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_section_title              
;
Isomorphic supramolecular structures via one-dimensional
hydrogen bonding motifs in crystals of chiral difluorolactates,
trichlorolactates and trifluorolactates
;

_publ_contact_author_name        'Dr Toshimasa Katagiri'

_publ_contact_author_address     
;
Applied Chemistry
Okayama University
Tsushimanaka 3-1-1
Okayama
700-8530
JAPAN
;

_publ_contact_author_email       tkata@cc.okayama-u.ac.jp

_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.

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

PLATON/PLUTON - Spek, A. L. (1990) Acta Cryst. A46, C34.

MERCURY - Bruno, I. J.; Cole, J. C.; Edgington, P. R.; Kessler, M. K.;
Macrae, C. F.; McCabe, P.; Pearson J.; Taylor, R. (2002) Acta Cryst. B58, 389.
;
loop_
_publ_author_name
'Satoshi Takahashi'
'Tatsuya Jukurogi'
'Toshimasa Katagiri'
'Kenji Uneyama'

data_(R)-4
_database_code_depnum_ccdc_archive 'CCDC 292296'
_audit_creation_method           SHELXL-97
_audit_update_record             
;
2005-12-8 CheckCIF
;
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_common            Isopropyl-(R)-(-)-3,3-difluorolactate
_chemical_melting_point          335
_chemical_formula_moiety         'C6 H10 F2 O3'
_chemical_formula_sum            'C6 H10 F2 O3'
_chemical_formula_weight         168.14
_chemical_absolute_configuration syn
_chemical_optical_rotation       '[\a]^25^~D~= -2.21 (c= 1.38, MeOH)'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a                   5.2602(4)
_cell_length_b                   9.2900(10)
_cell_length_c                   16.674(3)
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_volume                     814.81(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    6269
_cell_measurement_theta_min      8.1
_cell_measurement_theta_max      54.9

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_special_details           
;This compound tends to sublimate at room temperature.
A needle crystal was mounted on a glass capillary quickly
and quick-freezed by cold nitrogen flux of a low temperature device.
The crystal was cooled during the data collection.
;
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9800
_exptl_absorpt_correction_T_max  0.9866
_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      120(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 R-AXIS IV imaging plate'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            6180
_diffrn_reflns_av_R_equivalents  0.0105
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.06
_diffrn_reflns_theta_max         27.43
_reflns_number_total             1043
_reflns_number_gt                996
_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. 1.4 (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 have been located from Fourier difference map
and fixed to its position.
The remaining H-atoms were included in caluculated position.
and treated as riding atoms using the SHELXL default parameters.

Large displacement parameters for two methyl C atoms of the isopropyl group
were indicative of positional disorder. The disorderd isopropyl group were
refined using PART instruction of SHELXL (C5&C6: part1, C7&C8: part2)
with occupancy factors of 0.6(for part1):0.4(for part2).

Refinement of this disorderd model gave significantly improved R values.

[R1 = 0.066, wR2 = 0.18 (before) >> R1 = 0.0346, wR2 = 0.0888 (after)]

Even with this disorder model, some displacement parameters remain high and
the geometry in the isopropyl group is somewhat unreliable.
;
_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^)+(0.0684P)^2^+0.0514P] 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 (R)-2,2-difluorolactic 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         1043
_refine_ls_number_parameters     126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.939
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.939
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
# 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 0.6312(3) 1.11755(13) 0.52751(8) 0.0568(4) Uani 1 1 d . . .
F2 F 0.2498(3) 1.04067(17) 0.55404(7) 0.0634(4) Uani 1 1 d . . .
O1 O 0.5687(2) 0.81975(12) 0.50575(6) 0.0281(3) Uani 1 1 d . . .
O2 O 0.8730(2) 0.88811(13) 0.38376(7) 0.0311(3) Uani 1 1 d . . .
O3 O 0.5840(2) 1.04245(13) 0.33351(7) 0.0312(3) Uani 1 1 d . A .
C1 C 0.4156(4) 1.0640(2) 0.49330(11) 0.0392(4) Uani 1 1 d . . .
H2 H 0.3436 1.1347 0.4542 0.047 Uiso 1 1 calc R . .
C2 C 0.4738(3) 0.92256(16) 0.45183(8) 0.0236(3) Uani 1 1 d . . .
H3 H 0.3145 0.8847 0.4268 0.028 Uiso 1 1 calc R . .
C3 C 0.6705(3) 0.94781(15) 0.38652(8) 0.0215(3) Uani 1 1 d . . .
C4 C 0.7512(4) 1.0815(2) 0.26597(11) 0.0387(4) Uani 1 1 d . . .
C5 C 0.9342(9) 1.1886(5) 0.2901(2) 0.0538(10) Uani 0.60 1 d P A 1
H5A H 1.0335 1.2191 0.2434 0.081 Uiso 0.60 1 calc PR A 1
H5B H 1.0483 1.1477 0.3306 0.081 Uiso 0.60 1 calc PR A 1
H5C H 0.8452 1.2718 0.3128 0.081 Uiso 0.60 1 calc PR A 1
C6 C 0.5693(10) 1.1273(5) 0.1985(2) 0.0556(10) Uani 0.60 1 d P A 1
H6A H 0.6656 1.1410 0.1488 0.083 Uiso 0.60 1 calc PR A 1
H6B H 0.4857 1.2178 0.2133 0.083 Uiso 0.60 1 calc PR A 1
H6C H 0.4406 1.0524 0.1905 0.083 Uiso 0.60 1 calc PR A 1
C7 C 0.650(2) 1.0414(10) 0.1941(4) 0.080(3) Uani 0.40 1 d P A 2
H7A H 0.7627 1.0731 0.1506 0.120 Uiso 0.40 1 calc PR A 2
H7B H 0.4827 1.0858 0.1875 0.120 Uiso 0.40 1 calc PR A 2
H7C H 0.6333 0.9364 0.1924 0.120 Uiso 0.40 1 calc PR A 2
C8 C 0.769(2) 1.2533(9) 0.2741(4) 0.094(4) Uani 0.40 1 d P A 2
H8A H 0.8605 1.2926 0.2279 0.142 Uiso 0.40 1 calc PR A 2
H8B H 0.8603 1.2780 0.3235 0.142 Uiso 0.40 1 calc PR A 2
H8C H 0.5974 1.2940 0.2760 0.142 Uiso 0.40 1 calc PR A 2
H4 H 0.859(7) 0.989(4) 0.254(2) 0.082(10) Uiso 1 1 d . B 1
H1 H 0.4522 0.7603 0.5246 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 0.0769(10) 0.0387(6) 0.0549(7) -0.0146(5) 0.0070(7) -0.0162(7)
F2 0.0716(10) 0.0696(9) 0.0490(7) -0.0038(6) 0.0361(7) 0.0078(8)
O1 0.0245(5) 0.0287(5) 0.0311(5) 0.0138(4) -0.0003(4) -0.0034(4)
O2 0.0262(6) 0.0374(6) 0.0297(5) 0.0100(4) 0.0034(4) 0.0080(5)
O3 0.0299(6) 0.0352(6) 0.0287(5) 0.0138(4) 0.0041(4) 0.0077(5)
C1 0.0473(10) 0.0362(8) 0.0342(8) 0.0015(7) 0.0144(8) 0.0071(7)
C2 0.0210(7) 0.0254(7) 0.0244(6) 0.0057(5) -0.0007(5) 0.0006(5)
C3 0.0226(7) 0.0203(6) 0.0216(6) 0.0023(5) -0.0016(5) -0.0005(5)
C4 0.0431(10) 0.0432(10) 0.0299(8) 0.0170(7) 0.0103(7) 0.0091(8)
C5 0.055(2) 0.060(2) 0.0472(19) 0.0206(18) 0.0061(17) -0.0163(19)
C6 0.072(3) 0.067(3) 0.0271(15) 0.0200(17) -0.0063(17) 0.002(2)
C7 0.117(8) 0.079(5) 0.044(3) -0.020(3) 0.035(4) -0.034(5)
C8 0.168(10) 0.069(5) 0.047(4) -0.010(3) 0.038(5) -0.067(6)

#----------------------------------------------------------------------------#
# 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 1.363(3) . ?
F2 C1 1.354(2) . ?
O1 C2 1.4036(17) . ?
O1 H1 0.880 . ?
O2 C3 1.2021(18) . ?
O3 C3 1.3271(17) . ?
O3 C4 1.474(2) . ?
C1 C2 1.516(2) . ?
C1 H2 1.0000 . ?
C2 C3 1.5202(19) . ?
C2 H3 1.0000 . ?
C4 C5 1.441(5) . ?
C4 C6 1.536(4) . ?
C4 C7 1.363(8) . ?
C4 C8 1.604(8) . ?
C4 H4 1.05(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
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 . . ?
C3 O3 C4 117.86(13) . . ?
F2 C1 F1 106.34(15) . . ?
F2 C1 C2 109.40(15) . . ?
F1 C1 C2 109.82(15) . . ?
F2 C1 H2 110.4 . . ?
F1 C1 H2 110.4 . . ?
C2 C1 H2 110.4 . . ?
O1 C2 C1 111.68(13) . . ?
O1 C2 C3 108.76(12) . . ?
C1 C2 C3 109.29(12) . . ?
O1 C2 H3 109.0 . . ?
C1 C2 H3 109.0 . . ?
C3 C2 H3 109.0 . . ?
O2 C3 O3 125.73(13) . . ?
O2 C3 C2 124.02(12) . . ?
O3 C3 C2 110.24(12) . . ?
C7 C4 C5 134.0(4) . . ?
C7 C4 O3 111.9(4) . . ?
C5 C4 O3 110.8(2) . . ?
C5 C4 C6 115.4(3) . . ?
O3 C4 C6 104.8(2) . . ?
C7 C4 C8 111.7(5) . . ?
O3 C4 C8 102.4(3) . . ?
C6 C4 C8 79.8(5) . . ?
C7 C4 H4 79.5(18) . . ?
C5 C4 H4 105.0(19) . . ?
O3 C4 H4 105.5(18) . . ?
C6 C4 H4 115.0(18) . . ?
C8 C4 H4 143.1(19) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H7A C7 H4 98.2 . . ?
H7B C7 H4 146.7 . . ?
H7C C7 H4 76.8 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F2 C1 C2 O1 -56.7(2) . . . . ?
F1 C1 C2 O1 59.70(18) . . . . ?
F2 C1 C2 C3 -177.05(14) . . . . ?
F1 C1 C2 C3 -60.69(17) . . . . ?
C4 O3 C3 O2 -1.5(2) . . . . ?
C4 O3 C3 C2 179.38(14) . . . . ?
O1 C2 C3 O2 -0.4(2) . . . . ?
C1 C2 C3 O2 121.73(17) . . . . ?
O1 C2 C3 O3 178.68(12) . . . . ?
C1 C2 C3 O3 -59.16(16) . . . . ?
C3 O3 C4 C7 116.3(5) . . . . ?
C3 O3 C4 C5 -81.4(3) . . . . ?
C3 O3 C4 C6 153.5(2) . . . . ?
C3 O3 C4 C8 -123.9(5) . . . . ?
#END
#------------------------------------------------------------------------------
data_(R,R)-5a
_database_code_depnum_ccdc_archive 'CCDC 292297'
_audit_creation_method           SHELXL-97
_audit_update_record             
;
2005-12-8 CheckCIF
;
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_common            Hexamethylene-(R,R)-bis(3,3-difluorolactate)
_chemical_melting_point          356
_chemical_formula_moiety         'C12 H18 F4 O6'
_chemical_formula_sum            'C12 H18 F4 O6'
_chemical_formula_weight         334.26
_chemical_absolute_configuration syn
_chemical_optical_rotation       '[\a]^25^~D~= -5.72 (c= 0.81, 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                   18.8223(6)
_cell_length_b                   5.14670(10)
_cell_length_c                   7.7739(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     753.08(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    7965
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      54.9

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_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    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_T_max  0.992
_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      120(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 R-AXIS IV imaging plate'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            5840
_diffrn_reflns_av_R_equivalents  0.055
_diffrn_reflns_av_sigmaI/netI    0.0842
_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       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.40
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1043
_reflns_number_gt                945
_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. 1.4 (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^)+(0.0417P)^2^+0.0446P] 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 (R)-difluorolactic 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         1043
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_restrained_S_all      1.216
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.060

#----------------------------------------------------------------------------#
# 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 0.57004(9) 0.8242(4) 0.5692(3) 0.0399(5) Uani 1 1 d . . .
F2 F 0.58875(9) 1.2054(4) 0.4575(2) 0.0429(5) Uani 1 1 d . . .
O1 O 0.71446(10) 0.9496(3) 0.5068(2) 0.0241(4) Uani 1 1 d . . .
O2 O 0.72274(9) 0.6709(3) 0.7972(2) 0.0239(4) Uani 1 1 d . . .
O3 O 0.64581(9) 0.9389(3) 0.9325(2) 0.0171(4) Uani 1 1 d . . .
C1 C 0.59675(14) 1.0635(6) 0.6034(4) 0.0257(6) Uani 1 1 d . . .
C2 C 0.67523(12) 1.0437(5) 0.6482(3) 0.0172(5) Uani 1 1 d . . .
H3 H 0.6930 1.2160 0.6801 0.021 Uiso 1 1 calc R . .
C3 C 0.68480(12) 0.8601(5) 0.7985(3) 0.0161(5) Uani 1 1 d . . .
C4 C 0.65133(14) 0.7868(5) 1.0920(3) 0.0209(5) Uani 1 1 d . . .
H4A H 0.6392 0.8964 1.1891 0.025 Uiso 1 1 calc R . .
H4B H 0.7000 0.7289 1.1068 0.025 Uiso 1 1 calc R . .
C5 C 0.60271(13) 0.5538(5) 1.0892(4) 0.0217(5) Uani 1 1 d . . .
H5A H 0.6120 0.4493 1.1905 0.026 Uiso 1 1 calc R . .
H5B H 0.6141 0.4490 0.9892 0.026 Uiso 1 1 calc R . .
C6 C 0.52361(13) 0.6202(4) 1.0845(4) 0.0200(5) Uani 1 1 d . . .
H6A H 0.5120 0.7264 1.1837 0.024 Uiso 1 1 calc R . .
H6B H 0.5138 0.7218 0.9821 0.024 Uiso 1 1 calc R . .
H2 H 0.5662(15) 1.149(6) 0.696(4) 0.020 Uiso 1 1 d . . .
H1 H 0.7321 1.0704 0.4496 0.039 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 0.0263(8) 0.0501(10) 0.0435(10) -0.0042(11) -0.0069(8) -0.0118(9)
F2 0.0395(10) 0.0654(13) 0.0238(9) 0.0194(10) 0.0021(8) 0.0157(11)
O1 0.0266(9) 0.0213(8) 0.0244(9) 0.0029(8) 0.0131(8) 0.0005(9)
O2 0.0226(8) 0.0218(8) 0.0272(10) 0.0014(8) 0.0015(9) 0.0088(9)
O3 0.0205(8) 0.0159(7) 0.0150(8) 0.0001(8) 0.0022(7) 0.0003(7)
C1 0.0247(13) 0.0324(14) 0.0199(13) 0.0065(12) -0.0010(12) 0.0048(14)
C2 0.0172(11) 0.0159(11) 0.0185(12) 0.0002(10) 0.0058(10) 0.0015(11)
C3 0.0112(9) 0.0187(10) 0.0185(11) -0.0020(11) -0.0009(10) -0.0017(10)
C4 0.0261(12) 0.0230(11) 0.0136(11) 0.0001(11) -0.0026(11) -0.0011(11)
C5 0.0300(12) 0.0174(10) 0.0178(12) 0.0067(11) 0.0010(12) -0.0010(12)
C6 0.0252(11) 0.0145(10) 0.0203(11) -0.0014(10) 0.0012(10) -0.0029(11)

#----------------------------------------------------------------------------#
# 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 1.357(3) . ?
F2 C1 1.357(3) . ?
O1 C2 1.410(3) . ?
O1 H1 0.830 . ?
O2 C3 1.207(3) . ?
O3 C3 1.337(3) . ?
O3 C4 1.470(3) . ?
C1 C2 1.521(3) . ?
C1 H2 1.02(3) . ?
C2 C3 1.513(4) . ?
C2 H3 0.9800 . ?
C4 C5 1.508(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.528(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C6 1.523(4) 2_665 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 112.0 . . ?
C3 O3 C4 117.17(18) . . ?
F1 C1 F2 106.5(2) . . ?
F1 C1 C2 110.1(2) . . ?
F2 C1 C2 109.6(2) . . ?
F1 C1 H2 108.7(16) . . ?
F2 C1 H2 107.0(16) . . ?
C2 C1 H2 114.6(16) . . ?
O1 C2 C3 108.98(19) . . ?
O1 C2 C1 110.7(2) . . ?
C3 C2 C1 109.5(2) . . ?
O1 C2 H3 109.2 . . ?
C3 C2 H3 109.2 . . ?
C1 C2 H3 109.2 . . ?
O2 C3 O3 125.1(2) . . ?
O2 C3 C2 124.6(2) . . ?
O3 C3 C2 110.29(19) . . ?
O3 C4 C5 111.6(2) . . ?
O3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
O3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 114.4(2) . . ?
C4 C5 H5A 108.6 . . ?
C6 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
C6 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C6 C6 C5 112.8(2) 2_665 . ?
C6 C6 H6A 109.0 2_665 . ?
C5 C6 H6A 109.0 . . ?
C6 C6 H6B 109.0 2_665 . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?

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 63.5(3) . . . . ?
F2 C1 C2 O1 -53.3(3) . . . . ?
F1 C1 C2 C3 -56.7(3) . . . . ?
F2 C1 C2 C3 -173.5(2) . . . . ?
C4 O3 C3 O2 1.8(3) . . . . ?
C4 O3 C3 C2 -177.64(18) . . . . ?
O1 C2 C3 O2 3.0(3) . . . . ?
C1 C2 C3 O2 124.3(2) . . . . ?
O1 C2 C3 O3 -177.47(18) . . . . ?
C1 C2 C3 O3 -56.3(3) . . . . ?
C3 O3 C4 C5 -83.9(2) . . . . ?
O3 C4 C5 C6 -64.8(3) . . . . ?
C4 C5 C6 C6 -179.16(16) . . . 2_665 ?
#END
#------------------------------------------------------------------------------
data_(S)-6
_database_code_depnum_ccdc_archive 'CCDC 292298'
_audit_creation_method           SHELXL-97
_audit_update_record             
;
2005-12-8 CheckCIF
;
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_common            Isopropyl-(S)-(-)-3,3,3-trichlorolactate
_chemical_melting_point          316
_chemical_formula_moiety         'C6 H9 Cl3 O3'
_chemical_formula_sum            'C6 H9 Cl3 O3'
_chemical_formula_weight         235.48
_chemical_absolute_configuration ad
_chemical_optical_rotation       '[\a]^20^~D~= -23.0 (c=0.506, MeOH)'

#----------------------------------------------------------------------------#
# 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                   8.6464(3)
_cell_length_b                   5.64350(10)
_cell_length_c                   10.8654(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.4510(10)
_cell_angle_gamma                90.00
_cell_volume                     499.93(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5435
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.5

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_special_details           
;This compound sublimates slowly at room temperature.
A platelet crystal was mounted on a glass capillary
and quick-freezed by cold nitrogen flux of a low temperature device.
The crystal was cooled during the data collection.
;
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.883
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8072
_exptl_absorpt_correction_T_max  0.9005
_exptl_absorpt_process_details   
; NUMABS Higashi T. (1999)
Program for absorption correction, Rigaku Corporation, Tokyo, Japan.
;
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      123(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 R-AXIS 4 imaging plate'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            3871
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2150
_reflns_number_gt                2128
_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. 1.4 (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^)+(0.0383P)^2^+0.1367P] 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 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_number_reflns         2150
_refine_ls_number_parameters     111
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0659
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.171
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.068

#----------------------------------------------------------------------------#
# 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
Cl1 Cl 0.72216(5) 0.66903(8) 0.75527(4) 0.01732(11) Uani 1 1 d . . .
Cl2 Cl 0.64727(6) 0.22371(8) 0.85211(4) 0.01846(12) Uani 1 1 d . . .
Cl3 Cl 0.47165(6) 0.64717(8) 0.87446(4) 0.01837(12) Uani 1 1 d . . .
O1 O 0.51439(19) 0.3572(3) 0.55260(14) 0.0185(3) Uani 1 1 d . . .
O2 O 0.31020(19) 0.0532(3) 0.59188(15) 0.0210(3) Uani 1 1 d . . .
O3 O 0.21959(17) 0.3081(3) 0.71064(15) 0.0182(3) Uani 1 1 d . . .
C1 C 0.5619(2) 0.4914(4) 0.77407(18) 0.0120(3) Uani 1 1 d . . .
C2 C 0.4347(2) 0.4393(4) 0.63657(19) 0.0130(3) Uani 1 1 d . . .
H2 H 0.3726 0.5872 0.6001 0.016 Uiso 1 1 calc R . .
C3 C 0.3144(2) 0.2435(4) 0.64327(18) 0.0142(4) Uani 1 1 d . . .
C4 C 0.1070(2) 0.1286(4) 0.7310(2) 0.0209(4) Uani 1 1 d . . .
H4 H 0.1575 -0.0321 0.7363 0.025 Uiso 1 1 calc R . .
C5 C 0.0877(3) 0.1898(7) 0.8606(2) 0.0352(6) Uani 1 1 d . . .
H5A H 0.1957 0.1913 0.9288 0.053 Uiso 1 1 calc R . .
H5B H 0.0179 0.0712 0.8821 0.053 Uiso 1 1 calc R . .
H5C H 0.0370 0.3466 0.8549 0.053 Uiso 1 1 calc R . .
C6 C -0.0520(2) 0.1367(5) 0.6172(2) 0.0262(5) Uani 1 1 d . . .
H6A H -0.0992 0.2961 0.6101 0.039 Uiso 1 1 calc R . .
H6B H -0.1292 0.0215 0.6313 0.039 Uiso 1 1 calc R . .
H6C H -0.0305 0.0979 0.5365 0.039 Uiso 1 1 calc R . .
H1 H 0.5427 0.4680 0.5007 0.028 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
Cl1 0.0183(2) 0.0147(2) 0.0198(2) -0.00072(16) 0.00745(16) -0.00578(16)
Cl2 0.0205(2) 0.0130(2) 0.0205(2) 0.00543(17) 0.00507(17) 0.00255(17)
Cl3 0.0214(2) 0.0190(3) 0.0171(2) -0.00698(17) 0.00955(17) -0.00072(17)
O1 0.0257(7) 0.0200(8) 0.0148(7) -0.0044(5) 0.0135(6) -0.0060(6)
O2 0.0215(7) 0.0191(8) 0.0262(8) -0.0080(6) 0.0129(6) -0.0070(6)
O3 0.0149(6) 0.0222(8) 0.0197(7) -0.0030(6) 0.0085(6) -0.0018(6)
C1 0.0145(8) 0.0115(9) 0.0115(8) -0.0011(7) 0.0062(7) -0.0009(7)
C2 0.0135(8) 0.0144(9) 0.0110(8) 0.0001(6) 0.0039(7) -0.0016(7)
C3 0.0130(8) 0.0160(10) 0.0125(8) 0.0001(7) 0.0029(6) -0.0006(7)
C4 0.0131(8) 0.0276(13) 0.0230(10) 0.0056(9) 0.0073(7) -0.0001(8)
C5 0.0176(9) 0.069(2) 0.0196(10) 0.0089(13) 0.0070(8) -0.0009(12)
C6 0.0160(9) 0.0369(15) 0.0233(10) 0.0011(9) 0.0034(8) -0.0074(9)

#----------------------------------------------------------------------------#
# 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
Cl1 C1 1.7762(19) . ?
Cl2 C1 1.769(2) . ?
Cl3 C1 1.7716(19) . ?
O1 C2 1.393(2) . ?
O1 H1 0.9300 . ?
O2 C3 1.205(3) . ?
O3 C3 1.319(2) . ?
O3 C4 1.472(2) . ?
C1 C2 1.560(3) . ?
C2 C3 1.536(3) . ?
C2 H2 1.0000 . ?
C4 C5 1.512(3) . ?
C4 C6 1.513(3) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
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 118.0 . . ?
C3 O3 C4 117.20(17) . . ?
C2 C1 Cl2 110.29(14) . . ?
C2 C1 Cl3 111.61(13) . . ?
Cl2 C1 Cl3 109.12(10) . . ?
C2 C1 Cl1 108.94(13) . . ?
Cl2 C1 Cl1 108.67(10) . . ?
Cl3 C1 Cl1 108.14(10) . . ?
O1 C2 C3 106.39(17) . . ?
O1 C2 C1 110.18(15) . . ?
C3 C2 C1 111.28(15) . . ?
O1 C2 H2 109.6 . . ?
C3 C2 H2 109.6 . . ?
C1 C2 H2 109.6 . . ?
O2 C3 O3 125.12(19) . . ?
O2 C3 C2 122.36(17) . . ?
O3 C3 C2 112.52(18) . . ?
O3 C4 C5 105.45(19) . . ?
O3 C4 C6 108.83(17) . . ?
C5 C4 C6 113.70(18) . . ?
O3 C4 H4 109.6 . . ?
C5 C4 H4 109.6 . . ?
C6 C4 H4 109.6 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl2 C1 C2 O1 -69.50(19) . . . . ?
Cl3 C1 C2 O1 169.02(15) . . . . ?
Cl1 C1 C2 O1 49.7(2) . . . . ?
Cl2 C1 C2 C3 48.25(19) . . . . ?
Cl3 C1 C2 C3 -73.22(19) . . . . ?
Cl1 C1 C2 C3 167.44(14) . . . . ?
C4 O3 C3 O2 3.8(3) . . . . ?
C4 O3 C3 C2 -175.98(15) . . . . ?
O1 C2 C3 O2 6.0(3) . . . . ?
C1 C2 C3 O2 -114.0(2) . . . . ?
O1 C2 C3 O3 -174.14(16) . . . . ?
C1 C2 C3 O3 65.8(2) . . . . ?
C3 O3 C4 C5 149.66(18) . . . . ?
C3 O3 C4 C6 -88.0(2) . . . . ?
#END
#------------------------------------------------------------------------------

data_(S,S)-7b
_database_code_depnum_ccdc_archive 'CCDC 292299'
_audit_creation_method           SHELXL-97
_audit_update_record             
;
2005-12-8 CheckCIF
;
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_common            
(-)-Octamethylene-(S,S)-bis(3,3,3-trichlorolactate)
_chemical_melting_point          357
_chemical_formula_moiety         'C14 H20 Cl6 O6'
_chemical_formula_sum            'C14 H20 Cl6 O6'
_chemical_formula_weight         497.03
_chemical_absolute_configuration syn
_chemical_optical_rotation       '[\a]^20^~D~= -12.7 (c = 0.63, MeOH)'

#----------------------------------------------------------------------------#
# 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                   21.7785(17)
_cell_length_b                   5.7582(2)
_cell_length_c                   8.4827(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1063.77(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12994
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      27.5
_cell_measurement_temperature    150(1)

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_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    0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.92
_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_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Rigaku RAXIS-IV Imaging Plate'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            8008
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.0632
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1352
_reflns_number_gt                1222
_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. 1.4 (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^)+(0.0441P)^2^+0.0780P] 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 
;Flack H D (1983), Acta Cryst. A39, 876-881
The Flack parameter was too large to determine the absolute configuration.
So Friedel pairs were merged before final refinement cycle.
;
_refine_ls_abs_structure_Flack   0.41(14)
_refine_ls_number_reflns         1352
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_restrained_S_all      1.176
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.931
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.931
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.064

#----------------------------------------------------------------------------#
# 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
Cl1 Cl 0.88407(5) 1.15482(18) -0.10871(12) 0.0409(3) Uani 1 1 d . . .
Cl2 Cl 0.90450(5) 0.71611(19) 0.04642(15) 0.0498(3) Uani 1 1 d . . .
Cl3 Cl 0.92418(4) 1.14679(19) 0.21224(12) 0.0384(3) Uani 1 1 d . . .
O1 O 0.77243(11) 0.9195(5) 0.0033(3) 0.0355(7) Uani 1 1 d . . .
O2 O 0.77271(11) 0.6572(5) 0.2542(3) 0.0368(6) Uani 1 1 d . . .
O3 O 0.82046(10) 0.9292(5) 0.3983(3) 0.0273(6) Uani 1 1 d . . .
C1 C 0.87746(17) 1.0020(6) 0.0725(4) 0.0293(8) Uani 1 1 d . . .
C2 C 0.80931(15) 1.0021(7) 0.1252(4) 0.0260(7) Uani 1 1 d . . .
H2 H 0.7969 1.1606 0.1526 0.031 Uiso 1 1 calc R . .
C3 C 0.79896(14) 0.8430(6) 0.2659(4) 0.0257(7) Uani 1 1 d . . .
C4 C 0.81123(17) 0.7928(8) 0.5426(4) 0.0316(8) Uani 1 1 d . . .
H3A H 0.7696 0.7330 0.5439 0.038 Uiso 1 1 calc R . .
H3B H 0.8162 0.8934 0.6334 0.038 Uiso 1 1 calc R . .
C5 C 0.85552(16) 0.5934(8) 0.5554(5) 0.0349(9) Uani 1 1 d . . .
H4A H 0.8493 0.4900 0.4666 0.042 Uiso 1 1 calc R . .
H4B H 0.8465 0.5068 0.6507 0.042 Uiso 1 1 calc R . .
C6 C 0.92258(17) 0.6687(7) 0.5590(5) 0.0353(9) Uani 1 1 d . . .
H5A H 0.9313 0.7587 0.4650 0.042 Uiso 1 1 calc R . .
H5B H 0.9290 0.7690 0.6494 0.042 Uiso 1 1 calc R . .
C7 C 0.96725(18) 0.4687(8) 0.5679(6) 0.0415(10) Uani 1 1 d . . .
H6A H 0.9587 0.3812 0.6631 0.050 Uiso 1 1 calc R . .
H6B H 0.9596 0.3666 0.4790 0.050 Uiso 1 1 calc R . .
H1 H 0.7547 1.0365 -0.0458 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
Cl1 0.0590(6) 0.0349(5) 0.0287(4) 0.0046(4) 0.0026(4) -0.0098(5)
Cl2 0.0540(6) 0.0247(5) 0.0706(8) 0.0012(5) 0.0185(6) 0.0110(4)
Cl3 0.0308(4) 0.0442(6) 0.0403(5) 0.0048(5) -0.0078(4) -0.0093(4)
O1 0.0440(15) 0.0304(16) 0.0319(14) 0.0073(12) -0.0204(13) -0.0050(12)
O2 0.0434(14) 0.0372(16) 0.0297(14) 0.0022(13) -0.0063(12) -0.0149(13)
O3 0.0267(12) 0.0319(15) 0.0235(12) -0.0031(11) -0.0026(10) 0.0043(10)
C1 0.0337(18) 0.0219(18) 0.0322(19) -0.0011(15) 0.0025(16) -0.0012(15)
C2 0.0256(16) 0.0266(18) 0.0258(16) 0.0007(16) -0.0088(14) -0.0010(14)
C3 0.0240(16) 0.0274(18) 0.0258(17) -0.0034(16) -0.0042(14) 0.0032(15)
C4 0.0287(17) 0.041(2) 0.0249(17) -0.0001(17) 0.0030(15) 0.0027(16)
C5 0.0364(19) 0.039(2) 0.0292(17) 0.0067(18) -0.0027(17) 0.0028(17)
C6 0.0338(17) 0.038(2) 0.0345(19) -0.0008(19) 0.0001(17) 0.0026(17)
C7 0.0350(18) 0.042(2) 0.048(2) 0.005(2) -0.0071(19) -0.0001(18)

#----------------------------------------------------------------------------#
# 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
Cl1 C1 1.777(4) . ?
Cl2 C1 1.762(4) . ?
Cl3 C1 1.771(4) . ?
O1 C2 1.393(4) . ?
O1 H1 0.880 . ?
O2 C3 1.217(4) . ?
O3 C3 1.314(4) . ?
O3 C4 1.468(5) . ?
C1 C2 1.550(5) . ?
C2 C3 1.521(5) . ?
C2 H2 0.9800 . ?
C4 C5 1.504(5) . ?
C4 H3A 0.9700 . ?
C4 H3B 0.9700 . ?
C5 C6 1.524(6) . ?
C5 H4A 0.9700 . ?
C5 H4B 0.9700 . ?
C6 C7 1.509(5) . ?
C6 H5A 0.9700 . ?
C6 H5B 0.9700 . ?
C7 C7 1.471(8) 2_765 ?
C7 H6A 0.9700 . ?
C7 H6B 0.9700 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 110.0 . . ?
C3 O3 C4 117.5(3) . . ?
C2 C1 Cl2 110.9(3) . . ?
C2 C1 Cl3 110.9(2) . . ?
Cl2 C1 Cl3 109.4(2) . . ?
C2 C1 Cl1 109.1(2) . . ?
Cl2 C1 Cl1 109.1(2) . . ?
Cl3 C1 Cl1 107.4(2) . . ?
O1 C2 C3 107.0(3) . . ?
O1 C2 C1 109.7(3) . . ?
C3 C2 C1 111.6(3) . . ?
O1 C2 H2 109.5 . . ?
C3 C2 H2 109.5 . . ?
C1 C2 H2 109.5 . . ?
O2 C3 O3 124.7(3) . . ?
O2 C3 C2 122.3(3) . . ?
O3 C3 C2 113.0(3) . . ?
O3 C4 C5 112.4(3) . . ?
O3 C4 H3A 109.1 . . ?
C5 C4 H3A 109.1 . . ?
O3 C4 H3B 109.1 . . ?
C5 C4 H3B 109.1 . . ?
H3A C4 H3B 107.9 . . ?
C4 C5 C6 113.5(4) . . ?
C4 C5 H4A 108.9 . . ?
C6 C5 H4A 108.9 . . ?
C4 C5 H4B 108.9 . . ?
C6 C5 H4B 108.9 . . ?
H4A C5 H4B 107.7 . . ?
C7 C6 C5 113.7(4) . . ?
C7 C6 H5A 108.8 . . ?
C5 C6 H5A 108.8 . . ?
C7 C6 H5B 108.8 . . ?
C5 C6 H5B 108.8 . . ?
H5A C6 H5B 107.7 . . ?
C7 C7 C6 116.0(5) 2_765 . ?
C7 C7 H6A 108.3 2_765 . ?
C6 C7 H6A 108.3 . . ?
C7 C7 H6B 108.3 2_765 . ?
C6 C7 H6B 108.3 . . ?
H6A C7 H6B 107.4 . . ?
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
Cl2 C1 C2 O1 -67.3(3) . . . . ?
Cl3 C1 C2 O1 171.0(3) . . . . ?
Cl1 C1 C2 O1 52.9(3) . . . . ?
Cl2 C1 C2 C3 51.1(3) . . . . ?
Cl3 C1 C2 C3 -70.7(3) . . . . ?
Cl1 C1 C2 C3 171.2(2) . . . . ?
C4 O3 C3 O2 -1.0(5) . . . . ?
C4 O3 C3 C2 178.2(3) . . . . ?
O1 C2 C3 O2 13.1(4) . . . . ?
C1 C2 C3 O2 -107.0(4) . . . . ?
O1 C2 C3 O3 -166.1(3) . . . . ?
C1 C2 C3 O3 73.9(4) . . . . ?
C3 O3 C4 C5 77.7(4) . . . . ?
O3 C4 C5 C6 60.4(4) . . . . ?
C4 C5 C6 C7 -178.6(4) . . . . ?
C5 C6 C7 C7 178.6(2) . . . 2_765 ?
#END
#------------------------------------------------------------------------------
data_(S,S)-21
_database_code_depnum_ccdc_archive 'CCDC 292300'
_audit_creation_method           SHELXL-97
_audit_update_record             
;
2005-12-8 CheckCIF
;
#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_common            
(+)-(S)-1-Phenylethylammonium-(S)-3,3,3-trichlorolactate
_chemical_melting_point          399
_chemical_formula_sum            'C11 H14 Cl3 N O3 '
_chemical_formula_moiety         'C8 H12 N1, C3 H2 Cl3 O3 '
_chemical_formula_weight         314.58
_chemical_absolute_configuration rmad
_chemical_optical_rotation       '[\a]^20^~D~= +18.62 (c = 1.3, MeOH)'

#----------------------------------------------------------------------------#
# 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                   9.2129(1)
_cell_length_b                   6.6622(2)
_cell_length_c                   12.5141(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.890(2)
_cell_angle_gamma                90.00
_cell_volume                     745.63(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    2455
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      27.4

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_special_details           
;Single crystal was grown in ethanol solution.
A block crystal was mounted on a glass capillary.
The data were collected at room temperature.
;
#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_process_details   
;NUMABS Higashi T. (1999)
Program for absorption correction, Rigaku Corporation, Tokyo, Japan.
;
#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_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            4397
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_sigmaI/netI    0.2074
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1778
_reflns_number_gt                1510
_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. 1.4 (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 NH3(+) and OH have been located from Fourier difference map
and fixed to their 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^)+(0.0720P)^2^+0.4132P] 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 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(16)
_refine_ls_number_reflns         1778
_refine_ls_number_parameters     175
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1562
_refine_ls_wR_factor_gt          0.1499
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
# 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5203(5) 0.5189(8) 0.7932(4) 0.0498(11) Uani 1 1 d . . .
C2 C 0.6388(5) 0.6431(8) 0.7569(4) 0.0472(10) Uani 1 1 d . . .
H2 H 0.6857 0.5583 0.7106 0.057 Uiso 1 1 calc R . .
C3 C 0.7631(5) 0.7224(8) 0.8538(4) 0.0468(11) Uani 1 1 d . . .
C4 C 1.1398(9) 0.0492(13) 0.8004(7) 0.090(2) Uani 1 1 d . . .
H4A H 1.2031 0.0169 0.8712 0.080 Uiso 1 1 calc R . .
H4B H 1.1995 0.0614 0.7476 0.080 Uiso 1 1 calc R . .
H4C H 1.0673 -0.0555 0.7780 0.080 Uiso 1 1 calc R . .
C5 C 1.0606(6) 0.2452(9) 0.8077(5) 0.0558(13) Uani 1 1 d . . .
H5 H 1.1367 0.3490 0.8324 0.067 Uiso 1 1 calc R . .
C6 C 0.9579(6) 0.3146(10) 0.7000(4) 0.0547(12) Uani 1 1 d . . .
C7 C 0.8369(8) 0.2011(13) 0.6467(5) 0.0730(17) Uani 1 1 d . . .
H6 H 0.8186 0.0772 0.6751 0.080 Uiso 1 1 calc R . .
C8 C 0.7434(9) 0.2715(19) 0.5516(6) 0.096(3) Uani 1 1 d . . .
H7 H 0.6616 0.1939 0.5172 0.080 Uiso 1 1 calc R . .
C9 C 0.7653(10) 0.446(2) 0.5070(5) 0.106(4) Uani 1 1 d . . .
H8 H 0.6993 0.4906 0.4430 0.080 Uiso 1 1 calc R . .
C10 C 0.8852(11) 0.5580(15) 0.5561(7) 0.100(3) Uani 1 1 d . . .
H9 H 0.9038 0.6778 0.5236 0.080 Uiso 1 1 calc R . .
C11 C 0.9818(7) 0.4969(11) 0.6550(5) 0.0661(15) Uani 1 1 d . . .
H10 H 1.0611 0.5783 0.6899 0.080 Uiso 1 1 calc R . .
Cl1 Cl 0.59341(17) 0.29139(19) 0.85391(14) 0.0707(5) Uani 1 1 d . . .
Cl2 Cl 0.4426(3) 0.6501(4) 0.8877(2) 0.1171(9) Uani 1 1 d . . .
Cl3 Cl 0.3778(2) 0.4533(4) 0.67781(18) 0.1049(9) Uani 1 1 d . . .
N1 N 0.9731(5) 0.2248(7) 0.8919(4) 0.0451(9) Uani 1 1 d . . .
O1 O 0.5698(5) 0.8051(8) 0.6932(4) 0.0835(15) Uani 1 1 d . . .
O2 O 0.7670(5) 0.9035(6) 0.8689(5) 0.0798(15) Uani 1 1 d . . .
O3 O 0.8508(4) 0.5998(6) 0.9092(3) 0.0577(10) Uani 1 1 d . . .
H3A H 0.896(6) 0.150(9) 0.876(4) 0.040(13) Uiso 1 1 d . . .
H3B H 0.927(7) 0.340(11) 0.893(5) 0.055(17) Uiso 1 1 d . . .
H3C H 1.019(5) 0.183(7) 0.957(4) 0.029(11) Uiso 1 1 d . . .
H1 H 0.6227 0.9074 0.7416 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
C1 0.039(2) 0.052(3) 0.058(3) 0.006(2) 0.010(2) -0.001(2)
C2 0.045(2) 0.047(2) 0.047(2) 0.009(2) 0.0048(18) 0.003(2)
C3 0.043(2) 0.039(2) 0.056(3) 0.004(2) 0.007(2) 0.001(2)
C4 0.089(5) 0.093(5) 0.099(5) 0.005(4) 0.041(4) 0.044(5)
C5 0.049(3) 0.052(3) 0.063(3) 0.000(2) 0.007(2) 0.001(2)
C6 0.054(3) 0.061(3) 0.050(3) -0.003(3) 0.015(2) 0.002(3)
C7 0.080(4) 0.083(4) 0.055(3) -0.016(3) 0.014(3) -0.016(4)
C8 0.084(5) 0.149(9) 0.047(3) -0.029(5) 0.003(3) -0.010(5)
C9 0.092(5) 0.183(12) 0.041(3) 0.008(6) 0.010(3) 0.007(7)
C10 0.127(7) 0.103(7) 0.080(5) 0.039(5) 0.043(5) 0.030(6)
C11 0.064(3) 0.067(4) 0.070(4) 0.011(3) 0.021(3) 0.005(3)
Cl1 0.0641(8) 0.0489(7) 0.0962(11) 0.0251(7) 0.0138(7) -0.0032(6)
Cl2 0.1104(15) 0.1023(16) 0.167(2) -0.0297(16) 0.0880(15) 0.0094(13)
Cl3 0.0679(9) 0.1210(18) 0.1016(13) 0.0299(13) -0.0270(9) -0.0418(12)
N1 0.043(2) 0.0373(19) 0.047(2) -0.0041(18) -0.0048(17) 0.0040(19)
O1 0.072(3) 0.071(3) 0.089(3) 0.043(3) -0.018(2) -0.010(2)
O2 0.069(3) 0.0283(19) 0.127(4) -0.001(2) -0.007(3) -0.0013(17)
O3 0.061(2) 0.0394(18) 0.059(2) -0.0081(16) -0.0133(17) 0.0088(16)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#
_geom_special_details            
; All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.523(7) . ?
C1 Cl1 1.756(5) . ?
C1 Cl2 1.756(6) . ?
C1 Cl3 1.757(5) . ?
C2 O1 1.401(6) . ?
C2 C3 1.547(7) . ?
C2 H2 0.9800 . ?
C3 O2 1.220(7) . ?
C3 O3 1.238(6) . ?
C4 C5 1.509(9) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 N1 1.479(7) . ?
C5 C6 1.521(8) . ?
C5 H5 0.9800 . ?
C6 C11 1.379(9) . ?
C6 C7 1.380(9) . ?
C7 C8 1.373(11) . ?
C7 H6 0.9300 . ?
C8 C9 1.326(16) . ?
C8 H7 0.9300 . ?
C9 C10 1.353(14) . ?
C9 H8 0.9300 . ?
C10 C11 1.401(10) . ?
C10 H9 0.9300 . ?
C11 H10 0.9300 . ?
N1 H3A 0.86(6) . ?
N1 H3B 0.88(7) . ?
N1 H3C 0.86(5) . ?
O1 H1 0.960 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Cl1 111.7(3) . . ?
C2 C1 Cl2 111.6(4) . . ?
Cl1 C1 Cl2 108.3(3) . . ?
C2 C1 Cl3 109.8(4) . . ?
Cl1 C1 Cl3 105.9(3) . . ?
Cl2 C1 Cl3 109.4(3) . . ?
O1 C2 C1 109.2(4) . . ?
O1 C2 C3 109.4(4) . . ?
C1 C2 C3 113.6(4) . . ?
O1 C2 H2 108.2 . . ?
C1 C2 H2 108.2 . . ?
C3 C2 H2 108.2 . . ?
O2 C3 O3 125.0(5) . . ?
O2 C3 C2 116.6(5) . . ?
O3 C3 C2 118.3(4) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C5 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C4 108.5(5) . . ?
N1 C5 C6 109.2(4) . . ?
C4 C5 C6 114.6(5) . . ?
N1 C5 H5 108.1 . . ?
C4 C5 H5 108.1 . . ?
C6 C5 H5 108.1 . . ?
C11 C6 C7 118.4(6) . . ?
C11 C6 C5 120.2(6) . . ?
C7 C6 C5 121.4(6) . . ?
C8 C7 C6 119.9(8) . . ?
C8 C7 H6 120.1 . . ?
C6 C7 H6 120.1 . . ?
C9 C8 C7 122.5(8) . . ?
C9 C8 H7 118.8 . . ?
C7 C8 H7 118.8 . . ?
C8 C9 C10 118.9(8) . . ?
C8 C9 H8 120.6 . . ?
C10 C9 H8 120.6 . . ?
C9 C10 C11 121.2(9) . . ?
C9 C10 H9 119.4 . . ?
C11 C10 H9 119.4 . . ?
C6 C11 C10 119.1(7) . . ?
C6 C11 H10 120.4 . . ?
C10 C11 H10 120.4 . . ?
C5 N1 H3A 117(3) . . ?
C5 N1 H3B 106(4) . . ?
H3A N1 H3B 98(5) . . ?
C5 N1 H3C 118(3) . . ?
H3A N1 H3C 102(5) . . ?
H3B N1 H3C 113(5) . . ?
C2 O1 H1 95.0 . . ?
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
Cl1 C1 C2 O1 170.2(4) . . . . ?
Cl2 C1 C2 O1 -68.4(5) . . . . ?
Cl3 C1 C2 O1 53.1(5) . . . . ?
Cl1 C1 C2 C3 -67.4(5) . . . . ?
Cl2 C1 C2 C3 54.0(5) . . . . ?
Cl3 C1 C2 C3 175.4(4) . . . . ?
O1 C2 C3 O2 10.2(7) . . . . ?
C1 C2 C3 O2 -112.0(6) . . . . ?
O1 C2 C3 O3 -169.4(5) . . . . ?
C1 C2 C3 O3 68.4(6) . . . . ?
N1 C5 C6 C11 117.3(5) . . . . ?
C4 C5 C6 C11 -120.7(7) . . . . ?
N1 C5 C6 C7 -60.8(7) . . . . ?
C4 C5 C6 C7 61.2(8) . . . . ?
C11 C6 C7 C8 -0.4(10) . . . . ?
C5 C6 C7 C8 177.7(6) . . . . ?
C6 C7 C8 C9 0.8(12) . . . . ?
C7 C8 C9 C10 0.8(14) . . . . ?
C8 C9 C10 C11 -2.8(14) . . . . ?
C7 C6 C11 C10 -1.5(9) . . . . ?
C5 C6 C11 C10 -179.6(6) . . . . ?
C9 C10 C11 C6 3.1(12) . . . . ?
#END


