Stereoselectivity of the Honda-Reformatsky Reaction in Reactions with Ethyl Bromodifluoroacetate with α-Oxygenated Sulfinylimines.
Fontenelle, Clément Q; Conroy, Matthew; Light, Mark; Poisson, Thomas; Pannecoucke, Xavier; Linclau, Bruno; The Journal of organic chemistry 79 (2014) 4186–4195; doi:10.1021/jo500396p

data_4029317
_publ_section_title
;
 Stereoselectivity of the Honda-Reformatsky Reaction in Reactions with
 Ethyl Bromodifluoroacetate with \a-Oxygenated Sulfinylimines.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4186
_journal_page_last               4195
_journal_paper_doi               10.1021/jo500396p
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
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_chemical_formula_sum            'C14 H25 F2 N O5 S'
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_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
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_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.329(6)
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_cell_length_c                   23.430(16)
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_cell_measurement_temperature    100(2)
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_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
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CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
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_computing_molecular_graphics
;
Images generated using CrystalMaker: a crystal and molecular 
structures program for Mac and Windows. CrystalMaker Software Ltd, 
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'
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_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
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_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
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;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            Colourless
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_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.056
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;
 Flack x determined using 1164 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.10(5)
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
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_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0555
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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;
 w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+0.0175P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
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_reflns_Friedel_fraction_full    0.960
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_reflns_number_gt                3650
_reflns_number_total             4090
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo500396p_si_002.cif
_cod_data_source_block           2013sot0002
_cod_depositor_comments
'Adding full bibliography for 4029315--4029317.cif.'
_cod_database_code               4029317
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.968
_shelxl_version_number           2012-9
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