data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Jonathan Percy'
'Andrea Arany'
'Patrick J. Crowley'
'John Fawcett'
'Michael B. Hursthouse'
'Benson M. Kariuki'
'Mark E. Light'
'Andrew C. Moralee'
'Vittoria Salafia'

_publ_contact_author_name        'Prof Jonathan Percy'
_publ_contact_author_address     
;
Department of Chemistry
University of Leicester
University Road
Leicester
LE1 7RH
UNITED KINGDOM
;

_publ_contact_author_email       JMP29@LE.AC.UK

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Highly-functionalised Difluorinated
(Hydroxymethyl)conduritol Analogues via the Diels-Alder Reactions of a
Difluorinated Dienophile
;

_publ_section_references         
;
PLATON- (a) Spek, A. L. (1990) Acta Cryst. A46, C34.
(b) Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool,
Utrecht University, Utrecht, The Netherlands.
SHELXTL, program suite for structure solution and refinement,
Bruker AXS, Inc. 5465 East Cheryl Parkway, Nadison,
Wisconsin 53711-5373, USA
SMART, program for instrument control and data aquisition,
Bruker AXS, Inc. 5465 East Cheryl Parkway, Nadison,
Wisconsin 53711-5373, USA
SAINTPLUS, program suite for data processing,
Bruker AXS, Inc. 5465 East Cheryl Parkway, Nadison,
Wisconsin 53711-5373, USA
;

data_12a
_database_code_depnum_ccdc_archive 'CCDC 224031'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H19 F2 N O5'
_chemical_formula_weight         319.30
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'
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 0.0060 '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'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   16.3285(16)
_cell_length_b                   11.9385(11)
_cell_length_c                   17.5557(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.70(4)
_cell_angle_gamma                90.00
_cell_volume                     3057.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    351739
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_process_details   'SORTAV (Blessing, 1997)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      150(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  'Bruker Nonius Kappa CCD Area detector'
_diffrn_measurement_method       '\f and \w scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37999
_diffrn_reflns_av_R_equivalents  0.1526
_diffrn_reflns_av_sigmaI/netI    0.0940
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         24.95
_reflns_number_total             5330
_reflns_number_gt                2669
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_cell_refinement       'DENZO (Otwinowski and MInor, 1997)'
_computing_data_reduction        'DENZO, COLLECT, MAXUS (Mackay et al., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_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^)+(0.0799P)^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_number_reflns         5330
_refine_ls_number_parameters     403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1446
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1588
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      0.939
_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
F1 F 0.94137(13) 1.08522(15) 0.62695(11) 0.0435(5) Uani 1 1 d . . .
F2 F 0.91385(13) 1.06983(15) 0.73634(11) 0.0411(5) Uani 1 1 d . . .
N1 N 0.84834(18) 0.7804(2) 0.46529(15) 0.0340(7) Uani 1 1 d . . .
O1 O 1.08443(15) 0.91950(19) 0.71401(13) 0.0386(6) Uani 1 1 d . . .
O2 O 0.86207(16) 0.8060(2) 0.75256(13) 0.0409(6) Uani 1 1 d . . .
O3 O 0.77384(15) 0.90378(19) 0.63416(13) 0.0363(6) Uani 1 1 d . . .
O4 O 0.90532(15) 0.88655(18) 0.58310(12) 0.0319(6) Uani 1 1 d . . .
O5 O 0.86162(16) 0.70804(18) 0.59018(13) 0.0378(6) Uani 1 1 d . . .
C1 C 0.9306(2) 0.8959(3) 0.67196(18) 0.0300(8) Uani 1 1 d . . .
C2 C 0.9603(2) 1.0207(3) 0.6965(2) 0.0339(9) Uani 1 1 d . . .
C3 C 1.0630(2) 1.0116(3) 0.7545(2) 0.0373(9) Uani 1 1 d . . .
H3 H 1.0983 1.0802 0.7604 0.045 Uiso 1 1 calc R . .
C4 C 1.0732(2) 0.9613(3) 0.8367(2) 0.0385(9) Uani 1 1 d . . .
H4 H 1.0924 0.9973 0.8888 0.046 Uiso 1 1 calc R . .
C5 C 1.0492(2) 0.8551(3) 0.81945(19) 0.0359(9) Uani 1 1 d . . .
H5 H 1.0478 0.8011 0.8570 0.043 Uiso 1 1 calc R . .
C6 C 1.0245(2) 0.8391(3) 0.72572(19) 0.0331(8) Uani 1 1 d . . .
H6 H 1.0298 0.7621 0.7091 0.040 Uiso 1 1 calc R . .
C7 C 0.8522(2) 0.8606(3) 0.6914(2) 0.0324(8) Uani 1 1 d . . .
C8 C 0.6931(2) 0.8818(3) 0.6463(2) 0.0438(10) Uani 1 1 d . . .
H8A H 0.6914 0.9321 0.6890 0.053 Uiso 1 1 calc R . .
H8B H 0.6943 0.8054 0.6656 0.053 Uiso 1 1 calc R . .
C9 C 0.6110(3) 0.8997(4) 0.5629(2) 0.0665(13) Uani 1 1 d . . .
H9A H 0.6115 0.9748 0.5436 0.100 Uiso 1 1 calc R . .
H9B H 0.5564 0.8882 0.5696 0.100 Uiso 1 1 calc R . .
H9C H 0.6121 0.8476 0.5217 0.100 Uiso 1 1 calc R . .
C10 C 0.8702(2) 0.7838(3) 0.5479(2) 0.0316(8) Uani 1 1 d . . .
C11 C 0.8079(3) 0.6765(3) 0.4192(2) 0.0434(10) Uani 1 1 d . . .
H11C H 0.7709 0.6937 0.3593 0.052 Uiso 1 1 calc R . .
H11D H 0.7676 0.6453 0.4409 0.052 Uiso 1 1 calc R . .
C12 C 0.8786(3) 0.5902(3) 0.4274(2) 0.0623(13) Uani 1 1 d . . .
H12D H 0.9157 0.6183 0.4020 0.093 Uiso 1 1 calc R . .
H12E H 0.8484 0.5227 0.3988 0.093 Uiso 1 1 calc R . .
H12F H 0.9167 0.5745 0.4866 0.093 Uiso 1 1 calc R . .
C13 C 0.8637(2) 0.8734(3) 0.4185(2) 0.0412(9) Uani 1 1 d . . .
H13C H 0.8805 0.8435 0.3761 0.049 Uiso 1 1 calc R . .
H13D H 0.9143 0.9188 0.4578 0.049 Uiso 1 1 calc R . .
C14 C 0.7794(3) 0.9463(3) 0.3748(2) 0.0634(12) Uani 1 1 d . . .
H14D H 0.7287 0.9011 0.3372 0.095 Uiso 1 1 calc R . .
H14E H 0.7910 1.0037 0.3426 0.095 Uiso 1 1 calc R . .
H14F H 0.7651 0.9802 0.4170 0.095 Uiso 1 1 calc R . .
F1A F 0.44062(14) 0.58667(15) 0.13856(11) 0.0425(5) Uani 1 1 d . . .
F2A F 0.40651(13) 0.60603(15) 0.24352(12) 0.0424(5) Uani 1 1 d . . .
N1A N 0.35333(18) 0.8826(2) -0.02923(15) 0.0326(7) Uani 1 1 d . . .
O1A O 0.58276(15) 0.75275(19) 0.22945(13) 0.0363(6) Uani 1 1 d . . .
O2A O 0.35226(16) 0.8674(2) 0.25415(14) 0.0423(6) Uani 1 1 d . . .
O3A O 0.27050(15) 0.76786(19) 0.13437(13) 0.0370(6) Uani 1 1 d . . .
O4A O 0.40773(15) 0.78414(17) 0.09187(12) 0.0320(6) Uani 1 1 d . . .
O5A O 0.36811(16) 0.96616(18) 0.09341(13) 0.0376(6) Uani 1 1 d . . .
C1A C 0.4282(2) 0.7778(3) 0.17981(18) 0.0296(8) Uani 1 1 d . . .
C2A C 0.4554(2) 0.6527(3) 0.2059(2) 0.0333(9) Uani 1 1 d . . .
C3A C 0.5588(2) 0.6610(3) 0.26846(19) 0.0364(9) Uani 1 1 d . . .
H3A H 0.5945 0.5922 0.2767 0.044 Uiso 1 1 calc R . .
C4A C 0.5635(2) 0.7147(3) 0.34878(19) 0.0366(9) Uani 1 1 d . . .
H4A H 0.5791 0.6802 0.4010 0.044 Uiso 1 1 calc R . .
C5A C 0.5411(2) 0.8197(3) 0.32896(19) 0.0361(9) Uani 1 1 d . . .
H5A H 0.5379 0.8751 0.3648 0.043 Uiso 1 1 calc R . .
C6A C 0.5214(2) 0.8338(3) 0.23704(19) 0.0325(8) Uani 1 1 d . . .
H6A H 0.5283 0.9103 0.2206 0.039 Uiso 1 1 calc R . .
C7A C 0.3472(2) 0.8125(3) 0.1947(2) 0.0320(8) Uani 1 1 d . . .
C8A C 0.1880(2) 0.7792(3) 0.1454(2) 0.0448(10) Uani 1 1 d . . .
H8A1 H 0.1836 0.8544 0.1642 0.054 Uiso 1 1 calc R . .
H8A2 H 0.1889 0.7264 0.1878 0.054 Uiso 1 1 calc R . .
C9A C 0.1085(3) 0.7557(4) 0.0607(2) 0.0646(13) Uani 1 1 d . . .
H9A1 H 0.1095 0.8070 0.0190 0.097 Uiso 1 1 calc R . .
H9A2 H 0.0523 0.7647 0.0650 0.097 Uiso 1 1 calc R . .
H9A3 H 0.1127 0.6803 0.0437 0.097 Uiso 1 1 calc R . .
C10A C 0.3744(2) 0.8864(3) 0.0532(2) 0.0318(8) Uani 1 1 d . . .
C11A C 0.3141(2) 0.9828(3) -0.0811(2) 0.0404(9) Uani 1 1 d . . .
H11A H 0.2845 1.0279 -0.0546 0.048 Uiso 1 1 calc R . .
H11B H 0.2677 0.9604 -0.1370 0.048 Uiso 1 1 calc R . .
C12A C 0.3860(3) 1.0524(3) -0.0910(2) 0.0554(11) Uani 1 1 d . . .
H12A H 0.4273 1.0834 -0.0368 0.083 Uiso 1 1 calc R . .
H12B H 0.3568 1.1120 -0.1307 0.083 Uiso 1 1 calc R . .
H12C H 0.4196 1.0060 -0.1119 0.083 Uiso 1 1 calc R . .
C13A C 0.3601(2) 0.7801(3) -0.0722(2) 0.0413(9) Uani 1 1 d . . .
H13A H 0.4140 0.7385 -0.0341 0.050 Uiso 1 1 calc R . .
H13B H 0.3677 0.8003 -0.1222 0.050 Uiso 1 1 calc R . .
C14A C 0.2765(3) 0.7057(3) -0.0992(2) 0.0502(10) Uani 1 1 d . . .
H14A H 0.2715 0.6804 -0.0495 0.075 Uiso 1 1 calc R . .
H14B H 0.2825 0.6422 -0.1299 0.075 Uiso 1 1 calc R . .
H14C H 0.2226 0.7473 -0.1352 0.075 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
F1 0.0520(14) 0.0296(12) 0.0429(11) 0.0075(9) 0.0162(10) -0.0012(10)
F2 0.0397(12) 0.0330(12) 0.0493(12) -0.0085(9) 0.0187(10) 0.0021(9)
N1 0.0397(18) 0.0375(19) 0.0226(15) -0.0011(13) 0.0120(14) -0.0028(15)
O1 0.0369(15) 0.0358(15) 0.0428(13) -0.0036(11) 0.0176(12) 0.0011(12)
O2 0.0466(16) 0.0454(16) 0.0304(13) 0.0041(12) 0.0170(12) -0.0055(13)
O3 0.0315(15) 0.0395(15) 0.0367(13) 0.0048(11) 0.0144(12) 0.0012(12)
O4 0.0377(14) 0.0300(14) 0.0271(12) -0.0012(10) 0.0138(11) -0.0028(11)
O5 0.0490(16) 0.0293(14) 0.0344(13) 0.0016(11) 0.0182(12) -0.0023(12)
C1 0.034(2) 0.031(2) 0.0243(17) -0.0010(15) 0.0117(16) 0.0017(16)
C2 0.039(2) 0.027(2) 0.039(2) 0.0010(17) 0.0208(19) 0.0033(17)
C3 0.038(2) 0.030(2) 0.041(2) -0.0078(17) 0.0150(18) -0.0026(17)
C4 0.036(2) 0.040(2) 0.0331(19) -0.0072(17) 0.0103(18) -0.0009(19)
C5 0.034(2) 0.040(2) 0.0296(18) 0.0034(17) 0.0103(17) 0.0021(18)
C6 0.033(2) 0.027(2) 0.0363(19) -0.0016(15) 0.0133(17) -0.0013(16)
C7 0.040(2) 0.028(2) 0.0286(19) -0.0044(16) 0.0143(18) -0.0030(18)
C8 0.036(2) 0.053(3) 0.043(2) -0.0052(18) 0.0180(19) -0.007(2)
C9 0.035(3) 0.101(4) 0.055(2) 0.008(2) 0.012(2) -0.007(2)
C10 0.027(2) 0.030(2) 0.034(2) -0.0005(17) 0.0103(16) -0.0003(17)
C11 0.052(3) 0.044(2) 0.0289(19) -0.0047(17) 0.0133(19) -0.010(2)
C12 0.089(4) 0.048(3) 0.045(2) -0.006(2) 0.026(2) 0.010(2)
C13 0.042(2) 0.052(3) 0.0311(19) 0.0018(18) 0.0180(18) -0.004(2)
C14 0.056(3) 0.048(3) 0.067(3) 0.024(2) 0.011(2) -0.004(2)
F1A 0.0536(14) 0.0274(11) 0.0405(11) -0.0027(9) 0.0160(10) 0.0007(10)
F2A 0.0462(13) 0.0346(12) 0.0476(12) 0.0077(9) 0.0222(11) -0.0028(10)
N1A 0.0364(18) 0.0332(18) 0.0228(14) 0.0009(13) 0.0087(13) -0.0005(14)
O1A 0.0304(14) 0.0356(15) 0.0408(13) 0.0042(11) 0.0141(11) -0.0003(11)
O2A 0.0475(16) 0.0454(16) 0.0358(14) -0.0022(12) 0.0202(12) 0.0034(13)
O3A 0.0322(15) 0.0386(15) 0.0374(13) -0.0024(11) 0.0132(12) -0.0037(12)
O4A 0.0398(15) 0.0274(14) 0.0271(12) -0.0003(10) 0.0136(11) -0.0007(11)
O5A 0.0474(16) 0.0278(14) 0.0332(13) -0.0034(11) 0.0142(12) 0.0028(12)
C1A 0.036(2) 0.025(2) 0.0267(17) 0.0027(15) 0.0136(16) 0.0000(17)
C2A 0.041(2) 0.028(2) 0.0319(19) -0.0008(16) 0.0175(18) -0.0045(17)
C3A 0.040(2) 0.028(2) 0.038(2) 0.0077(16) 0.0143(18) 0.0032(17)
C4A 0.032(2) 0.043(2) 0.0275(18) 0.0093(17) 0.0066(16) -0.0023(19)
C5A 0.037(2) 0.032(2) 0.0298(18) 0.0002(16) 0.0057(17) -0.0024(17)
C6A 0.036(2) 0.023(2) 0.0352(19) 0.0022(15) 0.0138(17) 0.0005(16)
C7A 0.038(2) 0.026(2) 0.0297(19) 0.0041(16) 0.0137(18) -0.0007(17)
C8A 0.036(2) 0.049(3) 0.048(2) 0.0093(19) 0.019(2) 0.0030(19)
C9A 0.033(3) 0.096(4) 0.055(2) 0.013(3) 0.011(2) -0.002(2)
C10A 0.031(2) 0.026(2) 0.035(2) 0.0035(17) 0.0123(17) -0.0023(16)
C11A 0.048(2) 0.035(2) 0.0308(19) 0.0053(16) 0.0109(18) 0.0000(18)
C12A 0.072(3) 0.043(3) 0.055(2) 0.015(2) 0.032(2) 0.001(2)
C13A 0.042(2) 0.050(3) 0.0306(19) -0.0033(17) 0.0152(18) 0.000(2)
C14A 0.048(3) 0.047(3) 0.052(2) -0.0117(19) 0.019(2) -0.008(2)

_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 C2 1.356(3) . ?
F2 C2 1.373(3) . ?
N1 C10 1.329(4) . ?
N1 C11 1.466(4) . ?
N1 C13 1.468(4) . ?
O1 C3 1.436(4) . ?
O1 C6 1.449(4) . ?
O2 C7 1.203(4) . ?
O3 C7 1.325(4) . ?
O3 C8 1.451(4) . ?
O4 C10 1.377(4) . ?
O4 C1 1.427(3) . ?
O5 C10 1.218(4) . ?
C1 C7 1.525(4) . ?
C1 C6 1.550(4) . ?
C1 C2 1.567(4) . ?
C2 C3 1.525(5) . ?
C3 C4 1.500(4) . ?
C4 C5 1.321(5) . ?
C5 C6 1.520(4) . ?
C8 C9 1.492(5) . ?
C11 C12 1.505(5) . ?
C13 C14 1.513(5) . ?
F1A C2A 1.348(3) . ?
F2A C2A 1.364(3) . ?
N1A C10A 1.330(4) . ?
N1A C11A 1.464(4) . ?
N1A C13A 1.468(4) . ?
O1A C3A 1.436(4) . ?
O1A C6A 1.441(4) . ?
O2A C7A 1.204(3) . ?
O3A C7A 1.334(4) . ?
O3A C8A 1.451(4) . ?
O4A C10A 1.385(4) . ?
O4A C1A 1.427(3) . ?
O5A C10A 1.216(4) . ?
C1A C7A 1.517(4) . ?
C1A C6A 1.548(4) . ?
C1A C2A 1.567(4) . ?
C2A C3A 1.549(5) . ?
C3A C4A 1.519(4) . ?
C4A C5A 1.309(5) . ?
C5A C6A 1.506(4) . ?
C8A C9A 1.497(5) . ?
C11A C12A 1.511(5) . ?
C13A C14A 1.515(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
C10 N1 C11 117.5(3) . . ?
C10 N1 C13 123.9(3) . . ?
C11 N1 C13 118.6(2) . . ?
C3 O1 C6 96.1(2) . . ?
C7 O3 C8 116.7(3) . . ?
C10 O4 C1 114.7(2) . . ?
O4 C1 C7 111.4(3) . . ?
O4 C1 C6 110.6(2) . . ?
C7 C1 C6 116.3(3) . . ?
O4 C1 C2 106.0(2) . . ?
C7 C1 C2 112.8(3) . . ?
C6 C1 C2 98.5(3) . . ?
F1 C2 F2 105.2(3) . . ?
F1 C2 C3 112.3(3) . . ?
F2 C2 C3 112.5(3) . . ?
F1 C2 C1 112.0(2) . . ?
F2 C2 C1 111.8(3) . . ?
C3 C2 C1 103.2(3) . . ?
O1 C3 C4 102.9(3) . . ?
O1 C3 C2 99.4(2) . . ?
C4 C3 C2 106.6(3) . . ?
C5 C4 C3 105.7(3) . . ?
C4 C5 C6 106.0(3) . . ?
O1 C6 C5 101.7(3) . . ?
O1 C6 C1 99.8(2) . . ?
C5 C6 C1 108.3(3) . . ?
O2 C7 O3 125.8(3) . . ?
O2 C7 C1 124.0(3) . . ?
O3 C7 C1 110.1(3) . . ?
O3 C8 C9 107.7(3) . . ?
O5 C10 N1 126.5(3) . . ?
O5 C10 O4 121.7(3) . . ?
N1 C10 O4 111.8(3) . . ?
N1 C11 C12 113.0(3) . . ?
N1 C13 C14 111.9(3) . . ?
C10A N1A C11A 118.4(3) . . ?
C10A N1A C13A 123.1(3) . . ?
C11A N1A C13A 118.3(2) . . ?
C3A O1A C6A 96.8(2) . . ?
C7A O3A C8A 116.9(2) . . ?
C10A O4A C1A 115.2(2) . . ?
O4A C1A C7A 111.9(3) . . ?
O4A C1A C6A 111.3(2) . . ?
C7A C1A C6A 116.7(3) . . ?
O4A C1A C2A 105.3(2) . . ?
C7A C1A C2A 111.4(3) . . ?
C6A C1A C2A 98.9(3) . . ?
F1A C2A F2A 105.8(3) . . ?
F1A C2A C3A 111.6(3) . . ?
F2A C2A C3A 111.8(2) . . ?
F1A C2A C1A 112.7(2) . . ?
F2A C2A C1A 112.3(3) . . ?
C3A C2A C1A 102.8(3) . . ?
O1A C3A C4A 102.1(3) . . ?
O1A C3A C2A 98.9(2) . . ?
C4A C3A C2A 105.7(3) . . ?
C5A C4A C3A 105.4(3) . . ?
C4A C5A C6A 106.9(3) . . ?
O1A C6A C5A 101.6(3) . . ?
O1A C6A C1A 99.9(2) . . ?
C5A C6A C1A 108.8(3) . . ?
O2A C7A O3A 125.5(3) . . ?
O2A C7A C1A 124.9(3) . . ?
O3A C7A C1A 109.5(3) . . ?
O3A C8A C9A 107.0(3) . . ?
O5A C10A N1A 127.6(3) . . ?
O5A C10A O4A 121.5(3) . . ?
N1A C10A O4A 110.8(3) . . ?
N1A C11A C12A 112.0(3) . . ?
N1A C13A C14A 112.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.95
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.065
#===END

data_13b
_database_code_depnum_ccdc_archive 'CCDC 224032'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H21 F2 N O5'
_chemical_formula_weight         333.33

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   6.951(4)
_cell_length_b                   8.869(5)
_cell_length_c                   13.399(7)
_cell_angle_alpha                98.346(10)
_cell_angle_beta                 96.497(9)
_cell_angle_gamma                91.913(10)
_cell_volume                     811.0(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    533
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      18.47
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.116
_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      150(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5929
_diffrn_reflns_av_R_equivalents  0.1077
_diffrn_reflns_av_sigmaI/netI    0.1633
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2833
_reflns_number_gt                1140
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0598P)^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_number_reflns         2833
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1780
_refine_ls_R_factor_gt           0.0718
_refine_ls_wR_factor_ref         0.1912
_refine_ls_wR_factor_gt          0.1506
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_restrained_S_all      0.887
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4924(4) 0.7849(3) 0.9204(2) 0.0670(9) Uani 1 1 d . C .
F2 F 0.4071(4) 0.9717(3) 0.8438(2) 0.0650(9) Uani 1 1 d . C .
N1 N 0.4590(7) 0.4202(5) 0.7724(4) 0.0768(16) Uani 1 1 d . . .
O1 O 0.8137(5) 1.0081(4) 0.8204(3) 0.0565(10) Uani 1 1 d . C .
O2 O 0.4676(5) 0.9526(5) 0.6514(3) 0.0739(12) Uani 1 1 d . C .
O3 O 0.5202(6) 0.7123(4) 0.5900(3) 0.0773(13) Uani 1 1 d . B .
O4 O 0.6209(5) 0.6333(4) 0.7627(2) 0.0481(9) Uani 1 1 d . . .
O5 O 0.2955(5) 0.6274(4) 0.7417(3) 0.0760(13) Uani 1 1 d . . .
C1 C 0.8393(8) 0.8571(6) 0.7754(4) 0.0552(15) Uani 1 1 d . . .
C2 C 0.6207(7) 0.7918(6) 0.7605(4) 0.0452(13) Uani 1 1 d . C .
C3 C 0.5574(8) 0.8830(6) 0.8601(4) 0.0498(14) Uani 1 1 d . . .
C4 C 0.7356(8) 0.9732(6) 0.9079(4) 0.0593(15) Uani 1 1 d . C .
H4 H 0.7152 1.0631 0.9593 0.071 Uiso 1 1 calc R . .
C5 C 0.8738(8) 0.8605(6) 0.9451(4) 0.0628(16) Uani 1 1 d . . .
H5 H 0.9083 0.8448 1.0133 0.075 Uiso 1 1 calc R C .
C6 C 0.9359(8) 0.7891(6) 0.8641(4) 0.0572(15) Uani 1 1 d . C .
H6 H 1.0246 0.7098 0.8612 0.069 Uiso 1 1 calc R . .
C7 C 0.9366(8) 0.8469(6) 0.6825(4) 0.0759(18) Uani 1 1 d . C .
H7A H 0.8623 0.8996 0.6326 0.114 Uiso 1 1 calc R . .
H7B H 0.9445 0.7394 0.6539 0.114 Uiso 1 1 calc R . .
H7C H 1.0676 0.8948 0.6993 0.114 Uiso 1 1 calc R . .
C8 C 0.5194(7) 0.8290(7) 0.6628(4) 0.0534(14) Uani 1 1 d . . .
C9 C 0.4418(13) 0.7351(10) 0.4878(5) 0.126(3) Uani 1 1 d . . .
H9A H 0.5008 0.8306 0.4720 0.151 Uiso 1 1 calc R A 1
H9B H 0.4769 0.6497 0.4381 0.151 Uiso 1 1 calc R A 1
C10 C 0.247(3) 0.7431(19) 0.4782(17) 0.089(6) Uani 0.50 1 d P B 1
H10A H 0.1873 0.6464 0.4898 0.133 Uiso 0.50 1 d PR B 1
H10B H 0.2008 0.7625 0.4096 0.133 Uiso 0.50 1 d PR B 1
H10C H 0.2112 0.8262 0.5282 0.133 Uiso 0.50 1 d PR B 1
C10' C 0.230(3) 0.627(2) 0.4713(16) 0.134(10) Uani 0.50 1 d P B 2
H10D H 0.1401 0.6762 0.5156 0.201 Uiso 0.50 1 d PR B 2
H10E H 0.2560 0.5257 0.4886 0.201 Uiso 0.50 1 d PR B 2
H10F H 0.1726 0.6179 0.4003 0.201 Uiso 0.50 1 d PR B 2
C11 C 0.4424(9) 0.5620(6) 0.7575(4) 0.0592(15) Uani 1 1 d . C .
C12 C 0.6411(8) 0.3531(6) 0.7997(4) 0.0648(17) Uani 1 1 d . C .
H12A H 0.7397 0.3881 0.7592 0.078 Uiso 1 1 calc R . .
H12B H 0.6241 0.2407 0.7828 0.078 Uiso 1 1 calc R . .
C13 C 0.7122(9) 0.3946(7) 0.9101(5) 0.083(2) Uani 1 1 d . . .
H13A H 0.7385 0.5053 0.9263 0.125 Uiso 1 1 calc R C .
H13B H 0.8316 0.3426 0.9260 0.125 Uiso 1 1 calc R . .
H13C H 0.6133 0.3632 0.9506 0.125 Uiso 1 1 calc R . .
C14 C 0.279(4) 0.340(3) 0.795(2) 0.076(6) Uani 0.50 1 d P C 1
H14A H 0.3153 0.2737 0.8466 0.091 Uiso 0.50 1 calc PR C 1
H14B H 0.1930 0.4170 0.8239 0.091 Uiso 0.50 1 calc PR C 1
C15 C 0.175(2) 0.2501(16) 0.7088(15) 0.095(7) Uani 0.50 1 d P C 1
H15A H 0.1620 0.3082 0.6518 0.142 Uiso 0.50 1 d PR C 1
H15B H 0.0459 0.2217 0.7251 0.142 Uiso 0.50 1 d PR C 1
H15C H 0.2442 0.1576 0.6902 0.142 Uiso 0.50 1 d PR C 1
C14' C 0.283(3) 0.312(2) 0.7306(14) 0.078(6) Uani 0.50 1 d P C 2
H14C H 0.1959 0.3517 0.6781 0.093 Uiso 0.50 1 calc PR C 2
H14D H 0.3204 0.2078 0.7043 0.093 Uiso 0.50 1 calc PR C 2
C15' C 0.203(4) 0.318(3) 0.827(2) 0.089(7) Uani 0.50 1 d P C 2
H15D H 0.3002 0.2883 0.8782 0.134 Uiso 0.50 1 d PR C 2
H15E H 0.0885 0.2484 0.8177 0.134 Uiso 0.50 1 d PR C 2
H15F H 0.1666 0.4226 0.8489 0.134 Uiso 0.50 1 d PR C 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 0.071(2) 0.066(2) 0.071(2) 0.0221(17) 0.0243(17) 0.0119(17)
F2 0.058(2) 0.065(2) 0.076(2) 0.0133(17) 0.0135(16) 0.0262(16)
N1 0.046(3) 0.042(3) 0.144(5) 0.028(3) -0.001(3) 0.003(3)
O1 0.053(2) 0.045(2) 0.075(3) 0.0155(19) 0.011(2) 0.0071(18)
O2 0.082(3) 0.085(3) 0.062(3) 0.032(2) 0.008(2) 0.038(2)
O3 0.104(3) 0.079(3) 0.046(2) 0.008(2) -0.003(2) 0.025(3)
O4 0.042(2) 0.044(2) 0.059(2) 0.0115(17) 0.0022(17) 0.0060(17)
O5 0.046(2) 0.058(3) 0.128(4) 0.031(2) 0.004(2) 0.018(2)
C1 0.055(4) 0.051(4) 0.061(4) 0.012(3) 0.004(3) 0.016(3)
C2 0.042(3) 0.047(3) 0.049(3) 0.016(3) -0.001(3) 0.008(3)
C3 0.052(4) 0.042(3) 0.063(4) 0.023(3) 0.016(3) 0.016(3)
C4 0.059(4) 0.057(4) 0.062(4) 0.006(3) 0.007(3) 0.006(3)
C5 0.065(4) 0.064(4) 0.059(4) 0.013(3) -0.004(3) 0.021(3)
C6 0.054(4) 0.048(3) 0.067(4) 0.012(3) -0.012(3) 0.006(3)
C7 0.065(4) 0.086(5) 0.089(5) 0.030(4) 0.035(4) 0.028(3)
C8 0.047(3) 0.060(4) 0.056(4) 0.015(3) 0.006(3) 0.011(3)
C9 0.154(8) 0.173(9) 0.050(5) 0.019(5) -0.010(5) 0.063(7)
C10 0.065(11) 0.124(16) 0.071(11) -0.005(12) -0.001(8) 0.014(13)
C10' 0.080(13) 0.24(3) 0.055(10) -0.027(19) -0.034(8) 0.03(2)
C11 0.053(4) 0.044(4) 0.079(4) 0.008(3) 0.002(3) 0.007(3)
C12 0.060(4) 0.048(4) 0.090(5) 0.017(3) 0.008(3) 0.021(3)
C13 0.093(5) 0.079(5) 0.087(5) 0.038(4) 0.016(4) 0.018(4)
C14 0.080(18) 0.058(12) 0.10(2) 0.033(14) 0.028(17) 0.028(13)
C15 0.047(10) 0.054(10) 0.17(2) -0.001(10) -0.032(10) 0.004(7)
C14' 0.095(15) 0.083(13) 0.046(10) -0.014(10) -0.002(13) 0.001(10)
C15' 0.10(2) 0.084(14) 0.094(18) 0.037(12) 0.026(13) 0.032(14)

_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 C3 1.369(5) . ?
F2 C3 1.346(5) . ?
N1 C11 1.309(6) . ?
N1 C12 1.449(6) . ?
N1 C14 1.50(2) . ?
N1 C14' 1.53(2) . ?
O1 C1 1.412(5) . ?
O1 C4 1.416(6) . ?
O2 C8 1.190(6) . ?
O3 C8 1.315(6) . ?
O3 C9 1.460(6) . ?
O4 C11 1.364(6) . ?
O4 C2 1.410(5) . ?
O5 C11 1.204(6) . ?
C1 C7 1.475(7) . ?
C1 C6 1.511(7) . ?
C1 C2 1.588(7) . ?
C2 C8 1.500(7) . ?
C2 C3 1.572(7) . ?
C3 C4 1.480(7) . ?
C4 C5 1.507(7) . ?
C5 C6 1.300(7) . ?
C9 C10 1.35(2) . ?
C9 C10' 1.70(2) . ?
C12 C13 1.494(7) . ?
C14 C15 1.41(4) . ?
C14' C15' 1.45(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
C11 N1 C12 124.5(5) . . ?
C11 N1 C14 116.0(10) . . ?
C12 N1 C14 116.6(10) . . ?
C11 N1 C14' 115.8(9) . . ?
C12 N1 C14' 117.6(8) . . ?
C14 N1 C14' 33.1(11) . . ?
C1 O1 C4 97.8(4) . . ?
C8 O3 C9 116.8(5) . . ?
C11 O4 C2 115.2(4) . . ?
O1 C1 C7 113.9(5) . . ?
O1 C1 C6 102.0(4) . . ?
C7 C1 C6 117.9(5) . . ?
O1 C1 C2 99.6(4) . . ?
C7 C1 C2 115.9(4) . . ?
C6 C1 C2 105.1(4) . . ?
O4 C2 C8 112.3(4) . . ?
O4 C2 C3 112.5(4) . . ?
C8 C2 C3 115.5(4) . . ?
O4 C2 C1 108.2(4) . . ?
C8 C2 C1 109.6(4) . . ?
C3 C2 C1 97.4(4) . . ?
F2 C3 F1 103.9(4) . . ?
F2 C3 C4 112.1(4) . . ?
F1 C3 C4 112.7(4) . . ?
F2 C3 C2 114.1(4) . . ?
F1 C3 C2 110.5(4) . . ?
C4 C3 C2 103.7(4) . . ?
O1 C4 C3 100.3(4) . . ?
O1 C4 C5 102.4(4) . . ?
C3 C4 C5 106.2(4) . . ?
C6 C5 C4 105.5(5) . . ?
C5 C6 C1 106.5(5) . . ?
O2 C8 O3 125.5(5) . . ?
O2 C8 C2 123.9(5) . . ?
O3 C8 C2 110.1(5) . . ?
C10 C9 O3 112.0(11) . . ?
C10 C9 C10' 36.8(10) . . ?
O3 C9 C10' 101.1(9) . . ?
O5 C11 N1 127.7(6) . . ?
O5 C11 O4 121.9(5) . . ?
N1 C11 O4 110.4(5) . . ?
N1 C12 C13 112.2(5) . . ?
C15 C14 N1 114(2) . . ?
C15' C14' N1 95.5(19) . . ?
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.050
#===END

data_14b
_database_code_depnum_ccdc_archive 'CCDC 224033'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H23 F2 N O5'
_chemical_formula_sum            'C16 H23 F2 N O5'
_chemical_formula_weight         347.35
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'
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   7.8012(5)
_cell_length_b                   8.9989(5)
_cell_length_c                   14.1190(9)
_cell_angle_alpha                96.881(3)
_cell_angle_beta                 102.152(3)
_cell_angle_gamma                108.900(3)
_cell_volume                     897.60(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1709
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      55.17
_exptl_crystal_description       plate
_exptl_crystal_colour            clear
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6554
_exptl_absorpt_correction_T_max  0.9134
_exptl_absorpt_process_details   'SADABS in SAINTPLUS'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4530
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         55.17
_reflns_number_total             2041
_reflns_number_gt                1709
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       SMART
_computing_cell_refinement       SAINTPLUS
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    SHELXTL
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0992P)^2^+0.3578P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0052(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2041
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1693
_refine_ls_wR_factor_gt          0.1632
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
C1 C 0.2485(4) 0.8299(3) 0.7076(2) 0.0548(8) Uani 1 1 d . . .
C2 C 0.0435(5) 0.7912(4) 0.6432(3) 0.0662(10) Uani 1 1 d . . .
C3 C 0.0724(5) 0.8409(4) 0.5475(3) 0.0719(10) Uani 1 1 d . . .
H3 H -0.0355 0.8548 0.5048 0.086 Uiso 1 1 calc R . .
C4 C 0.1524(5) 0.7339(4) 0.4990(3) 0.0756(10) Uani 1 1 d . . .
H4 H 0.0905 0.6536 0.4425 0.091 Uiso 1 1 calc R . .
C5 C 0.3288(5) 0.7741(4) 0.5513(2) 0.0670(10) Uani 1 1 d . . .
C6 C 0.3595(5) 0.9102(4) 0.6349(2) 0.0621(9) Uani 1 1 d . . .
C7 C 0.4216(5) 0.6825(4) 0.7841(2) 0.0617(9) Uani 1 1 d . . .
C8 C 0.2672(5) 0.3898(4) 0.7302(3) 0.0834(12) Uani 1 1 d . . .
H8A H 0.3173 0.3053 0.7199 0.100 Uiso 1 1 calc R . .
H8B H 0.2188 0.4101 0.6659 0.100 Uiso 1 1 calc R . .
C9 C 0.1109(7) 0.3334(6) 0.7762(5) 0.1236(18) Uani 1 1 d . . .
H9A H 0.1590 0.3208 0.8420 0.185 Uiso 1 1 calc R . .
H9B H 0.0218 0.2323 0.7375 0.185 Uiso 1 1 calc R . .
H9C H 0.0503 0.4106 0.7792 0.185 Uiso 1 1 calc R . .
C10 C 0.5757(6) 0.5177(5) 0.8596(4) 0.0992(14) Uani 1 1 d . . .
H10A H 0.6262 0.6072 0.9156 0.119 Uiso 1 1 calc R . .
H10B H 0.5308 0.4196 0.8838 0.119 Uiso 1 1 calc R . .
C11 C 0.7182(8) 0.5133(7) 0.8134(5) 0.1361(19) Uani 1 1 d . . .
H11A H 0.6667 0.4271 0.7564 0.204 Uiso 1 1 calc R . .
H11B H 0.8169 0.4965 0.8591 0.204 Uiso 1 1 calc R . .
H11C H 0.7679 0.6131 0.7932 0.204 Uiso 1 1 calc R . .
C12 C 0.2771(5) 0.9352(4) 0.8058(3) 0.0647(9) Uani 1 1 d . . .
C13 C 0.2179(7) 0.9353(6) 0.9640(3) 0.1040(14) Uani 1 1 d . . .
H13A H 0.3452 1.0097 0.9947 0.125 Uiso 1 1 calc R . .
H13B H 0.1356 0.9964 0.9556 0.125 Uiso 1 1 calc R . .
C14 C 0.1621(9) 0.8241(7) 1.0258(4) 0.142(2) Uani 1 1 d . . .
H14A H 0.0333 0.7553 0.9972 0.214 Uiso 1 1 calc R . .
H14B H 0.1752 0.8817 1.0902 0.214 Uiso 1 1 calc R . .
H14C H 0.2402 0.7606 1.0313 0.214 Uiso 1 1 calc R . .
C15 C 0.4699(6) 0.7005(5) 0.5384(3) 0.0931(12) Uani 1 1 d . . .
H15A H 0.4139 0.6103 0.4839 0.140 Uiso 1 1 calc R . .
H15B H 0.5115 0.6653 0.5977 0.140 Uiso 1 1 calc R . .
H15C H 0.5753 0.7783 0.5254 0.140 Uiso 1 1 calc R . .
C16 C 0.5570(5) 1.0303(4) 0.6758(3) 0.0801(11) Uani 1 1 d . . .
H16A H 0.6044 1.0693 0.6225 0.120 Uiso 1 1 calc R . .
H16B H 0.6358 0.9797 0.7095 0.120 Uiso 1 1 calc R . .
H16C H 0.5567 1.1183 0.7213 0.120 Uiso 1 1 calc R . .
N1 N 0.4193(4) 0.5349(3) 0.7891(2) 0.0749(9) Uani 1 1 d . . .
O1 O 0.2356(3) 0.9870(3) 0.59069(18) 0.0755(7) Uani 1 1 d . . .
O2 O 0.2633(3) 0.6781(2) 0.71935(15) 0.0587(6) Uani 1 1 d . . .
O3 O 0.5456(3) 0.8073(3) 0.82990(17) 0.0768(8) Uani 1 1 d . . .
O4 O 0.3453(4) 1.0795(3) 0.82381(18) 0.0830(8) Uani 1 1 d . . .
O5 O 0.2084(3) 0.8486(3) 0.86819(17) 0.0756(7) Uani 1 1 d . . .
F1 F -0.0695(3) 0.6349(2) 0.62938(16) 0.0824(7) Uani 1 1 d . . .
F2 F -0.0430(3) 0.8763(3) 0.68722(17) 0.0906(7) Uani 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 0.0614(19) 0.0416(17) 0.064(2) 0.0141(15) 0.0102(15) 0.0250(15)
C2 0.057(2) 0.048(2) 0.094(3) 0.0141(18) 0.0114(17) 0.0242(17)
C3 0.065(2) 0.059(2) 0.081(3) 0.0178(18) -0.0070(18) 0.0236(19)
C4 0.086(3) 0.069(2) 0.063(2) 0.0121(18) 0.0015(19) 0.027(2)
C5 0.075(2) 0.069(2) 0.058(2) 0.0195(17) 0.0117(17) 0.0300(19)
C6 0.068(2) 0.0494(19) 0.067(2) 0.0182(16) 0.0088(16) 0.0234(17)
C7 0.063(2) 0.053(2) 0.065(2) 0.0103(17) 0.0052(17) 0.0235(18)
C8 0.079(3) 0.052(2) 0.106(3) 0.013(2) -0.007(2) 0.028(2)
C9 0.090(3) 0.092(3) 0.186(5) 0.049(3) 0.029(3) 0.027(3)
C10 0.079(3) 0.071(3) 0.142(4) 0.026(3) 0.009(3) 0.033(2)
C11 0.102(4) 0.132(5) 0.167(5) 0.035(4) 0.018(4) 0.041(3)
C12 0.071(2) 0.055(2) 0.072(2) 0.0177(19) 0.0144(17) 0.0279(18)
C13 0.129(4) 0.112(4) 0.075(3) 0.010(3) 0.037(3) 0.045(3)
C14 0.160(5) 0.152(5) 0.084(3) 0.020(3) 0.043(3) 0.011(4)
C15 0.093(3) 0.105(3) 0.089(3) 0.015(2) 0.023(2) 0.049(3)
C16 0.067(2) 0.069(2) 0.089(3) 0.0195(19) 0.0136(19) 0.0087(19)
N1 0.076(2) 0.0534(17) 0.089(2) 0.0201(15) -0.0069(16) 0.0316(15)
O1 0.0801(16) 0.0563(14) 0.0906(17) 0.0297(12) 0.0066(13) 0.0300(13)
O2 0.0633(14) 0.0450(12) 0.0646(14) 0.0122(9) 0.0025(10) 0.0240(10)
O3 0.0736(15) 0.0585(15) 0.0812(17) 0.0068(12) -0.0075(12) 0.0216(13)
O4 0.108(2) 0.0496(16) 0.0874(18) 0.0080(12) 0.0175(14) 0.0304(14)
O5 0.0891(17) 0.0663(15) 0.0698(16) 0.0127(13) 0.0234(13) 0.0249(13)
F1 0.0608(12) 0.0617(13) 0.1081(16) 0.0188(11) 0.0041(10) 0.0114(10)
F2 0.0718(13) 0.0870(15) 0.1199(18) 0.0139(13) 0.0176(12) 0.0449(12)

_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 O2 1.433(3) . ?
C1 C12 1.513(5) . ?
C1 C2 1.567(5) . ?
C1 C6 1.573(5) . ?
C2 F2 1.351(4) . ?
C2 F1 1.361(4) . ?
C2 C3 1.512(5) . ?
C3 O1 1.456(4) . ?
C3 C4 1.482(5) . ?
C4 C5 1.324(5) . ?
C5 C15 1.487(5) . ?
C5 C6 1.515(5) . ?
C6 O1 1.443(4) . ?
C6 C16 1.507(5) . ?
C7 O3 1.214(4) . ?
C7 N1 1.333(4) . ?
C7 O2 1.359(4) . ?
C8 N1 1.458(4) . ?
C8 C9 1.476(6) . ?
C10 C11 1.411(7) . ?
C10 N1 1.467(5) . ?
C12 O4 1.205(4) . ?
C12 O5 1.327(4) . ?
C13 C14 1.428(7) . ?
C13 O5 1.453(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
O2 C1 C12 111.9(2) . . ?
O2 C1 C2 106.0(2) . . ?
C12 C1 C2 108.7(3) . . ?
O2 C1 C6 113.2(2) . . ?
C12 C1 C6 116.8(3) . . ?
C2 C1 C6 98.7(2) . . ?
F2 C2 F1 105.2(3) . . ?
F2 C2 C3 111.2(3) . . ?
F1 C2 C3 112.6(3) . . ?
F2 C2 C1 111.0(3) . . ?
F1 C2 C1 113.6(2) . . ?
C3 C2 C1 103.4(3) . . ?
O1 C3 C4 102.7(3) . . ?
O1 C3 C2 97.4(3) . . ?
C4 C3 C2 108.4(3) . . ?
C5 C4 C3 107.1(3) . . ?
C4 C5 C15 129.6(3) . . ?
C4 C5 C6 105.4(3) . . ?
C15 C5 C6 125.0(3) . . ?
O1 C6 C16 110.4(3) . . ?
O1 C6 C5 102.5(3) . . ?
C16 C6 C5 116.8(3) . . ?
O1 C6 C1 99.6(2) . . ?
C16 C6 C1 119.6(3) . . ?
C5 C6 C1 105.4(3) . . ?
O3 C7 N1 126.3(3) . . ?
O3 C7 O2 122.6(3) . . ?
N1 C7 O2 111.1(3) . . ?
N1 C8 C9 113.5(4) . . ?
C11 C10 N1 110.2(4) . . ?
O4 C12 O5 124.1(3) . . ?
O4 C12 C1 124.5(3) . . ?
O5 C12 C1 111.3(3) . . ?
C14 C13 O5 109.5(4) . . ?
C7 N1 C8 123.5(3) . . ?
C7 N1 C10 118.2(3) . . ?
C8 N1 C10 118.3(3) . . ?
C6 O1 C3 96.5(2) . . ?
C7 O2 C1 116.5(2) . . ?
C12 O5 C13 117.2(3) . . ?
_diffrn_measured_fraction_theta_max 0.897
_diffrn_reflns_theta_full        55.17
_diffrn_measured_fraction_theta_full 0.897
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.044
#===END

data_16
_database_code_depnum_ccdc_archive 'CCDC 224034'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 F2 O6'
_chemical_formula_weight         264.18

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'
O O 0.0106 0.0060 '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'
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3657(7)
_cell_length_b                   7.5078(7)
_cell_length_c                   10.1384(9)
_cell_angle_alpha                77.063(2)
_cell_angle_beta                 78.383(2)
_cell_angle_gamma                89.452(2)
_cell_volume                     534.86(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2369
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      27.85
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      150(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3895
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1866
_reflns_number_gt                1648
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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^)+(0.0470P)^2^+0.0755P] 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_number_reflns         1866
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0871
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002

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 0.09090(11) 0.17923(11) 0.98351(8) 0.0277(2) Uani 1 1 d . . .
F2 F 0.26386(11) 0.02578(10) 0.85090(9) 0.0290(2) Uani 1 1 d . . .
O1 O 0.11514(15) 0.56096(14) 0.59274(11) 0.0319(3) Uani 1 1 d . . .
O2 O 0.30723(17) 0.48871(16) 0.41177(11) 0.0412(3) Uani 1 1 d . . .
O3 O 0.24432(13) 0.29012(13) 0.61748(10) 0.0250(3) Uani 1 1 d . . .
O4 O 0.45017(14) 0.23393(15) 0.98510(10) 0.0310(3) Uani 1 1 d . . .
H4 H 0.5516 0.1852 0.9633 0.046 Uiso 1 1 calc R . .
O5 O -0.20157(14) 0.18321(14) 0.83287(11) 0.0288(3) Uani 1 1 d . . .
O6 O -0.03118(14) 0.04893(14) 0.67447(11) 0.0283(3) Uani 1 1 d . . .
C2 C 0.2295(2) 0.4518(2) 0.52939(16) 0.0289(4) Uani 1 1 d . . .
C3A C 0.11516(19) 0.28125(19) 0.74542(14) 0.0221(3) Uani 1 1 d . . .
C4 C 0.21494(19) 0.19741(18) 0.86202(14) 0.0223(3) Uani 1 1 d . . .
C5 C 0.3826(2) 0.3109(2) 0.86410(14) 0.0250(3) Uani 1 1 d . . .
H5 H 0.4812 0.3087 0.7808 0.030 Uiso 1 1 calc R . .
C6 C 0.3281(2) 0.5035(2) 0.86222(16) 0.0315(4) Uani 1 1 d . . .
H6 H 0.3981 0.5758 0.9014 0.038 Uiso 1 1 calc R . .
C7 C 0.1885(2) 0.5791(2) 0.80938(16) 0.0315(4) Uani 1 1 d . . .
H7 H 0.1614 0.7015 0.8149 0.038 Uiso 1 1 calc R . .
C7A C 0.0708(2) 0.48246(19) 0.74147(15) 0.0259(3) Uani 1 1 d . . .
H7A H -0.0637 0.4943 0.7798 0.031 Uiso 1 1 calc R . .
C8 C -0.0599(2) 0.16515(19) 0.75514(14) 0.0230(3) Uani 1 1 d . . .
C9 C -0.1879(2) -0.0770(2) 0.68335(17) 0.0316(4) Uani 1 1 d . . .
H9A H -0.2535 -0.1168 0.7810 0.038 Uiso 1 1 calc R . .
H9B H -0.1399 -0.1869 0.6513 0.038 Uiso 1 1 calc R . .
C10 C -0.3217(2) 0.0117(2) 0.59758(17) 0.0344(4) Uani 1 1 d . . .
H10A H -0.3742 0.1169 0.6322 0.052 Uiso 1 1 calc R . .
H10B H -0.4216 -0.0767 0.6033 0.052 Uiso 1 1 calc R . .
H10C H -0.2567 0.0529 0.5011 0.052 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
F1 0.0239(5) 0.0348(5) 0.0215(4) -0.0018(4) -0.0026(3) -0.0027(4)
F2 0.0311(5) 0.0218(5) 0.0350(5) -0.0049(4) -0.0106(4) 0.0036(4)
O1 0.0403(6) 0.0250(6) 0.0289(6) 0.0005(4) -0.0108(5) 0.0009(5)
O2 0.0479(7) 0.0450(7) 0.0241(6) 0.0020(5) -0.0024(5) -0.0101(6)
O3 0.0256(6) 0.0260(5) 0.0208(5) -0.0028(4) -0.0015(4) -0.0014(4)
O4 0.0239(6) 0.0423(6) 0.0275(6) -0.0058(5) -0.0094(5) 0.0019(5)
O5 0.0224(6) 0.0342(6) 0.0281(6) -0.0050(5) -0.0034(5) -0.0002(4)
O6 0.0251(6) 0.0288(6) 0.0337(6) -0.0113(5) -0.0073(5) -0.0022(4)
C2 0.0306(8) 0.0290(8) 0.0255(8) -0.0009(6) -0.0079(7) -0.0066(7)
C3A 0.0206(7) 0.0246(7) 0.0202(7) -0.0050(6) -0.0021(6) 0.0009(6)
C4 0.0227(7) 0.0218(7) 0.0207(7) -0.0039(6) -0.0018(6) 0.0011(6)
C5 0.0234(8) 0.0305(8) 0.0213(7) -0.0047(6) -0.0059(6) -0.0016(6)
C6 0.0351(9) 0.0308(8) 0.0309(9) -0.0096(7) -0.0087(7) -0.0063(7)
C7 0.0396(9) 0.0231(8) 0.0337(9) -0.0089(6) -0.0090(7) 0.0006(7)
C7A 0.0277(8) 0.0233(8) 0.0256(8) -0.0027(6) -0.0062(6) 0.0008(6)
C8 0.0248(8) 0.0218(7) 0.0220(7) -0.0005(6) -0.0082(6) 0.0016(6)
C9 0.0315(9) 0.0275(8) 0.0381(9) -0.0077(7) -0.0118(7) -0.0059(7)
C10 0.0293(9) 0.0399(9) 0.0381(9) -0.0135(7) -0.0111(7) 0.0006(7)

_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 C4 1.3581(16) . ?
F2 C4 1.3575(16) . ?
O1 C2 1.3413(19) . ?
O1 C7A 1.4613(18) . ?
O2 C2 1.1860(18) . ?
O3 C2 1.3541(18) . ?
O3 C3A 1.4344(16) . ?
O4 C5 1.4175(17) . ?
O5 C8 1.2007(17) . ?
O6 C8 1.3120(17) . ?
O6 C9 1.4750(17) . ?
C3A C4 1.5302(19) . ?
C3A C7A 1.536(2) . ?
C3A C8 1.538(2) . ?
C4 C5 1.5132(19) . ?
C5 C6 1.494(2) . ?
C6 C7 1.319(2) . ?
C7 C7A 1.492(2) . ?
C9 C10 1.498(2) . ?

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 C7A 109.57(11) . . ?
C2 O3 C3A 109.18(11) . . ?
C8 O6 C9 116.51(12) . . ?
O2 C2 O1 125.38(14) . . ?
O2 C2 O3 123.63(15) . . ?
O1 C2 O3 110.99(12) . . ?
O3 C3A C4 107.13(11) . . ?
O3 C3A C7A 103.29(11) . . ?
C4 C3A C7A 112.62(11) . . ?
O3 C3A C8 111.58(11) . . ?
C4 C3A C8 110.34(11) . . ?
C7A C3A C8 111.62(12) . . ?
F2 C4 F1 106.49(10) . . ?
F2 C4 C5 110.56(11) . . ?
F1 C4 C5 109.64(11) . . ?
F2 C4 C3A 108.98(11) . . ?
F1 C4 C3A 107.65(11) . . ?
C5 C4 C3A 113.26(11) . . ?
O4 C5 C6 110.76(12) . . ?
O4 C5 C4 108.60(11) . . ?
C6 C5 C4 109.26(12) . . ?
C7 C6 C5 123.87(14) . . ?
C6 C7 C7A 123.50(14) . . ?
O1 C7A C7 108.52(12) . . ?
O1 C7A C3A 101.00(11) . . ?
C7 C7A C3A 115.01(13) . . ?
O5 C8 O6 127.00(13) . . ?
O5 C8 C3A 120.45(13) . . ?
O6 C8 C3A 112.52(12) . . ?
O6 C9 C10 111.59(12) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.041
#===END

data_22a
_database_code_depnum_ccdc_archive 'CCDC 224035'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H14 F2 O3'
_chemical_formula_sum            'C11 H14 F2 O3'
_chemical_formula_weight         232.22
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'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
_cell_length_a                   9.7681(13)
_cell_length_b                   11.8090(15)
_cell_length_c                   10.5162(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.677(9)
_cell_angle_gamma                90.00
_cell_volume                     1102.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2308
_cell_measurement_theta_min      5.42
_cell_measurement_theta_max      28.7
_exptl_crystal_description       Block
_exptl_crystal_colour            Clear
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  0.9529
_exptl_absorpt_correction_T_max  0.9529
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-axis IIc image plate'
_diffrn_measurement_method       'Image plate slices'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4540
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.42
_diffrn_reflns_theta_max         28.70
_reflns_number_total             2373
_reflns_number_gt                2308
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'MSC software'
_computing_cell_refinement       'MSC software'
_computing_data_reduction        'MSC software'
_computing_structure_solution    SHELXS86
_computing_structure_refinement  SHELXL97
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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^)+(0.1330P)^2^+1.0035P] 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   -1.4(11)
_refine_ls_number_reflns         2373
_refine_ls_number_parameters     148
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.2013
_refine_ls_wR_factor_gt          0.1948
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.7240(3) 0.18096(17) 0.6339(2) 0.0439(5) Uani 1 1 d . . .
F2 F 0.6669(3) 0.27130(15) 0.7839(2) 0.0449(5) Uani 1 1 d . . .
O1 O 0.4737(3) 0.03675(17) 0.5894(2) 0.0345(5) Uani 1 1 d . . .
O2 O 0.9022(3) 0.09020(18) 0.9971(2) 0.0385(5) Uani 1 1 d . . .
O3 O 0.7965(3) 0.00138(19) 0.7864(2) 0.0336(5) Uani 1 1 d . . .
C1 C 0.6798(3) 0.0637(2) 0.8021(3) 0.0285(5) Uani 1 1 d . . .
C2 C 0.6395(4) 0.1732(2) 0.7088(3) 0.0334(6) Uani 1 1 d . . .
C3 C 0.4713(4) 0.1558(2) 0.6120(3) 0.0364(6) Uani 1 1 d . . .
H3 H 0.4311 0.2034 0.5255 0.044 Uiso 1 1 calc R . .
C4 C 0.3855(4) 0.1637(3) 0.7034(4) 0.0397(7) Uani 1 1 d . . .
H4 H 0.3220 0.2236 0.7063 0.048 Uiso 1 1 calc R . .
C5 C 0.4179(4) 0.0695(3) 0.7782(3) 0.0390(7) Uani 1 1 d . . .
H5 H 0.3820 0.0479 0.8458 0.047 Uiso 1 1 calc R . .
C6 C 0.5252(3) 0.0019(2) 0.7340(3) 0.0315(6) Uani 1 1 d . . .
C7 C 0.7441(4) 0.0839(3) 0.9592(3) 0.0348(6) Uani 1 1 d . . .
H7A H 0.7056 0.1555 0.9811 0.042 Uiso 1 1 calc R . .
H7B H 0.7195 0.0206 1.0077 0.042 Uiso 1 1 calc R . .
C8 C 0.9346(3) 0.0094(2) 0.9126(3) 0.0323(6) Uani 1 1 d . . .
C9 C 1.0598(5) 0.0544(3) 0.8789(5) 0.0498(8) Uani 1 1 d . . .
H9A H 1.0826 -0.0005 0.8205 0.075 Uiso 1 1 calc R . .
H9B H 1.1498 0.0668 0.9659 0.075 Uiso 1 1 calc R . .
H9C H 1.0284 0.1262 0.8282 0.075 Uiso 1 1 calc R . .
C10 C 0.9693(5) -0.1055(3) 0.9838(4) 0.0445(7) Uani 1 1 d . . .
H10A H 0.9790 -0.1618 0.9196 0.067 Uiso 1 1 calc R . .
H10B H 0.8873 -0.1276 1.0093 0.067 Uiso 1 1 calc R . .
H10C H 1.0638 -0.1012 1.0683 0.067 Uiso 1 1 calc R . .
C11 C 0.5279(5) -0.1244(3) 0.7478(4) 0.0458(8) Uani 1 1 d . . .
H11A H 0.4245 -0.1534 0.7076 0.069 Uiso 1 1 calc R . .
H11B H 0.5774 -0.1451 0.8470 0.069 Uiso 1 1 calc R . .
H11C H 0.5836 -0.1572 0.6979 0.069 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
F1 0.0498(12) 0.0433(10) 0.0446(11) 0.0070(8) 0.0256(10) -0.0004(8)
F2 0.0532(12) 0.0258(8) 0.0462(11) -0.0057(7) 0.0113(10) -0.0012(7)
O1 0.0382(11) 0.0347(10) 0.0227(9) -0.0022(7) 0.0049(8) -0.0021(8)
O2 0.0317(11) 0.0405(11) 0.0322(10) -0.0123(8) 0.0025(9) 0.0007(8)
O3 0.0327(11) 0.0363(9) 0.0250(9) -0.0062(7) 0.0053(8) 0.0046(7)
C1 0.0329(14) 0.0264(10) 0.0225(11) -0.0028(8) 0.0079(10) -0.0005(9)
C2 0.0418(16) 0.0282(11) 0.0285(13) -0.0016(9) 0.0128(12) 0.0000(10)
C3 0.0428(16) 0.0330(13) 0.0272(14) 0.0042(9) 0.0085(12) 0.0053(11)
C4 0.0335(16) 0.0479(16) 0.0323(14) -0.0003(11) 0.0083(12) 0.0071(12)
C5 0.0320(15) 0.0518(17) 0.0308(14) 0.0017(12) 0.0108(12) 0.0002(11)
C6 0.0312(14) 0.0337(12) 0.0235(12) 0.0017(9) 0.0053(10) -0.0026(10)
C7 0.0354(15) 0.0402(13) 0.0221(12) -0.0055(9) 0.0054(11) -0.0002(10)
C8 0.0275(13) 0.0349(12) 0.0288(13) -0.0030(10) 0.0062(11) 0.0020(10)
C9 0.0392(18) 0.054(2) 0.056(2) -0.0003(16) 0.0194(17) -0.0020(14)
C10 0.049(2) 0.0414(16) 0.0364(16) 0.0036(12) 0.0108(14) 0.0095(13)
C11 0.049(2) 0.0344(14) 0.0484(18) 0.0018(12) 0.0148(16) -0.0113(12)

_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 C2 1.362(4) . ?
F2 C2 1.364(3) . ?
O1 C3 1.427(4) . ?
O1 C6 1.448(3) . ?
O2 C8 1.426(3) . ?
O2 C7 1.427(4) . ?
O3 C1 1.423(3) . ?
O3 C8 1.447(4) . ?
C1 C7 1.521(4) . ?
C1 C6 1.557(4) . ?
C1 C2 1.571(4) . ?
C2 C3 1.543(5) . ?
C3 C4 1.519(5) . ?
C4 C5 1.322(5) . ?
C5 C6 1.536(5) . ?
C6 C11 1.497(4) . ?
C8 C9 1.505(5) . ?
C8 C10 1.517(4) . ?
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
C3 O1 C6 97.4(2) . . ?
C8 O2 C7 106.7(2) . . ?
C1 O3 C8 110.2(2) . . ?
O3 C1 C7 102.7(2) . . ?
O3 C1 C6 112.0(2) . . ?
C7 C1 C6 117.0(2) . . ?
O3 C1 C2 111.0(2) . . ?
C7 C1 C2 115.5(2) . . ?
C6 C1 C2 99.0(2) . . ?
F1 C2 F2 105.0(2) . . ?
F1 C2 C3 111.3(3) . . ?
F2 C2 C3 113.1(3) . . ?
F1 C2 C1 111.2(2) . . ?
F2 C2 C1 113.6(2) . . ?
C3 C2 C1 102.9(2) . . ?
O1 C3 C4 102.6(2) . . ?
O1 C3 C2 98.9(2) . . ?
C4 C3 C2 106.9(2) . . ?
C5 C4 C3 105.5(3) . . ?
C4 C5 C6 106.4(3) . . ?
O1 C6 C11 111.7(3) . . ?
O1 C6 C5 100.9(2) . . ?
C11 C6 C5 118.4(3) . . ?
O1 C6 C1 101.2(2) . . ?
C11 C6 C1 116.6(3) . . ?
C5 C6 C1 105.7(2) . . ?
O2 C7 C1 102.7(2) . . ?
O2 C8 O3 104.5(2) . . ?
O2 C8 C9 108.9(3) . . ?
O3 C8 C9 110.2(3) . . ?
O2 C8 C10 110.7(3) . . ?
O3 C8 C10 108.9(2) . . ?
C9 C8 C10 113.3(3) . . ?
_diffrn_measured_fraction_theta_max 0.934
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_full 0.934
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.060
#===END

data_31
_database_code_depnum_ccdc_archive 'CCDC 224036'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H16 F2 O3'
_chemical_formula_sum            'C11 H16 F2 O3'
_chemical_formula_weight         234.24

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'
O O 0.0106 0.0060 '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'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a                   9.8294(12)
_cell_length_b                   8.3435(13)
_cell_length_c                   13.9113(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.998(10)
_cell_angle_gamma                90.00
_cell_volume                     1126.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1818
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      28.7
_exptl_crystal_description       block
_exptl_crystal_colour            clear
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9537
_exptl_absorpt_correction_T_max  0.9650
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-axis IIc Image plate'
_diffrn_measurement_method       'Image plate slices'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8756
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_av_sigmaI/netI    0.0798
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         28.70
_reflns_number_total             2615
_reflns_number_gt                1818
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'MSC Software'
_computing_cell_refinement       'MSC Software'
_computing_data_reduction        'MSC Software'
_computing_structure_solution    SHELXS86
_computing_structure_refinement  SHELXL97
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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^)+(0.1341P)^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_number_reflns         2615
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.2216
_refine_ls_wR_factor_gt          0.1743
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.68104(16) 0.34485(18) 0.50665(11) 0.0299(4) Uani 1 1 d . . .
O2 O 0.88700(17) 0.43949(19) 0.58690(11) 0.0352(4) Uani 1 1 d . . .
O3 O 0.8272(2) 0.4511(2) 0.36262(12) 0.0369(4) Uani 1 1 d . . .
F1 F 0.70824(17) 0.04677(18) 0.57809(10) 0.0436(4) Uani 1 1 d . . .
F2 F 0.85039(16) -0.02924(16) 0.48284(11) 0.0438(4) Uani 1 1 d . . .
C1 C 0.7858(2) 0.2454(2) 0.47679(14) 0.0282(5) Uani 1 1 d . . .
C2 C 0.7390(3) 0.0718(3) 0.48627(16) 0.0328(5) Uani 1 1 d . . .
C3 C 0.6205(2) 0.0231(3) 0.41178(17) 0.0350(5) Uani 1 1 d . . .
H3 H 0.5720 -0.0727 0.4210 0.042 Uiso 1 1 calc R . .
C4 C 0.5812(2) 0.1109(3) 0.33270(16) 0.0361(5) Uani 1 1 d . . .
H4 H 0.5043 0.0748 0.2879 0.043 Uiso 1 1 calc R . .
C5 C 0.6500(2) 0.2632(3) 0.30942(16) 0.0354(5) Uani 1 1 d . . .
H5A H 0.5916 0.3551 0.3220 0.043 Uiso 1 1 calc R . .
H5B H 0.6575 0.2639 0.2393 0.043 Uiso 1 1 calc R . .
C6 C 0.7951(2) 0.2854(3) 0.36915(15) 0.0304(5) Uani 1 1 d . . .
C7 C 0.9012(3) 0.1839(3) 0.32598(17) 0.0410(6) Uani 1 1 d . . .
H7A H 0.8696 0.0724 0.3196 0.062 Uiso 1 1 calc R . .
H7B H 0.9901 0.1887 0.3690 0.062 Uiso 1 1 calc R . .
H7C H 0.9115 0.2258 0.2617 0.062 Uiso 1 1 calc R . .
C8 C 0.9159(2) 0.2858(3) 0.55032(15) 0.0316(5) Uani 1 1 d . . .
H8A H 0.9310 0.2056 0.6033 0.038 Uiso 1 1 calc R . .
H8B H 0.9985 0.2897 0.5178 0.038 Uiso 1 1 calc R . .
C9 C 0.7394(2) 0.4530(3) 0.58263(15) 0.0318(5) Uani 1 1 d . . .
C10 C 0.6972(3) 0.6220(3) 0.5531(2) 0.0437(6) Uani 1 1 d . . .
H10A H 0.5970 0.6322 0.5474 0.066 Uiso 1 1 calc R . .
H10B H 0.7257 0.6465 0.4902 0.066 Uiso 1 1 calc R . .
H10C H 0.7417 0.6971 0.6024 0.066 Uiso 1 1 calc R . .
C11 C 0.6956(3) 0.4018(4) 0.67754(18) 0.0480(7) Uani 1 1 d . . .
H11A H 0.5949 0.3945 0.6691 0.072 Uiso 1 1 calc R . .
H11B H 0.7278 0.4808 0.7281 0.072 Uiso 1 1 calc R . .
H11C H 0.7358 0.2969 0.6968 0.072 Uiso 1 1 calc R . .
H12 H 0.909(3) 0.464(4) 0.373(2) 0.042(8) 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 0.0353(9) 0.0289(8) 0.0245(7) -0.0046(6) 0.0015(6) 0.0002(6)
O2 0.0350(9) 0.0326(9) 0.0359(9) -0.0099(6) -0.0007(6) -0.0006(6)
O3 0.0467(12) 0.0304(9) 0.0334(9) 0.0054(6) 0.0054(7) -0.0047(7)
F1 0.0597(10) 0.0405(8) 0.0297(7) 0.0092(6) 0.0044(6) -0.0087(7)
F2 0.0448(9) 0.0265(7) 0.0579(9) 0.0033(6) 0.0017(7) 0.0062(6)
C1 0.0357(11) 0.0251(10) 0.0226(9) -0.0003(7) 0.0009(7) 0.0011(8)
C2 0.0431(13) 0.0262(10) 0.0278(10) 0.0027(8) 0.0010(9) 0.0031(9)
C3 0.0365(13) 0.0305(11) 0.0374(12) -0.0070(9) 0.0042(9) -0.0061(9)
C4 0.0324(12) 0.0430(13) 0.0313(11) -0.0090(9) 0.0002(8) -0.0032(9)
C5 0.0428(13) 0.0395(13) 0.0220(10) -0.0001(8) -0.0013(8) 0.0019(9)
C6 0.0401(12) 0.0272(10) 0.0233(10) 0.0003(7) 0.0024(8) 0.0004(8)
C7 0.0539(15) 0.0390(13) 0.0312(12) -0.0051(9) 0.0099(10) -0.0013(11)
C8 0.0383(12) 0.0278(11) 0.0269(10) -0.0034(8) -0.0009(8) 0.0005(8)
C9 0.0367(12) 0.0305(11) 0.0275(10) -0.0067(8) 0.0026(8) -0.0054(8)
C10 0.0467(15) 0.0331(13) 0.0513(15) -0.0083(11) 0.0074(11) 0.0027(10)
C11 0.0625(18) 0.0538(17) 0.0282(12) -0.0066(10) 0.0090(11) -0.0059(13)

_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 1.433(3) . ?
O1 C9 1.439(2) . ?
O2 C8 1.425(3) . ?
O2 C9 1.447(3) . ?
O3 C6 1.424(3) . ?
F1 C2 1.374(3) . ?
F2 C2 1.389(3) . ?
C1 C2 1.532(3) . ?
C1 C8 1.545(3) . ?
C1 C6 1.551(3) . ?
C2 C3 1.489(3) . ?
C3 C4 1.328(3) . ?
C4 C5 1.498(3) . ?
C5 C6 1.545(3) . ?
C6 C7 1.536(3) . ?
C9 C10 1.509(3) . ?
C9 C11 1.513(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 O1 C9 110.72(16) . . ?
C8 O2 C9 108.07(16) . . ?
O1 C1 C2 106.48(18) . . ?
O1 C1 C8 103.88(16) . . ?
C2 C1 C8 112.19(17) . . ?
O1 C1 C6 108.01(16) . . ?
C2 C1 C6 110.50(17) . . ?
C8 C1 C6 115.12(18) . . ?
F1 C2 F2 103.25(17) . . ?
F1 C2 C3 110.1(2) . . ?
F2 C2 C3 110.22(18) . . ?
F1 C2 C1 109.66(17) . . ?
F2 C2 C1 108.80(19) . . ?
C3 C2 C1 114.23(18) . . ?
C4 C3 C2 121.4(2) . . ?
C3 C4 C5 124.3(2) . . ?
C4 C5 C6 113.27(19) . . ?
O3 C6 C7 109.84(19) . . ?
O3 C6 C5 106.08(18) . . ?
C7 C6 C5 110.46(18) . . ?
O3 C6 C1 108.49(17) . . ?
C7 C6 C1 113.92(18) . . ?
C5 C6 C1 107.73(18) . . ?
O2 C8 C1 103.99(17) . . ?
O1 C9 O2 105.28(17) . . ?
O1 C9 C10 108.95(18) . . ?
O2 C9 C10 108.35(19) . . ?
O1 C9 C11 109.21(19) . . ?
O2 C9 C11 111.3(2) . . ?
C10 C9 C11 113.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.900
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_full 0.900
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.076
#===END