Enantio- and diastereoselective addition of cyclohexyl Meldrum's acid to β- and α,β-disubstituted nitroalkenes via N-sulfinyl urea catalysis
Kimmel, Kyle L.; Weaver, Jimmie D.; Ellman, Jonathan A.; Chemical Science 3 (2012) 121–; doi:10.1039/c1sc00441g

data_1515268
_publ_section_title
;
 Enantio- and diastereoselective addition of cyclohexyl Meldrum's acid to
 \b- and \a,\b-disubstituted nitroalkenes via N-sulfinyl urea catalysis
;
_journal_issue                   1
_journal_name_full               'Chemical Science'
_journal_page_first              121
_journal_paper_doi               10.1039/c1sc00441g
_journal_volume                  3
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'O6 N C18 H21'
_chemical_formula_sum            'C18 H21 N O6'
_chemical_formula_weight         347.37
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_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
_cell_angle_alpha                102.179(7)
_cell_angle_beta                 107.108(8)
_cell_angle_gamma                93.227(7)
_cell_formula_units_Z            4
_cell_length_a                   11.3125(2)
_cell_length_b                   12.0218(2)
_cell_length_c                   13.7304(10)
_cell_measurement_reflns_used    11114
_cell_measurement_temperature    93
_cell_measurement_theta_max      65.89
_cell_measurement_theta_min      6.88
_cell_volume                     1730.44(17)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 11.111
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.608
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11758
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         65.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             736.00
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.300
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 2000 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.04(20)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     901
_refine_ls_number_reflns         7325
_refine_ls_number_restraints     3
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1031P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1611
_reflns_number_gt                6393
_reflns_number_total             7325
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c1sc00441g.txt
_cod_data_source_block           '_kk02'
_cod_original_cell_volume        1730.44(16)
_cod_original_formula_sum        'O6 N C18 H21'
_cod_database_code               1515268