Highly endo-selective and enantioselective 1,3-dipolar cycloaddition of azomethine ylide with alpha-enones catalyzed by a silver(I)/ThioClickFerrophos complex.
Oura, Ichiro; Shimizu, Kenta; Ogata, Kenichi; Fukuzawa, Shin-Ichi; Organic letters 12 (2010) 1752–1755; doi:10.1021/ol100336q

data_1502909
_publ_section_title
;
 Highly endo-selective and enantioselective 1,3-dipolar cycloaddition of
 azomethine ylide with alpha-enones catalyzed by a
 silver(I)/ThioClickFerrophos complex.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1752
_journal_page_last               1755
_journal_paper_doi               10.1021/ol100336q
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C36 H36 Fe N3 P S '
_chemical_formula_sum            'C36 H36 Fe N3 P S'
_chemical_formula_weight         629.58
_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                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   10.478(3)
_cell_length_b                   10.566(3)
_cell_length_c                   28.685(8)
_cell_measurement_reflns_used    9147
_cell_measurement_temperature    123.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     3175.7(16)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.082
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            23394
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1320.00
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.48
_refine_diff_density_min         -1.34
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  3114 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     381
_refine_ls_number_reflns         7181
_refine_ls_R_factor_gt           0.0620
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0994P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1965
_reflns_number_gt                6170
_reflns_number_total             7181
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol100336q_si_002.cif
_cod_data_source_block           '__20090901_tbu'
_cod_original_cell_volume        3175.6(15)
_cod_original_formula_sum        'C36 H36 Fe N3 P S '
_cod_database_code               1502909