Enantioselective organocatalytic oxa-Michael addition of oximes to β-CF3-β-disubstituted nitroalkenes: efficient synthesis of β-amino-α-trifluoromethyl alcohols.
Liu, Feng-Lei; Chen, Jia-Rong; Feng, Bin; Hu, Xiao-Qiang; Ye, Li-Hua; Lu, Liang-Qiu; Xiao, Wen-Jing; Organic & biomolecular chemistry 12 (2014) 1057–1060; doi:10.1039/c3ob42329h

data_7153581
_publ_section_title
;
 Enantioselective organocatalytic oxa-Michael addition of oximes to
 \b-CF3-\b-disubstituted nitroalkenes: efficient synthesis of
 \b-amino-\a-trifluoromethyl alcohols.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1057
_journal_page_last               1060
_journal_paper_doi               10.1039/c3ob42329h
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C18 H17 F3 N2 O5'
_chemical_formula_weight         398.34
_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
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_cell_angle_alpha                90.00
_cell_angle_beta                 98.175(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.293(3)
_cell_length_b                   9.873(3)
_cell_length_c                   10.265(3)
_cell_measurement_reflns_used    2624
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      70.19
_cell_measurement_theta_min      13.16
_cell_volume                     932.2(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.887
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
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_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11973
_diffrn_reflns_theta_full        70.58
_diffrn_reflns_theta_max         70.58
_diffrn_reflns_theta_min         13.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.070
_exptl_absorpt_correction_T_max  0.9005
_exptl_absorpt_correction_T_min  0.8559
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(8)
_refine_ls_extinction_coef       0.47(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   2.269
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3101
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      2.269
_refine_ls_R_factor_all          0.2612
_refine_ls_R_factor_gt           0.2246
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5764
_refine_ls_wR_factor_ref         0.6210
_reflns_number_gt                1855
_reflns_number_total             3101
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob42329h.txt
_cod_data_source_block           e:\130919a\work\t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        932.2(4)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7153581