Stereoselective Synthesis of Highly Functionalized Nitrocyclopropanes via Organocatalyic Conjugate Addition to Nitroalkenes
McCooey, Séamus H.; McCabe, Thomas; Connon, Stephen J.; The Journal of Organic Chemistry 71 (2006) 7494–7497; doi:10.1021/jo0613838

data_4028895
_publ_contact_author             'Stephen J Connon'
_publ_section_title
;
 Stereoselective Synthesis of Highly Functionalized Nitrocyclopropanes via
 Organocatalyic Conjugate Addition to Nitroalkenes
;
_journal_issue                   19
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              7494
_journal_page_last               7497
_journal_paper_doi               10.1021/jo0613838
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C22.67 H20 N1.33 O8'
_chemical_formula_weight         439.07
_chemical_melting_point          417
_chemical_name_common
'2-Naphthalen-1-yl-3-nitro-cyclopropane-1,1-dicarboxylic acid dimethyl ester'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 104.353(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            3
_cell_length_a                   12.609(2)
_cell_length_b                   14.633(2)
_cell_length_c                   8.6593(14)
_cell_measurement_temperature    571(2)
_cell_volume                     1547.8(4)
_computing_cell_refinement       'Bruker Smart Apex'
_computing_data_collection       'Bruker Smart Apex'
_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      571(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12919
_diffrn_reflns_theta_full        28.41
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.848835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+0.3247P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1203
_reflns_number_gt                3238
_reflns_number_total             3796
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0613838sup1.cif
_cod_data_source_block           smc302bm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '417k' was changed to '417' - the
value should be numeric and without a unit
designator.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1547.9(4)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4028895
_cod_duplicate_entry 4021969