# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Jun-An Ma'
_publ_contact_author_email       'MAJUN AN68@TJU.EDU.CN'

_publ_section_title              
;
Perfectly Double Roles of CF3 Group in Activating Substrates
and Stabilizing Adducts: Chiral Br\/onsted Acid-Catalyzed Direct Arylation
of Simple Trifluoromethyl Ketones
;
loop_
_publ_author_name
'Jun-An Ma.'
'Aiping Fu.'
'Jing Nie.'
'Lian Wang.'
'Guang-Wu Zhang.'
;
Yan Zheng
;

# Attachment '1.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 713022'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            
1-(4-chlorophenyl)-2,2,2-trifluoro-1-(1H-indole-3-yl)ethanol
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 Cl F3 N O'
_chemical_formula_weight         325.71

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   7.4634(15)
_cell_length_b                   13.393(3)
_cell_length_c                   15.347(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1534.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12745
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.7
_cell_measurement_temperature    293.1

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.280
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  SCX-MINI
_diffrn_measurement_method       multi-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16222
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_sigmaI/netI    0.0656
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3510
_reflns_number_gt                2190
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_structure_solution    DirectMethod
_computing_structure_refinement  SHELXL
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_molecular_graphics    ?

_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^)+(0.0281P)^2^+0.2240P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_number_reflns         3510
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration rm

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
Cl1 Cl -0.10773(15) 0.81613(7) 0.47079(6) 0.0800(3) Uani 1 1 d . . .
O1 O -0.0720(3) 0.87375(19) 0.90041(16) 0.0563(7) Uani 1 1 d . . .
C1 C 0.4846(4) 0.7836(3) 0.89830(18) 0.0479(8) Uani 1 1 d . . .
F2 F 0.0610(3) 1.06189(15) 0.93693(13) 0.0844(7) Uani 1 1 d . . .
C2 C -0.0583(5) 0.8439(2) 0.57960(19) 0.0513(8) Uani 1 1 d . . .
C3 C 0.2455(3) 0.8860(2) 0.87110(17) 0.0383(7) Uani 1 1 d . . .
C4 C 0.0158(4) 0.8887(2) 0.75128(19) 0.0406(7) Uani 1 1 d . . .
C5 C 0.1041(5) 0.8828(3) 0.6007(2) 0.0624(9) Uani 1 1 d . . .
H5A H 0.1892 0.8944 0.5576 0.075 Uiso 1 1 calc R . .
C6 C 0.3015(4) 0.7831(2) 0.87459(17) 0.0401(7) Uani 1 1 d . . .
F1 F -0.1337(3) 1.05786(17) 0.83331(14) 0.0907(7) Uani 1 1 d . . .
C7 C 0.0601(4) 0.9184(2) 0.84505(19) 0.0430(7) Uani 1 1 d . . .
C8 C -0.1841(4) 0.8252(2) 0.6423(2) 0.0531(8) Uani 1 1 d . . .
H8A H -0.2936 0.7968 0.6274 0.064 Uiso 1 1 calc R . .
F3 F 0.1435(3) 1.08398(14) 0.80416(15) 0.0891(7) Uani 1 1 d . . .
C9 C 0.5830(5) 0.6959(3) 0.9058(2) 0.0684(11) Uani 1 1 d . . .
H9A H 0.7037 0.6970 0.9210 0.082 Uiso 1 1 calc R . .
C10 C 0.3912(4) 0.9420(2) 0.8918(2) 0.0534(8) Uani 1 1 d . . .
H10A H 0.3938 1.0114 0.8939 0.064 Uiso 1 1 calc R . .
N1 N 0.5329(4) 0.8811(3) 0.9090(2) 0.0613(9) Uani 1 1 d . . .
C11 C -0.1469(4) 0.8490(2) 0.7284(2) 0.0504(8) Uani 1 1 d . . .
H11A H -0.2332 0.8379 0.7710 0.061 Uiso 1 1 calc R . .
C12 C 0.2165(5) 0.6920(3) 0.8597(2) 0.0598(9) Uani 1 1 d . . .
H12A H 0.0958 0.6899 0.8447 0.072 Uiso 1 1 calc R . .
C13 C 0.1417(4) 0.9049(2) 0.6866(2) 0.0573(9) Uani 1 1 d . . .
H13A H 0.2532 0.9310 0.7012 0.069 Uiso 1 1 calc R . .
C14 C 0.0331(5) 1.0313(3) 0.8544(2) 0.0613(10) Uani 1 1 d . . .
C15 C 0.4952(7) 0.6075(3) 0.8898(2) 0.0792(13) Uani 1 1 d . . .
H15A H 0.5581 0.5477 0.8939 0.095 Uiso 1 1 calc R . .
C16 C 0.3136(6) 0.6055(3) 0.8675(3) 0.0806(12) Uani 1 1 d . . .
H16A H 0.2576 0.5444 0.8579 0.097 Uiso 1 1 calc R . .
H1O H -0.033(4) 0.864(2) 0.950(2) 0.049(10) Uiso 1 1 d . . .
H1N H 0.622(5) 0.904(3) 0.918(2) 0.067(13) Uiso 1 1 d . . .

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
Cl1 0.1029(8) 0.0898(7) 0.0474(5) -0.0041(5) -0.0137(5) -0.0094(6)
O1 0.0284(12) 0.098(2) 0.0425(14) 0.0040(13) -0.0012(11) -0.0045(12)
C1 0.0351(18) 0.069(3) 0.0395(17) -0.0028(16) 0.0022(14) 0.0065(18)
F2 0.0938(16) 0.0820(15) 0.0774(14) -0.0363(12) -0.0237(13) 0.0265(13)
C2 0.066(2) 0.047(2) 0.0409(19) -0.0003(15) -0.0070(17) -0.0031(17)
C3 0.0239(15) 0.0497(19) 0.0413(17) -0.0017(15) 0.0004(13) -0.0037(15)
C4 0.0369(17) 0.0416(18) 0.0435(17) 0.0012(15) 0.0005(14) 0.0007(15)
C5 0.058(2) 0.080(3) 0.049(2) 0.0025(18) 0.0069(18) -0.012(2)
C6 0.0347(18) 0.049(2) 0.0372(17) -0.0025(14) 0.0010(13) -0.0014(15)
F1 0.0850(16) 0.0995(17) 0.0876(16) -0.0244(12) -0.0248(13) 0.0522(14)
C7 0.0327(17) 0.0507(19) 0.0456(19) 0.0001(14) 0.0020(14) 0.0001(15)
C8 0.0473(19) 0.051(2) 0.061(2) 0.0010(17) -0.0120(17) -0.0114(16)
F3 0.1148(19) 0.0454(12) 0.1070(18) 0.0045(11) 0.0016(15) -0.0034(14)
C9 0.057(2) 0.100(3) 0.048(2) 0.004(2) 0.0043(17) 0.036(3)
C10 0.0341(18) 0.054(2) 0.072(2) -0.0076(16) -0.0030(17) -0.0016(18)
N1 0.0278(16) 0.080(3) 0.076(2) -0.0074(18) -0.0056(15) -0.0125(18)
C11 0.043(2) 0.063(2) 0.0448(19) -0.0007(15) 0.0002(15) -0.0055(17)
C12 0.060(2) 0.055(2) 0.064(2) -0.0026(19) -0.0088(18) -0.001(2)
C13 0.0418(19) 0.078(2) 0.052(2) -0.0016(18) 0.0011(16) -0.0127(19)
C14 0.056(2) 0.061(3) 0.067(2) -0.012(2) -0.008(2) 0.016(2)
C15 0.114(4) 0.066(3) 0.058(3) 0.003(2) 0.001(2) 0.040(3)
C16 0.109(4) 0.056(3) 0.077(3) -0.005(2) -0.012(3) 0.011(2)

_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
Cl1 C2 1.750(3) . ?
O1 C7 1.432(3) . ?
O1 H1O 0.82(3) . ?
C1 N1 1.364(4) . ?
C1 C9 1.390(4) . ?
C1 C6 1.414(4) . ?
F2 C14 1.348(4) . ?
C2 C5 1.358(4) . ?
C2 C8 1.368(4) . ?
C3 C10 1.359(4) . ?
C3 C6 1.441(4) . ?
C3 C7 1.504(4) . ?
C4 C11 1.371(4) . ?
C4 C13 1.384(4) . ?
C4 C7 1.529(4) . ?
C5 C13 1.380(4) . ?
C5 H5A 0.9300 . ?
C6 C12 1.394(4) . ?
F1 C14 1.335(4) . ?
C7 C14 1.533(4) . ?
C8 C11 1.387(4) . ?
C8 H8A 0.9300 . ?
F3 C14 1.330(4) . ?
C9 C15 1.376(5) . ?
C9 H9A 0.9300 . ?
C10 N1 1.361(4) . ?
C10 H10A 0.9300 . ?
N1 H1N 0.74(4) . ?
C11 H11A 0.9300 . ?
C12 C16 1.372(5) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C15 C16 1.398(5) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?

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
C7 O1 H1O 112(2) . . ?
N1 C1 C9 131.2(3) . . ?
N1 C1 C6 106.9(3) . . ?
C9 C1 C6 121.9(3) . . ?
C5 C2 C8 121.0(3) . . ?
C5 C2 Cl1 119.8(3) . . ?
C8 C2 Cl1 119.2(3) . . ?
C10 C3 C6 106.7(2) . . ?
C10 C3 C7 129.7(3) . . ?
C6 C3 C7 123.6(2) . . ?
C11 C4 C13 118.6(3) . . ?
C11 C4 C7 122.2(3) . . ?
C13 C4 C7 119.2(3) . . ?
C2 C5 C13 119.4(3) . . ?
C2 C5 H5A 120.3 . . ?
C13 C5 H5A 120.3 . . ?
C12 C6 C1 119.1(3) . . ?
C12 C6 C3 134.3(3) . . ?
C1 C6 C3 106.6(3) . . ?
O1 C7 C3 110.8(2) . . ?
O1 C7 C4 107.5(2) . . ?
C3 C7 C4 112.0(2) . . ?
O1 C7 C14 105.4(3) . . ?
C3 C7 C14 112.4(2) . . ?
C4 C7 C14 108.4(2) . . ?
C2 C8 C11 119.4(3) . . ?
C2 C8 H8A 120.3 . . ?
C11 C8 H8A 120.3 . . ?
C15 C9 C1 117.4(3) . . ?
C15 C9 H9A 121.3 . . ?
C1 C9 H9A 121.3 . . ?
C3 C10 N1 109.6(3) . . ?
C3 C10 H10A 125.2 . . ?
N1 C10 H10A 125.2 . . ?
C10 N1 C1 110.2(3) . . ?
C10 N1 H1N 119(3) . . ?
C1 N1 H1N 131(3) . . ?
C4 C11 C8 120.7(3) . . ?
C4 C11 H11A 119.7 . . ?
C8 C11 H11A 119.7 . . ?
C16 C12 C6 119.0(3) . . ?
C16 C12 H12A 120.5 . . ?
C6 C12 H12A 120.5 . . ?
C5 C13 C4 120.9(3) . . ?
C5 C13 H13A 119.6 . . ?
C4 C13 H13A 119.6 . . ?
F3 C14 F1 107.3(3) . . ?
F3 C14 F2 106.7(3) . . ?
F1 C14 F2 106.9(3) . . ?
F3 C14 C7 112.8(3) . . ?
F1 C14 C7 111.3(3) . . ?
F2 C14 C7 111.5(3) . . ?
C9 C15 C16 121.5(4) . . ?
C9 C15 H15A 119.3 . . ?
C16 C15 H15A 119.3 . . ?
C12 C16 C15 121.1(4) . . ?
C12 C16 H16A 119.4 . . ?
C15 C16 H16A 119.4 . . ?

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
C8 C2 C5 C13 -0.8(5) . . . . ?
Cl1 C2 C5 C13 179.7(3) . . . . ?
N1 C1 C6 C12 -179.8(3) . . . . ?
C9 C1 C6 C12 1.1(4) . . . . ?
N1 C1 C6 C3 0.6(3) . . . . ?
C9 C1 C6 C3 -178.5(3) . . . . ?
C10 C3 C6 C12 -179.4(3) . . . . ?
C7 C3 C6 C12 -1.7(5) . . . . ?
C10 C3 C6 C1 0.1(3) . . . . ?
C7 C3 C6 C1 177.8(3) . . . . ?
C10 C3 C7 O1 -125.3(3) . . . . ?
C6 C3 C7 O1 57.6(3) . . . . ?
C10 C3 C7 C4 114.7(3) . . . . ?
C6 C3 C7 C4 -62.5(3) . . . . ?
C10 C3 C7 C14 -7.6(4) . . . . ?
C6 C3 C7 C14 175.2(3) . . . . ?
C11 C4 C7 O1 14.8(4) . . . . ?
C13 C4 C7 O1 -167.0(3) . . . . ?
C11 C4 C7 C3 136.7(3) . . . . ?
C13 C4 C7 C3 -45.1(4) . . . . ?
C11 C4 C7 C14 -98.7(3) . . . . ?
C13 C4 C7 C14 79.4(3) . . . . ?
C5 C2 C8 C11 1.8(5) . . . . ?
Cl1 C2 C8 C11 -178.7(2) . . . . ?
N1 C1 C9 C15 -179.3(3) . . . . ?
C6 C1 C9 C15 -0.5(4) . . . . ?
C6 C3 C10 N1 -0.8(3) . . . . ?
C7 C3 C10 N1 -178.3(3) . . . . ?
C3 C10 N1 C1 1.2(4) . . . . ?
C9 C1 N1 C10 177.9(3) . . . . ?
C6 C1 N1 C10 -1.1(4) . . . . ?
C13 C4 C11 C8 0.2(5) . . . . ?
C7 C4 C11 C8 178.4(3) . . . . ?
C2 C8 C11 C4 -1.5(5) . . . . ?
C1 C6 C12 C16 -0.7(5) . . . . ?
C3 C6 C12 C16 178.8(3) . . . . ?
C2 C5 C13 C4 -0.5(5) . . . . ?
C11 C4 C13 C5 0.8(5) . . . . ?
C7 C4 C13 C5 -177.4(3) . . . . ?
O1 C7 C14 F3 -178.0(3) . . . . ?
C3 C7 C14 F3 61.2(4) . . . . ?
C4 C7 C14 F3 -63.1(3) . . . . ?
O1 C7 C14 F1 -57.4(4) . . . . ?
C3 C7 C14 F1 -178.2(3) . . . . ?
C4 C7 C14 F1 57.5(4) . . . . ?
O1 C7 C14 F2 61.9(3) . . . . ?
C3 C7 C14 F2 -58.9(4) . . . . ?
C4 C7 C14 F2 176.8(3) . . . . ?
C1 C9 C15 C16 -0.5(5) . . . . ?
C6 C12 C16 C15 -0.2(5) . . . . ?
C9 C15 C16 C12 0.9(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.039