Simple and practical direct asymmetric aldol reaction of hydroxyacetone catalyzed by 9-amino Cinchona alkaloid tartrates
Czarnecki, Paweł; Plutecka, Agnieszka; Gawroński, Jacek; Kacprzak, Karol; Green Chemistry 13 (2011) 1280–; doi:10.1039/c1gc15064b

data_7206038
_publ_section_title
;
 Simple and practical direct asymmetric aldol reaction of
 hydroxyacetone catalyzed by 9-amino Cinchona alkaloid tartrates
;
_journal_issue                   5
_journal_name_full               'Green Chemistry'
_journal_page_first              1280
_journal_paper_doi               10.1039/c1gc15064b
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H11 N O5'
_chemical_formula_sum            'C10 H11 N O5'
_chemical_formula_weight         225.20
_chemical_name_common
syn-(3S,4R)-3,4-dihydroxy-4-(4-nitrophenyl)butan-2-one
_chemical_name_systematic
;
<i>syn</i>-(3<i>S</i>,4<i>R</i>)-3,4-dihydroxy-
4-(4-nitrophenyl)butan-2-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6835(4)
_cell_length_b                   9.2616(8)
_cell_length_c                   23.4038(16)
_cell_measurement_reflns_used    6608
_cell_measurement_temperature    130.0(1)
_cell_measurement_theta_max      76.63
_cell_measurement_theta_min      3.78
_cell_volume                     1015.18(14)
_computing_cell_refinement
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.61'
_computing_data_collection
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.61'
_computing_data_reduction
'CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.61'
_computing_molecular_graphics    'ORTEP3 for Windows, 1997'
_computing_publication_material  'PLATON, 1998'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      130.0(1)
_diffrn_detector_area_resol_mean 5.2679
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_sigmaI/netI    0.0074
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7684
_diffrn_reflns_theta_full        76.63
_diffrn_reflns_theta_max         76.63
_diffrn_reflns_theta_min         3.78
_diffrn_standards_interval_count 4
_diffrn_standards_interval_time  60
_diffrn_standards_number         7733
_exptl_absorpt_coefficient_mu    1.024
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0256
_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^)+(0.0352P)^2^+0.2449P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0688
_reflns_number_gt                2053
_reflns_number_total             2060
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1gc15064b.txt
_cod_data_source_block           syn_5
_cod_original_cell_volume        1015.19(15)
_cod_database_code               7206038