#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/33/1503331.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_1503331
loop_
_publ_author_name
'Aikawa, Kohsuke'
'Hioki, Yūta'
'Mikami, Koichi'
_publ_section_title
;
 Highly enantioselective alkynylation of trifluoropyruvate with
 alkynylsilanes catalyzed by the BINAP-Pd complex: access to
 α-trifluoromethyl-substituted tertiary alcohols.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5716
_journal_page_last               5719
_journal_paper_doi               10.1021/ol102541s
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C24 H22 Cl2 F3 N O3'
_chemical_formula_weight         500.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 112.318(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.899(6)
_cell_length_b                   6.511(3)
_cell_length_c                   15.349(8)
_cell_measurement_reflns_used    1851
_cell_measurement_temperature    93
_cell_measurement_theta_max      25.66
_cell_measurement_theta_min      2.61
_cell_volume                     1192.5(10)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0870
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6622
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_correction_T_min  0.8958
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.468
_refine_diff_density_min         -1.098
_refine_diff_density_rms         0.138
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4640
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0962
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1602P)²+4.2746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2845
_refine_ls_wR_factor_ref         0.3041
_reflns_number_gt                3459
_reflns_number_total             4640
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol102541s_si_002.cif
_cod_data_source_block           090126_1320_0
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1192.4(10)
_cod_original_sg_symbol_H-M      'P2(1)   '
_cod_database_code               1503331
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
C1 C 0.1885(7) 1.2667(12) 0.9317(5) 0.0231(16) Uani 1 1 d .
H1A H 0.2557 1.2848 0.9172 0.035 Uiso 1 1 calc R
H1B H 0.2080 1.2855 0.9994 0.035 Uiso 1 1 calc R
H1C H 0.1320 1.3684 0.8968 0.035 Uiso 1 1 calc R
C2 C 0.1419(6) 1.0523(11) 0.9033(5) 0.0151(14) Uani 1 1 d .
H2A H 0.1189 1.0397 0.8335 0.018 Uiso 1 1 calc R
C3 C 0.2293(6) 0.8883(10) 0.9494(4) 0.0150(14) Uani 1 1 d .
C4 C 0.2497(6) 0.8196(13) 1.0405(5) 0.0197(15) Uani 1 1 d .
H4A H 0.2041 0.8684 1.0723 0.024 Uiso 1 1 calc R
C5 C 0.3361(6) 0.6799(12) 1.0862(5) 0.0190(15) Uani 1 1 d .
H5A H 0.3489 0.6376 1.1487 0.023 Uiso 1 1 calc R
C6 C 0.4033(6) 0.6025(11) 1.0414(5) 0.0200(15) Uani 1 1 d .
H6A H 0.4613 0.5073 1.0726 0.024 Uiso 1 1 calc R
C7 C 0.3838(6) 0.6678(11) 0.9483(5) 0.0165(14) Uani 1 1 d .
C8 C 0.2988(6) 0.8152(11) 0.9030(4) 0.0149(13) Uani 1 1 d .
C9 C 0.2872(6) 0.8822(12) 0.8110(5) 0.0217(17) Uani 1 1 d .
H9A H 0.2323 0.9828 0.7796 0.026 Uiso 1 1 calc R
C10 C 0.3536(7) 0.8040(14) 0.7675(5) 0.0257(17) Uani 1 1 d .
H10A H 0.3450 0.8520 0.7067 0.031 Uiso 1 1 calc R
C11 C 0.4349(7) 0.6522(15) 0.8124(5) 0.0267(17) Uani 1 1 d .
H11A H 0.4779 0.5941 0.7803 0.032 Uiso 1 1 calc R
C12 C 0.4517(6) 0.5889(12) 0.9014(6) 0.0222(16) Uani 1 1 d .
H12A H 0.5090 0.4918 0.9322 0.027 Uiso 1 1 calc R
C13 C 0.8990(6) 0.5237(11) 0.8157(4) 0.0125(13) Uani 1 1 d .
C14 C 0.8301(6) 0.6404(12) 0.7209(4) 0.0166(14) Uani 1 1 d .
C15 C 0.7418(6) 0.7683(13) 0.7375(5) 0.0238(17) Uani 1 1 d .
C16 C 0.9023(6) 0.7727(11) 0.6914(4) 0.0175(14) Uani 1 1 d .
C17 C 0.9559(6) 0.8832(11) 0.6627(4) 0.0177(15) Uani 1 1 d .
C18 C 1.0250(6) 1.0186(13) 0.6337(5) 0.0182(15) Uani 1 1 d .
C19 C 1.0813(6) 0.9468(12) 0.5761(4) 0.0180(15) Uani 1 1 d .
H19A H 1.0698 0.8100 0.5529 0.022 Uiso 1 1 calc R
C20 C 1.1516(7) 1.0731(14) 0.5542(5) 0.0271(18) Uani 1 1 d .
H20A H 1.1874 1.0251 0.5142 0.032 Uiso 1 1 calc R
C21 C 1.1719(7) 1.2753(13) 0.5902(6) 0.0258(17) Uani 1 1 d .
H21A H 1.2234 1.3611 0.5766 0.031 Uiso 1 1 calc R
C22 C 1.1168(7) 1.3467(13) 0.6449(5) 0.0251(17) Uani 1 1 d .
H22A H 1.1292 1.4835 0.6681 0.030 Uiso 1 1 calc R
C23 C 1.0431(7) 1.2210(12) 0.6666(5) 0.0227(17) Uani 1 1 d .
H23A H 1.0047 1.2726 0.7041 0.027 Uiso 1 1 calc R
C24 C 0.4799(10) 0.449(2) 0.5600(8) 0.053(3) Uani 1 1 d .
H24A H 0.4690 0.3968 0.4965 0.064 Uiso 1 1 calc R
H24B H 0.5557 0.5100 0.5873 0.064 Uiso 1 1 calc R
Cl1 Cl 0.3798(3) 0.6427(5) 0.5485(2) 0.0568(8) Uani 1 1 d .
Cl2 Cl 0.4735(3) 0.2440(5) 0.6293(3) 0.0690(10) Uani 1 1 d .
F1 F 0.7859(4) 0.9280(7) 0.7968(4) 0.0308(11) Uani 1 1 d .
F2 F 0.6817(4) 0.6583(9) 0.7773(3) 0.0322(11) Uani 1 1 d .
F3 F 0.6686(4) 0.8492(9) 0.6576(4) 0.0379(13) Uani 1 1 d .
H11N H 0.064(5) 1.071(11) 0.9857(19) 0.004(11) Uiso 1 1 d D
H12N H -0.010(5) 1.128(8) 0.898(4) 0.004(11) Uiso 1 1 d D
H11O H 0.995(7) 0.600(14) 0.950(6) 0.02(2) Uiso 1 1 d .
N1 N 0.0383(5) 1.0254(9) 0.9259(4) 0.0133(11) Uani 1 1 d D
O1 O 0.9480(4) 0.6277(9) 0.8879(3) 0.0188(11) Uani 1 1 d .
O2 O 0.8962(5) 0.3333(8) 0.8085(3) 0.0203(11) Uani 1 1 d .
O3 O 0.7719(5) 0.4940(9) 0.6518(3) 0.0256(13) Uani 1 1 d .
H3A H 0.7349 0.5543 0.6010 0.038 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 C3 112.1(6)
N1 C2 C1 109.2(6)
C3 C2 C1 111.7(6)
N1 C2 H2A 107.9
C3 C2 H2A 107.9
C1 C2 H2A 107.9
C4 C3 C8 118.7(6)
C4 C3 C2 121.1(6)
C8 C3 C2 120.0(6)
C3 C4 C5 121.3(7)
C3 C4 H4A 119.3
C5 C4 H4A 119.3
C6 C5 C4 121.0(6)
C6 C5 H5A 119.5
C4 C5 H5A 119.5
C5 C6 C7 119.0(7)
C5 C6 H6A 120.5
C7 C6 H6A 120.5
C6 C7 C8 120.1(6)
C6 C7 C12 119.6(7)
C8 C7 C12 120.3(6)
C3 C8 C7 119.8(6)
C3 C8 C9 122.8(6)
C7 C8 C9 117.4(6)
C10 C9 C8 121.2(7)
C10 C9 H9A 119.4
C8 C9 H9A 119.4
C9 C10 C11 120.5(7)
C9 C10 H10A 119.8
C11 C10 H10A 119.8
C12 C11 C10 120.4(7)
C12 C11 H11A 119.8
C10 C11 H11A 119.8
C11 C12 C7 120.1(7)
C11 C12 H12A 119.9
C7 C12 H12A 119.9
O2 C13 O1 127.5(6)
O2 C13 C14 114.2(6)
O1 C13 C14 118.4(6)
O3 C14 C16 112.7(5)
O3 C14 C15 106.2(6)
C16 C14 C15 109.8(6)
O3 C14 C13 108.7(6)
C16 C14 C13 111.5(6)
C15 C14 C13 107.7(5)
F3 C15 F2 107.1(6)
F3 C15 F1 106.4(7)
F2 C15 F1 105.6(6)
F3 C15 C14 112.1(6)
F2 C15 C14 112.4(6)
F1 C15 C14 112.7(6)
C17 C16 C14 176.2(8)
C16 C17 C18 176.6(7)
C23 C18 C19 118.7(7)
C23 C18 C17 120.2(6)
C19 C18 C17 120.9(7)
C20 C19 C18 120.2(7)
C20 C19 H19A 119.9
C18 C19 H19A 119.9
C19 C20 C21 120.6(7)
C19 C20 H20A 119.7
C21 C20 H20A 119.7
C22 C21 C20 119.6(8)
C22 C21 H21A 120.2
C20 C21 H21A 120.2
C21 C22 C23 120.6(8)
C21 C22 H22A 119.7
C23 C22 H22A 119.7
C22 C23 C18 120.3(7)
C22 C23 H23A 119.9
C18 C23 H23A 119.9
Cl2 C24 Cl1 114.1(6)
Cl2 C24 H24A 108.7
Cl1 C24 H24A 108.7
Cl2 C24 H24B 108.7
Cl1 C24 H24B 108.7
H24A C24 H24B 107.6
C2 N1 H11N 101(5)
C2 N1 H12N 108(5)
H11N N1 H12N 99(6)
C13 O1 H11O 136(6)
C14 O3 H3A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.517(10)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 N1 1.514(9)
C2 C3 1.519(10)
C2 H2A 1.0000
C3 C4 1.395(9)
C3 C8 1.421(10)
C4 C5 1.403(11)
C4 H4A 0.9500
C5 C6 1.389(11)
C5 H5A 0.9500
C6 C7 1.420(9)
C6 H6A 0.9500
C7 C8 1.423(10)
C7 C12 1.424(10)
C8 C9 1.430(9)
C9 C10 1.370(11)
C9 H9A 0.9500
C10 C11 1.415(12)
C10 H10A 0.9500
C11 C12 1.363(11)
C11 H11A 0.9500
C12 H12A 0.9500
C13 O2 1.244(9)
C13 O1 1.246(9)
C13 C14 1.582(9)
C14 O3 1.412(9)
C14 C16 1.461(10)
C14 C15 1.509(11)
C15 F3 1.340(9)
C15 F2 1.358(9)
C15 F1 1.356(10)
C16 C17 1.191(10)
C17 C18 1.440(11)
C18 C23 1.398(11)
C18 C19 1.420(9)
C19 C20 1.357(11)
C19 H19A 0.9500
C20 C21 1.413(12)
C20 H20A 0.9500
C21 C22 1.371(12)
C21 H21A 0.9500
C22 C23 1.389(12)
C22 H22A 0.9500
C23 H23A 0.9500
C24 Cl2 1.727(13)
C24 Cl1 1.766(13)
C24 H24A 0.9900
C24 H24B 0.9900
N1 H11N 0.900(10)
N1 H12N 0.899(10)
O1 H11O 0.94(9)
O3 H3A 0.8400
