The squaramide-catalyzed asymmetric Michael/cyclization tandem reaction for the synthesis of chiral trifluoromethylated hydroxyimino tetrahydrobenzofuranones.
Liu, Wei; Lai, Xiaoyan; Zha, Gaofeng; Xu, Yan; Sun, Panpan; Xia, Tao; Shen, Yongcun; Organic & biomolecular chemistry 14 (2016) 3603–3607; doi:10.1039/c6ob00119j

data_7155017
_publ_section_title
;
 The squaramide-catalyzed asymmetric Michael/cyclization tandem reaction
 for the synthesis of chiral trifluoromethylated hydroxyimino
 tetrahydrobenzofuranones.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3603
_journal_page_last               3607
_journal_paper_doi               10.1039/c6ob00119j
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration R
_chemical_formula_sum            'C15 H11 F4 N O3'
_chemical_formula_weight         329.25
_chemical_name_systematic
(R,Z)-3-(4-fluorophenyl)-2-(hydroxyimino)-3-(trifluoromethyl)-3,5,6,7-tetrahydrobenzofuran-4(2H)-one
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc1kl6kx
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-01-15 deposited with the CCDC.
2016-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7967(4)
_cell_length_b                   9.2428(4)
_cell_length_c                   17.2636(8)
_cell_measurement_reflns_used    3309
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0200
_cell_measurement_theta_min      5.1130
_cell_volume                     1403.64(11)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8522
_diffrn_reflns_theta_full        66.45
_diffrn_reflns_theta_max         66.45
_diffrn_reflns_theta_min         5.12
_exptl_absorpt_coefficient_mu    1.263
_exptl_absorpt_correction_T_max  0.6880
_exptl_absorpt_correction_T_min  0.6190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.0143(6)
_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   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0370
_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/[\s^2^(Fo^2^)+(0.0355P)^2^+0.3309P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0924
_reflns_number_gt                2166
_reflns_number_total             2477
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob00119j2.cif
_cod_data_source_block           160103a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155017.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7155017