data_99sot033
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C16 H19 F3 O3'
_chemical_formula_weight          316.31
 
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                    8.2480(7)
_cell_length_b                    10.7247(9)
_cell_length_c                    19.0148(18)
_cell_angle_alpha                 80.429(5)
_cell_angle_beta                  88.947(5)
_cell_angle_gamma                 71.679(5)
_cell_volume                      1573.5(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     na
_cell_measurement_theta_min       na
_cell_measurement_theta_max       na
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.10
_exptl_crystal_size_mid           0.05
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_diffrn     1.335
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              664
_exptl_absorpt_coefficient_mu     0.114
_exptl_absorpt_correction_type    Empirical
_exptl_absorpt_correction_T_min   0.9887
_exptl_absorpt_correction_T_max   0.9977
_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   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'Phi and Omega scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'not measured'
_diffrn_standards_interval_count  na
_diffrn_standards_interval_time   na
_diffrn_standards_decay_%         na
_diffrn_reflns_number             12744
_diffrn_reflns_av_R_equivalents   0.1345
_diffrn_reflns_av_sigmaI/netI     0.1646
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          3.05
_diffrn_reflns_theta_max          23.26
_reflns_number_total              4495
_reflns_number_gt                 2057
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection	      'COLLECT (Hooft, 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ORTEP
_computing_publication_material   CIFTAB
 
_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)+(0.0000P)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        0.0130(10)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          4495
_refine_ls_number_parameters      402
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1592
_refine_ls_R_factor_gt            0.0566
_refine_ls_wR_factor_ref          0.1165
_refine_ls_wR_factor_gt           0.0892
_refine_ls_goodness_of_fit_ref    0.927
_refine_ls_restrained_S_all       0.927
_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
F2A F 0.8509(3) 0.7075(2) 0.04135(14) 0.0581(8) Uani 1 1 d . . .
F1B F 0.4604(3) 1.0416(2) 0.31184(14) 0.0618(8) Uani 1 1 d . . .
O2B O 0.8012(3) 1.3187(2) 0.22273(14) 0.0356(8) Uani 1 1 d . . .
F1A F 0.7619(3) 0.5442(3) 0.08717(13) 0.0554(8) Uani 1 1 d . . .
O3A O 1.3223(3) 0.2403(3) 0.11497(15) 0.0373(8) Uani 1 1 d . . .
O1B O 0.4345(3) 1.2798(3) 0.36366(15) 0.0422(8) Uani 1 1 d . . .
H1B H 0.3905 1.2887 0.3229 0.063 Uiso 1 1 calc R . .
O1A O 0.8163(4) 0.5879(3) 0.22612(16) 0.0423(8) Uani 1 1 d . . .
H1A H 0.8065 0.5129 0.2240 0.063 Uiso 1 1 calc R . .
O2A O 1.2969(3) 0.3286(3) 0.22037(14) 0.0380(8) Uani 1 1 d . . .
O3B O 0.8565(3) 1.1482(3) 0.15494(16) 0.0407(8) Uani 1 1 d . . .
F2B F 0.6486(3) 0.9279(2) 0.39476(14) 0.0606(9) Uani 1 1 d . . .
F3B F 0.4000(3) 1.0444(3) 0.42169(15) 0.0639(9) Uani 1 1 d . . .
F3A F 0.6360(3) 0.7413(3) 0.10917(14) 0.0685(9) Uani 1 1 d . . .
C11B C 0.6939(5) 1.2928(4) 0.2762(2) 0.0333(12) Uani 1 1 d . . .
H11B H 0.6014 1.3662 0.2860 0.040 Uiso 1 1 calc R . .
C11A C 1.1422(5) 0.4291(4) 0.2165(2) 0.0320(12) Uani 1 1 d . . .
H11A H 1.0778 0.4336 0.2585 0.038 Uiso 1 1 calc R . .
C10B C 0.7093(5) 1.1747(4) 0.3148(2) 0.0320(11) Uani 1 1 d . . .
C3A C 0.9336(6) 0.7585(4) 0.1784(2) 0.0441(13) Uani 1 1 d . . .
H3A1 H 0.9681 0.8015 0.1329 0.053 Uiso 1 1 calc R . .
H3A2 H 0.8232 0.8192 0.1908 0.053 Uiso 1 1 calc R . .
C2B C 0.5845(5) 1.1666(4) 0.3738(2) 0.0372(12) Uani 1 1 d . . .
C2A C 0.9074(5) 0.6262(4) 0.1668(2) 0.0375(12) Uani 1 1 d . . .
C4A C 1.0653(6) 0.7415(4) 0.2357(3) 0.0412(13) Uani 1 1 d . . .
C12B C 0.9291(5) 1.2041(4) 0.2027(2) 0.0388(12) Uani 1 1 d . . .
H12B H 1.0246 1.2322 0.1795 0.047 Uiso 1 1 calc R . .
C10A C 1.0757(5) 0.5193(4) 0.1600(2) 0.0308(11) Uani 1 1 d . . .
C14A C 1.1750(5) 0.5238(4) 0.0932(2) 0.0412(13) Uani 1 1 d . . .
H14A H 1.1609 0.6176 0.0721 0.049 Uiso 1 1 calc R . .
H14B H 1.1306 0.4832 0.0579 0.049 Uiso 1 1 calc R . .
C1A C 0.7898(6) 0.6542(5) 0.1011(3) 0.0468(14) Uani 1 1 d . . .
C4B C 0.7589(6) 1.2590(5) 0.4469(2) 0.0390(12) Uani 1 1 d . . .
C12A C 1.3851(6) 0.3147(4) 0.1537(2) 0.0412(13) Uani 1 1 d . . .
H12A H 1.5097 0.2681 0.1648 0.049 Uiso 1 1 calc R . .
C3B C 0.6623(6) 1.1607(4) 0.4478(2) 0.0432(13) Uani 1 1 d . . .
H3B1 H 0.5696 1.1795 0.4822 0.052 Uiso 1 1 calc R . .
H3B2 H 0.7406 1.0696 0.4645 0.052 Uiso 1 1 calc R . .
C5A C 1.0292(6) 0.7231(4) 0.3075(3) 0.0457(13) Uani 1 1 d . . .
H5A H 0.9188 0.7205 0.3211 0.055 Uiso 1 1 calc R . .
C9B C 0.9344(6) 1.2170(5) 0.4447(2) 0.0503(14) Uani 1 1 d . . .
H9B H 0.9938 1.1245 0.4480 0.060 Uiso 1 1 calc R . .
C1B C 0.5254(6) 1.0452(5) 0.3751(3) 0.0484(14) Uani 1 1 d . . .
C13B C 0.9982(5) 1.0992(4) 0.2677(2) 0.0444(13) Uani 1 1 d . . .
H13A H 1.0558 1.1353 0.3008 0.053 Uiso 1 1 calc R . .
H13B H 1.0842 1.0210 0.2531 0.053 Uiso 1 1 calc R . .
C5B C 0.6752(7) 1.3947(5) 0.4428(2) 0.0536(15) Uani 1 1 d . . .
H5B H 0.5544 1.4263 0.4456 0.064 Uiso 1 1 calc R . .
C13A C 1.3630(5) 0.4484(4) 0.1102(2) 0.0445(13) Uani 1 1 d . . .
H13C H 1.4242 0.4378 0.0652 0.053 Uiso 1 1 calc R . .
H13D H 1.4133 0.5001 0.1368 0.053 Uiso 1 1 calc R . .
C8A C 1.3543(7) 0.7215(5) 0.2704(4) 0.0667(17) Uani 1 1 d . . .
H8A H 1.4666 0.7202 0.2574 0.080 Uiso 1 1 calc R . .
C14B C 0.8571(5) 1.0556(4) 0.3060(2) 0.0438(13) Uani 1 1 d . . .
H14C H 0.8195 0.9988 0.2781 0.053 Uiso 1 1 calc R . .
H14D H 0.9008 1.0024 0.3534 0.053 Uiso 1 1 calc R . .
C6A C 1.1520(8) 0.7084(5) 0.3594(3) 0.0581(15) Uani 1 1 d . . .
H6A H 1.1240 0.6994 0.4082 0.070 Uiso 1 1 calc R . .
C9A C 1.2290(7) 0.7386(4) 0.2183(3) 0.0544(15) Uani 1 1 d . . .
H9A H 1.2574 0.7484 0.1695 0.065 Uiso 1 1 calc R . .
C7B C 0.9416(9) 1.4388(7) 0.4316(3) 0.0759(19) Uani 1 1 d . . .
H7B H 1.0034 1.5009 0.4251 0.091 Uiso 1 1 calc R . .
C7A C 1.3125(8) 0.7067(5) 0.3409(3) 0.0678(17) Uani 1 1 d . . .
H7A H 1.3965 0.6952 0.3770 0.081 Uiso 1 1 calc R . .
C8B C 1.0265(7) 1.3059(7) 0.4378(3) 0.0670(17) Uani 1 1 d . . .
H8B H 1.1477 1.2746 0.4374 0.080 Uiso 1 1 calc R . .
C6B C 0.7662(9) 1.4831(6) 0.4349(3) 0.0758(19) Uani 1 1 d . . .
H6B H 0.7077 1.5757 0.4316 0.091 Uiso 1 1 calc R . .
C15A C 1.3749(5) 0.0997(4) 0.1436(2) 0.0400(13) Uani 1 1 d . . .
H15A H 1.3209 0.0840 0.1898 0.048 Uiso 1 1 calc R . .
H15B H 1.5005 0.0648 0.1516 0.048 Uiso 1 1 calc R . .
C16A C 1.3197(6) 0.0308(4) 0.0905(2) 0.0549(15) Uani 1 1 d . . .
H16A H 1.1948 0.0626 0.0848 0.082 Uiso 1 1 calc R . .
H16B H 1.3587 -0.0656 0.1074 0.082 Uiso 1 1 calc R . .
H16C H 1.3696 0.0503 0.0444 0.082 Uiso 1 1 calc R . .
C15B C 0.8225(6) 1.2267(4) 0.0844(2) 0.0441(13) Uani 1 1 d . . .
H15C H 0.9262 1.2474 0.0665 0.053 Uiso 1 1 calc R . .
H15D H 0.7299 1.3116 0.0853 0.053 Uiso 1 1 calc R . .
C16B C 0.7700(6) 1.1461(5) 0.0368(3) 0.0665(16) Uani 1 1 d . . .
H16D H 0.8629 1.0628 0.0360 0.100 Uiso 1 1 calc R . .
H16E H 0.7451 1.1972 -0.0117 0.100 Uiso 1 1 calc R . .
H16F H 0.6676 1.1259 0.0551 0.100 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
F2A C1A 1.347(5) . ?
F1B C1B 1.337(5) . ?
O2B C11B 1.386(5) . ?
O2B C12B 1.447(4) . ?
F1A C1A 1.338(5) . ?
O3A C12A 1.384(5) . ?
O3A C15A 1.444(4) . ?
O1B C2B 1.424(4) . ?
O1A C2A 1.419(5) . ?
O2A C11A 1.381(4) . ?
O2A C12A 1.456(5) . ?
O3B C12B 1.403(5) . ?
O3B C15B 1.442(4) . ?
F2B C1B 1.345(5) . ?
F3B C1B 1.351(5) . ?
F3A C1A 1.342(5) . ?
C11B C10B 1.324(5) . ?
C11A C10A 1.317(5) . ?
C10B C14B 1.494(5) . ?
C10B C2B 1.519(6) . ?
C3A C4A 1.501(6) . ?
C3A C2A 1.552(6) . ?
C2B C1B 1.525(6) . ?
C2B C3B 1.540(6) . ?
C2A C10A 1.517(5) . ?
C2A C1A 1.525(6) . ?
C4A C9A 1.376(6) . ?
C4A C5A 1.387(6) . ?
C12B C13B 1.510(5) . ?
C10A C14A 1.500(5) . ?
C14A C13A 1.519(5) . ?
C4B C9B 1.376(6) . ?
C4B C5B 1.391(5) . ?
C4B C3B 1.506(6) . ?
C12A C13A 1.491(5) . ?
C5A C6A 1.382(6) . ?
C9B C8B 1.383(7) . ?
C13B C14B 1.517(6) . ?
C5B C6B 1.371(7) . ?
C8A C7A 1.375(7) . ?
C8A C9A 1.393(7) . ?
C6A C7A 1.359(7) . ?
C7B C8B 1.362(6) . ?
C7B C6B 1.377(7) . ?
C15A C16A 1.500(6) . ?
C15B C16B 1.503(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
C11B O2B C12B 116.5(3) . . ?
C12A O3A C15A 114.1(3) . . ?
C11A O2A C12A 116.2(3) . . ?
C12B O3B C15B 113.4(3) . . ?
C10B C11B O2B 125.6(4) . . ?
C10A C11A O2A 126.0(4) . . ?
C11B C10B C14B 120.7(4) . . ?
C11B C10B C2B 118.2(4) . . ?
C14B C10B C2B 120.8(4) . . ?
C4A C3A C2A 114.0(3) . . ?
O1B C2B C10B 111.7(3) . . ?
O1B C2B C1B 106.4(4) . . ?
C10B C2B C1B 110.7(4) . . ?
O1B C2B C3B 106.5(4) . . ?
C10B C2B C3B 112.2(4) . . ?
C1B C2B C3B 109.1(4) . . ?
O1A C2A C10A 111.9(3) . . ?
O1A C2A C1A 106.4(4) . . ?
C10A C2A C1A 111.4(4) . . ?
O1A C2A C3A 106.0(3) . . ?
C10A C2A C3A 112.0(4) . . ?
C1A C2A C3A 108.8(4) . . ?
C9A C4A C5A 117.7(5) . . ?
C9A C4A C3A 120.5(5) . . ?
C5A C4A C3A 121.7(5) . . ?
O3B C12B O2B 110.0(3) . . ?
O3B C12B C13B 108.2(4) . . ?
O2B C12B C13B 110.3(3) . . ?
C11A C10A C14A 120.0(4) . . ?
C11A C10A C2A 118.5(4) . . ?
C14A C10A C2A 121.2(3) . . ?
C10A C14A C13A 110.0(3) . . ?
F1A C1A F3A 106.6(4) . . ?
F1A C1A F2A 106.6(4) . . ?
F3A C1A F2A 105.8(4) . . ?
F1A C1A C2A 112.5(4) . . ?
F3A C1A C2A 111.6(4) . . ?
F2A C1A C2A 113.2(4) . . ?
C9B C4B C5B 118.0(5) . . ?
C9B C4B C3B 120.1(4) . . ?
C5B C4B C3B 121.7(5) . . ?
O3A C12A O2A 110.5(4) . . ?
O3A C12A C13A 109.3(4) . . ?
O2A C12A C13A 110.2(4) . . ?
C4B C3B C2B 112.4(4) . . ?
C6A C5A C4A 120.8(5) . . ?
C4B C9B C8B 121.7(5) . . ?
F1B C1B F2B 106.9(4) . . ?
F1B C1B F3B 105.6(4) . . ?
F2B C1B F3B 105.3(4) . . ?
F1B C1B C2B 112.5(4) . . ?
F2B C1B C2B 114.2(4) . . ?
F3B C1B C2B 111.7(4) . . ?
C12B C13B C14B 111.5(3) . . ?
C6B C5B C4B 120.3(5) . . ?
C12A C13A C14A 110.7(4) . . ?
C7A C8A C9A 118.7(5) . . ?
C10B C14B C13B 110.1(4) . . ?
C7A C6A C5A 120.4(5) . . ?
C4A C9A C8A 121.8(5) . . ?
C8B C7B C6B 120.0(6) . . ?
C6A C7A C8A 120.5(5) . . ?
C7B C8B C9B 119.4(5) . . ?
C5B C6B C7B 120.6(6) . . ?
O3A C15A C16A 107.6(3) . . ?
O3B C15B C16B 107.5(3) . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
O1B H1B O2A  0.84 2.04 2.872(4) 172.9 1_465
O1A H1A O2B  0.84 2.10 2.940(4) 175.5 1_545
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              23.26
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.203
_refine_diff_density_min   -0.195
_refine_diff_density_rms    0.050
