#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/71/7117185.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_7117185
loop_
_publ_author_name
'Ai-Jie Cai'
'Yan Zheng'
'Jun-An Ma'
_publ_section_title
;
 Copper-triggered three-component reaction of CF3CHN2, nitriles, and
 aldehydes: highly diastereoselective synthesis of CF3-substituted
 oxazolines and vicinal amino alcohols
;
_journal_name_full               Chem.Commun.
_journal_page_first              8946
_journal_paper_doi               10.1039/c5cc02749G
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C11 H9 F3 N2 O3'
_chemical_formula_weight         274.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-01-05 deposited with the CCDC.
2015-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                102.598(13)
_cell_angle_beta                 92.769(13)
_cell_angle_gamma                110.155(13)
_cell_formula_units_Z            2
_cell_length_a                   5.736(3)
_cell_length_b                   7.686(5)
_cell_length_c                   15.026(9)
_cell_measurement_reflns_used    873
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.679
_cell_measurement_theta_min      2.803
_cell_volume                     601.4(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3440
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.40
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.9724
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0982
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2771
_refine_ls_wR_factor_ref         0.3071
_reflns_number_gt                1411
_reflns_number_total             2109
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc02749g2.cif
_cod_data_source_block           ch
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'NONE' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7117185
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4477(7) 1.3989(4) 0.1851(3) 0.1193(13) Uani 1 1 d . . .
F2 F 0.1337(6) 1.2177(5) 0.0856(2) 0.0970(11) Uani 1 1 d . . .
F3 F 0.0758(8) 1.3240(5) 0.2223(3) 0.1189(14) Uani 1 1 d . . .
O1 O 0.0276(5) 0.7698(4) 0.11887(17) 0.0632(9) Uani 1 1 d . . .
O2 O -0.1980(9) 0.6191(6) 0.5497(3) 0.1039(14) Uani 1 1 d . . .
O3 O -0.4193(7) 0.7932(6) 0.5613(2) 0.0944(12) Uani 1 1 d . . .
N1 N 0.4028(6) 1.0078(5) 0.1430(2) 0.0588(9) Uani 1 1 d . . .
N2 N -0.2817(7) 0.7232(6) 0.5212(3) 0.0695(11) Uani 1 1 d . . .
C1 C 0.2284(11) 1.2570(7) 0.1741(3) 0.0769(13) Uani 1 1 d . . .
C2 C 0.2477(7) 1.0851(6) 0.2003(3) 0.0557(10) Uani 1 1 d . . .
H2 H 0.3209 1.1211 0.2650 0.067 Uiso 1 1 calc R . .
C3 C 0.2669(7) 0.8380(6) 0.1011(3) 0.0550(10) Uani 1 1 d . . .
C4 C 0.3412(9) 0.7058(7) 0.0330(3) 0.0761(13) Uani 1 1 d . . .
H4A H 0.2484 0.6812 -0.0261 0.114 Uiso 1 1 calc R . .
H4B H 0.3067 0.5878 0.0509 0.114 Uiso 1 1 calc R . .
H4C H 0.5172 0.7619 0.0298 0.114 Uiso 1 1 calc R . .
C5 C -0.0101(7) 0.9198(6) 0.1857(2) 0.0533(10) Uani 1 1 d . . .
H5 H -0.1392 0.9571 0.1589 0.064 Uiso 1 1 calc R . .
C6 C -0.0864(6) 0.8586(5) 0.2711(2) 0.0492(9) Uani 1 1 d . . .
C7 C 0.0006(8) 0.7351(6) 0.3039(3) 0.0670(12) Uani 1 1 d . . .
H7 H 0.1041 0.6830 0.2709 0.080 Uiso 1 1 calc R . .
C8 C -0.0645(9) 0.6874(7) 0.3857(3) 0.0722(13) Uani 1 1 d . . .
H8 H -0.0060 0.6040 0.4077 0.087 Uiso 1 1 calc R . .
C9 C -0.2165(7) 0.7662(5) 0.4328(2) 0.0551(10) Uani 1 1 d . . .
C10 C -0.3047(8) 0.8897(7) 0.4020(3) 0.0710(13) Uani 1 1 d . . .
H10 H -0.4078 0.9419 0.4353 0.085 Uiso 1 1 calc R . .
C11 C -0.2381(8) 0.9352(7) 0.3208(3) 0.0684(12) Uani 1 1 d . . .
H11 H -0.2968 1.0191 0.2993 0.082 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'
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
C3 O1 C5 107.4(3) . .
C3 N1 C2 106.9(3) . .
O2 N2 O3 123.2(4) . .
O2 N2 C9 118.5(4) . .
O3 N2 C9 118.3(4) . .
F1 C1 F3 107.9(4) . .
F1 C1 F2 105.8(4) . .
F3 C1 F2 105.6(4) . .
F1 C1 C2 113.1(4) . .
F3 C1 C2 111.6(4) . .
F2 C1 C2 112.3(4) . .
N1 C2 C1 110.6(3) . .
N1 C2 C5 105.6(3) . .
C1 C2 C5 112.3(4) . .
N1 C2 H2 109.4 . .
C1 C2 H2 109.4 . .
C5 C2 H2 109.4 . .
N1 C3 O1 117.9(3) . .
N1 C3 C4 126.4(4) . .
O1 C3 C4 115.7(3) . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
O1 C5 C6 111.7(3) . .
O1 C5 C2 102.2(3) . .
C6 C5 C2 114.3(3) . .
O1 C5 H5 109.5 . .
C6 C5 H5 109.5 . .
C2 C5 H5 109.5 . .
C11 C6 C7 119.0(4) . .
C11 C6 C5 118.9(4) . .
C7 C6 C5 122.1(3) . .
C6 C7 C8 120.8(4) . .
C6 C7 H7 119.6 . .
C8 C7 H7 119.6 . .
C9 C8 C7 118.4(4) . .
C9 C8 H8 120.8 . .
C7 C8 H8 120.8 . .
C8 C9 C10 122.0(4) . .
C8 C9 N2 119.5(4) . .
C10 C9 N2 118.4(4) . .
C9 C10 C11 118.7(4) . .
C9 C10 H10 120.6 . .
C11 C10 H10 120.6 . .
C6 C11 C10 121.1(4) . .
C6 C11 H11 119.4 . .
C10 C11 H11 119.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C1 1.325(6) .
F2 C1 1.341(6) .
F3 C1 1.329(6) .
O1 C3 1.353(5) .
O1 C5 1.440(5) .
O2 N2 1.204(5) .
O3 N2 1.213(5) .
N1 C3 1.265(5) .
N1 C2 1.450(5) .
N2 C9 1.472(5) .
C1 C2 1.495(6) .
C2 C5 1.549(6) .
C2 H2 0.9800 .
C3 C4 1.466(6) .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C5 C6 1.495(5) .
C5 H5 0.9800 .
C6 C11 1.373(5) .
C6 C7 1.379(6) .
C7 C8 1.389(6) .
C7 H7 0.9300 .
C8 C9 1.366(6) .
C8 H8 0.9300 .
C9 C10 1.368(6) .
C10 C11 1.378(6) .
C10 H10 0.9300 .
C11 H11 0.9300 .
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
C3 N1 C2 C1 -119.7(4) . . . .
C3 N1 C2 C5 2.0(4) . . . .
F1 C1 C2 N1 -61.5(5) . . . .
F3 C1 C2 N1 176.5(4) . . . .
F2 C1 C2 N1 58.1(5) . . . .
F1 C1 C2 C5 -179.2(4) . . . .
F3 C1 C2 C5 58.9(5) . . . .
F2 C1 C2 C5 -59.5(5) . . . .
C2 N1 C3 O1 -1.2(5) . . . .
C2 N1 C3 C4 177.8(4) . . . .
C5 O1 C3 N1 -0.1(5) . . . .
C5 O1 C3 C4 -179.3(4) . . . .
C3 O1 C5 C6 -121.2(3) . . . .
C3 O1 C5 C2 1.3(4) . . . .
N1 C2 C5 O1 -2.0(4) . . . .
C1 C2 C5 O1 118.6(4) . . . .
N1 C2 C5 C6 118.8(3) . . . .
C1 C2 C5 C6 -120.6(4) . . . .
O1 C5 C6 C11 -149.6(4) . . . .
C2 C5 C6 C11 95.1(4) . . . .
O1 C5 C6 C7 33.7(5) . . . .
C2 C5 C6 C7 -81.7(5) . . . .
C11 C6 C7 C8 0.3(7) . . . .
C5 C6 C7 C8 177.1(4) . . . .
C6 C7 C8 C9 -0.1(7) . . . .
C7 C8 C9 C10 -0.1(7) . . . .
C7 C8 C9 N2 -178.0(4) . . . .
O2 N2 C9 C8 0.1(6) . . . .
O3 N2 C9 C8 -179.2(4) . . . .
O2 N2 C9 C10 -177.8(4) . . . .
O3 N2 C9 C10 2.9(6) . . . .
C8 C9 C10 C11 0.1(7) . . . .
N2 C9 C10 C11 178.0(4) . . . .
C7 C6 C11 C10 -0.3(7) . . . .
C5 C6 C11 C10 -177.2(4) . . . .
C9 C10 C11 C6 0.1(7) . . . .
