#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:32:36 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178953 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/82/4118218.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_4118218
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         'C11 H10 Cl F3 O2'
_chemical_formula_sum            'C11 H10 Cl F3 O2'
_chemical_formula_weight         266.64
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 109.926(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.5630(18)
_cell_length_b                   5.9491(5)
_cell_length_c                   19.7934(18)
_cell_measurement_reflns_used    5367
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.11
_cell_volume                     2276.4(3)
_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 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5367
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.362
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .06
_exptl_crystal_size_min          .02
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0479P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                1678
_reflns_number_total             2424
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja302511t_si_004.cif
_cod_data_source_block           nod362
_cod_database_code               4118218
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_refinement_flags
Cl1 Cl 0.34441(3) -0.28722(9) 0.32082(3) 0.03262(18) Uani 1 1 d .
F1 F 0.49780(6) 0.35454(19) 0.16222(6) 0.0288(3) Uani 1 1 d .
F2 F 0.52499(5) 0.05235(19) 0.11773(6) 0.0272(3) Uani 1 1 d .
F3 F 0.49913(6) 0.3530(2) 0.05406(7) 0.0325(3) Uani 1 1 d .
O1 O 0.37152(7) 0.3670(2) 0.05397(7) 0.0223(3) Uani 1 1 d .
H1 H 0.3286 0.3454 0.0374 0.033 Uiso 1 1 calc R
O2 O 0.27316(7) 0.0298(2) -0.01191(8) 0.0280(4) Uani 1 1 d .
C1 C 0.36172(10) -0.1572(4) 0.24956(11) 0.0225(5) Uani 1 1 d .
C2 C 0.33534(10) 0.0536(4) 0.22703(11) 0.0233(5) Uani 1 1 d .
H2 H 0.3079 0.1286 0.2501 0.028 Uiso 1 1 calc R
C3 C 0.34933(10) 0.1552(3) 0.17028(11) 0.0210(5) Uani 1 1 d .
H3 H 0.3316 0.3010 0.1548 0.025 Uiso 1 1 calc R
C4 C 0.38911(9) 0.0451(3) 0.13597(10) 0.0183(4) Uani 1 1 d .
C5 C 0.40574(10) 0.1597(3) 0.07448(10) 0.0198(5) Uani 1 1 d .
C6 C 0.48226(10) 0.2310(3) 0.10228(11) 0.0223(5) Uani 1 1 d .
C7 C 0.39415(10) 0.0042(3) 0.00939(10) 0.0219(5) Uani 1 1 d .
H7A H 0.4113 0.0803 -0.0258 0.026 Uiso 1 1 calc R
H7B H 0.4218 -0.1343 0.0255 0.026 Uiso 1 1 calc R
C8 C 0.31961(10) -0.0604(3) -0.02754(11) 0.0214(5) Uani 1 1 d .
C9 C 0.30571(12) -0.2378(3) -0.08425(11) 0.0280(5) Uani 1 1 d .
H9A H 0.3196 -0.3847 -0.0615 0.042 Uiso 1 1 calc R
H9B H 0.3322 -0.2049 -0.1159 0.042 Uiso 1 1 calc R
H9C H 0.2562 -0.2402 -0.1125 0.042 Uiso 1 1 calc R
C10 C 0.41457(10) -0.1679(3) 0.15964(11) 0.0232(5) Uani 1 1 d .
H10 H 0.4415 -0.2451 0.1364 0.028 Uiso 1 1 calc R
C11 C 0.40136(10) -0.2695(3) 0.21663(11) 0.0232(5) Uani 1 1 d .
H11 H 0.4194 -0.4145 0.2328 0.028 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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'
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
C5 O1 H1 109.5
C11 C1 C2 121.27(18)
C11 C1 Cl1 118.89(17)
C2 C1 Cl1 119.84(15)
C1 C2 C3 119.38(17)
C1 C2 H2 120.3
C3 C2 H2 120.3
C2 C3 C4 120.48(19)
C2 C3 H3 119.8
C4 C3 H3 119.8
C10 C4 C3 118.76(18)
C10 C4 C5 120.86(16)
C3 C4 C5 120.36(17)
O1 C5 C4 113.17(15)
O1 C5 C7 111.45(16)
C4 C5 C7 112.66(16)
O1 C5 C6 102.17(15)
C4 C5 C6 108.46(16)
C7 C5 C6 108.25(15)
F3 C6 F1 107.04(16)
F3 C6 F2 106.45(15)
F1 C6 F2 106.98(16)
F3 C6 C5 112.17(17)
F1 C6 C5 111.99(15)
F2 C6 C5 111.85(16)
C8 C7 C5 113.69(15)
C8 C7 H7A 108.8
C5 C7 H7A 108.8
C8 C7 H7B 108.8
C5 C7 H7B 108.8
H7A C7 H7B 107.7
O2 C8 C9 122.23(19)
O2 C8 C7 121.22(18)
C9 C8 C7 116.54(17)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 C4 121.08(18)
C11 C10 H10 119.5
C4 C10 H10 119.5
C1 C11 C10 119.03(19)
C1 C11 H11 120.5
C10 C11 H11 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.748(2)
F1 C6 1.338(2)
F2 C6 1.346(2)
F3 C6 1.336(2)
O1 C5 1.410(2)
O1 H1 0.8400
O2 C8 1.224(2)
C1 C11 1.378(3)
C1 C2 1.379(3)
C2 C3 1.389(3)
C2 H2 0.9500
C3 C4 1.392(2)
C3 H3 0.9500
C4 C10 1.390(3)
C4 C5 1.532(3)
C5 C7 1.537(3)
C5 C6 1.539(3)
C7 C8 1.506(3)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.496(3)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 C11 1.386(3)
C10 H10 0.9500
C11 H11 0.9500
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
C11 C1 C2 C3 -0.4(3)
Cl1 C1 C2 C3 -179.91(15)
C1 C2 C3 C4 0.5(3)
C2 C3 C4 C10 -0.1(3)
C2 C3 C4 C5 -178.68(17)
C10 C4 C5 O1 175.50(17)
C3 C4 C5 O1 -5.9(3)
C10 C4 C5 C7 47.9(2)
C3 C4 C5 C7 -133.51(18)
C10 C4 C5 C6 -71.9(2)
C3 C4 C5 C6 106.7(2)
O1 C5 C6 F3 -53.75(19)
C4 C5 C6 F3 -173.51(15)
C7 C5 C6 F3 64.0(2)
O1 C5 C6 F1 66.65(19)
C4 C5 C6 F1 -53.1(2)
C7 C5 C6 F1 -175.64(15)
O1 C5 C6 F2 -173.27(14)
C4 C5 C6 F2 67.0(2)
C7 C5 C6 F2 -55.6(2)
O1 C5 C7 C8 -62.8(2)
C4 C5 C7 C8 65.6(2)
C6 C5 C7 C8 -174.44(17)
C5 C7 C8 O2 9.4(3)
C5 C7 C8 C9 -171.17(17)
C3 C4 C10 C11 -0.5(3)
C5 C4 C10 C11 178.08(18)
C2 C1 C11 C10 -0.2(3)
Cl1 C1 C11 C10 179.33(15)
C4 C10 C11 C1 0.7(3)
