Electronic Supplementary Material for CrystEngComm
This Journal is (c) The Royal Society of Chemistry 2006

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_publ_contact_author             
;
Toshimasa Katagiri
Department of Applied Chemistry,
Faculty of Engineering, Okayama University
3-1-1 Tsushimanaka,
Okayama
Japan
;
_publ_contact_author_email       tkata@cc.okayama-u.ac.jp
_publ_section_title              
;
Nanoporous organic layered crystals of double-headed
bis(trifluorolactate)s: Hydrogen-bonded systematic crystal
structures controlled by the symmetries of molecular components.
;

_publ_section_references         
;
teXsan Single Crystal Structure Analysis Software. Version 1.11
- Molecular Structure Corporation, Rigaku Corporation. (2000). .
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Rigaku, 3-9-12 Akishima, Tokyo, Japan.

SIR97 - A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo,
A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna,
J. Appl. Cryst. 1999, 32, 115-119.

SHELX97 [Includes SHELXS97, SHELXL97, CIFTAB] - Programs for
Crystal Structure Analysis (Release 97-2). G. M. Sheldrick,
Instit\"ut f\"ur Anorganische Chemie der Universit\"at,
Tammanstrasse 4, D-3400 G\"ottingen, Germany, 1998.

SAPI91, Structure Analysis Programs with Intelligent Control,
H.-F. Fan, Rigaku Corporation, 1991.

WinGX - L.J. Farrugia, J. Appl. Cryst., 1999, 32, 837-838.

PLATON, A Multipurpose Crystallographic Tool, Utrecht University,
Utrecht, The Netherlands, A. L. Spek, 1998.

SQUEEZE - P. v.d. Sluis and A. L. Spek, Acta Crystallogr., 1990, A46, 194-201.

ORTEP3 for Windows - L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.

MERCURY - I. J. Bruno, J. C. Cole, P. R. Edgington, M. K. Kessler,
C. F. Macrae, P. McCabe, J. Pearson and R. Taylor,
Acta Crystallogr., B58, 2002, 389-397.
;
_publ_contact_author_name        'Toshimasa Katagiri'
loop_
_publ_author_name
'Satoshi Takahashi'
'Toshimasa Katagiri'
'Kenji Uneyama'
#------------------------------------------------------------------------------
#------------------------------------------------------------------------------
data_3a
_database_code_depnum_ccdc_archive 'CCDC 246918'
_audit_creation_method           SHELXL-97
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_formula_sum            'C10 H12 F6 O6 '
_chemical_formula_moiety         'C10 H12 F6 O6 '
_chemical_formula_weight         342.19
_chemical_melting_point          357
_chemical_name_common            
'(S,S)-(-)-tetramethylene bis(3,3,3-trifluorolactate)'
_chemical_absolute_configuration syn
_chemical_optical_rotation       '[\a]^25^~D~= -6.28 (c = 1.0, acetone)'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.2325(14)
_cell_length_b                   5.0006(5)
_cell_length_c                   17.966(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.189(3)
_cell_angle_gamma                90.00
_cell_volume                     645.97(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5056
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.4
_cell_measurement_temperature    150(1)

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.759
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_special_details           
;A needle crystal was mounted on a glass capillary.
The crystal was cooled by cold nitrogen flux of a low temperature device
during the data collection.
;
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-IV Imaging Plate'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_reflns_number            2474
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1466
_reflns_number_gt                1390
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection       'RAPID-AUTO (Rigaku)'
_computing_cell_refinement       'PAPID-AUTO (Rigaku)'
_computing_data_reduction        'teXsan Ver. 1.11 (MSC)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'WinGX Ver. 1.7 (Farrugia, 1999)'
_computing_molecular_graphics    'Mercury Ver. 1.3 (Bruno et al., 2002)'

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

Non H-atoms were refined anisotropically.
H-atoms of OH have been located from Fourier difference maps
and fixed to its position.
The remaining H-atoms were included in calculated positions
and treated as riding atoms using the SHELXL default parameters.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0652P)^2^+0.4541P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
; The absolute configuration was assigned to agree with
that of its precursor (S)-trifluorolactic acid at the chiral centre C2.
This compound has no atom heavier than Si and analyzed by
Mo radiation so that Flack parameter is not listed.
Freidel pairs were merged before refinement.
;
_refine_ls_number_reflns         1466
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

#----------------------------------------------------------------------------#
# 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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

F1 F -0.1129(3) 0.2103(7) 0.88337(12) 0.0396(6) Uani 1 1 d . . .
F2 F -0.0080(3) 0.5551(6) 0.83186(12) 0.0371(6) Uani 1 1 d . . .
F3 F 0.1239(3) 0.1735(6) 0.82146(11) 0.0364(6) Uani 1 1 d . . .
F4 F 0.9602(3) 0.8746(5) 0.68609(11) 0.0328(5) Uani 1 1 d . . .
F5 F 0.8052(3) 1.2418(6) 0.68558(11) 0.0348(6) Uani 1 1 d . . .
F6 F 1.0693(3) 1.2335(6) 0.64209(12) 0.0359(6) Uani 1 1 d . . .
O1 O 0.1759(3) 0.1557(6) 0.98535(13) 0.0279(6) Uani 1 1 d . . .
O2 O 0.4990(3) 0.3357(6) 0.94652(12) 0.0251(5) Uani 1 1 d . . .
O3 O 0.3598(3) 0.6747(6) 0.87884(12) 0.0238(5) Uani 1 1 d . . .
O4 O 0.5615(3) 0.8744(6) 0.62154(11) 0.0239(6) Uani 1 1 d . . .
O5 O 0.6624(3) 0.6181(6) 0.53106(12) 0.0263(5) Uani 1 1 d . . .
O6 O 0.9569(4) 0.9337(5) 0.52473(13) 0.0281(6) Uani 1 1 d . . .
C1 C 0.0412(4) 0.3304(9) 0.86872(17) 0.0255(7) Uani 1 1 d . . .
C2 C 0.1699(4) 0.3850(8) 0.94067(16) 0.0215(7) Uani 1 1 d . . .
H2 H 0.1185 0.5329 0.9677 0.026 Uiso 1 1 calc R . .
C3 C 0.3633(4) 0.4625(7) 0.92210(16) 0.0205(7) Uani 1 1 d . . .
C4 C 0.5333(4) 0.7578(9) 0.85108(16) 0.0241(7) Uani 1 1 d . . .
H4A H 0.6380 0.6938 0.8846 0.029 Uiso 1 1 calc R . .
H4B H 0.5393 0.9515 0.8497 0.029 Uiso 1 1 calc R . .
C5 C 0.5445(5) 0.6468(9) 0.77364(18) 0.0293(8) Uani 1 1 d . . .
H5A H 0.5491 0.4532 0.7765 0.035 Uiso 1 1 calc R . .
H5B H 0.6593 0.7074 0.7558 0.035 Uiso 1 1 calc R . .
C6 C 0.3833(5) 0.7277(11) 0.71762(17) 0.0320(9) Uani 1 1 d . . .
H6A H 0.3567 0.9156 0.7247 0.038 Uiso 1 1 calc R . .
H6B H 0.2742 0.6267 0.7277 0.038 Uiso 1 1 calc R . .
C7 C 0.4168(4) 0.6840(9) 0.63691(17) 0.0277(8) Uani 1 1 d . . .
H7A H 0.4576 0.5020 0.6295 0.033 Uiso 1 1 calc R . .
H7B H 0.3037 0.7161 0.6039 0.033 Uiso 1 1 calc R . .
C8 C 0.6743(4) 0.8114(7) 0.57063(15) 0.0183(6) Uani 1 1 d . . .
C9 C 0.8215(4) 1.0275(7) 0.56802(16) 0.0201(6) Uani 1 1 d . . .
H9 H 0.7640 1.1890 0.5449 0.024 Uiso 1 1 calc R . .
C10 C 0.9137(4) 1.0949(8) 0.64670(18) 0.0240(7) Uani 1 1 d . . .
H1 H 0.2836 0.0493 0.9855 0.047 Uiso 1 1 d . . .
H12 H 1.0229 1.0680 0.5091 0.047 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0146(9) 0.0601(18) 0.0427(11) 0.0092(12) -0.0026(7) -0.0103(11)
F2 0.0224(10) 0.0478(16) 0.0391(11) 0.0150(11) -0.0057(8) 0.0058(10)
F3 0.0297(11) 0.0514(17) 0.0271(9) -0.0092(10) -0.0017(7) 0.0021(11)
F4 0.0255(10) 0.0413(15) 0.0302(10) 0.0131(10) -0.0031(7) 0.0022(10)
F5 0.0312(11) 0.0458(15) 0.0281(9) -0.0170(10) 0.0058(7) 0.0030(11)
F6 0.0300(11) 0.0429(15) 0.0353(10) -0.0019(10) 0.0064(8) -0.0154(11)
O1 0.0150(10) 0.0414(18) 0.0277(11) 0.0121(11) 0.0045(7) 0.0006(11)
O2 0.0150(10) 0.0289(15) 0.0309(11) 0.0021(11) -0.0004(8) 0.0030(10)
O3 0.0149(10) 0.0330(15) 0.0240(10) 0.0056(10) 0.0047(7) 0.0040(10)
O4 0.0176(11) 0.0335(16) 0.0213(9) -0.0046(10) 0.0050(7) -0.0005(10)
O5 0.0331(13) 0.0208(14) 0.0260(11) -0.0021(10) 0.0074(9) -0.0001(10)
O6 0.0358(14) 0.0198(13) 0.0329(12) -0.0044(10) 0.0230(10) -0.0033(10)
C1 0.0144(14) 0.036(2) 0.0257(14) 0.0049(15) -0.0004(10) 0.0015(14)
C2 0.0120(13) 0.033(2) 0.0201(13) 0.0022(13) 0.0024(9) -0.0004(13)
C3 0.0194(14) 0.0272(19) 0.0152(12) -0.0044(12) 0.0022(10) -0.0009(12)
C4 0.0169(14) 0.032(2) 0.0235(13) 0.0025(13) 0.0044(10) -0.0047(13)
C5 0.0256(16) 0.037(2) 0.0254(15) 0.0007(14) 0.0044(11) 0.0023(15)
C6 0.0213(16) 0.048(3) 0.0264(15) 0.0038(16) 0.0019(11) -0.0026(17)
C7 0.0173(14) 0.042(2) 0.0240(14) -0.0028(15) 0.0008(10) -0.0054(15)
C8 0.0181(14) 0.0213(18) 0.0153(11) 0.0026(12) 0.0012(9) 0.0053(12)
C9 0.0246(15) 0.0176(17) 0.0188(13) 0.0007(11) 0.0057(11) 0.0071(12)
C10 0.0201(15) 0.027(2) 0.0251(14) -0.0009(13) 0.0052(11) 0.0000(13)

#----------------------------------------------------------------------------#
# 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
F1 C1 1.318(4) . no
F2 C1 1.333(5) . no
F3 C1 1.343(4) . no
F4 C10 1.333(4) . no
F5 C10 1.327(4) . no
F6 C10 1.332(4) . no
O1 C2 1.398(4) . no
O1 H1 0.9400 . no
O2 C3 1.210(4) . no
O3 C3 1.314(4) . no
O3 C4 1.460(4) . no
O4 C8 1.327(4) . no
O4 C7 1.464(4) . no
O5 C8 1.197(4) . no
O6 C9 1.396(4) . no
O6 H12 0.8800 . no
C1 C2 1.534(4) . no
C2 C3 1.523(4) . no
C2 H2 0.9800 . no
C4 C5 1.508(4) . no
C4 H4A 0.9700 . no
C4 H4B 0.9700 . no
C5 C6 1.511(4) . no
C5 H5A 0.9700 . no
C5 H5B 0.9700 . no
C6 C7 1.512(4) . no
C6 H6A 0.9700 . no
C6 H6B 0.9700 . no
C7 H7A 0.9700 . no
C7 H7B 0.9700 . no
C8 C9 1.521(5) . no
C9 C10 1.534(4) . no
C9 H9 0.9800 . no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 116.00 . . no
C3 O3 C4 118.0(3) . . no
C8 O4 C7 118.7(3) . . no
C9 O6 H12 110.00 . . no
F1 C1 F2 107.3(3) . . no
F1 C1 F3 107.7(3) . . no
F2 C1 F3 107.0(3) . . no
F1 C1 C2 111.3(3) . . no
F2 C1 C2 112.0(3) . . no
F3 C1 C2 111.5(3) . . no
O1 C2 C3 111.2(3) . . no
O1 C2 C1 108.4(3) . . no
C3 C2 C1 110.4(2) . . no
O1 C2 H2 108.9 . . no
C3 C2 H2 108.9 . . no
C1 C2 H2 108.9 . . no
O2 C3 O3 127.0(3) . . no
O2 C3 C2 121.0(3) . . no
O3 C3 C2 112.0(3) . . no
O3 C4 C5 110.1(3) . . no
O3 C4 H4A 109.6 . . no
C5 C4 H4A 109.6 . . no
O3 C4 H4B 109.6 . . no
C5 C4 H4B 109.6 . . no
H4A C4 H4B 108.1 . . no
C4 C5 C6 113.7(3) . . no
C4 C5 H5A 108.8 . . no
C6 C5 H5A 108.8 . . no
C4 C5 H5B 108.8 . . no
C6 C5 H5B 108.8 . . no
H5A C5 H5B 107.7 . . no
C5 C6 C7 114.1(3) . . no
C5 C6 H6A 108.7 . . no
C7 C6 H6A 108.7 . . no
C5 C6 H6B 108.7 . . no
C7 C6 H6B 108.7 . . no
H6A C6 H6B 107.6 . . no
O4 C7 C6 106.2(3) . . no
O4 C7 H7A 110.5 . . no
C6 C7 H7A 110.5 . . no
O4 C7 H7B 110.5 . . no
C6 C7 H7B 110.5 . . no
H7A C7 H7B 108.7 . . no
O5 C8 O4 126.2(3) . . no
O5 C8 C9 124.1(3) . . no
O4 C8 C9 109.7(3) . . no
O6 C9 C8 108.3(3) . . no
O6 C9 C10 109.0(3) . . no
C8 C9 C10 111.3(3) . . no
O6 C9 H9 109.4 . . no
C8 C9 H9 109.4 . . no
C10 C9 H9 109.4 . . no
F5 C10 F6 107.2(3) . . no
F5 C10 F4 107.9(3) . . no
F6 C10 F4 107.2(3) . . no
F5 C10 C9 112.6(3) . . no
F6 C10 C9 110.1(3) . . no
F4 C10 C9 111.6(3) . . no

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
F1 C1 C2 O1 44.6(4) . . . . no
F2 C1 C2 O1 164.7(3) . . . . no
F3 C1 C2 O1 -75.6(4) . . . . no
F1 C1 C2 C3 166.8(3) . . . . no
F2 C1 C2 C3 -73.2(4) . . . . no
F3 C1 C2 C3 46.6(4) . . . . no
C4 O3 C3 O2 5.7(5) . . . . no
C4 O3 C3 C2 -174.7(3) . . . . no
O1 C2 C3 O2 -1.7(4) . . . . no
C1 C2 C3 O2 -122.1(4) . . . . no
O1 C2 C3 O3 178.7(3) . . . . no
C1 C2 C3 O3 58.3(4) . . . . no
C3 O3 C4 C5 96.0(3) . . . . no
O3 C4 C5 C6 57.3(5) . . . . no
C4 C5 C6 C7 164.2(4) . . . . no
C8 O4 C7 C6 150.8(3) . . . . no
C5 C6 C7 O4 -67.9(5) . . . . no
C7 O4 C8 O5 5.6(5) . . . . no
C7 O4 C8 C9 -175.9(2) . . . . no
O5 C8 C9 O6 -12.2(4) . . . . no
O4 C8 C9 O6 169.2(2) . . . . no
O5 C8 C9 C10 -132.1(3) . . . . no
O4 C8 C9 C10 49.4(3) . . . . no
O6 C9 C10 F5 165.3(3) . . . . no
C8 C9 C10 F5 -75.3(4) . . . . no
O6 C9 C10 F6 45.7(4) . . . . no
C8 C9 C10 F6 165.1(3) . . . . no
O6 C9 C10 F4 -73.2(3) . . . . no
C8 C9 C10 F4 46.2(3) . . . . no

_diffrn_measured_fraction_theta_max 0.886
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.886
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.062
#==END
#----------------------------------------------------------------------------#
data_3b
_database_code_depnum_ccdc_archive 'CCDC 246919'
_audit_creation_method           SHELXL-97
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_formula_sum            'C11 H14 F6 O6 '
_chemical_formula_moiety         'C11 H14 F6 O6 '
_chemical_formula_weight         356.22
_chemical_melting_point          374
_chemical_name_common            
'(S,S)-(-)-pentamethylene bis(3,3,3-trifluorolactate)'
_chemical_absolute_configuration syn
_chemical_optical_rotation       '[\a]^25^~D~= -6.61 (c = 1.0, acetone)'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2 1'
_symmetry_Int_Tables_number      5

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

_cell_length_a                   18.816(3)
_cell_length_b                   5.1374(6)
_cell_length_c                   7.7556(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.202(2)
_cell_angle_gamma                90.00
_cell_volume                     745.31(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2375
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      25.3
_cell_measurement_temperature    296(2)

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_special_details           
;
A needle crystal was mounted on a glass capillary.
The data was collected at room temperature.
;
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_measurement_device_type  'Rigaku RAXIS-IV Imaging Plate'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            1816
_diffrn_reflns_av_R_equivalents  0.056
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         27.48
_reflns_number_total             839
_reflns_number_gt                553
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection       'RAPID-AUTO (Rigaku)'
_computing_cell_refinement       'PAPID-AUTO (Rigaku)'
_computing_data_reduction        'teXsan Ver. 1.11 (MSC)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'WinGX Ver. 1.7 (Farrugia, 1999)'
_computing_molecular_graphics    'Mercury Ver. 1.3 (Bruno et al., 2002)'

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

Non H-atoms were refined anisotropically.
H-atoms of OH have been located from Fourier difference maps
and fixed to its position.
The remaining H-atoms were included in calculated positions
and treated as riding atoms using the SHELXL default parameters.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1087P)^2^+0.0523P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.031(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 
; The absolute configuration was assigned to agree with
that of its precursor (S)-trifluorolactic acid at the chiral centre C2.
This compound has no atom heavier than Si and analyzed by
Mo radiation so that Flack parameter is not listed.
Friedel pairs were merged before refinement.
;
_refine_ls_number_reflns         839
_refine_ls_number_parameters     106
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1833
_refine_ls_wR_factor_gt          0.1641
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
#----------------------------------------------------------------------------#
# 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
F1 F -0.8904(2) -0.4573(12) -0.5876(5) 0.1154(16) Uani 1 1 d . . .
F2 F -0.9196(2) -0.0831(9) -0.5012(5) 0.1076(15) Uani 1 1 d . . .
F3 F -0.93860(17) -0.4184(11) -0.3524(4) 0.1013(15) Uani 1 1 d . . .
O1 O -0.7732(2) -0.1989(9) -0.4692(7) 0.0996(16) Uani 1 1 d . . .
O2 O -0.7885(2) 0.1209(9) -0.2069(5) 0.0840(13) Uani 1 1 d . . .
O3 O -0.8572(2) -0.1678(10) -0.0870(4) 0.0821(13) Uani 1 1 d . . .
C1 C -0.8924(3) -0.3105(14) -0.4475(7) 0.0750(15) Uani 1 1 d . . .
C2 C -0.8195(2) -0.2822(12) -0.3516(7) 0.0684(13) Uani 1 1 d . . .
H2 H -0.8034 -0.4505 -0.3023 0.082 Uiso 1 1 calc R . .
C3 C -0.8200(3) -0.0840(12) -0.2090(7) 0.0685(14) Uani 1 1 d . . .
C4 C -0.8654(4) 0.015(2) 0.0597(7) 0.102(3) Uani 1 1 d . . .
H4A H -0.8656 -0.0820 0.1667 0.122 Uiso 1 1 calc R . .
H4B H -0.8253 0.1351 0.0729 0.122 Uiso 1 1 calc R . .
C5 C -0.9315(4) 0.1606(16) 0.0264(8) 0.101(3) Uani 1 1 d . . .
H5A H -0.9287 0.2664 -0.0762 0.121 Uiso 1 1 calc R . .
H5B H -0.9351 0.2782 0.1230 0.121 Uiso 1 1 calc R . .
C6 C -1.0000 0.001(2) 0.0000 0.081(2) Uani 1 2 d S . .
H6A H -1.0021 -0.1110 0.1002 0.097 Uiso 0.50 1 calc PR . .
H6B H -0.9979 -0.1110 -0.1002 0.097 Uiso 0.50 1 calc PR . .
H1 H -0.7284 -0.2522 -0.4726 0.130 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.123(3) 0.139(4) 0.088(2) -0.029(3) 0.0271(19) -0.017(3)
F2 0.100(3) 0.115(3) 0.104(2) 0.019(3) -0.005(2) 0.024(3)
F3 0.0690(18) 0.157(4) 0.0790(18) 0.011(2) 0.0119(14) -0.039(2)
O1 0.087(3) 0.071(3) 0.153(4) -0.010(3) 0.073(2) -0.010(2)
O2 0.089(3) 0.079(3) 0.089(2) 0.001(2) 0.0324(19) -0.020(2)
O3 0.075(2) 0.105(3) 0.0677(19) 0.019(2) 0.0124(16) -0.024(2)
C1 0.077(3) 0.082(4) 0.067(3) 0.006(3) 0.013(2) -0.002(3)
C2 0.056(3) 0.057(3) 0.096(3) 0.013(3) 0.026(2) -0.002(2)
C3 0.047(2) 0.081(4) 0.077(3) 0.015(3) 0.005(2) 0.000(2)
C4 0.089(4) 0.158(8) 0.059(3) -0.007(4) 0.008(3) -0.041(5)
C5 0.142(6) 0.101(6) 0.066(3) -0.015(3) 0.035(3) -0.044(5)
C6 0.092(5) 0.090(7) 0.063(4) 0.000 0.019(4) 0.000

_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
F1 C1 1.326(8) . no
F2 C1 1.324(8) . no
F3 C1 1.321(7) . no
O1 C2 1.395(5) . no
O1 H1 0.8900 . no
O2 C3 1.207(7) . no
O3 C3 1.309(6) . no
O3 C4 1.497(9) . no
C1 C2 1.495(8) . no
C2 C3 1.504(9) . no
C2 H2 0.9800 . no
C4 C5 1.449(11) . no
C4 H4A 0.9700 . no
C4 H4B 0.9700 . no
C5 C6 1.523(9) . no
C5 H5A 0.9700 . no
C5 H5B 0.9700 . no
C6 C5 1.523(9) 2_355 no
C6 H6A 0.9700 . no
C6 H6B 0.9700 . no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 126.00 . . no
C3 O3 C4 116.7(5) . . no
F2 C1 F3 106.9(6) . . no
F2 C1 F1 106.7(4) . . no
F3 C1 F1 107.3(6) . . no
F2 C1 C2 111.9(5) . . no
F3 C1 C2 112.8(4) . . no
F1 C1 C2 111.0(5) . . no
O1 C2 C1 108.0(5) . . no
O1 C2 C3 109.1(4) . . no
C1 C2 C3 110.7(5) . . no
O1 C2 H2 109.7 . . no
C1 C2 H2 109.7 . . no
C3 C2 H2 109.7 . . no
O2 C3 O3 125.3(6) . . no
O2 C3 C2 123.9(5) . . no
O3 C3 C2 110.8(5) . . no
C5 C4 O3 110.2(4) . . no
C5 C4 H4A 109.6 . . no
O3 C4 H4A 109.6 . . no
C5 C4 H4B 109.6 . . no
O3 C4 H4B 109.6 . . no
H4A C4 H4B 108.1 . . no
C4 C5 C6 116.3(7) . . no
C4 C5 H5A 108.2 . . no
C6 C5 H5A 108.2 . . no
C4 C5 H5B 108.2 . . no
C6 C5 H5B 108.2 . . no
H5A C5 H5B 107.4 . . no
C5 C6 C5 114.7(10) . 2_355 no
C5 C6 H6A 108.6 . . no
C5 C6 H6A 108.6 2_355 . no
C5 C6 H6B 108.6 . . no
C5 C6 H6B 108.6 2_355 . no
H6A C6 H6B 107.6 . . no

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
F2 C1 C2 O1 -67.0(6) . . . . no
F3 C1 C2 O1 172.4(6) . . . . no
F1 C1 C2 O1 52.1(7) . . . . no
F2 C1 C2 C3 52.3(6) . . . . no
F3 C1 C2 C3 -68.3(7) . . . . no
F1 C1 C2 C3 171.4(5) . . . . no
C4 O3 C3 O2 4.7(8) . . . . no
C4 O3 C3 C2 -177.0(5) . . . . no
O1 C2 C3 O2 4.6(7) . . . . no
C1 C2 C3 O2 -114.0(6) . . . . no
O1 C2 C3 O3 -173.6(5) . . . . no
C1 C2 C3 O3 67.7(6) . . . . no
C3 O3 C4 C5 94.3(6) . . . . no
O3 C4 C5 C6 58.5(6) . . . . no
C4 C5 C6 C5 177.4(5) . . . 2_355 no

_diffrn_measured_fraction_theta_max 0.882
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.882
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.052
#==END
#----------------------------------------------------------------------------#
data_3c
_database_code_depnum_ccdc_archive 'CCDC 246920'
_audit_creation_method           SHELXL-97
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_formula_sum            'C12 H16 F6 O6 '
_chemical_formula_moiety         'C12 H16 F6 O6 '
_chemical_formula_weight         370.25
_chemical_melting_point          387
_chemical_name_common            
'(S,S)-(-)-hexamethylene bis(3,3,3-trifluorolactate)'
_chemical_absolute_configuration syn
_chemical_optical_rotation       '[\a]^25^~D~= -5.80 (c = 1.1, acetone)'
#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2 '
_symmetry_Int_Tables_number      18

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

_cell_length_a                   19.7519(12)
_cell_length_b                   5.0738(2)
_cell_length_c                   7.8915(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     790.86(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5322
_cell_measurement_theta_min      4.0
_cell_measurement_theta_max      27.5
_cell_measurement_temperature    120(1)

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_special_details           
;
A needle crystal was mounted on a glass capillary.
The crystal was cooled by cold nitrogen flux of a low temperature device
during the data collection.
;
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_T_max  0.984

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-IV Imaging Plate'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_reflns_number            5550
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1040
_reflns_number_gt                1015
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection       'RAPID-AUTO (Rigaku)'
_computing_cell_refinement       'PAPID-AUTO (Rigaku)'
_computing_data_reduction        'teXsan Ver. 1.11 (MSC)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'WinGX Ver. 1.7 (Farrugia, 1999)'
_computing_molecular_graphics    'Mercury Ver. 1.3 (Bruno et al., 2002)'

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

H-atom of OH has been located from
Fourier difference maps and fixed to its position, while
the remaining H-atoms were included in calculated positions
and treated as riding atoms using the SHELXL default parameters.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0532P)^2^+0.2184P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
; The absolute configuration was assigned to agree with
that of its precursor (S)-trifluorolactic acid at the chiral centre C2.
This compound has no atom heavier than Si and analyzed by
Mo radiation so that Flack parameter is not listed.
Friedel pairs were merged before refinement.
;
_refine_ls_number_reflns         1040
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#----------------------------------------------------------------------------#
# 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
F1 F 0.89718(8) 1.0820(4) -0.04990(18) 0.0495(4) Uani 1 1 d . . .
F2 F 0.93015(6) 1.0760(3) 0.20839(17) 0.0423(4) Uani 1 1 d . . .
F3 F 0.92198(7) 0.7143(3) 0.0671(2) 0.0510(4) Uani 1 1 d . . .
O1 O 0.78102(8) 0.8224(3) 0.01507(19) 0.0311(4) Uani 1 1 d . . .
O2 O 0.78433(7) 0.5194(3) 0.28767(18) 0.0269(3) Uani 1 1 d . . .
O3 O 0.84313(6) 0.8239(3) 0.43544(16) 0.0225(3) Uani 1 1 d . . .
C1 C 0.89290(11) 0.9475(4) 0.0940(3) 0.0300(4) Uani 1 1 d . . .
C2 C 0.81947(9) 0.9199(4) 0.1504(2) 0.0220(4) Uani 1 1 d . . .
H2 H 0.8019 1.0925 0.1848 0.026 Uiso 1 1 calc R . .
C3 C 0.81355(8) 0.7267(4) 0.2983(2) 0.0201(4) Uani 1 1 d . . .
C4 C 0.84296(9) 0.6566(5) 0.5871(2) 0.0268(4) Uani 1 1 d . . .
H4A H 0.8008 0.5588 0.5923 0.032 Uiso 1 1 calc R . .
H4B H 0.8459 0.7665 0.6874 0.032 Uiso 1 1 calc R . .
C5 C 0.90176(9) 0.4659(4) 0.5847(3) 0.0256(4) Uani 1 1 d . . .
H5A H 0.8981 0.3556 0.4847 0.031 Uiso 1 1 calc R . .
H5B H 0.8986 0.3521 0.6831 0.031 Uiso 1 1 calc R . .
C6 C 0.97098(9) 0.5985(4) 0.5845(3) 0.0246(4) Uani 1 1 d . . .
H6A H 0.9747 0.7100 0.4851 0.030 Uiso 1 1 calc R . .
H6B H 0.9748 0.7102 0.6838 0.030 Uiso 1 1 calc R . .
H1 H 0.7670 0.9321 -0.0500 0.047 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0573(8) 0.0622(10) 0.0290(7) 0.0155(7) -0.0019(6) -0.0178(9)
F2 0.0306(6) 0.0651(10) 0.0311(6) 0.0023(7) -0.0035(5) -0.0190(7)
F3 0.0439(7) 0.0502(9) 0.0589(10) 0.0012(9) 0.0204(7) 0.0141(7)
O1 0.0412(7) 0.0204(6) 0.0316(8) 0.0020(6) -0.0203(6) -0.0017(6)
O2 0.0292(6) 0.0216(6) 0.0298(7) -0.0008(6) -0.0027(6) -0.0043(6)
O3 0.0250(6) 0.0233(6) 0.0193(6) -0.0015(6) -0.0020(5) 0.0005(5)
C1 0.0321(9) 0.0345(11) 0.0234(9) 0.0043(9) -0.0007(7) -0.0025(9)
C2 0.0248(8) 0.0177(8) 0.0235(9) -0.0008(8) -0.0073(7) 0.0006(7)
C3 0.0166(7) 0.0212(8) 0.0224(8) -0.0029(7) -0.0004(6) 0.0023(6)
C4 0.0261(8) 0.0354(11) 0.0189(8) 0.0031(9) 0.0022(7) -0.0011(8)
C5 0.0273(9) 0.0273(9) 0.0223(8) 0.0045(8) 0.0010(7) -0.0020(8)
C6 0.0261(8) 0.0247(9) 0.0231(9) -0.0002(8) 0.0011(7) -0.0001(8)

#----------------------------------------------------------------------------#
# 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
F1 C1 1.327(2) . no
F2 C1 1.335(3) . no
F3 C1 1.332(3) . no
O1 C2 1.401(2) . no
O1 H1 0.8100 . no
O2 C3 1.203(2) . no
O3 C3 1.325(2) . no
O3 C4 1.467(2) . no
C1 C2 1.524(3) . no
C2 C3 1.528(3) . no
C2 H2 0.9800 . no
C4 C5 1.512(3) . no
C4 H4A 0.9700 . no
C4 H4B 0.9700 . no
C5 C6 1.524(3) . no
C5 H5A 0.9700 . no
C5 H5B 0.9700 . no
C6 C6 1.521(4) 2_765 no
C6 H6A 0.9700 . no
C6 H6B 0.9700 . no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 115.00 . . no
C3 O3 C4 116.74(15) . . no
F1 C1 F3 107.03(18) . . no
F1 C1 F2 107.00(17) . . no
F3 C1 F2 107.67(19) . . no
F1 C1 C2 110.99(17) . . no
F3 C1 C2 112.04(18) . . no
F2 C1 C2 111.84(17) . . no
O1 C2 C1 109.00(16) . . no
O1 C2 C3 108.32(15) . . no
C1 C2 C3 110.80(15) . . no
O1 C2 H2 109.6 . . no
C1 C2 H2 109.6 . . no
C3 C2 H2 109.6 . . no
O2 C3 O3 126.42(18) . . no
O2 C3 C2 122.99(17) . . no
O3 C3 C2 110.57(15) . . no
O3 C4 C5 110.99(14) . . no
O3 C4 H4A 109.4 . . no
C5 C4 H4A 109.4 . . no
O3 C4 H4B 109.4 . . no
C5 C4 H4B 109.4 . . no
H4A C4 H4B 108.0 . . no
C4 C5 C6 114.01(17) . . no
C4 C5 H5A 108.7 . . no
C6 C5 H5A 108.7 . . no
C4 C5 H5B 108.7 . . no
C6 C5 H5B 108.7 . . no
H5A C5 H5B 107.6 . . no
C6 C6 C5 112.7(2) 2_765 . no
C6 C6 H6A 109.0 2_765 . no
C5 C6 H6A 109.0 . . no
C6 C6 H6B 109.0 2_765 . no
C5 C6 H6B 109.0 . . no
H6A C6 H6B 107.8 . . no

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
F1 C1 C2 O1 51.2(2) . . . . no
F3 C1 C2 O1 -68.4(2) . . . . no
F2 C1 C2 O1 170.63(16) . . . . no
F1 C1 C2 C3 170.32(16) . . . . no
F3 C1 C2 C3 50.7(2) . . . . no
F2 C1 C2 C3 -70.3(2) . . . . no
C4 O3 C3 O2 3.1(3) . . . . no
C4 O3 C3 C2 -178.52(13) . . . . no
O1 C2 C3 O2 5.1(2) . . . . no
C1 C2 C3 O2 -114.37(19) . . . . no
O1 C2 C3 O3 -173.34(14) . . . . no
C1 C2 C3 O3 67.1(2) . . . . no
C3 O3 C4 C5 85.1(2) . . . . no
O3 C4 C5 C6 61.7(2) . . . . no
C4 C5 C6 C6 179.22(12) . . . 2_765 no

_diffrn_measured_fraction_theta_max 0.942
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.942
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.043
#==END
#----------------------------------------------------------------------------#
data_3d
_database_code_depnum_ccdc_archive 'CCDC 246921'
_audit_creation_method           SHELXL-97
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_formula_sum            'C13 H18 F6 O6 '
_chemical_formula_moiety         'C13 H18 F6 O6 '
_chemical_formula_weight         384.27
_chemical_melting_point          367
_chemical_name_common            
'(S,S)-(-)-heptamethylene bis(3,3,3-trifluorolactate)'
_chemical_absolute_configuration syn
_chemical_optical_rotation       '[\a]^25^~D~= -4.33 (c = 1.1, acetone)'
#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2 1'
_symmetry_Int_Tables_number      5

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

_cell_length_a                   20.8120(11)
_cell_length_b                   5.12790(10)
_cell_length_c                   7.9655(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.2790(10)
_cell_angle_gamma                90.00
_cell_volume                     844.99(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4678
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.5
_cell_measurement_temperature    296(2)
#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_special_details           
;
A needle crystal was mounted on a glass capillary.
The data was collected under room temperature.
;
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku rotating anode '
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-IV Imaging Plate'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            3952
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1032
_reflns_number_gt                1001
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection       'RAPID-AUTO (Rigaku)'
_computing_cell_refinement       'PAPID-AUTO (Rigaku)'
_computing_data_reduction        'teXsan Ver. 1.11 (MSC)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'WinGX Ver. 1.7 (Farrugia, 1999)'
_computing_molecular_graphics    'Mercury Ver. 1.3 (Bruno et al., 2002)'

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

Non H-atoms were refined anisotropically.
The disordered alkyl chain pairs (C6C8, C5C7) was observed and refined using
PART instruction of SHELXL with occupancy refinement flag.
(Without the PART instruction,
we could not refine the crystal structure anisotropically.)

H-atoms bearing the disordered alkyl chains were included in caluculated
positions and treated as riding atoms using the SHELXL default parameters.

H-atom of OH has included in calculated position.
The remaining H-atoms were located from Fourier difference map and
fixed to its position.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+0.3997P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 
; The absolute configuration was assigned to agree with
that of its precursor (S)-trifluorolactic acid at the chiral centre C2.
This compound has no atom heavier than Si and analyzed by
Mo radiation so that Flack parameter is not listed.
Friedel pairs were merged before refinement.
;
_refine_ls_number_reflns         1032
_refine_ls_number_parameters     126
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0697
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
#----------------------------------------------------------------------------#
# 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
F1 F 0.10415(7) 0.1916(4) 0.40434(15) 0.0559(5) Uani 1 1 d . . .
F2 F 0.06982(6) 0.2397(4) 0.64738(14) 0.0587(5) Uani 1 1 d . . .
F3 F 0.09096(7) 0.5747(3) 0.50271(17) 0.0522(4) Uani 1 1 d . . .
O1 O 0.22015(7) 0.4147(3) 0.50564(19) 0.0366(4) Uani 1 1 d . . .
H1 H 0.2378 0.2883 0.4676 0.055 Uiso 1 1 calc R . .
O2 O 0.21572(6) 0.7257(3) 0.76903(15) 0.0309(3) Uani 1 1 d . . .
O3 O 0.16382(5) 0.4227(3) 0.90850(14) 0.0226(3) Uani 1 1 d . A .
C1 C 0.11062(10) 0.3348(5) 0.5453(2) 0.0364(5) Uani 1 1 d . . .
C2 C 0.18021(8) 0.3306(4) 0.6264(2) 0.0264(4) Uani 1 1 d . . .
C3 C 0.18880(7) 0.5184(4) 0.7756(2) 0.0206(3) Uani 1 1 d . . .
C4 C 0.16720(8) 0.5852(4) 1.0610(2) 0.0274(4) Uani 1 1 d D . .
C5 C 0.12221(15) 0.7959(8) 1.0493(4) 0.0224(6) Uani 0.506(5) 1 d P A 1
H5A H 0.1279 0.8984 0.9496 0.027 Uiso 0.506(5) 1 calc PR A 1
H5B H 0.1314 0.9080 1.1471 0.027 Uiso 0.506(5) 1 calc PR A 1
C6 C 0.09388(16) 0.6661(8) 1.0846(4) 0.0224(6) Uani 0.502(5) 1 d P A 2
H6A H 0.0677 0.5097 1.0855 0.027 Uiso 0.502(5) 1 calc PR A 2
H6B H 0.0931 0.7524 1.1927 0.027 Uiso 0.502(5) 1 calc PR A 2
C7 C 0.05209(15) 0.7036(8) 1.0395(4) 0.0212(6) Uani 0.506(5) 1 d P A 1
H7A H 0.0451 0.6226 1.1461 0.025 Uiso 0.506(5) 1 calc PR A 1
H7B H 0.0451 0.5715 0.9523 0.025 Uiso 0.506(5) 1 calc PR A 1
C8 C 0.06478(14) 0.8459(7) 0.9454(4) 0.0212(6) Uani 0.490(5) 1 d P A 2
H8A H 0.0587 0.7547 0.8381 0.025 Uiso 0.490(5) 1 calc PR A 2
H8B H 0.0925 0.9956 0.9342 0.025 Uiso 0.490(5) 1 calc PR A 2
C9 C 0.0000 0.9305(7) 1.0000 0.0578(11) Uani 1 2 d S . .
H2 H 0.1894 0.1582 0.6648 0.027 Uiso 1 1 d . . .
H3 H 0.1721 0.4739 1.1566 0.043 Uiso 1 1 d . . .
H4 H 0.2039 0.6916 1.0635 0.066 Uiso 1 1 d D . .
H9 H 0.0042 1.0509 1.0867 0.072 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0787(10) 0.0592(11) 0.0320(6) -0.0185(7) 0.0158(6) -0.0252(9)
F2 0.0399(6) 0.1034(15) 0.0350(6) -0.0123(8) 0.0136(5) -0.0354(9)
F3 0.0497(8) 0.0584(11) 0.0458(7) -0.0068(7) -0.0072(6) 0.0155(7)
O1 0.0459(8) 0.0216(8) 0.0494(8) -0.0010(6) 0.0370(6) 0.0018(6)
O2 0.0337(6) 0.0301(8) 0.0297(6) 0.0034(6) 0.0076(5) -0.0138(6)
O3 0.0230(5) 0.0206(7) 0.0261(5) 0.0040(5) 0.0108(4) 0.0002(5)
C1 0.0421(10) 0.0434(14) 0.0255(8) -0.0103(9) 0.0120(7) -0.0118(10)
C2 0.0326(8) 0.0172(9) 0.0329(8) 0.0025(7) 0.0200(7) 0.0004(7)
C3 0.0143(6) 0.0202(9) 0.0282(7) 0.0065(7) 0.0060(5) 0.0012(7)
C4 0.0255(8) 0.0343(12) 0.0214(7) 0.0014(7) -0.0020(6) -0.0047(8)
C5 0.0212(13) 0.0258(15) 0.0214(10) -0.0017(9) 0.0079(8) -0.0015(9)
C6 0.0212(13) 0.0258(15) 0.0214(10) -0.0017(9) 0.0079(8) -0.0015(9)
C7 0.0207(11) 0.0189(12) 0.0250(10) 0.0026(9) 0.0068(8) -0.0002(9)
C8 0.0207(11) 0.0189(12) 0.0250(10) 0.0026(9) 0.0068(8) -0.0002(9)
C9 0.0337(15) 0.0131(15) 0.134(3) 0.000 0.0434(18) 0.000
#----------------------------------------------------------------------------#
# 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
F1 C1 1.336(2) . no
F2 C1 1.331(2) . no
F3 C1 1.329(3) . no
O1 C2 1.4063(19) . no
O1 H1 0.8200 . no
O2 C3 1.205(2) . no
O3 C3 1.3237(18) . no
O3 C4 1.468(2) . no
C1 C2 1.520(3) . no
C2 C3 1.524(2) . no
C2 H2 0.9500 . no
C4 C5 1.426(4) . no
C4 C6 1.612(4) . no
C4 H3 0.9500 . no
C4 H4 0.9400 . no
C5 C7 1.528(4) . no
C5 H5A 0.9700 . no
C5 H5B 0.9700 . no
C6 C8 1.516(5) . no
C6 H6A 0.9700 . no
C6 H6B 0.9700 . no
C7 C9 1.598(4) . no
C7 H7A 0.9700 . no
C7 H7B 0.9700 . no
C8 C9 1.524(3) . no
C8 H8A 0.9700 . no
C8 H8B 0.9700 . no
C9 C8 1.524(3) 2_557 no
C9 C7 1.598(4) 2_557 no
C9 H9 0.9200 . no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . no
C3 O3 C4 117.62(15) . . no
F3 C1 F2 107.2(2) . . no
F3 C1 F1 107.14(17) . . no
F2 C1 F1 107.44(18) . . no
F3 C1 C2 111.97(17) . . no
F2 C1 C2 112.12(16) . . no
F1 C1 C2 110.70(17) . . no
O1 C2 C1 108.14(15) . . no
O1 C2 C3 108.17(15) . . no
C1 C2 C3 110.35(14) . . no
O1 C2 H2 112.00 . . no
C1 C2 H2 107.00 . . no
C3 C2 H2 110.00 . . no
O2 C3 O3 125.93(17) . . no
O2 C3 C2 122.59(15) . . no
O3 C3 C2 111.49(15) . . no
C5 C4 O3 113.84(17) . . no
O3 C4 C6 106.39(16) . . no
C5 C4 H3 121.41(19) . . no
O3 C4 H3 108.00 . . no
C6 C4 H3 94.72(18) . . no
C5 C4 H4 95.0(2) . . no
O3 C4 H4 108.00 . . no
C6 C4 H4 128.8(2) . . no
H3 C4 H4 108.00 . . no
C4 C5 C7 112.6(3) . . no
C4 C5 H5A 109.1 . . no
C7 C5 H5A 109.1 . . no
C4 C5 H5B 109.1 . . no
C7 C5 H5B 109.1 . . no
H5A C5 H5B 107.8 . . no
C8 C6 C4 112.3(2) . . no
C8 C6 H6A 109.2 . . no
C4 C6 H6A 109.2 . . no
C8 C6 H6B 109.2 . . no
C4 C6 H6B 109.2 . . no
H6A C6 H6B 107.9 . . no
C5 C7 C9 114.1(3) . . no
C5 C7 H7A 108.7 . . no
C9 C7 H7A 108.7 . . no
C5 C7 H7B 108.7 . . no
C9 C7 H7B 108.7 . . no
H7A C7 H7B 107.6 . . no
C6 C8 C9 105.0(2) . . no
C6 C8 H8A 110.7 . . no
C9 C8 H8A 110.7 . . no
C6 C8 H8B 110.7 . . no
C9 C8 H8B 110.7 . . no
H8A C8 H8B 108.8 . . no
C8 C9 C8 146.9(4) . 2_557 no
C8 C9 C7 109.8(3) 2_557 . no
C7 C9 C7 86.5(3) 2_557 . no
C8 C9 H9 112.96(16) . . no
C8 C9 H9 89.47(13) 2_557 . no
C7 C9 H9 129.84(12) 2_557 . no
C7 C9 H9 109.48(14) . . no

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
F3 C1 C2 O1 -64.0(2) . . . . no
F2 C1 C2 O1 175.45(19) . . . . no
F1 C1 C2 O1 55.5(2) . . . . no
F3 C1 C2 C3 54.14(19) . . . . no
F2 C1 C2 C3 -66.4(2) . . . . no
F1 C1 C2 C3 173.62(17) . . . . no
C4 O3 C3 O2 1.9(2) . . . . no
C4 O3 C3 C2 -178.64(13) . . . . no
O1 C2 C3 O2 12.9(2) . . . . no
C1 C2 C3 O2 -105.23(18) . . . . no
O1 C2 C3 O3 -166.56(14) . . . . no
C1 C2 C3 O3 75.32(18) . . . . no
C3 O3 C4 C5 75.1(2) . . . . no
C3 O3 C4 C6 112.59(19) . . . . no
O3 C4 C5 C7 66.8(3) . . . . no
C6 C4 C5 C7 -18.3(2) . . . . no
C5 C4 C6 C8 41.1(3) . . . . no
O3 C4 C6 C8 -67.1(3) . . . . no
C4 C5 C7 C9 -171.75(19) . . . . no
C4 C6 C8 C9 -172.6(3) . . . . no
C6 C8 C9 C8 -54.8(2) . . . 2_557 no
C6 C8 C9 C7 -78.7(3) . . . 2_557 no
C6 C8 C9 C7 -19.3(2) . . . . no
C5 C7 C9 C8 40.1(3) . . . . no
C5 C7 C9 C8 -159.6(2) . . . 2_557 no
C5 C7 C9 C7 165.9(3) . . . 2_557 no

_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.956
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.031
#==END
#----------------------------------------------------------------------------#
data_3e
_database_code_depnum_ccdc_archive 'CCDC 246922'
_audit_creation_method           SHELXL-97
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_common            
'(S,S)-(-)-octamethylene bis(3,3,3-trifluorolactate)'
_chemical_melting_point          345
_chemical_formula_moiety         'C14 H20 F6 O6'
_chemical_formula_sum            'C14 H20 F6 O6'
_chemical_formula_weight         398.30
_chemical_absolute_configuration syn
_chemical_optical_rotation       '[\a]^25^~D~= -4.38 (c = 1.1, acetone)'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_Int_Tables_number      18

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

_cell_length_a                   22.9706(5)
_cell_length_b                   5.14600(10)
_cell_length_c                   8.0376(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     950.10(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    9550
_cell_measurement_theta_min      5.4
_cell_measurement_theta_max      50.0

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_special_details           
;
A platelet crystal was mounted on a glass capillary.
The crystal was cooled by cold nitrogen flux of a low temperature device
during the data collection.
;
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8920
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_process_details   
; ' (HIGASHI, T. (1995). Abscor - Empirical Absorption Correction
based on Fourier Series Approximation. Rigaku Corporation, Tokyo, Japan.)'
;
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-IV Imaging Plate'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            6670
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1053
_reflns_number_gt                990
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection       'RAPID-AUTO (Rigaku)'
_computing_cell_refinement       'PAPID-AUTO (Rigaku)'
_computing_data_reduction        'teXsan Ver. 1.11 (MSC)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'WinGX Ver. 1.7 (Farrugia, 1999)'
_computing_molecular_graphics    'Mercury Ver. 1.3 (Bruno et al., 2002)'

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

Non H-atoms were refined anisotropically.
H-atom of OH has been located from
Fourier difference maps and fixed to its position, while
the remaining H-atoms were included in calculated positions
and treated as riding atoms using the SHELXL default parameters.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0477P)^2^+0.1475P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
; The absolute configuration was assigned to agree with
that of its precursor (S)-trifluorolactic acid at the chiral centre C2.
This compound has no atom heavier than Si and analyzed by
Mo radiation so that Flack parameter is not listed.
Friedel pairs were merged before refinement.
;
_refine_ls_number_reflns         1053
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_restrained_S_all      1.217
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#----------------------------------------------------------------------------#
# 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
F1 F 0.88458(10) 0.7109(5) 0.4369(2) 0.0710(7) Uani 1 1 d . . .
F2 F 0.91272(8) 0.6839(7) 0.6896(2) 0.0806(9) Uani 1 1 d . . .
F3 F 0.89528(10) 0.3381(5) 0.5497(3) 0.0768(8) Uani 1 1 d . . .
O1 O 0.77939(10) 0.4974(4) 0.5026(2) 0.0420(5) Uani 1 1 d . . .
O2 O 0.77667(8) 0.2130(4) 0.7757(2) 0.0357(5) Uani 1 1 d . . .
O3 O 0.82988(7) 0.5034(3) 0.9182(2) 0.0271(4) Uani 1 1 d . . .
C1 C 0.87733(15) 0.5785(7) 0.5781(4) 0.0471(8) Uani 1 1 d . . .
C2 C 0.81433(12) 0.5856(5) 0.6335(3) 0.0308(6) Uani 1 1 d . . .
H2 H 0.8035 0.7642 0.6623 0.037 Uiso 1 1 calc R . .
C3 C 0.80494(11) 0.4093(5) 0.7835(3) 0.0246(6) Uani 1 1 d . . .
C4 C 0.82256(12) 0.3544(5) 1.0719(3) 0.0302(6) Uani 1 1 d . . .
H4A H 0.7828 0.2917 1.0786 0.036 Uiso 1 1 calc R . .
H4B H 0.8293 0.4674 1.1665 0.036 Uiso 1 1 calc R . .
C5 C 0.86357(11) 0.1270(5) 1.0807(3) 0.0306(6) Uani 1 1 d . . .
H5A H 0.8558 0.0127 0.9874 0.037 Uiso 1 1 calc R . .
H5B H 0.8556 0.0304 1.1818 0.037 Uiso 1 1 calc R . .
C6 C 0.92795(11) 0.2002(5) 1.0785(3) 0.0299(6) Uani 1 1 d . . .
H6A H 0.9360 0.3002 0.9789 0.036 Uiso 1 1 calc R . .
H6B H 0.9363 0.3098 1.1738 0.036 Uiso 1 1 calc R . .
C7 C 0.96796(12) -0.0348(5) 1.0828(4) 0.0326(6) Uani 1 1 d . . .
H7A H 0.9594 -0.1359 1.1817 0.039 Uiso 1 1 calc R . .
H7B H 0.9598 -0.1432 0.9869 0.039 Uiso 1 1 calc R . .
H10 H 0.7681 0.6183 0.4413 0.056 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0896(15) 0.0913(17) 0.0322(9) 0.0224(13) -0.0021(10) -0.0342(15)
F2 0.0575(11) 0.147(2) 0.0369(10) 0.0138(14) -0.0087(9) -0.0501(16)
F3 0.0639(13) 0.0862(17) 0.0802(17) 0.0140(15) 0.0255(13) 0.0257(14)
O1 0.0603(12) 0.0299(9) 0.0358(10) 0.0061(10) -0.0258(10) 0.0017(11)
O2 0.0430(11) 0.0337(10) 0.0305(10) -0.0008(9) -0.0064(9) -0.0125(10)
O3 0.0350(9) 0.0233(8) 0.0230(8) -0.0029(9) -0.0046(8) 0.0000(8)
C1 0.0567(19) 0.062(2) 0.0229(14) 0.0072(16) -0.0012(14) -0.0138(19)
C2 0.0425(14) 0.0200(11) 0.0300(13) -0.0009(11) -0.0101(12) 0.0021(13)
C3 0.0239(12) 0.0236(12) 0.0263(13) -0.0059(11) -0.0025(11) 0.0019(12)
C4 0.0340(13) 0.0346(14) 0.0219(12) -0.0024(13) 0.0011(12) 0.0004(13)
C5 0.0394(14) 0.0258(12) 0.0268(13) 0.0022(13) -0.0011(12) -0.0024(13)
C6 0.0379(14) 0.0223(11) 0.0295(13) -0.0021(12) -0.0009(12) 0.0004(12)
C7 0.0405(14) 0.0252(13) 0.0322(13) 0.0008(14) -0.0009(13) -0.0018(12)

#----------------------------------------------------------------------------#
# 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
F1 C1 1.334(4) . no
F2 C1 1.326(4) . no
F3 C1 1.324(4) . no
O1 C2 1.399(3) . no
O1 H10 0.8300 . no
O2 C3 1.203(3) . no
O3 C3 1.318(3) . no
O3 C4 1.464(3) . no
C1 C2 1.515(5) . no
C2 C3 1.524(4) . no
C2 H2 0.9800 . no
C4 C5 1.504(3) . no
C4 H4A 0.9700 . no
C4 H4B 0.9700 . no
C5 C6 1.526(4) . no
C5 H5A 0.9700 . no
C5 H5B 0.9700 . no
C6 C7 1.519(4) . no
C6 H6A 0.9700 . no
C6 H6B 0.9700 . no
C7 C7 1.515(5) 2_755 no
C7 H7A 0.9700 . no
C7 H7B 0.9700 . no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H10 112.00 . . no
C3 O3 C4 116.83(19) . . no
F3 C1 F2 107.9(3) . . no
F3 C1 F1 106.9(3) . . no
F2 C1 F1 106.8(3) . . no
F3 C1 C2 111.8(3) . . no
F2 C1 C2 112.2(3) . . no
F1 C1 C2 110.9(3) . . no
O1 C2 C1 108.6(2) . . no
O1 C2 C3 108.7(2) . . no
C1 C2 C3 110.7(2) . . no
O1 C2 H2 109.6 . . no
C1 C2 H2 109.6 . . no
C3 C2 H2 109.6 . . no
O2 C3 O3 125.9(2) . . no
O2 C3 C2 122.4(2) . . no
O3 C3 C2 111.7(2) . . no
O3 C4 C5 112.1(2) . . no
O3 C4 H4A 109.2 . . no
C5 C4 H4A 109.2 . . no
O3 C4 H4B 109.2 . . no
C5 C4 H4B 109.2 . . no
H4A C4 H4B 107.9 . . no
C4 C5 C6 114.5(2) . . no
C4 C5 H5A 108.6 . . no
C6 C5 H5A 108.6 . . no
C4 C5 H5B 108.6 . . no
C6 C5 H5B 108.6 . . no
H5A C5 H5B 107.6 . . no
C7 C6 C5 112.9(2) . . no
C7 C6 H6A 109.0 . . no
C5 C6 H6A 109.0 . . no
C7 C6 H6B 109.0 . . no
C5 C6 H6B 109.0 . . no
H6A C6 H6B 107.8 . . no
C7 C7 C6 113.6(3) 2_755 . no
C7 C7 H7A 108.9 2_755 . no
C6 C7 H7A 108.9 . . no
C7 C7 H7B 108.9 2_755 . no
C6 C7 H7B 108.9 . . no
H7A C7 H7B 107.7 . . no

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
F3 C1 C2 O1 -64.9(3) . . . . no
F2 C1 C2 O1 173.7(3) . . . . no
F1 C1 C2 O1 54.3(3) . . . . no
F3 C1 C2 C3 54.3(3) . . . . no
F2 C1 C2 C3 -67.1(3) . . . . no
F1 C1 C2 C3 173.6(2) . . . . no
C4 O3 C3 O2 0.2(4) . . . . no
C4 O3 C3 C2 178.42(19) . . . . no
O1 C2 C3 O2 7.6(3) . . . . no
C1 C2 C3 O2 -111.6(3) . . . . no
O1 C2 C3 O3 -170.7(2) . . . . no
C1 C2 C3 O3 70.1(3) . . . . no
C3 O3 C4 C5 80.0(3) . . . . no
O3 C4 C5 C6 61.2(3) . . . . no
C4 C5 C6 C7 -178.4(2) . . . . no
C5 C6 C7 C7 -179.30(17) . . . 2_755 no

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.29
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.049
#==END
#----------------------------------------------------------------------------#
data_3f_octane_solvate
_database_code_depnum_ccdc_archive 'CCDC 246923'
_audit_creation_method           SHELXL-97

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_melting_point          322
_chemical_formula_moiety         'C15 H22 F6 O6, (C8 H18)0.28'
_chemical_formula_sum            'C17.24 H27.04 F6 O6'
_chemical_formula_weight         444.51
_chemical_name_common            
;(S,S)-(-)-nonamethylene bis(3,3,3-trifluorolactate) octane
solvate
;
_chemical_absolute_configuration syn
_chemical_optical_rotation       '[\a]^25^~D~= -3.93 (c = 1.1, acetone)'
#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2 1'
_symmetry_Int_Tables_number      5

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

_cell_length_a                   27.753(11)
_cell_length_b                   4.9906(10)
_cell_length_c                   7.992(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.942(5)
_cell_angle_gamma                90.00
_cell_volume                     1101.0(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4015
_cell_measurement_theta_min      3.7
_cell_measurement_theta_max      27.3
_cell_measurement_temperature    150(1)

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             465
_exptl_special_details           
;
The single crystal was prepared by slow evaporation of a octane-THF solution.
A needle crystal was mounted on a glass capillary.

^1^H NMR analysis of 3f crystal dissolved in CDCl~3~ showed
inclusion of octane molecule.
(3f[mol] : octane[mol] = 1 : 0.27)

TG analysis of the crystal also showed inclusion and guest escape.
(3f[mol] : octane[mol] = 1 : 0.33)

In this X-ray diffraction analysis,
there were four residual peaks within the void from Fourier difference map.
However, the highly disordered solvents within the void were not
crystallographically well defined.

The SQUEEZE routine of the program PLATON estimated
a void electron population to be 37 (43.2 + 2 - 8.2) per unit cell.

Octane has 66 electrons per one molecule. Z value of the crystal is 2.
Amount of octane in 3f crystal was calculated as follows,
(3f[mol] : octane[mol] = 1 : 0.28)

The calculated value from SQUEEZE result was nearly consistent with
the NMR and TG results.
Therefore, the octane solvate formula based on the SQUEEZE result,
C15H22F6O6 + (C8H18)0.28 was adopted
for calculation of the related crystallographic parameters,
;

#_chemical_formula_sum 'C17.24H27.24F6O6'
#_chemical_formula_moiety 'C15H22F6O6, (C8H18)0.28'
#_chemical_formula_weight 444.51
#_exptl_crystal_density_diffrn 1.341
#_exptl_crystal_F_000 465
_exptl_absorpt_coefficient_mu    0.131

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
#_exptl_absorpt_coefficient_mu 0.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
(HIGASHI, T. (1995). Abscor - Empirical Absorption Correction
based on Fourier Series Approximation. Rigaku Corporation, Tokyo, Japan.)
;
_exptl_absorpt_correction_T_min  0.570
_exptl_absorpt_correction_T_max  0.987

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-IV Imaging Plate'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_reflns_number            2928
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.70
_diffrn_reflns_theta_max         25.33
_reflns_number_total             1068
_reflns_number_gt                992
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection       'RAPID-AUTO (Rigaku)'
_computing_cell_refinement       'PAPID-AUTO (Rigaku)'
_computing_data_reduction        'teXsan Ver. 1.11 (MSC)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'WinGX Ver. 1.7 (Farrugia, 1999)'
_computing_molecular_graphics    'Mercury Ver. 1.3 (Bruno et al., 2002)'

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

Non H-atoms were refined anisotropically.
H-atoms of OH have been located in calculated positions.
The remaining H-atoms were included in calculated positions
and treated as riding atoms using the SHELXL default parameters.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1104P)^2^+0.2214P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.014(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 
; The absolute configuration was assigned to agree with
that of its precursor (S)-trifluorolactic acid at the chiral centre C2.
This compound has no atom heavier than Si and analyzed by
Mo radiation so that Flack parameter is not listed.
Friedel pairs were merged before refinement.
;
_refine_ls_number_reflns         1068
_refine_ls_number_parameters     125
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1481
_refine_ls_wR_factor_gt          0.1437
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#----------------------------------------------------------------------------#
# DISORDER FIELD INFORMATION #
#----------------------------------------------------------------------------#
# SQUEEZE RESULTS
_platon_squeeze_details          
;
Although there were four peaks within the void from Fourier difference map,
the highly disordered solvents within the void were not crystallographically
well defined.

The SQUEEZE routine of the program PLATON was used
in order to eliminate the contribution of disordered solvents molecules,
thereby a final model based only on the ordered part of the crystal structure
was obtained.

The SQUEEZE routine suggested that
a total potential solvent area volume of 184.2 Ang^3^[16.7% of cell volume],
and a void electron population 37 per cell.

Refinement after the SQUEEZE routine gave significantly improved R values.
[R values before SQUEEZE]
R1 = 0.103 for >2sigma(I) data
R1 = 0.117 , wR2 = 0.322 , GooF = S = 1.62 for all data
( 1072 data and 0 restraint / 125 parameters)

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 -0.027 0.000 92.6 21.6
2 0.500 -0.050 0.000 92.6 21.6
_platon_squeeze_details
;
#----------------------------------------------------------------------------#
# 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
F1 F -0.14454(11) -0.6643(6) 0.0867(3) 0.0761(9) Uani 1 1 d . . .
F2 F -0.13019(10) -0.2785(6) -0.0166(3) 0.0770(9) Uani 1 1 d . . .
F3 F -0.11835(8) -0.6353(7) -0.1543(2) 0.0742(9) Uani 1 1 d . . .
O1 O -0.22817(11) -0.4173(5) -0.0130(3) 0.0581(8) Uani 1 1 d . . .
H1 H -0.2433 -0.5433 0.0218 0.068 Uiso 1 1 calc R . .
O2 O -0.22522(8) -0.1036(5) -0.2809(3) 0.0438(6) Uani 1 1 d . . .
O3 O -0.18321(7) -0.4155(5) -0.4101(2) 0.0383(6) Uani 1 1 d . . .
C1 C -0.14756(15) -0.5230(8) -0.0547(4) 0.0522(9) Uani 1 1 d . . .
C2 C -0.19971(12) -0.5086(7) -0.1351(4) 0.0398(7) Uani 1 1 d . . .
H2 H -0.2106 -0.6874 -0.1731 0.048 Uiso 1 1 calc R . .
C3 C -0.20449(9) -0.3156(7) -0.2836(4) 0.0339(6) Uani 1 1 d . . .
C4 C -0.18260(11) -0.2416(8) -0.5602(3) 0.0427(8) Uani 1 1 d . . .
H4A H -0.2111 -0.1282 -0.5711 0.051 Uiso 1 1 calc R . .
H4B H -0.1832 -0.3516 -0.6605 0.051 Uiso 1 1 calc R . .
C5 C -0.13774(10) -0.0703(8) -0.5437(3) 0.0423(8) Uani 1 1 d . . .
H5A H -0.1379 0.0414 -0.4444 0.051 Uiso 1 1 calc R . .
H5B H -0.1384 0.0471 -0.6407 0.051 Uiso 1 1 calc R . .
C6 C -0.09108(11) -0.2336(8) -0.5305(4) 0.0437(8) Uani 1 1 d . . .
H6A H -0.0909 -0.3453 -0.6297 0.052 Uiso 1 1 calc R . .
H6B H -0.0903 -0.3507 -0.4333 0.052 Uiso 1 1 calc R . .
C7 C -0.04583(11) -0.0577(9) -0.5141(5) 0.0526(9) Uani 1 1 d . . .
H7A H -0.0463 0.0584 -0.6116 0.063 Uiso 1 1 calc R . .
H7B H -0.0459 0.0547 -0.4151 0.063 Uiso 1 1 calc R . .
C8 C 0.0000 -0.2264(12) -0.5000 0.0532(12) Uani 1 2 d S . .
H8A H 0.0004 -0.3409 -0.4018 0.064 Uiso 0.50 1 calc PR . .
H8B H -0.0004 -0.3409 -0.5982 0.064 Uiso 0.50 1 calc PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.109(2) 0.0807(19) 0.0412(10) 0.0180(12) 0.0191(11) 0.0213(17)
F2 0.0828(16) 0.0705(19) 0.0726(15) 0.0021(13) -0.0166(13) -0.0206(14)
F3 0.0585(12) 0.121(2) 0.0452(10) 0.0144(13) 0.0157(9) 0.0359(15)
O1 0.0798(17) 0.0364(13) 0.0677(16) 0.0008(11) 0.0540(14) 0.0017(12)
O2 0.0470(11) 0.0394(13) 0.0475(11) -0.0041(10) 0.0165(9) 0.0048(9)
O3 0.0360(9) 0.0464(14) 0.0343(10) -0.0044(9) 0.0129(8) 0.0040(9)
C1 0.070(2) 0.052(2) 0.0355(16) 0.0061(14) 0.0103(14) 0.0061(18)
C2 0.0494(15) 0.0308(16) 0.0435(15) -0.0045(12) 0.0255(13) -0.0002(13)
C3 0.0274(11) 0.0389(16) 0.0370(14) -0.0072(12) 0.0113(9) -0.0031(12)
C4 0.0383(14) 0.059(2) 0.0315(13) 0.0020(13) 0.0053(10) 0.0079(14)
C5 0.0412(15) 0.048(2) 0.0390(14) 0.0097(14) 0.0124(11) 0.0098(14)
C6 0.0393(16) 0.0459(19) 0.0476(16) 0.0010(13) 0.0134(12) 0.0061(13)
C7 0.0398(16) 0.050(2) 0.071(2) 0.0057(17) 0.0195(15) 0.0021(15)
C8 0.039(2) 0.056(3) 0.067(3) 0.000 0.018(2) 0.000

#----------------------------------------------------------------------------#
# 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
F1 C1 1.327(4) . no
F2 C1 1.336(5) . no
F3 C1 1.319(4) . no
O1 C2 1.394(3) . no
O1 H1 0.8200 . no
O2 C3 1.206(4) . no
O3 C3 1.320(3) . no
O3 C4 1.482(4) . no
C1 C2 1.523(5) . no
C2 C3 1.523(5) . no
C2 H2 0.9800 . no
C4 C5 1.505(5) . no
C4 H4A 0.9700 . no
C4 H4B 0.9700 . no
C5 C6 1.524(4) . no
C5 H5A 0.9700 . no
C5 H5B 0.9700 . no
C6 C7 1.527(5) . no
C6 H6A 0.9700 . no
C6 H6B 0.9700 . no
C7 C8 1.520(4) . no
C7 H7A 0.9700 . no
C7 H7B 0.9700 . no
C8 C7 1.520(4) 2_554 no
C8 H8A 0.9700 . no
C8 H8B 0.9700 . no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . no
C3 O3 C4 116.2(2) . . no
F3 C1 F1 107.4(3) . . no
F3 C1 F2 107.2(4) . . no
F1 C1 F2 107.6(3) . . no
F3 C1 C2 112.4(3) . . no
F1 C1 C2 111.0(3) . . no
F2 C1 C2 111.0(3) . . no
O1 C2 C3 109.2(3) . . no
O1 C2 C1 107.6(3) . . no
C3 C2 C1 111.2(3) . . no
O1 C2 H2 109.6 . . no
C3 C2 H2 109.6 . . no
C1 C2 H2 109.6 . . no
O2 C3 O3 126.7(3) . . no
O2 C3 C2 123.0(2) . . no
O3 C3 C2 110.3(3) . . no
O3 C4 C5 109.9(2) . . no
O3 C4 H4A 109.7 . . no
C5 C4 H4A 109.7 . . no
O3 C4 H4B 109.7 . . no
C5 C4 H4B 109.7 . . no
H4A C4 H4B 108.2 . . no
C4 C5 C6 113.0(3) . . no
C4 C5 H5A 109.0 . . no
C6 C5 H5A 109.0 . . no
C4 C5 H5B 109.0 . . no
C6 C5 H5B 109.0 . . no
H5A C5 H5B 107.8 . . no
C5 C6 C7 112.6(3) . . no
C5 C6 H6A 109.1 . . no
C7 C6 H6A 109.1 . . no
C5 C6 H6B 109.1 . . no
C7 C6 H6B 109.1 . . no
H6A C6 H6B 107.8 . . no
C8 C7 C6 111.2(3) . . no
C8 C7 H7A 109.4 . . no
C6 C7 H7A 109.4 . . no
C8 C7 H7B 109.4 . . no
C6 C7 H7B 109.4 . . no
H7A C7 H7B 108.0 . . no
C7 C8 C7 112.7(4) 2_554 . no
C7 C8 H8A 109.1 2_554 . no
C7 C8 H8A 109.1 . . no
C7 C8 H8B 109.1 2_554 . no
C7 C8 H8B 109.1 . . no
H8A C8 H8B 107.8 . . no

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
F3 C1 C2 O1 173.0(3) . . . . no
F1 C1 C2 O1 52.6(4) . . . . no
F2 C1 C2 O1 -66.9(4) . . . . no
F3 C1 C2 C3 -67.5(4) . . . . no
F1 C1 C2 C3 172.2(3) . . . . no
F2 C1 C2 C3 52.6(4) . . . . no
C4 O3 C3 O2 3.6(4) . . . . no
C4 O3 C3 C2 -176.6(2) . . . . no
O1 C2 C3 O2 8.2(4) . . . . no
C1 C2 C3 O2 -110.3(3) . . . . no
O1 C2 C3 O3 -171.6(2) . . . . no
C1 C2 C3 O3 69.9(3) . . . . no
C3 O3 C4 C5 90.0(3) . . . . no
O3 C4 C5 C6 60.8(3) . . . . no
C4 C5 C6 C7 179.9(3) . . . . no
C5 C6 C7 C8 179.6(2) . . . . no
C6 C7 C8 C7 179.2(3) . . . 2_554 no

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        25.33
_diffrn_measured_fraction_theta_full 0.947
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.054
#==END
#----------------------------------------------------------------------------#
data_3g_hexane_ether_mixed_solvate
_database_code_depnum_ccdc_archive 'CCDC 246924'
_audit_creation_method           SHELXL-97
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_melting_point          339
_chemical_formula_moiety         'C16 H24 F6 O6, (C6H14)0.30, (C4H10O)0.08'
_chemical_formula_sum            'C18.12 H29 F6 O6.08'
_chemical_formula_weight         458.13
_chemical_name_common            
;(S,S)-(-)-decamethylene bis(3,3,3-trifluorolactate) hexane
ether mixed solvate
;
_chemical_absolute_configuration syn
_chemical_optical_rotation       '[\a]^25^~D~= -3.78 (c = 1.1, acetone)'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2 '
_symmetry_Int_Tables_number      18

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

_cell_length_a                   28.6832(8)
_cell_length_b                   5.0572(1)
_cell_length_c                   7.9245(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1149.50(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    13317
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      27.5

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             481
_exptl_special_details           
;
The single crystal was prepared by slow evaporation of a hexane-ether solution.
A needle crystal was mounted on a glass capillary.

^1^H NMR analysis of the crystal 3g (dissolved in CDCl~3~) showed
inclusion of hexane and ether.
(3g[mol] : hexane[mol] : ether[mol] = 1 : 0.30 : 0.08)

TG analysis of the crystal also showed inclusion and guest escape.
(3g[mol] : hexane+ether[mol] = 1 : 0.35-0.40)

In this X-ray diffraction analysis,
there were four residual peaks within the void from Fourier difference map.
However, the highly disordered solvents within the void could not be
crystallographically defined.

The SQUEEZE routine of the program PLATON estimated
a void electron count to be 73 per unit cell.

Hexane and ether have 50 and 40 electrons per one molecule, respectively.
Z value of the crystal is 2.
Amount of guests in 3g crystal was calculated as follows,
(3g[mol] : hexane+ether[mol] = 1 : 0.71-0.89)
This is larger than the results of NMR and TG analysis.

The estimate by SQUEEZE may be unreliable because
missing reflections can bias the estimate of the electron count by SQUEEZE.

Therefore, the solvate formula based on the result of NMR analysis,
C16H24F6O6, (C6H14)~0.30~(C4H10O)~0.08~
was adopted for calculation of the related crystallographic parameters,
;
#_chemical_formula_sum 'C18.12H29F6O6.08'
#_chemical_formula_moiety 'C16H24F6O6, (C6H14)0.3, (C4H10O)0.08'
#_chemical_formula_weight 458.13
#_exptl_crystal_density_diffrn 1.324
#_exptl_crystal_F_000 481
#_exptl_absorpt_coefficient_mu 0.128

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   
;
(HIGASHI, T. (1995). Abscor - Empirical Absorption Correction
based on Fourier Series Approximation. Rigaku Corporation, Tokyo, Japan.)
;

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-IV Imaging Plate'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            2511
_diffrn_reflns_av_R_equivalents  0.0086
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         27.50
_reflns_number_total             1274
_reflns_number_gt                1200
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection       'RAPID-AUTO (Rigaku)'
_computing_cell_refinement       'PAPID-AUTO (Rigaku)'
_computing_data_reduction        'teXsan Ver. 1.11 (MSC)'
_computing_structure_solution    'SAPI91 (Rigaku, 1991)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'WinGX Ver. 1.7 (Farrugia, 1999)'
_computing_molecular_graphics    'Mercury Ver. 1.3 (Bruno et al., 2002)'

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

Non H-atoms were refined anisotropically.
H-atoms of OH have been located from Fourier difference maps
and fixed to its position.
The remaining H-atoms were included in calculated positions
and treated as riding atoms using the SHELXL default parameters.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.1844P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.046(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 
; The absolute configuration was assigned to agree with
that of its precursor (S)-trifluorolactic acid at the chiral centre C2.
This compound has no atom heavier than Si and analyzed by
Mo radiation so that Flack parameter is not listed.
Friedel pairs were merged before refinement.
;
_refine_ls_number_reflns         1274
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#----------------------------------------------------------------------------#
# DISORDER FIELD INFORMATION #
#----------------------------------------------------------------------------#
# SQUEEZE RESULTS
_platon_squeeze_details          
;
Although there were four peaks within the void from Fourier difference map,
the highly disordered solvents within the void were not crystallographically
well defined.

The SQUEEZE routine of the program PLATON was used
in order to eliminate the contribution of disordered solvents molecules,
thereby a final model based only on the ordered part of the crystal structure
was obtained.

The SQUEEZE routine suggested that
a total potential solvent area volume of 206.9 Ang^3^[18.0% of cell volume],
and a void electron population of 73 per cell.

Refinement after the SQUEEZE routine gave significantly improved R values.
[R values before SQUEEZE]
R1 = 0.121 for >2sigma(I) data
R1 = 0.142 , wR2 = 0.360, GooF = S = 1.83 for all data
( 1496 data and 0 restraint / 128 parameters)

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 -0.051 0.078 102.8 36.7
2 0.500 -0.048 -0.078 102.8 36.7
_platon_squeeze_details
;
#----------------------------------------------------------------------------#
# 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
F1 F 0.14329(5) 0.2442(3) -0.05708(17) 0.0447(4) Uani 1 1 d . . .
F2 F 0.13264(5) 0.6214(3) 0.0598(2) 0.0485(4) Uani 1 1 d . . .
F3 F 0.12136(5) 0.2628(4) 0.20115(17) 0.0505(5) Uani 1 1 d . . .
O1 O 0.22652(6) 0.4749(3) 0.00716(17) 0.0293(4) Uani 1 1 d . . .
O2 O 0.22802(5) 0.7685(3) 0.28282(18) 0.0252(3) Uani 1 1 d . . .
O3 O 0.18564(4) 0.4694(3) 0.42813(17) 0.0206(3) Uani 1 1 d . . .
C1 C 0.14860(8) 0.3781(5) 0.0871(3) 0.0312(5) Uani 1 1 d . . .
C2 C 0.19943(7) 0.3809(4) 0.1413(3) 0.0221(4) Uani 1 1 d . . .
H2 H 0.2093 0.2016 0.1714 0.027 Uiso 1 1 calc R . .
C3 C 0.20618(6) 0.5650(4) 0.2914(2) 0.0198(4) Uani 1 1 d . . .
C4 C 0.18910(7) 0.6285(4) 0.5823(3) 0.0229(4) Uani 1 1 d . . .
H4A H 0.2200 0.7054 0.5895 0.027 Uiso 1 1 calc R . .
H4B H 0.1847 0.5152 0.6798 0.027 Uiso 1 1 calc R . .
C5 C 0.15310(6) 0.8467(4) 0.5851(3) 0.0232(4) Uani 1 1 d . . .
H5A H 0.1581 0.9603 0.4881 0.028 Uiso 1 1 calc R . .
H5B H 0.1578 0.9528 0.6856 0.028 Uiso 1 1 calc R . .
C6 C 0.10295(7) 0.7499(4) 0.5827(3) 0.0245(4) Uani 1 1 d . . .
H6A H 0.0977 0.6357 0.6792 0.029 Uiso 1 1 calc R . .
H6B H 0.0978 0.6461 0.4814 0.029 Uiso 1 1 calc R . .
C7 C 0.06792(7) 0.9771(4) 0.5873(3) 0.0263(4) Uani 1 1 d . . .
H7A H 0.0733 1.0811 0.6884 0.032 Uiso 1 1 calc R . .
H7B H 0.0732 1.0910 0.4907 0.032 Uiso 1 1 calc R . .
C8 C 0.01740(6) 0.8849(4) 0.5855(3) 0.0272(5) Uani 1 1 d . . .
H8A H 0.0118 0.7751 0.6838 0.033 Uiso 1 1 calc R . .
H8B H 0.0122 0.7772 0.4860 0.033 Uiso 1 1 calc R . .
H1 H 0.2397 0.3546 -0.0484 0.050 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0575(8) 0.0559(9) 0.0207(6) -0.0135(7) 0.0006(6) -0.0173(8)
F2 0.0409(7) 0.0493(8) 0.0552(10) -0.0090(8) -0.0158(7) 0.0134(6)
F3 0.0428(7) 0.0853(12) 0.0233(7) -0.0060(8) 0.0065(6) -0.0325(8)
O1 0.0412(8) 0.0228(7) 0.0237(7) -0.0014(7) 0.0182(6) 0.0001(6)
O2 0.0289(7) 0.0242(7) 0.0226(7) 0.0020(6) 0.0032(6) -0.0072(6)
O3 0.0265(6) 0.0193(6) 0.0159(6) 0.0003(6) 0.0033(6) -0.0011(5)
C1 0.0357(11) 0.0395(12) 0.0183(9) -0.0063(10) 0.0030(9) -0.0075(10)
C2 0.0299(10) 0.0176(9) 0.0188(9) 0.0011(8) 0.0082(8) 0.0004(8)
C3 0.0204(8) 0.0214(9) 0.0176(9) 0.0031(8) 0.0010(8) 0.0022(7)
C4 0.0260(9) 0.0277(10) 0.0149(8) -0.0033(8) -0.0007(8) -0.0014(8)
C5 0.0276(9) 0.0223(9) 0.0198(9) -0.0043(9) 0.0023(8) -0.0023(8)
C6 0.0265(9) 0.0211(10) 0.0259(9) -0.0005(9) 0.0018(8) -0.0003(8)
C7 0.0285(10) 0.0223(9) 0.0279(10) -0.0028(10) 0.0023(8) 0.0010(8)
C8 0.0273(9) 0.0209(9) 0.0336(11) -0.0004(9) -0.0001(9) -0.0007(8)

#----------------------------------------------------------------------------#
# 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
F1 C1 1.337(3) . no
F2 C1 1.330(3) . no
F3 C1 1.330(3) . no
O1 C2 1.399(2) . no
O1 H1 0.8400 . no
O2 C3 1.206(2) . no
O3 C3 1.325(2) . no
O3 C4 1.466(2) . no
C1 C2 1.520(3) . no
C2 C3 1.523(3) . no
C2 H2 0.9800 . no
C4 C5 1.511(3) . no
C4 H4A 0.9700 . no
C4 H4B 0.9700 . no
C5 C6 1.520(3) . no
C5 H5A 0.9700 . no
C5 H5B 0.9700 . no
C6 C7 1.527(3) . no
C6 H6A 0.9700 . no
C6 H6B 0.9700 . no
C7 C8 1.522(3) . no
C7 H7A 0.9700 . no
C7 H7B 0.9700 . no
C8 C8 1.533(4) 2_575 no
C8 H8A 0.9700 . no
C8 H8B 0.9700 . no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 114.00 . . no
C3 O3 C4 116.82(14) . . no
F3 C1 F2 108.3(2) . . no
F3 C1 F1 106.97(17) . . no
F2 C1 F1 106.88(19) . . no
F3 C1 C2 112.08(19) . . no
F2 C1 C2 111.55(18) . . no
F1 C1 C2 110.84(18) . . no
O1 C2 C1 108.73(17) . . no
O1 C2 C3 108.37(15) . . no
C1 C2 C3 110.39(16) . . no
O1 C2 H2 109.8 . . no
C1 C2 H2 109.8 . . no
C3 C2 H2 109.8 . . no
O2 C3 O3 126.03(18) . . no
O2 C3 C2 122.90(17) . . no
O3 C3 C2 111.06(15) . . no
O3 C4 C5 111.50(15) . . no
O3 C4 H4A 109.3 . . no
C5 C4 H4A 109.3 . . no
O3 C4 H4B 109.3 . . no
C5 C4 H4B 109.3 . . no
H4A C4 H4B 108.0 . . no
C4 C5 C6 114.27(16) . . no
C4 C5 H5A 108.7 . . no
C6 C5 H5A 108.7 . . no
C4 C5 H5B 108.7 . . no
C6 C5 H5B 108.7 . . no
H5A C5 H5B 107.6 . . no
C5 C6 C7 112.33(16) . . no
C5 C6 H6A 109.1 . . no
C7 C6 H6A 109.1 . . no
C5 C6 H6B 109.1 . . no
C7 C6 H6B 109.1 . . no
H6A C6 H6B 107.9 . . no
C8 C7 C6 113.30(17) . . no
C8 C7 H7A 108.9 . . no
C6 C7 H7A 108.9 . . no
C8 C7 H7B 108.9 . . no
C6 C7 H7B 108.9 . . no
H7A C7 H7B 107.7 . . no
C7 C8 C8 112.8(2) . 2_575 no
C7 C8 H8A 109.0 . . no
C8 C8 H8A 109.0 2_575 . no
C7 C8 H8B 109.0 . . no
C8 C8 H8B 109.0 2_575 . no
H8A C8 H8B 107.8 . . no

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
F3 C1 C2 O1 172.82(17) . . . . no
F2 C1 C2 O1 -65.6(2) . . . . no
F1 C1 C2 O1 53.4(2) . . . . no
F3 C1 C2 C3 -68.4(2) . . . . no
F2 C1 C2 C3 53.2(2) . . . . no
F1 C1 C2 C3 172.14(16) . . . . no
C4 O3 C3 O2 1.2(3) . . . . no
C4 O3 C3 C2 -179.54(14) . . . . no
O1 C2 C3 O2 6.5(3) . . . . no
C1 C2 C3 O2 -112.5(2) . . . . no
O1 C2 C3 O3 -172.78(15) . . . . no
C1 C2 C3 O3 68.2(2) . . . . no
C3 O3 C4 C5 82.0(2) . . . . no
O3 C4 C5 C6 61.7(2) . . . . no
C4 C5 C6 C7 179.44(17) . . . . no
C5 C6 C7 C8 -179.86(19) . . . . no
C6 C7 C8 C8 -178.48(12) . . . 2_575 no

_diffrn_measured_fraction_theta_max 0.936
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.054
#==END



