 120.0(5) . . ?
C14 C15 C16 120.6(6) . . ?
C20 C15 C16 119.3(6) . . ?
C17 C16 C15 121.4(6) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 118.4(6) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C19 C18 C17 121.7(6) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 121.1(6) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C15 C20 C19 117.9(5) . . ?
C15 C20 C11 119.9(5) . . ?
C19 C20 C11 122.2(5) . . ?
C22 C21 O1 120.4(5) . . ?
C22 C21 C26 118.2(5) . . ?
O1 C21 C26 121.2(5) . . ?
F1 C22 C21 119.3(5) . . ?
F1 C22 C23 119.8(5) . . ?
C21 C22 C23 120.8(5) . . ?
F2 C23 C24 120.6(6) . . ?
F2 C23 C22 118.1(6) . . ?
C24 C23 C22 121.3(6) . . ?
C25 C24 C23 117.7(5) . . ?
C25 C24 I1 122.0(5) . . ?
C23 C24 I1 120.3(5) . . ?
F3 C25 C24 120.3(6) . . ?
F3 C25 C26 117.5(6) . . ?
C24 C25 C26 122.2(6) . . ?
F4 C26 C25 120.0(6) . . ?
F4 C26 C21 120.3(5) . . ?
C25 C26 C21 119.6(6) . . ?
C28 C27 O2 124.5(5) . . ?
C28 C27 C32 117.5(5) . . ?
O2 C27 C32 117.6(5) . . ?
F5 C28 C27 119.9(5) . . ?
F5 C28 C29 118.6(5) . . ?
C27 C28 C29 121.5(5) . . ?
F6 C29 C28 118.0(5) . . ?
F6 C29 C30 120.1(5) . . ?
C28 C29 C30 121.9(6) . . ?
C31 C30 C29 116.8(5) . . ?
C31 C30 I2 121.2(4) . . ?
C29 C30 I2 121.8(5) . . ?
F7 C31 C30 120.3(6) . . ?
F7 C31 C32 117.9(5) . . ?
C30 C31 C32 121.8(5) . . ?
F8 C32 C31 120.2(5) . . ?
F8 C32 C27 119.5(6) . . ?
C31 C32 C27 120.4(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 O1 C1 C10 -49.6(7) . . . . ?
C21 O1 C1 C2 136.2(6) . . . . ?
C10 C1 C2 C3 1.1(10) . . . . ?
O1 C1 C2 C3 175.4(6) . . . . ?
C1 C2 C3 C4 -2.0(10) . . . . ?
C2 C3 C4 C9 2.4(9) . . . . ?
C2 C3 C4 C5 -177.3(7) . . . . ?
C9 C4 C5 C6 -2.0(10) . . . . ?
C3 C4 C5 C6 177.6(7) . . . . ?
C4 C5 C6 C7 0.9(12) . . . . ?
C5 C6 C7 C8 1.2(12) . . . . ?
C6 C7 C8 C9 -2.1(11) . . . . ?
C7 C8 C9 C4 0.9(10) . . . . ?
C7 C8 C9 C10 -175.7(6) . . . . ?
C3 C4 C9 C8 -178.5(6) . . . . ?
C5 C4 C9 C8 1.1(8) . . . . ?
C3 C4 C9 C10 -1.9(8) . . . . ?
C5 C4 C9 C10 177.8(5) . . . . ?
O1 C1 C10 C9 -174.4(5) . . . . ?
C2 C1 C10 C9 -0.6(8) . . . . ?
O1 C1 C10 C11 0.8(8) . . . . ?
C2 C1 C10 C11 174.6(5) . . . . ?
C8 C9 C10 C1 177.5(6) . . . . ?
C4 C9 C10 C1 1.0(8) . . . . ?
C8 C9 C10 C11 2.3(8) . . . . ?
C4 C9 C10 C11 -174.2(5) . . . . ?
C1 C10 C11 C12 -70.4(8) . . . . ?
C9 C10 C11 C12 104.6(6) . . . . ?
C1 C10 C11 C20 105.4(6) . . . . ?
C9 C10 C11 C20 -79.5(7) . . . . ?
C20 C11 C12 C13 -0.7(9) . . . . ?
C10 C11 C12 C13 175.3(5) . . . . ?
C20 C11 C12 O2 -176.2(5) . . . . ?
C10 C11 C12 O2 -0.2(8) . . . . ?
C27 O2 C12 C11 -55.0(7) . . . . ?
C27 O2 C12 C13 129.1(6) . . . . ?
C11 C12 C13 C14 0.0(9) . . . . ?
O2 C12 C13 C14 175.8(5) . . . . ?
C12 C13 C14 C15 -0.1(9) . . . . ?
C13 C14 C15 C20 1.1(9) . . . . ?
C13 C14 C15 C16 179.1(6) . . . . ?
C14 C15 C16 C17 179.4(6) . . . . ?
C20 C15 C16 C17 -2.6(10) . . . . ?
C15 C16 C17 C18 2.2(10) . . . . ?
C16 C17 C18 C19 -0.2(10) . . . . ?
C17 C18 C19 C20 -1.3(9) . . . . ?
C14 C15 C20 C19 179.1(5) . . . . ?
C16 C15 C20 C19 1.0(8) . . . . ?
C14 C15 C20 C11 -1.8(8) . . . . ?
C16 C15 C20 C11 -179.9(5) . . . . ?
C18 C19 C20 C15 0.9(8) . . . . ?
C18 C19 C20 C11 -178.2(6) . . . . ?
C12 C11 C20 C15 1.7(8) . . . . ?
C10 C11 C20 C15 -174.4(5) . . . . ?
C12 C11 C20 C19 -179.3(5) . . . . ?
C10 C11 C20 C19 4.7(8) . . . . ?
C1 O1 C21 C22 130.8(6) . . . . ?
C1 O1 C21 C26 -53.2(7) . . . . ?
O1 C21 C22 F1 -1.1(8) . . . . ?
C26 C21 C22 F1 -177.2(5) . . . . ?
O1 C21 C22 C23 179.7(5) . . . . ?
C26 C21 C22 C23 3.6(8) . . . . ?
F1 C22 C23 F2 -2.7(9) . . . . ?
C21 C22 C23 F2 176.4(5) . . . . ?
F1 C22 C23 C24 179.9(6) . . . . ?
C21 C22 C23 C24 -1.0(10) . . . . ?
F2 C23 C24 C25 -179.1(6) . . . . ?
C22 C23 C24 C25 -1.9(10) . . . . ?
F2 C23 C24 I1 -1.3(9) . . . . ?
C22 C23 C24 I1 176.0(5) . . . . ?
C23 C24 C25 F3 -178.9(6) . . . . ?
I1 C24 C25 F3 3.3(8) . . . . ?
C23 C24 C25 C26 1.9(10) . . . . ?
I1 C24 C25 C26 -175.9(5) . . . . ?
F3 C25 C26 F4 -0.1(9) . . . . ?
C24 C25 C26 F4 179.1(6) . . . . ?
F3 C25 C26 C21 -178.5(5) . . . . ?
C24 C25 C26 C21 0.8(9) . . . . ?
C22 C21 C26 F4 178.1(5) . . . . ?
O1 C21 C26 F4 2.0(8) . . . . ?
C22 C21 C26 C25 -3.5(8) . . . . ?
O1 C21 C26 C25 -179.6(5) . . . . ?
C12 O2 C27 C28 -51.5(8) . . . . ?
C12 O2 C27 C32 136.3(5) . . . . ?
O2 C27 C28 F5 6.6(9) . . . . ?
C32 C27 C28 F5 178.8(5) . . . . ?
O2 C27 C28 C29 -174.6(5) . . . . ?
C32 C27 C28 C29 -2.3(9) . . . . ?
F5 C28 C29 F6 0.8(8) . . . . ?
C27 C28 C29 F6 -178.0(5) . . . . ?
F5 C28 C29 C30 -179.1(6) . . . . ?
C27 C28 C29 C30 2.1(10) . . . . ?
F6 C29 C30 C31 179.6(5) . . . . ?
C28 C29 C30 C31 -0.5(9) . . . . ?
F6 C29 C30 I2 -4.6(8) . . . . ?
C28 C29 C30 I2 175.3(5) . . . . ?
C29 C30 C31 F7 179.0(5) . . . . ?
I2 C30 C31 F7 3.1(8) . . . . ?
C29 C30 C31 C32 -0.6(9) . . . . ?
I2 C30 C31 C32 -176.5(5) . . . . ?
F7 C31 C32 F8 0.2(8) . . . . ?
C30 C31 C32 F8 179.7(5) . . . . ?
F7 C31 C32 C27 -179.3(5) . . . . ?
C30 C31 C32 C27 0.2(9) . . . . ?
C28 C27 C32 F8 -178.3(5) . . . . ?
O2 C27 C32 F8 -5.5(8) . . . . ?
C28 C27 C32 C31 1.2(8) . . . . ?
O2 C27 C32 C31 174.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.075
_database_code_depnum_ccdc_archive 'CCDC 1025196'
#######################################################################
#
#                 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_RR1-Et3SI

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
6,6'-(((2R,3R)-butane-2,3-diyl)bis(oxy))
bis(1,2,4,5-tetrafluoro-3-iodobenzene),
triethylsulfonium iodide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H8 F8 I2 O2, C6 H15 S, I'
_chemical_formula_sum            'C22 H23 F8 I3 O2 S'
_chemical_formula_weight         884.16
_chemical_absolute_configuration syn

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 2 21 21'
_symmetry_space_group_name_Hall  'P 2bc 2'


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                   11.5706(4)
_cell_length_b                   15.5144(5)
_cell_length_c                   16.0571(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2882.42(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9684
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      27.42


_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.037
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1672
_exptl_absorpt_coefficient_mu    3.395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_T_max  0.665

#----------------------------- Remark ------------------------------------#
# SADABS output:                                                          #
# Estimated minimum and maximum transmission:  0.6078  0.7456             #
# The ratio of these values is more reliable than their absolute values!  #
#-------------------------------------------------------------------------#



_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25659
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         27.47
_reflns_number_total             6604
_reflns_number_gt                5063
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SAINT (Bruker, 2002)'
_computing_cell_refinement       'Bruker SMART (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2002)'
_computing_structure_solution    'SIR97 (ALtomare et al., 1999))'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


_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)+(0.0552P)²+15.8984P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.17(7)
_refine_ls_number_reflns         6604
_refine_ls_number_parameters     339
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1641
_refine_ls_wR_factor_gt          0.1416
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.137
_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
C1 C 2.1157(10) 1.5181(8) 0.0948(9) 0.071(4) Uani 1 1 d . . .
H1A H 2.1090 1.5582 0.1401 0.106 Uiso 1 1 calc R . .
H1B H 2.1872 1.5277 0.0660 0.106 Uiso 1 1 calc R . .
H1C H 2.1142 1.4603 0.1162 0.106 Uiso 1 1 calc R . .
C2 C 2.0158(7) 1.5307(6) 0.0351(7) 0.051(3) Uani 1 1 d . . .
H2 H 1.9440 1.5221 0.0665 0.061 Uiso 1 1 calc R . .
C3 C 1.9206(7) 1.6651(5) 0.0152(6) 0.0314(19) Uani 1 1 d . . .
C4 C 1.8792(12) 1.6990(8) 0.0810(10) 0.056(4) Uani 1 1 d . . .
C5 C 1.7825(13) 1.7538(10) 0.0785(10) 0.065(4) Uani 1 1 d . . .
C6 C 1.7299(7) 1.7761(5) 0.0135(7) 0.037(2) Uani 1 1 d . . .
C7 C 1.7745(13) 1.7433(9) -0.0674(7) 0.048(3) Uani 1 1 d . . .
C8 C 1.8656(12) 1.6890(7) -0.0668(7) 0.044(3) Uani 1 1 d . . .
C9 C 0.8953(11) 1.0199(8) -0.0960(12) 0.097(6) Uani 1 1 d . . .
H9A H 0.8245 1.0339 -0.0679 0.146 Uiso 1 1 calc R . .
H9B H 0.8926 0.9611 -0.1146 0.146 Uiso 1 1 calc R . .
H9C H 0.9050 1.0574 -0.1430 0.146 Uiso 1 1 calc R . .
C10 C 0.9953(8) 1.0314(6) -0.0370(8) 0.061(3) Uani 1 1 d . . .
H10 H 1.0675 1.0241 -0.0681 0.073 Uiso 1 1 calc R . .
C11 C 1.0869(7) 1.1682(5) -0.0101(7) 0.037(2) Uani 1 1 d . . .
C12 C 1.1285(13) 1.2009(9) 0.0727(9) 0.053(3) Uani 1 1 d . . .
C13 C 1.2192(12) 1.2561(10) 0.0781(7) 0.048(3) Uani 1 1 d . . .
C14 C 1.2780(7) 1.2836(7) -0.0022(10) 0.055(3) Uani 1 1 d . . .
C15 C 1.2407(14) 1.2481(10) -0.0664(11) 0.070(4) Uani 1 1 d . . .
C16 C 1.1455(15) 1.1912(8) -0.0703(12) 0.074(5) Uani 1 1 d . . .
O1 O 2.0182(5) 1.6180(4) 0.0075(8) 0.064(2) Uani 1 1 d . . .
O2 O 0.9906(5) 1.1174(4) -0.0057(9) 0.071(3) Uani 1 1 d . . .
F1 F 1.9288(8) 1.6798(5) 0.1525(5) 0.072(2) Uani 1 1 d . . .
F2 F 1.7457(7) 1.7839(6) 0.1516(6) 0.074(2) Uani 1 1 d . . .
F3 F 1.7269(9) 1.7675(6) -0.1410(5) 0.084(3) Uani 1 1 d . . .
F4 F 1.9065(9) 1.6581(5) -0.1408(6) 0.087(3) Uani 1 1 d . . .
F5 F 1.0726(9) 1.1795(5) 0.1460(7) 0.082(3) Uani 1 1 d . . .
F6 F 1.2486(7) 1.2915(6) 0.1528(6) 0.072(2) Uani 1 1 d . . .
F7 F 1.2911(9) 1.2671(6) -0.1399(6) 0.084(3) Uani 1 1 d . . .
F8 F 1.1082(9) 1.1629(5) -0.1450(6) 0.080(3) Uani 1 1 d . . .
I1 I 1.58732(5) 1.86256(4) 0.00665(8) 0.0575(2) Uani 1 1 d . . .
I2 I 1.41981(5) 1.36482(4) 0.00837(8) 0.0616(3) Uani 1 1 d . . .
I3 I 1.65898(6) 1.5000 0.0000 0.0611(3) Uani 1 2 d S . .
I4 I 1.34938(6) 1.0000 0.0000 0.0567(3) Uani 1 2 d S . .
S1A S 1.5731(9) 1.5676(8) 0.2928(7) 0.131(5) Uani 0.523(10) 1 d PD A 1
C17A C 1.438(3) 1.508(3) 0.283(3) 0.159(19) Uiso 0.523(10) 1 d PD A 1
H17A H 1.4663 1.4498 0.2873 0.191 Uiso 0.523(10) 1 calc PR A 1
H17B H 1.4046 1.5197 0.3378 0.191 Uiso 0.523(10) 1 calc PR A 1
C18A C 1.333(4) 1.493(4) 0.236(4) 0.23(3) Uiso 0.523(10) 1 d PD A 1
H18A H 1.2687 1.4879 0.2739 0.343 Uiso 0.523(10) 1 calc PR A 1
H18B H 1.3407 1.4413 0.2045 0.343 Uiso 0.523(10) 1 calc PR A 1
H18C H 1.3195 1.5410 0.1993 0.343 Uiso 0.523(10) 1 calc PR A 1
C19A C 1.6654(17) 1.4805(8) 0.2469(12) 0.126(7) Uani 0.523(10) 1 d PD A 1
H19A H 1.6571 1.4282 0.2795 0.151 Uiso 0.523(10) 1 calc PR A 1
H19B H 1.6402 1.4683 0.1905 0.151 Uiso 0.523(10) 1 calc PR A 1
C20A C 1.7967(13) 1.5094(8) 0.2461(14) 0.104(5) Uani 0.523(10) 1 d P A 1
H20A H 1.8437 1.4631 0.2254 0.155 Uiso 0.523(10) 1 calc PR A 1
H20B H 1.8205 1.5237 0.3017 0.155 Uiso 0.523(10) 1 calc PR A 1
H20C H 1.8056 1.5589 0.2108 0.155 Uiso 0.523(10) 1 calc PR A 1
C21A C 1.590(3) 1.6496(13) 0.2230(15) 0.087(6) Uani 0.523(10) 1 d PD A 1
H21A H 1.6698 1.6672 0.2190 0.105 Uiso 0.523(10) 1 calc PR A 1
H21B H 1.5624 1.6328 0.1682 0.105 Uiso 0.523(10) 1 calc PR A 1
C22A C 1.5128(10) 1.7239(9) 0.2603(15) 0.104(5) Uani 0.523(10) 1 d PD A 1
H22A H 1.5169 1.7736 0.2247 0.155 Uiso 0.523(10) 1 calc PR A 1
H22B H 1.5405 1.7387 0.3148 0.155 Uiso 0.523(10) 1 calc PR A 1
H22C H 1.4340 1.7048 0.2640 0.155 Uiso 0.523(10) 1 calc PR A 1
S1B S 1.5749(7) 1.5709(4) 0.2029(5) 0.065(3) Uani 0.477(10) 1 d PD A 2
C17B C 1.431(2) 1.529(2) 0.1942(18) 0.089(9) Uiso 0.477(10) 1 d PD A 2
H17C H 1.3799 1.5769 0.1836 0.107 Uiso 0.477(10) 1 calc PR A 2
H17D H 1.4290 1.4922 0.1452 0.107 Uiso 0.477(10) 1 calc PR A 2
C18B C 1.383(3) 1.4799(18) 0.2629(19) 0.070(7) Uiso 0.477(10) 1 d PD A 2
H18D H 1.3102 1.4558 0.2465 0.105 Uiso 0.477(10) 1 calc PR A 2
H18E H 1.3720 1.5173 0.3099 0.105 Uiso 0.477(10) 1 calc PR A 2
H18F H 1.4352 1.4343 0.2778 0.105 Uiso 0.477(10) 1 calc PR A 2
C19B C 1.6654(17) 1.4805(8) 0.2469(12) 0.126(7) Uani 0.477(10) 1 d PD A 2
H19C H 1.6412 1.4677 0.3034 0.151 Uiso 0.477(10) 1 calc PR A 2
H19D H 1.6555 1.4289 0.2135 0.151 Uiso 0.477(10) 1 calc PR A 2
C20B C 1.7967(13) 1.5094(8) 0.2461(14) 0.104(5) Uani 0.477(10) 1 d P A 2
H20D H 1.8438 1.4640 0.2686 0.155 Uiso 0.477(10) 1 calc PR A 2
H20E H 1.8058 1.5604 0.2794 0.155 Uiso 0.477(10) 1 calc PR A 2
H20F H 1.8202 1.5213 0.1899 0.155 Uiso 0.477(10) 1 calc PR A 2
C21B C 1.590(3) 1.6432(13) 0.2835(14) 0.087(6) Uani 0.477(10) 1 d PD A 2
H21C H 1.5640 1.6177 0.3355 0.105 Uiso 0.477(10) 1 calc PR A 2
H21D H 1.6702 1.6601 0.2897 0.105 Uiso 0.477(10) 1 calc PR A 2
C22B C 1.5128(10) 1.7239(9) 0.2603(15) 0.104(5) Uani 0.477(10) 1 d PD A 2
H22D H 1.5122 1.7638 0.3060 0.155 Uiso 0.477(10) 1 calc PR A 2
H22E H 1.4352 1.7052 0.2489 0.155 Uiso 0.477(10) 1 calc PR A 2
H22F H 1.5440 1.7516 0.2118 0.155 Uiso 0.477(10) 1 calc PR A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.514(15) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.425(11) . ?
C2 C2 1.48(2) 3_585 ?
C2 H2 0.9800 . ?
C3 C4 1.273(18) . ?
C3 O1 1.351(10) . ?
C3 C8 1.509(15) . ?
C4 F1 1.317(15) . ?
C4 C5 1.41(2) . ?
C5 C6 1.257(18) . ?
C5 F2 1.334(17) . ?
C6 C7 1.487(15) . ?
C6 I1 2.130(8) . ?
C7 C8 1.350(19) . ?
C7 F3 1.356(15) . ?
C8 F4 1.366(14) . ?
C9 C10 1.506(17) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O2 1.427(12) . ?
C10 C10 1.54(3) 3_575 ?
C10 H10 0.9800 . ?
C11 C16 1.233(19) . ?
C11 O2 1.366(10) . ?
C11 C12 1.502(17) . ?
C12 C13 1.36(2) . ?
C12 F5 1.383(16) . ?
C13 F6 1.362(15) . ?
C13 C14 1.519(18) . ?
C14 C15 1.25(2) . ?
C14 I2 2.076(10) . ?
C15 F7 1.349(17) . ?
C15 C16 1.41(2) . ?
C16 F8 1.349(18) . ?
S1A C21A 1.706(17) . ?
S1A C17A 1.82(4) . ?
S1A C19A 1.873(17) . ?
C17A C18A 1.45(3) . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C19A C20A 1.59(2) . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
C21A C22A 1.57(2) . ?
C21A H21A 0.9700 . ?
C21A H21B 0.9700 . ?
C22A H22A 0.9600 . ?
C22A H22B 0.9600 . ?
C22A H22C 0.9600 . ?
S1B C21B 1.722(19) . ?
S1B C17B 1.79(3) . ?
C17B C18B 1.45(3) . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?
C21B H21C 0.9700 . ?
C21B H21D 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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C2 112.0(12) . 3_585 ?
O1 C2 C1 107.8(9) . . ?
C2 C2 C1 113.6(8) 3_585 . ?
O1 C2 H2 107.7 . . ?
C2 C2 H2 107.7 3_585 . ?
C1 C2 H2 107.7 . . ?
C4 C3 O1 127.9(12) . . ?
C4 C3 C8 117.6(9) . . ?
O1 C3 C8 113.9(10) . . ?
C3 C4 F1 117.8(12) . . ?
C3 C4 C5 121.7(14) . . ?
F1 C4 C5 120.5(15) . . ?
C6 C5 F2 118.7(14) . . ?
C6 C5 C4 125.1(15) . . ?
F2 C5 C4 116.2(15) . . ?
C5 C6 C7 117.6(9) . . ?
C5 C6 I1 126.3(10) . . ?
C7 C6 I1 116.0(8) . . ?
C8 C7 F3 119.7(11) . . ?
C8 C7 C6 118.5(11) . . ?
F3 C7 C6 121.8(11) . . ?
C7 C8 F4 118.9(12) . . ?
C7 C8 C3 119.3(10) . . ?
F4 C8 C3 121.8(11) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 C9 107.6(9) . . ?
O2 C10 C10 108.8(13) . 3_575 ?
C9 C10 C10 114.3(9) . 3_575 ?
O2 C10 H10 108.7 . . ?
C9 C10 H10 108.7 . . ?
C10 C10 H10 108.7 3_575 . ?
C16 C11 O2 131.0(14) . . ?
C16 C11 C12 114.8(11) . . ?
O2 C11 C12 114.2(11) . . ?
C13 C12 F5 117.3(13) . . ?
C13 C12 C11 121.1(12) . . ?
F5 C12 C11 121.5(13) . . ?
C12 C13 F6 120.2(12) . . ?
C12 C13 C14 118.0(12) . . ?
F6 C13 C14 121.5(13) . . ?
C15 C14 C13 115.1(10) . . ?
C15 C14 I2 127.5(11) . . ?
C13 C14 I2 117.1(10) . . ?
C14 C15 F7 118.5(14) . . ?
C14 C15 C16 125.6(16) . . ?
F7 C15 C16 115.8(16) . . ?
C11 C16 F8 115.2(14) . . ?
C11 C16 C15 125.1(17) . . ?
F8 C16 C15 119.5(17) . . ?
C3 O1 C2 118.0(7) . . ?
C11 O2 C10 119.4(8) . . ?
C21A S1A C17A 115(2) . . ?
C21A S1A C19A 102.5(9) . . ?
C17A S1A C19A 95.4(18) . . ?
C18A C17A S1A 148(4) . . ?
C18A C17A H17A 99.9 . . ?
S1A C17A H17A 99.9 . . ?
C18A C17A H17B 99.9 . . ?
S1A C17A H17B 99.9 . . ?
H17A C17A H17B 104.1 . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C17A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C20A C19A S1A 110.2(11) . . ?
C20A C19A H19A 109.6 . . ?
S1A C19A H19A 109.6 . . ?
C20A C19A H19B 109.6 . . ?
S1A C19A H19B 109.6 . . ?
H19A C19A H19B 108.1 . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C22A C21A S1A 103.5(12) . . ?
C22A C21A H21A 111.1 . . ?
S1A C21A H21A 111.1 . . ?
C22A C21A H21B 111.1 . . ?
S1A C21A H21B 111.1 . . ?
H21A C21A H21B 109.0 . . ?
C21A C22A H22A 109.5 . . ?
C21A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C21A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C21B S1B C17B 113.0(16) . . ?
C18B C17B S1B 119(2) . . ?
C18B C17B H17C 107.5 . . ?
S1B C17B H17C 107.5 . . ?
C18B C17B H17D 107.5 . . ?
S1B C17B H17D 107.5 . . ?
H17C C17B H17D 107.0 . . ?
C17B C18B H18D 109.5 . . ?
C17B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C17B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
S1B C21B H21C 110.5 . . ?
S1B C21B H21D 110.5 . . ?
H21C C21B H21D 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 F1 -7.6(16) . . . . ?
C8 C3 C4 F1 -178.4(10) . . . . ?
O1 C3 C4 C5 173.6(10) . . . . ?
C8 C3 C4 C5 2.8(15) . . . . ?
C3 C4 C5 C6 -2(2) . . . . ?
F1 C4 C5 C6 179.6(12) . . . . ?
C3 C4 C5 F2 178.7(11) . . . . ?
F1 C4 C5 F2 -0.1(19) . . . . ?
F2 C5 C6 C7 178.5(13) . . . . ?
C4 C5 C6 C7 -1.2(17) . . . . ?
F2 C5 C6 I1 2.2(19) . . . . ?
C4 C5 C6 I1 -177.5(9) . . . . ?
C5 C6 C7 C8 2.6(14) . . . . ?
I1 C6 C7 C8 179.3(9) . . . . ?
C5 C6 C7 F3 -176.6(16) . . . . ?
I1 C6 C7 F3 0.1(16) . . . . ?
F3 C7 C8 F4 -1(2) . . . . ?
C6 C7 C8 F4 179.4(11) . . . . ?
F3 C7 C8 C3 177.8(11) . . . . ?
C6 C7 C8 C3 -1.4(17) . . . . ?
C4 C3 C8 C7 -1.2(14) . . . . ?
O1 C3 C8 C7 -173.3(10) . . . . ?
C4 C3 C8 F4 177.9(12) . . . . ?
O1 C3 C8 F4 5.8(14) . . . . ?
C16 C11 C12 C13 4.3(16) . . . . ?
O2 C11 C12 C13 -176.1(11) . . . . ?
C16 C11 C12 F5 -179.1(12) . . . . ?
O2 C11 C12 F5 0.5(14) . . . . ?
F5 C12 C13 F6 -3.1(19) . . . . ?
C11 C12 C13 F6 173.7(10) . . . . ?
F5 C12 C13 C14 -177.2(10) . . . . ?
C11 C12 C13 C14 -0.4(18) . . . . ?
C12 C13 C14 C15 -4.0(15) . . . . ?
F6 C13 C14 C15 -178.0(14) . . . . ?
C12 C13 C14 I2 -178.0(10) . . . . ?
F6 C13 C14 I2 8.0(15) . . . . ?
C13 C14 C15 F7 -178.0(13) . . . . ?
I2 C14 C15 F7 -5(2) . . . . ?
C13 C14 C15 C16 4.9(18) . . . . ?
I2 C14 C15 C16 178.2(10) . . . . ?
O2 C11 C16 F8 1.1(19) . . . . ?
C12 C11 C16 F8 -179.4(11) . . . . ?
O2 C11 C16 C15 176.6(11) . . . . ?
C12 C11 C16 C15 -3.9(18) . . . . ?
C14 C15 C16 C11 -1(2) . . . . ?
F7 C15 C16 C11 -178.0(13) . . . . ?
C14 C15 C16 F8 174.5(14) . . . . ?
F7 C15 C16 F8 -3(2) . . . . ?
C4 C3 O1 C2 76.5(14) . . . . ?
C8 C3 O1 C2 -112.3(12) . . . . ?
C2 C2 O1 C3 107.3(11) 3_585 . . . ?
C1 C2 O1 C3 -127.0(11) . . . . ?
C16 C11 O2 C10 58.2(18) . . . . ?
C12 C11 O2 C10 -121.3(13) . . . . ?
C9 C10 O2 C11 -128.2(13) . . . . ?
C10 C10 O2 C11 107.5(12) 3_575 . . . ?
C21A S1A C17A C18A 8(9) . . . . ?
C19A S1A C17A C18A -98(8) . . . . ?
C21A S1A C19A C20A 64.2(19) . . . . ?
C17A S1A C19A C20A -179(2) . . . . ?
C17A S1A C21A C22A 78(3) . . . . ?
C19A S1A C21A C22A -179.9(17) . . . . ?
C21B S1B C17B C18B -62(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.937
_refine_diff_density_min         -1.616
_refine_diff_density_rms         0.183
_database_code_depnum_ccdc_archive 'CCDC 1025197'
#######################################################################
#
#                 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_RR1-Et4NBr

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
6,6'-(((2R,3R)-butane-2,3-diyl)bis(oxy))
bis(1,2,4,5-tetrafluoro-3-iodobenzene),
tetraethylammonium bromide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H8 F8 I2 O2, C8 H20 N, Br'
_chemical_formula_sum            'C48 H56 Br2 F16 I4 N2 O4'
_chemical_formula_weight         1696.37
_chemical_absolute_configuration syn


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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   13.2765(2)
_cell_length_b                   15.9187(2)
_cell_length_c                   14.6917(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.437(8)
_cell_angle_gamma                90.00
_cell_volume                     3032.15(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13590
_cell_measurement_theta_min      3.5296
_cell_measurement_theta_max      27.4985

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    3.463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.273
_exptl_absorpt_correction_T_max  0.451

#----------------------------- Remark ------------------------------------#
# SADABS output:                                                          #
# Estimated minimum and maximum transmission:  0.6163  0.7456 #
# The ratio of these values is more reliable than their absolute values!  #
#-------------------------------------------------------------------------#

_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_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_method       CCD
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            58725
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         27.50
_reflns_number_total             13706
_reflns_number_gt                8986
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0089P)²+7.7632P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_number_reflns         13706
_refine_ls_number_parameters     685
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_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
Br1 Br 0.07535(5) 0.22850(13) 0.91894(4) 0.05483(16) Uani 1 1 d . . .
Br2 Br 0.43777(4) 0.72479(13) 0.59466(4) 0.05338(14) Uani 1 1 d . . .
I1 I 0.07594(8) 0.85998(4) 0.99966(7) 0.0628(3) Uani 1 1 d . . .
I2 I 0.07014(8) 1.59299(4) 0.99836(7) 0.0600(2) Uani 1 1 d . . .
F1 F 0.0172(9) 0.9627(7) 0.8104(7) 0.088(3) Uani 1 1 d . . .
F2 F 0.1162(8) 1.0715(6) 0.7232(7) 0.085(3) Uani 1 1 d . . .
F3 F 0.3110(8) 0.9333(6) 1.0545(8) 0.088(3) Uani 1 1 d . . .
F4 F 0.4102(8) 1.0484(6) 0.9687(9) 0.089(3) Uani 1 1 d . . .
F5 F 0.1209(9) 1.3830(6) 0.7267(7) 0.090(3) Uani 1 1 d . . .
F6 F 0.0142(8) 1.4916(7) 0.8053(8) 0.092(3) Uani 1 1 d . . .
F7 F 0.4067(9) 1.4131(6) 0.9740(10) 0.101(3) Uani 1 1 d . . .
F8 F 0.3003(9) 1.5185(6) 1.0572(8) 0.090(3) Uani 1 1 d . . .
O1 O 0.3220(9) 1.1169(6) 0.8055(9) 0.082(3) Uani 1 1 d . . .
O2 O 0.3196(10) 1.3456(6) 0.7972(8) 0.079(3) Uani 1 1 d . . .
C1 C 0.1578(14) 0.9472(8) 0.9342(11) 0.060(4) Uani 1 1 d . . .
C2 C 0.1139(13) 0.9850(9) 0.8524(12) 0.061(4) Uani 1 1 d . . .
C3 C 0.1686(14) 1.0390(9) 0.8093(12) 0.066(4) Uani 1 1 d . . .
C4 C 0.2670(14) 1.0630(8) 0.8476(13) 0.066(4) Uani 1 1 d . . .
C5 C 0.3133(13) 1.0271(9) 0.9320(13) 0.068(4) Uani 1 1 d . . .
C6 C 0.2610(12) 0.9692(9) 0.9716(10) 0.061(3) Uani 1 1 d . . .
C7 C 0.2816(8) 1.2009(4) 0.7760(6) 0.067(2) Uani 1 1 d . . .
H7 H 0.2125 1.2069 0.7890 0.080 Uiso 1 1 calc R . .
C8 C 0.2735(7) 1.2074(8) 0.6696(5) 0.084(4) Uani 1 1 d . . .
H8A H 0.2257 1.1660 0.6383 0.126 Uiso 1 1 calc R . .
H8B H 0.3401 1.1977 0.6560 0.126 Uiso 1 1 calc R . .
H8C H 0.2496 1.2624 0.6485 0.126 Uiso 1 1 calc R . .
C9 C 0.3523(8) 1.2622(6) 0.8339(7) 0.072(2) Uani 1 1 d . . .
H9 H 0.3456 1.2582 0.8989 0.086 Uiso 1 1 calc R . .
C10 C 0.4646(7) 1.2543(7) 0.8290(9) 0.112(4) Uani 1 1 d . . .
H10A H 0.5045 1.2954 0.8691 0.168 Uiso 1 1 calc R . .
H10B H 0.4716 1.2633 0.7661 0.168 Uiso 1 1 calc R . .
H10C H 0.4890 1.1991 0.8489 0.168 Uiso 1 1 calc R . .
C11 C 0.2648(14) 1.3918(8) 0.8464(11) 0.064(4) Uani 1 1 d . . .
C12 C 0.1629(13) 1.4142(9) 0.8074(11) 0.062(4) Uani 1 1 d . . .
C13 C 0.1120(14) 1.4738(9) 0.8499(12) 0.063(4) Uani 1 1 d . . .
C14 C 0.1551(12) 1.5080(8) 0.9372(11) 0.053(3) Uani 1 1 d . . .
C15 C 0.2519(14) 1.4857(8) 0.9774(12) 0.064(4) Uani 1 1 d . . .
C16 C 0.3079(13) 1.4298(9) 0.9315(13) 0.068(4) Uani 1 1 d . . .
I3 I 0.46065(8) 0.35458(4) 0.53252(7) 0.0597(2) Uani 1 1 d . . .
I4 I 0.46135(8) 1.09223(4) 0.52850(7) 0.0610(2) Uani 1 1 d . . .
F9 F 0.2321(8) 0.4287(7) 0.5201(8) 0.097(3) Uani 1 1 d . . .
F10 F 0.1556(8) 0.5453(6) 0.6183(9) 0.096(3) Uani 1 1 d . . .
F11 F 0.5605(8) 0.4551(6) 0.7196(8) 0.088(3) Uani 1 1 d . . .
F12 F 0.4818(8) 0.5653(6) 0.8229(7) 0.089(3) Uani 1 1 d . . .
F13 F 0.2351(10) 1.0117(8) 0.5097(8) 0.118(4) Uani 1 1 d . . .
F14 F 0.1601(10) 0.9018(8) 0.6146(10) 0.121(4) Uani 1 1 d . . .
F15 F 0.5553(8) 0.9956(8) 0.7180(9) 0.113(4) Uani 1 1 d . . .
F16 F 0.4782(9) 0.8863(7) 0.8236(8) 0.107(4) Uani 1 1 d . . .
O3 O 0.2742(9) 0.6112(6) 0.7780(9) 0.074(3) Uani 1 1 d . . .
O4 O 0.2748(10) 0.8408(6) 0.7781(8) 0.080(3) Uani 1 1 d . . .
C17 C 0.4001(12) 0.4421(7) 0.6152(10) 0.053(3) Uani 1 1 d . . .
C18 C 0.2921(14) 0.4643(9) 0.5923(13) 0.066(4) Uani 1 1 d . . .
C19 C 0.2567(12) 0.5253(9) 0.6472(13) 0.067(4) Uani 1 1 d . . .
C20 C 0.3177(13) 0.5608(8) 0.7249(10) 0.054(4) Uani 1 1 d . . .
C21 C 0.4225(12) 0.5336(8) 0.7485(11) 0.059(4) Uani 1 1 d . . .
C22 C 0.4594(13) 0.4770(9) 0.6912(12) 0.058(4) Uani 1 1 d . . .
C23 C 0.2400(7) 0.7567(5) 0.7466(6) 0.066(2) Uani 1 1 d . . .
H23 H 0.2409 0.7510 0.6804 0.079 Uiso 1 1 calc R . .
C24 C 0.1314(7) 0.7477(6) 0.7589(7) 0.088(3) Uani 1 1 d . . .
H24A H 0.0883 0.7885 0.7209 0.131 Uiso 1 1 calc R . .
H24B H 0.1295 0.7566 0.8231 0.131 Uiso 1 1 calc R . .
H24C H 0.1067 0.6922 0.7404 0.131 Uiso 1 1 calc R . .
C25 C 0.3160(7) 0.6946(5) 0.8026(6) 0.066(2) Uani 1 1 d . . .
H25 H 0.3823 0.6998 0.7840 0.079 Uiso 1 1 calc R . .
C26 C 0.3337(8) 0.7035(6) 0.9085(5) 0.086(3) Uani 1 1 d . . .
H26A H 0.3830 0.6623 0.9378 0.129 Uiso 1 1 calc R . .
H26B H 0.2698 0.6952 0.9277 0.129 Uiso 1 1 calc R . .
H26C H 0.3597 0.7587 0.9265 0.129 Uiso 1 1 calc R . .
C27 C 0.3173(14) 0.8911(8) 0.7182(12) 0.064(4) Uani 1 1 d . . .
C28 C 0.2591(13) 0.9258(10) 0.6379(12) 0.066(4) Uani 1 1 d . . .
C29 C 0.3037(12) 0.9791(10) 0.5899(11) 0.060(4) Uani 1 1 d . . .
C30 C 0.3974(13) 1.0065(8) 0.6096(11) 0.059(4) Uani 1 1 d . . .
C31 C 0.4574(13) 0.9737(10) 0.6919(12) 0.063(4) Uani 1 1 d . . .
C32 C 0.4147(14) 0.9166(9) 0.7419(11) 0.068(4) Uani 1 1 d . . .
N1 N 0.2395(4) 0.2263(11) 0.2239(3) 0.0635(13) Uani 1 1 d . . .
C33 C 0.2611(6) 0.222(2) 0.3298(5) 0.107(3) Uani 1 1 d . . .
H33A H 0.2985 0.1707 0.3497 0.128 Uiso 1 1 calc R . .
H33B H 0.3057 0.2687 0.3546 0.128 Uiso 1 1 calc R . .
C34 C 0.1676(7) 0.225(3) 0.3720(6) 0.147(6) Uani 1 1 d . . .
H34A H 0.1887 0.2210 0.4386 0.221 Uiso 1 1 calc R . .
H34B H 0.1230 0.1786 0.3489 0.221 Uiso 1 1 calc R . .
H34C H 0.1315 0.2768 0.3556 0.221 Uiso 1 1 calc R . .
C35 C 0.1772(12) 0.3005(11) 0.1830(12) 0.076(4) Uani 1 1 d . . .
H35A H 0.1096 0.2963 0.1977 0.092 Uiso 1 1 calc R . .
H35B H 0.1676 0.2977 0.1157 0.092 Uiso 1 1 calc R . .
C36 C 0.222(2) 0.3854(15) 0.215(3) 0.189(14) Uani 1 1 d . . .
H36A H 0.1764 0.4287 0.1849 0.283 Uiso 1 1 calc R . .
H36B H 0.2880 0.3915 0.1987 0.283 Uiso 1 1 calc R . .
H36C H 0.2302 0.3900 0.2812 0.283 Uiso 1 1 calc R . .
C37 C 0.1756(14) 0.1509(11) 0.1830(15) 0.100(6) Uani 1 1 d . . .
H37A H 0.1579 0.1566 0.1157 0.119 Uiso 1 1 calc R . .
H37B H 0.1118 0.1508 0.2051 0.119 Uiso 1 1 calc R . .
C38 C 0.230(2) 0.0662(14) 0.2078(18) 0.135(8) Uani 1 1 d . . .
H38A H 0.1869 0.0216 0.1779 0.202 Uiso 1 1 calc R . .
H38B H 0.2445 0.0583 0.2741 0.202 Uiso 1 1 calc R . .
H38C H 0.2941 0.0658 0.1867 0.202 Uiso 1 1 calc R . .
C39 C 0.3448(5) 0.2314(16) 0.1978(5) 0.078(3) Uani 1 1 d . . .
H39A H 0.3777 0.2835 0.2223 0.094 Uiso 1 1 calc R . .
H39B H 0.3872 0.1857 0.2284 0.094 Uiso 1 1 calc R . .
C40 C 0.3431(6) 0.228(2) 0.0956(5) 0.099(3) Uani 1 1 d . . .
H40A H 0.4125 0.2302 0.0863 0.148 Uiso 1 1 calc R . .
H40B H 0.3042 0.2741 0.0646 0.148 Uiso 1 1 calc R . .
H40C H 0.3117 0.1759 0.0703 0.148 Uiso 1 1 calc R . .
N2 N 0.8240(5) 0.2223(12) 0.6612(4) 0.084(2) Uani 1 1 d . . .
C41 C 0.778(2) 0.1509(14) 0.6062(19) 0.204(16) Uani 1 1 d . . .
H41A H 0.7828 0.1579 0.5418 0.245 Uiso 1 1 calc R . .
H41B H 0.7051 0.1468 0.6080 0.245 Uiso 1 1 calc R . .
C42 C 0.837(4) 0.0674(14) 0.649(2) 0.37(3) Uani 1 1 d . . .
H42A H 0.8036 0.0191 0.6166 0.551 Uiso 1 1 calc R . .
H42B H 0.8367 0.0634 0.7138 0.551 Uiso 1 1 calc R . .
H42C H 0.9073 0.0696 0.6411 0.551 Uiso 1 1 calc R . .
C43 C 0.8200(9) 0.232(2) 0.7645(7) 0.163(8) Uani 1 1 d . . .
H43A H 0.8374 0.2889 0.7846 0.196 Uiso 1 1 calc R . .
H43B H 0.8704 0.1945 0.8019 0.196 Uiso 1 1 calc R . .
C44 C 0.7094(9) 0.210(3) 0.7793(12) 0.264(18) Uani 1 1 d . . .
H44A H 0.7091 0.2123 0.8445 0.396 Uiso 1 1 calc R . .
H44B H 0.6911 0.1539 0.7566 0.396 Uiso 1 1 calc R . .
H44C H 0.6604 0.2491 0.7459 0.396 Uiso 1 1 calc R . .
C45 C 0.9304(9) 0.238(2) 0.6651(8) 0.205(12) Uani 1 1 d . . .
H45A H 0.9727 0.2031 0.7125 0.247 Uiso 1 1 calc R . .
H45B H 0.9465 0.2964 0.6805 0.247 Uiso 1 1 calc R . .
C46 C 0.9541(12) 0.215(4) 0.5580(9) 0.232(12) Uani 1 1 d . . .
H46A H 1.0266 0.2206 0.5600 0.348 Uiso 1 1 calc R . .
H46B H 0.9162 0.2529 0.5125 0.348 Uiso 1 1 calc R . .
H46C H 0.9329 0.1583 0.5414 0.348 Uiso 1 1 calc R . .
C47 C 0.753(2) 0.2960(13) 0.6222(17) 0.141(8) Uani 1 1 d . . .
H47A H 0.6862 0.2880 0.6379 0.169 Uiso 1 1 calc R . .
H47B H 0.7425 0.2966 0.5548 0.169 Uiso 1 1 calc R . .
C48 C 0.798(3) 0.3812(15) 0.661(2) 0.216(14) Uani 1 1 d . . .
H48A H 0.7522 0.4256 0.6345 0.324 Uiso 1 1 calc R . .
H48B H 0.8640 0.3894 0.6456 0.324 Uiso 1 1 calc R . .
H48C H 0.8063 0.3815 0.7277 0.324 Uiso 1 1 calc R . .


_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 2.118(14) . ?
I2 C14 2.084(14) . ?
F1 C2 1.35(2) . ?
F2 C3 1.406(19) . ?
F3 C6 1.380(17) . ?
F4 C5 1.328(19) . ?
F5 C12 1.295(18) . ?
F6 C13 1.35(2) . ?
F7 C16 1.35(2) . ?
F8 C15 1.317(19) . ?
O1 C4 1.358(17) . ?
O1 C7 1.471(12) . ?
O2 C11 1.350(17) . ?
O2 C9 1.462(13) . ?
C1 C2 1.36(2) . ?
C1 C6 1.41(2) . ?
C2 C3 1.37(2) . ?
C3 C4 1.36(3) . ?
C4 C5 1.38(2) . ?
C5 C6 1.36(2) . ?
C7 C9 1.488(11) . ?
C7 C8 1.547(11) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.514(13) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C16 1.40(2) . ?
C11 C12 1.40(2) . ?
C12 C13 1.39(2) . ?
C13 C14 1.40(2) . ?
C14 C15 1.34(2) . ?
C15 C16 1.42(2) . ?
I3 C17 2.117(14) . ?
I4 C30 2.107(13) . ?
F9 C18 1.31(2) . ?
F10 C19 1.356(19) . ?
F11 C22 1.362(19) . ?
F12 C21 1.303(17) . ?
F13 C29 1.423(19) . ?
F14 C28 1.34(2) . ?
F15 C31 1.32(2) . ?
F16 C32 1.396(18) . ?
O3 C20 1.336(16) . ?
O3 C25 1.454(12) . ?
O4 C27 1.395(17) . ?
O4 C23 1.458(12) . ?
C17 C22 1.34(2) . ?
C17 C18 1.45(2) . ?
C18 C19 1.41(2) . ?
C19 C20 1.37(2) . ?
C20 C21 1.43(2) . ?
C21 C22 1.39(2) . ?
C23 C24 1.498(11) . ?
C23 C25 1.521(11) . ?
C23 H23 0.9800 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.529(11) . ?
C25 H25 0.9800 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C32 1.33(2) . ?
C27 C28 1.38(2) . ?
C28 C29 1.32(2) . ?
C29 C30 1.29(2) . ?
C30 C31 1.40(2) . ?
C31 C32 1.37(2) . ?
N1 C35 1.49(2) . ?
N1 C37 1.52(2) . ?
N1 C33 1.521(9) . ?
N1 C39 1.530(8) . ?
C33 C34 1.502(11) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C36 1.51(3) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 C38 1.54(3) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.499(10) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
N2 C45 1.423(12) . ?
N2 C41 1.45(2) . ?
N2 C43 1.536(12) . ?
N2 C47 1.54(2) . ?
C41 C42 1.60(3) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 C44 1.57(2) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 C46 1.71(2) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C47 C48 1.54(3) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 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
C4 O1 C7 120.7(10) . . ?
C11 O2 C9 116.7(10) . . ?
C2 C1 C6 115.5(14) . . ?
C2 C1 I1 121.9(14) . . ?
C6 C1 I1 122.6(11) . . ?
F1 C2 C1 118.2(14) . . ?
F1 C2 C3 120.2(16) . . ?
C1 C2 C3 121.3(17) . . ?
C4 C3 C2 123.0(17) . . ?
C4 C3 F2 120.9(14) . . ?
C2 C3 F2 116.1(16) . . ?
O1 C4 C3 123.5(17) . . ?
O1 C4 C5 119.3(17) . . ?
C3 C4 C5 117.1(14) . . ?
F4 C5 C6 122.7(16) . . ?
F4 C5 C4 117.6(15) . . ?
C6 C5 C4 119.6(16) . . ?
C5 C6 F3 117.8(15) . . ?
C5 C6 C1 123.2(14) . . ?
F3 C6 C1 119.0(13) . . ?
O1 C7 C9 106.4(9) . . ?
O1 C7 C8 107.5(8) . . ?
C9 C7 C8 115.6(8) . . ?
O1 C7 H7 109.1 . . ?
C9 C7 H7 109.1 . . ?
C8 C7 H7 109.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C7 106.5(8) . . ?
O2 C9 C10 106.0(8) . . ?
C7 C9 C10 115.2(8) . . ?
O2 C9 H9 109.7 . . ?
C7 C9 H9 109.7 . . ?
C10 C9 H9 109.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 C16 123.5(17) . . ?
O2 C11 C12 120.4(15) . . ?
C16 C11 C12 115.5(14) . . ?
F5 C12 C13 121.3(17) . . ?
F5 C12 C11 117.7(14) . . ?
C13 C12 C11 120.8(16) . . ?
F6 C13 C12 115.7(16) . . ?
F6 C13 C14 121.6(13) . . ?
C12 C13 C14 122.5(17) . . ?
C15 C14 C13 117.7(14) . . ?
C15 C14 I2 122.5(12) . . ?
C13 C14 I2 119.8(12) . . ?
F8 C15 C14 121.6(14) . . ?
F8 C15 C16 117.8(16) . . ?
C14 C15 C16 120.4(16) . . ?
F7 C16 C11 119.9(15) . . ?
F7 C16 C15 117.3(17) . . ?
C11 C16 C15 122.8(16) . . ?
C20 O3 C25 120.3(9) . . ?
C27 O4 C23 118.1(10) . . ?
C22 C17 C18 117.9(14) . . ?
C22 C17 I3 121.6(12) . . ?
C18 C17 I3 120.5(10) . . ?
F9 C18 C19 122.9(16) . . ?
F9 C18 C17 118.9(14) . . ?
C19 C18 C17 118.2(15) . . ?
F10 C19 C20 122.1(14) . . ?
F10 C19 C18 114.4(16) . . ?
C20 C19 C18 123.5(15) . . ?
O3 C20 C19 118.8(14) . . ?
O3 C20 C21 124.2(14) . . ?
C19 C20 C21 116.6(12) . . ?
F12 C21 C22 122.0(14) . . ?
F12 C21 C20 117.9(13) . . ?
C22 C21 C20 120.1(14) . . ?
C17 C22 F11 120.8(14) . . ?
C17 C22 C21 123.5(15) . . ?
F11 C22 C21 115.7(14) . . ?
O4 C23 C24 107.4(8) . . ?
O4 C23 C25 107.3(8) . . ?
C24 C23 C25 114.6(8) . . ?
O4 C23 H23 109.2 . . ?
C24 C23 H23 109.2 . . ?
C25 C23 H23 109.2 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C25 C23 106.6(8) . . ?
O3 C25 C26 107.7(8) . . ?
C23 C25 C26 115.4(7) . . ?
O3 C25 H25 109.0 . . ?
C23 C25 H25 109.0 . . ?
C26 C25 H25 109.0 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 C27 C28 115.9(14) . . ?
C32 C27 O4 120.8(16) . . ?
C28 C27 O4 122.8(16) . . ?
C29 C28 F14 125.0(16) . . ?
C29 C28 C27 118.8(16) . . ?
F14 C28 C27 116.2(15) . . ?
C30 C29 C28 128.2(16) . . ?
C30 C29 F13 118.4(13) . . ?
C28 C29 F13 113.3(14) . . ?
C29 C30 C31 114.2(14) . . ?
C29 C30 I4 125.3(13) . . ?
C31 C30 I4 120.5(12) . . ?
F15 C31 C32 121.1(15) . . ?
F15 C31 C30 119.6(14) . . ?
C32 C31 C30 119.3(16) . . ?
C27 C32 C31 123.7(16) . . ?
C27 C32 F16 119.6(14) . . ?
C31 C32 F16 116.6(16) . . ?
C35 N1 C37 104.7(5) . . ?
C35 N1 C33 114.4(16) . . ?
C37 N1 C33 109.7(17) . . ?
C35 N1 C39 108.3(12) . . ?
C37 N1 C39 113.9(14) . . ?
C33 N1 C39 106.1(5) . . ?
C34 C33 N1 115.5(7) . . ?
C34 C33 H33A 108.4 . . ?
N1 C33 H33A 108.4 . . ?
C34 C33 H33B 108.4 . . ?
N1 C33 H33B 108.4 . . ?
H33A C33 H33B 107.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N1 C35 C36 115.9(15) . . ?
N1 C35 H35A 108.3 . . ?
C36 C35 H35A 108.3 . . ?
N1 C35 H35B 108.3 . . ?
C36 C35 H35B 108.3 . . ?
H35A C35 H35B 107.4 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N1 C37 C38 113.9(15) . . ?
N1 C37 H37A 108.8 . . ?
C38 C37 H37A 108.8 . . ?
N1 C37 H37B 108.8 . . ?
C38 C37 H37B 108.8 . . ?
H37A C37 H37B 107.7 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 N1 115.6(6) . . ?
C40 C39 H39A 108.4 . . ?
N1 C39 H39A 108.4 . . ?
C40 C39 H39B 108.4 . . ?
N1 C39 H39B 108.4 . . ?
H39A C39 H39B 107.4 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C45 N2 C41 117(2) . . ?
C45 N2 C43 100.9(9) . . ?
C41 N2 C43 121.6(19) . . ?
C45 N2 C47 114.0(19) . . ?
C41 N2 C47 103.6(8) . . ?
C43 N2 C47 98.4(15) . . ?
N2 C41 C42 108.4(17) . . ?
N2 C41 H41A 110.0 . . ?
C42 C41 H41A 110.0 . . ?
N2 C41 H41B 110.0 . . ?
C42 C41 H41B 110.0 . . ?
H41A C41 H41B 108.4 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
N2 C43 C44 110.4(12) . . ?
N2 C43 H43A 109.6 . . ?
C44 C43 H43A 109.6 . . ?
N2 C43 H43B 109.6 . . ?
C44 C43 H43B 109.6 . . ?
H43A C43 H43B 108.1 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N2 C45 C46 107.7(13) . . ?
N2 C45 H45A 110.2 . . ?
C46 C45 H45A 110.2 . . ?
N2 C45 H45B 110.2 . . ?
C46 C45 H45B 110.2 . . ?
H45A C45 H45B 108.5 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
N2 C47 C48 112(2) . . ?
N2 C47 H47A 109.2 . . ?
C48 C47 H47A 109.2 . . ?
N2 C47 H47B 109.2 . . ?
C48 C47 H47B 109.2 . . ?
H47A C47 H47B 107.9 . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F1 176.1(13) . . . . ?
I1 C1 C2 F1 -3.2(19) . . . . ?
C6 C1 C2 C3 2(2) . . . . ?
I1 C1 C2 C3 -177.8(11) . . . . ?
F1 C2 C3 C4 -179.1(14) . . . . ?
C1 C2 C3 C4 -5(2) . . . . ?
F1 C2 C3 F2 3(2) . . . . ?
C1 C2 C3 F2 177.5(13) . . . . ?
C7 O1 C4 C3 55.6(19) . . . . ?
C7 O1 C4 C5 -127.3(14) . . . . ?
C2 C3 C4 O1 -179.7(13) . . . . ?
F2 C3 C4 O1 -2(2) . . . . ?
C2 C3 C4 C5 3(2) . . . . ?
F2 C3 C4 C5 -179.2(13) . . . . ?
O1 C4 C5 F4 1(2) . . . . ?
C3 C4 C5 F4 178.3(14) . . . . ?
O1 C4 C5 C6 -176.0(13) . . . . ?
C3 C4 C5 C6 1(2) . . . . ?
F4 C5 C6 F3 2(2) . . . . ?
C4 C5 C6 F3 178.3(13) . . . . ?
F4 C5 C6 C1 178.8(14) . . . . ?
C4 C5 C6 C1 -4(2) . . . . ?
C2 C1 C6 C5 3(2) . . . . ?
I1 C1 C6 C5 -177.8(12) . . . . ?
C2 C1 C6 F3 -179.9(13) . . . . ?
I1 C1 C6 F3 -0.6(19) . . . . ?
C4 O1 C7 C9 114.7(14) . . . . ?
C4 O1 C7 C8 -120.9(14) . . . . ?
C11 O2 C9 C7 102.8(13) . . . . ?
C11 O2 C9 C10 -134.1(13) . . . . ?
O1 C7 C9 O2 173.4(6) . . . . ?
C8 C7 C9 O2 54.2(10) . . . . ?
O1 C7 C9 C10 56.3(10) . . . . ?
C8 C7 C9 C10 -63.0(10) . . . . ?
C9 O2 C11 C16 73.1(17) . . . . ?
C9 O2 C11 C12 -116.1(15) . . . . ?
O2 C11 C12 F5 6(2) . . . . ?
C16 C11 C12 F5 177.4(12) . . . . ?
O2 C11 C12 C13 -168.3(12) . . . . ?
C16 C11 C12 C13 3(2) . . . . ?
F5 C12 C13 F6 5(2) . . . . ?
C11 C12 C13 F6 178.9(13) . . . . ?
F5 C12 C13 C14 179.5(13) . . . . ?
C11 C12 C13 C14 -6(2) . . . . ?
F6 C13 C14 C15 178.7(13) . . . . ?
C12 C13 C14 C15 4(2) . . . . ?
F6 C13 C14 I2 -2.8(19) . . . . ?
C12 C13 C14 I2 -177.1(10) . . . . ?
C13 C14 C15 F8 176.3(13) . . . . ?
I2 C14 C15 F8 -2.2(19) . . . . ?
C13 C14 C15 C16 1(2) . . . . ?
I2 C14 C15 C16 -177.8(10) . . . . ?
O2 C11 C16 F7 -8(2) . . . . ?
C12 C11 C16 F7 -179.0(13) . . . . ?
O2 C11 C16 C15 172.9(13) . . . . ?
C12 C11 C16 C15 2(2) . . . . ?
F8 C15 C16 F7 1(2) . . . . ?
C14 C15 C16 F7 177.0(13) . . . . ?
F8 C15 C16 C11 -179.6(13) . . . . ?
C14 C15 C16 C11 -4(2) . . . . ?
C22 C17 C18 F9 -177.8(15) . . . . ?
I3 C17 C18 F9 1(2) . . . . ?
C22 C17 C18 C19 4(2) . . . . ?
I3 C17 C18 C19 -177.4(11) . . . . ?
F9 C18 C19 F10 -1(2) . . . . ?
C17 C18 C19 F10 177.0(13) . . . . ?
F9 C18 C19 C20 177.5(15) . . . . ?
C17 C18 C19 C20 -5(2) . . . . ?
C25 O3 C20 C19 -127.9(14) . . . . ?
C25 O3 C20 C21 59.0(19) . . . . ?
F10 C19 C20 O3 6(2) . . . . ?
C18 C19 C20 O3 -172.7(14) . . . . ?
F10 C19 C20 C21 179.3(13) . . . . ?
C18 C19 C20 C21 1(2) . . . . ?
O3 C20 C21 F12 -6(2) . . . . ?
C19 C20 C21 F12 -178.9(13) . . . . ?
O3 C20 C21 C22 176.3(13) . . . . ?
C19 C20 C21 C22 3(2) . . . . ?
C18 C17 C22 F11 176.2(13) . . . . ?
I3 C17 C22 F11 -2(2) . . . . ?
C18 C17 C22 C21 0(2) . . . . ?
I3 C17 C22 C21 -178.8(11) . . . . ?
F12 C21 C22 C17 178.6(14) . . . . ?
C20 C21 C22 C17 -3(2) . . . . ?
F12 C21 C22 F11 2(2) . . . . ?
C20 C21 C22 F11 179.9(12) . . . . ?
C27 O4 C23 C24 -128.2(12) . . . . ?
C27 O4 C23 C25 108.2(13) . . . . ?
C20 O3 C25 C23 107.6(13) . . . . ?
C20 O3 C25 C26 -127.9(13) . . . . ?
O4 C23 C25 O3 173.8(5) . . . . ?
C24 C23 C25 O3 54.8(10) . . . . ?
O4 C23 C25 C26 54.3(9) . . . . ?
C24 C23 C25 C26 -64.8(10) . . . . ?
C23 O4 C27 C32 -117.4(15) . . . . ?
C23 O4 C27 C28 71.2(17) . . . . ?
C32 C27 C28 C29 2(2) . . . . ?
O4 C27 C28 C29 173.6(14) . . . . ?
C32 C27 C28 F14 -178.5(14) . . . . ?
O4 C27 C28 F14 -7(2) . . . . ?
F14 C28 C29 C30 177.9(16) . . . . ?
C27 C28 C29 C30 -2(3) . . . . ?
F14 C28 C29 F13 1(2) . . . . ?
C27 C28 C29 F13 -178.8(14) . . . . ?
C28 C29 C30 C31 1(2) . . . . ?
F13 C29 C30 C31 177.1(14) . . . . ?
C28 C29 C30 I4 -179.7(13) . . . . ?
F13 C29 C30 I4 -3(2) . . . . ?
C29 C30 C31 F15 178.2(15) . . . . ?
I4 C30 C31 F15 -1(2) . . . . ?
C29 C30 C31 C32 1(2) . . . . ?
I4 C30 C31 C32 -178.4(11) . . . . ?
C28 C27 C32 C31 0(2) . . . . ?
O4 C27 C32 C31 -171.9(13) . . . . ?
C28 C27 C32 F16 178.3(13) . . . . ?
O4 C27 C32 F16 6(2) . . . . ?
F15 C31 C32 C27 -178.6(15) . . . . ?
C30 C31 C32 C27 -2(2) . . . . ?
F15 C31 C32 F16 3(2) . . . . ?
C30 C31 C32 F16 -179.9(13) . . . . ?
C35 N1 C33 C34 55(3) . . . . ?
C37 N1 C33 C34 -62(3) . . . . ?
C39 N1 C33 C34 175(3) . . . . ?
C37 N1 C35 C36 178(2) . . . . ?
C33 N1 C35 C36 58(2) . . . . ?
C39 N1 C35 C36 -60(2) . . . . ?
C35 N1 C37 C38 173.9(19) . . . . ?
C33 N1 C37 C38 -63(2) . . . . ?
C39 N1 C37 C38 56(2) . . . . ?
C35 N1 C39 C40 -63(2) . . . . ?
C37 N1 C39 C40 53(2) . . . . ?
C33 N1 C39 C40 174(2) . . . . ?
C45 N2 C41 C42 60(3) . . . . ?
C43 N2 C41 C42 -64(3) . . . . ?
C47 N2 C41 C42 -173(3) . . . . ?
C45 N2 C43 C44 -175(3) . . . . ?
C41 N2 C43 C44 -44(3) . . . . ?
C47 N2 C43 C44 68(3) . . . . ?
C41 N2 C45 C46 37(3) . . . . ?
C43 N2 C45 C46 171(3) . . . . ?
C47 N2 C45 C46 -85(3) . . . . ?
C45 N2 C47 C48 -43(3) . . . . ?
C41 N2 C47 C48 -171(3) . . . . ?
C43 N2 C47 C48 63(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.899
_refine_diff_density_min         -0.979
_refine_diff_density_rms         0.107
_database_code_depnum_ccdc_archive 'CCDC 1025198'
#######################################################################
#
#                 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_RR1-Bu4NBr

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
6,6'-(((2R,3R)-butane-2,3-diyl)bis(oxy))
bis(1,2,4,5-tetrafluoro-3-iodobenzene),
tetrabutylammonium bromide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H8 F8 I2 O2, C16 H36 N, Br'
_chemical_formula_sum            'C32 H44 Br F8 I2 N O2'
_chemical_formula_weight         960.39
_chemical_absolute_configuration syn


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'
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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   12.0074(10)
_cell_length_b                   15.2998(13)
_cell_length_c                   41.115(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7553.4(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.42

_exptl_crystal_description       prism
_exptl_crystal_colour            transparent
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3776
_exptl_absorpt_coefficient_mu    2.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.407
_exptl_absorpt_correction_T_max  0.622

#----------------------------- Remark ------------------------------------#
# SADABS output:                                                          #
# Estimated minimum and maximum transmission:  0.4759  0.7456             #
# The ratio of these values is more reliable than their absolute values!  #
#-------------------------------------------------------------------------#

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37334
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0784
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         0.99
_diffrn_reflns_theta_max         27.72
_reflns_number_total             17353
_reflns_number_gt                14397
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART, 2006'
_computing_cell_refinement       'Bruker SMART, 2006'
_computing_data_reduction        'Bruker SAINT, 2006'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0374P)²+97.8604P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(2)
_refine_ls_number_reflns         17353
_refine_ls_number_parameters     812
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0823
_refine_ls_wR_factor_ref         0.1856
_refine_ls_wR_factor_gt          0.1761
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.172
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.001

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 0.13467(10) 0.68920(8) 0.11631(3) 0.0292(3) Uani 1 1 d . . .
Br2 Br 0.42070(10) 0.17976(8) 0.11725(3) 0.0288(3) Uani 1 1 d . . .
I1 I 0.65538(7) -0.10064(6) -0.045678(19) 0.03216(19) Uani 1 1 d . . .
I2 I 0.81639(7) 0.16284(6) 0.308282(19) 0.03215(19) Uani 1 1 d . . .
F1 F 0.6400(7) 0.0949(5) -0.01497(17) 0.0401(18) Uani 1 1 d . . .
F2 F 0.6958(6) 0.1590(5) 0.04354(18) 0.0365(17) Uani 1 1 d . . .
F3 F 0.7388(7) -0.1885(5) 0.02054(19) 0.0418(19) Uani 1 1 d . . .
F4 F 0.7943(7) -0.1243(5) 0.07888(17) 0.0357(18) Uani 1 1 d . . .
F5 F 0.9522(7) 0.2090(6) 0.24331(19) 0.040(2) Uani 1 1 d . . .
F6 F 0.9321(6) 0.1586(5) 0.18154(17) 0.0350(17) Uani 1 1 d . . .
F7 F 0.6281(7) 0.0497(6) 0.27016(18) 0.048(2) Uani 1 1 d . . .
F8 F 0.6089(7) -0.0035(6) 0.20919(19) 0.046(2) Uani 1 1 d . . .
O1 O 0.7780(7) 0.0484(6) 0.09243(19) 0.0288(19) Uani 1 1 d . . .
O2 O 0.7706(7) 0.0461(6) 0.1620(2) 0.031(2) Uani 1 1 d . . .
C1 C 0.6856(11) -0.0481(10) 0.0008(3) 0.031(3) Uani 1 1 d . . .
C2 C 0.6773(10) 0.0374(8) 0.0079(3) 0.026(3) Uani 1 1 d . . .
C3 C 0.7040(9) 0.0741(7) 0.0385(3) 0.020(2) Uani 1 1 d . . .
C4 C 0.7431(10) 0.0200(8) 0.0634(3) 0.022(2) Uani 1 1 d . . .
C5 C 0.7553(10) -0.0668(8) 0.0559(3) 0.028(3) Uani 1 1 d . . .
C6 C 0.7259(11) -0.0996(7) 0.0257(3) 0.029(3) Uani 1 1 d . . .
C7 C 0.6972(9) 0.1000(8) 0.1118(3) 0.026(2) Uani 1 1 d . . .
H7 H 0.6284 0.1058 0.0992 0.032 Uiso 1 1 calc R . .
C8 C 0.7433(13) 0.1907(9) 0.1181(3) 0.043(3) Uani 1 1 d . . .
H8A H 0.7582 0.2190 0.0977 0.065 Uiso 1 1 calc R . .
H8B H 0.8110 0.1862 0.1304 0.065 Uiso 1 1 calc R . .
H8C H 0.6897 0.2242 0.1301 0.065 Uiso 1 1 calc R . .
C9 C 0.6711(10) 0.0483(9) 0.1427(3) 0.032(3) Uani 1 1 d . . .
H9 H 0.6124 0.0785 0.1548 0.038 Uiso 1 1 calc R . .
C10 C 0.6326(13) -0.0479(10) 0.1354(3) 0.045(4) Uani 1 1 d . . .
H10A H 0.6167 -0.0774 0.1555 0.067 Uiso 1 1 calc R . .
H10B H 0.6908 -0.0784 0.1241 0.067 Uiso 1 1 calc R . .
H10C H 0.5668 -0.0468 0.1221 0.067 Uiso 1 1 calc R . .
C11 C 0.7692(9) 0.0770(8) 0.1936(3) 0.028(3) Uani 1 1 d . . .
C12 C 0.6936(10) 0.0525(9) 0.2169(3) 0.031(3) Uani 1 1 d . . .
C13 C 0.7056(9) 0.0806(9) 0.2488(3) 0.027(3) Uani 1 1 d . . .
C14 C 0.7912(10) 0.1307(7) 0.2588(3) 0.025(3) Uani 1 1 d . . .
C15 C 0.8677(8) 0.1571(6) 0.2355(2) 0.0148(19) Uani 1 1 d . . .
C16 C 0.8563(10) 0.1307(8) 0.2028(3) 0.026(2) Uani 1 1 d . . .
I3 I 0.89166(7) 0.40315(6) -0.04435(2) 0.0355(2) Uani 1 1 d . . .
I4 I 0.63775(8) 0.67836(6) 0.30601(2) 0.0372(2) Uani 1 1 d . . .
F9 F 0.8971(7) 0.5978(5) -0.01373(17) 0.044(2) Uani 1 1 d . . .
F10 F 0.8480(7) 0.6599(5) 0.04618(19) 0.0412(18) Uani 1 1 d . . .
F11 F 0.8253(9) 0.3108(6) 0.0223(2) 0.058(3) Uani 1 1 d . . .
F12 F 0.7760(8) 0.3728(5) 0.0818(2) 0.047(2) Uani 1 1 d . . .
F13 F 0.8545(7) 0.5938(7) 0.27169(19) 0.053(2) Uani 1 1 d . . .
F14 F 0.9000(8) 0.5555(7) 0.2099(2) 0.055(2) Uani 1 1 d . . .
F15 F 0.5149(9) 0.7237(9) 0.2385(2) 0.076(4) Uani 1 1 d . . .
F16 F 0.5636(7) 0.6852(8) 0.17610(19) 0.058(3) Uani 1 1 d . . .
O3 O 0.7812(6) 0.5486(5) 0.09594(19) 0.0232(17) Uani 1 1 d . . .
O4 O 0.7486(7) 0.5921(7) 0.1600(2) 0.038(2) Uani 1 1 d . . .
C17 C 0.8611(10) 0.4505(7) 0.0028(3) 0.023(2) Uani 1 1 d . . .
C18 C 0.8683(11) 0.5408(9) 0.0096(3) 0.030(3) Uani 1 1 d . . .
C19 C 0.8402(12) 0.5722(7) 0.0402(3) 0.028(3) Uani 1 1 d . . .
C20 C 0.8104(10) 0.5174(8) 0.0655(3) 0.027(3) Uani 1 1 d . . .
C21 C 0.8061(11) 0.4297(9) 0.0589(3) 0.033(3) Uani 1 1 d . . .
C22 C 0.8293(9) 0.3951(8) 0.0277(3) 0.025(2) Uani 1 1 d . . .
C23 C 0.8789(9) 0.5672(8) 0.1168(3) 0.026(3) Uani 1 1 d . . .
H23 H 0.9374 0.5935 0.1034 0.031 Uiso 1 1 calc R . .
C24 C 0.9235(15) 0.4842(12) 0.1316(4) 0.059(5) Uani 1 1 d . . .
H24A H 0.9472 0.4453 0.1146 0.088 Uiso 1 1 calc R . .
H24B H 0.8661 0.4566 0.1442 0.088 Uiso 1 1 calc R . .
H24C H 0.9857 0.4977 0.1454 0.088 Uiso 1 1 calc R . .
C25 C 0.8404(9) 0.6338(7) 0.1413(3) 0.023(2) Uani 1 1 d . . .
H25 H 0.9019 0.6467 0.1562 0.028 Uiso 1 1 calc R . .
C26 C 0.7999(13) 0.7168(9) 0.1270(4) 0.043(4) Uani 1 1 d . . .
H26A H 0.7763 0.7554 0.1441 0.064 Uiso 1 1 calc R . .
H26B H 0.7382 0.7050 0.1128 0.064 Uiso 1 1 calc R . .
H26C H 0.8588 0.7438 0.1149 0.064 Uiso 1 1 calc R . .
C27 C 0.7348(9) 0.6208(8) 0.1913(3) 0.030(3) Uani 1 1 d . . .
C28 C 0.8052(11) 0.6002(11) 0.2167(3) 0.043(3) Uani 1 1 d . . .
C29 C 0.7829(10) 0.6185(11) 0.2485(3) 0.037(3) Uani 1 1 d . . .
C30 C 0.6840(11) 0.6613(9) 0.2568(3) 0.031(3) Uani 1 1 d . . .
C31 C 0.6114(11) 0.6871(11) 0.2319(3) 0.041(3) Uani 1 1 d . . .
C32 C 0.6369(10) 0.6642(10) 0.2003(3) 0.035(3) Uani 1 1 d . . .
N1 N 0.1124(10) 0.9696(7) 0.1236(3) 0.034(3) Uani 1 1 d . . .
C33 C 0.1515(9) 0.9287(8) 0.0913(2) 0.022(2) Uani 1 1 d . . .
H33A H 0.1897 0.8743 0.0960 0.027 Uiso 1 1 calc R . .
H33B H 0.2047 0.9678 0.0811 0.027 Uiso 1 1 calc R . .
C34 C 0.0554(11) 0.9104(9) 0.0671(3) 0.032(3) Uani 1 1 d . . .
H34A H 0.0093 0.9620 0.0644 0.038 Uiso 1 1 calc R . .
H34B H 0.0092 0.8628 0.0748 0.038 Uiso 1 1 calc R . .
C35 C 0.1137(11) 0.8854(9) 0.0342(3) 0.034(3) Uani 1 1 d . . .
H35A H 0.1537 0.9357 0.0258 0.040 Uiso 1 1 calc R . .
H35B H 0.1672 0.8391 0.0380 0.040 Uiso 1 1 calc R . .
C36 C 0.0279(16) 0.8552(15) 0.0091(4) 0.069(6) Uani 1 1 d . . .
H36A H 0.0650 0.8409 -0.0109 0.104 Uiso 1 1 calc R . .
H36B H -0.0249 0.9012 0.0053 0.104 Uiso 1 1 calc R . .
H36C H -0.0103 0.8045 0.0172 0.104 Uiso 1 1 calc R . .
C37 C 0.0543(8) 1.0615(7) 0.1178(3) 0.020(2) Uani 1 1 d . . .
H37A H -0.0192 1.0511 0.1087 0.024 Uiso 1 1 calc R . .
H37B H 0.0441 1.0894 0.1387 0.024 Uiso 1 1 calc R . .
C38 C 0.1136(10) 1.1233(8) 0.0961(3) 0.026(2) Uani 1 1 d . . .
H38A H 0.1220 1.0978 0.0747 0.031 Uiso 1 1 calc R . .
H38B H 0.1872 1.1352 0.1048 0.031 Uiso 1 1 calc R . .
C39 C 0.0462(10) 1.2091(8) 0.0938(3) 0.030(3) Uani 1 1 d . . .
H39A H -0.0270 1.1968 0.0850 0.036 Uiso 1 1 calc R . .
H39B H 0.0364 1.2334 0.1154 0.036 Uiso 1 1 calc R . .
C40 C 0.1049(12) 1.2755(8) 0.0724(3) 0.035(3) Uani 1 1 d . . .
H40A H 0.0614 1.3280 0.0713 0.052 Uiso 1 1 calc R . .
H40B H 0.1137 1.2518 0.0509 0.052 Uiso 1 1 calc R . .
H40C H 0.1768 1.2885 0.0814 0.052 Uiso 1 1 calc R . .
C41 C 0.2196(10) 0.9839(9) 0.1438(3) 0.028(3) Uani 1 1 d . . .
H41A H 0.2659 1.0257 0.1323 0.034 Uiso 1 1 calc R . .
H41B H 0.1983 1.0107 0.1643 0.034 Uiso 1 1 calc R . .
C42 C 0.2898(11) 0.9051(9) 0.1513(3) 0.032(3) Uani 1 1 d . . .
H42A H 0.3307 0.8886 0.1319 0.039 Uiso 1 1 calc R . .
H42B H 0.2411 0.8568 0.1569 0.039 Uiso 1 1 calc R . .
C43 C 0.3710(17) 0.9189(14) 0.1786(4) 0.071(4) Uani 1 1 d . . .
H43A H 0.4276 0.8738 0.1772 0.085 Uiso 1 1 calc R . .
H43B H 0.4078 0.9746 0.1751 0.085 Uiso 1 1 calc R . .
C44 C 0.3271(17) 0.9185(14) 0.2112(4) 0.071(4) Uani 1 1 d . . .
H44A H 0.3864 0.9291 0.2264 0.107 Uiso 1 1 calc R . .
H44B H 0.2940 0.8627 0.2157 0.107 Uiso 1 1 calc R . .
H44C H 0.2718 0.9635 0.2133 0.107 Uiso 1 1 calc R . .
C45 C 0.0318(10) 0.9063(7) 0.1405(3) 0.025(2) Uani 1 1 d . . .
H45A H -0.0390 0.9078 0.1292 0.029 Uiso 1 1 calc R . .
H45B H 0.0612 0.8475 0.1386 0.029 Uiso 1 1 calc R . .
C46 C 0.0113(9) 0.9253(8) 0.1764(3) 0.026(2) Uani 1 1 d . . .
H46A H 0.0795 0.9166 0.1886 0.031 Uiso 1 1 calc R . .
H46B H -0.0119 0.9856 0.1791 0.031 Uiso 1 1 calc R . .
C47 C -0.0786(10) 0.8648(8) 0.1891(3) 0.029(3) Uani 1 1 d . . .
H47A H -0.0585 0.8047 0.1844 0.035 Uiso 1 1 calc R . .
H47B H -0.1483 0.8773 0.1782 0.035 Uiso 1 1 calc R . .
C48 C -0.0937(13) 0.8762(11) 0.2261(3) 0.047(4) Uani 1 1 d . . .
H48A H -0.1508 0.8373 0.2337 0.071 Uiso 1 1 calc R . .
H48B H -0.1147 0.9355 0.2307 0.071 Uiso 1 1 calc R . .
H48C H -0.0249 0.8630 0.2370 0.071 Uiso 1 1 calc R . .
N2 N 0.4476(8) 0.4740(7) 0.1185(3) 0.029(2) Uani 1 1 d . . .
C49 C 0.5119(15) 0.4350(12) 0.0887(4) 0.054(4) Uani 1 1 d . . .
H49A H 0.5771 0.4711 0.0851 0.064 Uiso 1 1 calc R . .
H49B H 0.5384 0.3775 0.0950 0.064 Uiso 1 1 calc R . .
C50 C 0.4560(14) 0.4258(10) 0.0579(4) 0.047(4) Uani 1 1 d . . .
H50A H 0.4223 0.4816 0.0526 0.056 Uiso 1 1 calc R . .
H50B H 0.3960 0.3841 0.0607 0.056 Uiso 1 1 calc R . .
C51 C 0.522(2) 0.3980(15) 0.0300(4) 0.093(9) Uani 1 1 d . . .
H51A H 0.5788 0.4427 0.0269 0.112 Uiso 1 1 calc R . .
H51B H 0.5616 0.3457 0.0368 0.112 Uiso 1 1 calc R . .
C52 C 0.4786(19) 0.3795(17) -0.0017(4) 0.093(8) Uani 1 1 d . . .
H52A H 0.5385 0.3638 -0.0160 0.140 Uiso 1 1 calc R . .
H52B H 0.4414 0.4304 -0.0100 0.140 Uiso 1 1 calc R . .
H52C H 0.4267 0.3320 -0.0003 0.140 Uiso 1 1 calc R . .
C53 C 0.4109(17) 0.5677(11) 0.1102(4) 0.058(5) Uani 1 1 d . . .
H53A H 0.3481 0.5629 0.0955 0.070 Uiso 1 1 calc R . .
H53B H 0.3826 0.5932 0.1302 0.070 Uiso 1 1 calc R . .
C54 C 0.4868(17) 0.6308(13) 0.0962(4) 0.064(5) Uani 1 1 d . . .
H54A H 0.5551 0.6296 0.1087 0.077 Uiso 1 1 calc R . .
H54B H 0.5050 0.6113 0.0744 0.077 Uiso 1 1 calc R . .
C55 C 0.4511(17) 0.7187(13) 0.0942(5) 0.065(5) Uiso 1 1 d . . .
H55A H 0.4437 0.7393 0.1164 0.079 Uiso 1 1 calc R . .
H55B H 0.3764 0.7173 0.0851 0.079 Uiso 1 1 calc R . .
C56 C 0.509(2) 0.7848(10) 0.0770(5) 0.086(8) Uani 1 1 d . . .
H56A H 0.4701 0.8392 0.0789 0.129 Uiso 1 1 calc R . .
H56B H 0.5149 0.7689 0.0545 0.129 Uiso 1 1 calc R . .
H56C H 0.5828 0.7911 0.0860 0.129 Uiso 1 1 calc R . .
C57 C 0.5223(14) 0.4751(12) 0.1469(4) 0.055(4) Uani 1 1 d . . .
H57A H 0.5827 0.5151 0.1421 0.067 Uiso 1 1 calc R . .
H57B H 0.4810 0.4998 0.1650 0.067 Uiso 1 1 calc R . .
C58 C 0.5724(15) 0.3926(12) 0.1583(5) 0.061(5) Uani 1 1 d . . .
H58A H 0.6295 0.3755 0.1429 0.073 Uiso 1 1 calc R . .
H58B H 0.5153 0.3477 0.1579 0.073 Uiso 1 1 calc R . .
C59 C 0.6227(15) 0.3938(11) 0.1912(4) 0.058(4) Uani 1 1 d . . .
H59A H 0.6708 0.4447 0.1923 0.069 Uiso 1 1 calc R . .
H59B H 0.5627 0.4036 0.2066 0.069 Uiso 1 1 calc R . .
C60 C 0.6839(18) 0.3232(17) 0.2026(5) 0.105(9) Uani 1 1 d . . .
H60A H 0.7106 0.3356 0.2241 0.158 Uiso 1 1 calc R . .
H60B H 0.7461 0.3130 0.1884 0.158 Uiso 1 1 calc R . .
H60C H 0.6375 0.2721 0.2032 0.158 Uiso 1 1 calc R . .
C61 C 0.3508(13) 0.4147(10) 0.1229(4) 0.048(4) Uani 1 1 d . . .
H61A H 0.3781 0.3550 0.1219 0.057 Uiso 1 1 calc R . .
H61B H 0.3012 0.4229 0.1045 0.057 Uiso 1 1 calc R . .
C62 C 0.2824(13) 0.4238(12) 0.1538(4) 0.049(4) Uani 1 1 d . . .
H62A H 0.3297 0.4101 0.1722 0.058 Uiso 1 1 calc R . .
H62B H 0.2595 0.4843 0.1559 0.058 Uiso 1 1 calc R . .
C63 C 0.1833(15) 0.3686(12) 0.1553(4) 0.061(4) Uani 1 1 d . . .
H63A H 0.2067 0.3097 0.1499 0.073 Uiso 1 1 calc R . .
H63B H 0.1339 0.3878 0.1381 0.073 Uiso 1 1 calc R . .
C64 C 0.1132(14) 0.3621(11) 0.1863(4) 0.061(4) Uani 1 1 d . . .
H64A H 0.0527 0.3221 0.1828 0.092 Uiso 1 1 calc R . .
H64B H 0.0840 0.4187 0.1917 0.092 Uiso 1 1 calc R . .
H64C H 0.1588 0.3413 0.2039 0.092 Uiso 1 1 calc R . .


_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(11) . ?
I2 C14 2.115(12) . ?
F1 C2 1.362(14) . ?
F2 C3 1.319(13) . ?
F3 C6 1.385(13) . ?
F4 C5 1.374(13) . ?
F5 C15 1.328(12) . ?
F6 C16 1.332(13) . ?
F7 C13 1.364(13) . ?
F8 C12 1.367(14) . ?
O1 C4 1.337(13) . ?
O1 C7 1.482(13) . ?
O2 C11 1.380(14) . ?
O2 C9 1.435(14) . ?
C1 C2 1.343(19) . ?
C1 C6 1.380(17) . ?
C2 C3 1.414(15) . ?
C3 C4 1.399(15) . ?
C4 C5 1.372(17) . ?
C5 C6 1.382(17) . ?
C7 C8 1.516(18) . ?
C7 C9 1.527(17) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.57(2) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.373(16) . ?
C11 C16 1.384(17) . ?
C12 C13 1.387(17) . ?
C13 C14 1.348(17) . ?
C14 C15 1.385(16) . ?
C15 C16 1.411(15) . ?
I3 C17 2.104(11) . ?
I4 C30 2.116(11) . ?
F9 C18 1.340(13) . ?
F10 C19 1.367(13) . ?
F11 C22 1.309(14) . ?
F12 C21 1.332(15) . ?
F13 C29 1.338(14) . ?
F14 C28 1.356(16) . ?
F15 C31 1.314(16) . ?
F16 C32 1.365(14) . ?
O3 C20 1.386(14) . ?
O3 C23 1.482(13) . ?
O4 C27 1.370(14) . ?
O4 C25 1.488(14) . ?
C17 C22 1.381(16) . ?
C17 C18 1.411(16) . ?
C18 C19 1.392(16) . ?
C19 C20 1.381(16) . ?
C20 C21 1.369(18) . ?
C21 C22 1.415(17) . ?
C23 C25 1.505(15) . ?
C23 C24 1.507(19) . ?
C23 H23 0.9800 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.482(16) . ?
C25 H25 0.9800 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.381(18) . ?
C27 C32 1.399(17) . ?
C28 C29 1.365(18) . ?
C29 C30 1.398(19) . ?
C30 C31 1.400(19) . ?
C31 C32 1.382(17) . ?
N1 C45 1.537(16) . ?
N1 C33 1.539(14) . ?
N1 C41 1.549(16) . ?
N1 C37 1.587(14) . ?
C33 C34 1.550(15) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.570(17) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.53(2) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 C38 1.480(15) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.546(17) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.518(16) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 C42 1.504(18) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.50(2) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 C44 1.44(2) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 C46 1.523(15) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 C47 1.515(15) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C47 C48 1.540(17) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
N2 C57 1.475(18) . ?
N2 C61 1.486(19) . ?
N2 C53 1.54(2) . ?
N2 C49 1.565(17) . ?
C49 C50 1.44(2) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 C51 1.46(2) . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C51 C52 1.43(3) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 C54 1.45(2) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C54 C55 1.41(2) . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?
C55 C56 1.42(3) . ?
C55 H55A 0.9700 . ?
C55 H55B 0.9700 . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
C57 C58 1.47(2) . ?
C57 H57A 0.9700 . ?
C57 H57B 0.9700 . ?
C58 C59 1.48(2) . ?
C58 H58A 0.9700 . ?
C58 H58B 0.9700 . ?
C59 C60 1.39(2) . ?
C59 H59A 0.9700 . ?
C59 H59B 0.9700 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
C61 C62 1.518(19) . ?
C61 H61A 0.9700 . ?
C61 H61B 0.9700 . ?
C62 C63 1.46(2) . ?
C62 H62A 0.9700 . ?
C62 H62B 0.9700 . ?
C63 C64 1.53(2) . ?
C63 H63A 0.9700 . ?
C63 H63B 0.9700 . ?
C64 H64A 0.9600 . ?
C64 H64B 0.9600 . ?
C64 H64C 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
C4 O1 C7 116.6(9) . . ?
C11 O2 C9 120.1(9) . . ?
C2 C1 C6 115.0(11) . . ?
C2 C1 I1 123.7(9) . . ?
C6 C1 I1 121.1(10) . . ?
C1 C2 F1 120.3(10) . . ?
C1 C2 C3 124.1(11) . . ?
F1 C2 C3 115.6(11) . . ?
F2 C3 C4 119.4(10) . . ?
F2 C3 C2 120.9(10) . . ?
C4 C3 C2 119.6(10) . . ?
O1 C4 C5 118.9(10) . . ?
O1 C4 C3 124.6(11) . . ?
C5 C4 C3 116.2(10) . . ?
C4 C5 F4 120.0(11) . . ?
C4 C5 C6 121.8(11) . . ?
F4 C5 C6 118.1(11) . . ?
C1 C6 C5 123.1(11) . . ?
C1 C6 F3 119.0(11) . . ?
C5 C6 F3 117.8(10) . . ?
O1 C7 C8 109.9(10) . . ?
O1 C7 C9 107.8(9) . . ?
C8 C7 C9 114.0(10) . . ?
O1 C7 H7 108.3 . . ?
C8 C7 H7 108.3 . . ?
C9 C7 H7 108.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C7 107.5(10) . . ?
O2 C9 C10 109.1(11) . . ?
C7 C9 C10 112.7(10) . . ?
O2 C9 H9 109.1 . . ?
C7 C9 H9 109.1 . . ?
C10 C9 H9 109.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.0(11) . . ?
C12 C11 O2 124.8(11) . . ?
C16 C11 O2 116.9(10) . . ?
F8 C12 C11 120.0(11) . . ?
F8 C12 C13 119.4(11) . . ?
C11 C12 C13 120.5(11) . . ?
C14 C13 F7 121.4(11) . . ?
C14 C13 C12 123.0(11) . . ?
F7 C13 C12 115.6(11) . . ?
C13 C14 C15 117.5(11) . . ?
C13 C14 I2 122.3(9) . . ?
C15 C14 I2 120.1(8) . . ?
F5 C15 C14 121.0(9) . . ?
F5 C15 C16 118.3(9) . . ?
C14 C15 C16 120.7(10) . . ?
F6 C16 C11 121.7(10) . . ?
F6 C16 C15 117.9(10) . . ?
C11 C16 C15 120.3(10) . . ?
C20 O3 C23 113.0(9) . . ?
C27 O4 C25 115.8(9) . . ?
C22 C17 C18 118.2(11) . . ?
C22 C17 I3 121.3(8) . . ?
C18 C17 I3 120.4(8) . . ?
F9 C18 C19 119.0(11) . . ?
F9 C18 C17 120.9(11) . . ?
C19 C18 C17 120.0(11) . . ?
F10 C19 C20 118.7(10) . . ?
F10 C19 C18 119.0(11) . . ?
C20 C19 C18 122.3(10) . . ?
C21 C20 C19 117.1(11) . . ?
C21 C20 O3 120.5(11) . . ?
C19 C20 O3 122.3(11) . . ?
F12 C21 C20 120.7(12) . . ?
F12 C21 C22 116.7(12) . . ?
C20 C21 C22 122.6(12) . . ?
F11 C22 C17 119.3(11) . . ?
F11 C22 C21 121.0(11) . . ?
C17 C22 C21 119.7(11) . . ?
O3 C23 C25 105.9(9) . . ?
O3 C23 C24 110.7(11) . . ?
C25 C23 C24 114.2(11) . . ?
O3 C23 H23 108.6 . . ?
C25 C23 H23 108.6 . . ?
C24 C23 H23 108.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 O4 109.2(10) . . ?
C26 C25 C23 114.6(11) . . ?
O4 C25 C23 106.4(9) . . ?
C26 C25 H25 108.8 . . ?
O4 C25 H25 108.8 . . ?
C23 C25 H25 108.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O4 C27 C28 124.3(11) . . ?
O4 C27 C32 120.1(11) . . ?
C28 C27 C32 115.0(11) . . ?
F14 C28 C29 117.7(13) . . ?
F14 C28 C27 118.3(11) . . ?
C29 C28 C27 123.9(13) . . ?
F13 C29 C28 119.9(13) . . ?
F13 C29 C30 120.4(12) . . ?
C28 C29 C30 119.7(12) . . ?
C29 C30 C31 119.0(11) . . ?
C29 C30 I4 120.8(9) . . ?
C31 C30 I4 120.0(9) . . ?
F15 C31 C32 119.8(13) . . ?
F15 C31 C30 121.3(12) . . ?
C32 C31 C30 118.5(13) . . ?
F16 C32 C31 118.8(12) . . ?
F16 C32 C27 117.4(11) . . ?
C31 C32 C27 123.7(12) . . ?
C45 N1 C33 109.1(9) . . ?
C45 N1 C41 111.6(9) . . ?
C33 N1 C41 105.4(9) . . ?
C45 N1 C37 110.5(8) . . ?
C33 N1 C37 111.4(9) . . ?
C41 N1 C37 108.7(9) . . ?
N1 C33 C34 113.5(9) . . ?
N1 C33 H33A 108.9 . . ?
C34 C33 H33A 108.9 . . ?
N1 C33 H33B 108.9 . . ?
C34 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
C33 C34 C35 105.4(10) . . ?
C33 C34 H34A 110.7 . . ?
C35 C34 H34A 110.7 . . ?
C33 C34 H34B 110.7 . . ?
C35 C34 H34B 110.7 . . ?
H34A C34 H34B 108.8 . . ?
C36 C35 C34 110.7(11) . . ?
C36 C35 H35A 109.5 . . ?
C34 C35 H35A 109.5 . . ?
C36 C35 H35B 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 N1 116.4(9) . . ?
C38 C37 H37A 108.2 . . ?
N1 C37 H37A 108.2 . . ?
C38 C37 H37B 108.2 . . ?
N1 C37 H37B 108.2 . . ?
H37A C37 H37B 107.3 . . ?
C37 C38 C39 109.1(9) . . ?
C37 C38 H38A 109.9 . . ?
C39 C38 H38A 109.9 . . ?
C37 C38 H38B 109.9 . . ?
C39 C38 H38B 109.9 . . ?
H38A C38 H38B 108.3 . . ?
C40 C39 C38 111.1(10) . . ?
C40 C39 H39A 109.4 . . ?
C38 C39 H39A 109.4 . . ?
C40 C39 H39B 109.4 . . ?
C38 C39 H39B 109.4 . . ?
H39A C39 H39B 108.0 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C42 C41 N1 117.6(10) . . ?
C42 C41 H41A 107.9 . . ?
N1 C41 H41A 107.9 . . ?
C42 C41 H41B 107.9 . . ?
N1 C41 H41B 107.9 . . ?
H41A C41 H41B 107.2 . . ?
C41 C42 C43 113.9(13) . . ?
C41 C42 H42A 108.8 . . ?
C43 C42 H42A 108.8 . . ?
C41 C42 H42B 108.8 . . ?
C43 C42 H42B 108.8 . . ?
H42A C42 H42B 107.7 . . ?
C44 C43 C42 117.2(17) . . ?
C44 C43 H43A 108.0 . . ?
C42 C43 H43A 108.0 . . ?
C44 C43 H43B 108.0 . . ?
C42 C43 H43B 108.0 . . ?
H43A C43 H43B 107.2 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C46 C45 N1 114.9(9) . . ?
C46 C45 H45A 108.5 . . ?
N1 C45 H45A 108.5 . . ?
C46 C45 H45B 108.5 . . ?
N1 C45 H45B 108.5 . . ?
H45A C45 H45B 107.5 . . ?
C47 C46 C45 109.5(10) . . ?
C47 C46 H46A 109.8 . . ?
C45 C46 H46A 109.8 . . ?
C47 C46 H46B 109.8 . . ?
C45 C46 H46B 109.8 . . ?
H46A C46 H46B 108.2 . . ?
C46 C47 C48 110.8(11) . . ?
C46 C47 H47A 109.5 . . ?
C48 C47 H47A 109.5 . . ?
C46 C47 H47B 109.5 . . ?
C48 C47 H47B 109.5 . . ?
H47A C47 H47B 108.1 . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C57 N2 C61 112.6(12) . . ?
C57 N2 C53 109.8(12) . . ?
C61 N2 C53 111.9(11) . . ?
C57 N2 C49 108.9(11) . . ?
C61 N2 C49 104.4(11) . . ?
C53 N2 C49 109.0(12) . . ?
C50 C49 N2 119.6(14) . . ?
C50 C49 H49A 107.4 . . ?
N2 C49 H49A 107.4 . . ?
C50 C49 H49B 107.4 . . ?
N2 C49 H49B 107.4 . . ?
H49A C49 H49B 106.9 . . ?
C49 C50 C51 117.7(16) . . ?
C49 C50 H50A 107.9 . . ?
C51 C50 H50A 107.9 . . ?
C49 C50 H50B 107.9 . . ?
C51 C50 H50B 107.9 . . ?
H50A C50 H50B 107.2 . . ?
C52 C51 C50 125(2) . . ?
C52 C51 H51A 106.1 . . ?
C50 C51 H51A 106.1 . . ?
C52 C51 H51B 106.1 . . ?
C50 C51 H51B 106.1 . . ?
H51A C51 H51B 106.3 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C54 C53 N2 121.9(16) . . ?
C54 C53 H53A 106.8 . . ?
N2 C53 H53A 106.8 . . ?
C54 C53 H53B 106.8 . . ?
N2 C53 H53B 106.8 . . ?
H53A C53 H53B 106.7 . . ?
C55 C54 C53 117.8(17) . . ?
C55 C54 H54A 107.8 . . ?
C53 C54 H54A 107.8 . . ?
C55 C54 H54B 107.8 . . ?
C53 C54 H54B 107.8 . . ?
H54A C54 H54B 107.2 . . ?
C54 C55 C56 123.9(18) . . ?
C54 C55 H55A 106.4 . . ?
C56 C55 H55A 106.4 . . ?
C54 C55 H55B 106.4 . . ?
C56 C55 H55B 106.4 . . ?
H55A C55 H55B 106.4 . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C58 C57 N2 119.4(15) . . ?
C58 C57 H57A 107.5 . . ?
N2 C57 H57A 107.5 . . ?
C58 C57 H57B 107.5 . . ?
N2 C57 H57B 107.5 . . ?
H57A C57 H57B 107.0 . . ?
C57 C58 C59 116.4(16) . . ?
C57 C58 H58A 108.2 . . ?
C59 C58 H58A 108.2 . . ?
C57 C58 H58B 108.2 . . ?
C59 C58 H58B 108.2 . . ?
H58A C58 H58B 107.3 . . ?
C60 C59 C58 120.9(17) . . ?
C60 C59 H59A 107.1 . . ?
C58 C59 H59A 107.1 . . ?
C60 C59 H59B 107.1 . . ?
C58 C59 H59B 107.1 . . ?
H59A C59 H59B 106.8 . . ?
C59 C60 H60A 109.5 . . ?
C59 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C59 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
N2 C61 C62 118.0(12) . . ?
N2 C61 H61A 107.8 . . ?
C62 C61 H61A 107.8 . . ?
N2 C61 H61B 107.8 . . ?
C62 C61 H61B 107.8 . . ?
H61A C61 H61B 107.1 . . ?
C63 C62 C61 115.2(14) . . ?
C63 C62 H62A 108.5 . . ?
C61 C62 H62A 108.5 . . ?
C63 C62 H62B 108.5 . . ?
C61 C62 H62B 108.5 . . ?
H62A C62 H62B 107.5 . . ?
C62 C63 C64 121.6(17) . . ?
C62 C63 H63A 106.9 . . ?
C64 C63 H63A 106.9 . . ?
C62 C63 H63B 106.9 . . ?
C64 C63 H63B 106.9 . . ?
H63A C63 H63B 106.7 . . ?
C63 C64 H64A 109.5 . . ?
C63 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
C63 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F1 179.1(11) . . . . ?
I1 C1 C2 F1 4.8(17) . . . . ?
C6 C1 C2 C3 -1.6(19) . . . . ?
I1 C1 C2 C3 -175.9(9) . . . . ?
C1 C2 C3 F2 178.7(11) . . . . ?
F1 C2 C3 F2 -1.9(16) . . . . ?
C1 C2 C3 C4 0.7(18) . . . . ?
F1 C2 C3 C4 -179.9(10) . . . . ?
C7 O1 C4 C5 -128.8(12) . . . . ?
C7 O1 C4 C3 57.6(15) . . . . ?
F2 C3 C4 O1 -2.8(17) . . . . ?
C2 C3 C4 O1 175.2(11) . . . . ?
F2 C3 C4 C5 -176.5(10) . . . . ?
C2 C3 C4 C5 1.5(17) . . . . ?
O1 C4 C5 F4 5.3(18) . . . . ?
C3 C4 C5 F4 179.4(10) . . . . ?
O1 C4 C5 C6 -176.9(11) . . . . ?
C3 C4 C5 C6 -2.8(18) . . . . ?
C2 C1 C6 C5 0.3(19) . . . . ?
I1 C1 C6 C5 174.8(10) . . . . ?
C2 C1 C6 F3 -179.2(11) . . . . ?
I1 C1 C6 F3 -4.7(17) . . . . ?
C4 C5 C6 C1 2(2) . . . . ?
F4 C5 C6 C1 179.9(12) . . . . ?
C4 C5 C6 F3 -178.6(11) . . . . ?
F4 C5 C6 F3 -0.7(18) . . . . ?
C4 O1 C7 C8 -119.2(11) . . . . ?
C4 O1 C7 C9 116.0(11) . . . . ?
C11 O2 C9 C7 123.4(11) . . . . ?
C11 O2 C9 C10 -114.0(12) . . . . ?
O1 C7 C9 O2 67.2(12) . . . . ?
C8 C7 C9 O2 -55.1(13) . . . . ?
O1 C7 C9 C10 -53.1(13) . . . . ?
C8 C7 C9 C10 -175.4(11) . . . . ?
C9 O2 C11 C12 51.3(17) . . . . ?
C9 O2 C11 C16 -134.4(12) . . . . ?
C16 C11 C12 F8 -177.2(11) . . . . ?
O2 C11 C12 F8 -3.0(19) . . . . ?
C16 C11 C12 C13 -0.6(19) . . . . ?
O2 C11 C12 C13 173.6(12) . . . . ?
F8 C12 C13 C14 175.2(12) . . . . ?
C11 C12 C13 C14 -1(2) . . . . ?
F8 C12 C13 F7 -1.0(18) . . . . ?
C11 C12 C13 F7 -177.6(12) . . . . ?
F7 C13 C14 C15 178.2(11) . . . . ?
C12 C13 C14 C15 2.2(19) . . . . ?
F7 C13 C14 I2 1.9(17) . . . . ?
C12 C13 C14 I2 -174.1(10) . . . . ?
C13 C14 C15 F5 177.7(11) . . . . ?
I2 C14 C15 F5 -5.9(14) . . . . ?
C13 C14 C15 C16 -1.1(16) . . . . ?
I2 C14 C15 C16 175.3(8) . . . . ?
C12 C11 C16 F6 -178.8(11) . . . . ?
O2 C11 C16 F6 6.5(17) . . . . ?
C12 C11 C16 C15 1.7(18) . . . . ?
O2 C11 C16 C15 -172.9(10) . . . . ?
F5 C15 C16 F6 0.8(16) . . . . ?
C14 C15 C16 F6 179.6(10) . . . . ?
F5 C15 C16 C11 -179.7(10) . . . . ?
C14 C15 C16 C11 -0.9(17) . . . . ?
C22 C17 C18 F9 -179.0(11) . . . . ?
I3 C17 C18 F9 -1.5(17) . . . . ?
C22 C17 C18 C19 -2.1(19) . . . . ?
I3 C17 C18 C19 175.4(10) . . . . ?
F9 C18 C19 F10 -3.1(19) . . . . ?
C17 C18 C19 F10 179.9(12) . . . . ?
F9 C18 C19 C20 -179.6(12) . . . . ?
C17 C18 C19 C20 3(2) . . . . ?
F10 C19 C20 C21 -178.4(12) . . . . ?
C18 C19 C20 C21 -2(2) . . . . ?
F10 C19 C20 O3 4.2(19) . . . . ?
C18 C19 C20 O3 -179.3(12) . . . . ?
C23 O3 C20 C21 99.7(14) . . . . ?
C23 O3 C20 C19 -82.9(14) . . . . ?
C19 C20 C21 F12 -178.7(12) . . . . ?
O3 C20 C21 F12 -1(2) . . . . ?
C19 C20 C21 C22 -1(2) . . . . ?
O3 C20 C21 C22 176.6(11) . . . . ?
C18 C17 C22 F11 -178.0(11) . . . . ?
I3 C17 C22 F11 4.5(16) . . . . ?
C18 C17 C22 C21 -0.6(18) . . . . ?
I3 C17 C22 C21 -178.0(9) . . . . ?
F12 C21 C22 F11 -2.6(18) . . . . ?
C20 C21 C22 F11 179.5(12) . . . . ?
F12 C21 C22 C17 180.0(11) . . . . ?
C20 C21 C22 C17 2(2) . . . . ?
C20 O3 C23 C25 156.0(9) . . . . ?
C20 O3 C23 C24 -79.7(13) . . . . ?
C27 O4 C25 C26 -84.2(13) . . . . ?
C27 O4 C25 C23 151.6(10) . . . . ?
O3 C23 C25 C26 -59.8(13) . . . . ?
C24 C23 C25 C26 178.1(12) . . . . ?
O3 C23 C25 O4 61.0(11) . . . . ?
C24 C23 C25 O4 -61.1(14) . . . . ?
C25 O4 C27 C28 -73.5(17) . . . . ?
C25 O4 C27 C32 115.6(13) . . . . ?
O4 C27 C28 F14 6(2) . . . . ?
C32 C27 C28 F14 177.8(13) . . . . ?
O4 C27 C28 C29 -170.3(15) . . . . ?
C32 C27 C28 C29 1(2) . . . . ?
F14 C28 C29 F13 1(2) . . . . ?
C27 C28 C29 F13 178.0(14) . . . . ?
F14 C28 C29 C30 -177.3(13) . . . . ?
C27 C28 C29 C30 -1(3) . . . . ?
F13 C29 C30 C31 179.4(13) . . . . ?
C28 C29 C30 C31 -2(2) . . . . ?
F13 C29 C30 I4 -5.4(19) . . . . ?
C28 C29 C30 I4 173.1(12) . . . . ?
C29 C30 C31 F15 176.7(14) . . . . ?
I4 C30 C31 F15 1(2) . . . . ?
C29 C30 C31 C32 4(2) . . . . ?
I4 C30 C31 C32 -171.2(10) . . . . ?
F15 C31 C32 F16 4(2) . . . . ?
C30 C31 C32 F16 176.6(13) . . . . ?
F15 C31 C32 C27 -176.5(14) . . . . ?
C30 C31 C32 C27 -4(2) . . . . ?
O4 C27 C32 F16 -7.5(19) . . . . ?
C28 C27 C32 F16 -179.2(13) . . . . ?
O4 C27 C32 C31 172.9(13) . . . . ?
C28 C27 C32 C31 1(2) . . . . ?
C45 N1 C33 C34 60.9(13) . . . . ?
C41 N1 C33 C34 -179.1(10) . . . . ?
C37 N1 C33 C34 -61.3(13) . . . . ?
N1 C33 C34 C35 170.1(10) . . . . ?
C33 C34 C35 C36 173.3(13) . . . . ?
C45 N1 C37 C38 -168.7(10) . . . . ?
C33 N1 C37 C38 -47.2(13) . . . . ?
C41 N1 C37 C38 68.6(12) . . . . ?
N1 C37 C38 C39 -179.1(10) . . . . ?
C37 C38 C39 C40 178.9(10) . . . . ?
C45 N1 C41 C42 59.6(13) . . . . ?
C33 N1 C41 C42 -58.7(13) . . . . ?
C37 N1 C41 C42 -178.3(10) . . . . ?
N1 C41 C42 C43 -162.8(12) . . . . ?
C41 C42 C43 C44 76(2) . . . . ?
C33 N1 C45 C46 163.8(10) . . . . ?
C41 N1 C45 C46 47.7(13) . . . . ?
C37 N1 C45 C46 -73.4(13) . . . . ?
N1 C45 C46 C47 173.8(10) . . . . ?
C45 C46 C47 C48 174.6(10) . . . . ?
C57 N2 C49 C50 179.1(15) . . . . ?
C61 N2 C49 C50 58.6(18) . . . . ?
C53 N2 C49 C50 -61.1(18) . . . . ?
N2 C49 C50 C51 173.5(16) . . . . ?
C49 C50 C51 C52 175(2) . . . . ?
C57 N2 C53 C54 71.6(18) . . . . ?
C61 N2 C53 C54 -162.6(14) . . . . ?
C49 N2 C53 C54 -47.6(19) . . . . ?
N2 C53 C54 C55 -170.3(15) . . . . ?
C53 C54 C55 C56 -171(2) . . . . ?
C61 N2 C57 C58 57.5(19) . . . . ?
C53 N2 C57 C58 -177.1(15) . . . . ?
C49 N2 C57 C58 -57.8(19) . . . . ?
N2 C57 C58 C59 -165.2(15) . . . . ?
C57 C58 C59 C60 -172.0(19) . . . . ?
C57 N2 C61 C62 50.7(17) . . . . ?
C53 N2 C61 C62 -73.5(17) . . . . ?
C49 N2 C61 C62 168.8(13) . . . . ?
N2 C61 C62 C63 175.1(13) . . . . ?
C61 C62 C63 C64 172.7(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.72
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.508
_refine_diff_density_min         -3.200
_refine_diff_density_rms         0.214
_database_code_depnum_ccdc_archive 'CCDC 1025199'
#######################################################################
#
#                 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_RR1-Pe4NBr

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
6,6'-(((2R,3R)-butane-2,3-diyl)bis(oxy))
bis(1,2,4,5-tetrafluoro-3-iodobenzene),
tetrapentylammonium bromide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H44 N, 2(C16 H8 F8 I2 O2), Br'
_chemical_formula_sum            'C52 H60 Br F16 I4 N O4 '
_chemical_formula_weight         1654.51
_chemical_absolute_configuration syn

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'
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'
O O 0.0106 0.0060 '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           orthorhombic
_symmetry_space_group_name_H-M   P222
_symmetry_space_group_name_Hall  'P 2 2'


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

_cell_length_a                   9.9519(3)
_cell_length_b                   10.6977(3)
_cell_length_c                   30.4347(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3240.15(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7259
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      27.47


_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1604
_exptl_absorpt_coefficient_mu    2.625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.714
_exptl_absorpt_correction_T_max  0.974

#----------------------------- Remark ------------------------------------#
# SADABS output:                                                          #
# Estimated minimum and maximum transmission:  0.5812  0.7456             #
# The ratio of these values is more reliable than their absolute values!  #
#-------------------------------------------------------------------------#


_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14071
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         0.67
_diffrn_reflns_theta_max         27.52
_reflns_number_total             6357
_reflns_number_gt                5040
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SAINT (Bruker, 2002)'
_computing_cell_refinement       'Bruker SMART (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2002)'
_computing_structure_solution    'SIR97 (ALtomare et al., 1999))'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


_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. 

The following restraints were used to refine the two disordered ammonium:

DFIX 1.5 0.005 N1 C17A N1 C17B C17A C18A C17B C18B C18A C19A
DFIX 1.5 0.005 C18B C19B C19A C20A C19B C20B C20A C21A C20B C21B
DFIX  1.5 0.005 N2 C22A N2 C22B C22A C23A C22B C23B C23A C24A C23B C24B
DFIX  1.5 0.005 C24A C25A C24B C25B  C25A C26A C25B C26B
EXYZ C25A C25B
EXYZ C26A C26B
EXYZ C24A C24B
EADP C26A C26B
EADP C17A C18A C19A C20A C17B C18B C19B C20B
EADP C22A C23A C24A C24B C25A C25B C22B C23B
EADP C21A C21B



;




_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)+(0.0698P)²+20.4616P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(4)
_refine_ls_number_reflns         6357
_refine_ls_number_parameters     335
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1711
_refine_ls_wR_factor_gt          0.1532
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.004
_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 0.0937(14) 0.8846(16) 0.7966(4) 0.064(5) Uani 1 1 d . . .
H1A H 0.1143 0.7975 0.7931 0.096 Uiso 1 1 calc R . .
H1B H 0.0397 0.8959 0.8225 0.096 Uiso 1 1 calc R . .
H1C H 0.1756 0.9312 0.7996 0.096 Uiso 1 1 calc R . .
C2 C 0.0163(13) 0.9310(11) 0.7564(4) 0.047(3) Uani 1 1 d . . .
H2 H 0.0664 0.9100 0.7297 0.057 Uiso 1 1 calc R . .
C3 C -0.1592(12) 0.8274(10) 0.7189(3) 0.029(2) Uani 1 1 d . . .
C4 C -0.1030(13) 0.7304(14) 0.6939(5) 0.048(4) Uani 1 1 d . . .
C5 C -0.1624(12) 0.6838(12) 0.6567(4) 0.036(3) Uani 1 1 d . . .
C6 C -0.2795(13) 0.7340(11) 0.6404(4) 0.033(3) Uani 1 1 d . . .
C7 C -0.3328(13) 0.8312(11) 0.6631(5) 0.040(3) Uani 1 1 d . . .
C8 C -0.2772(15) 0.8775(12) 0.7001(5) 0.050(4) Uani 1 1 d . . .
C9 C 0.6313(12) 0.4194(13) 0.7039(5) 0.057(4) Uani 1 1 d . . .
H9A H 0.7272 0.4142 0.7067 0.086 Uiso 1 1 calc R . .
H9B H 0.6088 0.4631 0.6773 0.086 Uiso 1 1 calc R . .
H9C H 0.5941 0.3366 0.7029 0.086 Uiso 1 1 calc R . .
C10 C 0.5742(10) 0.4890(11) 0.7429(3) 0.030(2) Uani 1 1 d . . .
H10 H 0.5995 0.4453 0.7699 0.036 Uiso 1 1 calc R . .
C11 C 0.6781(11) 0.6610(12) 0.7850(4) 0.033(3) Uani 1 1 d . . .
C12 C 0.7891(12) 0.6115(9) 0.8031(4) 0.026(2) Uani 1 1 d . . .
C13 C 0.8442(12) 0.6655(11) 0.8414(4) 0.030(2) Uani 1 1 d . . .
C14 C 0.7812(11) 0.7717(11) 0.8597(4) 0.027(2) Uani 1 1 d . . .
C15 C 0.6665(12) 0.8160(10) 0.8402(4) 0.032(3) Uani 1 1 d . . .
C16 C 0.6147(12) 0.7632(12) 0.8023(3) 0.031(3) Uani 1 1 d . . .
F1 F 0.0082(9) 0.6717(7) 0.7117(2) 0.0492(19) Uani 1 1 d . . .
F2 F -0.1055(8) 0.5805(8) 0.6369(2) 0.054(2) Uani 1 1 d . . .
F3 F -0.4484(9) 0.8808(8) 0.6489(3) 0.064(3) Uani 1 1 d . . .
F4 F -0.3328(9) 0.9727(7) 0.7227(2) 0.059(2) Uani 1 1 d . . .
F5 F 0.9533(7) 0.6177(7) 0.8589(3) 0.052(2) Uani 1 1 d . . .
F6 F 0.8533(7) 0.5117(7) 0.7867(2) 0.0471(17) Uani 1 1 d . . .
F7 F 0.5044(10) 0.8072(8) 0.7840(3) 0.059(2) Uani 1 1 d . . .
F8 F 0.6042(8) 0.9162(7) 0.8562(3) 0.053(2) Uani 1 1 d . . .
I1 I -0.37120(7) 0.65324(8) 0.58494(3) 0.0415(2) Uani 1 1 d . . .
I2 I 0.86440(7) 0.85213(7) 0.91575(2) 0.03219(19) Uani 1 1 d . . .
Br1 Br 0.5000 0.5000 0.5000 0.0456(7) Uani 1 4 d S . .
Br2 Br 0.0000 0.0000 0.0000 0.0292(5) Uani 1 4 d S . .
O1 O -0.1121(9) 0.8664(10) 0.7561(3) 0.057(3) Uani 1 1 d . . .
O2 O 0.6353(8) 0.6179(7) 0.7431(2) 0.0354(19) Uani 1 1 d . . .
N1 N 0.0000 0.5000 0.5000 0.033(5) Uani 1 4 d SD . .
C17A C 0.042(2) 0.567(2) 0.5409(4) 0.057(3) Uani 0.50 1 d PD A 1
H17A H 0.0752 0.5069 0.5621 0.068 Uiso 0.50 1 calc PR A 1
H17B H -0.0358 0.6083 0.5537 0.068 Uiso 0.50 1 calc PR A 1
C18A C 0.149(2) 0.662(2) 0.5315(7) 0.057(3) Uani 0.50 1 d PD A 1
H18A H 0.1178 0.7192 0.5089 0.068 Uiso 0.50 1 calc PR A 1
H18B H 0.2289 0.6205 0.5208 0.068 Uiso 0.50 1 calc PR A 1
C19A C 0.181(3) 0.733(2) 0.5727(7) 0.057(3) Uani 0.50 1 d PD A 1
H19A H 0.1047 0.7158 0.5918 0.068 Uiso 0.50 1 calc PR A 1
H19B H 0.2555 0.6877 0.5853 0.068 Uiso 0.50 1 calc PR A 1
C20A C 0.213(3) 0.868(2) 0.5825(8) 0.057(3) Uani 0.50 1 d PD A 1
H20A H 0.3093 0.8837 0.5829 0.068 Uiso 0.50 1 calc PR A 1
H20B H 0.1689 0.9253 0.5626 0.068 Uiso 0.50 1 calc PR A 1
C21A C 0.152(6) 0.868(6) 0.6276(11) 0.162(17) Uiso 0.50 1 d PD A 1
H21A H 0.0583 0.8861 0.6255 0.243 Uiso 0.50 1 calc PR A 1
H21B H 0.1958 0.9300 0.6453 0.243 Uiso 0.50 1 calc PR A 1
H21C H 0.1644 0.7869 0.6408 0.243 Uiso 0.50 1 calc PR A 1
C17B C 0.1121(17) 0.586(2) 0.5142(7) 0.057(3) Uani 0.50 1 d PD . 2
H17C H 0.1875 0.5325 0.5217 0.068 Uiso 0.50 1 calc PR . 2
H17D H 0.1388 0.6322 0.4882 0.068 Uiso 0.50 1 calc PR . 2
C18B C 0.100(2) 0.680(2) 0.5506(8) 0.057(3) Uani 0.50 1 d PD . 2
H18C H 0.0908 0.6355 0.5782 0.068 Uiso 0.50 1 calc PR . 2
H18D H 0.0188 0.7282 0.5461 0.068 Uiso 0.50 1 calc PR . 2
C19B C 0.217(2) 0.768(2) 0.5541(9) 0.057(3) Uani 0.50 1 d PD . 2
H19C H 0.2727 0.7230 0.5748 0.068 Uiso 0.50 1 calc PR . 2
H19D H 0.2597 0.7535 0.5259 0.068 Uiso 0.50 1 calc PR . 2
C20B C 0.263(3) 0.899(2) 0.5629(8) 0.057(3) Uani 0.50 1 d PD . 2
H20C H 0.2282 0.9545 0.5403 0.068 Uiso 0.50 1 calc PR . 2
H20D H 0.3603 0.9027 0.5618 0.068 Uiso 0.50 1 calc PR . 2
C21B C 0.215(6) 0.943(5) 0.6071(11) 0.162(17) Uiso 0.50 1 d PD . 2
H21D H 0.2552 1.0227 0.6136 0.243 Uiso 0.50 1 calc PR . 2
H21E H 0.2411 0.8835 0.6291 0.243 Uiso 0.50 1 calc PR . 2
H21F H 0.1193 0.9513 0.6067 0.243 Uiso 0.50 1 calc PR . 2
N2 N 0.5000 0.0000 0.0000 0.050(7) Uani 1 4 d SD . .
C22A C 0.457(4) 0.065(3) 0.0413(6) 0.101(4) Uani 0.50 1 d PD B 3
H22A H 0.5342 0.1037 0.0550 0.121 Uiso 0.50 1 calc PR B 3
H22B H 0.4209 0.0035 0.0617 0.121 Uiso 0.50 1 calc PR B 3
C23A C 0.352(4) 0.162(3) 0.0319(10) 0.101(4) Uani 0.50 1 d PD B 3
H23A H 0.2794 0.1172 0.0176 0.121 Uiso 0.50 1 calc PR B 3
H23B H 0.3913 0.2151 0.0095 0.121 Uiso 0.50 1 calc PR B 3
C24A C 0.285(2) 0.2497(18) 0.0636(6) 0.101(4) Uani 0.50 1 d PD B 3
H24A H 0.2563 0.3128 0.0427 0.121 Uiso 0.50 1 calc PR B 3
H24B H 0.2042 0.2014 0.0690 0.121 Uiso 0.50 1 calc PR B 3
C25A C 0.283(2) 0.3285(18) 0.1043(6) 0.101(4) Uani 0.50 1 d PD B 3
H25A H 0.2022 0.3796 0.1028 0.121 Uiso 0.50 1 calc PR B 3
H25B H 0.2710 0.2722 0.1290 0.121 Uiso 0.50 1 calc PR B 3
C26A C 0.397(2) 0.414(2) 0.1156(11) 0.34(3) Uani 0.50 1 d PD B 3
H26A H 0.3967 0.4299 0.1466 0.511 Uiso 0.50 1 calc PR B 3
H26B H 0.3865 0.4915 0.1000 0.511 Uiso 0.50 1 calc PR B 3
H26C H 0.4801 0.3756 0.1073 0.511 Uiso 0.50 1 calc PR B 3
C22B C 0.396(2) 0.095(3) 0.0131(13) 0.101(4) Uani 0.50 1 d PD B 4
H22C H 0.3703 0.1373 -0.0138 0.121 Uiso 0.50 1 calc PR B 4
H22D H 0.3181 0.0475 0.0224 0.121 Uiso 0.50 1 calc PR B 4
C23B C 0.414(2) 0.196(4) 0.0468(13) 0.101(4) Uani 0.50 1 d PD B 4
H23C H 0.4642 0.1620 0.0715 0.121 Uiso 0.50 1 calc PR B 4
H23D H 0.4674 0.2626 0.0341 0.121 Uiso 0.50 1 calc PR B 4
C24B C 0.285(2) 0.2497(18) 0.0636(6) 0.101(4) Uani 0.50 1 d PD B 4
H24C H 0.2240 0.1803 0.0684 0.121 Uiso 0.50 1 calc PR B 4
H24D H 0.2470 0.2996 0.0400 0.121 Uiso 0.50 1 calc PR B 4
C25B C 0.283(2) 0.3285(18) 0.1043(6) 0.101(4) Uani 0.50 1 d PD B 4
H25C H 0.2022 0.3796 0.1028 0.121 Uiso 0.50 1 calc PR B 4
H25D H 0.2710 0.2722 0.1290 0.121 Uiso 0.50 1 calc PR B 4
C26B C 0.397(2) 0.414(2) 0.1156(11) 0.34(3) Uani 0.50 1 d PD B 4
H26D H 0.3955 0.4314 0.1465 0.511 Uiso 0.50 1 calc PR B 4
H26E H 0.3875 0.4908 0.0995 0.511 Uiso 0.50 1 calc PR B 4
H26F H 0.4802 0.3748 0.1079 0.511 Uiso 0.50 1 calc PR B 4


_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 1.529(17) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.453(14) . ?
C2 C2 1.51(3) 2_575 ?
C2 H2 0.9800 . ?
C3 O1 1.297(14) . ?
C3 C4 1.402(18) . ?
C3 C8 1.411(19) . ?
C4 C5 1.371(18) . ?
C4 F1 1.383(16) . ?
C5 C6 1.375(18) . ?
C5 F2 1.380(14) . ?
C6 C7 1.356(17) . ?
C6 I1 2.105(11) . ?
C7 F3 1.339(14) . ?
C7 C8 1.348(19) . ?
C8 F4 1.348(15) . ?
C9 C10 1.511(15) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C10 1.496(19) 2_665 ?
C10 O2 1.507(14) . ?
C10 H10 0.9800 . ?
C11 C12 1.344(16) . ?
C11 C16 1.367(17) . ?
C11 O2 1.422(13) . ?
C12 F6 1.341(12) . ?
C12 C13 1.409(15) . ?
C13 F5 1.313(13) . ?
C13 C14 1.413(15) . ?
C14 C15 1.371(16) . ?
C14 I2 2.082(12) . ?
C15 F8 1.331(13) . ?
C15 C16 1.385(16) . ?
C16 F7 1.317(15) . ?
N1 C17A 1.495(5) 3_566 ?
N1 C17A 1.495(5) 4_556 ?
N1 C17A 1.495(5) . ?
N1 C17A 1.495(5) 2_565 ?
N1 C17B 1.508(5) . ?
N1 C17B 1.508(5) 3_566 ?
N1 C17B 1.508(5) 2_565 ?
N1 C17B 1.508(5) 4_556 ?
C17A C18A 1.500(5) . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C18A C19A 1.504(5) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C19A C20A 1.502(5) . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C20A C21A 1.501(5) . ?
C20A H20A 0.9700 . ?
C20A H20B 0.9700 . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
C17B C18B 1.502(5) . ?
C17B C17B 2.03(4) 3_566 ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?
C18B C19B 1.502(5) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C19B C20B 1.500(5) . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C20B C21B 1.501(5) . ?
C20B H20C 0.9700 . ?
C20B H20D 0.9700 . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?
N2 C22A 1.496(5) 4_655 ?
N2 C22A 1.496(5) 3 ?
N2 C22A 1.496(5) . ?
N2 C22A 1.496(5) 2_655 ?
N2 C22B 1.504(5) . ?
N2 C22B 1.504(5) 4_655 ?
N2 C22B 1.504(5) 2_655 ?
N2 C22B 1.504(5) 3 ?
C22A C23A 1.501(5) . ?
C22A H22A 0.9700 . ?
C22A H22B 0.9700 . ?
C23A C24A 1.504(5) . ?
C23A H23A 0.9700 . ?
C23A H23B 0.9700 . ?
C24A C25A 1.499(4) . ?
C24A H24A 0.9700 . ?
C24A H24B 0.9700 . ?
C25A C26A 1.499(4) . ?
C25A H25A 0.9700 . ?
C25A H25B 0.9700 . ?
C26A H26A 0.9600 . ?
C26A H26B 0.9600 . ?
C26A H26C 0.9600 . ?
C22B C23B 1.500(5) . ?
C22B H22C 0.9700 . ?
C22B H22D 0.9700 . ?
C23B H23C 0.9700 . ?
C23B H23D 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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C2 106.0(13) . 2_575 ?
O1 C2 C1 107.0(10) . . ?
C2 C2 C1 115.2(9) 2_575 . ?
O1 C2 H2 109.5 . . ?
C2 C2 H2 109.5 2_575 . ?
C1 C2 H2 109.5 . . ?
O1 C3 C4 124.6(12) . . ?
O1 C3 C8 122.2(12) . . ?
C4 C3 C8 113.2(11) . . ?
C5 C4 F1 120.2(13) . . ?
C5 C4 C3 122.9(12) . . ?
F1 C4 C3 116.4(13) . . ?
C4 C5 C6 121.4(12) . . ?
C4 C5 F2 118.3(12) . . ?
C6 C5 F2 120.2(10) . . ?
C7 C6 C5 116.6(11) . . ?
C7 C6 I1 123.6(10) . . ?
C5 C6 I1 119.8(9) . . ?
F3 C7 C8 118.5(13) . . ?
F3 C7 C6 118.4(12) . . ?
C8 C7 C6 123.1(13) . . ?
F4 C8 C7 122.3(14) . . ?
F4 C8 C3 115.0(13) . . ?
C7 C8 C3 122.6(12) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C10 O2 104.7(11) 2_665 . ?
C10 C10 C9 116.7(8) 2_665 . ?
O2 C10 C9 107.6(9) . . ?
C10 C10 H10 109.2 2_665 . ?
O2 C10 H10 109.2 . . ?
C9 C10 H10 109.2 . . ?
C12 C11 C16 122.4(11) . . ?
C12 C11 O2 119.2(11) . . ?
C16 C11 O2 117.8(10) . . ?
F6 C12 C11 123.5(10) . . ?
F6 C12 C13 116.6(10) . . ?
C11 C12 C13 119.8(10) . . ?
F5 C13 C14 121.3(10) . . ?
F5 C13 C12 119.8(10) . . ?
C14 C13 C12 118.9(11) . . ?
C15 C14 C13 118.4(11) . . ?
C15 C14 I2 122.9(9) . . ?
C13 C14 I2 118.7(8) . . ?
F8 C15 C14 120.5(12) . . ?
F8 C15 C16 117.4(11) . . ?
C14 C15 C16 122.0(11) . . ?
F7 C16 C11 120.6(10) . . ?
F7 C16 C15 121.0(11) . . ?
C11 C16 C15 118.4(11) . . ?
C3 O1 C2 118.4(9) . . ?
C11 O2 C10 114.9(7) . . ?
C17A N1 C17A 67.3(16) 3_566 4_556 ?
C17A N1 C17A 147.8(19) 3_566 . ?
C17A N1 C17A 123(2) 4_556 . ?
C17A N1 C17A 123(2) 3_566 2_565 ?
C17A N1 C17A 147.8(19) 4_556 2_565 ?
C17A N1 C17A 67.3(16) . 2_565 ?
C17A N1 C17B 108.9(14) 3_566 . ?
C17A N1 C17B 98.7(15) 4_556 . ?
C17A N1 C17B 42.7(11) . . ?
C17A N1 C17B 105.0(11) 2_565 . ?
C17A N1 C17B 42.7(11) 3_566 3_566 ?
C17A N1 C17B 105.0(11) 4_556 3_566 ?
C17A N1 C17B 108.9(14) . 3_566 ?
C17A N1 C17B 98.7(15) 2_565 3_566 ?
C17B N1 C17B 84.5(19) . 3_566 ?
C17A N1 C17B 98.7(15) 3_566 2_565 ?
C17A N1 C17B 108.9(14) 4_556 2_565 ?
C17A N1 C17B 105.0(11) . 2_565 ?
C17A N1 C17B 42.7(11) 2_565 2_565 ?
C17B N1 C17B 146.8(17) . 2_565 ?
C17B N1 C17B 105(2) 3_566 2_565 ?
C17A N1 C17B 105.0(11) 3_566 4_556 ?
C17A N1 C17B 42.7(11) 4_556 4_556 ?
C17A N1 C17B 98.7(15) . 4_556 ?
C17A N1 C17B 108.9(14) 2_565 4_556 ?
C17B N1 C17B 105(2) . 4_556 ?
C17B N1 C17B 146.8(17) 3_566 4_556 ?
C17B N1 C17B 84.5(19) 2_565 4_556 ?
N1 C17A C18A 111.3(12) . . ?
N1 C17A H17A 109.4 . . ?
C18A C17A H17A 109.4 . . ?
N1 C17A H17B 109.4 . . ?
C18A C17A H17B 109.4 . . ?
H17A C17A H17B 108.0 . . ?
C17A C18A C19A 109.5(14) . . ?
C17A C18A H18A 109.8 . . ?
C19A C18A H18A 109.8 . . ?
C17A C18A H18B 109.8 . . ?
C19A C18A H18B 109.8 . . ?
H18A C18A H18B 108.2 . . ?
C20A C19A C18A 134(2) . . ?
C20A C19A H19A 103.7 . . ?
C18A C19A H19A 103.7 . . ?
C20A C19A H19B 103.7 . . ?
C18A C19A H19B 103.7 . . ?
H19A C19A H19B 105.3 . . ?
C21A C20A C19A 95(3) . . ?
C21A C20A H20A 112.7 . . ?
C19A C20A H20A 112.7 . . ?
C21A C20A H20B 112.7 . . ?
C19A C20A H20B 112.7 . . ?
H20A C20A H20B 110.2 . . ?
C20A C21A H21A 109.5 . . ?
C20A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C20A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C18B C17B N1 124.0(13) . . ?
C18B C17B C17B 157(3) . 3_566 ?
N1 C17B C17B 47.7(9) . 3_566 ?
C18B C17B H17C 106.3 . . ?
N1 C17B H17C 106.3 . . ?
C17B C17B H17C 64.4 3_566 . ?
C18B C17B H17D 106.3 . . ?
N1 C17B H17D 106.3 . . ?
C17B C17B H17D 96.7 3_566 . ?
H17C C17B H17D 106.4 . . ?
C17B C18B C19B 114.3(14) . . ?
C17B C18B H18C 108.7 . . ?
C19B C18B H18C 108.7 . . ?
C17B C18B H18D 108.7 . . ?
C19B C18B H18D 108.7 . . ?
H18C C18B H18D 107.6 . . ?
C20B C19B C18B 147(2) . . ?
C20B C19B H19C 100.1 . . ?
C18B C19B H19C 100.1 . . ?
C20B C19B H19D 100.1 . . ?
C18B C19B H19D 100.1 . . ?
H19C C19B H19D 104.2 . . ?
C19B C20B C21B 111(3) . . ?
C19B C20B H20C 109.5 . . ?
C21B C20B H20C 109.5 . . ?
C19B C20B H20D 109.5 . . ?
C21B C20B H20D 109.5 . . ?
H20C C20B H20D 108.1 . . ?
C20B C21B H21D 109.5 . . ?
C20B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C20B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C22A N2 C22A 66(2) 4_655 3 ?
C22A N2 C22A 125(3) 4_655 . ?
C22A N2 C22A 147(3) 3 . ?
C22A N2 C22A 147(3) 4_655 2_655 ?
C22A N2 C22A 125(3) 3 2_655 ?
C22A N2 C22A 66(2) . 2_655 ?
C22A N2 C22B 96(2) 4_655 . ?
C22A N2 C22B 110(2) 3 . ?
C22A N2 C22B 43.0(19) . . ?
C22A N2 C22B 106.6(19) 2_655 . ?
C22A N2 C22B 43.0(19) 4_655 4_655 ?
C22A N2 C22B 106.6(19) 3 4_655 ?
C22A N2 C22B 96(2) . 4_655 ?
C22A N2 C22B 110(2) 2_655 4_655 ?
C22B N2 C22B 95(3) . 4_655 ?
C22A N2 C22B 110(2) 4_655 2_655 ?
C22A N2 C22B 96(2) 3 2_655 ?
C22A N2 C22B 106.6(19) . 2_655 ?
C22A N2 C22B 43.0(19) 2_655 2_655 ?
C22B N2 C22B 149(3) . 2_655 ?
C22B N2 C22B 93(3) 4_655 2_655 ?
C22A N2 C22B 106.6(19) 4_655 3 ?
C22A N2 C22B 43.0(19) 3 3 ?
C22A N2 C22B 110(2) . 3 ?
C22A N2 C22B 96(2) 2_655 3 ?
C22B N2 C22B 93(3) . 3 ?
C22B N2 C22B 149(3) 4_655 3 ?
C22B N2 C22B 95(3) 2_655 3 ?
N2 C22A C23A 111.1(12) . . ?
N2 C22A H22A 109.4 . . ?
C23A C22A H22A 109.4 . . ?
N2 C22A H22B 109.4 . . ?
C23A C22A H22B 109.4 . . ?
H22A C22A H22B 108.0 . . ?
C22A C23A C24A 128(2) . . ?
C22A C23A H23A 105.2 . . ?
C24A C23A H23A 105.2 . . ?
C22A C23A H23B 105.2 . . ?
C24A C23A H23B 105.2 . . ?
H23A C23A H23B 105.9 . . ?
C25A C24A C23A 153(2) . . ?
C25A C24A H24A 98.4 . . ?
C23A C24A H24A 98.4 . . ?
C25A C24A H24B 98.4 . . ?
C23A C24A H24B 98.4 . . ?
H24A C24A H24B 103.8 . . ?
C26A C25A C24A 121.4(17) . . ?
C26A C25A H25A 107.0 . . ?
C24A C25A H25A 107.0 . . ?
C26A C25A H25B 107.0 . . ?
C24A C25A H25B 107.0 . . ?
H25A C25A H25B 106.7 . . ?
C25A C26A H26A 109.5 . . ?
C25A C26A H26B 109.5 . . ?
H26A C26A H26B 109.5 . . ?
C25A C26A H26C 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
C23B C22B N2 125.8(19) . . ?
C23B C22B H22C 105.9 . . ?
N2 C22B H22C 105.9 . . ?
C23B C22B H22D 105.9 . . ?
N2 C22B H22D 105.9 . . ?
H22C C22B H22D 106.2 . . ?
C22B C23B H23C 108.8 . . ?
C22B C23B H23D 108.8 . . ?
H23C C23B H23D 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 C5 173.8(12) . . . . ?
C8 C3 C4 C5 -4.3(18) . . . . ?
O1 C3 C4 F1 1.8(18) . . . . ?
C8 C3 C4 F1 -176.2(10) . . . . ?
F1 C4 C5 C6 174.5(11) . . . . ?
C3 C4 C5 C6 3(2) . . . . ?
F1 C4 C5 F2 -2.3(18) . . . . ?
C3 C4 C5 F2 -173.9(10) . . . . ?
C4 C5 C6 C7 -0.2(19) . . . . ?
F2 C5 C6 C7 176.6(11) . . . . ?
C4 C5 C6 I1 -177.1(10) . . . . ?
F2 C5 C6 I1 -0.3(16) . . . . ?
C5 C6 C7 F3 -178.5(12) . . . . ?
I1 C6 C7 F3 -1.7(17) . . . . ?
C5 C6 C7 C8 -0.7(19) . . . . ?
I1 C6 C7 C8 176.1(10) . . . . ?
F3 C7 C8 F4 -1.0(19) . . . . ?
C6 C7 C8 F4 -178.7(12) . . . . ?
F3 C7 C8 C3 176.7(11) . . . . ?
C6 C7 C8 C3 -1(2) . . . . ?
O1 C3 C8 F4 3.2(16) . . . . ?
C4 C3 C8 F4 -178.8(10) . . . . ?
O1 C3 C8 C7 -174.7(12) . . . . ?
C4 C3 C8 C7 3.4(17) . . . . ?
C16 C11 C12 F6 -179.8(11) . . . . ?
O2 C11 C12 F6 -9.1(17) . . . . ?
C16 C11 C12 C13 0.0(18) . . . . ?
O2 C11 C12 C13 170.6(10) . . . . ?
F6 C12 C13 F5 0.2(16) . . . . ?
C11 C12 C13 F5 -179.5(11) . . . . ?
F6 C12 C13 C14 179.4(10) . . . . ?
C11 C12 C13 C14 -0.3(16) . . . . ?
F5 C13 C14 C15 -179.2(11) . . . . ?
C12 C13 C14 C15 1.7(15) . . . . ?
F5 C13 C14 I2 -0.1(14) . . . . ?
C12 C13 C14 I2 -179.3(8) . . . . ?
C13 C14 C15 F8 -179.6(10) . . . . ?
I2 C14 C15 F8 1.4(15) . . . . ?
C13 C14 C15 C16 -2.8(17) . . . . ?
I2 C14 C15 C16 178.3(9) . . . . ?
C12 C11 C16 F7 -178.6(11) . . . . ?
O2 C11 C16 F7 10.7(17) . . . . ?
C12 C11 C16 C15 -0.9(18) . . . . ?
O2 C11 C16 C15 -171.7(10) . . . . ?
F8 C15 C16 F7 -3.1(17) . . . . ?
C14 C15 C16 F7 -180.0(11) . . . . ?
F8 C15 C16 C11 179.3(10) . . . . ?
C14 C15 C16 C11 2.4(18) . . . . ?
C4 C3 O1 C2 68.5(16) . . . . ?
C8 C3 O1 C2 -113.7(13) . . . . ?
C2 C2 O1 C3 97.2(10) 2_575 . . . ?
C1 C2 O1 C3 -139.4(13) . . . . ?
C12 C11 O2 C10 73.0(13) . . . . ?
C16 C11 O2 C10 -116.0(11) . . . . ?
C10 C10 O2 C11 99.0(8) 2_665 . . . ?
C9 C10 O2 C11 -136.2(10) . . . . ?
C17A N1 C17A C18A 47.1(19) 3_566 . . . ?
C17A N1 C17A C18A -52.0(18) 4_556 . . . ?
C17A N1 C17A C18A 163(4) 2_565 . . . ?
C17B N1 C17A C18A 13(2) . . . . ?
C17B N1 C17A C18A 71(3) 3_566 . . . ?
C17B N1 C17A C18A -177(2) 2_565 . . . ?
C17B N1 C17A C18A -90(2) 4_556 . . . ?
N1 C17A C18A C19A 176(2) . . . . ?
C17A C18A C19A C20A -142(3) . . . . ?
C18A C19A C20A C21A 149(4) . . . . ?
C17A N1 C17B C18B 172(2) 3_566 . . . ?
C17A N1 C17B C18B 103(3) 4_556 . . . ?
C17A N1 C17B C18B -27(2) . . . . ?
C17A N1 C17B C18B -55(3) 2_565 . . . ?
C17B N1 C17B C18B -152(3) 3_566 . . . ?
C17B N1 C17B C18B -43(2) 2_565 . . . ?
C17B N1 C17B C18B 60(2) 4_556 . . . ?
C17A N1 C17B C17B -35.6(18) 3_566 . . 3_566 ?
C17A N1 C17B C17B -104.4(13) 4_556 . . 3_566 ?
C17A N1 C17B C17B 126(3) . . . 3_566 ?
C17A N1 C17B C17B 97.6(15) 2_565 . . 3_566 ?
C17B N1 C17B C17B 109.1(13) 2_565 . . 3_566 ?
C17B N1 C17B C17B -147.6(16) 4_556 . . 3_566 ?
N1 C17B C18B C19B -171(2) . . . . ?
C17B C17B C18B C19B 128(3) 3_566 . . . ?
C17B C18B C19B C20B 141(4) . . . . ?
C18B C19B C20B C21B 56(6) . . . . ?
C22A N2 C22A C23A 50(3) 4_655 . . . ?
C22A N2 C22A C23A -49(3) 3 . . . ?
C22A N2 C22A C23A -166(5) 2_655 . . . ?
C22B N2 C22A C23A -6(3) . . . . ?
C22B N2 C22A C23A 85(3) 4_655 . . . ?
C22B N2 C22A C23A -180(3) 2_655 . . . ?
C22B N2 C22A C23A -78(4) 3 . . . ?
N2 C22A C23A C24A -178(3) . . . . ?
C22A C23A C24A C25A 31(8) . . . . ?
C23A C24A C25A C26A 46(6) . . . . ?
C22A N2 C22B C23B -100(4) 4_655 . . . ?
C22A N2 C22B C23B -167(4) 3 . . . ?
C22A N2 C22B C23B 37(4) . . . . ?
C22A N2 C22B C23B 55(5) 2_655 . . . ?
C22B N2 C22B C23B -57(3) 4_655 . . . ?
C22B N2 C22B C23B 47(4) 2_655 . . . ?
C22B N2 C22B C23B 153(5) 3 . . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         1.339
_refine_diff_density_min         -1.240
_refine_diff_density_rms         0.252
_database_code_depnum_ccdc_archive 'CCDC 1025200'
