Mono thiomalonates as thioester enolate equivalents–enantioselective 1,4-addition reactions to nitroolefins under mild conditions.
Clerici, Paolo; Wennemers, Helma; Organic & biomolecular chemistry 10 (2012) 110–113; doi:10.1039/c1ob06638b

data_7152188
_publ_section_title
;
 Mono thiomalonates as thioester enolate equivalents--enantioselective
 1,4-addition reactions to nitroolefins under mild conditions.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              110
_journal_page_last               113
_journal_paper_doi               10.1039/c1ob06638b
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H10 Br N O, H2 O'
_chemical_formula_sum            'C10 H12 Br N O2'
_chemical_formula_weight         258.11
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8120(5)
_cell_length_b                   6.7788(6)
_cell_length_c                   25.807(2)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    123
_cell_measurement_theta_max      40
_cell_measurement_theta_min      3
_cell_volume                     1016.75(15)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            59191
_diffrn_reflns_theta_full        44.202
_diffrn_reflns_theta_max         44.202
_diffrn_reflns_theta_min         3.107
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.016
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.70
_refine_diff_density_min         -0.64
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.005(5)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0800
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         5286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0221
_refine_ls_shift/su_max          0.0016881
_refine_ls_shift/su_mean         0.0000615
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.120 0.955E-01 0.559E-01
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0381
_refine_ls_wR_factor_gt          0.0210
_refine_ls_wR_factor_ref         0.0205
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              50
_reflns_limit_l_min              0
_reflns_number_gt                5607
_reflns_number_total             8055
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.20
_oxford_diffrn_Wilson_scale      55.85
_oxford_refine_ls_r_factor_ref   0.0209
_oxford_refine_ls_scale          0.14218(8)
_oxford_reflns_number_all        8050
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            c1ob06638b.txt
_cod_data_source_block           1
_cod_original_formula_sum        'C10 H12 Br1 N1 O2'
_cod_database_code               7152188