# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2004



data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        
'Prof. Dr. Francois Diederich'

_publ_contact_author_address     
;
Laboratorium fur Organische Chemie
ETH Honggerberg, HCI G313
CH-8093 Zurich
Switzerland
;

_publ_contact_author_email       diederich@org.chem.ethz.ch

_publ_section_title              
;
Nucleophilic Trifluoromethylation of cyclic imides using
(trifluoromethyl)trimethylsilane CF3SiMe3
;
loop_
_publ_author_name
'Anja Hoffmann-Roder'
'Paul Seiler'
'Francois Diederich'

data_compound12
_database_code_depnum_ccdc_archive 'CCDC 239185'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 F3 N O2'
_chemical_formula_sum            'C14 H14 F3 N O2'
_chemical_formula_weight         285.26

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                   6.4271(3)
_cell_length_b                   7.7669(4)
_cell_length_c                   14.1095(8)
_cell_angle_alpha                95.290(2)
_cell_angle_beta                 94.206(2)
_cell_angle_gamma                111.866(2)
_cell_volume                     646.44(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    2249
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      26.03

_exptl_crystal_description       'Cut fragment'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.126
_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      193(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_reflns_number            4375
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         26.03
_reflns_number_total             2530
_reflns_number_gt                1820
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Kappa CCD'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'Denzo + Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et Al., 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Johnson,1976)'
_computing_publication_material  SHELXL97

_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)+(0.0977P)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    'H-atoms riding'
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef       0.038(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2530
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1507
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_restrained_S_all      0.931
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0002(3) 0.2977(3) 0.31736(13) 0.0283(4) Uani 1 d . . .
N2 N 0.1963(2) 0.2868(2) 0.27524(11) 0.0272(4) Uani 1 d . . .
C3 C 0.3913(3) 0.4326(3) 0.30835(14) 0.0322(5) Uani 1 d . . .
C4 C 0.3419(3) 0.5773(3) 0.37164(15) 0.0331(5) Uani 1 d . . .
H4A H 0.4164 0.6076 0.4392 0.040 Uiso 1 calc R . .
C5 C 0.0825(3) 0.5037(3) 0.35917(13) 0.0294(4) Uani 1 d . . .
H5A H 0.0153 0.5274 0.4183 0.035 Uiso 1 calc R . .
C6 C 0.0961(3) 0.6426(3) 0.28580(16) 0.0372(5) Uani 1 d . . .
H6A H 0.0633 0.5838 0.2182 0.045 Uiso 1 calc R . .
H6B H 0.0056 0.7194 0.2985 0.045 Uiso 1 calc R . .
C7 C 0.3501(3) 0.7459(3) 0.31980(17) 0.0401(5) Uani 1 d . . .
H7A H 0.3866 0.8631 0.3635 0.048 Uiso 1 calc R . .
H7B H 0.4467 0.7667 0.2671 0.048 Uiso 1 calc R . .
O8 O 0.5783(2) 0.4457(2) 0.28848(12) 0.0456(4) Uani 1 d . . .
O9 O -0.1886(2) 0.23044(19) 0.24913(10) 0.0348(4) Uani 1 d . . .
H9A H -0.2686 0.2935 0.2582 0.052 Uiso 1 calc R . .
C10 C -0.0512(4) 0.1724(3) 0.39725(15) 0.0391(5) Uani 1 d . . .
F11 F -0.0954(2) -0.00700(17) 0.36584(10) 0.0532(4) Uani 1 d . . .
F12 F -0.2311(2) 0.17612(19) 0.43896(10) 0.0532(4) Uani 1 d . . .
F13 F 0.1220(2) 0.2279(2) 0.46711(9) 0.0561(4) Uani 1 d . . .
C14 C 0.1862(3) 0.1336(3) 0.20310(14) 0.0315(5) Uani 1 d . . .
H14A H 0.0359 0.0310 0.1986 0.038 Uiso 1 calc R . .
H14B H 0.3008 0.0841 0.2244 0.038 Uiso 1 calc R . .
C15 C 0.2270(3) 0.1939(3) 0.10506(14) 0.0294(4) Uani 1 d . . .
C16 C 0.0816(4) 0.2600(3) 0.05715(15) 0.0376(5) Uani 1 d . . .
H16A H -0.0425 0.2696 0.0867 0.045 Uiso 1 calc R . .
C17 C 0.1161(4) 0.3121(3) -0.03370(16) 0.0432(6) Uani 1 d . . .
H17A H 0.0158 0.3575 -0.0659 0.052 Uiso 1 calc R . .
C18 C 0.2961(4) 0.2983(3) -0.07763(15) 0.0412(5) Uani 1 d . . .
H18A H 0.3196 0.3341 -0.1398 0.049 Uiso 1 calc R . .
C19 C 0.4402(4) 0.2325(3) -0.03067(16) 0.0420(5) Uani 1 d . . .
H19A H 0.5635 0.2222 -0.0606 0.050 Uiso 1 calc R . .
C20 C 0.4066(3) 0.1805(3) 0.06082(15) 0.0379(5) Uani 1 d . . .
H20A H 0.5076 0.1357 0.0929 0.045 Uiso 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
C1 O9 1.390(2) . ?
C1 N2 1.462(2) . ?
C1 C5 1.529(3) . ?
C1 C10 1.531(3) . ?
N2 C3 1.353(2) . ?
N2 C14 1.472(2) . ?
C3 O8 1.223(2) . ?
C3 C4 1.511(3) . ?
C4 C5 1.538(3) . ?
C4 C7 1.544(3) . ?
C5 C6 1.547(3) . ?
C6 C7 1.542(3) . ?
C10 F11 1.338(2) . ?
C10 F13 1.342(2) . ?
C10 F12 1.344(2) . ?
C14 C15 1.511(3) . ?
C15 C20 1.384(3) . ?
C15 C16 1.387(3) . ?
C16 C17 1.388(3) . ?
C17 C18 1.385(3) . ?
C18 C19 1.372(3) . ?
C19 C20 1.396(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
O9 C1 N2 110.33(14) . . ?
O9 C1 C5 116.94(15) . . ?
N2 C1 C5 102.67(15) . . ?
O9 C1 C10 107.41(16) . . ?
N2 C1 C10 108.68(15) . . ?
C5 C1 C10 110.56(16) . . ?
C3 N2 C1 113.63(15) . . ?
C3 N2 C14 122.46(16) . . ?
C1 N2 C14 123.91(15) . . ?
O8 C3 N2 124.82(18) . . ?
O8 C3 C4 125.48(18) . . ?
N2 C3 C4 109.69(16) . . ?
C3 C4 C5 103.19(15) . . ?
C3 C4 C7 112.21(17) . . ?
C5 C4 C7 89.74(15) . . ?
C1 C5 C4 106.35(15) . . ?
C1 C5 C6 115.73(16) . . ?
C4 C5 C6 88.72(15) . . ?
C7 C6 C5 89.49(15) . . ?
C6 C7 C4 88.65(15) . . ?
F11 C10 F13 107.14(18) . . ?
F11 C10 F12 106.76(17) . . ?
F13 C10 F12 106.48(17) . . ?
F11 C10 C1 112.82(17) . . ?
F13 C10 C1 111.65(17) . . ?
F12 C10 C1 111.62(17) . . ?
N2 C14 C15 112.95(15) . . ?
C20 C15 C16 118.96(19) . . ?
C20 C15 C14 120.77(17) . . ?
C16 C15 C14 120.26(17) . . ?
C17 C16 C15 120.41(19) . . ?
C18 C17 C16 120.4(2) . . ?
C19 C18 C17 119.5(2) . . ?
C18 C19 C20 120.3(2) . . ?
C15 C20 C19 120.45(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O9 C1 N2 C3 142.98(17) . . . . ?
C5 C1 N2 C3 17.6(2) . . . . ?
C10 C1 N2 C3 -99.49(19) . . . . ?
O9 C1 N2 C14 -36.6(2) . . . . ?
C5 C1 N2 C14 -161.95(16) . . . . ?
C10 C1 N2 C14 80.9(2) . . . . ?
C1 N2 C3 O8 174.38(18) . . . . ?
C14 N2 C3 O8 -6.0(3) . . . . ?
C1 N2 C3 C4 -6.7(2) . . . . ?
C14 N2 C3 C4 172.88(16) . . . . ?
O8 C3 C4 C5 171.62(19) . . . . ?
N2 C3 C4 C5 -7.3(2) . . . . ?
O8 C3 C4 C7 76.4(3) . . . . ?
N2 C3 C4 C7 -102.5(2) . . . . ?
O9 C1 C5 C4 -141.95(16) . . . . ?
N2 C1 C5 C4 -21.05(19) . . . . ?
C10 C1 C5 C4 94.74(19) . . . . ?
O9 C1 C5 C6 -45.3(2) . . . . ?
N2 C1 C5 C6 75.58(19) . . . . ?
C10 C1 C5 C6 -168.63(16) . . . . ?
C3 C4 C5 C1 17.6(2) . . . . ?
C7 C4 C5 C1 130.37(16) . . . . ?
C3 C4 C5 C6 -98.89(17) . . . . ?
C7 C4 C5 C6 13.89(15) . . . . ?
C1 C5 C6 C7 -121.47(17) . . . . ?
C4 C5 C6 C7 -13.91(15) . . . . ?
C5 C6 C7 C4 13.85(15) . . . . ?
C3 C4 C7 C6 90.23(18) . . . . ?
C5 C4 C7 C6 -13.93(15) . . . . ?
O9 C1 C10 F11 59.7(2) . . . . ?
N2 C1 C10 F11 -59.7(2) . . . . ?
C5 C1 C10 F11 -171.68(16) . . . . ?
O9 C1 C10 F13 -179.61(15) . . . . ?
N2 C1 C10 F13 61.0(2) . . . . ?
C5 C1 C10 F13 -50.9(2) . . . . ?
O9 C1 C10 F12 -60.6(2) . . . . ?
N2 C1 C10 F12 -179.92(15) . . . . ?
C5 C1 C10 F12 68.1(2) . . . . ?
C3 N2 C14 C15 -69.6(2) . . . . ?
C1 N2 C14 C15 109.94(19) . . . . ?
N2 C14 C15 C20 119.42(19) . . . . ?
N2 C14 C15 C16 -61.9(2) . . . . ?
C20 C15 C16 C17 -0.1(3) . . . . ?
C14 C15 C16 C17 -178.77(19) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 C19 0.1(3) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C16 C15 C20 C19 -0.1(3) . . . . ?
C14 C15 C20 C19 178.54(18) . . . . ?
C18 C19 C20 C15 0.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.03
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.045

#==END


