Catalytic asymmetric addition of beta-keto phosphonates to an activated imine‒formation of optically active functionalized phosphonate alpha-amino acid derivatives.
Kjaersgaard, Anne; Jørgensen, Karl Anker; Organic & biomolecular chemistry 3 (2005) 804–808; doi:10.1039/b416294c

data_7150036
_publ_section_title
;
 Catalytic asymmetric addition of beta-keto phosphonates to an
 activated imine--formation of optically active functionalized
 phosphonate alpha-amino acid derivatives.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              804
_journal_page_last               808
_journal_paper_doi               10.1039/b416294c
_journal_volume                  3
_journal_year                    2005
_chemical_formula_moiety         'C19 H30 N O8 P S'
_chemical_formula_sum            'C19 H30 N O8 P S'
_chemical_formula_weight         463.48
_chemical_name_systematic
;
3-(Diethoxy-phosphoryl)-3-methyl-4-oxo-2-(toluene-4-sulfonylamino)-
pentanoic acid ethyl ester
;
_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_type_scat_source           IntTabIV
_cell_angle_alpha                90.000
_cell_angle_beta                 100.647(4)
_cell_angle_gamma                90.000
_cell_formula_units_Z            2
_cell_length_a                   7.997(2)
_cell_length_b                   12.221(2)
_cell_length_c                   11.812(2)
_cell_measurement_reflns_used    7926
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.21
_cell_measurement_theta_min      2.42
_cell_volume                     1134.5(4)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
ORTEP-III (Burnett & Johnson,  1996), KRYSTAL
;
_computing_publication_material  KRYSTAL
_computing_structure_refinement  'modified ORFLS(1962), KRYSTAL'
_computing_structure_solution
;
SIR97 (Altomare et al., 1997 ), KRYSTAL
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32788
_diffrn_reflns_reduction_process 32788
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         34.40
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, 1996      '
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       box
_exptl_crystal_F_000             492
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_exptl_crystal_size_mid          0.37
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_refine_diff_density_max         1.2(1)
_refine_diff_density_min         -0.6(1)
_refine_ls_abs_structure_details
; Least squares refinement included a factor according to Rogers (1981),
refined against all 7921 non negative intensities, including 3798
Bijvoet pairs.
;
_refine_ls_abs_structure_Rogers  0.84(8)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_parameters     271
_refine_ls_number_reflns         7921
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.033
_refine_ls_shift/su_max          0.0011
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
w= 1/{[\s~cs~(F^2^)+B+(1+A)F^2^]^1/2^- |F|}^2^
where A = 0.05 and B = 0.4
;
_refine_ls_weighting_scheme      calc
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_reflns_number_gt                7921
_reflns_number_total             9477
_reflns_threshold_expression     I>0
_cod_data_source_file            b416294c.txt
_cod_data_source_block           cpd_3e
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_site_thermal_displace_type' tag value 'Uij' was replaced with
'Uani' value 30 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1134.4(4)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7150036