Sc3±catalyzed aldol-type additions of N-benzoylcyclopropanecarboxamides via iodide-mediated ring-opening: stereoselective synthesis of gamma-lactams.
Wiedemann, Sean H.; Noda, Hidetoshi; Harada, Shinji; Matsunaga, Shigeki; Shibasaki, Masakatsu; Organic letters 10 (2008) 1661–1664; doi:10.1021/ol800401g

data_1504627
_publ_section_title
;
 Sc3+-catalyzed aldol-type additions of N-benzoylcyclopropanecarboxamides
 via iodide-mediated ring-opening: stereoselective synthesis of
 gamma-lactams.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1661
_journal_page_last               1664
_journal_paper_doi               10.1021/ol800401g
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C17 H17 N O4 '
_chemical_formula_sum            'C17 H17 N O4'
_chemical_formula_weight         299.33
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.426(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   11.1675(8)
_cell_length_b                   7.3412(5)
_cell_length_c                   18.1543(15)
_cell_measurement_reflns_used    10950
_cell_measurement_temperature    95.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1468.25(19)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR2002
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13614
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.30
_refine_ls_extinction_coef       146(29)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3358
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[1.0000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                2446
_reflns_number_total             3358
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol800401g-file006.cif
_cod_data_source_block           '_070213harada'
_cod_original_formula_sum        'C17 H17 N O4 '
_cod_database_code               1504627