Highly Enantioselective Construction of a Chiral Spirocyclic Structure by the [2 + 2 + 2] Cycloaddition of Diynes andexo-Methylene Cyclic Compounds
Kyoji Tsuchikama; Yusuke Kuwata; Takanori Shibata; Journal of the American Chemical Society 128 (2006) 13686–13687; doi:10.1021/ja064257u

data_4111006
_publ_section_title
;
 Highly Enantioselective Construction of a Chiral Spirocyclic Structure by
 the [2 + 2 + 2] Cycloaddition of Diynes andexo-Methylene Cyclic Compounds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13686
_journal_page_last               13687
_journal_paper_doi               10.1021/ja064257u
_journal_volume                  128
_journal_year                    2006
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C21 H25 N O4 S '
_chemical_formula_sum            'C21 H25 N O4 S'
_chemical_formula_weight         387.49
_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                90.0000
_cell_angle_beta                 90.09(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   7.536(5)
_cell_length_b                   9.322(5)
_cell_length_c                   13.574(6)
_cell_measurement_reflns_used    9231
_cell_measurement_temperature    123.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     953.6(9)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.016
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9301
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.812
_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    1.349
_exptl_crystal_description       prism
_exptl_crystal_F_000             412.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         1.10
_refine_diff_density_min         -0.71
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1822 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4029
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0038Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                4026
_reflns_number_total             4138
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja064257usi20060627_112627.cif
_cod_data_source_block           '_kama0403'
_cod_original_formula_sum        'C21 H25 N O4 S '
_cod_database_code               4111006