# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2004



data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Prof Douglas Young'
_publ_contact_author_address     
;
Department of Chemistry
University of Sussex
Falmer
Brighton
East Sussex
BN1 9QJ
UNITED KINGDOM
;

_publ_contact_author_email       D.W.YOUNG@SUSSEX.AC.UK

_publ_section_title              
;
Synthesis of (2S,3S)-4-fluoroisoleucine
;
_publ_requested_category         FO
loop_
_publ_author_name
'Douglas Young'
'Jean-Damien Charrier'
'David S. Hadfield'
P.B.Hitchcock

data_nov799
_database_code_depnum_ccdc_archive 'CCDC 227306'

_audit_creation_date             1999-11-04T15:22:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1beta5
_audit_conform_dict_location     
ftp://ftp.iucr.org/cifdics/cif_core_2.1beta5.dic

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

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C11 H19 N1 O5'
_chemical_formula_sum            'C11 H19 N1 O5'
_chemical_formula_weight         245.27
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration syn

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
_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                   6.4668(5)
_cell_length_b                   10.4584(4)
_cell_length_c                   19.4553(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1315.81(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    13232
_cell_measurement_theta_min      4.246
_cell_measurement_theta_max      25.028
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION NOT APPLIED
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_reflns_number            6633
_diffrn_reflns_av_R_equivalents  0.06
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.43
_diffrn_reflns_theta_max         25.12
_diffrn_reflns_theta_full        25.12
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_reflns_number_total             2280
_reflns_number_gt                2115
_reflns_threshold_expression     >2sigma(I)

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

_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.1980P] 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    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2280
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.1023
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(12)
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.036

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O1 O -0.2513(3) 0.42406(17) 0.25521(9) 0.0585(5) Uani 1 1 d . . .
O2 O 0.0759(3) 0.40866(14) 0.28843(8) 0.0458(4) Uani 1 1 d . . .
O3 O 0.1686(2) 0.84724(13) 0.48791(7) 0.0357(4) Uani 1 1 d . . .
H3B H 0.092(4) 0.907(3) 0.4933(13) 0.043(7) Uiso 1 1 d . . .
O4 O 0.3719(2) 0.47078(11) 0.49566(7) 0.0317(3) Uani 1 1 d . . .
O5 O 0.0733(2) 0.45103(12) 0.55622(7) 0.0348(4) Uani 1 1 d . . .
N1 N 0.0823(3) 0.58373(15) 0.46858(8) 0.0296(4) Uani 1 1 d . . .
H1 H -0.036(4) 0.600(2) 0.4826(11) 0.025(5) Uiso 1 1 d . . .
C1 C -0.1064(4) 0.4692(2) 0.28573(11) 0.0416(5) Uani 1 1 d . . .
C2 C -0.0965(4) 0.5925(2) 0.32550(13) 0.0428(6) Uani 1 1 d . . .
H2B H -0.176(4) 0.588(3) 0.3633(14) 0.052(8) Uiso 1 1 d . . .
H2A H -0.155(5) 0.662(3) 0.2964(15) 0.060(8) Uiso 1 1 d . . .
C3 C 0.1311(4) 0.61151(19) 0.34270(10) 0.0366(5) Uani 1 1 d . . .
H3 H 0.195(4) 0.674(2) 0.3104(12) 0.044(6) Uiso 1 1 d . . .
C4 C 0.2212(4) 0.4778(2) 0.33069(13) 0.0458(6) Uani 1 1 d . . .
H4B H 0.221(4) 0.433(3) 0.3715(13) 0.047(7) Uiso 1 1 d . . .
H4A H 0.345(4) 0.480(2) 0.3069(12) 0.041(6) Uiso 1 1 d . . .
C5 C 0.1781(3) 0.66192(17) 0.41521(10) 0.0308(4) Uani 1 1 d . . .
H5 H 0.326(3) 0.6610(17) 0.4213(9) 0.020(5) Uiso 1 1 d . . .
C6 C 0.1077(4) 0.80005(17) 0.42267(11) 0.0338(5) Uani 1 1 d . . .
H6B H -0.037(5) 0.805(2) 0.4180(12) 0.040(6) Uiso 1 1 d . . .
H6A H 0.174(4) 0.848(2) 0.3854(11) 0.035(6) Uiso 1 1 d . . .
C7 C 0.1920(3) 0.49966(16) 0.50640(9) 0.0260(4) Uani 1 1 d . . .
C8 C 0.1573(4) 0.35474(17) 0.60522(10) 0.0346(5) Uani 1 1 d . . .
C9 C 0.2214(5) 0.23460(19) 0.56718(13) 0.0434(6) Uani 1 1 d . . .
H9C H 0.257(5) 0.164(3) 0.6015(15) 0.070(8) Uiso 1 1 d . . .
H9B H 0.351(6) 0.249(3) 0.5386(17) 0.083(11) Uiso 1 1 d . . .
H9A H 0.102(5) 0.201(3) 0.5412(14) 0.060(8) Uiso 1 1 d . . .
C10 C 0.3357(5) 0.4106(2) 0.64529(13) 0.0541(7) Uani 1 1 d . . .
H10C H 0.463(6) 0.421(4) 0.6146(18) 0.089(11) Uiso 1 1 d . . .
H10B H 0.289(5) 0.487(3) 0.6642(14) 0.062(8) Uiso 1 1 d . . .
H10A H 0.360(4) 0.349(2) 0.6840(12) 0.049(7) Uiso 1 1 d . . .
C11 C -0.0286(5) 0.3300(3) 0.65058(16) 0.0584(7) Uani 1 1 d . . .
H11C H -0.059(5) 0.406(3) 0.6747(15) 0.066(9) Uiso 1 1 d . . .
H11B H 0.010(5) 0.270(3) 0.6900(16) 0.070(9) Uiso 1 1 d . . .
H11A H -0.141(6) 0.301(3) 0.6212(16) 0.067(10) 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
O1 0.0694(14) 0.0529(10) 0.0532(10) 0.0006(8) -0.0060(10) -0.0133(9)
O2 0.0635(11) 0.0336(7) 0.0404(8) -0.0015(6) 0.0043(7) -0.0009(8)
O3 0.0311(8) 0.0273(7) 0.0486(9) -0.0021(6) -0.0049(7) 0.0035(6)
O4 0.0290(7) 0.0243(6) 0.0418(7) 0.0041(5) -0.0007(6) 0.0018(5)
O5 0.0356(8) 0.0303(6) 0.0385(7) 0.0097(5) 0.0046(6) 0.0020(6)
N1 0.0265(9) 0.0266(8) 0.0355(9) 0.0034(6) 0.0044(7) 0.0013(7)
C1 0.0537(15) 0.0391(11) 0.0321(11) 0.0058(9) 0.0008(10) -0.0055(11)
C2 0.0480(14) 0.0415(12) 0.0390(12) 0.0001(9) -0.0060(11) 0.0058(11)
C3 0.0419(13) 0.0327(10) 0.0351(11) 0.0032(8) 0.0027(10) 0.0051(9)
C4 0.0547(16) 0.0426(13) 0.0401(13) -0.0055(10) 0.0026(11) 0.0107(11)
C5 0.0298(11) 0.0246(9) 0.0378(11) 0.0068(8) 0.0025(8) 0.0023(8)
C6 0.0379(13) 0.0263(9) 0.0372(11) 0.0051(8) -0.0030(10) 0.0023(8)
C7 0.0282(10) 0.0194(8) 0.0304(9) 0.0004(7) 0.0006(7) -0.0004(7)
C8 0.0465(13) 0.0233(9) 0.0340(10) 0.0078(7) -0.0049(9) -0.0014(9)
C9 0.0567(16) 0.0261(10) 0.0474(13) 0.0023(9) -0.0070(12) -0.0001(10)
C10 0.081(2) 0.0402(12) 0.0413(13) 0.0062(11) -0.0194(14) -0.0179(14)
C11 0.074(2) 0.0457(14) 0.0555(16) 0.0175(13) 0.0211(15) -0.0003(14)

#----------------------------------------------------------------------------#
#                   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
O1 C1 1.206(3) . ?
O2 C1 1.340(3) . ?
O2 C4 1.443(3) . ?
O3 C6 1.418(3) . ?
O4 C7 1.220(2) . ?
O5 C7 1.337(2) . ?
O5 C8 1.489(2) . ?
N1 C7 1.348(2) . ?
N1 C5 1.460(3) . ?
C1 C2 1.505(3) . ?
C2 C3 1.523(3) . ?
C3 C4 1.533(3) . ?
C3 C5 1.536(3) . ?
C5 C6 1.522(3) . ?
C8 C10 1.510(3) . ?
C8 C11 1.514(4) . ?
C8 C9 1.516(3) . ?

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
C1 O2 C4 111.01(17) . . ?
C7 O5 C8 120.79(16) . . ?
C7 N1 C5 122.01(17) . . ?
O1 C1 O2 121.2(2) . . ?
O1 C1 C2 128.5(2) . . ?
O2 C1 C2 110.3(2) . . ?
C1 C2 C3 105.4(2) . . ?
C2 C3 C4 102.40(19) . . ?
C2 C3 C5 115.95(18) . . ?
C4 C3 C5 112.21(17) . . ?
O2 C4 C3 107.3(2) . . ?
N1 C5 C6 109.70(17) . . ?
N1 C5 C3 112.15(16) . . ?
C6 C5 C3 110.75(16) . . ?
O3 C6 C5 109.44(16) . . ?
O4 C7 O5 125.27(16) . . ?
O4 C7 N1 124.75(17) . . ?
O5 C7 N1 109.97(17) . . ?
O5 C8 C10 110.33(16) . . ?
O5 C8 C11 101.47(19) . . ?
C10 C8 C11 111.8(2) . . ?
O5 C8 C9 110.34(17) . . ?
C10 C8 C9 111.3(2) . . ?
C11 C8 C9 111.1(2) . . ?

#===END

data_aug398
_database_code_depnum_ccdc_archive 'CCDC 227307'

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C27 H36 F N O4 Si'
_chemical_formula_weight         485.66
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration syn

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   9.811(7)
_cell_length_b                   13.067(6)
_cell_length_c                   11.121(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.99(4)
_cell_angle_gamma                90.00
_cell_volume                     1377.2(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      10
_cell_measurement_theta_max      15

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    1.061
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       ' Enraf-Nonius CAD4'
_diffrn_measurement_method       \w--2\q
_diffrn_standards_number         2
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2277
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0594
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.12
_diffrn_reflns_theta_max         60.06
_reflns_number_total             2152
_reflns_number_observed          1848
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       'Enraf-Nonius CAD4'
_computing_cell_refinement       'Enraf-Nonius CAD4'
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_publication_material  SHELXL-93

_refine_special_details          
;
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^
or flagged by the user for potential systematic errors.  Weighted R-factors
wR and all goodnesses 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 observed criterion
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      
'calc w=1/[\s^2^(Fo^2^)+(0.1053P)^2^+0.1825P] 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    riding
_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   0.05(7)
_refine_ls_number_reflns         2152
_refine_ls_number_parameters     307
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_obs          0.0635
_refine_ls_wR_factor_all         0.1749
_refine_ls_wR_factor_obs         0.1634
_refine_ls_goodness_of_fit_all   1.061
_refine_ls_goodness_of_fit_obs   1.083
_refine_ls_restrained_S_all      1.061
_refine_ls_restrained_S_obs      1.082
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Si Si 0.4528(2) 0.13520(12) 0.09269(13) 0.0412(4) Uani 1 d . .
F F 0.7380(7) 0.2625(6) 0.6405(5) 0.125(2) Uani 1 d . .
O1 O 0.1821(6) 0.1479(5) 0.4559(6) 0.092(2) Uani 1 d . .
O2 O 0.1374(5) 0.3452(4) 0.4053(5) 0.0609(12) Uani 1 d . .
O3 O 0.3220(5) 0.4358(4) 0.3779(5) 0.0678(14) Uani 1 d . .
O4 O 0.4482(5) 0.1764(3) 0.2321(4) 0.0488(10) Uani 1 d . .
N N 0.3454(5) 0.2674(4) 0.4261(5) 0.0469(12) Uani 1 d . .
C1 C 0.4926(6) 0.2683(5) 0.4235(5) 0.0480(15) Uani 1 d . .
H1 H 0.5389 0.3288 0.4682 0.058 Uiso 1 calc R .
C2 C 0.5531(7) 0.1716(6) 0.4968(5) 0.055(2) Uani 1 d . .
H2 H 0.6198 0.1378 0.4576 0.066 Uiso 1 calc R .
C3 C 0.4253(9) 0.1036(6) 0.4886(7) 0.066(2) Uani 1 d . .
H3A H 0.4197 0.0513 0.4255 0.079 Uiso 1 calc R .
H3B H 0.4320 0.0703 0.5678 0.079 Uiso 1 calc R .
C4 C 0.2980(8) 0.1710(5) 0.4551(6) 0.056(2) Uani 1 d . .
C5 C 0.6239(11) 0.1961(8) 0.6306(7) 0.088(3) Uani 1 d . .
H5A H 0.5560 0.2273 0.6690 0.106 Uiso 1 calc R .
H5B H 0.6568 0.1332 0.6749 0.106 Uiso 1 calc R .
C6 C 0.2659(6) 0.3580(5) 0.3998(6) 0.0479(15) Uani 1 d . .
C7 C 0.0360(7) 0.4310(6) 0.3830(8) 0.066(2) Uani 1 d . .
C8 C 0.0869(10) 0.5112(8) 0.4806(10) 0.097(3) Uani 1 d . .
H8A H 0.1719 0.5415 0.4696 0.146 Uiso 1 calc R .
H8B H 0.1053 0.4804 0.5616 0.146 Uiso 1 calc R .
H8C H 0.0159 0.5631 0.4732 0.146 Uiso 1 calc R .
C9 C -0.0972(9) 0.3828(9) 0.3989(11) 0.105(4) Uani 1 d . .
H9A H -0.1288 0.3316 0.3359 0.158 Uiso 1 calc R .
H9B H -0.1686 0.4344 0.3912 0.158 Uiso 1 calc R .
H9C H -0.0792 0.3517 0.4796 0.158 Uiso 1 calc R .
C10 C 0.0174(11) 0.4696(10) 0.2507(10) 0.115(4) Uani 1 d . .
H10A H -0.0152 0.4147 0.1931 0.172 Uiso 1 calc R .
H10B H 0.1062 0.4944 0.2412 0.172 Uiso 1 calc R .
H10C H -0.0504 0.5242 0.2343 0.172 Uiso 1 calc R .
C11 C 0.5100(6) 0.2694(5) 0.2908(5) 0.0471(14) Uani 1 d . .
H11A H 0.4625 0.3284 0.2458 0.057 Uiso 1 calc R .
H11B H 0.6091 0.2727 0.2921 0.057 Uiso 1 calc R .
C12 C 0.3958(7) -0.0027(5) 0.0889(6) 0.051(2) Uani 1 d . .
C13 C 0.2488(9) -0.0116(6) 0.1048(9) 0.079(2) Uani 1 d . .
H13A H 0.1851 0.0270 0.0407 0.118 Uiso 1 calc R .
H13B H 0.2467 0.0148 0.1848 0.118 Uiso 1 calc R .
H13C H 0.2208 -0.0822 0.0989 0.118 Uiso 1 calc R .
C14 C 0.3993(10) -0.0498(6) -0.0378(7) 0.075(2) Uani 1 d . .
H14A H 0.4930 -0.0444 -0.0486 0.112 Uiso 1 calc R .
H14B H 0.3346 -0.0137 -0.1036 0.112 Uiso 1 calc R .
H14C H 0.3725 -0.1206 -0.0396 0.112 Uiso 1 calc R .
C15 C 0.5000(9) -0.0633(6) 0.1896(8) 0.075(2) Uani 1 d . .
H15A H 0.5932 -0.0567 0.1779 0.113 Uiso 1 calc R .
H15B H 0.4733 -0.1342 0.1842 0.113 Uiso 1 calc R .
H15C H 0.4991 -0.0372 0.2701 0.113 Uiso 1 calc R .
C16 C 0.6386(6) 0.1459(5) 0.0800(5) 0.0451(13) Uani 1 d . .
C17 C 0.6744(8) 0.1709(6) -0.0288(6) 0.057(2) Uani 1 d . .
H17 H 0.6027 0.1840 -0.1002 0.069 Uiso 1 calc R .
C18 C 0.8131(8) 0.1772(7) -0.0353(7) 0.069(2) Uani 1 d . .
H18 H 0.8337 0.1927 -0.1103 0.083 Uiso 1 calc R .
C19 C 0.9190(8) 0.1603(7) 0.0689(8) 0.073(2) Uani 1 d . .
H19 H 1.0126 0.1652 0.0656 0.088 Uiso 1 calc R .
C20 C 0.8877(8) 0.1358(7) 0.1798(7) 0.072(2) Uani 1 d . .
H20 H 0.9598 0.1242 0.2513 0.086 Uiso 1 calc R .
C21 C 0.7494(7) 0.1289(7) 0.1835(6) 0.059(2) Uani 1 d . .
H21 H 0.7294 0.1121 0.2584 0.071 Uiso 1 calc R .
C22 C 0.3242(6) 0.2130(5) -0.0271(6) 0.0460(15) Uani 1 d . .
C23 C 0.2947(8) 0.1978(6) -0.1550(6) 0.063(2) Uani 1 d . .
H23 H 0.3459 0.1492 -0.1860 0.076 Uiso 1 calc R .
C24 C 0.1911(8) 0.2530(8) -0.2373(7) 0.075(2) Uani 1 d . .
H24 H 0.1738 0.2410 -0.3224 0.090 Uiso 1 calc R .
C25 C 0.1143(9) 0.3247(8) -0.1949(9) 0.081(2) Uani 1 d . .
H25 H 0.0433 0.3605 -0.2507 0.098 Uiso 1 calc R .
C26 C 0.1419(8) 0.3441(8) -0.0694(8) 0.081(2) Uani 1 d . .
H26 H 0.0931 0.3954 -0.0402 0.097 Uiso 1 calc R .
C27 C 0.2427(7) 0.2871(6) 0.0128(7) 0.060(2) Uani 1 d . .
H27 H 0.2569 0.2982 0.0977 0.072 Uiso 1 calc R .

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
Si 0.0482(8) 0.0378(8) 0.0377(8) 0.0016(7) 0.0114(6) 0.0012(8)
F 0.121(4) 0.145(6) 0.080(4) -0.007(4) -0.025(3) -0.006(5)
O1 0.081(4) 0.064(4) 0.142(5) 0.020(4) 0.049(4) -0.006(3)
O2 0.052(3) 0.048(3) 0.084(3) -0.006(2) 0.020(2) 0.007(2)
O3 0.060(3) 0.040(3) 0.107(4) 0.008(3) 0.030(3) 0.003(2)
O4 0.066(3) 0.042(2) 0.041(2) -0.004(2) 0.019(2) -0.005(2)
N 0.051(3) 0.042(3) 0.051(3) 0.002(2) 0.019(2) 0.005(2)
C1 0.049(3) 0.051(4) 0.044(3) -0.007(3) 0.012(3) 0.000(3)
C2 0.067(4) 0.066(4) 0.029(3) -0.002(3) 0.007(3) 0.026(4)
C3 0.091(6) 0.050(4) 0.061(4) 0.008(3) 0.027(4) 0.012(4)
C4 0.070(5) 0.046(4) 0.057(4) 0.002(3) 0.024(3) -0.001(3)
C5 0.101(6) 0.095(7) 0.052(4) -0.001(4) -0.008(4) 0.022(6)
C6 0.048(3) 0.047(4) 0.051(3) -0.011(3) 0.018(3) 0.001(3)
C7 0.054(4) 0.065(5) 0.074(5) -0.010(4) 0.010(3) 0.012(4)
C8 0.082(6) 0.082(6) 0.131(8) -0.051(6) 0.035(6) -0.003(5)
C9 0.057(5) 0.102(8) 0.159(9) -0.032(7) 0.033(5) -0.004(5)
C10 0.096(7) 0.126(10) 0.100(7) -0.002(7) -0.015(6) 0.055(7)
C11 0.055(4) 0.037(3) 0.051(3) -0.005(3) 0.016(3) -0.005(3)
C12 0.057(4) 0.037(3) 0.060(4) -0.003(3) 0.018(3) -0.004(3)
C13 0.075(5) 0.049(4) 0.115(7) -0.002(4) 0.031(5) -0.012(4)
C14 0.108(6) 0.044(4) 0.068(5) -0.015(4) 0.015(4) 0.002(4)
C15 0.100(6) 0.041(4) 0.081(5) 0.015(4) 0.015(5) 0.008(4)
C16 0.055(3) 0.036(3) 0.046(3) -0.001(3) 0.016(3) 0.002(3)
C17 0.065(4) 0.060(4) 0.048(3) 0.007(3) 0.016(3) 0.010(3)
C18 0.075(5) 0.073(5) 0.069(5) 0.011(4) 0.034(4) 0.008(4)
C19 0.059(4) 0.072(6) 0.097(6) 0.002(4) 0.034(4) 0.001(4)
C20 0.056(4) 0.075(5) 0.078(5) 0.008(5) 0.008(3) 0.006(5)
C21 0.058(4) 0.072(5) 0.047(3) 0.005(4) 0.012(3) 0.004(4)
C22 0.045(3) 0.044(3) 0.046(3) 0.005(3) 0.005(3) -0.003(3)
C23 0.071(5) 0.060(5) 0.051(4) 0.002(3) 0.004(3) -0.002(4)
C24 0.072(5) 0.097(6) 0.046(4) 0.019(4) -0.005(4) -0.012(5)
C25 0.068(5) 0.089(6) 0.079(6) 0.030(5) 0.006(4) 0.011(5)
C26 0.067(5) 0.087(6) 0.089(6) 0.015(5) 0.018(4) 0.025(5)
C27 0.057(4) 0.064(5) 0.058(4) 0.008(3) 0.012(3) 0.011(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si O4 1.654(4) . ?
Si C16 1.869(6) . ?
Si C22 1.879(6) . ?
Si C12 1.884(6) . ?
F C5 1.398(12) . ?
O1 C4 1.178(8) . ?
O2 C6 1.289(7) . ?
O2 C7 1.477(9) . ?
O3 C6 1.210(8) . ?
O4 C11 1.437(7) . ?
N C6 1.406(8) . ?
N C4 1.409(9) . ?
N C1 1.453(7) . ?
C1 C11 1.529(8) . ?
C1 C2 1.537(9) . ?
C2 C5 1.504(10) . ?
C2 C3 1.520(10) . ?
C3 C4 1.495(10) . ?
C7 C8 1.498(11) . ?
C7 C9 1.501(12) . ?
C7 C10 1.521(13) . ?
C12 C13 1.502(10) . ?
C12 C15 1.529(10) . ?
C12 C14 1.546(9) . ?
C16 C21 1.382(9) . ?
C16 C17 1.384(8) . ?
C17 C18 1.383(10) . ?
C18 C19 1.360(11) . ?
C19 C20 1.383(10) . ?
C20 C21 1.371(9) . ?
C22 C23 1.391(9) . ?
C22 C27 1.399(10) . ?
C23 C24 1.381(11) . ?
C24 C25 1.362(13) . ?
C25 C26 1.375(12) . ?
C26 C27 1.379(10) . ?

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
O4 Si C16 108.1(2) . . ?
O4 Si C22 108.2(3) . . ?
C16 Si C22 113.2(3) . . ?
O4 Si C12 104.6(3) . . ?
C16 Si C12 111.1(3) . . ?
C22 Si C12 111.1(3) . . ?
C6 O2 C7 121.2(6) . . ?
C11 O4 Si 126.2(4) . . ?
C6 N C4 127.0(5) . . ?
C6 N C1 119.4(5) . . ?
C4 N C1 113.6(5) . . ?
N C1 C11 112.3(5) . . ?
N C1 C2 103.4(5) . . ?
C11 C1 C2 113.3(5) . . ?
C5 C2 C3 110.3(6) . . ?
C5 C2 C1 111.5(6) . . ?
C3 C2 C1 104.5(5) . . ?
C4 C3 C2 107.1(6) . . ?
O1 C4 N 127.3(7) . . ?
O1 C4 C3 126.4(7) . . ?
N C4 C3 106.3(6) . . ?
F C5 C2 111.4(8) . . ?
O3 C6 O2 128.3(6) . . ?
O3 C6 N 119.5(5) . . ?
O2 C6 N 112.2(6) . . ?
O2 C7 C8 109.0(6) . . ?
O2 C7 C9 103.3(7) . . ?
C8 C7 C9 110.2(7) . . ?
O2 C7 C10 108.7(6) . . ?
C8 C7 C10 113.8(9) . . ?
C9 C7 C10 111.3(8) . . ?
O4 C11 C1 106.9(5) . . ?
C13 C12 C15 110.8(7) . . ?
C13 C12 C14 108.9(7) . . ?
C15 C12 C14 107.0(6) . . ?
C13 C12 Si 111.1(5) . . ?
C15 C12 Si 109.9(5) . . ?
C14 C12 Si 109.0(5) . . ?
C21 C16 C17 116.3(6) . . ?
C21 C16 Si 119.8(5) . . ?
C17 C16 Si 123.9(5) . . ?
C18 C17 C16 122.4(6) . . ?
C19 C18 C17 119.4(7) . . ?
C18 C19 C20 120.0(7) . . ?
C21 C20 C19 119.5(7) . . ?
C20 C21 C16 122.4(6) . . ?
C23 C22 C27 116.0(6) . . ?
C23 C22 Si 124.9(5) . . ?
C27 C22 Si 118.9(5) . . ?
C24 C23 C22 121.8(8) . . ?
C25 C24 C23 120.5(8) . . ?
C24 C25 C26 119.8(8) . . ?
C25 C26 C27 119.5(9) . . ?
C26 C27 C22 122.3(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 Si O4 C11 47.6(5) . . . . ?
C22 Si O4 C11 -75.4(5) . . . . ?
C12 Si O4 C11 166.0(5) . . . . ?
C6 N C1 C11 -75.6(7) . . . . ?
C4 N C1 C11 103.9(6) . . . . ?
C6 N C1 C2 161.9(5) . . . . ?
C4 N C1 C2 -18.6(7) . . . . ?
N C1 C2 C5 -96.6(7) . . . . ?
C11 C1 C2 C5 141.6(7) . . . . ?
N C1 C2 C3 22.4(6) . . . . ?
C11 C1 C2 C3 -99.4(6) . . . . ?
C5 C2 C3 C4 100.4(7) . . . . ?
C1 C2 C3 C4 -19.5(7) . . . . ?
C6 N C4 O1 4.4(11) . . . . ?
C1 N C4 O1 -175.0(7) . . . . ?
C6 N C4 C3 -174.0(6) . . . . ?
C1 N C4 C3 6.6(7) . . . . ?
C2 C3 C4 O1 -169.7(7) . . . . ?
C2 C3 C4 N 8.7(7) . . . . ?
C3 C2 C5 F -177.2(7) . . . . ?
C1 C2 C5 F -61.7(9) . . . . ?
C7 O2 C6 O3 0.3(10) . . . . ?
C7 O2 C6 N 178.9(5) . . . . ?
C4 N C6 O3 179.1(6) . . . . ?
C1 N C6 O3 -1.5(9) . . . . ?
C4 N C6 O2 0.3(9) . . . . ?
C1 N C6 O2 179.7(5) . . . . ?
C6 O2 C7 C8 -62.6(9) . . . . ?
C6 O2 C7 C9 -179.8(7) . . . . ?
C6 O2 C7 C10 61.9(9) . . . . ?
Si O4 C11 C1 -173.7(4) . . . . ?
N C1 C11 O4 -62.2(7) . . . . ?
C2 C1 C11 O4 54.5(7) . . . . ?
O4 Si C12 C13 61.1(6) . . . . ?
C16 Si C12 C13 177.5(5) . . . . ?
C22 Si C12 C13 -55.4(6) . . . . ?
O4 Si C12 C15 -61.9(5) . . . . ?
C16 Si C12 C15 54.5(6) . . . . ?
C22 Si C12 C15 -178.4(5) . . . . ?
O4 Si C12 C14 -178.9(5) . . . . ?
C16 Si C12 C14 -62.5(6) . . . . ?
C22 Si C12 C14 64.6(5) . . . . ?
O4 Si C16 C21 34.9(7) . . . . ?
C22 Si C16 C21 154.7(6) . . . . ?
C12 Si C16 C21 -79.4(7) . . . . ?
O4 Si C16 C17 -144.8(6) . . . . ?
C22 Si C16 C17 -25.0(7) . . . . ?
C12 Si C16 C17 100.9(6) . . . . ?
C21 C16 C17 C18 1.0(11) . . . . ?
Si C16 C17 C18 -179.3(6) . . . . ?
C16 C17 C18 C19 -1.4(12) . . . . ?
C17 C18 C19 C20 0.9(13) . . . . ?
C18 C19 C20 C21 0.0(13) . . . . ?
C19 C20 C21 C16 -0.3(13) . . . . ?
C17 C16 C21 C20 -0.2(12) . . . . ?
Si C16 C21 C20 -179.9(7) . . . . ?
O4 Si C22 C23 -177.3(6) . . . . ?
C16 Si C22 C23 62.9(7) . . . . ?
C12 Si C22 C23 -62.9(6) . . . . ?
O4 Si C22 C27 -2.5(6) . . . . ?
C16 Si C22 C27 -122.3(5) . . . . ?
C12 Si C22 C27 111.8(5) . . . . ?
C27 C22 C23 C24 0.2(10) . . . . ?
Si C22 C23 C24 175.1(6) . . . . ?
C22 C23 C24 C25 0.0(13) . . . . ?
C23 C24 C25 C26 1.5(14) . . . . ?
C24 C25 C26 C27 -3.2(14) . . . . ?
C25 C26 C27 C22 3.6(13) . . . . ?
C23 C22 C27 C26 -2.0(11) . . . . ?
Si C22 C27 C26 -177.2(6) . . . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.068