Acetylphosphonate as a surrogate of acetate or acetamide in organocatalyzed enantioselective aldol reactions.
Guang, Jie; Guo, Qunsheng; Zhao, John Cong-Gui; Organic letters 14 (2012) 3174–3177; doi:10.1021/ol301270w

data_1507843
_publ_section_title
;
 Acetylphosphonate as a surrogate of acetate or acetamide in
 organocatalyzed enantioselective aldol reactions.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3174
_journal_page_last               3177
_journal_paper_doi               10.1021/ol301270w
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H16 Br N O4'
_chemical_formula_sum            'C18 H16 Br N O4'
_chemical_formula_weight         390.23
_chemical_name_systematic
; 
(R)-Methyl-2-(1-benzyl-7-bromo-3-hydroxy-2-oxoindolin-3-yl)acetate 
;
_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_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                 93.600(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5624(10)
_cell_length_b                   8.3375(6)
_cell_length_c                   10.6822(11)
_cell_measurement_reflns_used    5461
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     849.97(14)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      98(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4993
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.10
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.439
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1264 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.021(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2951
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0235
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0120P)^2^+0.0800P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0587
_reflns_number_gt                2842
_reflns_number_total             2951
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301270w_si_002.cif
_cod_data_source_block           mbbhoa
_cod_depositor_comments
'Adding full bibliography for 1507843--1507844.cif.'
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1507843