Anti-Selective Asymmetric Nitro-Michael Reaction of Furanones: Diastereocontrol by Catalyst.
Sekikawa, Tohru; Kitaguchi, Takayuki; Kitaura, Hayato; Minami, Tatsuya; Hatanaka, Yasuo; Organic letters 18 (2016) 646–649; doi:10.1021/acs.orglett.5b03539

data_1542654
_publ_section_title
;
 Anti-Selective Asymmetric Nitro-Michael Reaction of Furanones:
 Diastereocontrol by Catalyst.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              646
_journal_page_last               649
_journal_paper_doi               10.1021/acs.orglett.5b03539
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H15 N O4'
_chemical_formula_sum            'C17 H15 N O4'
_chemical_formula_weight         297.30
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9263(2)
_cell_length_b                   14.3580(4)
_cell_length_c                   17.7263(6)
_cell_measurement_reflns_used    20286
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.3
_cell_measurement_theta_min      2.5
_cell_volume                     1508.33(8)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare <i>et al.</i>,  1999)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_detector       'Imaging Plate'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16986
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         3.96
_diffrn_source_current           100.0000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  0.9477
_exptl_absorpt_correction_T_min  0.6126
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
HIGASHI, T. (1999). Numabs - Numerical Absorption Correction, 
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_preparation
;
mounted on a glass fiber with epoxy resin and 
placed in air at room temperature'
;
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0606P)^2^+0.2350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1198
_reflns_number_gt                2341
_reflns_number_total             2634
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03539_si_001.cif
_cod_data_source_block           2-naphpro_x-ray
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1542654