Highly enantioselective synthesis of nitrocyclopropanes via organocatalytic conjugate addition of bromomalonate to alpha,beta-unsaturated nitroalkenes.
Xuan, Yi-Ning; Nie, Shao-Zhen; Dong, Li-Ting; Zhang, Jun-Min; Yan, Ming; Organic letters 11 (2009) 1583–1586; doi:10.1021/ol900227j

data_1503827
_publ_section_title
;
 Highly enantioselective synthesis of nitrocyclopropanes via
 organocatalytic conjugate addition of bromomalonate to
 alpha,beta-unsaturated nitroalkenes.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1583
_journal_page_last               1586
_journal_paper_doi               10.1021/ol900227j
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H12 N2 O8'
_chemical_formula_sum            'C13 H12 N2 O8'
_chemical_formula_weight         324.25
_chemical_name_systematic
;
(2S,3R)-dimethyl 2-nitro-3-(4-nitrophenyl)cyclopropane-1,1-dicarboxylate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.9430(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.58810(10)
_cell_length_b                   12.18360(10)
_cell_length_c                   8.37150(10)
_cell_measurement_reflns_used    10123
_cell_measurement_temperature    423(2)
_cell_measurement_theta_max      70.8732
_cell_measurement_theta_min      3.6183
_cell_volume                     717.880(15)
_computing_cell_refinement
;
 CrysAlis RED, Oxford Diffraction Ltd.,
 Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
 (compiled Jun 10 2008,16:49:55)
;
_computing_data_collection
;
 CrysAlis CCD, Oxford Diffraction Ltd.,
 Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
 (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction
;
 CrysAlis RED, Oxford Diffraction Ltd.,
 Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
 (compiled Jun 10 2008,16:49:55)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      423(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  XCALIBUR2
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10204
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         5.70
_exptl_absorpt_coefficient_mu    1.102
_exptl_absorpt_correction_T_max  0.8978
_exptl_absorpt_correction_T_min  0.7334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlis RED, Oxford Diffraction Ltd.,
 Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
 (compiled Jun 10 2008,16:49:55)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(14)
_refine_ls_extinction_coef       0.0161(12)
_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   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2351
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0230
_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^)+(0.0354P)^2^+0.1354P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0625
_reflns_number_gt                2318
_reflns_number_total             2351
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900227j_si_001.cif
_cod_data_source_block           XYN34
_cod_original_cell_volume        717.880(14)
_cod_database_code               1503827