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



data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Douglas Young'
'Jean-Damien Charrier'
'David S. Hadfield'
'Peter B. Hitchcock'

_publ_contact_author_name        'Prof Douglas Young'
_publ_contact_author_address     
;
Department of Chemistry
University of Sussex
University of Sussex
Falmer, Brighton
Brighton
Eat Sussex
UNITED KINGDOM
;

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

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Synthesis of (2S, 4S)- and (2S, 4R)-
5-Fluoroleucine and (2S, 4S)-[5, 5-2H2]-5-Fluoroleucine
;
_publ_requested_category         FO

data_(1a)-apr2500
_database_code_depnum_ccdc_archive 'CCDC 224897'

_audit_creation_date             2000-04-26T11:33:25-00:00
_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         'C6 H12 F1 N1 O2'
_chemical_formula_structural     'C6 H12 F N O2'
_chemical_formula_sum            'C6 H12 F N O2'
_chemical_formula_weight         149.17
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_Int_Tables_number      5

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

_cell_length_a                   9.6878(16)
_cell_length_b                   5.3021(6)
_cell_length_c                   15.229(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.292(5)
_cell_angle_gamma                90
_cell_volume                     746.89(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    19825
_cell_measurement_theta_min      3.705
_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          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_special_details           
;
?
;

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

_exptl_absorpt_coefficient_mu    0.11
_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            4317
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0602
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.2
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_reflns_number_total             1290
_reflns_number_gt                1089
_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          
;
The F atom is disordered over 2 positions. There should be another H atom
but it was not clear from a difference map whether it was in a NH3+ group or
a CO2H group so it was omitted.

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^)+(0.1100P)^2^+0.2496P] 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_number_reflns         1290
_refine_ls_number_parameters     105
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1826
_refine_ls_wR_factor_gt          0.1735
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0
_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(3)
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.057

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 0.0327(3) -0.0067(4) 0.1283(2) 0.0608(9) Uani 1 1 d . . .
O2 O -0.0691(2) 0.3650(4) 0.09079(16) 0.0437(7) Uani 1 1 d . . .
N N 0.1790(4) 0.5797(6) 0.0830(2) 0.0441(8) Uani 1 1 d . . .
H1B H 0.254(5) 0.623(9) 0.093(3) 0.051(13) Uiso 1 1 d . . .
H1A H 0.144(4) 0.546(7) 0.016(3) 0.046(10) Uiso 1 1 d . . .
C1 C 0.0395(4) 0.2225(6) 0.1168(2) 0.0383(8) Uani 1 1 d . . .
C2 C 0.1881(3) 0.3496(7) 0.1411(3) 0.0440(9) Uani 1 1 d . . .
H2 H 0.2598 0.2296 0.1287 0.053 Uiso 1 1 calc R . .
C3 C 0.2406(5) 0.4332(8) 0.2416(3) 0.0575(11) Uani 1 1 d . B .
H3A H 0.33 0.5333 0.2506 0.069 Uiso 1 1 calc R . .
H3B H 0.1667 0.5472 0.2529 0.069 Uiso 1 1 calc R . .
C4 C 0.2713(6) 0.2293(11) 0.3135(3) 0.0765(14) Uani 1 1 d . . .
H4 H 0.187 0.1112 0.2991 0.092 Uiso 1 1 calc R A 1
C6 C 0.2892(11) 0.352(2) 0.4106(5) 0.166(5) Uani 1 1 d . B .
H6A H 0.2014 0.4456 0.409 0.249 Uiso 1 1 calc R . .
H6B H 0.3721 0.467 0.4258 0.249 Uiso 1 1 calc R . .
H6C H 0.3054 0.2188 0.4572 0.249 Uiso 1 1 calc R . .
C5 C 0.4012(9) 0.0855(17) 0.3142(5) 0.113(2) Uani 0.564(15) 1 d P B 1
H5A1 H 0.3875 0.0062 0.2533 0.136 Uiso 0.564(15) 1 calc PR B 1
H5A2 H 0.4854 0.2002 0.3266 0.136 Uiso 0.564(15) 1 calc PR B 1
F F 0.4267(16) -0.101(3) 0.3822(9) 0.204(7) Uani 0.564(15) 1 d P B 1
C5A C 0.4012(9) 0.0855(17) 0.3142(5) 0.113(2) Uani 0.436(15) 1 d P B 2
H5A H 0.4134 -0.0617 0.3558 0.136 Uiso 0.436(15) 1 calc PR B 2
H5B H 0.3949 0.025 0.2516 0.136 Uiso 0.436(15) 1 calc PR B 2
F1A F 0.5212(11) 0.2624(18) 0.3472(6) 0.112(4) Uiso 0.436(15) 1 d P B 2

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 0.0488(17) 0.0423(18) 0.095(2) 0.0080(14) 0.0278(15) -0.0021(11)
O2 0.0292(12) 0.0487(15) 0.0533(14) 0.0090(11) 0.0122(10) -0.0024(10)
N 0.0308(15) 0.0516(18) 0.0515(19) -0.0050(14) 0.0148(13) -0.0150(13)
C1 0.0348(19) 0.040(2) 0.0430(18) -0.0021(15) 0.0163(14) -0.0031(15)
C2 0.0276(15) 0.053(2) 0.052(2) 0.0003(17) 0.0136(14) 0.0003(15)
C3 0.047(2) 0.069(3) 0.054(2) -0.0019(18) 0.0107(18) 0.0013(18)
C4 0.064(3) 0.102(3) 0.053(3) 0.016(3) 0.003(2) -0.013(3)
C6 0.168(8) 0.261(13) 0.067(4) 0.043(6) 0.030(5) 0.105(9)
C5 0.135(6) 0.095(4) 0.097(5) 0.010(4) 0.015(4) 0.027(5)
F 0.234(13) 0.180(12) 0.182(11) 0.059(8) 0.039(9) 0.064(10)
C5A 0.135(6) 0.095(4) 0.097(5) 0.010(4) 0.015(4) 0.027(5)

#----------------------------------------------------------------------------#
#                   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 1.232(4) . ?
O2 C1 1.259(4) . ?
N C2 1.494(5) . ?
C1 C2 1.533(5) . ?
C2 C3 1.529(6) . ?
C3 C4 1.503(6) . ?
C4 C5 1.468(10) . ?
C4 C6 1.577(10) . ?
C5 F 1.400(14) . ?

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
O1 C1 O2 124.2(3) . . ?
O1 C1 C2 119.0(3) . . ?
O2 C1 C2 116.7(3) . . ?
N C2 C3 107.5(3) . . ?
N C2 C1 109.3(3) . . ?
C3 C2 C1 112.2(3) . . ?
C4 C3 C2 117.1(4) . . ?
C5 C4 C3 111.3(5) . . ?
C5 C4 C6 110.6(5) . . ?
C3 C4 C6 109.2(6) . . ?
F C5 C4 109.6(8) . . ?

#===END

data_(19)-jan399
_database_code_depnum_ccdc_archive 'CCDC 224898'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H36 N2 O5'
_chemical_formula_weight         420.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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                   9.005(2)
_cell_length_b                   16.541(5)
_cell_length_c                   16.841(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2508.5(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      7
_cell_measurement_theta_max      10

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       \w--2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6576
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0976
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         27.97
_reflns_number_total             6028
_reflns_number_gt                2531
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Enraf-Nonius CAD4'
_computing_cell_refinement       'Enraf-Nonius CAD4'
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  SHELXL-93

_refine_special_details          
;
Hydrogen atoms on N1 and N2 were freely refined; other hydrogen atoms were
in riding mode. The absolute structure was assigned on the basis of the
known stereochemistry at C7.
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^)+(0.0565P)^2^+0.0000P] 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   1.5(18)
_refine_ls_number_reflns         6028
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1789
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.1668
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1499(2) 0.24454(17) 0.45580(16) 0.0883(9) Uani 1 1 d . . .
O2 O 0.2641(2) 0.28456(16) 0.17273(13) 0.0709(7) Uani 1 1 d . . .
O3 O 0.5069(3) 0.2647(2) 0.14957(17) 0.1158(12) Uani 1 1 d . . .
O4 O 0.7730(2) 0.16718(14) 0.29100(15) 0.0720(7) Uani 1 1 d . . .
O5 O 0.5545(3) 0.10736(18) 0.26054(19) 0.1034(11) Uani 1 1 d . . .
N1 N 0.3662(4) 0.1804(2) 0.46472(19) 0.0680(9) Uani 1 1 d . . .
H1N H 0.455(4) 0.190(2) 0.471(2) 0.074(12) Uiso 1 1 d . . .
N2 N 0.5651(3) 0.2350(2) 0.30579(18) 0.0636(8) Uani 1 1 d . . .
H2N H 0.622(4) 0.2747(17) 0.3128(17) 0.051(10) Uiso 1 1 d . . .
C1 C 0.2915(4) 0.0930(2) 0.5768(2) 0.0644(10) Uani 1 1 d . . .
C2 C 0.1979(5) 0.0345(3) 0.6080(3) 0.0979(15) Uani 1 1 d . . .
H2 H 0.1424 0.0023 0.5738 0.117 Uiso 1 1 calc R . .
C3 C 0.1858(6) 0.0232(3) 0.6901(4) 0.115(2) Uani 1 1 d . . .
H3 H 0.1245 -0.0169 0.7109 0.138 Uiso 1 1 calc R . .
C4 C 0.2655(7) 0.0719(4) 0.7386(4) 0.1145(19) Uani 1 1 d . . .
H4 H 0.2569 0.0654 0.7933 0.137 Uiso 1 1 calc R . .
C5 C 0.3568(5) 0.1292(3) 0.7102(3) 0.0901(13) Uani 1 1 d . . .
H5 H 0.4108 0.1613 0.7452 0.108 Uiso 1 1 calc R . .
C6 C 0.3706(4) 0.1407(2) 0.6298(3) 0.0716(10) Uani 1 1 d . . .
H6 H 0.4336 0.1808 0.6107 0.086 Uiso 1 1 calc R . .
C7 C 0.3060(4) 0.1025(2) 0.4879(2) 0.0716(11) Uani 1 1 d . . .
H7 H 0.2060 0.0985 0.4653 0.086 Uiso 1 1 calc R . .
C8 C 0.3993(5) 0.0350(3) 0.4511(3) 0.1052(14) Uani 1 1 d . . .
H8C H 0.3540 -0.0163 0.4621 0.158 Uiso 1 1 calc R . .
H8B H 0.4975 0.0361 0.4733 0.158 Uiso 1 1 calc R . .
H8A H 0.4052 0.0427 0.3947 0.158 Uiso 1 1 calc R . .
C9 C 0.2853(4) 0.2461(2) 0.44981(18) 0.0566(8) Uani 1 1 d . . .
C10 C 0.3680(4) 0.3197(2) 0.42143(19) 0.0608(9) Uani 1 1 d . . .
H10 H 0.4730 0.3139 0.4357 0.073 Uiso 1 1 calc R . .
C11 C 0.3074(5) 0.3952(2) 0.4604(3) 0.0908(12) Uani 1 1 d . . .
H11C H 0.3176 0.3907 0.5170 0.136 Uiso 1 1 calc R . .
H11B H 0.2044 0.4013 0.4471 0.136 Uiso 1 1 calc R . .
H11A H 0.3618 0.4414 0.4420 0.136 Uiso 1 1 calc R . .
C12 C 0.3557(4) 0.3268(2) 0.33031(19) 0.0620(9) Uani 1 1 d . . .
H12B H 0.2521 0.3352 0.3167 0.074 Uiso 1 1 calc R . .
H12A H 0.4099 0.3746 0.3136 0.074 Uiso 1 1 calc R . .
C13 C 0.4129(3) 0.2550(2) 0.28345(17) 0.0591(9) Uani 1 1 d . . .
H13 H 0.3502 0.2084 0.2963 0.071 Uiso 1 1 calc R . .
C14 C 0.4043(4) 0.2686(2) 0.1944(2) 0.0742(11) Uani 1 1 d . . .
C15 C 0.2242(5) 0.2924(3) 0.0884(2) 0.0780(11) Uani 1 1 d . . .
C16 C 0.3152(5) 0.3574(3) 0.0479(2) 0.1122(17) Uani 1 1 d . . .
H16C H 0.2837 0.3628 -0.0063 0.168 Uiso 1 1 calc R . .
H16B H 0.4184 0.3428 0.0494 0.168 Uiso 1 1 calc R . .
H16A H 0.3014 0.4079 0.0751 0.168 Uiso 1 1 calc R . .
C17 C 0.2378(6) 0.2106(3) 0.0498(3) 0.1176(17) Uani 1 1 d . . .
H17C H 0.1974 0.2128 -0.0029 0.176 Uiso 1 1 calc R . .
H17B H 0.1841 0.1714 0.0805 0.176 Uiso 1 1 calc R . .
H17A H 0.3405 0.1954 0.0472 0.176 Uiso 1 1 calc R . .
C18 C 0.0618(5) 0.3180(3) 0.0932(2) 0.1048(16) Uani 1 1 d . . .
H18C H 0.0072 0.2791 0.1238 0.157 Uiso 1 1 calc R . .
H18B H 0.0209 0.3210 0.0406 0.157 Uiso 1 1 calc R . .
H18A H 0.0550 0.3701 0.1182 0.157 Uiso 1 1 calc R . .
C19 C 0.6242(4) 0.1646(3) 0.2824(2) 0.0684(10) Uani 1 1 d . . .
C20 C 0.8684(4) 0.1014(2) 0.2622(2) 0.0693(10) Uani 1 1 d . . .
C21 C 1.0220(5) 0.1345(3) 0.2817(3) 0.1030(15) Uani 1 1 d . . .
H21C H 1.0359 0.1854 0.2553 0.155 Uiso 1 1 calc R . .
H21B H 1.0963 0.0970 0.2640 0.155 Uiso 1 1 calc R . .
H21A H 1.0307 0.1420 0.3380 0.155 Uiso 1 1 calc R . .
C22 C 0.8345(6) 0.0251(3) 0.3058(3) 0.1141(17) Uani 1 1 d . . .
H22C H 0.9009 -0.0168 0.2885 0.171 Uiso 1 1 calc R . .
H22B H 0.7339 0.0091 0.2952 0.171 Uiso 1 1 calc R . .
H22A H 0.8469 0.0337 0.3618 0.171 Uiso 1 1 calc R . .
C23 C 0.8478(5) 0.0913(3) 0.1745(2) 0.1108(16) Uani 1 1 d . . .
H23C H 0.7472 0.0757 0.1637 0.166 Uiso 1 1 calc R . .
H23B H 0.9142 0.0503 0.1553 0.166 Uiso 1 1 calc R . .
H23A H 0.8690 0.1415 0.1482 0.166 Uiso 1 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
O1 0.0407(13) 0.104(2) 0.120(2) 0.0290(19) 0.0039(14) 0.0039(15)
O2 0.0528(15) 0.109(2) 0.0508(14) 0.0003(13) 0.0049(11) -0.0043(13)
O3 0.0642(17) 0.198(4) 0.085(2) 0.013(2) 0.0247(15) 0.003(2)
O4 0.0458(14) 0.0676(16) 0.1026(19) -0.0169(15) -0.0073(13) 0.0049(13)
O5 0.0691(19) 0.086(2) 0.155(3) -0.043(2) 0.0034(18) -0.0272(17)
N1 0.0395(17) 0.081(2) 0.084(2) 0.0228(18) -0.0061(17) -0.0055(18)
N2 0.0405(16) 0.062(2) 0.088(2) -0.0079(18) -0.0049(15) -0.0079(17)
C1 0.0412(18) 0.059(2) 0.093(3) 0.026(2) 0.005(2) 0.008(2)
C2 0.060(2) 0.076(3) 0.158(5) 0.045(3) 0.002(3) -0.003(2)
C3 0.074(3) 0.098(4) 0.171(6) 0.081(4) 0.030(4) 0.010(3)
C4 0.101(4) 0.120(5) 0.123(4) 0.057(4) 0.026(4) 0.036(4)
C5 0.102(4) 0.089(3) 0.080(3) 0.023(2) 0.006(3) 0.024(3)
C6 0.057(2) 0.072(2) 0.087(3) 0.017(2) 0.001(2) 0.006(2)
C7 0.057(2) 0.068(2) 0.089(3) 0.010(2) -0.012(2) -0.008(2)
C8 0.123(4) 0.087(3) 0.106(3) -0.014(3) 0.002(3) -0.010(3)
C9 0.0447(18) 0.075(2) 0.0499(19) 0.0073(18) -0.0034(17) 0.002(2)
C10 0.0480(19) 0.075(2) 0.059(2) 0.0070(19) -0.0050(17) -0.001(2)
C11 0.103(3) 0.087(3) 0.083(3) -0.008(2) 0.001(3) 0.005(3)
C12 0.0444(18) 0.079(2) 0.062(2) 0.0177(19) 0.0009(17) 0.0019(19)
C13 0.0396(17) 0.079(2) 0.058(2) 0.004(2) 0.0018(16) -0.0076(18)
C14 0.051(2) 0.107(3) 0.064(2) 0.000(2) 0.007(2) -0.007(2)
C15 0.076(3) 0.111(3) 0.047(2) -0.004(2) 0.001(2) -0.001(3)
C16 0.127(4) 0.139(4) 0.071(3) 0.024(3) 0.017(3) -0.012(3)
C17 0.129(4) 0.138(4) 0.086(3) -0.037(3) -0.001(3) -0.003(4)
C18 0.088(3) 0.155(4) 0.072(3) -0.007(3) -0.024(2) 0.017(3)
C19 0.059(2) 0.066(3) 0.080(3) -0.011(2) 0.001(2) -0.007(2)
C20 0.073(3) 0.067(2) 0.069(3) -0.008(2) 0.007(2) 0.013(2)
C21 0.063(3) 0.111(4) 0.135(4) -0.027(3) -0.012(3) 0.029(2)
C22 0.142(4) 0.082(3) 0.118(4) 0.009(3) 0.020(3) 0.019(3)
C23 0.113(4) 0.147(4) 0.072(3) -0.017(3) 0.011(3) -0.012(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.224(4) . ?
O2 C14 1.340(4) . ?
O2 C15 1.471(4) . ?
O3 C14 1.195(4) . ?
O4 C19 1.349(4) . ?
O4 C20 1.468(4) . ?
O5 C19 1.194(4) . ?
N1 C9 1.332(5) . ?
N1 C7 1.452(5) . ?
N2 C19 1.340(4) . ?
N2 C13 1.459(4) . ?
C1 C2 1.387(5) . ?
C1 C6 1.388(5) . ?
C1 C7 1.512(5) . ?
C2 C3 1.400(7) . ?
C3 C4 1.353(7) . ?
C4 C5 1.343(7) . ?
C5 C6 1.372(5) . ?
C7 C8 1.530(5) . ?
C9 C10 1.505(5) . ?
C10 C11 1.513(5) . ?
C10 C12 1.543(4) . ?
C12 C13 1.517(5) . ?
C13 C14 1.519(4) . ?
C15 C17 1.507(6) . ?
C15 C16 1.514(5) . ?
C15 C18 1.524(5) . ?
C20 C22 1.493(5) . ?
C20 C23 1.498(5) . ?
C20 C21 1.524(5) . ?

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
C14 O2 C15 120.7(3) . . ?
C19 O4 C20 121.5(3) . . ?
C9 N1 C7 124.8(3) . . ?
C19 N2 C13 119.6(3) . . ?
C2 C1 C6 117.7(4) . . ?
C2 C1 C7 120.0(4) . . ?
C6 C1 C7 122.3(3) . . ?
C1 C2 C3 121.0(5) . . ?
C4 C3 C2 118.4(5) . . ?
C5 C4 C3 122.0(6) . . ?
C4 C5 C6 120.3(5) . . ?
C5 C6 C1 120.6(4) . . ?
N1 C7 C1 113.0(3) . . ?
N1 C7 C8 109.5(3) . . ?
C1 C7 C8 111.9(3) . . ?
O1 C9 N1 120.8(4) . . ?
O1 C9 C10 122.5(3) . . ?
N1 C9 C10 116.6(3) . . ?
C9 C10 C11 110.5(3) . . ?
C9 C10 C12 110.0(3) . . ?
C11 C10 C12 110.0(3) . . ?
C13 C12 C10 115.6(3) . . ?
N2 C13 C12 111.3(3) . . ?
N2 C13 C14 109.6(3) . . ?
C12 C13 C14 112.4(3) . . ?
O3 C14 O2 124.6(3) . . ?
O3 C14 C13 125.2(3) . . ?
O2 C14 C13 110.2(3) . . ?
O2 C15 C17 108.5(3) . . ?
O2 C15 C16 111.4(3) . . ?
C17 C15 C16 113.6(3) . . ?
O2 C15 C18 102.0(3) . . ?
C17 C15 C18 110.5(4) . . ?
C16 C15 C18 110.2(4) . . ?
O5 C19 N2 124.8(4) . . ?
O5 C19 O4 125.5(4) . . ?
N2 C19 O4 109.6(3) . . ?
O4 C20 C22 110.2(3) . . ?
O4 C20 C23 109.7(3) . . ?
C22 C20 C23 111.5(4) . . ?
O4 C20 C21 101.2(3) . . ?
C22 C20 C21 112.5(4) . . ?
C23 C20 C21 111.4(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.97
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.031

#===END

data_(2)-apr1600
_database_code_depnum_ccdc_archive 'CCDC 224899'

_audit_creation_date             2000-04-18T09:07:56-00:00
_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         'C6 H12 F1 N1 O2'
_chemical_formula_structural     'C6 H12 F N O2'
_chemical_formula_sum            'C6 H12 F N O2'
_chemical_formula_weight         149.17
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.637(4)
_cell_length_b                   5.314(3)
_cell_length_c                   14.574(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.10(3)
_cell_angle_gamma                90
_cell_volume                     745.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5334
_cell_measurement_theta_min      3.705
_cell_measurement_theta_max      22.722
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_special_details           
;
?
;

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

_exptl_absorpt_coefficient_mu    0.11
_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            3162
_diffrn_reflns_av_R_equivalents  0.1751
_diffrn_reflns_av_sigmaI/netI    0.23
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.08
_diffrn_reflns_theta_max         22.77
_diffrn_reflns_theta_full        22.77
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             1844
_reflns_number_gt                853
_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          
;
*******    Diffraction was very weak ************************

For both independent molecules the F end of the chain showed large ADPs and
for one of the molecules the disorder could be resolved between a major(76%)
and a minor(24%) conformation. Hydrogen atoms on the N atoms were not located,
and H atoms in the disordered region were omitted.

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^)+(0.0852P)^2^+0.4395P] 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_number_reflns         1844
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2149
_refine_ls_R_factor_gt           0.1075
_refine_ls_wR_factor_ref         0.2851
_refine_ls_wR_factor_gt          0.2256
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_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   -4(5)
_refine_diff_density_max         0.3
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.065

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
F1 F -0.3422(13) 0.292(3) 0.5228(8) 0.158(6) Uani 1 1 d . . .
O1 O -0.2288(9) 0.2059(16) 0.8802(6) 0.058(3) Uani 1 1 d . . .
O2 O -0.1511(8) 0.5904(16) 0.9136(6) 0.049(2) Uani 1 1 d . . .
N1 N -0.4119(9) 0.7889(19) 0.9012(7) 0.049(3) Uani 1 1 d . . .
C1 C -0.2471(14) 0.441(3) 0.8843(8) 0.047(4) Uani 1 1 d . . .
C2 C -0.3816(11) 0.549(2) 0.8494(8) 0.036(3) Uani 1 1 d . . .
H2 H -0.4572 0.4245 0.859 0.043 Uiso 1 1 calc R . .
C3 C -0.3847(13) 0.622(3) 0.7467(8) 0.053(4) Uani 1 1 d . . .
H3B H -0.4705 0.7194 0.7314 0.064 Uiso 1 1 calc R . .
H3A H -0.3046 0.7336 0.7365 0.064 Uiso 1 1 calc R . .
C4 C -0.3797(14) 0.399(4) 0.6818(9) 0.070(5) Uani 1 1 d . . .
H4 H -0.3038 0.2809 0.7029 0.084 Uiso 1 1 calc R . .
C5 C -0.3501(19) 0.509(4) 0.5890(9) 0.103(7) Uani 1 1 d . . .
H5B H -0.4252 0.6263 0.5682 0.123 Uiso 1 1 calc R . .
H5A H -0.2611 0.6026 0.5929 0.123 Uiso 1 1 calc R . .
C6 C -0.5184(17) 0.264(3) 0.6761(11) 0.087(5) Uani 1 1 d . . .
H6C H -0.5361 0.1914 0.7361 0.131 Uiso 1 1 calc R . .
H6B H -0.5164 0.1297 0.6301 0.131 Uiso 1 1 calc R . .
H6A H -0.5923 0.3839 0.6583 0.131 Uiso 1 1 calc R . .
O1A O 0.2776(8) -0.1883(18) 0.8646(6) 0.055(3) Uani 1 1 d . . .
O2A O 0.3676(8) 0.1785(16) 0.9152(5) 0.051(3) Uani 1 1 d . . .
N1A N 0.1159(10) 0.395(2) 0.9302(6) 0.044(3) Uani 1 1 d . . .
C1A C 0.2639(13) 0.035(3) 0.8830(9) 0.048(4) Uani 1 1 d . . .
C2A C 0.1270(12) 0.171(2) 0.8667(8) 0.043(4) Uani 1 1 d . . .
H2A H 0.0501 0.0514 0.8788 0.052 Uiso 1 1 calc R . .
C3A C 0.1081(13) 0.261(2) 0.7663(8) 0.048(4) Uani 1 1 d . B .
H3A1 H 0.0214 0.3609 0.76 0.057 Uiso 1 1 calc R . .
H3A2 H 0.1859 0.3756 0.7541 0.057 Uiso 1 1 calc R . .
C4A C 0.1015(14) 0.060(3) 0.6931(11) 0.061(4) Uani 1 1 d . . .
H4A H 0.1844 -0.0505 0.7057 0.074 Uiso 1 1 calc R A 1
C6A C -0.0241(16) -0.106(3) 0.6977(11) 0.080(5) Uani 1 1 d . B .
H6A1 H -0.0208 -0.2384 0.651 0.12 Uiso 1 1 calc R . .
H6A2 H -0.1084 -0.0055 0.6865 0.12 Uiso 1 1 calc R . .
H6A3 H -0.0249 -0.1837 0.7588 0.12 Uiso 1 1 calc R . .
C5A C 0.115(4) 0.167(11) 0.598(3) 0.14(3) Uani 0.76(3) 1 d P B 1
H5A1 H 0.1989 0.2731 0.5956 0.173 Uiso 0.76(3) 1 calc PR B 1
H5A2 H 0.1201 0.0302 0.552 0.173 Uiso 0.76(3) 1 calc PR B 1
F1A F -0.0059(19) 0.311(3) 0.5812(9) 0.111(7) Uani 0.76(3) 1 d P B 1
C5AA C 0.087(9) 0.190(14) 0.599(5) 0.011(18) Uiso 0.24(3) 1 d P B 2
F1AA F 0.189(5) 0.422(11) 0.576(3) 0.102(19) Uiso 0.24(3) 1 d P B 2

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 0.136(9) 0.241(17) 0.097(8) -0.010(10) 0.013(6) -0.033(11)
O1 0.056(6) 0.028(7) 0.090(7) 0.006(5) 0.004(5) 0.002(5)
O2 0.044(5) 0.032(6) 0.072(6) -0.014(5) 0.005(4) 0.004(5)
N1 0.044(7) 0.041(8) 0.063(7) 0.001(6) 0.002(5) 0.012(6)
C1 0.062(10) 0.030(9) 0.049(8) 0.013(7) -0.012(7) -0.012(8)
C2 0.025(6) 0.023(8) 0.059(8) 0.009(7) 0.003(5) -0.001(6)
C3 0.045(8) 0.068(11) 0.045(8) 0.007(8) -0.009(6) -0.008(8)
C4 0.054(9) 0.111(14) 0.045(9) 0.002(10) -0.004(7) 0.028(10)
C5 0.121(15) 0.16(2) 0.032(9) -0.042(12) 0.012(9) -0.018(14)
C6 0.098(13) 0.083(14) 0.081(11) -0.030(10) 0.010(9) -0.026(11)
O1A 0.046(6) 0.038(7) 0.080(7) -0.018(5) 0.006(5) 0.010(5)
O2A 0.043(5) 0.053(7) 0.056(5) -0.002(5) -0.009(4) 0.001(5)
N1A 0.052(6) 0.034(7) 0.048(7) -0.018(5) 0.003(5) 0.007(5)
C1A 0.045(9) 0.054(11) 0.046(8) 0.007(8) 0.016(7) 0.031(8)
C2A 0.042(8) 0.041(9) 0.046(8) 0.004(7) -0.010(6) -0.003(7)
C3A 0.048(8) 0.036(9) 0.058(9) 0.005(7) -0.005(6) 0.000(6)
C4A 0.044(9) 0.063(11) 0.075(12) -0.018(10) -0.005(8) 0.009(8)
C6A 0.101(13) 0.053(11) 0.084(11) -0.012(10) -0.007(9) 0.001(10)
C5A 0.08(3) 0.24(6) 0.12(3) -0.05(3) 0.00(2) 0.05(3)
F1A 0.150(16) 0.102(12) 0.078(9) 0.012(8) -0.022(8) 0.001(12)

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

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C5 1.51(2) . ?
O1 C1 1.266(15) . ?
O2 C1 1.274(14) . ?
N1 C2 1.516(15) . ?
C1 C2 1.482(16) . ?
C2 C3 1.545(16) . ?
C3 C4 1.52(2) . ?
C4 C5 1.51(2) . ?
C4 C6 1.52(2) . ?
O1A C1A 1.223(15) . ?
O2A C1A 1.325(16) . ?
N1A C2A 1.515(15) . ?
C1A C2A 1.514(16) . ?
C2A C3A 1.539(15) . ?
C3A C4A 1.509(18) . ?
C4A C6A 1.503(18) . ?
C4A C5A 1.51(5) . ?
C4A C5AA 1.53(8) . ?
C5A F1A 1.40(4) . ?
C5AA F1AA 1.62(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
O1 C1 O2 122.0(13) . . ?
O1 C1 C2 119.2(12) . . ?
O2 C1 C2 118.7(12) . . ?
C1 C2 N1 110.0(10) . . ?
C1 C2 C3 113.6(10) . . ?
N1 C2 C3 106.1(10) . . ?
C4 C3 C2 114.1(11) . . ?
C5 C4 C6 109.9(12) . . ?
C5 C4 C3 105.6(14) . . ?
C6 C4 C3 110.2(12) . . ?
F1 C5 C4 107.2(16) . . ?
O1A C1A O2A 123.3(11) . . ?
O1A C1A C2A 122.2(14) . . ?
O2A C1A C2A 114.4(12) . . ?
C1A C2A N1A 111.7(10) . . ?
C1A C2A C3A 110.9(10) . . ?
N1A C2A C3A 109.1(10) . . ?
C4A C3A C2A 116.8(11) . . ?
C6A C4A C3A 112.8(12) . . ?
C6A C4A C5A 112(2) . . ?
C3A C4A C5A 112(3) . . ?
C6A C4A C5AA 106(3) . . ?
C3A C4A C5AA 108(3) . . ?
C5A C4A C5AA 11(4) . . ?
F1A C5A C4A 105(3) . . ?
C4A C5AA F1AA 120(5) . . ?

#===END