Efficient synthesis of chiral benzofuryl β-amino alcohols via a catalytic asymmetric Henry reaction.
Chen, Wei; Zhou, Zhao-Hui; Chen, Hong-Bin; Organic & biomolecular chemistry 15 (2017) 1530–1536; doi:10.1039/c6ob02569b

data_7155461
_publ_section_title
;
 Efficient synthesis of chiral benzofuryl \b-amino alcohols via a
 catalytic asymmetric Henry reaction.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1530
_journal_page_last               1536
_journal_paper_doi               10.1039/c6ob02569b
_journal_volume                  15
_journal_year                    2017
_chemical_formula_sum            'C11 H11 N O5'
_chemical_formula_weight         237.21
_chemical_name_systematic        (S)-1-(6-Methoxybenzofuran-2-yl)-2-nitroethanol
_chemical_properties_physical    ', Heat-sensitive'
_space_group_IT_number           4
_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
_audit_update_record
;
2017-01-17 deposited with the CCDC.
2017-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.751(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.993(4)
_cell_length_b                   12.540(5)
_cell_length_c                   10.604(4)
_cell_measurement_temperature    446(2)
_cell_volume                     1036.7(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      446(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.912
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0697
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6640
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.08
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_correction_T_min  0.9761
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAc-Hexane'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2.3(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4338
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0725P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1532
_reflns_number_gt                3272
_reflns_number_total             4338
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob02569b2.cif
_cod_data_source_block           c0310m
_cod_depositor_comments
;
Adding full bibliography for 7155461--7155462.cif.

2017-11-19
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C22 H22 N2 O10'
_cod_original_formula_weight         474.42
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1036.6(8)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7155461