Catalytic Asymmetric Friedel-Crafts/Protonation of Nitroalkenes and N-Heteroaromatics
Takayoshi Arai; Atsuko Awata; Makiko Wasai; Naota Yokoyama; Hyuma Masu; Journal of Organic Chemistry 76 (2011) 5450–5456; doi:10.1021/jo200546a

data_4026410
_publ_section_title
;
 Catalytic Asymmetric Friedel-Crafts/Protonation of Nitroalkenes and
 N-Heteroaromatics
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5450
_journal_page_last               5456
_journal_paper_doi               10.1021/jo200546a
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C17 H22 N2 O4'
_chemical_formula_weight         318.37
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 105.957(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.252(4)
_cell_length_b                   8.312(3)
_cell_length_c                   16.889(5)
_cell_measurement_reflns_used    4446
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.29
_cell_volume                     1788.7(10)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'omega scans'
_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  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9728
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.50
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_correction_T_min  0.9710
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0724P)^2^+0.2214P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                3290
_reflns_number_total             4122
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200546a_si_001.cif
_cod_data_source_block           Figure_2
_cod_original_cell_volume        1788.7(9)
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4026410