# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 207/390

data_c2182_274_3

_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C25 H31 F O6'
_chemical_formula_weight          446.50

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'
 '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            monoclinic
_symmetry_space_group_name_H-M    P2(1)

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

_cell_length_a                    6.1029(16)
_cell_length_b                    13.105(2)
_cell_length_c                    14.153(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  94.418(15)
_cell_angle_gamma                 90.00
_cell_volume                      1128.5(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     160(2)
_cell_measurement_reflns_used     59
_cell_measurement_theta_min       18.35
_cell_measurement_theta_max       23.93

_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.23
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.12
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.314
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              476
_exptl_absorpt_coefficient_mu     0.813
_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       160(2)
_diffrn_radiation_wavelength      1.54184
_diffrn_radiation_type            CuK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Stoe-Siemens diffractometer'
_diffrn_measurement_method        '\w/\q scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          5
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   60
_diffrn_standards_decay_%         4
_diffrn_reflns_number             3304
_diffrn_reflns_av_R_equivalents   0.0711
_diffrn_reflns_av_sigmaI/netI     0.0938
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          3.13
_diffrn_reflns_theta_max          59.92
_reflns_number_total              3171
_reflns_number_obs                2320
_reflns_threshold_expression      >2sigma(I)

_computing_data_collection        'Stoe DIF4'
_computing_cell_refinement        'Stoe DIF4'
_computing_data_reduction         'local programs'
_computing_structure_solution     'Siemens SHELXTL'
_computing_structure_refinement   'Siemens SHELXTL'
_computing_molecular_graphics     'Siemens SHELXTL'
_computing_publication_material   'SHELXTL and local programs'

_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^)+(0.1068P)^2^+0.6411P] 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        0.0037(10)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.4(4)
_refine_ls_number_reflns          3171
_refine_ls_number_parameters      294
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.1104
_refine_ls_R_factor_obs           0.0730
_refine_ls_wR_factor_all          0.1973
_refine_ls_wR_factor_obs          0.1707
_refine_ls_goodness_of_fit_all    1.043
_refine_ls_restrained_S_all       1.043
_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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
C1 C 0.1784(11) 0.7604(5) 0.0319(5) 0.021(2) Uani 1 d . . 
H1 H 0.1118(11) 0.6994(5) 0.0075(5) 0.026 Uiso 1 calc R . 
C2 C 0.0813(11) 0.8470(5) 0.0069(5) 0.024(2) Uani 1 d . . 
H2 H -0.0448(11) 0.8460(5) -0.0369(5) 0.028 Uiso 1 calc R . 
C3 C 0.1632(11) 0.9448(5) 0.0450(5) 0.024(2) Uani 1 d . . 
O3 O 0.0671(8) 1.0249(4) 0.0261(4) 0.0373(13) Uani 1 d . . 
C4 C 0.3684(12) 0.9405(5) 0.1061(5) 0.025(2) Uani 1 d . . 
H4 H 0.4316(12) 1.0027(5) 0.1296(5) 0.030 Uiso 1 calc R . 
C5 C 0.4695(10) 0.8533(5) 0.1298(5) 0.021(2) Uani 1 d . . 
C6 C 0.6744(11) 0.8494(5) 0.1962(5) 0.026(2) Uani 1 d . . 
H6A H 0.7119(11) 0.9192(5) 0.2188(5) 0.032 Uiso 1 calc R . 
H6B H 0.7980(11) 0.8238(5) 0.1615(5) 0.032 Uiso 1 calc R . 
C7 C 0.6456(12) 0.7809(5) 0.2810(5) 0.023(2) Uani 1 d . . 
H7A H 0.5499(12) 0.8160(5) 0.3241(5) 0.028 Uiso 1 calc R . 
H7B H 0.7908(12) 0.7706(5) 0.3159(5) 0.028 Uiso 1 calc R . 
C8 C 0.5453(11) 0.6756(5) 0.2548(5) 0.018(2) Uani 1 d . . 
H8 H 0.6560(11) 0.6343(5) 0.2229(5) 0.022 Uiso 1 calc R . 
F9 F 0.1902(6) 0.7501(3) 0.2342(3) 0.0214(9) Uani 1 d . . 
C9 C 0.3377(11) 0.6878(5) 0.1863(5) 0.020(2) Uani 1 d . . 
C10 C 0.3855(11) 0.7496(6) 0.0958(5) 0.024(2) Uani 1 d . . 
C11 C 0.2013(11) 0.5889(5) 0.1667(5) 0.022(2) Uani 1 d . . 
H11 H 0.0533(11) 0.6095(5) 0.1377(5) 0.026 Uiso 1 calc R . 
O11 O 0.3005(8) 0.5271(4) 0.1005(3) 0.0288(12) Uani 1 d . . 
H11A H 0.2040(20) 0.5057(50) 0.0598(33) 0.043 Uiso 1 calc R . 
C12 C 0.1667(10) 0.5302(5) 0.2584(4) 0.0207(15) Uani 1 d . . 
H12A H 0.0625(10) 0.5688(5) 0.2951(4) 0.025 Uiso 1 calc R . 
H12B H 0.0991(10) 0.4633(5) 0.2417(4) 0.025 Uiso 1 calc R . 
C13 C 0.3795(10) 0.5128(5) 0.3207(5) 0.0189(15) Uani 1 d . . 
C14 C 0.4842(11) 0.6191(5) 0.3418(5) 0.019(2) Uani 1 d . . 
H14 H 0.3678(11) 0.6611(5) 0.3692(5) 0.023 Uiso 1 calc R . 
C15 C 0.6604(11) 0.5979(5) 0.4249(5) 0.021(2) Uani 1 d . . 
H15A H 0.7996(11) 0.5744(5) 0.4006(5) 0.026 Uiso 1 calc R . 
H15B H 0.6898(11) 0.6602(5) 0.4635(5) 0.026 Uiso 1 calc R . 
C16 C 0.5604(11) 0.5148(5) 0.4830(5) 0.022(2) Uani 1 d . . 
O16 O 0.4725(7) 0.5493(3) 0.5670(3) 0.0252(12) Uani 1 d . . 
C16' C 0.6878(12) 0.4174(5) 0.5080(6) 0.029(2) Uani 1 d . . 
H16A H 0.8167(12) 0.4118(5) 0.4699(6) 0.034 Uiso 1 calc R . 
H16B H 0.7403(12) 0.4174(5) 0.5760(6) 0.034 Uiso 1 calc R . 
O16' O 0.5380(8) 0.3327(4) 0.4873(3) 0.0292(12) Uani 1 d . . 
O17 O 0.1721(7) 0.5225(3) 0.4654(3) 0.0214(10) Uani 1 d . . 
C17 C 0.3540(11) 0.4772(5) 0.4234(5) 0.021(2) Uani 1 d . . 
C18 C 0.5386(12) 0.4393(5) 0.2741(5) 0.028(2) Uani 1 d . . 
H18A H 0.4684(31) 0.3725(12) 0.2643(30) 0.042 Uiso 1 calc R . 
H18B H 0.6738(32) 0.4318(28) 0.3156(16) 0.042 Uiso 1 calc R . 
H18C H 0.5743(60) 0.4672(18) 0.2129(16) 0.042 Uiso 1 calc R . 
C19 C 0.5570(12) 0.7008(6) 0.0350(5) 0.029(2) Uani 1 d . . 
H19A H 0.4931(28) 0.6404(21) 0.0025(26) 0.044 Uiso 1 calc R . 
H19B H 0.6867(34) 0.6806(32) 0.0759(7) 0.044 Uiso 1 calc R . 
H19C H 0.6001(56) 0.7503(13) -0.0121(22) 0.044 Uiso 1 calc R . 
C20 C 0.3485(12) 0.3636(5) 0.4410(5) 0.024(2) Uani 1 d . . 
O20 O 0.1979(9) 0.3045(4) 0.4208(4) 0.0362(13) Uani 1 d . . 
C21 C 0.2595(11) 0.5889(5) 0.5408(5) 0.022(2) Uani 1 d . . 
H21 H 0.2717(11) 0.6602(5) 0.5164(5) 0.026 Uiso 1 calc R . 
C22 C 0.1184(13) 0.5876(6) 0.6224(5) 0.031(2) Uani 1 d . . 
H22A H 0.1178(13) 0.5178(6) 0.6491(5) 0.037 Uiso 1 calc R . 
H22B H -0.0344(13) 0.6047(6) 0.5992(5) 0.037 Uiso 1 calc R . 
C23 C 0.1938(15) 0.6608(6) 0.6993(6) 0.042(2) Uani 1 d . . 
H23A H 0.3376(15) 0.6376(6) 0.7287(6) 0.051 Uiso 1 calc R . 
H23B H 0.2160(15) 0.7286(6) 0.6706(6) 0.051 Uiso 1 calc R . 
C24 C 0.0374(20) 0.6717(9) 0.7748(7) 0.071(3) Uani 1 d . . 
H24A H -0.1042(45) 0.6968(57) 0.7467(11) 0.106 Uiso 1 calc R . 
H24B H 0.0972(63) 0.7203(45) 0.8228(29) 0.106 Uiso 1 calc R . 
H24C H 0.0167(100) 0.6053(15) 0.8046(38) 0.106 Uiso 1 calc R . 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
C1 0.019(4) 0.023(4) 0.021(4) 0.005(3) -0.003(3) -0.007(3) 
C2 0.020(4) 0.027(4) 0.024(4) 0.005(3) -0.003(3) -0.002(3) 
C3 0.028(4) 0.025(4) 0.018(4) 0.010(3) -0.003(3) 0.001(3) 
O3 0.041(3) 0.027(3) 0.042(3) 0.005(2) -0.014(2) 0.002(3) 
C4 0.029(4) 0.014(4) 0.030(4) 0.006(3) -0.004(3) -0.006(3) 
C5 0.017(4) 0.021(4) 0.024(4) 0.004(3) -0.003(3) -0.004(3) 
C6 0.017(4) 0.028(4) 0.032(4) 0.004(3) -0.009(3) -0.010(3) 
C7 0.023(4) 0.017(4) 0.027(4) -0.003(3) -0.014(3) 0.002(3) 
C8 0.015(4) 0.019(3) 0.021(4) -0.002(3) -0.003(3) 0.004(3) 
F9 0.014(2) 0.025(2) 0.024(2) 0.002(2) -0.004(2) 0.003(2) 
C9 0.020(4) 0.019(4) 0.021(4) -0.002(3) 0.003(3) -0.002(3) 
C10 0.018(4) 0.029(4) 0.025(4) 0.001(3) -0.005(3) 0.002(3) 
C11 0.020(4) 0.023(4) 0.022(4) -0.006(3) -0.005(3) -0.006(3) 
O11 0.032(3) 0.026(3) 0.027(3) -0.005(2) -0.006(2) -0.010(2) 
C12 0.017(4) 0.021(3) 0.024(4) -0.001(3) -0.005(3) -0.002(3) 
C13 0.016(3) 0.021(3) 0.020(3) -0.003(3) 0.001(3) -0.001(3) 
C14 0.017(4) 0.018(4) 0.023(4) -0.004(3) 0.000(3) 0.005(3) 
C15 0.018(4) 0.017(3) 0.028(4) 0.008(3) -0.003(3) 0.003(3) 
C16 0.013(3) 0.024(4) 0.027(4) 0.003(3) -0.005(3) 0.000(3) 
O16 0.020(3) 0.029(3) 0.025(3) 0.000(2) -0.005(2) 0.001(2) 
C16' 0.025(4) 0.017(4) 0.044(5) 0.005(3) 0.001(3) 0.000(3) 
O16' 0.023(3) 0.021(3) 0.043(3) 0.006(2) -0.002(2) 0.002(2) 
O17 0.017(2) 0.023(2) 0.023(2) -0.003(2) 0.000(2) 0.000(2) 
C17 0.020(4) 0.017(3) 0.026(4) 0.001(3) 0.000(3) -0.006(3) 
C18 0.031(4) 0.022(4) 0.030(4) 0.004(3) -0.001(3) -0.003(3) 
C19 0.029(4) 0.030(4) 0.029(4) -0.003(3) 0.005(3) -0.001(3) 
C20 0.030(4) 0.016(4) 0.025(4) -0.001(3) 0.000(3) 0.004(3) 
O20 0.038(3) 0.023(3) 0.046(3) 0.003(2) -0.004(3) -0.009(3) 
C21 0.025(4) 0.010(3) 0.031(4) 0.000(3) 0.003(3) 0.005(3) 
C22 0.036(5) 0.026(4) 0.030(4) 0.004(3) 0.002(3) 0.006(3) 
C23 0.058(6) 0.033(5) 0.034(5) -0.005(3) -0.002(4) 0.014(4) 
C24 0.098(9) 0.085(8) 0.030(5) -0.017(5) 0.009(5) 0.012(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 
C1 C2 1.316(10) . ? 
C1 C10 1.504(9) . ? 
C2 C3 1.463(10) . ? 
C3 O3 1.223(8) . ? 
C3 C4 1.467(9) . ? 
C4 C5 1.330(9) . ? 
C5 C6 1.506(9) . ? 
C5 C10 1.518(10) . ? 
C6 C7 1.519(10) . ? 
C7 C8 1.543(9) . ? 
C8 C14 1.508(9) . ? 
C8 C9 1.543(9) . ? 
F9 C9 1.426(7) . ? 
C9 C11 1.554(9) . ? 
C9 C10 1.561(9) . ? 
C10 C19 1.545(10) . ? 
C11 O11 1.409(8) . ? 
C11 C12 1.537(9) . ? 
C12 C13 1.530(9) . ? 
C13 C17 1.546(10) . ? 
C13 C18 1.550(9) . ? 
C13 C14 1.553(9) . ? 
C14 C15 1.556(9) . ? 
C15 C16 1.521(9) . ? 
C16 O16 1.416(8) . ? 
C16 C16' 1.522(9) . ? 
C16 C17 1.542(9) . ? 
O16 C21 1.423(8) . ? 
C16' O16' 1.453(8) . ? 
O16' C20 1.347(9) . ? 
O17 C17 1.428(8) . ? 
O17 C21 1.447(8) . ? 
C17 C20 1.510(9) . ? 
C20 O20 1.219(9) . ? 
C21 C22 1.494(10) . ? 
C22 C23 1.496(11) . ? 
C23 C24 1.494(13) . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C2 C1 C10 125.7(7) . . ? 
C1 C2 C3 121.4(6) . . ? 
O3 C3 C2 121.8(6) . . ? 
O3 C3 C4 122.3(7) . . ? 
C2 C3 C4 115.9(6) . . ? 
C5 C4 C3 122.7(6) . . ? 
C4 C5 C6 122.3(6) . . ? 
C4 C5 C10 123.4(6) . . ? 
C6 C5 C10 114.3(6) . . ? 
C5 C6 C7 111.8(6) . . ? 
C6 C7 C8 114.0(6) . . ? 
C14 C8 C7 111.2(5) . . ? 
C14 C8 C9 108.8(5) . . ? 
C7 C8 C9 110.4(5) . . ? 
F9 C9 C8 106.2(5) . . ? 
F9 C9 C11 102.3(5) . . ? 
C8 C9 C11 115.3(5) . . ? 
F9 C9 C10 104.9(5) . . ? 
C8 C9 C10 111.9(5) . . ? 
C11 C9 C10 114.7(5) . . ? 
C1 C10 C5 110.7(6) . . ? 
C1 C10 C19 106.1(6) . . ? 
C5 C10 C19 108.7(6) . . ? 
C1 C10 C9 109.9(6) . . ? 
C5 C10 C9 106.5(5) . . ? 
C19 C10 C9 114.8(6) . . ? 
O11 C11 C12 111.6(6) . . ? 
O11 C11 C9 110.3(5) . . ? 
C12 C11 C9 111.9(5) . . ? 
C13 C12 C11 113.3(5) . . ? 
C12 C13 C17 116.4(5) . . ? 
C12 C13 C18 112.3(5) . . ? 
C17 C13 C18 108.9(5) . . ? 
C12 C13 C14 107.2(5) . . ? 
C17 C13 C14 99.2(5) . . ? 
C18 C13 C14 112.2(5) . . ? 
C8 C14 C13 114.0(5) . . ? 
C8 C14 C15 120.3(5) . . ? 
C13 C14 C15 103.6(5) . . ? 
C16 C15 C14 104.7(5) . . ? 
O16 C16 C15 114.7(6) . . ? 
O16 C16 C16' 107.0(6) . . ? 
C15 C16 C16' 120.5(6) . . ? 
O16 C16 C17 102.4(5) . . ? 
C15 C16 C17 106.2(5) . . ? 
C16' C16 C17 103.9(6) . . ? 
C16 O16 C21 107.1(5) . . ? 
O16' C16' C16 106.9(5) . . ? 
C20 O16' C16' 111.8(5) . . ? 
C17 O17 C21 107.6(5) . . ? 
O17 C17 C20 108.3(5) . . ? 
O17 C17 C16 105.6(5) . . ? 
C20 C17 C16 104.6(6) . . ? 
O17 C17 C13 113.8(5) . . ? 
C20 C17 C13 117.2(6) . . ? 
C16 C17 C13 106.3(5) . . ? 
O20 C20 O16' 121.8(6) . . ? 
O20 C20 C17 127.9(7) . . ? 
O16' C20 C17 110.3(6) . . ? 
O16 C21 O17 104.5(5) . . ? 
O16 C21 C22 111.3(5) . . ? 
O17 C21 C22 111.2(6) . . ? 
C21 C22 C23 113.1(7) . . ? 
C24 C23 C22 113.8(8) . . ? 
 
_refine_diff_density_max    0.251 
_refine_diff_density_min   -0.262 
_refine_diff_density_rms    0.063