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

data_global

_journal_coden_Cambridge         1350

loop_
_publ_author_name
'Marc Fourmigue'
'P Cauliez'
'Rosa Llusar'
'Victor Polo'
'Thierry Roisnel'

_publ_contact_author_name        'Marc Fourmigue'
_publ_contact_author_email       MARC.FOURMIGUE@UNIV-RENNES1.FR

_publ_section_title              
;
The thiocyanate anion as a polydentate halogen bond acceptor
;
_publ_requested_category         FO

# Attachment '1a_PC30.cif'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2008-01-29 at 18:46:43
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:\progs\wingx\files\archive.dat
# CIF files read : job struct

data_job
_database_code_depnum_ccdc_archive 'CCDC 739580'

_audit_creation_date             2008-01-29T18:46:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
tetraethylammonium thiocyanate, bis[(1,2-diiodo)tetrafluorobenzene]
;
_chemical_formula_moiety         'C8 H20 N, 2(C6 F4 I2), C N S'
_chemical_formula_sum            'C21 H20 F8 I4 N2 S'
_chemical_formula_weight         992.05
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
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'
'-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                   15.809(7)
_cell_length_b                   16.566(8)
_cell_length_c                   21.461(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5621(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4570
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.53
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    2.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3680
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.577
_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  0.104
_exptl_absorpt_correction_T_max  0.795

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_number            18884
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_reflns_number_total             6355
_reflns_number_gt                4621
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_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)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0775P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6355
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.077
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.126
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.631
_refine_diff_density_min         -2.351
_refine_diff_density_rms         0.307

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0957(4) -0.0606(5) 0.4586(3) 0.0164(16) Uani 1 d . . .
I1 I 0.07082(3) -0.16913(3) 0.41090(2) 0.01870(15) Uani 1 d . . .
C2 C 0.0738(4) 0.0157(5) 0.4345(3) 0.0162(17) Uani 1 d . . .
I2 I 0.01479(2) 0.03135(3) 0.34687(2) 0.01623(14) Uani 1 d . . .
C3 C 0.0940(4) 0.0852(6) 0.4681(4) 0.0197(17) Uani 1 d . . .
F3A F 0.0733(3) 0.1594(3) 0.4471(2) 0.0256(11) Uani 1 d . . .
C4 C 0.1346(4) 0.0811(6) 0.5246(3) 0.0190(18) Uani 1 d . . .
F4A F 0.1563(3) 0.1483(3) 0.5561(2) 0.0268(12) Uani 1 d . . .
C5 C 0.1570(4) 0.0052(6) 0.5473(3) 0.023(2) Uani 1 d . . .
F5A F 0.1996(3) 0.0005(4) 0.6023(2) 0.0318(13) Uani 1 d . . .
C6 C 0.1371(4) -0.0638(6) 0.5151(3) 0.0217(19) Uani 1 d . . .
F6A F 0.1608(3) -0.1357(4) 0.5394(2) 0.0290(12) Uani 1 d . . .
C11 C 0.3763(4) 0.0331(5) 0.5231(3) 0.0167(17) Uani 1 d . . .
I11 I 0.44664(3) 0.02644(4) 0.60534(2) 0.01879(15) Uani 1 d . . .
I12 I 0.39493(3) -0.15394(4) 0.51257(2) 0.02488(16) Uani 1 d . . .
C12 C 0.3582(4) -0.0371(5) 0.4881(4) 0.0164(16) Uani 1 d . . .
C13 C 0.3132(4) -0.0290(5) 0.4327(4) 0.0187(18) Uani 1 d . . .
F13A F 0.2942(3) -0.0930(3) 0.39682(19) 0.0264(12) Uani 1 d . . .
C14 C 0.2860(4) 0.0464(6) 0.4127(3) 0.0191(18) Uani 1 d . . .
F14A F 0.2405(2) 0.0541(3) 0.3600(2) 0.0250(11) Uani 1 d . . .
C15 C 0.3031(4) 0.1142(6) 0.4462(4) 0.0229(19) Uani 1 d . . .
F15A F 0.2732(3) 0.1867(3) 0.4285(2) 0.0256(11) Uani 1 d . . .
C16 C 0.3484(4) 0.1070(6) 0.5018(3) 0.0202(18) Uani 1 d . . .
F16A F 0.3631(3) 0.1750(3) 0.5347(2) 0.0251(11) Uani 1 d . . .
S21 S 0.42290(11) 0.03093(15) 0.28346(9) 0.0216(5) Uani 1 d . . .
C22 C 0.4389(4) 0.1242(6) 0.3118(3) 0.0199(18) Uani 1 d . . .
N23 N 0.4502(4) 0.1875(5) 0.3313(3) 0.0292(17) Uani 1 d . . .
N31 N 0.2256(3) 0.2635(4) 0.2244(3) 0.0161(14) Uani 1 d . . .
C31 C 0.2766(4) 0.2616(6) 0.1642(3) 0.0199(18) Uani 1 d . . .
H31A H 0.245 0.2294 0.133 0.024 Uiso 1 calc R . .
H31B H 0.2812 0.3174 0.148 0.024 Uiso 1 calc R . .
C32 C 0.3643(4) 0.2269(7) 0.1705(4) 0.031(2) Uani 1 d . . .
H32A H 0.3971 0.2596 0.1999 0.046 Uiso 1 calc R . .
H32B H 0.3923 0.2273 0.1298 0.046 Uiso 1 calc R . .
H32C H 0.3606 0.1713 0.1859 0.046 Uiso 1 calc R . .
C33 C 0.2708(4) 0.3137(6) 0.2738(3) 0.0200(18) Uani 1 d . . .
H33A H 0.2361 0.3129 0.3122 0.024 Uiso 1 calc R . .
H33B H 0.3252 0.287 0.2836 0.024 Uiso 1 calc R . .
C34 C 0.2885(5) 0.4002(6) 0.2571(4) 0.0236(19) Uani 1 d . . .
H34A H 0.3233 0.4022 0.2194 0.035 Uiso 1 calc R . .
H34B H 0.3188 0.4263 0.2915 0.035 Uiso 1 calc R . .
H34C H 0.235 0.4285 0.2497 0.035 Uiso 1 calc R . .
C35 C 0.2154(4) 0.1791(5) 0.2513(4) 0.0173(16) Uani 1 d . . .
H35A H 0.2719 0.1586 0.2633 0.021 Uiso 1 calc R . .
H35B H 0.1811 0.1829 0.2898 0.021 Uiso 1 calc R . .
C36 C 0.1746(4) 0.1185(6) 0.2086(4) 0.0234(18) Uani 1 d . . .
H36A H 0.1179 0.1373 0.1972 0.035 Uiso 1 calc R . .
H36B H 0.1703 0.0663 0.23 0.035 Uiso 1 calc R . .
H36C H 0.209 0.1124 0.171 0.035 Uiso 1 calc R . .
C37 C 0.1412(4) 0.3013(6) 0.2082(4) 0.0210(18) Uani 1 d . . .
H37A H 0.1144 0.2688 0.1749 0.025 Uiso 1 calc R . .
H37B H 0.1514 0.356 0.1913 0.025 Uiso 1 calc R . .
C38 C 0.0798(5) 0.3079(6) 0.2624(4) 0.0242(19) Uani 1 d . . .
H38A H 0.0668 0.2538 0.2782 0.036 Uiso 1 calc R . .
H38B H 0.0276 0.3339 0.2482 0.036 Uiso 1 calc R . .
H38C H 0.1054 0.3402 0.2957 0.036 Uiso 1 calc R . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C6 1.378(10) . ?
C1 C2 1.410(12) . ?
C1 I1 2.106(8) . ?
C2 C3 1.396(12) . ?
C2 I2 2.115(7) . ?
C3 F3A 1.351(10) . ?
C3 C4 1.372(10) . ?
C4 F4A 1.346(10) . ?
C4 C5 1.394(13) . ?
C5 F5A 1.361(8) . ?
C5 C6 1.373(13) . ?
C6 F6A 1.353(10) . ?
C11 C16 1.379(12) . ?
C11 C12 1.414(11) . ?
C11 I11 2.089(7) . ?
I12 C12 2.087(8) . ?
C12 C13 1.391(10) . ?
C13 F13A 1.344(9) . ?
C13 C14 1.390(12) . ?
C14 F14A 1.345(8) . ?
C14 C15 1.361(13) . ?
C15 F15A 1.346(10) . ?
C15 C16 1.397(10) . ?
C16 F16A 1.349(10) . ?
S21 C22 1.679(10) . ?
C22 N23 1.144(12) . ?
N31 C37 1.513(8) . ?
N31 C35 1.522(10) . ?
N31 C31 1.523(9) . ?
N31 C33 1.524(10) . ?
C31 C32 1.508(9) . ?
C31 H31A 0.99 . ?
C31 H31B 0.99 . ?
C32 H32A 0.98 . ?
C32 H32B 0.98 . ?
C32 H32C 0.98 . ?
C33 C34 1.504(12) . ?
C33 H33A 0.99 . ?
C33 H33B 0.99 . ?
C34 H34A 0.98 . ?
C34 H34B 0.98 . ?
C34 H34C 0.98 . ?
C35 C36 1.504(11) . ?
C35 H35A 0.99 . ?
C35 H35B 0.99 . ?
C36 H36A 0.98 . ?
C36 H36B 0.98 . ?
C36 H36C 0.98 . ?
C37 C38 1.519(10) . ?
C37 H37A 0.99 . ?
C37 H37B 0.99 . ?
C38 H38A 0.98 . ?
C38 H38B 0.98 . ?
C38 H38C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.3(8) . . ?
C6 C1 I1 118.9(7) . . ?
C2 C1 I1 122.8(5) . . ?
C3 C2 C1 119.6(7) . . ?
C3 C2 I2 117.4(6) . . ?
C1 C2 I2 123.0(6) . . ?
F3A C3 C4 117.0(8) . . ?
F3A C3 C2 121.5(7) . . ?
C4 C3 C2 121.5(8) . . ?
F4A C4 C3 121.4(8) . . ?
F4A C4 C5 120.3(7) . . ?
C3 C4 C5 118.2(8) . . ?
F5A C5 C6 120.1(8) . . ?
F5A C5 C4 118.8(8) . . ?
C6 C5 C4 121.1(7) . . ?
F6A C6 C5 118.4(7) . . ?
F6A C6 C1 120.3(8) . . ?
C5 C6 C1 121.3(8) . . ?
C16 C11 C12 119.3(7) . . ?
C16 C11 I11 119.8(6) . . ?
C12 C11 I11 120.9(6) . . ?
C13 C12 C11 118.5(7) . . ?
C13 C12 I12 116.5(6) . . ?
C11 C12 I12 124.9(6) . . ?
F13A C13 C14 117.5(7) . . ?
F13A C13 C12 121.9(8) . . ?
C14 C13 C12 120.7(8) . . ?
F14A C14 C15 118.2(8) . . ?
F14A C14 C13 120.7(8) . . ?
C15 C14 C13 121.1(7) . . ?
F15A C15 C14 121.1(7) . . ?
F15A C15 C16 119.9(8) . . ?
C14 C15 C16 118.9(8) . . ?
F16A C16 C11 120.9(7) . . ?
F16A C16 C15 117.6(8) . . ?
C11 C16 C15 121.5(8) . . ?
N23 C22 S21 179.6(8) . . ?
C37 N31 C35 111.9(6) . . ?
C37 N31 C31 106.3(5) . . ?
C35 N31 C31 111.0(6) . . ?
C37 N31 C33 110.4(6) . . ?
C35 N31 C33 106.6(6) . . ?
C31 N31 C33 110.7(5) . . ?
C32 C31 N31 114.8(6) . . ?
C32 C31 H31A 108.6 . . ?
N31 C31 H31A 108.6 . . ?
C32 C31 H31B 108.6 . . ?
N31 C31 H31B 108.6 . . ?
H31A C31 H31B 107.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 N31 116.2(6) . . ?
C34 C33 H33A 108.2 . . ?
N31 C33 H33A 108.2 . . ?
C34 C33 H33B 108.2 . . ?
N31 C33 H33B 108.2 . . ?
H33A C33 H33B 107.4 . . ?
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 . . ?
C36 C35 N31 115.3(6) . . ?
C36 C35 H35A 108.5 . . ?
N31 C35 H35A 108.5 . . ?
C36 C35 H35B 108.5 . . ?
N31 C35 H35B 108.5 . . ?
H35A C35 H35B 107.5 . . ?
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 . . ?
N31 C37 C38 114.7(6) . . ?
N31 C37 H37A 108.6 . . ?
C38 C37 H37A 108.6 . . ?
N31 C37 H37B 108.6 . . ?
C38 C37 H37B 108.6 . . ?
H37A C37 H37B 107.6 . . ?
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 . . ?

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 -0.3(9) . . . . ?
I1 C1 C2 C3 -178.6(5) . . . . ?
C6 C1 C2 I2 177.5(5) . . . . ?
I1 C1 C2 I2 -0.9(7) . . . . ?
C1 C2 C3 F3A -179.2(6) . . . . ?
I2 C2 C3 F3A 2.9(8) . . . . ?
C1 C2 C3 C4 -0.2(10) . . . . ?
I2 C2 C3 C4 -178.1(5) . . . . ?
F3A C3 C4 F4A -3.0(9) . . . . ?
C2 C3 C4 F4A 178.0(6) . . . . ?
F3A C3 C4 C5 -179.7(6) . . . . ?
C2 C3 C4 C5 1.2(10) . . . . ?
F4A C4 C5 F5A 1.2(9) . . . . ?
C3 C4 C5 F5A 178.0(6) . . . . ?
F4A C4 C5 C6 -178.6(6) . . . . ?
C3 C4 C5 C6 -1.8(10) . . . . ?
F5A C5 C6 F6A -0.1(10) . . . . ?
C4 C5 C6 F6A 179.8(6) . . . . ?
F5A C5 C6 C1 -178.4(6) . . . . ?
C4 C5 C6 C1 1.4(11) . . . . ?
C2 C1 C6 F6A -178.6(6) . . . . ?
I1 C1 C6 F6A -0.2(9) . . . . ?
C2 C1 C6 C5 -0.3(10) . . . . ?
I1 C1 C6 C5 178.1(5) . . . . ?
C16 C11 C12 C13 0.6(9) . . . . ?
I11 C11 C12 C13 -178.2(5) . . . . ?
C16 C11 C12 I12 -180.0(5) . . . . ?
I11 C11 C12 I12 1.2(8) . . . . ?
C11 C12 C13 F13A 179.5(6) . . . . ?
I12 C12 C13 F13A 0.1(8) . . . . ?
C11 C12 C13 C14 -0.7(9) . . . . ?
I12 C12 C13 C14 179.9(5) . . . . ?
F13A C13 C14 F14A 1.6(9) . . . . ?
C12 C13 C14 F14A -178.2(6) . . . . ?
F13A C13 C14 C15 -179.7(6) . . . . ?
C12 C13 C14 C15 0.5(10) . . . . ?
F14A C14 C15 F15A 2.1(9) . . . . ?
C13 C14 C15 F15A -176.7(6) . . . . ?
F14A C14 C15 C16 178.5(6) . . . . ?
C13 C14 C15 C16 -0.3(10) . . . . ?
C12 C11 C16 F16A 178.6(6) . . . . ?
I11 C11 C16 F16A -2.6(9) . . . . ?
C12 C11 C16 C15 -0.4(10) . . . . ?
I11 C11 C16 C15 178.4(5) . . . . ?
F15A C15 C16 F16A -2.4(9) . . . . ?
C14 C15 C16 F16A -178.8(6) . . . . ?
F15A C15 C16 C11 176.7(6) . . . . ?
C14 C15 C16 C11 0.3(10) . . . . ?
C37 N31 C31 C32 179.1(8) . . . . ?
C35 N31 C31 C32 -59.0(9) . . . . ?
C33 N31 C31 C32 59.3(10) . . . . ?
C37 N31 C33 C34 -58.7(8) . . . . ?
C35 N31 C33 C34 179.6(6) . . . . ?
C31 N31 C33 C34 58.7(8) . . . . ?
C37 N31 C35 C36 61.4(8) . . . . ?
C31 N31 C35 C36 -57.2(7) . . . . ?
C33 N31 C35 C36 -177.8(6) . . . . ?
C35 N31 C37 C38 57.9(9) . . . . ?
C31 N31 C37 C38 179.3(7) . . . . ?
C33 N31 C37 C38 -60.7(9) . . . . ?

# Attachment '2a_PC3S.cif'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2008-05-19 at 12:02:38
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:\progs\wingx\files\archive.dat
# CIF files read : job struct

data_job2
_database_code_depnum_ccdc_archive 'CCDC 739581'

_audit_creation_date             2008-05-19T12:02:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
tetraethylammonium thiocyanate, 1,3-diiodotetrafluorobenzene
;
_chemical_formula_moiety         'C6 F4 I2, S C N, N C8 H20'
_chemical_formula_sum            'C15 H20 F4 I2 N2 S'
_chemical_formula_weight         590.19
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.7404(8)
_cell_length_b                   22.8074(10)
_cell_length_c                   12.1785(6)
_cell_angle_alpha                90
_cell_angle_beta                 126.2590(10)
_cell_angle_gamma                90
_cell_volume                     3973.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5115
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      27.46
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_exptl_crystal_density_diffrn    1.973
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2256
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.306
_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  0.245
_exptl_absorpt_correction_T_max  0.396

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_number            17224
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.954
_reflns_number_total             4356
_reflns_number_gt                4083
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_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)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0219P)²+5.5186P] 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_number_reflns         4356
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0216
_refine_ls_wR_factor_ref         0.0544
_refine_ls_wR_factor_gt          0.0531
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.784
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.106

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.85737(16) 0.16641(10) 0.1502(2) 0.0150(5) Uani 1 d . . .
I1 I 0.826151(10) 0.246073(7) 0.202269(15) 0.01504(5) Uani 1 d . . .
C2 C 0.83208(17) 0.11303(11) 0.1740(3) 0.0166(5) Uani 1 d . . .
F2 F 0.78552(11) 0.11334(6) 0.23074(16) 0.0212(3) Uani 1 d . . .
I3 I 0.812474(11) -0.019558(7) 0.185701(16) 0.01962(6) Uani 1 d . . .
C3 C 0.85275(17) 0.05917(10) 0.1448(2) 0.0163(5) Uani 1 d . . .
C4 C 0.90156(17) 0.05971(11) 0.0879(2) 0.0172(5) Uani 1 d . . .
F4 F 0.92552(11) 0.00937(7) 0.05957(16) 0.0240(3) Uani 1 d . . .
C5 C 0.92767(17) 0.11169(11) 0.0613(2) 0.0170(5) Uani 1 d . . .
F5 F 0.97595(11) 0.11157(6) 0.00807(16) 0.0233(3) Uani 1 d . . .
C6 C 0.90478(16) 0.16458(11) 0.0914(2) 0.0161(5) Uani 1 d . . .
F6 F 0.93152(10) 0.21431(6) 0.06472(15) 0.0207(3) Uani 1 d . . .
S11 S 0.73763(5) 0.86340(3) 0.23537(7) 0.02494(15) Uani 1 d . . .
C12 C 0.6429(2) 0.87264(11) 0.0799(3) 0.0243(6) Uani 1 d . . .
N13 N 0.5746(2) 0.88105(12) -0.0299(3) 0.0394(7) Uani 1 d . . .
N21A N 0.5 0.72350(13) 0.75 0.0211(6) Uani 0.25 d SP . 1
C22A C 0.5646(4) 0.7780(2) 0.7827(5) 0.0188(10) Uani 0.5 d P . 1
H22A H 0.5242 0.8132 0.7463 0.023 Uiso 0.5 calc PR . 1
H22B H 0.6072 0.7823 0.8829 0.023 Uiso 0.5 calc PR . 1
C23A C 0.6195(2) 0.77845(13) 0.7342(3) 0.0322(7) Uani 0.5 d P A 1
H23A H 0.6858 0.7781 0.8115 0.048 Uiso 0.5 calc PR A 1
H23B H 0.6057 0.8139 0.6798 0.048 Uiso 0.5 calc PR A 1
H23C H 0.6052 0.7437 0.6777 0.048 Uiso 0.5 calc PR A 1
N21B N 0.5 0.72350(13) 0.75 0.0211(6) Uani 0.25 d SP . 2
C22B C 0.5444(4) 0.7302(3) 0.6826(6) 0.0248(12) Uani 0.5 d P B 2
H22C H 0.4948 0.7377 0.585 0.03 Uiso 0.5 calc PR B 2
H22D H 0.5737 0.6922 0.6886 0.03 Uiso 0.5 calc PR B 2
C23B C 0.6195(2) 0.77845(13) 0.7342(3) 0.0322(7) Uani 0.5 d P B 2
H23D H 0.6434 0.7781 0.6795 0.048 Uiso 0.5 calc PR B 2
H23E H 0.6709 0.7711 0.8299 0.048 Uiso 0.5 calc PR B 2
H23F H 0.5916 0.8168 0.726 0.048 Uiso 0.5 calc PR B 2
N21C N 0.5 0.72350(13) 0.75 0.0211(6) Uani 0.25 d SP . 3
C32C C 0.5622(4) 0.7168(2) 0.9010(5) 0.0204(10) Uani 0.5 d P C 3
H32A H 0.5235 0.706 0.9321 0.024 Uiso 0.5 calc PR C 3
H32B H 0.5919 0.7551 0.9426 0.024 Uiso 0.5 calc PR C 3
C33C C 0.6409(2) 0.66940(14) 0.9536(3) 0.0355(7) Uani 0.5 d P C 3
H33A H 0.6789 0.6673 1.0532 0.053 Uiso 0.5 calc PR C 3
H33B H 0.6807 0.6803 0.9256 0.053 Uiso 0.5 calc PR C 3
H33C H 0.6121 0.6311 0.9148 0.053 Uiso 0.5 calc PR C 3
N21D N 0.5 0.72350(13) 0.75 0.0211(6) Uani 0.25 d SP . 4
C32D C 0.5659(4) 0.6686(2) 0.8077(5) 0.0238(11) Uani 0.5 d P . 4
H32C H 0.5272 0.6333 0.7873 0.029 Uiso 0.5 calc PR . 4
H32D H 0.5944 0.6646 0.7585 0.029 Uiso 0.5 calc PR . 4
C33D C 0.6409(2) 0.66940(14) 0.9536(3) 0.0355(7) Uani 0.5 d P D 4
H33D H 0.7015 0.669 0.9683 0.053 Uiso 0.5 calc PR D 4
H33E H 0.6357 0.6348 0.9965 0.053 Uiso 0.5 calc PR D 4
H33F H 0.6358 0.705 0.994 0.053 Uiso 0.5 calc PR D 4
N51 N 0.5 0.94832(13) 0.25 0.0171(6) Uani 1 d S . .
C51 C 0.5226(2) 0.98616(11) 0.1694(3) 0.0220(5) Uani 1 d . . .
H51A H 0.5352 0.9599 0.1171 0.026 Uiso 1 calc R . .
H51B H 0.4667 1.0098 0.1029 0.026 Uiso 1 calc R . .
C52 C 0.6052(2) 1.02729(13) 0.2539(3) 0.0304(6) Uani 1 d . . .
H52A H 0.5944 1.0531 0.3077 0.046 Uiso 1 calc R . .
H52B H 0.6123 1.051 0.1935 0.046 Uiso 1 calc R . .
H52C H 0.6621 1.0043 0.3152 0.046 Uiso 1 calc R . .
C61 C 0.58480(18) 0.91105(11) 0.3498(3) 0.0202(5) Uani 1 d . . .
H61A H 0.6356 0.9372 0.4189 0.024 Uiso 1 calc R . .
H61B H 0.6063 0.8918 0.3 0.024 Uiso 1 calc R . .
C62 C 0.5691(2) 0.86375(12) 0.4233(3) 0.0229(5) Uani 1 d . . .
H62A H 0.5492 0.8822 0.475 0.034 Uiso 1 calc R . .
H62B H 0.6275 0.8422 0.4858 0.034 Uiso 1 calc R . .
H62C H 0.5206 0.8365 0.3564 0.034 Uiso 1 calc R . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 1.386(3) . ?
C1 C6 1.390(3) . ?
C1 I1 2.104(2) . ?
C2 F2 1.355(3) . ?
C2 C3 1.387(3) . ?
I3 C3 2.098(2) . ?
C3 C4 1.393(3) . ?
C4 F4 1.338(3) . ?
C4 C5 1.379(3) . ?
C5 F5 1.346(3) . ?
C5 C6 1.390(3) . ?
C6 F6 1.342(3) . ?
S11 C12 1.640(3) . ?
C12 N13 1.173(4) . ?
N21A C22A 1.573(5) . ?
N21A C22A 1.573(5) 2_656 ?
C22A C23A 1.406(5) . ?
C22A C22A 1.929(10) 2_656 ?
C22A H22A 0.99 . ?
C22A H22B 0.99 . ?
C23A H23A 0.98 . ?
C23A H23B 0.98 . ?
C23A H23C 0.98 . ?
C22B H22C 0.99 . ?
C22B H22D 0.99 . ?
C32C C33C 1.572(6) . ?
C32C H32A 0.99 . ?
C32C H32B 0.99 . ?
C33C H33A 0.98 . ?
C33C H33B 0.98 . ?
C33C H33C 0.98 . ?
C32D C32D 1.886(11) 2_656 ?
C32D H32C 0.99 . ?
C32D H32D 0.99 . ?
N51 C61 1.516(3) 2_655 ?
N51 C61 1.516(3) . ?
N51 C51 1.529(3) . ?
N51 C51 1.529(3) 2_655 ?
C51 C52 1.517(4) . ?
C51 H51A 0.99 . ?
C51 H51B 0.99 . ?
C52 H52A 0.98 . ?
C52 H52B 0.98 . ?
C52 H52C 0.98 . ?
C61 C62 1.529(3) . ?
C61 H61A 0.99 . ?
C61 H61B 0.99 . ?
C62 H62A 0.98 . ?
C62 H62B 0.98 . ?
C62 H62C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 116.8(2) . . ?
C2 C1 I1 121.34(16) . . ?
C6 C1 I1 121.89(17) . . ?
F2 C2 C1 118.2(2) . . ?
F2 C2 C3 118.0(2) . . ?
C1 C2 C3 123.8(2) . . ?
C2 C3 C4 117.1(2) . . ?
C2 C3 I3 121.22(16) . . ?
C4 C3 I3 121.65(18) . . ?
F4 C4 C5 118.4(2) . . ?
F4 C4 C3 120.4(2) . . ?
C5 C4 C3 121.2(2) . . ?
F5 C5 C4 120.6(2) . . ?
F5 C5 C6 119.9(2) . . ?
C4 C5 C6 119.6(2) . . ?
F6 C6 C5 117.99(19) . . ?
F6 C6 C1 120.5(2) . . ?
C5 C6 C1 121.5(2) . . ?
N13 C12 S11 177.7(3) . . ?
C22A N21A C22A 75.7(4) . 2_656 ?
C23A C22A N21A 118.8(4) . . ?
C23A C22A C22A 140.8(5) . 2_656 ?
N21A C22A C22A 52.17(19) . 2_656 ?
C23A C22A H22A 107.6 . . ?
N21A C22A H22A 107.6 . . ?
C22A C22A H22A 56.5 2_656 . ?
C23A C22A H22B 107.6 . . ?
N21A C22A H22B 107.6 . . ?
C22A C22A H22B 111.4 2_656 . ?
H22A C22A H22B 107.1 . . ?
C22A C23A H23A 109.5 . . ?
C22A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C22A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
H22C C22B H22D 107.1 . . ?
C33C C32C H32A 108.8 . . ?
C33C C32C H32B 108.8 . . ?
H32A C32C H32B 107.7 . . ?
C32C C33C H33A 109.5 . . ?
C32C C33C H33B 109.5 . . ?
H33A C33C H33B 109.5 . . ?
C32C C33C H33C 109.5 . . ?
H33A C33C H33C 109.5 . . ?
H33B C33C H33C 109.5 . . ?
C32D C32D H32C 56.1 2_656 . ?
C32D C32D H32D 113.6 2_656 . ?
H32C C32D H32D 107.4 . . ?
C61 N51 C61 111.8(3) 2_655 . ?
C61 N51 C51 108.35(14) 2_655 . ?
C61 N51 C51 108.54(14) . . ?
C61 N51 C51 108.54(14) 2_655 2_655 ?
C61 N51 C51 108.35(14) . 2_655 ?
C51 N51 C51 111.3(3) . 2_655 ?
C52 C51 N51 115.3(2) . . ?
C52 C51 H51A 108.4 . . ?
N51 C51 H51A 108.4 . . ?
C52 C51 H51B 108.4 . . ?
N51 C51 H51B 108.4 . . ?
H51A C51 H51B 107.5 . . ?
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 . . ?
N51 C61 C62 115.3(2) . . ?
N51 C61 H61A 108.5 . . ?
C62 C61 H61A 108.5 . . ?
N51 C61 H61B 108.5 . . ?
C62 C61 H61B 108.5 . . ?
H61A C61 H61B 107.5 . . ?
C61 C62 H62A 109.5 . . ?
C61 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
C61 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 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 F2 -179.8(2) . . . . ?
I1 C1 C2 F2 0.7(3) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
I1 C1 C2 C3 -178.40(19) . . . . ?
F2 C2 C3 C4 -179.3(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
F2 C2 C3 I3 0.5(3) . . . . ?
C1 C2 C3 I3 179.53(19) . . . . ?
C2 C3 C4 F4 178.7(2) . . . . ?
I3 C3 C4 F4 -1.1(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
I3 C3 C4 C5 179.96(19) . . . . ?
F4 C4 C5 F5 0.1(4) . . . . ?
C3 C4 C5 F5 179.1(2) . . . . ?
F4 C4 C5 C6 -179.1(2) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
F5 C5 C6 F6 0.6(3) . . . . ?
C4 C5 C6 F6 179.8(2) . . . . ?
F5 C5 C6 C1 -178.1(2) . . . . ?
C4 C5 C6 C1 1.1(4) . . . . ?
C2 C1 C6 F6 179.8(2) . . . . ?
I1 C1 C6 F6 -0.7(3) . . . . ?
C2 C1 C6 C5 -1.6(4) . . . . ?
I1 C1 C6 C5 177.95(19) . . . . ?
C22A N21A C22A C23A -133.8(6) 2_656 . . . ?
C61 N51 C51 C52 178.9(2) 2_655 . . . ?
C61 N51 C51 C52 -59.5(3) . . . . ?
C51 N51 C51 C52 59.65(19) 2_655 . . . ?
C61 N51 C61 C62 -51.50(18) 2_655 . . . ?
C51 N51 C61 C62 -171.0(2) . . . . ?
C51 N51 C61 C62 68.1(3) 2_655 . . . ?

# Attachment '3a_PC29.cif'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2007-12-19 at 18:36:19
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:\progs\wingx\files\archive.dat
# CIF files read : job struct

data_job3
_database_code_depnum_ccdc_archive 'CCDC 739582'

_audit_creation_date             2007-12-19T18:36:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
Bis(tetraethylammonium thiocyanate), 1,4-diiodotetrafluorobenzene
;
_chemical_formula_moiety         '5(C6 F4 I2), 2(C S N), 2(C8 N H20)'
_chemical_formula_sum            'C48 H40 F20 I10 N4 S2'
_chemical_formula_weight         2385.96
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 2/a'
_symmetry_space_group_name_Hall  '-P 2ya'
_symmetry_Int_Tables_number      13
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'-x, -y, -z'
'x-1/2, -y, z'

_cell_length_a                   16.4673(12)
_cell_length_b                   16.4260(14)
_cell_length_c                   24.711(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.847(3)
_cell_angle_gamma                90
_cell_volume                     6680.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9025
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.47
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    2.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4392
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.793
_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  0.140
_exptl_absorpt_correction_T_max  0.443

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_number            67743
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.44
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.973
_reflns_number_total             14927
_reflns_number_gt                12218
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_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)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0000P)²+274.2773P] 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_number_reflns         14927
_refine_ls_number_parameters     757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1542
_refine_ls_wR_factor_gt          0.1496
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_restrained_S_all      1.216
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         3.593
_refine_diff_density_min         -1.631
_refine_diff_density_rms         0.263

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.52310(5) 0.07624(5) 0.62350(3) 0.02044(17) Uani 1 1 d . . .
C1 C 0.5208(8) 0.0956(7) 0.5403(4) 0.019(2) Uani 1 1 d . . .
C2 C 0.5905(8) 0.1022(8) 0.5120(5) 0.023(3) Uani 1 1 d . . .
F2 F 0.6633(5) 0.0927(5) 0.5371(3) 0.0314(18) Uani 1 1 d . . .
C3 C 0.5887(7) 0.1225(7) 0.4569(5) 0.020(2) Uani 1 1 d . . .
F3 F 0.6596(5) 0.1295(5) 0.4320(3) 0.0299(17) Uani 1 1 d . . .
C4 C 0.5165(9) 0.1343(7) 0.4299(5) 0.026(3) Uani 1 1 d . . .
I4 I 0.51150(5) 0.16917(5) 0.34713(3) 0.02266(17) Uani 1 1 d . . .
C5 C 0.4463(8) 0.1263(7) 0.4576(5) 0.023(3) Uani 1 1 d . . .
F5 F 0.3729(5) 0.1377(5) 0.4322(3) 0.0284(17) Uani 1 1 d . . .
C6 C 0.4476(7) 0.1071(7) 0.5120(5) 0.020(2) Uani 1 1 d . . .
F6 F 0.3760(4) 0.0989(5) 0.5367(3) 0.0282(17) Uani 1 1 d . . .
C11 C 0.4817(7) 0.4021(7) 0.0360(4) 0.016(2) Uani 1 1 d . . .
I11 I 0.48915(5) 0.42144(5) 0.11963(3) 0.01847(16) Uani 1 1 d . . .
C12 C 0.5522(7) 0.3909(7) 0.0085(5) 0.020(2) Uani 1 1 d . . .
F12 F 0.6256(4) 0.3959(5) 0.0335(3) 0.0269(16) Uani 1 1 d . . .
C13 C 0.5477(8) 0.3727(7) -0.0466(5) 0.021(2) Uani 1 1 d . . .
F13 F 0.6201(4) 0.3623(5) -0.0711(3) 0.0276(17) Uani 1 1 d . . .
C14 C 0.4771(8) 0.3656(7) -0.0752(4) 0.020(3) Uani 1 1 d . . .
I14 I 0.47685(5) 0.33457(5) -0.15764(3) 0.02110(17) Uani 1 1 d . . .
C15 C 0.4064(7) 0.3783(7) -0.0480(5) 0.018(2) Uani 1 1 d . . .
F15 F 0.3327(5) 0.3730(5) -0.0733(3) 0.0291(17) Uani 1 1 d . . .
C16 C 0.4088(7) 0.3962(7) 0.0071(5) 0.019(2) Uani 1 1 d . . .
F17 F 0.3386(5) 0.4070(5) 0.0322(3) 0.0289(17) Uani 1 1 d . . .
C21 C 0.5013(8) 0.4833(7) 0.4442(5) 0.021(2) Uani 1 1 d . . .
I21 I 0.50595(5) 0.45028(5) 0.36220(3) 0.01981(16) Uani 1 1 d . . .
C22 C 0.4291(7) 0.4882(7) 0.4705(5) 0.019(2) Uani 1 1 d . . .
F22 F 0.3585(4) 0.4775(4) 0.4431(3) 0.0235(15) Uani 1 1 d . . .
C26 C 0.5727(7) 0.4949(7) 0.4746(5) 0.017(2) Uani 1 1 d . . .
F26 F 0.6457(4) 0.4894(5) 0.4517(3) 0.0255(16) Uani 1 1 d . . .
C31 C 0.3015(7) 0.3005(7) 0.5469(5) 0.018(2) Uani 1 1 d . . .
I31 I 0.37717(5) 0.29378(5) 0.61626(3) 0.02179(17) Uani 1 1 d . . .
C32 C 0.3337(7) 0.3018(7) 0.4951(5) 0.019(2) Uani 1 1 d . . .
F32 F 0.4142(4) 0.3018(5) 0.4894(3) 0.0269(16) Uani 1 1 d . . .
C36 C 0.2168(7) 0.3020(7) 0.5510(5) 0.018(2) Uani 1 1 d . . .
F36 F 0.1833(4) 0.3017(5) 0.5994(3) 0.0257(16) Uani 1 1 d . . .
C41 C 0.4953(8) 0.9810(7) 0.0555(5) 0.018(2) Uani 1 1 d . . .
I41 I 0.48919(5) 0.94658(5) 0.13679(3) 0.02310(17) Uani 1 1 d . . .
F41 F 0.6404(4) 0.9819(5) 0.0596(3) 0.0271(16) Uani 1 1 d . . .
C42 C 0.5704(7) 0.9906(7) 0.0320(4) 0.017(2) Uani 1 1 d . . .
C46 C 0.4268(7) 0.9905(7) 0.0235(5) 0.019(2) Uani 1 1 d . . .
F46 F 0.3529(4) 0.9824(5) 0.0445(3) 0.0266(16) Uani 1 1 d . . .
C51 C 0.7979(8) 0.1985(7) 0.9545(5) 0.022(3) Uani 1 1 d . . .
I51 I 0.87270(5) 0.20391(5) 0.88658(3) 0.02454(18) Uani 1 1 d . . .
C52 C 0.7147(8) 0.1974(7) 0.9484(6) 0.025(3) Uani 1 1 d . . .
F52 F 0.6800(5) 0.1984(5) 0.8992(3) 0.0316(18) Uani 1 1 d . . .
C56 C 0.8333(7) 0.1990(7) 1.0062(6) 0.023(3) Uani 1 1 d . . .
F56 F 0.9137(4) 0.1978(5) 1.0149(3) 0.0309(18) Uani 1 1 d . . .
C61 C 0.3008(7) 0.1927(7) 0.0461(5) 0.018(2) Uani 1 1 d . . .
I2 I 0.37958(5) 0.19849(5) 0.11492(3) 0.02223(17) Uani 1 1 d . . .
C62 C 0.3319(7) 0.1927(7) -0.0056(5) 0.021(2) Uani 1 1 d . . .
F62 F 0.4136(4) 0.1933(4) -0.0119(3) 0.0234(15) Uani 1 1 d . . .
C66 C 0.2175(8) 0.1922(8) 0.0503(5) 0.024(3) Uani 1 1 d . . .
F66 F 0.1846(4) 0.1931(5) 0.0994(3) 0.0269(16) Uani 1 1 d . . .
C71 C 0.8006(7) 0.3090(7) 0.4556(5) 0.019(2) Uani 1 1 d . . .
I71 I 0.87839(5) 0.30206(5) 0.38988(3) 0.02210(17) Uani 1 1 d . . .
C72 C 0.7179(8) 0.3090(7) 0.4484(5) 0.022(3) Uani 1 1 d . . .
F72 F 0.6851(5) 0.3093(5) 0.3978(3) 0.0288(17) Uani 1 1 d . . .
C76 C 0.8319(7) 0.3096(7) 0.5088(5) 0.021(2) Uani 1 1 d . . .
F76 F 0.9134(4) 0.3089(5) 0.5184(3) 0.0262(16) Uani 1 1 d . . .
S81 S 0.5091(2) 0.2162(2) 0.22096(12) 0.0257(7) Uani 1 1 d . . .
C81 C 0.5157(7) 0.3152(8) 0.2371(5) 0.022(3) Uani 1 1 d . . .
N82 N 0.5200(7) 0.3830(7) 0.2468(4) 0.024(2) Uani 1 1 d . . .
S91 S 0.50708(19) 0.2854(2) 0.71886(12) 0.0218(6) Uani 1 1 d . . .
C91 C 0.5243(7) 0.1892(8) 0.7375(5) 0.021(2) Uani 1 1 d . . .
N92 N 0.5366(7) 0.1217(7) 0.7499(4) 0.029(3) Uani 1 1 d . . .
N101 N 0.2595(6) 0.5134(6) 0.2374(4) 0.018(2) Uani 1 1 d . . .
C101 C 0.3223(7) 0.4461(8) 0.2324(5) 0.022(3) Uani 1 1 d . . .
H10A H 0.3547 0.4573 0.2002 0.027 Uiso 1 1 calc R . .
H10B H 0.3597 0.4484 0.2646 0.027 Uiso 1 1 calc R . .
C102 C 0.2884(10) 0.3606(9) 0.2276(7) 0.040(4) Uani 1 1 d . . .
H10C H 0.3331 0.3218 0.2245 0.061 Uiso 1 1 calc R . .
H10D H 0.2523 0.3569 0.1954 0.061 Uiso 1 1 calc R . .
H10E H 0.2577 0.3478 0.2599 0.061 Uiso 1 1 calc R . .
C103 C 0.2053(9) 0.5160(9) 0.1858(5) 0.028(3) Uani 1 1 d . . .
H10F H 0.1788 0.4623 0.1812 0.034 Uiso 1 1 calc R . .
H10G H 0.1619 0.5567 0.191 0.034 Uiso 1 1 calc R . .
C104 C 0.2478(8) 0.5365(10) 0.1340(6) 0.033(3) Uani 1 1 d . . .
H10H H 0.2081 0.5364 0.1036 0.05 Uiso 1 1 calc R . .
H10I H 0.29 0.4959 0.1276 0.05 Uiso 1 1 calc R . .
H10J H 0.2727 0.5905 0.1374 0.05 Uiso 1 1 calc R . .
C105 C 0.3076(8) 0.5917(8) 0.2441(5) 0.024(3) Uani 1 1 d . . .
H10K H 0.3422 0.5875 0.2775 0.028 Uiso 1 1 calc R . .
H10L H 0.3442 0.5969 0.2132 0.028 Uiso 1 1 calc R . .
C106 C 0.2572(10) 0.6686(9) 0.2473(7) 0.039(4) Uani 1 1 d . . .
H10M H 0.2933 0.7157 0.2517 0.059 Uiso 1 1 calc R . .
H10N H 0.2218 0.6651 0.2782 0.059 Uiso 1 1 calc R . .
H10O H 0.224 0.6747 0.2139 0.059 Uiso 1 1 calc R . .
C107 C 0.2043(7) 0.4986(8) 0.2838(5) 0.023(3) Uani 1 1 d . . .
H10P H 0.1734 0.4477 0.2768 0.027 Uiso 1 1 calc R . .
H10Q H 0.1646 0.5437 0.2853 0.027 Uiso 1 1 calc R . .
C108 C 0.2482(8) 0.4917(9) 0.3383(5) 0.026(3) Uani 1 1 d . . .
H10R H 0.2086 0.4824 0.3664 0.039 Uiso 1 1 calc R . .
H10S H 0.2779 0.5423 0.3461 0.039 Uiso 1 1 calc R . .
H10T H 0.2865 0.4461 0.3377 0.039 Uiso 1 1 calc R . .
N111 N 0.2690(6) 0.0236(6) 0.7355(4) 0.018(2) Uani 1 1 d . . .
C111 C 0.3308(8) 0.0911(8) 0.7463(6) 0.028(3) Uani 1 1 d . . .
H11A H 0.3688 0.0925 0.7161 0.034 Uiso 1 1 calc R . .
H11B H 0.3627 0.0778 0.7798 0.034 Uiso 1 1 calc R . .
C112 C 0.2935(10) 0.1755(9) 0.7525(7) 0.042(4) Uani 1 1 d . . .
H11C H 0.3368 0.2155 0.7593 0.064 Uiso 1 1 calc R . .
H11D H 0.2568 0.1753 0.7829 0.064 Uiso 1 1 calc R . .
H11E H 0.263 0.1899 0.7192 0.064 Uiso 1 1 calc R . .
C113 C 0.2215(8) 0.0369(10) 0.6831(5) 0.034(3) Uani 1 1 d . . .
H11F H 0.1892 0.0874 0.6864 0.041 Uiso 1 1 calc R . .
H11G H 0.1827 -0.0087 0.6779 0.041 Uiso 1 1 calc R . .
C114 C 0.2720(10) 0.0438(11) 0.6325(6) 0.047(5) Uani 1 1 d . . .
H11H H 0.2359 0.0523 0.6007 0.07 Uiso 1 1 calc R . .
H11I H 0.303 -0.0065 0.6279 0.07 Uiso 1 1 calc R . .
H11J H 0.3095 0.0899 0.6364 0.07 Uiso 1 1 calc R . .
C115 C 0.2077(7) 0.0191(8) 0.7806(6) 0.026(3) Uani 1 1 d . . .
H11K H 0.1754 0.07 0.7802 0.031 Uiso 1 1 calc R . .
H11L H 0.1698 -0.0265 0.7727 0.031 Uiso 1 1 calc R . .
C116 C 0.2451(9) 0.0073(10) 0.8365(6) 0.038(4) Uani 1 1 d . . .
H11M H 0.2021 0.0051 0.863 0.057 Uiso 1 1 calc R . .
H11N H 0.2816 0.053 0.8453 0.057 Uiso 1 1 calc R . .
H11O H 0.276 -0.0437 0.8377 0.057 Uiso 1 1 calc R . .
C117 C 0.3187(9) -0.0540(8) 0.7328(7) 0.040(4) Uani 1 1 d . . .
H11P H 0.3589 -0.0472 0.7042 0.048 Uiso 1 1 calc R . .
H11Q H 0.3493 -0.0604 0.7677 0.048 Uiso 1 1 calc R . .
C118 C 0.2726(13) -0.1311(11) 0.7217(12) 0.085(9) Uani 1 1 d . . .
H11R H 0.3106 -0.1769 0.7207 0.127 Uiso 1 1 calc R . .
H11S H 0.2431 -0.1267 0.6867 0.127 Uiso 1 1 calc R . .
H11T H 0.2338 -0.1401 0.7503 0.127 Uiso 1 1 calc R . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 2.080(11) . ?
C1 C2 1.367(18) . ?
C1 C6 1.385(17) . ?
C2 F2 1.343(14) . ?
C2 C3 1.399(17) . ?
C3 F3 1.343(14) . ?
C3 C4 1.358(18) . ?
C4 C5 1.367(19) . ?
C4 I4 2.124(12) . ?
C5 F5 1.357(15) . ?
C5 C6 1.381(16) . ?
C6 F6 1.352(14) . ?
C11 C12 1.377(16) . ?
C11 C16 1.380(16) . ?
C11 I11 2.090(10) . ?
C12 F12 1.343(13) . ?
C12 C13 1.394(16) . ?
C13 C14 1.345(18) . ?
C13 F13 1.365(14) . ?
C14 C15 1.379(17) . ?
C14 I14 2.100(11) . ?
C15 F15 1.349(14) . ?
C15 C16 1.393(16) . ?
C16 F17 1.341(14) . ?
C21 C22 1.376(18) . ?
C21 C26 1.389(16) . ?
C21 I21 2.100(12) . ?
C22 F22 1.338(13) . ?
C22 C26 1.387(16) 3_666 ?
C26 F26 1.347(14) . ?
C26 C22 1.387(16) 3_666 ?
C31 C32 1.401(17) . ?
C31 C36 1.402(16) . ?
C31 I31 2.089(11) . ?
C32 F32 1.339(13) . ?
C32 C36 1.387(16) 2_556 ?
C36 F36 1.335(14) . ?
C36 C32 1.387(16) 2_556 ?
C41 C46 1.367(17) . ?
C41 C42 1.392(17) . ?
C41 I41 2.092(11) . ?
F41 C42 1.327(12) . ?
C42 C46 1.406(16) 3_675 ?
C46 F46 1.344(13) . ?
C46 C42 1.406(16) 3_675 ?
C51 C52 1.374(18) . ?
C51 C56 1.385(18) . ?
C51 I51 2.116(12) . ?
C52 F52 1.325(15) . ?
C52 C56 1.395(19) 2_657 ?
C56 F56 1.334(14) . ?
C56 C52 1.395(19) 2_657 ?
C61 C66 1.379(17) . ?
C61 C62 1.393(17) . ?
C61 I2 2.107(11) . ?
C62 C66 1.351(18) 2 ?
C62 F62 1.359(13) . ?
C66 F66 1.344(14) . ?
C66 C62 1.351(18) 2 ?
C71 C72 1.367(18) . ?
C71 C76 1.398(16) . ?
C71 I71 2.104(11) . ?
C72 F72 1.345(14) . ?
C72 C76 1.359(17) 2_656 ?
C76 F76 1.355(13) . ?
C76 C72 1.359(17) 2_656 ?
S81 C81 1.677(14) . ?
C81 N82 1.142(17) . ?
S91 C91 1.667(13) . ?
C91 N92 1.167(17) . ?
N101 C107 1.508(15) . ?
N101 C105 1.517(15) . ?
N101 C101 1.520(14) . ?
N101 C103 1.532(15) . ?
C101 C102 1.515(19) . ?
C101 H10A 0.99 . ?
C101 H10B 0.99 . ?
C102 H10C 0.98 . ?
C102 H10D 0.98 . ?
C102 H10E 0.98 . ?
C103 C104 1.516(19) . ?
C103 H10F 0.99 . ?
C103 H10G 0.99 . ?
C104 H10H 0.98 . ?
C104 H10I 0.98 . ?
C104 H10J 0.98 . ?
C105 C106 1.514(19) . ?
C105 H10K 0.99 . ?
C105 H10L 0.99 . ?
C106 H10M 0.98 . ?
C106 H10N 0.98 . ?
C106 H10O 0.98 . ?
C107 C108 1.511(17) . ?
C107 H10P 0.99 . ?
C107 H10Q 0.99 . ?
C108 H10R 0.98 . ?
C108 H10S 0.98 . ?
C108 H10T 0.98 . ?
N111 C113 1.508(16) . ?
N111 C117 1.518(16) . ?
N111 C111 1.522(15) . ?
N111 C115 1.529(15) . ?
C111 C112 1.53(2) . ?
C111 H11A 0.99 . ?
C111 H11B 0.99 . ?
C112 H11C 0.98 . ?
C112 H11D 0.98 . ?
C112 H11E 0.98 . ?
C113 C114 1.53(2) . ?
C113 H11F 0.99 . ?
C113 H11G 0.99 . ?
C114 H11H 0.98 . ?
C114 H11I 0.98 . ?
C114 H11J 0.98 . ?
C115 C116 1.509(19) . ?
C115 H11K 0.99 . ?
C115 H11L 0.99 . ?
C116 H11M 0.98 . ?
C116 H11N 0.98 . ?
C116 H11O 0.98 . ?
C117 C118 1.50(2) . ?
C117 H11P 0.99 . ?
C117 H11Q 0.99 . ?
C118 H11R 0.98 . ?
C118 H11S 0.98 . ?
C118 H11T 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.5(11) . . ?
C2 C1 I1 121.9(9) . . ?
C6 C1 I1 120.5(9) . . ?
F2 C2 C1 120.4(11) . . ?
F2 C2 C3 117.9(11) . . ?
C1 C2 C3 121.6(11) . . ?
F3 C3 C4 121.5(11) . . ?
F3 C3 C2 118.4(11) . . ?
C4 C3 C2 120.1(12) . . ?
C3 C4 C5 118.8(11) . . ?
C3 C4 I4 121.2(10) . . ?
C5 C4 I4 120.0(10) . . ?
F5 C5 C4 120.7(11) . . ?
F5 C5 C6 117.9(12) . . ?
C4 C5 C6 121.4(12) . . ?
F6 C6 C5 118.4(11) . . ?
F6 C6 C1 121.1(10) . . ?
C5 C6 C1 120.5(12) . . ?
C12 C11 C16 117.9(10) . . ?
C12 C11 I11 119.0(8) . . ?
C16 C11 I11 123.0(8) . . ?
F12 C12 C11 121.7(11) . . ?
F12 C12 C13 118.8(11) . . ?
C11 C12 C13 119.5(11) . . ?
C14 C13 F13 120.6(11) . . ?
C14 C13 C12 123.3(11) . . ?
F13 C13 C12 116.1(11) . . ?
C13 C14 C15 117.4(11) . . ?
C13 C14 I14 120.3(9) . . ?
C15 C14 I14 122.3(9) . . ?
F15 C15 C14 121.7(10) . . ?
F15 C15 C16 117.6(10) . . ?
C14 C15 C16 120.7(11) . . ?
F17 C16 C11 120.0(10) . . ?
F17 C16 C15 118.8(11) . . ?
C11 C16 C15 121.1(11) . . ?
C22 C21 C26 117.8(11) . . ?
C22 C21 I21 122.0(9) . . ?
C26 C21 I21 120.0(9) . . ?
F22 C22 C21 120.2(11) . . ?
F22 C22 C26 118.4(11) . 3_666 ?
C21 C22 C26 121.4(11) . 3_666 ?
F26 C26 C22 118.1(10) . 3_666 ?
F26 C26 C21 121.1(11) . . ?
C22 C26 C21 120.8(11) 3_666 . ?
C32 C31 C36 118.1(10) . . ?
C32 C31 I31 121.2(8) . . ?
C36 C31 I31 120.7(9) . . ?
F32 C32 C36 118.9(11) . 2_556 ?
F32 C32 C31 120.0(10) . . ?
C36 C32 C31 121.0(11) 2_556 . ?
F36 C36 C32 118.8(10) . 2_556 ?
F36 C36 C31 120.4(10) . . ?
C32 C36 C31 120.8(11) 2_556 . ?
C46 C41 C42 118.2(10) . . ?
C46 C41 I41 121.5(9) . . ?
C42 C41 I41 120.2(9) . . ?
F41 C42 C41 122.7(10) . . ?
F41 C42 C46 118.0(10) . 3_675 ?
C41 C42 C46 119.3(10) . 3_675 ?
F46 C46 C41 120.3(11) . . ?
F46 C46 C42 117.2(11) . 3_675 ?
C41 C46 C42 122.5(11) . 3_675 ?
C52 C51 C56 119.4(12) . . ?
C52 C51 I51 121.1(10) . . ?
C56 C51 I51 119.5(9) . . ?
F52 C52 C51 120.1(12) . . ?
F52 C52 C56 119.9(12) . 2_657 ?
C51 C52 C56 120.0(12) . 2_657 ?
F56 C56 C51 122.3(12) . . ?
F56 C56 C52 117.0(11) . 2_657 ?
C51 C56 C52 120.6(12) . 2_657 ?
C66 C61 C62 117.7(11) . . ?
C66 C61 I2 121.9(9) . . ?
C62 C61 I2 120.4(9) . . ?
C66 C62 F62 118.6(11) 2 . ?
C66 C62 C61 121.4(11) 2 . ?
F62 C62 C61 120.0(11) . . ?
F66 C66 C62 119.3(12) . 2 ?
F66 C66 C61 119.8(11) . . ?
C62 C66 C61 120.9(12) 2 . ?
C72 C71 C76 117.3(11) . . ?
C72 C71 I71 121.8(9) . . ?
C76 C71 I71 120.8(9) . . ?
F72 C72 C76 119.2(12) . 2_656 ?
F72 C72 C71 119.3(11) . . ?
C76 C72 C71 121.4(11) 2_656 . ?
F76 C76 C72 118.9(11) . 2_656 ?
F76 C76 C71 119.8(11) . . ?
C72 C76 C71 121.2(11) 2_656 . ?
N82 C81 S81 178.4(11) . . ?
N92 C91 S91 179.2(12) . . ?
C107 N101 C105 112.3(9) . . ?
C107 N101 C101 111.9(9) . . ?
C105 N101 C101 105.7(9) . . ?
C107 N101 C103 106.7(9) . . ?
C105 N101 C103 110.8(9) . . ?
C101 N101 C103 109.4(9) . . ?
C102 C101 N101 115.5(10) . . ?
C102 C101 H10A 108.4 . . ?
N101 C101 H10A 108.4 . . ?
C102 C101 H10B 108.4 . . ?
N101 C101 H10B 108.4 . . ?
H10A C101 H10B 107.5 . . ?
C101 C102 H10C 109.5 . . ?
C101 C102 H10D 109.5 . . ?
H10C C102 H10D 109.5 . . ?
C101 C102 H10E 109.5 . . ?
H10C C102 H10E 109.5 . . ?
H10D C102 H10E 109.5 . . ?
C104 C103 N101 115.9(11) . . ?
C104 C103 H10F 108.3 . . ?
N101 C103 H10F 108.3 . . ?
C104 C103 H10G 108.3 . . ?
N101 C103 H10G 108.3 . . ?
H10F C103 H10G 107.4 . . ?
C103 C104 H10H 109.5 . . ?
C103 C104 H10I 109.5 . . ?
H10H C104 H10I 109.5 . . ?
C103 C104 H10J 109.5 . . ?
H10H C104 H10J 109.5 . . ?
H10I C104 H10J 109.5 . . ?
C106 C105 N101 115.3(11) . . ?
C106 C105 H10K 108.4 . . ?
N101 C105 H10K 108.4 . . ?
C106 C105 H10L 108.4 . . ?
N101 C105 H10L 108.4 . . ?
H10K C105 H10L 107.5 . . ?
C105 C106 H10M 109.5 . . ?
C105 C106 H10N 109.5 . . ?
H10M C106 H10N 109.5 . . ?
C105 C106 H10O 109.5 . . ?
H10M C106 H10O 109.5 . . ?
H10N C106 H10O 109.5 . . ?
N101 C107 C108 114.0(10) . . ?
N101 C107 H10P 108.8 . . ?
C108 C107 H10P 108.8 . . ?
N101 C107 H10Q 108.8 . . ?
C108 C107 H10Q 108.8 . . ?
H10P C107 H10Q 107.6 . . ?
C107 C108 H10R 109.5 . . ?
C107 C108 H10S 109.5 . . ?
H10R C108 H10S 109.5 . . ?
C107 C108 H10T 109.5 . . ?
H10R C108 H10T 109.5 . . ?
H10S C108 H10T 109.5 . . ?
C113 N111 C117 110.5(11) . . ?
C113 N111 C111 111.7(10) . . ?
C117 N111 C111 105.1(10) . . ?
C113 N111 C115 107.2(9) . . ?
C117 N111 C115 111.2(10) . . ?
C111 N111 C115 111.2(10) . . ?
N111 C111 C112 114.2(11) . . ?
N111 C111 H11A 108.7 . . ?
C112 C111 H11A 108.7 . . ?
N111 C111 H11B 108.7 . . ?
C112 C111 H11B 108.7 . . ?
H11A C111 H11B 107.6 . . ?
C111 C112 H11C 109.5 . . ?
C111 C112 H11D 109.5 . . ?
H11C C112 H11D 109.5 . . ?
C111 C112 H11E 109.5 . . ?
H11C C112 H11E 109.5 . . ?
H11D C112 H11E 109.5 . . ?
N111 C113 C114 115.6(11) . . ?
N111 C113 H11F 108.4 . . ?
C114 C113 H11F 108.4 . . ?
N111 C113 H11G 108.4 . . ?
C114 C113 H11G 108.4 . . ?
H11F C113 H11G 107.4 . . ?
C113 C114 H11H 109.5 . . ?
C113 C114 H11I 109.5 . . ?
H11H C114 H11I 109.5 . . ?
C113 C114 H11J 109.5 . . ?
H11H C114 H11J 109.5 . . ?
H11I C114 H11J 109.5 . . ?
C116 C115 N111 114.4(10) . . ?
C116 C115 H11K 108.7 . . ?
N111 C115 H11K 108.7 . . ?
C116 C115 H11L 108.7 . . ?
N111 C115 H11L 108.7 . . ?
H11K C115 H11L 107.6 . . ?
C115 C116 H11M 109.5 . . ?
C115 C116 H11N 109.5 . . ?
H11M C116 H11N 109.5 . . ?
C115 C116 H11O 109.5 . . ?
H11M C116 H11O 109.5 . . ?
H11N C116 H11O 109.5 . . ?
C118 C117 N111 116.6(14) . . ?
C118 C117 H11P 108.1 . . ?
N111 C117 H11P 108.1 . . ?
C118 C117 H11Q 108.1 . . ?
N111 C117 H11Q 108.1 . . ?
H11P C117 H11Q 107.3 . . ?
C117 C118 H11R 109.5 . . ?
C117 C118 H11S 109.5 . . ?
H11R C118 H11S 109.5 . . ?
C117 C118 H11T 109.5 . . ?
H11R C118 H11T 109.5 . . ?
H11S C118 H11T 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 F2 179.3(11) . . . . ?
I1 C1 C2 F2 3.0(16) . . . . ?
C6 C1 C2 C3 2.1(18) . . . . ?
I1 C1 C2 C3 -174.2(9) . . . . ?
F2 C2 C3 F3 1.4(17) . . . . ?
C1 C2 C3 F3 178.6(11) . . . . ?
F2 C2 C3 C4 -178.8(11) . . . . ?
C1 C2 C3 C4 -1.6(19) . . . . ?
F3 C3 C4 C5 -179.9(11) . . . . ?
C2 C3 C4 C5 0.3(18) . . . . ?
F3 C3 C4 I4 -2.4(16) . . . . ?
C2 C3 C4 I4 177.8(9) . . . . ?
C3 C4 C5 F5 179.9(11) . . . . ?
I4 C4 C5 F5 2.3(16) . . . . ?
C3 C4 C5 C6 0.4(18) . . . . ?
I4 C4 C5 C6 -177.2(9) . . . . ?
F5 C5 C6 F6 1.5(16) . . . . ?
C4 C5 C6 F6 -179.0(11) . . . . ?
F5 C5 C6 C1 -179.3(10) . . . . ?
C4 C5 C6 C1 0.2(18) . . . . ?
C2 C1 C6 F6 177.7(11) . . . . ?
I1 C1 C6 F6 -5.9(15) . . . . ?
C2 C1 C6 C5 -1.4(18) . . . . ?
I1 C1 C6 C5 174.9(9) . . . . ?
C16 C11 C12 F12 179.8(11) . . . . ?
I11 C11 C12 F12 -3.1(16) . . . . ?
C16 C11 C12 C13 -1.3(17) . . . . ?
I11 C11 C12 C13 175.8(9) . . . . ?
F12 C12 C13 C14 179.4(11) . . . . ?
C11 C12 C13 C14 0.4(19) . . . . ?
F12 C12 C13 F13 -0.9(16) . . . . ?
C11 C12 C13 F13 -179.9(10) . . . . ?
F13 C13 C14 C15 -178.9(10) . . . . ?
C12 C13 C14 C15 0.8(18) . . . . ?
F13 C13 C14 I14 2.1(16) . . . . ?
C12 C13 C14 I14 -178.2(9) . . . . ?
C13 C14 C15 F15 179.6(11) . . . . ?
I14 C14 C15 F15 -1.4(15) . . . . ?
C13 C14 C15 C16 -1.1(17) . . . . ?
I14 C14 C15 C16 177.9(9) . . . . ?
C12 C11 C16 F17 -179.7(10) . . . . ?
I11 C11 C16 F17 3.3(16) . . . . ?
C12 C11 C16 C15 1.0(18) . . . . ?
I11 C11 C16 C15 -176.0(9) . . . . ?
F15 C15 C16 F17 0.2(16) . . . . ?
C14 C15 C16 F17 -179.1(10) . . . . ?
F15 C15 C16 C11 179.5(10) . . . . ?
C14 C15 C16 C11 0.2(18) . . . . ?
C26 C21 C22 F22 180.0(10) . . . . ?
I21 C21 C22 F22 -4.7(15) . . . . ?
C26 C21 C22 C26 0.6(19) . . . 3_666 ?
I21 C21 C22 C26 175.9(9) . . . 3_666 ?
C22 C21 C26 F26 178.7(10) . . . . ?
I21 C21 C26 F26 3.4(15) . . . . ?
C22 C21 C26 C22 -0.6(19) . . . 3_666 ?
I21 C21 C26 C22 -176.0(8) . . . 3_666 ?
C36 C31 C32 F32 178.8(10) . . . . ?
I31 C31 C32 F32 -2.6(15) . . . . ?
C36 C31 C32 C36 -1.9(15) . . . 2_556 ?
I31 C31 C32 C36 176.7(9) . . . 2_556 ?
C32 C31 C36 F36 -179.3(10) . . . . ?
I31 C31 C36 F36 2.1(15) . . . . ?
C32 C31 C36 C32 2.3(15) . . . 2_556 ?
I31 C31 C36 C32 -176.3(9) . . . 2_556 ?
C46 C41 C42 F41 -179.4(11) . . . . ?
I41 C41 C42 F41 -2.7(16) . . . . ?
C46 C41 C42 C46 -0.1(19) . . . 3_675 ?
I41 C41 C42 C46 176.6(8) . . . 3_675 ?
C42 C41 C46 F46 -179.6(10) . . . . ?
I41 C41 C46 F46 3.8(15) . . . . ?
C42 C41 C46 C42 0.1(19) . . . 3_675 ?
I41 C41 C46 C42 -176.6(9) . . . 3_675 ?
C56 C51 C52 F52 178.8(11) . . . . ?
I51 C51 C52 F52 1.0(16) . . . . ?
C56 C51 C52 C56 1.8(16) . . . 2_657 ?
I51 C51 C52 C56 -175.9(9) . . . 2_657 ?
C52 C51 C56 F56 178.0(11) . . . . ?
I51 C51 C56 F56 -4.2(16) . . . . ?
C52 C51 C56 C52 0.7(16) . . . 2_657 ?
I51 C51 C56 C52 178.6(9) . . . 2_657 ?
C66 C61 C62 C66 0.0(16) . . . 2 ?
I2 C61 C62 C66 -177.4(9) . . . 2 ?
C66 C61 C62 F62 179.9(10) . . . . ?
I2 C61 C62 F62 2.5(15) . . . . ?
C62 C61 C66 F66 -179.3(11) . . . . ?
I2 C61 C66 F66 -1.9(16) . . . . ?
C62 C61 C66 C62 -0.8(16) . . . 2 ?
I2 C61 C66 C62 176.6(9) . . . 2 ?
C76 C71 C72 F72 179.2(11) . . . . ?
I71 C71 C72 F72 -3.9(16) . . . . ?
C76 C71 C72 C76 0.1(16) . . . 2_656 ?
I71 C71 C72 C76 176.9(9) . . . 2_656 ?
C72 C71 C76 F76 179.4(10) . . . . ?
I71 C71 C76 F76 2.5(16) . . . . ?
C72 C71 C76 C72 1.0(16) . . . 2_656 ?
I71 C71 C76 C72 -175.9(9) . . . 2_656 ?
C107 N101 C101 C102 55.0(14) . . . . ?
C105 N101 C101 C102 177.6(11) . . . . ?
C103 N101 C101 C102 -63.1(14) . . . . ?
C107 N101 C103 C104 175.7(12) . . . . ?
C105 N101 C103 C104 53.2(15) . . . . ?
C101 N101 C103 C104 -63.0(14) . . . . ?
C107 N101 C105 C106 -60.4(14) . . . . ?
C101 N101 C105 C106 177.3(11) . . . . ?
C103 N101 C105 C106 58.8(14) . . . . ?
C105 N101 C107 C108 -60.1(14) . . . . ?
C101 N101 C107 C108 58.7(14) . . . . ?
C103 N101 C107 C108 178.3(11) . . . . ?
C113 N111 C111 C112 62.1(14) . . . . ?
C117 N111 C111 C112 -178.1(12) . . . . ?
C115 N111 C111 C112 -57.7(14) . . . . ?
C117 N111 C113 C114 -59.0(16) . . . . ?
C111 N111 C113 C114 57.6(16) . . . . ?
C115 N111 C113 C114 179.7(13) . . . . ?
C113 N111 C115 C116 -179.0(12) . . . . ?
C117 N111 C115 C116 60.2(15) . . . . ?
C111 N111 C115 C116 -56.5(14) . . . . ?
C113 N111 C117 C118 -58.5(19) . . . . ?
C111 N111 C117 C118 -179.2(16) . . . . ?
C115 N111 C117 C118 60(2) . . . . ?

# Attachment '3b_JBB49d.cif'

data_jbb49d
_database_code_depnum_ccdc_archive 'CCDC 739583'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
tetrabutylammonium thiocyanate, 1,4-diiodotetrafluorobenzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 N, C6 F4 I2, C N S'
_chemical_formula_sum            'C23 H36 F4 I2 N2 S'
_chemical_formula_weight         702.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   10.0837(7)
_cell_length_b                   22.4174(14)
_cell_length_c                   12.9033(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.2206(19)
_cell_angle_gamma                90.00
_cell_volume                     2912.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8336
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      24.05

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1384
_exptl_absorpt_coefficient_mu    2.270
_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  0.7200
_exptl_absorpt_correction_T_max  1.0

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector                 'CCD plate'
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            61852
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         27.57
_reflns_number_total             6715
_reflns_number_gt                4588
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0247P)²+2.1970P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6715
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0629
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.49354(2) 0.093025(10) 0.916492(18) 0.06832(9) Uani 1 1 d . . .
I2 I 0.89066(3) -0.134521(11) 0.72930(2) 0.07653(9) Uani 1 1 d . . .
F1 F 0.7538(2) 0.02551(11) 1.01588(16) 0.0991(7) Uani 1 1 d . . .
F2 F 0.9036(3) -0.06168(12) 0.94606(19) 0.1076(8) Uani 1 1 d . . .
F3 F 0.6376(2) -0.06642(11) 0.63565(16) 0.0997(8) Uani 1 1 d . . .
F4 F 0.4888(2) 0.01980(10) 0.70493(17) 0.0928(7) Uani 1 1 d . . .
C1 C 0.6161(3) 0.02544(14) 0.8632(2) 0.0598(8) Uani 1 1 d . . .
C2 C 0.7233(4) 0.00300(16) 0.9212(2) 0.0679(9) Uani 1 1 d . . .
C3 C 0.8005(4) -0.04173(16) 0.8856(3) 0.0699(9) Uani 1 1 d . . .
C4 C 0.7754(3) -0.06660(15) 0.7893(3) 0.0637(8) Uani 1 1 d . . .
C5 C 0.6689(4) -0.04443(16) 0.7311(3) 0.0692(9) Uani 1 1 d . . .
C6 C 0.5917(4) 0.00037(16) 0.7667(3) 0.0660(9) Uani 1 1 d . . .
S1 S 0.29537(11) 0.20017(5) 0.97725(10) 0.0905(3) Uani 1 1 d . . .
N1 N 0.4690(4) 0.27635(18) 0.8866(3) 0.1037(12) Uani 1 1 d . . .
C7 C 0.3970(4) 0.24595(17) 0.9252(3) 0.0668(9) Uani 1 1 d . . .
N2 N 0.3178(2) 0.21179(11) 0.58491(17) 0.0553(6) Uani 1 1 d . B .
C8 C 0.4590(3) 0.19608(15) 0.6223(2) 0.0611(8) Uani 1 1 d . . .
H8A H 0.5092 0.2328 0.6307 0.073 Uiso 1 1 calc R . .
H8B H 0.4564 0.1779 0.6904 0.073 Uiso 1 1 calc R . .
C9 C 0.5333(3) 0.15482(19) 0.5538(3) 0.0754(10) Uani 1 1 d . . .
H9A H 0.5425 0.1734 0.4867 0.090 Uiso 1 1 calc R . .
H9B H 0.4836 0.1181 0.5430 0.090 Uiso 1 1 calc R . .
C10 C 0.6690(4) 0.1410(2) 0.6031(3) 0.0907(12) Uani 1 1 d . . .
H10A H 0.7191 0.1778 0.6113 0.109 Uiso 1 1 calc R . .
H10B H 0.6591 0.1244 0.6716 0.109 Uiso 1 1 calc R . .
C11 C 0.7457(5) 0.0978(3) 0.5405(5) 0.142(2) Uani 1 1 d . . .
H11A H 0.8315 0.0911 0.5745 0.213 Uiso 1 1 calc R . .
H11B H 0.7563 0.1141 0.4726 0.213 Uiso 1 1 calc R . .
H11C H 0.6984 0.0607 0.5343 0.213 Uiso 1 1 calc R . .
C12 C 0.3159(4) 0.24418(17) 0.4816(2) 0.0694(10) Uani 1 1 d . . .
H12A H 0.3521 0.2176 0.4310 0.083 Uiso 1 1 calc R A 1
H12B H 0.2240 0.2518 0.4593 0.083 Uiso 1 1 calc R A 1
C13A C 0.3902(4) 0.3022(2) 0.4791(3) 0.0897(12) Uani 0.50 1 d P B 1
H13A H 0.4846 0.2955 0.4926 0.108 Uiso 0.50 1 calc PR B 1
H13B H 0.3595 0.3293 0.5312 0.108 Uiso 0.50 1 calc PR B 1
C14A C 0.3630(11) 0.3277(10) 0.3717(14) 0.113(8) Uani 0.52(6) 1 d P B 1
H14A H 0.2703 0.3198 0.3525 0.136 Uiso 0.52(6) 1 calc PR B 1
H14B H 0.3718 0.3707 0.3781 0.136 Uiso 0.52(6) 1 calc PR B 1
C15A C 0.421(2) 0.3141(11) 0.3031(13) 0.146(9) Uani 0.374(13) 1 d P B 1
H15A H 0.3929 0.3374 0.2436 0.218 Uiso 0.374(13) 1 calc PR B 1
H15B H 0.4061 0.2726 0.2884 0.218 Uiso 0.374(13) 1 calc PR B 1
H15C H 0.5142 0.3206 0.3192 0.218 Uiso 0.374(13) 1 calc PR B 1
C13B C 0.3902(4) 0.3022(2) 0.4791(3) 0.0897(12) Uani 0.50 1 d P B 2
H13C H 0.4819 0.2958 0.5033 0.108 Uiso 0.50 1 calc PR B 2
H13D H 0.3512 0.3305 0.5253 0.108 Uiso 0.50 1 calc PR B 2
C14B C 0.385(4) 0.3281(11) 0.367(2) 0.198(17) Uani 0.48(6) 1 d P B 2
H14C H 0.4247 0.2984 0.3234 0.237 Uiso 0.48(6) 1 calc PR B 2
H14D H 0.2924 0.3311 0.3439 0.237 Uiso 0.48(6) 1 calc PR B 2
C15B C 0.4398(9) 0.3785(5) 0.3472(7) 0.110(4) Uani 0.626(13) 1 d P B 2
H15D H 0.4235 0.3879 0.2751 0.166 Uiso 0.626(13) 1 calc PR B 2
H15E H 0.5337 0.3760 0.3632 0.166 Uiso 0.626(13) 1 calc PR B 2
H15F H 0.4026 0.4092 0.3887 0.166 Uiso 0.626(13) 1 calc PR B 2
C16 C 0.2343(3) 0.15669(16) 0.5665(3) 0.0673(9) Uani 1 1 d . . .
H16A H 0.2701 0.1344 0.5100 0.081 Uiso 1 1 calc R B .
H16B H 0.1452 0.1691 0.5437 0.081 Uiso 1 1 calc R . .
C17 C 0.2243(4) 0.11518(17) 0.6577(3) 0.0837(11) Uani 1 1 d . B .
H17A H 0.1788 0.1351 0.7122 0.100 Uiso 1 1 calc R . .
H17B H 0.3126 0.1044 0.6850 0.100 Uiso 1 1 calc R . .
C18 C 0.1481(5) 0.0591(2) 0.6236(5) 0.136(2) Uani 1 1 d . . .
H18A H 0.0614 0.0707 0.5941 0.164 Uiso 1 1 calc R B .
H18B H 0.1950 0.0396 0.5694 0.164 Uiso 1 1 calc R . .
C19 C 0.1304(7) 0.0161(3) 0.7074(7) 0.205(4) Uani 1 1 d . B .
H19A H 0.0836 -0.0183 0.6800 0.307 Uiso 1 1 calc R . .
H19B H 0.0802 0.0343 0.7600 0.307 Uiso 1 1 calc R . .
H19C H 0.2157 0.0041 0.7371 0.307 Uiso 1 1 calc R . .
C20 C 0.2624(3) 0.25064(15) 0.6683(2) 0.0655(9) Uani 1 1 d . . .
H20A H 0.3215 0.2844 0.6802 0.079 Uiso 1 1 calc R B .
H20B H 0.2636 0.2278 0.7322 0.079 Uiso 1 1 calc R . .
C21 C 0.1229(4) 0.27428(18) 0.6458(3) 0.0811(11) Uani 1 1 d . B .
H21A H 0.0610 0.2412 0.6396 0.097 Uiso 1 1 calc R . .
H21B H 0.1187 0.2957 0.5804 0.097 Uiso 1 1 calc R . .
C22 C 0.0835(5) 0.3158(2) 0.7325(3) 0.0985(14) Uani 1 1 d . . .
H22A H -0.0110 0.3238 0.7234 0.118 Uiso 1 1 calc R B .
H22B H 0.0991 0.2955 0.7984 0.118 Uiso 1 1 calc R . .
C23 C 0.1544(6) 0.3726(2) 0.7371(4) 0.1282(19) Uani 1 1 d . B .
H23A H 0.1248 0.3959 0.7938 0.192 Uiso 1 1 calc R . .
H23B H 0.1368 0.3939 0.6733 0.192 Uiso 1 1 calc R . .
H23C H 0.2480 0.3653 0.7472 0.192 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 2.095(3) . ?
I2 C4 2.090(3) . ?
F1 C2 1.341(4) . ?
F2 C3 1.341(4) . ?
F3 C5 1.348(4) . ?
F4 C6 1.345(4) . ?
C1 C2 1.375(5) . ?
C1 C6 1.376(4) . ?
C2 C3 1.365(5) . ?
C3 C4 1.373(5) . ?
C4 C5 1.368(5) . ?
C5 C6 1.366(5) . ?
S1 C7 1.623(4) . ?
N1 C7 1.131(5) . ?
N2 C16 1.507(4) . ?
N2 C20 1.515(4) . ?
N2 C12 1.517(4) . ?
N2 C8 1.519(4) . ?
C8 C9 1.508(5) . ?
C9 C10 1.508(5) . ?
C10 C11 1.503(6) . ?
C12 C13A 1.502(5) . ?
C13A C14A 1.511(15) . ?
C14A C15A 1.13(2) . ?
C14B C15B 1.29(3) . ?
C16 C17 1.508(5) . ?
C17 C18 1.525(6) . ?
C18 C19 1.467(8) . ?
C20 C21 1.516(5) . ?
C21 C22 1.524(5) . ?
C22 C23 1.459(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 116.0(3) . . ?
C2 C1 I1 123.1(2) . . ?
C6 C1 I1 120.9(3) . . ?
F1 C2 C3 118.5(3) . . ?
F1 C2 C1 119.4(3) . . ?
C3 C2 C1 122.1(3) . . ?
F2 C3 C2 119.2(3) . . ?
F2 C3 C4 119.2(3) . . ?
C2 C3 C4 121.6(3) . . ?
C5 C4 C3 116.6(3) . . ?
C5 C4 I2 119.8(2) . . ?
C3 C4 I2 123.6(3) . . ?
F3 C5 C6 117.9(3) . . ?
F3 C5 C4 120.3(3) . . ?
C6 C5 C4 121.8(3) . . ?
F4 C6 C5 118.3(3) . . ?
F4 C6 C1 119.8(3) . . ?
C5 C6 C1 121.9(3) . . ?
N1 C7 S1 177.7(4) . . ?
C16 N2 C20 111.0(3) . . ?
C16 N2 C12 105.9(2) . . ?
C20 N2 C12 111.2(2) . . ?
C16 N2 C8 111.5(2) . . ?
C20 N2 C8 106.5(2) . . ?
C12 N2 C8 110.9(2) . . ?
C9 C8 N2 116.3(3) . . ?
C8 C9 C10 110.3(3) . . ?
C11 C10 C9 112.8(4) . . ?
C13A C12 N2 116.8(3) . . ?
C12 C13A C14A 106.5(9) . . ?
C15A C14A C13A 122.6(14) . . ?
N2 C16 C17 116.4(3) . . ?
C16 C17 C18 109.8(4) . . ?
C19 C18 C17 114.2(6) . . ?
N2 C20 C21 116.1(3) . . ?
C20 C21 C22 110.5(3) . . ?
C23 C22 C21 114.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.056

# Attachment '4a_PC32.cif'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2008-01-23 at 19:31:36
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:\progs\wingx\files\archive.dat
# CIF files read : job struct

data_job4
_database_code_depnum_ccdc_archive 'CCDC 739584'

_audit_creation_date             2008-01-23T19:31:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C8 H20 N, C6 F3 I3, C N S '
_chemical_formula_sum            'C15 H20 F3 I3 N2 S'
_chemical_formula_weight         698.09
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0510(4)
_cell_length_b                   21.1985(12)
_cell_length_c                   13.2534(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.872(2)
_cell_angle_gamma                90
_cell_volume                     2221.35(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9550
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      27.39
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    2.087
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1304
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.340
_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  0.146
_exptl_absorpt_correction_T_max  0.545

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_number            20203
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.4
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_full        27.42
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_reflns_number_total             5003
_reflns_number_gt                4431
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_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)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0109P)²+1.6437P] 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_number_reflns         5003
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0203
_refine_ls_wR_factor_ref         0.0407
_refine_ls_wR_factor_gt          0.0391
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.098

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2940(3) -0.06822(12) 0.5161(2) 0.0176(6) Uani 1 d . . .
I1 I 0.34531(2) -0.164006(8) 0.549133(14) 0.02089(5) Uani 1 d . . .
C2 C 0.2552(3) -0.02727(13) 0.5897(2) 0.0185(6) Uani 1 d . . .
F2 F 0.2548(2) -0.05011(7) 0.68495(12) 0.0249(4) Uani 1 d . . .
I3 I 0.16206(2) 0.095423(8) 0.687779(14) 0.01878(5) Uani 1 d . . .
C3 C 0.2146(3) 0.03572(12) 0.5705(2) 0.0177(6) Uani 1 d . . .
C4 C 0.2116(3) 0.05741(12) 0.4716(2) 0.0191(6) Uani 1 d . . .
F4 F 0.16864(19) 0.11822(7) 0.44902(12) 0.0257(4) Uani 1 d . . .
I5 I 0.23333(2) 0.052233(8) 0.242683(14) 0.02065(5) Uani 1 d . . .
C5 C 0.2495(3) 0.01911(12) 0.3933(2) 0.0180(6) Uani 1 d . . .
C6 C 0.2918(3) -0.04348(12) 0.4191(2) 0.0183(6) Uani 1 d . . .
F6 F 0.3302(2) -0.08177(7) 0.34557(12) 0.0248(4) Uani 1 d . . .
S11 S -0.10152(8) -0.18926(3) 0.12914(5) 0.01998(14) Uani 1 d . . .
C12 C -0.1544(3) -0.13861(13) 0.0333(2) 0.0183(6) Uani 1 d . . .
N13 N -0.1930(3) -0.10326(11) -0.0341(2) 0.0264(6) Uani 1 d . . .
N20 N 0.3200(3) -0.16198(10) -0.05991(17) 0.0191(5) Uani 1 d . . .
C21 C 0.4398(4) -0.15964(16) 0.0435(2) 0.0314(7) Uani 1 d . . .
H21A H 0.5042 -0.1997 0.053 0.038 Uiso 1 calc R . .
H21B H 0.5221 -0.1252 0.0415 0.038 Uiso 1 calc R . .
C22 C 0.3585(4) -0.14969(19) 0.1362(3) 0.0419(9) Uani 1 d . . .
H22A H 0.2949 -0.11 0.1285 0.063 Uiso 1 calc R . .
H22B H 0.4463 -0.1479 0.1983 0.063 Uiso 1 calc R . .
H22C H 0.2814 -0.1848 0.1418 0.063 Uiso 1 calc R . .
C23 C 0.2096(4) -0.10354(14) -0.0767(3) 0.0327(7) Uani 1 d . . .
H23A H 0.1285 -0.1054 -0.0292 0.039 Uiso 1 calc R . .
H23B H 0.1431 -0.1048 -0.1475 0.039 Uiso 1 calc R . .
C24 C 0.3015(4) -0.04057(14) -0.0614(3) 0.0376(8) Uani 1 d . . .
H24A H 0.3619 -0.0372 0.0099 0.056 Uiso 1 calc R . .
H24B H 0.2193 -0.0062 -0.0763 0.056 Uiso 1 calc R . .
H24C H 0.3825 -0.0378 -0.1078 0.056 Uiso 1 calc R . .
C25 C 0.2064(4) -0.21994(14) -0.0628(2) 0.0303(7) Uani 1 d . . .
H25A H 0.2793 -0.2576 -0.0463 0.036 Uiso 1 calc R . .
H25B H 0.1389 -0.2155 -0.008 0.036 Uiso 1 calc R . .
C26 C 0.0869(4) -0.23174(15) -0.1630(3) 0.0335(7) Uani 1 d . . .
H26A H 0.013 -0.195 -0.1803 0.05 Uiso 1 calc R . .
H26B H 0.018 -0.2691 -0.1563 0.05 Uiso 1 calc R . .
H26C H 0.152 -0.2388 -0.2174 0.05 Uiso 1 calc R . .
C27 C 0.4233(3) -0.16466(14) -0.1444(2) 0.0256(6) Uani 1 d . . .
H27A H 0.3445 -0.1624 -0.2114 0.031 Uiso 1 calc R . .
H27B H 0.496 -0.1267 -0.1388 0.031 Uiso 1 calc R . .
C28 C 0.5344(3) -0.22202(14) -0.1452(2) 0.0269(7) Uani 1 d . . .
H28A H 0.615 -0.2246 -0.0799 0.04 Uiso 1 calc R . .
H28B H 0.5964 -0.2186 -0.2019 0.04 Uiso 1 calc R . .
H28C H 0.464 -0.2601 -0.1542 0.04 Uiso 1 calc R . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C6 1.384(4) . ?
C1 C2 1.385(4) . ?
C1 I1 2.102(3) . ?
C2 F2 1.353(3) . ?
C2 C3 1.387(4) . ?
I3 C3 2.109(3) . ?
C3 C4 1.384(4) . ?
C4 F4 1.353(3) . ?
C4 C5 1.396(4) . ?
I5 C5 2.096(3) . ?
C5 C6 1.396(4) . ?
C6 F6 1.349(3) . ?
S11 C12 1.656(3) . ?
C12 N13 1.163(3) . ?
N20 C27 1.516(3) . ?
N20 C23 1.517(3) . ?
N20 C21 1.521(3) . ?
N20 C25 1.528(3) . ?
C21 C22 1.512(4) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 C24 1.521(4) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
C25 C26 1.506(4) . ?
C25 H25A 0.99 . ?
C25 H25B 0.99 . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C26 H26C 0.98 . ?
C27 C28 1.511(4) . ?
C27 H27A 0.99 . ?
C27 H27B 0.99 . ?
C28 H28A 0.98 . ?
C28 H28B 0.98 . ?
C28 H28C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 116.8(2) . . ?
C6 C1 I1 121.81(19) . . ?
C2 C1 I1 121.3(2) . . ?
F2 C2 C1 118.3(2) . . ?
F2 C2 C3 118.3(2) . . ?
C1 C2 C3 123.4(3) . . ?
C4 C3 C2 117.1(2) . . ?
C4 C3 I3 121.89(19) . . ?
C2 C3 I3 121.0(2) . . ?
F4 C4 C3 118.9(2) . . ?
F4 C4 C5 118.2(2) . . ?
C3 C4 C5 122.9(2) . . ?
C4 C5 C6 116.6(2) . . ?
C4 C5 I5 122.00(19) . . ?
C6 C5 I5 121.4(2) . . ?
F6 C6 C1 118.6(2) . . ?
F6 C6 C5 118.2(2) . . ?
C1 C6 C5 123.2(2) . . ?
N13 C12 S11 179.4(2) . . ?
C27 N20 C23 108.1(2) . . ?
C27 N20 C21 108.9(2) . . ?
C23 N20 C21 111.1(2) . . ?
C27 N20 C25 111.1(2) . . ?
C23 N20 C25 108.7(2) . . ?
C21 N20 C25 108.9(2) . . ?
C22 C21 N20 116.0(2) . . ?
C22 C21 H21A 108.3 . . ?
N20 C21 H21A 108.3 . . ?
C22 C21 H21B 108.3 . . ?
N20 C21 H21B 108.3 . . ?
H21A C21 H21B 107.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N20 C23 C24 116.1(2) . . ?
N20 C23 H23A 108.3 . . ?
C24 C23 H23A 108.3 . . ?
N20 C23 H23B 108.3 . . ?
C24 C23 H23B 108.3 . . ?
H23A C23 H23B 107.4 . . ?
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 N20 115.8(2) . . ?
C26 C25 H25A 108.3 . . ?
N20 C25 H25A 108.3 . . ?
C26 C25 H25B 108.3 . . ?
N20 C25 H25B 108.3 . . ?
H25A C25 H25B 107.4 . . ?
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 . . ?
C28 C27 N20 116.3(2) . . ?
C28 C27 H27A 108.2 . . ?
N20 C27 H27A 108.2 . . ?
C28 C27 H27B 108.2 . . ?
N20 C27 H27B 108.2 . . ?
H27A C27 H27B 107.4 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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 F2 179.4(2) . . . . ?
I1 C1 C2 F2 1.5(3) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
I1 C1 C2 C3 -177.63(19) . . . . ?
F2 C2 C3 C4 -178.3(2) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
F2 C2 C3 I3 2.2(3) . . . . ?
C1 C2 C3 I3 -178.70(19) . . . . ?
C2 C3 C4 F4 178.5(2) . . . . ?
I3 C3 C4 F4 -2.0(3) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
I3 C3 C4 C5 178.58(19) . . . . ?
F4 C4 C5 C6 -179.5(2) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
F4 C4 C5 I5 -2.2(3) . . . . ?
C3 C4 C5 I5 177.22(19) . . . . ?
C2 C1 C6 F6 179.5(2) . . . . ?
I1 C1 C6 F6 -2.5(3) . . . . ?
C2 C1 C6 C5 -1.4(4) . . . . ?
I1 C1 C6 C5 176.51(19) . . . . ?
C4 C5 C6 F6 -179.6(2) . . . . ?
I5 C5 C6 F6 3.1(3) . . . . ?
C4 C5 C6 C1 1.3(4) . . . . ?
I5 C5 C6 C1 -176.00(19) . . . . ?
C27 N20 C21 C22 173.6(3) . . . . ?
C23 N20 C21 C22 54.7(3) . . . . ?
C25 N20 C21 C22 -65.1(3) . . . . ?
C27 N20 C23 C24 -67.6(3) . . . . ?
C21 N20 C23 C24 51.9(4) . . . . ?
C25 N20 C23 C24 171.7(3) . . . . ?
C27 N20 C25 C26 -56.3(3) . . . . ?
C23 N20 C25 C26 62.6(3) . . . . ?
C21 N20 C25 C26 -176.2(2) . . . . ?
C23 N20 C27 C28 -176.4(2) . . . . ?
C21 N20 C27 C28 62.8(3) . . . . ?
C25 N20 C27 C28 -57.1(3) . . . . ?

# Attachment '4b_JBB51ec.cif'

data_jbb51ec
_database_code_depnum_ccdc_archive 'CCDC 739585'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Bis(tetrabutylammonium thiocyanate),
1,3,5-triiodo-2,4,7-trifluorobenzene
;
_chemical_name_common            'sym-C6F3I3, (TBASCN)2'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C16 H36 N), C6 F3 I3, 2(C N S)'
_chemical_formula_sum            'C40 H72 F3 I3 N4 S2'
_chemical_formula_weight         1110.84

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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

_cell_length_a                   17.574(4)
_cell_length_b                   18.064(4)
_cell_length_c                   16.310(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.42(3)
_cell_angle_gamma                90.00
_cell_volume                     5134.1(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    73233
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_F_000             2232
_exptl_absorpt_coefficient_mu    1.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.5782
_exptl_absorpt_correction_T_max  1.2086

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            98554
_diffrn_reflns_av_R_equivalents  0.0956
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         27.48
_reflns_number_total             11735
_reflns_number_gt                8057
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'

_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0513P)²+6.3758P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         11735
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1374
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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 0.184501(19) 0.65469(2) 0.54797(2) 0.06634(11) Uani 1 1 d . . .
I2 I -0.123722(18) 0.553919(19) 0.63055(2) 0.06663(11) Uani 1 1 d . . .
I3 I 0.14098(2) 0.33472(2) 0.64632(2) 0.07913(13) Uani 1 1 d . . .
F1 F 0.01005(18) 0.64946(16) 0.5711(2) 0.0791(8) Uani 1 1 d . . .
F2 F -0.02480(18) 0.40462(17) 0.6523(2) 0.0833(9) Uani 1 1 d . . .
F3 F 0.21524(16) 0.48306(18) 0.58763(19) 0.0767(8) Uani 1 1 d . . .
C1 C 0.1144(3) 0.5678(3) 0.5796(3) 0.0578(11) Uani 1 1 d . . .
C2 C 0.0385(3) 0.5809(3) 0.5866(3) 0.0607(11) Uani 1 1 d . . .
C3 C -0.0106(3) 0.5270(3) 0.6124(3) 0.0623(11) Uani 1 1 d . . .
C4 C 0.0209(3) 0.4581(3) 0.6276(3) 0.0635(12) Uani 1 1 d . . .
C5 C 0.0958(3) 0.4404(3) 0.6195(3) 0.0632(11) Uani 1 1 d . . .
C6 C 0.1407(3) 0.4966(3) 0.5953(3) 0.0604(11) Uani 1 1 d . . .
S1 S -0.28886(9) 0.60962(9) 0.67622(12) 0.0868(4) Uani 1 1 d . . .
N1 N -0.2142(5) 0.6916(4) 0.8056(4) 0.135(3) Uani 1 1 d . . .
C7 C -0.2447(4) 0.6581(3) 0.7520(4) 0.0813(17) Uani 1 1 d . . .
N10 N -0.7347(2) 0.83362(19) 0.7695(2) 0.0525(8) Uani 1 1 d . . .
C10 C -0.6807(3) 0.7684(3) 0.7619(3) 0.0617(11) Uani 1 1 d . . .
H10A H -0.6671 0.7473 0.8165 0.074 Uiso 1 1 calc R . .
H10B H -0.7087 0.7308 0.7278 0.074 Uiso 1 1 calc R . .
C11 C -0.6075(3) 0.7849(3) 0.7260(3) 0.0731(14) Uani 1 1 d . . .
H11A H -0.6201 0.8053 0.6709 0.088 Uiso 1 1 calc R . .
H11B H -0.5783 0.8218 0.7599 0.088 Uiso 1 1 calc R . .
C12 C -0.5592(4) 0.7166(4) 0.7216(5) 0.102(2) Uani 1 1 d . . .
H12A H -0.5460 0.6973 0.7772 0.123 Uiso 1 1 calc R . .
H12B H -0.5896 0.6794 0.6896 0.123 Uiso 1 1 calc R . .
C13 C -0.4870(4) 0.7283(6) 0.6845(6) 0.143(4) Uani 1 1 d . . .
H13A H -0.4599 0.6823 0.6835 0.215 Uiso 1 1 calc R . .
H13B H -0.4554 0.7637 0.7169 0.215 Uiso 1 1 calc R . .
H13C H -0.4992 0.7466 0.6291 0.215 Uiso 1 1 calc R . .
C14 C -0.7989(3) 0.8081(3) 0.8174(3) 0.0590(11) Uani 1 1 d . . .
H14A H -0.7757 0.7880 0.8698 0.071 Uiso 1 1 calc R . .
H14B H -0.8284 0.8513 0.8294 0.071 Uiso 1 1 calc R . .
C15 C -0.8540(3) 0.7508(3) 0.7755(3) 0.0748(14) Uani 1 1 d . . .
H15A H -0.8841 0.7725 0.7274 0.090 Uiso 1 1 calc R . .
H15B H -0.8255 0.7093 0.7573 0.090 Uiso 1 1 calc R . .
C16 C -0.9067(3) 0.7244(3) 0.8358(4) 0.0836(16) Uani 1 1 d . . .
H16A H -0.8757 0.7042 0.8842 0.100 Uiso 1 1 calc R . .
H16B H -0.9346 0.7664 0.8536 0.100 Uiso 1 1 calc R . .
C17 C -0.9630(5) 0.6668(5) 0.8009(6) 0.128(3) Uani 1 1 d . . .
H17A H -0.9952 0.6533 0.8417 0.192 Uiso 1 1 calc R . .
H17B H -0.9358 0.6239 0.7856 0.192 Uiso 1 1 calc R . .
H17C H -0.9940 0.6863 0.7530 0.192 Uiso 1 1 calc R . .
C18 C -0.6924(3) 0.8972(3) 0.8169(3) 0.0606(11) Uani 1 1 d . . .
H18A H -0.6565 0.9181 0.7828 0.073 Uiso 1 1 calc R . .
H18B H -0.7295 0.9354 0.8251 0.073 Uiso 1 1 calc R . .
C19 C -0.6488(3) 0.8780(3) 0.9000(3) 0.0656(12) Uani 1 1 d . . .
H19A H -0.6818 0.8499 0.9317 0.079 Uiso 1 1 calc R . .
H19B H -0.6052 0.8471 0.8920 0.079 Uiso 1 1 calc R . .
C20 C -0.6207(4) 0.9459(4) 0.9479(4) 0.101(2) Uani 1 1 d . . .
H20A H -0.6640 0.9774 0.9549 0.121 Uiso 1 1 calc R . .
H20B H -0.5866 0.9734 0.9168 0.121 Uiso 1 1 calc R . .
C21 C -0.5785(5) 0.9261(5) 1.0321(4) 0.117(3) Uani 1 1 d . . .
H21A H -0.5618 0.9706 1.0612 0.176 Uiso 1 1 calc R . .
H21B H -0.5348 0.8960 1.0253 0.176 Uiso 1 1 calc R . .
H21C H -0.6123 0.8993 1.0631 0.176 Uiso 1 1 calc R . .
C22 C -0.7656(3) 0.8598(3) 0.6833(3) 0.0635(12) Uani 1 1 d . . .
H22A H -0.7226 0.8742 0.6551 0.076 Uiso 1 1 calc R . .
H22B H -0.7908 0.8184 0.6531 0.076 Uiso 1 1 calc R . .
C23 C -0.8208(3) 0.9231(3) 0.6792(3) 0.0785(15) Uani 1 1 d . . .
H23A H -0.7954 0.9661 0.7057 0.094 Uiso 1 1 calc R . .
H23B H -0.8635 0.9103 0.7086 0.094 Uiso 1 1 calc R . .
C24 C -0.8507(4) 0.9415(4) 0.5892(4) 0.102(2) Uani 1 1 d . . .
H24A H -0.8076 0.9517 0.5593 0.123 Uiso 1 1 calc R . .
H24B H -0.8780 0.8990 0.5637 0.123 Uiso 1 1 calc R . .
C25 C -0.9033(5) 1.0071(5) 0.5828(6) 0.156(4) Uani 1 1 d . . .
H25A H -0.9201 1.0176 0.5256 0.233 Uiso 1 1 calc R . .
H25B H -0.8765 1.0493 0.6081 0.233 Uiso 1 1 calc R . .
H25C H -0.9471 0.9966 0.6105 0.233 Uiso 1 1 calc R . .
N30 N 0.3043(2) 0.1462(2) 0.4789(2) 0.0621(9) Uani 1 1 d . . .
C30 C 0.3208(3) 0.1064(3) 0.4012(3) 0.0756(14) Uani 1 1 d . . .
H30A H 0.3080 0.1392 0.3544 0.091 Uiso 1 1 calc R . .
H30B H 0.3754 0.0963 0.4058 0.091 Uiso 1 1 calc R . .
C31 C 0.2779(4) 0.0346(4) 0.3838(4) 0.0945(19) Uani 1 1 d . . .
H31A H 0.2234 0.0428 0.3839 0.113 Uiso 1 1 calc R . .
H31B H 0.2949 -0.0012 0.4266 0.113 Uiso 1 1 calc R . .
C32 C 0.2927(5) 0.0048(4) 0.2997(5) 0.120(3) Uani 1 1 d . . .
H32A H 0.2730 0.0396 0.2569 0.144 Uiso 1 1 calc R . .
H32B H 0.3476 0.0002 0.2987 0.144 Uiso 1 1 calc R . .
C33 C 0.2565(8) -0.0673(5) 0.2819(6) 0.193(6) Uani 1 1 d . . .
H33A H 0.2666 -0.0840 0.2285 0.290 Uiso 1 1 calc R . .
H33B H 0.2021 -0.0629 0.2823 0.290 Uiso 1 1 calc R . .
H33C H 0.2770 -0.1023 0.3232 0.290 Uiso 1 1 calc R . .
C34 C 0.3228(3) 0.0979(3) 0.5548(3) 0.0665(12) Uani 1 1 d . . .
H34A H 0.3095 0.1251 0.6022 0.080 Uiso 1 1 calc R . .
H34B H 0.2899 0.0546 0.5481 0.080 Uiso 1 1 calc R . .
C35 C 0.4038(4) 0.0719(4) 0.5744(4) 0.0934(19) Uani 1 1 d . . .
H35A H 0.4376 0.1140 0.5869 0.112 Uiso 1 1 calc R . .
H35B H 0.4195 0.0462 0.5272 0.112 Uiso 1 1 calc R . .
C36 C 0.4096(5) 0.0195(5) 0.6493(5) 0.115(2) Uani 1 1 d . . .
H36A H 0.3897 0.0446 0.6947 0.138 Uiso 1 1 calc R . .
H36B H 0.3776 -0.0235 0.6349 0.138 Uiso 1 1 calc R . .
C37 C 0.4876(5) -0.0050(6) 0.6770(7) 0.172(5) Uani 1 1 d . . .
H37A H 0.4875 -0.0373 0.7237 0.258 Uiso 1 1 calc R . .
H37B H 0.5194 0.0372 0.6925 0.258 Uiso 1 1 calc R . .
H37C H 0.5072 -0.0311 0.6330 0.258 Uiso 1 1 calc R . .
C38 C 0.3535(3) 0.2162(3) 0.4856(4) 0.0749(14) Uani 1 1 d . . .
H38A H 0.4068 0.2017 0.4879 0.090 Uiso 1 1 calc R . .
H38B H 0.3405 0.2450 0.4355 0.090 Uiso 1 1 calc R . .
C39 C 0.3458(4) 0.2649(4) 0.5577(5) 0.099(2) Uani 1 1 d . . .
H39A H 0.3535 0.2356 0.6080 0.119 Uiso 1 1 calc R . .
H39B H 0.2942 0.2849 0.5524 0.119 Uiso 1 1 calc R . .
C40 C 0.4024(5) 0.3276(4) 0.5648(6) 0.119(3) Uani 1 1 d . . .
H40A H 0.4539 0.3073 0.5705 0.143 Uiso 1 1 calc R . .
H40B H 0.3950 0.3562 0.5141 0.143 Uiso 1 1 calc R . .
C41 C 0.3956(6) 0.3782(5) 0.6362(6) 0.156(4) Uani 1 1 d . . .
H41A H 0.4330 0.4170 0.6370 0.234 Uiso 1 1 calc R . .
H41B H 0.4044 0.3507 0.6869 0.234 Uiso 1 1 calc R . .
H41C H 0.3451 0.3994 0.6305 0.234 Uiso 1 1 calc R . .
C42 C 0.2197(3) 0.1649(3) 0.4743(4) 0.0731(14) Uani 1 1 d . . .
H42A H 0.1912 0.1189 0.4749 0.088 Uiso 1 1 calc R . .
H42B H 0.2120 0.1921 0.5238 0.088 Uiso 1 1 calc R . .
C43 C 0.1865(4) 0.2085(4) 0.4016(5) 0.097(2) Uani 1 1 d . . .
H43A H 0.1962 0.1828 0.3517 0.117 Uiso 1 1 calc R . .
H43B H 0.2122 0.2560 0.4025 0.117 Uiso 1 1 calc R . .
C44 C 0.1019(5) 0.2212(5) 0.3983(6) 0.132(3) Uani 1 1 d . . .
H44A H 0.0929 0.2461 0.4489 0.158 Uiso 1 1 calc R . .
H44B H 0.0860 0.2548 0.3529 0.158 Uiso 1 1 calc R . .
C45 C 0.0532(6) 0.1572(7) 0.3885(9) 0.201(7) Uani 1 1 d . . .
H45A H 0.0007 0.1721 0.3884 0.301 Uiso 1 1 calc R . .
H45B H 0.0673 0.1235 0.4334 0.301 Uiso 1 1 calc R . .
H45C H 0.0589 0.1332 0.3371 0.301 Uiso 1 1 calc R . .
S2 S 0.41011(14) 0.64705(16) 0.97400(18) 0.1419(9) Uani 1 1 d . . .
N2 N 0.2818(4) 0.7150(5) 1.0025(4) 0.117(2) Uani 1 1 d . . .
C8 C 0.3303(5) 0.6878(3) 0.9925(4) 0.091(2) 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 2.101(5) . ?
I2 C3 2.104(5) . ?
I3 C5 2.092(5) . ?
F1 C2 1.346(6) . ?
F2 C4 1.351(6) . ?
F3 C6 1.354(5) . ?
C1 C2 1.374(6) . ?
C1 C6 1.379(7) . ?
C2 C3 1.401(7) . ?
C3 C4 1.371(7) . ?
C4 C5 1.377(7) . ?
C5 C6 1.375(7) . ?
S1 C7 1.628(7) . ?
N1 C7 1.138(8) . ?
N10 C22 1.516(6) . ?
N10 C14 1.523(6) . ?
N10 C18 1.524(6) . ?
N10 C10 1.528(6) . ?
C10 C11 1.510(7) . ?
C11 C12 1.504(8) . ?
C12 C13 1.489(9) . ?
C14 C15 1.519(7) . ?
C15 C16 1.512(7) . ?
C16 C17 1.496(9) . ?
C18 C19 1.508(7) . ?
C19 C20 1.501(8) . ?
C20 C21 1.517(9) . ?
C22 C23 1.494(7) . ?
C23 C24 1.529(8) . ?
C24 C25 1.499(11) . ?
N30 C34 1.515(6) . ?
N30 C42 1.517(6) . ?
N30 C30 1.517(6) . ?
N30 C38 1.528(6) . ?
C30 C31 1.507(8) . ?
C31 C32 1.528(9) . ?
C32 C33 1.462(12) . ?
C34 C35 1.494(8) . ?
C35 C36 1.539(9) . ?
C36 C37 1.456(10) . ?
C38 C39 1.489(8) . ?
C39 C40 1.502(9) . ?
C40 C41 1.497(11) . ?
C42 C43 1.480(8) . ?
C43 C44 1.499(10) . ?
C44 C45 1.435(13) . ?
S2 C8 1.646(8) . ?
N2 C8 1.014(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
C2 C1 C6 116.8(4) . . ?
C2 C1 I1 119.9(4) . . ?
C6 C1 I1 123.3(3) . . ?
F1 C2 C1 118.9(4) . . ?
F1 C2 C3 117.9(4) . . ?
C1 C2 C3 123.1(5) . . ?
C4 C3 C2 115.8(4) . . ?
C4 C3 I2 123.5(4) . . ?
C2 C3 I2 120.7(4) . . ?
F2 C4 C3 117.4(4) . . ?
F2 C4 C5 118.3(5) . . ?
C3 C4 C5 124.2(5) . . ?
C6 C5 C4 116.5(5) . . ?
C6 C5 I3 121.2(4) . . ?
C4 C5 I3 122.3(4) . . ?
F3 C6 C5 119.4(4) . . ?
F3 C6 C1 117.2(4) . . ?
C5 C6 C1 123.4(4) . . ?
N1 C7 S1 179.2(6) . . ?
C22 N10 C14 111.7(4) . . ?
C22 N10 C18 109.2(3) . . ?
C14 N10 C18 108.2(3) . . ?
C22 N10 C10 108.5(3) . . ?
C14 N10 C10 108.5(3) . . ?
C18 N10 C10 110.7(4) . . ?
C11 C10 N10 116.7(4) . . ?
C12 C11 C10 111.8(5) . . ?
C13 C12 C11 114.8(7) . . ?
C15 C14 N10 116.6(4) . . ?
C16 C15 C14 109.4(4) . . ?
C17 C16 C15 113.7(6) . . ?
C19 C18 N10 116.3(4) . . ?
C20 C19 C18 112.0(5) . . ?
C19 C20 C21 111.6(6) . . ?
C23 C22 N10 115.6(4) . . ?
C22 C23 C24 110.5(5) . . ?
C25 C24 C23 111.9(7) . . ?
C34 N30 C42 105.9(4) . . ?
C34 N30 C30 111.4(4) . . ?
C42 N30 C30 110.8(4) . . ?
C34 N30 C38 111.1(4) . . ?
C42 N30 C38 111.1(4) . . ?
C30 N30 C38 106.6(4) . . ?
C31 C30 N30 114.9(5) . . ?
C30 C31 C32 109.5(6) . . ?
C33 C32 C31 111.9(8) . . ?
C35 C34 N30 117.0(4) . . ?
C34 C35 C36 109.1(5) . . ?
C37 C36 C35 113.3(7) . . ?
C39 C38 N30 115.9(5) . . ?
C38 C39 C40 112.3(6) . . ?
C41 C40 C39 113.7(8) . . ?
C43 C42 N30 116.2(5) . . ?
C42 C43 C44 113.4(7) . . ?
C45 C44 C43 117.1(8) . . ?
N2 C8 S2 177.3(8) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.810
_refine_diff_density_rms         0.088


