#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:32:36 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178953 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/82/4118219.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4118219
loop_
_publ_author_name
'Nongnaphat Duangdee'
'Wacharee Harnying'
'Giuseppe Rulli'
'Jörg-M. Neudörfl'
'Harald Gröger'
'Albrecht Berkessel'
_publ_section_title
;
 Highly Enantioselective Organocatalytic Trifluoromethyl Carbinol
 Synthesis-A Caveat on Reaction Times and Product Isolation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11196
_journal_page_last               11205
_journal_paper_doi               10.1021/ja302511t
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C10 H10 F3 N O'
_chemical_formula_sum            'C10 H10 F3 N O'
_chemical_formula_weight         217.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.473(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8952(9)
_cell_length_b                   7.6628(5)
_cell_length_c                   16.6493(16)
_cell_measurement_reflns_used    4997
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.58
_cell_volume                     1006.87(16)
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/Omega-Scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4997
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .03
_exptl_crystal_size_min          .01
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0225P)²+0.0814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                1357
_reflns_number_total             2197
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja302511t_si_005.cif
_cod_data_source_block           nod327c2
_cod_database_code               4118219
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'
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
F1 F 0.23277(13) 0.05750(11) 0.44368(7) 0.0379(3) Uani 1 1 d
F2 F 0.24410(12) 0.26186(12) 0.35756(7) 0.0340(3) Uani 1 1 d
F3 F 0.39718(13) 0.27686(13) 0.50225(7) 0.0381(3) Uani 1 1 d
O1 O 0.13066(16) 0.30280(14) 0.53259(8) 0.0262(3) Uani 1 1 d
N1 N 0.08287(18) 0.51229(16) 0.41825(10) 0.0242(4) Uani 1 1 d
C1 C 0.2439(2) 0.2313(2) 0.43715(13) 0.0273(4) Uani 1 1 d
C2 C 0.0971(2) 0.3259(2) 0.44260(12) 0.0236(4) Uani 1 1 d
C3 C -0.0318(3) 0.5321(2) 0.32065(14) 0.0270(5) Uani 1 1 d
C4 C -0.1457(2) 0.3753(2) 0.30088(12) 0.0232(4) Uani 1 1 d
C5 C -0.0707(2) 0.2564(2) 0.37102(12) 0.0211(4) Uani 1 1 d
C6 C -0.1485(2) 0.0990(2) 0.37032(14) 0.0260(4) Uani 1 1 d
C7 C -0.3047(2) 0.0641(2) 0.29759(14) 0.0314(5) Uani 1 1 d
C8 C -0.3806(3) 0.1838(2) 0.22777(15) 0.0323(5) Uani 1 1 d
C9 C -0.3016(2) 0.3402(2) 0.22828(14) 0.0287(5) Uani 1 1 d
C10 C 0.2385(3) 0.6165(3) 0.45382(17) 0.0341(5) Uani 1 1 d
H1 H -0.485(2) 0.1560(19) 0.1800(13) 0.029(5) Uiso 1 1 d
H2 H -0.097(2) 0.0170(18) 0.4188(11) 0.020(4) Uiso 1 1 d
H3 H -0.093(2) 0.644(2) 0.3105(11) 0.026(4) Uiso 1 1 d
H4 H 0.207(2) 0.737(2) 0.4418(11) 0.032(5) Uiso 1 1 d
H5 H 0.309(2) 0.588(2) 0.4235(13) 0.041(5) Uiso 1 1 d
H6 H 0.302(2) 0.598(2) 0.5217(15) 0.039(6) Uiso 1 1 d
H7 H -0.360(2) -0.043(2) 0.2950(12) 0.032(5) Uiso 1 1 d
H8 H -0.354(2) 0.422(2) 0.1812(13) 0.034(5) Uiso 1 1 d
H9 H 0.029(2) 0.532(2) 0.2826(13) 0.036(5) Uiso 1 1 d
H10 H 0.052(3) 0.367(3) 0.5429(15) 0.061(7) Uiso 1 1 d
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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 O1 H10 108.9(14)
C10 N1 C2 118.15(15)
C10 N1 C3 115.67(15)
C2 N1 C3 109.32(13)
F3 C1 F1 106.16(14)
F3 C1 F2 106.77(14)
F1 C1 F2 106.59(14)
F3 C1 C2 113.98(15)
F1 C1 C2 111.52(14)
F2 C1 C2 111.36(14)
O1 C2 N1 111.49(13)
O1 C2 C5 116.47(14)
N1 C2 C5 101.30(13)
O1 C2 C1 103.72(14)
N1 C2 C1 114.12(14)
C5 C2 C1 110.17(14)
N1 C3 C4 102.24(14)
N1 C3 H3 109.0(10)
C4 C3 H3 113.2(9)
N1 C3 H9 113.3(10)
C4 C3 H9 111.2(9)
H3 C3 H9 108.0(13)
C9 C4 C5 120.53(15)
C9 C4 C3 130.42(16)
C5 C4 C3 109.05(15)
C4 C5 C6 121.32(16)
C4 C5 C2 110.45(14)
C6 C5 C2 128.24(16)
C7 C6 C5 118.07(17)
C7 C6 H2 120.6(9)
C5 C6 H2 121.3(9)
C6 C7 C8 120.65(17)
C6 C7 H7 119.9(10)
C8 C7 H7 119.4(11)
C7 C8 C9 121.11(19)
C7 C8 H1 118.3(10)
C9 C8 H1 120.6(10)
C4 C9 C8 118.32(18)
C4 C9 H8 120.8(10)
C8 C9 H8 120.9(10)
N1 C10 H4 108.0(10)
N1 C10 H5 112.0(10)
H4 C10 H5 107.4(14)
N1 C10 H6 108.0(10)
H4 C10 H6 109.0(15)
H5 C10 H6 112.3(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.3439(18)
F2 C1 1.346(2)
F3 C1 1.3385(19)
O1 C2 1.397(2)
O1 H10 0.93(2)
N1 C10 1.466(2)
N1 C2 1.4744(19)
N1 C3 1.475(2)
C1 C2 1.533(2)
C2 C5 1.513(2)
C3 C4 1.507(2)
C3 H3 0.986(15)
C3 H9 1.005(19)
C4 C9 1.382(2)
C4 C5 1.385(2)
C5 C6 1.388(2)
C6 C7 1.384(2)
C6 H2 0.957(16)
C7 C8 1.387(3)
C7 H7 0.950(15)
C8 C9 1.387(3)
C8 H1 0.928(17)
C9 H8 0.941(17)
C10 H4 0.960(16)
C10 H5 0.99(2)
C10 H6 1.01(2)
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
C10 N1 C2 O1 73.6(2)
C3 N1 C2 O1 -151.34(15)
C10 N1 C2 C5 -161.88(16)
C3 N1 C2 C5 -26.79(17)
C10 N1 C2 C1 -43.5(2)
C3 N1 C2 C1 91.56(18)
F3 C1 C2 O1 -50.39(18)
F1 C1 C2 O1 69.81(17)
F2 C1 C2 O1 -171.26(13)
F3 C1 C2 N1 71.1(2)
F1 C1 C2 N1 -168.69(14)
F2 C1 C2 N1 -49.75(19)
F3 C1 C2 C5 -175.73(13)
F1 C1 C2 C5 -55.54(19)
F2 C1 C2 C5 63.40(18)
C10 N1 C3 C4 163.66(15)
C2 N1 C3 C4 27.34(18)
N1 C3 C4 C9 162.88(18)
N1 C3 C4 C5 -16.64(19)
C9 C4 C5 C6 0.5(3)
C3 C4 C5 C6 -179.94(16)
C9 C4 C5 C2 -179.10(16)
C3 C4 C5 C2 0.5(2)
O1 C2 C5 C4 136.96(15)
N1 C2 C5 C4 15.84(18)
C1 C2 C5 C4 -105.32(16)
O1 C2 C5 C6 -42.6(2)
N1 C2 C5 C6 -163.71(17)
C1 C2 C5 C6 75.1(2)
C4 C5 C6 C7 -0.5(3)
C2 C5 C6 C7 179.01(17)
C5 C6 C7 C8 -0.1(3)
C6 C7 C8 C9 0.8(3)
C5 C4 C9 C8 0.1(3)
C3 C4 C9 C8 -179.32(18)
C7 C8 C9 C4 -0.8(3)
