Highly enantioselective and diastereoselective 1,3-dipolar cycloaddition reactions between azomethine imines and 3-acryloyl-2-oxazolidinone catalyzed by binaphthyldiimine-Ni(II) complexes.
Suga, Hiroyuki; Funyu, Akira; Kakehi, Akikazu; Organic letters 9 (2007) 97–100; doi:10.1021/ol062675y

data_1505250
_publ_section_title
;
 Highly enantioselective and diastereoselective 1,3-dipolar cycloaddition
 reactions between azomethine imines and 3-acryloyl-2-oxazolidinone
 catalyzed by binaphthyldiimine-Ni(II) complexes.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              97
_journal_page_last               100
_journal_paper_doi               10.1021/ol062675y
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C18 H20 Br N3 O4 '
_chemical_formula_sum            'C18 H20 Br N3 O4'
_chemical_formula_weight         422.28
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90
_cell_angle_beta                 95.3(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.51(1)
_cell_length_b                   15.22(1)
_cell_length_c                   10.76(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      14.9
_cell_measurement_theta_min      14.6
_cell_volume                     898.5(19)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan for Windows version 1.06)'
_computing_publication_material  'teXsan for Windows version 1.06)'
_computing_structure_refinement  'teXsan for Windows version 1.06)'
_computing_structure_solution
;
SIR92 (Altomare, et. al. 1994)
;
_diffrn_ambient_temperature      296.2
_diffrn_measurement_device       'Rigaku AFC5S'
_diffrn_measurement_method       \w-2\q
_diffrn_orient_matrix_UB_11      -0.10355
_diffrn_orient_matrix_UB_12      -0.03431
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_diffrn_orient_matrix_UB_21      -0.14994
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_diffrn_orient_matrix_UB_23      -0.04925
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_diffrn_orient_matrix_UB_32      -0.05127
_diffrn_orient_matrix_UB_33      -0.05793
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.22003
_diffrn_reflns_av_sigmaI/netI    0.063
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2356
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.67
_diffrn_standards_decay_%        1.02
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.323
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_type
;
\y scans (North,Phillips & Matthews, 1968)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             432.00
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.78
_exptl_crystal_size_min          0.62
_refine_diff_density_max         7.89
_refine_diff_density_min         -6.49
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   4.054
_refine_ls_goodness_of_fit_ref   4.050
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     234
_refine_ls_number_reflns         1453
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0760
_refine_ls_shift/su_max          1.5700
_refine_ls_shift/su_mean         0.1239
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00000|Fo|^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0510
_refine_ls_wR_factor_ref         0.0510
_reflns_number_gt                1453
_reflns_number_total             2146
_reflns_threshold_expression     I>2.00\s(I)
_cod_data_source_file            ol062675ysi20061102_040617.cif
_cod_data_source_block           '_suga23___________________'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        899(2)
_cod_original_sg_symbol_H-M      'P 21       '
_cod_original_formula_sum        'C18 H20 Br N3 O4 '
_cod_database_code               1505250