Asymmetric Synthesis of Functionalized Tetrasubstituted α-Aminophosphonates through Enantioselective Aza-Henry Reaction of Phosphorylated Ketimines.
Vicario, Javier; Ortiz, Pablo; Ezpeleta, José M; Palacios, Francisco; The Journal of organic chemistry 80 (2014) 156–; doi:10.1021/jo502233m

data_4030331
_publ_section_title
;
 Asymmetric Synthesis of Functionalized Tetrasubstituted
 \a-Aminophosphonates through Enantioselective Aza-Henry Reaction of
 Phosphorylated Ketimines.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              156
_journal_paper_doi               10.1021/jo502233m
_journal_volume                  80
_journal_year                    2014
_chemical_formula_moiety         'C21 H29 N2 O7 P S'
_chemical_formula_sum            'C21 H29 N2 O7 P S'
_chemical_formula_weight         484.49
_chemical_name_systematic
;
Diisopropyl (1-((4-methylphenyl)sulfonamido)-2-nitro-1-phenylethyl)phosphonate
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                 110.4378(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.90894(19)
_cell_length_b                   15.8188(2)
_cell_length_c                   12.3797(2)
_cell_measurement_reflns_used    8920
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.2300
_cell_measurement_theta_min      3.6270
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
'L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, 
      H. Puschmann, in preparation (2013)' 
;
_diffrn_ambient_temperature      99.98(11)
_diffrn_detector_area_resol_mean 10.4023
_diffrn_measured_fraction_theta_full 0.9998
_diffrn_measured_fraction_theta_max 0.9817
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0650407000
_diffrn_orient_matrix_UB_12      -0.0835521000
_diffrn_orient_matrix_UB_13      0.0311288000
_diffrn_orient_matrix_UB_21      -0.0003642000
_diffrn_orient_matrix_UB_22      -0.0069340000
_diffrn_orient_matrix_UB_23      -0.1242641000
_diffrn_orient_matrix_UB_31      0.1094997000
_diffrn_orient_matrix_UB_32      0.0495334000
_diffrn_orient_matrix_UB_33      0.0349533000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18256
_diffrn_reflns_theta_full        74.10
_diffrn_reflns_theta_max         74.10
_diffrn_reflns_theta_min         3.65
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.234
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1024
_refine_diff_density_max         1.306
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0383
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                4234
_reflns_number_total             4739
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502233m_si_002.cif
_cod_data_source_block           a2012122_po87
_cod_depositor_comments          'Adding full bibliography for 4030331.cif.'
_cod_original_cell_volume        2368.86(6)
_cod_database_code               4030331
_cell_oxdiff_length_a            12.9062(3)
_cell_oxdiff_length_b            15.8203(4)
_cell_oxdiff_length_c            12.3788(4)
_cell_oxdiff_angle_alpha         89.976(2)
_cell_oxdiff_angle_beta          110.408(3)
_cell_oxdiff_angle_gamma         89.974(2)
_cell_oxdiff_volume              2368.86(12)
_cell_oxdiff_measurement_reflns_used 8920
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97