 
data_01sot120
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
John Keily
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C15 H19 F O4' 
_chemical_formula_weight          282.30 
 
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' 
 '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            Orthorhombic
_symmetry_space_group_name_H-M    Pna2(1)
 
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                    10.973(2) 
_cell_length_b                    12.764(3) 
_cell_length_c                    20.721(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      2902.2(10) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     6499 
_cell_measurement_theta_min       1.02 
_cell_measurement_theta_max       27.48 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.10 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.292 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1200 
_exptl_absorpt_coefficient_mu     0.101 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9900 
_exptl_absorpt_correction_T_max   0.9900 
_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          'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD' 
_diffrn_measurement_method        'Φ & ω scans' 
_diffrn_detector_area_resol_mean  9.091 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             22611 
_diffrn_reflns_av_R_equivalents   0.0812 
_diffrn_reflns_av_sigmaI/netI     0.0760 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        15 
_diffrn_reflns_limit_l_min        -22 
_diffrn_reflns_limit_l_max        24 
_diffrn_reflns_theta_min          3.14 
_diffrn_reflns_theta_max          25.02 
_reflns_number_total              5008 
_reflns_number_gt                 2794 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'COLLECT (Hooft, 1998)' 
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' 
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0686P)²+0.0000P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0100(12) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    -0.2(12) 
_refine_ls_number_reflns          5008 
_refine_ls_number_parameters      366 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.1088 
_refine_ls_R_factor_gt            0.0452 
_refine_ls_wR_factor_ref          0.1305 
_refine_ls_wR_factor_gt           0.1013 
_refine_ls_goodness_of_fit_ref    0.882 
_refine_ls_restrained_S_all       0.882 
_refine_ls_shift/su_max           0.257 
_refine_ls_shift/su_mean          0.010 
 
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 0.9050(3) 0.6712(2) 0.35931(16) 0.1213(11) Uani 1 1 d . . . 
O1 O 0.0702(3) 0.4229(3) 0.35746(17) 0.1020(10) Uani 1 1 d . . . 
H1 H -0.0013 0.4371 0.3459 0.153 Uiso 1 1 calc R . . 
O2 O 0.3238(2) 0.43483(17) 0.37002(13) 0.0669(7) Uani 1 1 d . . . 
O3 O 0.3325(3) 0.4025(2) 0.50961(15) 0.0795(8) Uani 1 1 d . . . 
H3 H 0.2816 0.4500 0.5021 0.119 Uiso 1 1 calc R . . 
O4 O 0.3907(3) 0.5938(2) 0.48147(16) 0.0934(10) Uani 1 1 d . . . 
C1 C 0.0822(4) 0.3644(4) 0.2498(2) 0.0942(15) Uani 1 1 d . . . 
H1A H 0.0052 0.3995 0.2395 0.141 Uiso 1 1 calc R . . 
H1B H 0.0656 0.2931 0.2649 0.141 Uiso 1 1 calc R . . 
H1C H 0.1335 0.3616 0.2112 0.141 Uiso 1 1 calc R . . 
C2 C 0.1712(5) 0.5376(4) 0.2822(3) 0.1037(16) Uani 1 1 d . . . 
H2A H 0.0934 0.5711 0.2716 0.156 Uiso 1 1 calc R . . 
H2B H 0.2241 0.5380 0.2441 0.156 Uiso 1 1 calc R . . 
H2C H 0.2107 0.5760 0.3174 0.156 Uiso 1 1 calc R . . 
C3 C 0.1486(4) 0.4259(3) 0.3031(2) 0.0709(11) Uani 1 1 d . . . 
C4 C 0.2672(3) 0.3740(3) 0.3202(2) 0.0683(10) Uani 1 1 d . . . 
H4 H 0.3212 0.3741 0.2813 0.082 Uiso 1 1 calc R . . 
C5 C 0.2629(5) 0.2632(3) 0.3479(3) 0.1035(16) Uani 1 1 d . . . 
H5A H 0.1809 0.2479 0.3654 0.124 Uiso 1 1 calc R . . 
H5B H 0.2819 0.2111 0.3139 0.124 Uiso 1 1 calc R . . 
C6 C 0.3560(4) 0.2592(3) 0.4002(2) 0.0771(12) Uani 1 1 d . . . 
H6A H 0.4191 0.2061 0.3905 0.092 Uiso 1 1 calc R . . 
H6B H 0.3177 0.2420 0.4421 0.092 Uiso 1 1 calc R . . 
C7 C 0.4109(3) 0.3687(3) 0.40154(19) 0.0639(10) Uani 1 1 d . . . 
H7 H 0.4883 0.3687 0.3761 0.077 Uiso 1 1 calc R . . 
C8 C 0.4357(3) 0.4151(3) 0.46814(19) 0.0634(10) Uani 1 1 d . . . 
H8 H 0.5066 0.3774 0.4877 0.076 Uiso 1 1 calc R . . 
C9 C 0.4670(4) 0.5305(3) 0.4631(2) 0.0687(10) Uani 1 1 d . . . 
C10 C 0.5832(4) 0.5647(3) 0.43573(19) 0.0642(10) Uani 1 1 d . . . 
C11 C 0.6797(3) 0.4965(3) 0.42358(19) 0.0671(10) Uani 1 1 d . . . 
H11 H 0.6709 0.4242 0.4334 0.080 Uiso 1 1 calc R . . 
C12 C 0.7879(4) 0.5321(3) 0.3975(2) 0.0757(11) Uani 1 1 d . . . 
H12 H 0.8529 0.4851 0.3886 0.091 Uiso 1 1 calc R . . 
C13 C 0.7990(5) 0.6352(4) 0.3850(2) 0.0833(13) Uani 1 1 d . . . 
C14 C 0.7100(6) 0.7063(4) 0.3976(2) 0.0954(15) Uani 1 1 d . . . 
H14 H 0.7225 0.7787 0.3891 0.114 Uiso 1 1 calc R . . 
C15 C 0.5996(5) 0.6705(3) 0.4232(2) 0.0826(12) Uani 1 1 d . . . 
H15 H 0.5358 0.7188 0.4320 0.099 Uiso 1 1 calc R . . 
F2 F 0.8764(3) 1.1927(2) 0.09879(16) 0.1186(11) Uani 1 1 d . . . 
O5 O 0.0778(2) 0.9282(2) 0.13821(15) 0.0796(8) Uani 1 1 d . . . 
H5 H 0.1166 0.9296 0.1033 0.119 Uiso 1 1 calc R . . 
O6 O 0.3407(2) 0.93305(18) 0.14265(13) 0.0643(7) Uani 1 1 d . . . 
O7 O 0.3744(3) 0.7664(2) 0.04480(16) 0.0848(9) Uani 1 1 d . . . 
H7A H 0.3253 0.8063 0.0257 0.127 Uiso 1 1 calc R . . 
O8 O 0.4169(3) 0.9568(2) -0.00225(15) 0.0867(9) Uani 1 1 d . . . 
C16 C 0.0692(4) 0.9755(4) 0.2484(2) 0.0945(14) Uani 1 1 d . . . 
H16A H 0.0526 0.9022 0.2595 0.142 Uiso 1 1 calc R . . 
H16B H -0.0080 1.0121 0.2408 0.142 Uiso 1 1 calc R . . 
H16C H 0.1129 1.0093 0.2840 0.142 Uiso 1 1 calc R . . 
C17 C 0.1725(5) 1.0924(3) 0.1676(3) 0.0990(15) Uani 1 1 d . . . 
H17A H 0.2213 1.0931 0.1280 0.149 Uiso 1 1 calc R . . 
H17B H 0.2172 1.1280 0.2021 0.149 Uiso 1 1 calc R . . 
H17C H 0.0952 1.1288 0.1599 0.149 Uiso 1 1 calc R . . 
C18 C 0.1471(4) 0.9798(3) 0.1873(2) 0.0690(11) Uani 1 1 d . . . 
C19 C 0.2662(3) 0.9212(3) 0.1987(2) 0.0639(10) Uani 1 1 d . . . 
H19 H 0.3090 0.9526 0.2366 0.077 Uiso 1 1 calc R . . 
C20 C 0.2586(4) 0.8041(3) 0.2076(2) 0.0757(11) Uani 1 1 d . . . 
H20A H 0.1936 0.7737 0.1803 0.091 Uiso 1 1 calc R . . 
H20B H 0.2425 0.7859 0.2532 0.091 Uiso 1 1 calc R . . 
C21 C 0.3833(4) 0.7655(3) 0.1866(2) 0.0768(12) Uani 1 1 d . . . 
H21A H 0.3763 0.7000 0.1613 0.092 Uiso 1 1 calc R . . 
H21B H 0.4363 0.7526 0.2244 0.092 Uiso 1 1 calc R . . 
C22 C 0.4340(3) 0.8547(3) 0.1449(2) 0.0640(10) Uani 1 1 d . . . 
H22 H 0.5079 0.8846 0.1663 0.077 Uiso 1 1 calc R . . 
C23 C 0.4654(4) 0.8268(3) 0.0750(2) 0.0673(10) Uani 1 1 d . . . 
H23 H 0.5426 0.7853 0.0751 0.081 Uiso 1 1 calc R . . 
C24 C 0.4888(4) 0.9293(3) 0.0389(2) 0.0658(10) Uani 1 1 d . . . 
C25 C 0.5923(3) 0.9963(3) 0.05706(19) 0.0618(9) Uani 1 1 d . . . 
C26 C 0.7000(3) 0.9568(3) 0.08224(19) 0.0675(10) Uani 1 1 d . . . 
H26 H 0.7076 0.8838 0.0900 0.081 Uiso 1 1 calc R . . 
C27 C 0.7965(4) 1.0228(3) 0.0962(2) 0.0743(11) Uani 1 1 d . . . 
H27 H 0.8708 0.9961 0.1130 0.089 Uiso 1 1 calc R . . 
C28 C 0.7816(4) 1.1275(3) 0.0851(2) 0.0785(12) Uani 1 1 d . . . 
C29 C 0.6775(4) 1.1699(3) 0.0614(2) 0.0813(12) Uani 1 1 d . . . 
H29 H 0.6702 1.2434 0.0553 0.098 Uiso 1 1 calc R . . 
C30 C 0.5826(4) 1.1033(3) 0.0465(2) 0.0751(11) Uani 1 1 d . . . 
H30 H 0.5097 1.1311 0.0287 0.090 Uiso 1 1 calc R . . 
 
 
_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 C13 1.359(5) . ? 
O1 C3 1.419(5) . ? 
O2 C4 1.434(4) . ? 
O2 C7 1.432(4) . ? 
O3 C8 1.430(5) . ? 
O4 C9 1.224(4) . ? 
C1 C3 1.537(6) . ? 
C2 C3 1.510(6) . ? 
C3 C4 1.502(5) . ? 
C4 C5 1.526(5) . ? 
C5 C6 1.490(6) . ? 
C6 C7 1.522(5) . ? 
C7 C8 1.526(5) . ? 
C8 C9 1.517(5) . ? 
C9 C10 1.462(6) . ? 
C10 C15 1.388(5) . ? 
C10 C11 1.394(5) . ? 
C11 C12 1.382(6) . ? 
C12 C13 1.347(6) . ? 
C13 C14 1.358(7) . ? 
C14 C15 1.399(7) . ? 
F2 C28 1.362(5) . ? 
O5 C18 1.431(5) . ? 
O6 C22 1.432(4) . ? 
O6 C19 1.428(5) . ? 
O7 C23 1.407(4) . ? 
O8 C24 1.213(4) . ? 
C16 C18 1.529(6) . ? 
C17 C18 1.521(6) . ? 
C18 C19 1.524(5) . ? 
C19 C20 1.508(5) . ? 
C20 C21 1.517(6) . ? 
C21 C22 1.534(5) . ? 
C22 C23 1.530(6) . ? 
C23 C24 1.530(6) . ? 
C24 C25 1.470(5) . ? 
C25 C26 1.387(5) . ? 
C25 C30 1.388(5) . ? 
C26 C27 1.383(5) . ? 
C27 C28 1.366(5) . ? 
C28 C29 1.356(6) . ? 
C29 C30 1.380(6) . ? 
 
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 
C4 O2 C7 107.4(3) . . ? 
O1 C3 C2 110.6(4) . . ? 
O1 C3 C4 109.0(3) . . ? 
C2 C3 C4 110.0(3) . . ? 
O1 C3 C1 105.6(3) . . ? 
C2 C3 C1 110.8(4) . . ? 
C4 C3 C1 110.8(4) . . ? 
O2 C4 C3 107.9(3) . . ? 
O2 C4 C5 104.1(3) . . ? 
C3 C4 C5 118.1(3) . . ? 
C6 C5 C4 106.6(3) . . ? 
C5 C6 C7 104.6(3) . . ? 
O2 C7 C6 105.6(3) . . ? 
O2 C7 C8 107.6(3) . . ? 
C6 C7 C8 116.3(4) . . ? 
O3 C8 C9 109.3(3) . . ? 
O3 C8 C7 111.0(3) . . ? 
C9 C8 C7 110.8(3) . . ? 
O4 C9 C10 121.4(4) . . ? 
O4 C9 C8 117.7(4) . . ? 
C10 C9 C8 120.9(3) . . ? 
C15 C10 C11 118.4(4) . . ? 
C15 C10 C9 118.5(4) . . ? 
C11 C10 C9 123.1(3) . . ? 
C12 C11 C10 121.2(4) . . ? 
C13 C12 C11 118.4(4) . . ? 
C12 C13 F1 118.9(5) . . ? 
C12 C13 C14 123.4(4) . . ? 
F1 C13 C14 117.7(4) . . ? 
C13 C14 C15 118.5(4) . . ? 
C10 C15 C14 120.1(4) . . ? 
C22 O6 C19 108.0(3) . . ? 
O5 C18 C19 109.9(3) . . ? 
O5 C18 C16 105.9(3) . . ? 
C19 C18 C16 109.5(3) . . ? 
O5 C18 C17 110.0(4) . . ? 
C19 C18 C17 110.4(3) . . ? 
C16 C18 C17 111.0(3) . . ? 
O6 C19 C20 103.7(3) . . ? 
O6 C19 C18 108.2(3) . . ? 
C20 C19 C18 117.3(3) . . ? 
C19 C20 C21 103.7(3) . . ? 
C20 C21 C22 104.3(3) . . ? 
O6 C22 C21 106.1(3) . . ? 
O6 C22 C23 107.0(3) . . ? 
C21 C22 C23 116.2(3) . . ? 
O7 C23 C24 111.7(3) . . ? 
O7 C23 C22 112.9(3) . . ? 
C24 C23 C22 107.6(3) . . ? 
O8 C24 C25 121.0(4) . . ? 
O8 C24 C23 118.8(4) . . ? 
C25 C24 C23 120.1(4) . . ? 
C26 C25 C30 118.8(3) . . ? 
C26 C25 C24 122.9(3) . . ? 
C30 C25 C24 118.2(3) . . ? 
C27 C26 C25 120.7(4) . . ? 
C28 C27 C26 118.0(4) . . ? 
C29 C28 F2 118.3(4) . . ? 
C29 C28 C27 123.5(4) . . ? 
F2 C28 C27 118.1(4) . . ? 
C28 C29 C30 118.1(4) . . ? 
C29 C30 C25 120.9(4) . . ? 
 
_diffrn_measured_fraction_theta_max    0.997 
_diffrn_reflns_theta_full              25.02 
_diffrn_measured_fraction_theta_full   0.997 
_refine_diff_density_max    0.116 
_refine_diff_density_min   -0.129 
_refine_diff_density_rms    0.033 
