Catalytic Aldol-Cyclization Cascade of 3-Isothiocyanato Oxindoles with α-Ketophosphonates for the Enantioselective Synthesis of β-Amino-α-hydroxyphosphonates.
Kayal, Satavisha; Mukherjee, Santanu; Organic letters 17 (2015) 5508–5511; doi:10.1021/acs.orglett.5b02929

data_1555432
_publ_section_title
;
 Catalytic Aldol-Cyclization Cascade of 3-Isothiocyanato Oxindoles with
 \a-Ketophosphonates for the Enantioselective Synthesis of
 \b-Amino-\a-hydroxyphosphonates.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5508
_journal_page_last               5511
_journal_paper_doi               10.1021/acs.orglett.5b02929
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_sum            'C25.5 H31 Cl1.5 N2 O5 P S'
_chemical_formula_weight         561.72
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 102.411(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5437(9)
_cell_length_b                   13.0346(8)
_cell_length_c                   16.0277(11)
_cell_measurement_temperature    273(2)
_cell_volume                     2763.4(3)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            109602
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.452
_diffrn_reflns_theta_min         3.036
_exptl_absorpt_coefficient_mu    0.358
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       Block
_exptl_crystal_F_000             1178
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         11312
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0834P)^2^+0.9557P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1170
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                10716
_reflns_number_total             11312
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02929_si_003.cif
_cod_data_source_block           3af
_cod_depositor_comments
;

2022-11-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C51 H62 Cl3 N4 O10 P2 S2'
_cod_original_formula_weight         1123.45
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555432
_shelxl_version_number           2013-4
_shelx_res_checksum              29769
_shelx_hkl_checksum              42715