data_00sot036
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C16 H17 F3 O2'
_chemical_formula_weight          298.30
 
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            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                    9.2288(18)
_cell_length_b                    20.362(4)
_cell_length_c                    7.6375(15)
_cell_angle_alpha                 90.00
_cell_angle_beta                  91.00(3)
_cell_angle_gamma                 90.00
_cell_volume                      1435.0(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     13593
_cell_measurement_theta_min       2.98
_cell_measurement_theta_max       27.5
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.25
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.381
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              624
_exptl_absorpt_coefficient_mu     0.115
_exptl_absorpt_correction_type    multi-scans
_exptl_absorpt_correction_T_min   0.9717
_exptl_absorpt_correction_T_max   0.9943
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'Phi and Omega scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             13593
_diffrn_reflns_av_R_equivalents   0.0734
_diffrn_reflns_av_sigmaI/netI     0.0550
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -26
_diffrn_reflns_limit_k_max        26
_diffrn_reflns_limit_l_min        -9
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_theta_min          2.98
_diffrn_reflns_theta_max          27.50
_reflns_number_total              3244
_reflns_number_gt                 2259
_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     'CAMERON (Watkin, Pearce 1995)'
_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)+(0.1000P)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      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          3244
_refine_ls_number_parameters      190
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0860
_refine_ls_R_factor_gt            0.0571
_refine_ls_wR_factor_ref          0.1774
_refine_ls_wR_factor_gt           0.1599
_refine_ls_goodness_of_fit_ref    1.136
_refine_ls_restrained_S_all       1.136
_refine_ls_shift/su_max           0.006
_refine_ls_shift/su_mean          0.001
 
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 0.65974(15) 0.27918(5) 0.51197(17) 0.0488(4) Uani 1 1 d . . .
F2 F 0.55803(14) 0.35186(6) 0.34722(16) 0.0467(4) Uani 1 1 d . . .
F3 F 0.77844(14) 0.32558(7) 0.30770(16) 0.0479(4) Uani 1 1 d . . .
O1 O 0.43497(15) 0.49164(6) 0.77463(18) 0.0360(4) Uani 1 1 d . . .
O2 O 0.77129(15) 0.44558(6) 0.45906(18) 0.0367(4) Uani 1 1 d . . .
H2 H 0.7044 0.4575 0.3946 0.055 Uiso 1 1 calc R . .
C1 C 0.5974(2) 0.40742(9) 0.6750(2) 0.0299(4) Uani 1 1 d . . .
C2 C 0.5264(2) 0.35528(9) 0.7841(3) 0.0374(5) Uani 1 1 d . . .
H2A H 0.5996 0.3260 0.8328 0.045 Uiso 1 1 calc R . .
H2B H 0.4605 0.3296 0.7114 0.045 Uiso 1 1 calc R . .
C3 C 0.4439(2) 0.38757(10) 0.9308(3) 0.0388(5) Uani 1 1 d . . .
H3A H 0.3841 0.3551 0.9881 0.047 Uiso 1 1 calc R . .
H3B H 0.5118 0.4052 1.0170 0.047 Uiso 1 1 calc R . .
C4 C 0.3503(2) 0.44168(11) 0.8597(3) 0.0409(5) Uani 1 1 d . . .
H4A H 0.2806 0.4236 0.7763 0.049 Uiso 1 1 calc R . .
H4B H 0.2969 0.4614 0.9546 0.049 Uiso 1 1 calc R . .
C5 C 0.5521(2) 0.46933(9) 0.6842(2) 0.0311(4) Uani 1 1 d . . .
H5 H 0.6051 0.5005 0.6235 0.037 Uiso 1 1 calc R . .
C6 C 0.7261(2) 0.39138(9) 0.5601(2) 0.0300(4) Uani 1 1 d . . .
C7 C 0.6815(2) 0.33701(10) 0.4309(3) 0.0355(5) Uani 1 1 d . . .
C8 C 0.8591(2) 0.36978(9) 0.6746(3) 0.0316(4) Uani 1 1 d . . .
H8 H 0.8282 0.3317 0.7429 0.038 Uiso 1 1 calc R . .
C9 C 0.8991(2) 0.42299(10) 0.8044(3) 0.0384(5) Uani 1 1 d . . .
H9 H 0.9181 0.4648 0.7617 0.046 Uiso 1 1 calc R . .
C10 C 0.9085(3) 0.41348(13) 0.9732(3) 0.0525(6) Uani 1 1 d . . .
H10A H 0.8901 0.3721 1.0195 0.063 Uiso 1 1 calc R . .
H10B H 0.9336 0.4481 1.0473 0.063 Uiso 1 1 calc R . .
C11 C 0.9892(2) 0.34802(9) 0.5705(2) 0.0319(5) Uani 1 1 d . . .
C12 C 1.0269(2) 0.28210(10) 0.5707(3) 0.0391(5) Uani 1 1 d . . .
H12 H 0.9720 0.2523 0.6336 0.047 Uiso 1 1 calc R . .
C13 C 1.1454(3) 0.26004(13) 0.4781(4) 0.0534(6) Uani 1 1 d . . .
H13 H 1.1680 0.2155 0.4767 0.064 Uiso 1 1 calc R . .
C14 C 1.2294(2) 0.30387(13) 0.3886(3) 0.0507(6) Uani 1 1 d . . .
H14 H 1.3099 0.2892 0.3282 0.061 Uiso 1 1 calc R . .
C15 C 1.1946(3) 0.36912(13) 0.3883(3) 0.0498(6) Uani 1 1 d . . .
H15 H 1.2510 0.3987 0.3266 0.060 Uiso 1 1 calc R . .
C16 C 1.0752(2) 0.39143(11) 0.4797(3) 0.0418(5) Uani 1 1 d . . .
H16 H 1.0531 0.4360 0.4797 0.050 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 C7 1.347(2) . ?
F2 C7 1.332(2) . ?
F3 C7 1.330(2) . ?
O1 C5 1.371(2) . ?
O1 C4 1.444(3) . ?
O2 C6 1.414(2) . ?
C1 C5 1.330(3) . ?
C1 C2 1.507(3) . ?
C1 C6 1.524(3) . ?
C2 C3 1.516(3) . ?
C3 C4 1.496(3) . ?
C6 C7 1.534(3) . ?
C6 C8 1.558(3) . ?
C8 C9 1.510(3) . ?
C8 C11 1.518(3) . ?
C9 C10 1.305(3) . ?
C11 C16 1.383(3) . ?
C11 C12 1.387(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.372(4) . ?
C14 C15 1.367(4) . ?
C15 C16 1.391(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
C5 O1 C4 115.54(15) . . ?
C5 C1 C2 119.88(18) . . ?
C5 C1 C6 118.84(17) . . ?
C2 C1 C6 121.21(16) . . ?
C1 C2 C3 109.41(16) . . ?
C4 C3 C2 110.20(17) . . ?
O1 C4 C3 111.61(17) . . ?
C1 C5 O1 126.32(18) . . ?
O2 C6 C1 112.78(15) . . ?
O2 C6 C7 106.88(15) . . ?
C1 C6 C7 108.78(16) . . ?
O2 C6 C8 106.85(15) . . ?
C1 C6 C8 110.59(15) . . ?
C7 C6 C8 110.91(15) . . ?
F3 C7 F2 106.28(16) . . ?
F3 C7 F1 106.26(16) . . ?
F2 C7 F1 106.59(17) . . ?
F3 C7 C6 113.91(17) . . ?
F2 C7 C6 111.25(16) . . ?
F1 C7 C6 112.07(16) . . ?
C9 C8 C11 111.52(16) . . ?
C9 C8 C6 110.31(15) . . ?
C11 C8 C6 114.28(16) . . ?
C10 C9 C8 123.6(2) . . ?
C16 C11 C12 118.2(2) . . ?
C16 C11 C8 122.87(18) . . ?
C12 C11 C8 118.87(18) . . ?
C11 C12 C13 120.8(2) . . ?
C14 C13 C12 120.1(2) . . ?
C15 C14 C13 119.9(2) . . ?
C14 C15 C16 120.3(2) . . ?
C11 C16 C15 120.7(2) . . ?
 
_diffrn_measured_fraction_theta_max    0.987
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.987
_refine_diff_density_max    0.511
_refine_diff_density_min   -0.253
_refine_diff_density_rms    0.057
