Catalytic enantioselective Henry reaction of α-keto esters, 2-acylpyridines and 2-acylpyridine N-oxides
He, Feilong; Chen, Guanghui; Yang, Junxia; Liang, Guojuan; Deng, Ping; Xiong, Yan; Zhou, Hui; RSC Advances 8 (2018) 9414–; doi:10.1039/C8RA00552D

data_7230264
_publ_section_title
;
 Catalytic enantioselective Henry reaction of \a-keto esters,
 2-acylpyridines and 2-acylpyridine N-oxides
;
_journal_issue                   17
_journal_name_full               'RSC Advances'
_journal_page_first              9414
_journal_paper_doi               10.1039/C8RA00552D
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H15 N O5'
_chemical_formula_sum            'C12 H15 N O5'
_chemical_formula_weight         253.25
_chemical_name_systematic
'(R)-Isopropyl 2-hydroxy-3-nitro-2-phenylpropanoate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-07-24 deposited with the CCDC.
2018-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.66420(10)
_cell_length_b                   9.5973(2)
_cell_length_c                   22.6622(4)
_cell_measurement_reflns_used    6109
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.93
_cell_measurement_theta_min      5.00
_cell_volume                     1231.94(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            6426
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.919
_diffrn_reflns_theta_min         5.004
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_exptl_transmission_factor_max   0.4682
_exptl_transmission_factor_min   0.2452
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 861 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_coef       0.0094(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+0.1766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1046
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                2208
_reflns_number_total             2247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra00552d2.cif
_cod_data_source_block           cu_cd4_0m
_cod_database_code               7230264
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.465
_shelx_estimated_absorpt_t_max   0.923
_shelx_res_checksum              92141