Catalytic asymmetric synthesis of α,β-disubstituted α,γ-diaminophosphonic acid precursors by Michael addition of α-substituted nitrophosphonates to nitroolefins.
Tripathi, Chandra Bhushan; Kayal, Satavisha; Mukherjee, Santanu; Organic letters 14 (2012) 3296–3299; doi:10.1021/ol3012666

data_1507839
_publ_section_title
;
 Catalytic asymmetric synthesis of \a,\b-disubstituted
 \a,\g-diaminophosphonic acid precursors by Michael addition of
 \a-substituted nitrophosphonates to nitroolefins.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3296
_journal_page_last               3299
_journal_paper_doi               10.1021/ol3012666
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H25 N2 O7 P'
_chemical_formula_sum            'C12 H25 N2 O7 P'
_chemical_formula_weight         340.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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_date             2012-04-16
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled 2012.03.20 svn.r2253, GUI svn.r4124)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.383(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.5051(16)
_cell_length_b                   12.370(3)
_cell_length_c                   9.944(3)
_cell_measurement_reflns_used    7746
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.08
_cell_measurement_theta_min      2.65
_cell_volume                     910.8(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker GIS'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17743
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_correction_T_min  0.9306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_coef       0.054(5)
_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   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3179
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0570P)^2^+0.0628P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                2914
_reflns_number_total             3179
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3012666_si_003.cif
_cod_data_source_block           p21_0m
_cod_depositor_comments          'Adding full bibliography for 1507839.cif.'
_cod_database_code               1507839