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_7155462
_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            'C10 H8 Cl N O4'
_chemical_formula_weight         241.62
_chemical_name_common            'Chloride substitute'
_chemical_name_systematic        (S)-1-(5-Chlorobenzofuran-2-yl)-2-nitroethanol
_chemical_properties_physical    ', Heat-sensitive'
_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
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5571(2)
_cell_length_b                   5.6305(2)
_cell_length_c                   32.3624(10)
_cell_measurement_reflns_used    35
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      36
_cell_measurement_theta_min      34
_cell_volume                     1012.60(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Gemini Oxford Diffractometer'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            11073
_diffrn_reflns_theta_full        62.12
_diffrn_reflns_theta_max         62.12
_diffrn_reflns_theta_min         5.47
_exptl_absorpt_coefficient_mu    3.371
_exptl_absorpt_correction_T_max  0.7742
_exptl_absorpt_correction_T_min  0.5521
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_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          0.08
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1590
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0217
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0378P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0544
_refine_ls_wR_factor_ref         0.0549
_reflns_number_gt                1505
_reflns_number_total             1590
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob02569b2.cif
_cod_data_source_block           sad
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155461--7155462.cif.
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_cod_database_code               7155462